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O-Toluidine
O-Toluidine
O-Toluidine
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o-Toluidine
Names
Preferred IUPAC name
2-Methylaniline[1]
Other names
o-Methylaniline
o-Toluidine
1-Amino-2-methylbenzene
2-Aminotoluene, 2-Toluamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.209 Edit this at Wikidata
EC Number
  • 202-429-0
KEGG
UNII
UN number 1708 (O-TOLUIDINE)
  • InChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3
    Key: RNVCVTLRINQCPJ-UHFFFAOYSA-N
  • CC1=CC=CC=C1N
Properties
C7H9N
Molar mass 107.156 g·mol−1
Appearance Colorless liquid
Odor Aromatic, aniline-like odor
Density 1.004 g/cm3
Melting point −23.68 °C (−10.62 °F; 249.47 K)
Boiling point 200 to 202 °C (392 to 396 °F; 473 to 475 K)
0.19 g/100 ml at 20 °C
Vapor pressure 0.307531 mmHg (25 °C)
1.56987
Viscosity 4.4335 (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, moderately toxic
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H302, H319, H331, H350, H400
P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P304+P340, P305+P351+P338, P308+P313, P311, P321, P330, P337+P313, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 85 °C (185 °F; 358 K)
481.67 °C (899.01 °F; 754.82 K)
Lethal dose or concentration (LD, LC):
900 mg/kg (rat, oral)
323 mg/kg (rabbit, oral)
Related compounds
Related compounds
 Toluidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

o-Toluidine (ortho-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precursor to the herbicides metolachlor and acetochlor.[2]

Synthesis and reactions

[edit]

o-Toluidine is produced industrially by nitration of toluene to give a mixture of nitrotoluenes, favoring the ortho isomer. This mixture is separated by distillation. 2-Nitrotoluene is hydrogenated to give o-toluidine.[2]

The conversion of o-toluidine to the diazonium salt gives access to the 2-bromo, 2-cyano-, and 2-chlorotoluene derivatives.[3] [4] [5] N-acetylation is also demonstrated.[6]

Safety

[edit]

The LD50 (oral, rats) is 670 mg/kg.[2]

Binding of hemoglobin

[edit]

o-Nitrosotoluene, a metabolite of o-toluidine, converts hemoglobin to methemoglobin, resulting in methemoglobinemia.[7][8][ISBN missing][9]

o-Nitrosotoluene is suspected of causing bladder cancer in rats.[10][11][12] Nitrosotoluene exposure has been researched in a number of different degrees in animals.[13][14][15][16]

Carcinogenicity

[edit]

In the U.S., o-toluidine was first listed in the Third Annual Report on Carcinogens as 'reasonably anticipated to be a human carcinogen' in 1983, based on sufficient evidence from studies in experimental animals. The Report on Carcinogens (RoC) is a U.S. congressionally-mandated, science-based public health report that identifies agents, substances, mixtures, or exposures in the environment that pose a hazard to people residing in the United States[17] Since then, other cancer related studies have been published and the listing of o-toluidine was changed to 'known to be a human carcinogen'. o-toluidine was especially linked to bladder cancer. This was done 31 years later in the Thirteenth Report on Carcinogens (2014).[14] The International Agency for Research on Cancer (IARC) has classified o-toluidine as 'carcinogenic to humans (group 1)'.[18]

Metabolism

[edit]

o-Toluidine is absorbed through inhalation and dermal contact as well as from the gastrointestinal tract.[19][13][20][21]

The metabolism of o-toluidine involves many competing activating and deactivating pathways, including N-acetylation, N-oxidation, and N-hydroxylation, and ring oxidation.[22] 4-Hydroxylation and N-acetylation of toluidine are the major metabolic pathways in rats. The primary metabolism of o-toluidine takes place in the endoplasmic reticulum. Exposure to o-toluidine enhances the microsomal activity of aryl hydrocarbon hydroxylase (particularly in the kidney), NADPH-cytochrome c reductase and the content of cytochrome P-450. Cytochrome P450–mediated N-hydroxylation to N-hydroxy-o-toluidine, a carcinogenic metabolite, occurs in the liver. N-Hydroxy-o-toluidine can be either metabolized to o-nitrosotoluene or conjugated with glucuronic acid or sulfate and transported to the urinary bladder via the blood. Once in the bladder, N-hydroxy-o-toluidine can be released from the conjugates in an acidic urine environment to either react directly with DNA or be bio-activated via sulfation or acetylation by cytosolic sulfotransferases or N-acetyltransferases (presumably NAT1).[14] The postulated activated form (based on comparison with other aromatic amines), N-acetoxy-o-toluidine, is a reactive ester that forms electrophilic arylnitrenium ions that can bind to DNA.[22][23][10] Other activation pathways (ring-oxidation pathways) for aromatic amines include peroxidase-catalyzed reactions that form reactive metabolites (quinone-imines formed from nonconjugated phenolic metabolites) in the bladder. These metabolites can produce reactive oxygen species, resulting in oxidative cellular damage and compensatory cell proliferation. Support for this mechanism comes from studies of oxidative DNA damage induced by o-toluidine metabolites in cultured human cells (HL-60), calf thymus DNA, and DNA fragments from key genes thought to be involved in carcinogenesis (the c-Ha-ras oncogene and the p53 tumor-suppressor gene).[24][25] Also supporting this mechanism are observations of o-toluidine-induced DNA damage (strand breaks) in cultured human bladder cells and bladder cells from rats and mice exposed in vivo to o-toluidine.[26][27]

Figure 1: Metabolism of o-(methyl-14C)-toluidine hydrochloride in the rat.

Excretion

[edit]

The main excretion pathway is through the urine where up to one-third of the administered compound was recovered unchanged. Major metabolites are 4-amino-m-cresol and to a lesser extent, N-acetyl-4-amino-m-cresol,[20] azoxytoluene, o-nitrosotoluene, N-acetyl-o-toluidine, N-acetyl-o-aminobenzyl alcohol, anthranilic acid, N-acetyl-anthranilic acid, 2-amino-m-cresol, p-hydroxy-o-toluidine. Conjugates that were formed were predominated by sulfate conjugates over glucuronide conjugates by a ratio of 6:1.

[edit]

Prilocaine, an amino amide-type local anesthetic, yields o-toluidine when metabolized by carboxylesterase enzymes.[28] Large prilocaine doses can cause methemoglobinemia due to oxidation of hemoglobin by o-toluidine.[29]

Drugs List

[edit]
  1. Aptocaine
  2. Asulacrine
  3. Dazepinil
  4. Methaqualone
  5. Metolazone
  6. Prilocaine
  7. Quatacaine (Tanacaine)

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

O-Toluidine

View on Grokipedia
from Grokipedia
o-Toluidine, also known as 2-methylaniline, is an with the molecular formula C₇H₉N and the CH₃C₆H₄NH₂, featuring a benzene ring with an amino group and an adjacent (ortho) methyl substituent. It is industrially produced primarily through the catalytic of o-nitrotoluene. As a pale yellow to colorless liquid with an aromatic , o-toluidine has a of 200.3 °C, a of -23.7 °C, and a density of 1.01 g/cm³ at 20 °C; it exhibits low water solubility (1.5 g/L at 25 °C) but is miscible with most organic solvents, and it may darken to reddish-brown upon prolonged exposure to air and light. o-Toluidine serves as a key intermediate in the , particularly for manufacturing azo used in textiles, as well as rubber accelerators, certain pharmaceuticals, and pesticides. Its reactivity as an enables derivatization into various compounds, including diazonium salts for synthesis. Despite its industrial utility, o-toluidine is highly toxic, readily absorbed through inhalation, ingestion, or skin contact, and causes by oxidizing in red blood cells. It is classified by the International Agency for Research on Cancer (IARC) as carcinogenic to humans (), with sufficient evidence linking occupational exposure to . Regulatory bodies such as the U.S. (OSHA) set permissible exposure limits at 5 ppm (skin notation) to minimize risks, and it is also toxic to aquatic life.

Properties

Physical properties

o-Toluidine has the molecular formula C₇H₉N and a of 107.15 g/mol. It appears as a clear, colorless to light yellow liquid at , though commercial samples may exhibit a yellowish tint due to impurities and can turn reddish-brown upon prolonged exposure to air and light.
PropertyValueConditionsSource
Melting point-23 °C-Fisher SDS
Boiling point199–200 °C760 mmHgSigma-Aldrich
Density1.004 g/cm³20 °CAlpha Chemika
Solubility in water1.5 g/100 mL20 °CPubChem
Flash point85 °CClosed cupSigma-Aldrich
Vapor pressure0.26 mmHg25 °CPubChem
Refractive index1.56920 °C (n_D)PubChem

Chemical properties

o-Toluidine, with the systematic name 2-methylaniline, features a benzene ring substituted with an amino group (-NH₂) at position 1 and a (-CH₃) at the ortho position 2. This structural arrangement distinguishes it from (C₆H₅NH₂) and the other isomers, meta-toluidine (3-methylaniline) and para-toluidine (4-methylaniline), where the is positioned adjacently, meta, or para relative to the amino , respectively. As a primary , o-toluidine displays characteristic reactivity centered on the nucleophilic -NH₂ group, which participates in reactions with electrophiles, such as by acids to form salts exothermically or incompatibility with strong oxidizers and bases. The amino substituent strongly activates the aromatic ring toward , acting as an ortho-para director due to its electron-donating effect, while the ortho provides additional activation through but may impose steric hindrance on substitutions at positions adjacent to both substituents. Spectroscopic analysis confirms the functional groups: the (IR) spectrum shows characteristic N-H stretching absorptions for the primary around 3300–3500 cm⁻¹. In the ¹H (NMR) spectrum, the appears at approximately 2.09 ppm, the amino protons at 3.48 ppm, and the aromatic protons resonate between 6.59 and 7.01 ppm, reflecting the deshielding effects of the substituents. o-Toluidine is sensitive to oxidation upon exposure to air and light, gradually developing reddish-brown colored impurities over time due to oxidative degradation.

Synthesis

Industrial production

o-Toluidine is primarily produced industrially through the nitration of toluene followed by selective hydrogenation of the resulting 2-nitrotoluene. In the nitration step, toluene is reacted with a mixed acid system consisting of nitric acid (HNO₃) and sulfuric acid (H₂SO₄) under controlled conditions to yield a mixture of mononitrotoluene isomers, where the ortho isomer (2-nitrotoluene) constitutes approximately 60% of the product. The isomers are then separated via fractional distillation to isolate 2-nitrotoluene, which is subsequently reduced to o-toluidine. The reduction of typically occurs through catalytic , either in the vapor phase or liquid phase at elevated temperatures (around 200–300°C) and pressures, using catalysts such as nickel-on-kieselguhr, , or to achieve high selectivity for the primary . This process is conducted continuously in modern facilities to optimize efficiency and minimize byproducts like isomers or over-reduced compounds. An alternative route involves the reaction of o-chlorotoluene with (NaNH₂) in liquid , yielding a mixture of o- and m-, though the nitration- method remains dominant due to its scalability. Commercial production of o-toluidine was first established in the in 1880, coinciding with the expansion of the industry in the late , and has since become a high-volume chemical manufactured primarily in hubs such as (16 producers), (11 producers), and the (6 producers as of 1999). Global annual production reached an estimated 59,000 metric tons in 2001, reflecting its role as a key intermediate in dyes, pigments, and rubber chemicals, with ongoing output in the tens of thousands of tons primarily driven by demand in these sectors.

Laboratory methods

o-Toluidine is commonly synthesized in laboratory settings through the reduction of , a method that offers versatility for small-scale preparations. This reduction can be achieved using metal-acid systems such as tin in or iron in , known as the Béchamp reduction. In the tin/HCl procedure, is added to granular tin in concentrated HCl, heated to approximately 100°C for 2 hours, followed by basification with NaOH to liberate the free , which is then extracted with an organic like . Similarly, the iron/HCl variant employs iron powder in aqueous HCl at around 100°C under batch conditions, producing o-toluidine directly, which is isolated by and subsequent neutralization. These classical approaches are favored in research due to their simplicity and use of inexpensive reagents, though they generate significant inorganic waste. A milder alternative is catalytic hydrogenation using as in ethanol solvent under pressure. The reaction proceeds at elevated temperature and pressure, typically converting to o-toluidine with high selectivity, as demonstrated in analogous reductions of nitrotoluenes where complete conversion is achieved. This method avoids harsh acids and is suitable for sensitive substrates, with recovered by post-reaction. Alternative synthetic routes include the of o-toluamide, where the amide is treated with and to form an N-bromoamide intermediate that rearranges upon heating to yield o-toluidine via loss of the carbonyl carbon. Another option is the partial reduction of using aqueous ammonium sulfide under phase-transfer conditions in solvent, which selectively reduces the nitro group to amine while minimizing over-reduction. These routes provide access when is unavailable or for studies. Purification of crude o-toluidine, often contaminated with isomers from precursors, typically involves to separate the liquid (boiling point ~200°C at , lower under ) or formation and recrystallization of the salt from aqueous HCl for enhanced purity. The salt is recrystallized from water or , then basified to recover the . Laboratory syntheses of o-toluidine via these reductions generally afford yields of 70–90%, depending on the method and scale, with reactions conducted at to 100°C. To prevent aerial oxidation of the product, an inert atmosphere such as is employed, particularly during and storage.

Uses

Dyes and rubber chemicals

o-Toluidine serves as a key intermediate in the production of various dyes, particularly azo dyes, where it is converted into diazonium salts that couple with or naphthols to form pigments applied in textiles and inks. This diazotization process leverages o-toluidine's reactivity as an to yield colorants such as Acid Red 24 and Solvent Red 24, which are used in industrial dyeing applications. Additionally, o-toluidine contributes to the synthesis of thioindigo dyes, serving as a precursor for derivatives employed in vat dyeing of fabrics. Other examples include its role in producing magenta dyes like Magenta I (Basic Violet 14) and safranine T (Basic Red 2), which find use in direct dyeing processes for textiles. In the rubber industry, o-toluidine is utilized as an intermediate for vulcanization accelerators and antioxidants that enhance the durability and performance of rubber products, such as tires. A prominent example is di-o-tolylguanidine (DOTG), synthesized from o-toluidine, which acts as a delayed-action accelerator in conjunction with thiazoles and thiurams to promote efficient crosslinking during of natural and synthetic rubbers. This compound improves scorch safety and curing rates, contributing to the production of high-quality rubber goods. The and rubber chemicals sectors represent the principal applications for o-toluidine, accounting for the largest share of its global consumption due to its versatility in industrial colorants and additives. Over 90 dyes incorporate o-toluidine as a building block, underscoring its significant market impact in these areas.

Agrochemicals and pharmaceuticals

o-Toluidine functions as a critical intermediate in the production of several agrochemicals, particularly . It is essential for synthesizing the chloroacetanilide metolachlor and acetochlor, which are applied pre-emergence to control annual grasses and broadleaf weeds in crops such as corn and soybeans. The synthesis begins with N-alkylation of o-toluidine using ethylating agents to yield 6-ethyl-o-toluidine, followed by with chloroacetyl chloride to form the active structure; this pathway accounts for a significant portion of o-toluidine's industrial consumption in . In pesticide manufacturing, o-toluidine contributes to the creation of select and via formation, such as or linkages. For instance, it is incorporated into triflumizole, a broad-spectrum effective against powdery mildew and other fungal pathogens on fruits and , through condensation reactions forming the N-(o-toluidine) ethylidene core. Similarly, pioxaniliprole, an anthranilic targeting lepidopteran pests in and , is derived from o-toluidine by initial with chloroacetyl , followed by cyclization to a intermediate and further elaboration. These applications leverage o-toluidine's reactivity as an to build heterocyclic structures with . In the pharmaceutical sector, o-toluidine serves as a precursor for prilocaine, a local anesthetic used in dental and minor surgical procedures. The synthesis involves of o-toluidine with 2-chloropropionyl to produce the intermediate amide, which is then displaced with to yield prilocaine; notably, prilocaine undergoes back to o-toluidine, which can lead to at high doses due to oxidation. This underscores the compound's role in amide-type anesthetics, though it limits dosage in susceptible patients. Regulatory oversight on o-toluidine in agrochemicals and pharmaceuticals stems from its as a human carcinogen (Group 1 by IARC), primarily linked to risk from occupational exposure. In the United States, the EPA regulates its use under TSCA, imposing reporting requirements for manufacturing and restricting releases into water under the Clean Water Act, while OSHA sets a of 5 ppm to mitigate and dermal risks in production facilities. These controls have driven efforts to develop alternative intermediates for herbicides like , reducing reliance on o-toluidine in formulations to minimize environmental and worker exposure.

Safety and toxicology

Acute toxicity and exposure

o-Toluidine can be absorbed through multiple routes of exposure, including of its vapor, dermal absorption through the , and . Occupational exposure primarily occurs via and contact in industrial settings such as dye manufacturing. The (OSHA) has established a (PEL) of 5 ppm as an 8-hour time-weighted average, with a skin notation indicating significant dermal absorption potential. Acute exposure to o-toluidine acts as an irritant to the skin, eyes, and , potentially causing redness, pain, and upon contact. Systemic effects include , manifesting as , , , and at higher doses, due to . arises from the formation of the o-nitrosotoluene , which leads to reduced oxygen-carrying capacity in the blood. Toxicity studies indicate moderate acute oral toxicity, with an LD50 of 670 mg/kg in rats, while dermal toxicity is lower, with an LD50 greater than 2000 mg/kg in rabbits. Low-dose exposures can still produce symptoms such as nausea and dizziness, emphasizing the need for strict exposure controls. The primary biochemical mechanism of o-toluidine's acute toxicity involves binding of both the parent compound and its nitroso derivative to hemoglobin. This interaction oxidizes the iron center from ferrous (Fe²⁺) to ferric (Fe³⁺) form, converting functional hemoglobin to methemoglobin, which impairs oxygen transport and delivery to tissues. The o-nitrosotoluene metabolite specifically facilitates this oxidation through redox cycling, exacerbating the hypoxic effects observed in exposed individuals.

Carcinogenicity

o-Toluidine is classified as carcinogenic to s (Group 1) by the International Agency for Research on Cancer (IARC), based on sufficient evidence from human epidemiological studies and animal experiments demonstrating its role in inducing . The U.S. National Toxicology Program (NTP) lists o-toluidine as a known carcinogen in its Report on Carcinogens, upgraded from "reasonably anticipated" in the 13th edition released in 2014, supported by sufficient evidence of urinary in occupationally exposed workers. The U.S. Environmental Protection Agency (EPA) classifies o-toluidine as a Group B2 probable carcinogen, reflecting limited human evidence combined with sufficient animal data linking it to tumors. Human evidence for o-toluidine's carcinogenicity stems primarily from occupational exposures in the dye and rubber industries, where it has been consistently associated with increased risk. Multiple cohort studies, including a 1991 analysis of 1,749 U.S. chemical workers exposed to o-toluidine, reported a standardized incidence ratio (SIR) of 6.5 for , with risks rising with duration and intensity of exposure. A follow-up to this cohort identified 19 additional cases by 2004, bringing the total to 34 and confirming ongoing excess risk even after exposure cessation, implicating o-toluidine over co-exposures like . Other studies, such as those in UK and Italian dye workers, showed similar elevated risks (SIR up to 72.7), establishing sufficient evidence for causation despite potential confounders. In experimental animals, o-toluidine induces tumors at multiple sites, providing mechanistic concordance with findings. to rats caused urinary transitional-cell carcinomas and mesothelial sarcomas in both sexes, while in mice, it led to hepatocellular carcinomas, hemangiosarcomas, and subcutaneous fibrosarcomas. These effects were observed in studies by the National Toxicology Program (1979, 1996) and others, with dose-dependent tumor increases in the urinary tract mirroring occupational patterns. The carcinogenic mechanism involves metabolic activation of o-toluidine to reactive intermediates that form DNA adducts, particularly in bladder tissue. Human bladder samples from tumor patients revealed o-toluidine-specific DNA adducts at levels up to 8.72 fmol/µg DNA, supporting genotoxic damage as a key pathway. As a non-threshold genotoxic carcinogen, no safe exposure level exists, prompting regulatory actions such as its ban in hair dyes and other consumer products under EU Cosmetics Regulation (Annex II). Occupational limits, like OSHA's 5 ppm permissible exposure limit, aim to minimize risk but do not eliminate it.

Metabolism and biotransformation

o-Toluidine is rapidly absorbed in humans through the , , and , with approximately 15% penetration occurring within 7 hours and 50% within 24 hours. Following absorption, it distributes systemically, accumulating primarily in the liver and , as observed in animal models where highest concentrations were found in liver, , , and blood. In phase I metabolism, o-toluidine undergoes N-oxidation primarily by enzymes, including , , and , forming the reactive intermediate N-hydroxy-o-toluidine in the liver. Additionally, ring oxidation produces hydroxy derivatives such as 4-amino-m-cresol. Phase II metabolism involves N-acetylation of o-toluidine by N-acetyltransferase 2 (NAT2) to yield acetyl-o-toluidine, while hydroxylated metabolites undergo sulfation and for increased water solubility. The N-hydroxy-o-toluidine metabolite is activated through further biotransformation, such as acetylation to N-acetoxy-o-toluidine followed by deacetylation, generating an electrophilic nitrenium ion that binds to DNA and contributes to genotoxicity. This pathway is implicated in bladder carcinogenesis. In methemoglobinemia, the N-hydroxylated metabolite undergoes co-oxidation with oxyhemoglobin, forming methemoglobin and a nitroso intermediate such as nitrosotoluene. Genetic variations in NAT2, particularly slow acetylator phenotypes, increase the risk of among exposed individuals by prolonging exposure to the reactive N-hydroxy-o-toluidine and its activated forms.

Excretion and metabolites

The primary route of elimination for o-toluidine is renal via , with over 90% of the administered dose recovered in within 72 hours in rats following . In humans and animals, up to 30–40% of the dose is excreted unchanged as parent o-toluidine, while the remainder appears as metabolites, with urinary recovery reaching 74–83% within 48 hours in rats after subcutaneous dosing. Major urinary metabolites include the ring-hydroxylated product 4-amino-m-cresol and its acetylated derivative N-acetyl-4-amino-m-cresol, which together account for a significant portion of the excreted dose, often as or conjugates. Minor metabolites, such as azoxy and azo dimers, have been identified in trace amounts in some studies of exposure. Fecal is minimal, typically less than 5% of the dose in rats, with small amounts also eliminated via exhaled air (approximately 1%). The elimination of o-toluidine is approximately 3–6 hours in human plasma and 12–15 hours in rat plasma, reflecting rapid clearance but potential for accumulation in bladder due to pH-dependent tubular reabsorption, where alkaline enhances of this . Enterohepatic recirculation of conjugated metabolites can prolong systemic exposure, though this pathway is limited compared to direct renal elimination. differences influence patterns; for instance, rats eliminate a higher proportion of unchanged parent compound (up to 36% at low oral doses) compared to humans, where predominates. Analytical detection of urinary o-toluidine and its metabolites in exposed workers relies on methods such as (HPLC) with UV or detection, enabling quantification of post-shift levels that are often 6–25 times higher than pre-shift baselines in occupational settings.

References

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