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Chlorobutanol
Chlorobutanol
Chlorobutanol
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Chlorobutanol
Names
Preferred IUPAC name
1,1,1-Trichloro-2-methylpropan-2-ol
Other names
1,1,1-Trichloro-2-methyl-2-propanol; Chlorbutol; Chloreton; Chloretone; Chlortran; Trichloro-tert-butyl alcohol; 1,1,1-Trichloro-tert-butyl alcohol; 2-(Trichloromethyl)propan-2-ol; tert-Trichlorobutyl alcohol; Trichloro-tert-butanol; Trichlorisobutylalcohol; 2,2,2-Trichloro-1,1-dimethylethanol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.288 Edit this at Wikidata
EC Number
  • 200-317-6
KEGG
UNII
  • InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3 checkY
    Key: OSASVXMJTNOKOY-UHFFFAOYSA-N checkY
  • InChI=1/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
    Key: OSASVXMJTNOKOY-UHFFFAOYAO
  • ClC(Cl)(Cl)C(C)(C)O
Properties
C4H7Cl3O
Molar mass 177.45 g·mol−1
Appearance White solid
Odor Camphor
Melting point 95–99 °C (203–210 °F; 368–372 K)
Boiling point 167 °C (333 °F; 440 K)
Slightly soluble[vague]
Solubility in acetone Soluble
Pharmacology
A04AD04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Xn[clarification needed]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chlorobutanol (trichloro-2-methyl-2-propanol) is an organic compound with the formula CCl3C(OH)(CH3)2. It is a halohydrin‍—‍‌specifically a chlorohydrin. Chlorobutanol acts as a preservative, sedative, hypnotic, and weak local anesthetic similar in nature to chloral hydrate; it also has antibacterial and antifungal properties.[1] Chlorobutanol is typically used at a concentration of 0.5% where it lends long term stability to multi-ingredient formulations. However, it retains antimicrobial activity at 0.05% in water. Chlorobutanol has been used in anesthesia and euthanasia of invertebrates and fishes.[2][3] It is a white, volatile solid with a camphor-like odor.

Synthesis

[edit]
Sublimed crystals of chlorobutanol

Chlorobutanol was first synthesized in 1881 by the German chemist Conrad Willgerodt (1841–1930).[4]

Chlorobutanol is formed by the reaction of chloroform and acetone in the presence of potassium or sodium hydroxide. It may be purified by sublimation or recrystallisation.[5]

Parthenogenesis

[edit]

Chlorobutanol has proven effective at stimulating parthenogenesis in sea urchin eggs up to the pluteus stage, possibly by increasing irritability to cause stimulation. For the eggs of the fish Oryzias latipes, however, chlorobutanol only acted as an anesthetic.[6]

Pharmacology and toxicity

[edit]

It is an anesthetic with effects related to isoflurane and halothane.[7]

Chlorobutanol is toxic to the liver, a skin irritant and a severe eye irritant.[8]

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Chlorobutanol

View on Grokipedia
from Grokipedia
Chlorobutanol, also known as chlorbutol or chloretone, is a synthetic tertiary alcohol compound with the molecular formula C₄H₇Cl₃O and a molecular weight of 177.45 g/mol. It appears as a colorless to white crystalline solid with a camphor-like , a of 97°C, and a of 167°C, and it is formed by the of to acetone. As an alcohol-based lacking activity, chlorobutanol exhibits broad-spectrum properties against and fungi, making it widely used in pharmaceutical formulations, particularly in ophthalmic solutions such as at concentrations around 0.5%. It is also employed in , injectables, and other multi-dose preparations to prevent microbial , though its limits higher concentrations in some applications. Beyond preservation, chlorobutanol demonstrates pharmacological effects, including sedative-hypnotic activity and weak local anesthetic actions, historically utilized in oral sedatives and topical preparations. Its terminal in the body is approximately 10.3 days, and it is approved for use in various medicinal products, though reactions have been reported, prompting restrictions in single-dose vials for sensitive patients. Safety considerations include its classification as a and eye irritant, with potential to cause upon ocular exposure, and oral toxicity (LD50 in humans estimated at 50-500 mg/kg), necessitating careful handling and avoidance of ingestion or prolonged contact. Regulatory bodies like the FDA and EMA permit its use as a at safe levels for lifetime exposure in approved products, but it is not recommended for neonates or in formulations where alternatives are available due to potential risks.

Chemical Properties

Molecular Structure and Formula

Chlorobutanol is an classified as a chlorohydrin, with the molecular formula C4H7Cl3OC_4H_7Cl_3O. Its IUPAC name is 1,1,1-trichloro-2-methylpropan-2-ol, alternatively expressed as 2-(trichloromethyl)-2-propanol, reflecting the carbon chain and substituent positions. Common synonyms include chlorbutol and chloretone, the latter derived from its historical association with applications. The molecular structure features a tertiary alcohol where the hydroxyl group is attached to a central carbon bearing two methyl groups and a trichloromethyl (-CCl₃) , positioning the three atoms on the adjacent carbon. This arrangement results in a of 177.45 g/mol, calculated from the atomic weights of its constituent elements. Chlorobutanol serves as a to (CCl₃CH(OH)₂), differing primarily by the replacement of the -CH(OH)₂ group with -C(OH)(CH₃)₂, which modifies its reactivity while preserving similar halogenated alcohol characteristics.

Physical Characteristics

Chlorobutanol is a crystalline solid at , often appearing as colorless to crystals or powder. It exhibits a characteristic camphor-like , which is noticeable even in small quantities. The compound has a ranging from 95 to 99 °C for the anhydrous form, transitioning from a solid to a liquid state within this narrow temperature interval. Its is reported at 167 °C, at which point it decomposes rather than fully vaporizing. The density of chlorobutanol is approximately 1.4 g/cm³, reflecting its compact crystalline structure. Chlorobutanol demonstrates notable volatility, as it sublimes readily under reduced pressure or moderate heating, a property that facilitates its purification through sublimation techniques. This sublimation behavior contributes to its utility in certain pharmaceutical formulations requiring controlled or stability.

Solubility and Stability

Chlorobutanol demonstrates moderate in , with approximately 0.8 g dissolving per 100 mL at 20 °C, classifying it as slightly soluble under standard conditions. This limited aqueous arises from its nonpolar trichloromethyl group, which hinders extensive hydration. In contrast, the compound exhibits high in organic solvents, including acetone, (very soluble, with 1 g dissolving in about 1 mL), and fatty oils (freely soluble), making it suitable for incorporation into lipid-based or alcoholic formulations. The stability of chlorobutanol is pH-dependent, with high stability in acidic environments ( ~90 years at 3) but faster base-catalyzed degradation in neutral and alkaline conditions ( ~3 months at 7.5). It exhibits effective activity below 5.5, with optimal performance in acidic conditions ( 3–5) where solutions can maintain integrity for months. Exposure to elevated temperatures accelerates , producing and other acidic byproducts, while the compound's volatility leads to sublimation under heat. In pharmaceutical contexts, the hydrous form of chlorobutanol, containing 5–10% water (often as a hemihydrate with up to 0.5 molecules of water per molecule), is preferentially used over the anhydrous variant due to enhanced solubility and ease of handling. This hydrated structure improves dissolution rates without significantly compromising stability in neutral to mildly acidic media, facilitating its role in multi-dose preparations. The anhydrous form, while more stable in dry conditions, sublimes more readily and requires careful control to prevent moisture absorption.

Synthesis

Historical Development

Chlorobutanol was first synthesized in 1881 by German chemist Conrad Willgerodt, who explored derivatives of as potential medicinal agents amid growing interest in hypnotics and during the late . This compound, initially known as trichlorobutyl alcohol, emerged from efforts to modify —a well-established sedative introduced in 1832—to create variants with potentially improved therapeutic profiles. Early pharmacological evaluation began in 1894 when American pharmacologist John Jacob Abel conducted the first animal tests, demonstrating chlorobutanol's hypnotic effects and ability to act as an on , properties akin to those of . These findings, published in medical journals, highlighted its potential as a mild and , though initial human trials by researchers like Arthur Oppenheimer in the mid-1890s revealed concerns over , including alarming symptoms in some patients. By the late 1890s, chlorobutanol gained further recognition in scientific circles for its sedative-hypnotic actions, positioning it as a candidate for broader clinical application despite ongoing debates about safety. Commercialization accelerated in the early 20th century through the efforts of & Co., which marketed the compound under the trade name Chloretone starting around 1897. The company distributed over 30,000 tablets for clinical testing by late and promoted it aggressively in , such as E.M. Houghton's 1899 article in the Journal of the , emphasizing its efficacy as a safe and . This adoption marked chlorobutanol's transition from laboratory curiosity to pharmaceutical staple, with early 20th-century formulations incorporating it for uses in tablets and solutions, though professional skepticism persisted into the due to reports. By the , its antimicrobial properties were increasingly noted, leading to incorporation as a in injectable and ophthalmic preparations.

Laboratory Preparation

The laboratory preparation of chlorobutanol involves the base-catalyzed of to acetone, a classic method that generates the trichloromethyl intermediate under basic conditions. This reaction, first demonstrated in the late , remains the standard laboratory route due to its simplicity and use of readily available reagents. The process begins by mixing acetone ((CH₃)₂CO) and (CHCl₃) in a dry conical flask, typically in a molar ratio of approximately 2:1 to 5:1 acetone to , and cooling the mixture to 0–5°C to manage the exothermic nature of the reaction. An alcoholic solution of (KOH) or (NaOH) is then added gradually with stirring at , often over 15–30 minutes, followed by allowing the mixture to stand for . The overall reaction is: \ce(CH3)2CO+CHCl3+KOH−>(CH3)2C(OH)CCl3+KCl+H2O\ce{(CH3)2CO + CHCl3 + KOH -> (CH3)2C(OH)CCl3 + KCl + H2O} This equation represents the formation of chlorobutanol ((CH₃)₂C(OH)CCl₃) as a white crystalline solid. Under typical laboratory conditions, yields range from 60% to 70%, depending on factors such as temperature control, base concentration, and reaction time; for instance, optimized procedures at low temperatures (-5°C) with reflux have achieved up to 59–66% yield based on chloroform. The crude product is isolated by filtration, with excess acetone removed by distillation or evaporation if needed. Purification is essential due to potential impurities from side reactions, and it is commonly performed by recrystallization from or a water- mixture to achieve pharmaceutical-grade purity (typically >98%). Alternatively, sublimation under reduced pressure can be employed to obtain a highly pure product, taking advantage of chlorobutanol's volatility without decomposition.

Pharmaceutical and Medical Uses

Preservative Applications

Chlorobutanol serves as a key in various pharmaceutical and cosmetic products, primarily at a concentration of 0.5% to prevent microbial and extend . It is commonly incorporated into , ear drops, nasal sprays, dental preparations such as mouthwashes, and injectable solutions, where it helps maintain sterility in multi-ingredient formulations. This usage aligns with its role in stabilizing aqueous-based products against bacterial and fungal growth during storage and repeated access. The mechanism of chlorobutanol involves disruption of the in microbial cell membranes, leading to increased permeability and eventual , without relying on properties. This action provides broad-spectrum efficacy against both Gram-positive and , as well as certain fungi, making it suitable for diverse formulations. Unlike preservatives such as , chlorobutanol exhibits no activity, avoiding issues like foaming or destabilization of emulsions in sensitive preparations. In specific applications, chlorobutanol is included in , creams, and multi-dose vials to inhibit microbial proliferation, with retained activity observed at lower concentrations such as 0.05% in aqueous solutions. Its advantages include broad-spectrum protection and compatibility at typical use levels, as recognized in the National Formulary (NF) and (USP) standards for pharmaceutical . These properties position it as a reliable choice for needs in products requiring minimal interference with formulation integrity.

Sedative and Anesthetic Effects

Chlorobutanol exhibits sedative-hypnotic properties akin to those of , inducing that promotes relaxation and sleep. Historically, it has been employed orally to treat and provide pre-anesthetic prior to minor surgical or dental procedures, leveraging its ability to calm patients and reduce anxiety without significant respiratory depression at therapeutic doses. In , it serves as a mild internal , particularly for managing persistent associated with in dogs, though its use is cautioned in animals with hepatic or renal impairment due to prolonged elimination. As a weak local , chlorobutanol provides numbing effects when applied topically, suitable for minor dermatological or oral procedures by disrupting neuronal membrane integrity and reducing sensory transmission. It has been incorporated into dental formulations, such as 1-5% dusting powders or 10% ointments combined with clove oil, to offer mild pain relief and during extractions or for alleviating . These properties contribute to its role in topical preparations for surface analgesia, though the effect is modest compared to modern agents. Typical oral dosages for sedative effects range from 0.5 to 2 g, often administered as capsules containing 150 mg per unit, with repeated daily intake up to 900-1500 mg in historical formulations like Seducaps for action. For , concentrations of 0.5-1% are used in topical applications to achieve surface numbing without deep penetration. Despite these applications, chlorobutanol's clinical use has diminished in human and veterinary practice due to its extended of approximately 10.3 days, which risks accumulation and side effects, alongside the availability of safer, more effective alternatives like benzodiazepines for and lidocaine for . It occasionally serves a dual role as a in sedative products, enhancing stability while contributing therapeutic effects.

Biological and Research Applications

Induction of Parthenogenesis

Chlorobutanol, also known as chloretone, serves as a chemical agent to induce artificial in unfertilized eggs, mimicking the activation typically triggered by fertilization. This application has been instrumental in research, allowing scientists to study egg activation and early embryonic processes without genetic contribution from . The discovery of chlorobutanol's parthenogenetic effects dates to the early , with initial experiments demonstrating its ability to elevate the fertilization in eggs (Arbacia punctulata). In 1912, Lewis V. Heilbrunn reported that adding chlorobutanol crystals to containing unfertilized eggs induced elevation, a critical first step in parthenogenetic activation, by reducing and facilitating water absorption into the egg's cortical gel layer. This finding built on broader efforts in artificial pioneered by researchers like Jacques Loeb, providing a tool for controlled studies of egg irritability and developmental initiation. Mechanistically, chlorobutanol activates the without fertilization by enhancing cortical granule and elevating the vitelline membrane, often at concentrations of 0.1%. Higher concentrations, such as 0.35%, combined with subsequent hypertonic treatment, promote further development, including cleavage and larval formation. This double-treatment approach, detailed in classic experiments on echinoderms, leverages chlorobutanol's anesthetic-like properties to alter egg permeability and balance, triggering intracellular calcium akin to natural . Key studies from the mid-20th century, including those on species like Hemicentrotus pulcherrimus, confirmed that chlorobutanol treatment yields pluteus larvae, with success rates approaching 100% in optimized conditions (e.g., 0.35% chlorobutanol for 5-10 minutes followed by hypertonic seawater). These experiments, conducted in the 1930s and 1950s, highlighted chlorobutanol's role in producing viable parthenogenetic embryos for morphological and physiological analyses. However, chlorobutanol-induced is limited to early developmental stages; embryos typically arrest beyond the , failing to progress to juvenile or adult forms due to incomplete of paternal genetic factors or sustained metabolic support. This constraint underscores its utility primarily for investigating initial events rather than complete embryogenesis.

Use in Aquatic Organisms

Chlorobutanol serves as an for immobilizing fish species and various during research procedures, typically administered via immersion in aqueous solutions at concentrations of 0.05% to 0.5%. This method allows absorption through gills or , inducing within 2–3 minutes while maintaining spontaneous ventilation. At lower doses within this range, is reversible, with recovery occurring in 3–20 minutes after transfer to , making it suitable for non-lethal handling such as tagging or sampling. Key advantages include its cost-effectiveness relative to anesthetics and lack of persistent residues in due to its volatility, reducing environmental impact post-use.

Pharmacology

Mechanism of Action

Chlorobutanol's anesthetic mechanism involves inhibition of voltage-gated sodium channels (Na_v 1.2) at clinically relevant concentrations (0.03–10 mM), shifting the voltage dependence of activation and blocking channel function in a reversible, concentration-dependent way, thereby reducing generation and neuronal signaling. This contributes to its weak local anesthetic and sedative-hypnotic effects. The effects of chlorobutanol arise from suppression of neuronal excitability, limiting its clinical use as a standalone due to lower potency, shorter duration of action relative to related compounds like , and risk of accumulation from its prolonged . Despite these insights, the complete molecular pathways underlying chlorobutanol's effects remain incompletely elucidated as of 2025. Chlorobutanol also exhibits antiplatelet effects by inhibiting the pathway and negative inotropic effects on myocardial cells. In its role as a , chlorobutanol disrupts microbial cell membranes in a detergent-like by altering integrity, which increases permeability, causes leakage of intracellular contents, and ultimately results in cell . This action targets both and fungi without relying on properties, distinguishing it from other preservatives like . The efficacy occurs at low concentrations (typically 0.5%), making it suitable for pharmaceutical formulations such as injectables and ophthalmic solutions.

Pharmacokinetics

Chlorobutanol is rapidly absorbed following , with peak plasma concentrations of approximately 4–5 μg/mL achieved within 15 to 60 minutes after a 600 mg dose in healthy subjects. Limited data exist on topical absorption, but its use in topical formulations suggests potential systemic uptake, though specific metrics are not well-documented. The compound exhibits extensive distribution, characterized by a high of 233 ± 141 L, indicating broad tissue penetration beyond the plasma volume. It binds to plasma proteins at a level of 57 ± 3%, which may influence its free fraction available for pharmacological effects. of chlorobutanol primarily involves and sulfation, with urinary recovery showing 7.4% as these conjugates following oral dosing. Additionally, its chemical instability under physiological conditions contributes to elimination, with an half-life of 37 days at 7.4, suggesting spontaneous degradation plays a role alongside enzymatic processes. Excretion occurs mainly via the renal route, with a mean urinary recovery of 9.6% of the administered oral dose over 17 days, including 2.2% as unchanged drug. The terminal elimination is prolonged at 10.3 ± 1.3 days, accompanied by low plasma clearance of 11.6 ± 1.0 mL/min, which can lead to accumulation with repeated administration.

Toxicity and Safety

Human Health Risks

Chlorobutanol exhibits primarily through ingestion, with an oral LD50 of approximately 510 mg/kg in , indicating moderate hazard potential. The probable oral in humans is estimated at 50-500 mg/kg (approximately 3.5-35 g for a 70 kg adult). In experimental single-dose studies in , administration at 250 mg/kg body weight resulted in symptoms such as severe , dyspnea, and a moribund state in some animals, with one female observed approximately 2 days post-dose. As a contact irritant, chlorobutanol is a severe eye irritant, inducing in human corneal and conjunctival epithelial cells at concentrations as low as 0.1%, causing cell retraction, degeneration, swelling, and disruption of the epithelial barrier, which increases susceptibility to infections. exposure leads to and , classified as minimal to moderate in Draize assays, with prolonged contact exacerbating inflammatory responses. Overdose symptoms include , manifesting as , , and respiratory distress, alongside and potential -like effects due to its structural relation to and possible degradation products. Repeated exposure raises concerns for chronic , as evidenced by increased relative liver weight and fatty changes in female rats at 100 mg/kg body weight per day over 28 days, suggesting target organ damage with accumulation. Rare allergic reactions, such as redness, itching, and swelling, have been reported, particularly with topical ophthalmic use. Vulnerable populations include pregnant individuals, where embryotoxic effects were observed in cultured embryos, warranting caution to avoid accumulation; children under 2 years, due to heightened risk of in neonatal IV formulations; and users of eye products, where warnings emphasize potential.

Regulatory Considerations

Chlorobutanol is classified under the National Formulary (NF) and (USP) standards for use in pharmaceutical preparations, ensuring compliance with purity and quality requirements for excipients such as s in injectables, ophthalmic solutions, and topical formulations. In the , it is authorized as a in cosmetic products under Annex V of Regulation (EC) No 1223/2009, with a maximum concentration of 0.5% in ready-for-use preparations, but prohibited in dispensers such as sprays. Regulatory restrictions on chlorobutanol vary by application and , particularly for oral use. In the , it is not authorized as an in oral medicinal products due to effects and potential concerns, though it is permitted as an in non-oral formulations at levels below established safety thresholds; similar limitations apply in , where oral hygiene and lip care products are excluded from its use. In the United States, the FDA has approved chlorobutanol as a in multiple pharmaceutical products, including injectables and ophthalmic solutions, but it is not classified as (GRAS) for food additives and requires case-specific evaluation for oral applications to mitigate risks like irritation. Some countries, including those following strict EU-aligned standards, impose bans or severe limits on oral containing chlorobutanol as an , favoring alternatives due to historical reports of adverse effects. Labeling requirements for chlorobutanol emphasize its irritant properties under the Globally Harmonized System (GHS). Products must include warnings such as H319 (causes serious eye irritation), along with precautionary statements for handling, such as avoiding eye contact and using protective equipment; the outdated Xn (harmful) symbol from pre-GHS classifications has been replaced by GHS pictograms indicating (H302: harmful if swallowed) and skin/eye irritation (H315, H319). These labels ensure safe industrial and consumer handling, with additional notes on its potential to cause drowsiness. Recent regulatory updates have focused on safety in medicinal products. In 2021, the European Medicines Agency's (EMA) Safety Working Party reviewed chlorobutanol post-2011 assessments, establishing a Permitted Daily Exposure (PDE) of 0.5 mg/day for lifetime use based on data from rat studies, with higher short-term exposures (up to 1.2 mg/day) allowable on a case-by-case basis after benefit-risk evaluation; this reflects ongoing 2020s efforts to minimize cardiac risks like QT prolongation in intravenous formulations. The FDA continues to monitor its use in approved drugs without major changes as of November 2025, prioritizing preservative efficacy testing in stability studies. Internationally, chlorobutanol aligns with pharmacopeial standards like the but has not been directly included on the World Health Organization's (WHO) Model List of ; however, it has historically supported formulations of , such as stabilized oxytocin injectables, in resource-limited settings where its role aids stability without formal listing.

References

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