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2,3-Dimethylpentane
2,3-Dimethylpentane
2,3-Dimethylpentane
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2,3-Dimethylpentane
Skeletal formula of 2,3-dimethylpentane
Names
Preferred IUPAC name
2,3-Dimethylpentane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.437 Edit this at Wikidata
EC Number
  • (racemic): 209-280-0
UNII
UN number 1206
  • InChI=1S/C7H16/c1-5-7(4)6(2)3/h6-7H,5H2,1-4H3/t7-/m0/s1 checkY
    Key: WGECXQBGLLYSFP-UHFFFAOYSA-N checkY
  • (racemic): CCC(C)C(C)C
Properties
C7H16
Molar mass 100.205 g·mol−1
Appearance Colourless liquid
Density 0.7076 g/mL (25 °C), 0.6413 (80 °C), 0.7380 (25 °C, 45 MPa), 0.6891 (80 °C, 45 MPa) (racemic)[1]
Boiling point 89.7 °C (racemic)[2][3][4]
Vapor pressure 2.35 psi (37.7 °C)[5]
Viscosity 0.356 mPa s (30 °C), 0.232 (80 °C), 0.624 (30 °C, 60 MPa) (racemic)[1]
Thermochemistry
34.308 cal/K/mol (−189 °C), 51.647 (20 °C), 58.735 (86.6 °C) (racemic)[6]
71.02 cal/K/mol (25 °C) (racemic)[6]
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Danger
H225, H304, H315, H335, H336, H410
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P312, P321, P331, P332+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point −7 °C (19 °F; 266 K)[5]
337 °C (639 °F; 610 K)[5]
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,3-Dimethylpentane is an organic compound of carbon and hydrogen with formula C
7H
16, more precisely CH
3–CH(CH
3)–CH(CH
3)–CH
2–CH
3: a molecule of pentane with methyl groups –CH
3 replacing hydrogen atoms on carbon atoms 2 and 3. It is an alkane ("paraffin" in older nomenclature), a fully saturated hydrocarbon; specifically, one of the isomers of heptane.

Like typical alkanes, it is a colorless flammable compound; under common ambient conditions, it is a mobile liquid, less dense than water.[1]

2,3-Dimethylpentane is notable for being one of the two simplest alkanes with optical (enantiomeric) isomerism. The optical center is the middle carbon of the pentane backbone, which is connected to one hydrogen atom, one methyl group, one ethyl group –C
2H
5, and one isopropyl group –CH(CH
3)
2. The two enantiomers are denoted (3R)-2,3-dimethylpentane and (3S)-2,3-dimethylpentane (the other simplest chiral alkane is its structural isomer 3-methylhexane).

Properties

[edit]

Most properties listed in the literature refer to the racemic compound (an equimolar mixture of the two enantiomers).

The boiling point of 89.7 °C is 0.3 °C higher than the value of 89.4 °C predicted by Wiener's formula, based on the structure of the molecule and the boiling point of n-heptane.[2][3]

The speed of sound at 3 MHz is 1149.5 m/s at 20 °C and 889.5 m/s at 80 °C.[7][8][9]

The racemic mixture has a glass transition temperature of about 123 K (−150 °C), but reportedly it does not crystallize—a fact that has been claimed to be a characteristic of high-purity optically active alkanes.[4][6][10]

Preparation

[edit]

2,3-Dimethylpentane is practically absent in the synthetic fuel produced from hydrogen and carbon monoxide by the Fischer–Tropsch process.[11]

The pure compound can be prepared by reacting the Grignard reagent sec-butyl magnesium bromide C
4H
9–MgBr with acetone to form 2,3-dimethyl-2-pentanol, then dehydrating this alcohol to form 2,3-dimethyl-2-pentene, and hydrogenating this product.[4]

The isomer is present at about 2.4% by weight in the hydrocarbon mixture obtained by the condensation of methanol at 200 °C with a zinc iodide catalyst (the main component of the mixture being the isomer 2,2,3-trimethylbutane, obtained at almost 50% yield).[12]

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

2,3-Dimethylpentane

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from Grokipedia
2,3-Dimethylpentane is a branched and one of the nine isomers of , with the molecular formula C₇H₁₆ and a of 100.20 g/mol. Its IUPAC name is 2,3-dimethylpentane (CAS 565-59-3), and it features a five-carbon chain with methyl substituents at the 2- and 3-positions, giving the CH₃CH(CH₃)CH(CH₃)CH₂CH₃. This compound has two chiral centers at carbons 2 and 3, resulting in stereoisomers including (2R,3R)- and (2R,3S)-forms, and it is classified as a saturated with no functional groups beyond the backbone. Physically, 2,3-dimethylpentane is a colorless liquid at room temperature, with a reported boiling point of 89–90 °C and a melting point of approximately -130 °C. Its density is 0.695 g/mL at 25 °C, and it has a vapor pressure of 55 mm Hg at 20 °C, with a vapor density of 3.45 relative to air. These properties make it volatile and flammable, consistent with other heptane isomers, and it exhibits low solubility in water but good miscibility with organic solvents. In terms of applications, 2,3-dimethylpentane is primarily utilized as a in chemical processes and is a component of formulations due to its presence among isomers in -derived fuels. It also finds use in research settings, such as studies on physical constants for branched alkanes. Additionally, it serves as a reference standard in fuel-related analyses and chemical syntheses, leveraging its well-characterized properties. The compound's production typically involves catalytic processes from petroleum fractions or synthetic routes, though it is commercially available from suppliers for laboratory and industrial needs. Safety considerations include its high flammability, requiring handling in well-ventilated areas with explosion-proof equipment.

Introduction

Overview

2,3-Dimethylpentane is a saturated and one of the nine constitutional isomers of , with the molecular formula C₇H₁₆ and CH₃CH(CH₃)CH(CH₃)CH₂CH₃. As a branched , it features methyl groups attached to the second and third carbon atoms of a backbone, resulting in a compact molecular structure typical of isoalkanes found in . This was identified during early 20th-century investigations into the composition of distillates, where isomers were separated and characterized from narrow-boiling fractions of crude oil. Such studies, conducted amid the rise of the , aimed to understand the chemical makeup of components and their impact on performance. In and , 2,3-dimethylpentane serves as a representative model for branched alkanes, aiding investigations into kinetics, bond dissociation energies, and ratings in surrogate fuels. Its chiral centers at positions 2 and 3 contribute to stereochemical complexity, while physical properties like a of 90 °C highlight its volatility suitable for solvent and applications.

Nomenclature and isomers

2,3-Dimethylpentane receives its IUPAC name from the parent of five carbon atoms () with methyl groups substituted at the 2 and 3 positions; the chain is numbered from the end that assigns the lowest locants to the substituents. This compound is one of nine constitutional isomers of , all sharing the molecular formula C₇H₁₆ but differing in carbon skeleton connectivity. Constitutional isomers like these exhibit chain isomerism, where the branching patterns vary while maintaining the same overall atom count and types, unlike stereoisomers that possess identical connectivity but differ in spatial configuration. In comparison, 2,3-Dimethylpentane has methyl branches on adjacent carbons of the pentane chain, setting it apart from the unbranched n-heptane or singly branched 2-methylhexane, which features one methyl group on a six-carbon chain. The full set of isomers highlights diverse branching, from linear to highly substituted structures.
Isomer NameBranching Pattern
n-HeptaneStraight chain of seven carbons
2-MethylhexaneHexane chain with one methyl at position 2
3-MethylhexaneHexane chain with one methyl at position 3
2,2-DimethylpentanePentane chain with two methyls at position 2
2,3-DimethylpentanePentane chain with methyls at positions 2 and 3
2,4-DimethylpentanePentane chain with methyls at positions 2 and 4
3,3-DimethylpentanePentane chain with two methyls at position 3
3-EthylpentanePentane chain with one ethyl at position 3
2,2,3-TrimethylbutaneButane chain with two methyls at position 2 and one at position 3

Chemical structure

Molecular formula and bonding

2,3-Dimethylpentane has the molecular formula C₇H₁₆, consistent with the general formula for alkanes CₙH₂ₙ₊₂ where n=7, and a of 100.20 g/mol. This composition reflects its classification as a saturated , containing only carbon and atoms in a fully saturated structure. The molecule features a branched carbon consisting of a five-carbon chain () with additional methyl groups attached to the second and third carbon atoms, as indicated by its IUPAC name. All bonds in 2,3-Dimethylpentane are single (σ) bonds formed by the overlap of atomic orbitals between carbon-carbon (C-C) and carbon- (C-H) pairs, with no double or triple bonds present. Each of the seven carbon atoms exhibits sp³ hybridization, where one 2s and three 2p orbitals combine to form four equivalent sp³ hybrid orbitals arranged in a tetrahedral around each carbon, with ideal bond angles of 109.5°. This hybridization ensures that every carbon achieves a stable octet through four bonds. The of 2,3-Dimethylpentane depicts the carbon framework as a zigzag chain of five carbons, with short lines branching off the second and third carbons to represent the methyl groups, omitting the atoms for simplicity. In contrast, the full explicitly shows all atoms: the central chain as C-C-C-C-C, with methyl branches (each a C atom bonded to three H atoms) at positions 2 and 3, and terminal methyl groups at both ends; each carbon is bonded to the appropriate number of s to satisfy valence (e.g., the branched carbons each bond to one H, while chain-end carbons bond to three H). This representation highlights the covalent bonding network without lone pairs, as the is nonpolar and hydrocarbon-based.

Stereochemistry

2,3-Dimethylpentane features a single chiral center at the third carbon atom, which is bonded to four distinct groups: a hydrogen atom, a methyl group, an ethyl group (-CH₂CH₃), and a 1-methylethyl group (-CH(CH₃)CH₃). This asymmetry results in two non-superimposable mirror-image enantiomers designated as (3R)-2,3-dimethylpentane and (3S)-2,3-dimethylpentane. The , consisting of equal proportions of the (3R) and (3S) enantiomers, exhibits no optical activity due to the cancellation of rotations from the individual components, whereas the pure enantiomers are optically active with specific rotations of opposite sign and equal magnitude. Physical properties such as are identical for the and the pure enantiomers; for example, the is 0.695 g/mL at 25 °C. The does not crystallize upon cooling because it undergoes a at approximately 123 , forming an rather than a crystalline phase.

Physical properties

Thermodynamic data

2,3-Dimethylpentane exhibits a normal of 89.7 °C at standard for the . Due to its inability to crystallize readily, 2,3-Dimethylpentane lacks a conventional and instead undergoes a at approximately 123 K (-150 °C), with thermodynamic properties reported for the amorphous glass and phases. The of the is 0.695 g/mL at 25 °C. Additional thermodynamic indicators include a of -6 °C, indicating high flammability, and an of 337 °C. The is 2.35 psi at 37.7 °C, reflecting moderate volatility consistent with its status. The is approximately 34.3 kJ/mol near the .
PropertyValueConditionsSource
Boiling point89.7 °C1 atmNIST WebBook
Density0.695 g/mL25 °CSigma-Aldrich
Flash point-6 °C-Thermo Fisher SDS
Autoignition temperature337 °C-Sigma-Aldrich
Vapor pressure2.35 psi37.7 °CSigma-Aldrich
Enthalpy of vaporization34.3 kJ/molNear boiling pointNIST WebBook

Optical and acoustic properties

2,3-Dimethylpentane is a colorless liquid with a gasoline-like . It is insoluble in , consistent with its nonpolar nature. The of 2,3-dimethylpentane is 1.392 at 20 °C (n20/D). This value indicates moderate light-bending capability, typical for branched alkanes of similar molecular weight. The in liquid 2,3-dimethylpentane is 1149.5 m/s at 20 °C and 3 MHz under . Measurements were conducted via ultrasonic methods.

Chemical properties

General reactivity

As a branched , 2,3-dimethylpentane exhibits the typical low reactivity characteristic of hydrocarbons in this class, remaining largely inert under standard conditions due to the high bond dissociation energies of its C-C (approximately 350 kJ/mol) and C-H (approximately 410 kJ/mol) bonds, which resist heterolytic cleavage by most . This stability extends to non-reactivity with strong acids, bases, or nucleophiles at ambient temperatures and pressures, as alkanes lack functional groups susceptible to such interactions. However, the molecule's branched structure influences its overall reactivity profile compared to linear n-heptane; for instance, branching leads to a lower (indicating greater thermodynamic stability) and reduced susceptibility to autoignition, with 2,3-dimethylpentane showing slower oxidation rates in environments. The primary reactive pathway under forcing conditions is complete in the presence of oxygen, yielding and according to the balanced : C7H16+11O2→7CO2+8H2O\mathrm{C_7H_{16} + 11O_2 \rightarrow 7CO_2 + 8H_2O} This releases approximately 4808 kJ/mol and is utilized in applications, though the branched burns with slightly less energy output than n-heptane due to its higher molecular stability. Another key reaction involves free radical substitution with halogens such as or , initiated by ultraviolet light or , where a is replaced by a to form alkyl halides; for 2,3-dimethylpentane, this yields multiple monohalo products due to the presence of primary, secondary, and tertiary hydrogens at distinct positions. The compound is incompatible with strong oxidizing agents like peroxides, permanganates, or , potentially leading to violent reactions or explosions upon contact. Overall, its reactivity rating is minimal (NFPA 0), underscoring its chemical inertness except under specific initiation.

Spectroscopic characteristics

Nuclear magnetic resonance (NMR) spectroscopy is a primary method for characterizing 2,3-dimethylpentane, revealing its branched structure through distinct proton and carbon environments. In the ¹H NMR , the methyl protons appear as signals around 0.85–1.0 ppm: the terminal CH₃CH₂ group as a triplet at ~0.9 ppm (3H), while the CH₃ at C1 and the branched methyl groups at C2 and C3 appear as doublets near 0.9–1.0 ppm (total 9H). The methylene protons resonate as a multiplet around 1.3 ppm (2H), and the methine protons at C2 and C3 as multiplets near 1.5 ppm (2H), with the overall showing multiple overlapping signals (up to 7 in high resolution) due to the chiral centers causing diastereotopic distinctions. These shifts are typical for aliphatic hydrocarbons, measured in CDCl₃ solvent at standard frequencies like 400 MHz. The ¹³C NMR spectrum of 2,3-dimethylpentane displays seven distinct signals, confirming seven unique carbon environments due to the lack of in the branched chain. Terminal methyl carbons (C1 and C5 equivalents) resonate at ~8–10 ppm, the branched methyl groups at C2 and C3 around 18–20 ppm, the methine carbons (C2 and C3) at 27–30 ppm, and the methylene carbon (C4) at ~36–38 ppm, with measurements typically conducted in CDCl₃ at 100 MHz or higher. This multiplicity distinguishes it from more symmetric heptane isomers like 2,4-dimethylpentane, which show fewer signals. Infrared (IR) spectroscopy of 2,3-dimethylpentane exhibits characteristic absorptions for saturated alkanes, with strong C-H stretching bands in the 2850–2960 cm⁻¹ region arising from symmetric and asymmetric stretches of sp³-hybridized C-H bonds. Additional features include weak C-H bending deformations around 1465 cm⁻¹ and C-C skeletal vibrations below 1300 cm⁻¹, but no peaks indicative of functional groups beyond hydrocarbons, as confirmed in gas-phase spectra. Mass spectrometry (MS) under provides identification via the molecular ion at m/z 100 ([C₇H₁₆]⁺•), with a low-intensity peak due to the stability of alkanes. Prominent fragmentation includes loss of a methyl radical yielding m/z 85 ([C₆H₁₃]⁺), and further cleavages producing abundant ions at m/z 57 ([C₄H₉]⁺, likely from isopropyl-like fragments) and m/z 43 ([C₃H₇]⁺, propyl cation), reflecting preferential breaks at branched sites to form stable carbocations; the base peak is often at m/z 43.

Synthesis and production

Laboratory methods

One common laboratory method for synthesizing 2,3-dimethylpentane involves a multi-step sequence. The process begins with the preparation of sec-butylmagnesium bromide from sec-butyl bromide and magnesium in anhydrous under an inert atmosphere, typically , to avoid quenching by moisture or oxygen. This is then added to acetone at low temperature (around 0°C) to form the tertiary alcohol 2,3-dimethylpentan-2-ol after acidic . The alcohol is subsequently dehydrated using an acid catalyst such as or at elevated temperature (100–150°C) to yield the 2,3-dimethylpent-2-ene. Finally, the is hydrogenated over a or catalyst under mild conditions (, 1–3 atm H₂) to produce 2,3-dimethylpentane. This method provides a stereoselective route when starting from chiral precursors, though racemic product is typical without resolution. The reaction requires strict conditions and inert atmosphere throughout to maintain integrity.

Industrial sources

2,3-Dimethylpentane is primarily sourced industrially from the of during refining, where it occurs as a component of the boiling range fractions. Analysis of representative crude oils shows it comprising approximately 1–2% by volume in the paraffin-naphthene portion of these fractions across various sources, such as Ponca () crude at 1.42% and crude at 1.43%. In the overall distillate (40–160°C), concentrations range from 1.04% in Ponca crude to 2.36% in Conroe () crude, averaging around 1.7%. This branched alkane is notably absent from synthetic fuels generated by the , which converts and into predominantly linear hydrocarbons. Studies of C7 isomers in such products indicate 2,3-dimethylpentane at only 0.9 vol% of the hydrogenated fraction, far lower than in natural -derived . Commercial-grade 2,3-dimethylpentane, identified by CAS number 565-59-3, is purified via from heptane isomer mixtures derived from petroleum fractions. This involves azeotropic distillation with using high-efficiency columns (e.g., 130 theoretical plates) under controlled pressure (725 mm Hg) and reflux ratios to achieve high purity levels exceeding 99 mole%.

Applications and occurrence

Industrial uses

2,3-Dimethylpentane serves as a component in formulations, where its branched structure contributes to an improved research octane number (RON) of approximately 91.1 in blends, helping to enhance overall fuel performance and reduce . As one of the isomers present in petroleum-derived fuels, it is incorporated into to boost ratings without significantly altering other combustion properties. In chemical , particularly for rubber production, 2,3-Dimethylpentane functions as a low-polarity effective for dissolving polymers and facilitating processing steps such as mixing and coating. Its non-polar nature allows it to interact well with -based materials, making it suitable for applications in rubber solvent mixtures. Additionally, 2,3-Dimethylpentane is employed as an analytical standard in (GC) techniques for calibrating hydrocarbon separations, particularly in environmental and fuel analysis. It provides a reference peak for identifying and quantifying similar alkanes in samples like ambient air via thermal desorption-GC/MS or in via GC-FID, ensuring accurate retention time and determinations.

Natural occurrence

2,3-Dimethylpentane is a minor constituent in crude , where it occurs as part of the light fraction, with concentrations up to 4.37 wt% in cuts from specific oils like Frade crude (e.g., 0.39 wt% in the 212-302°F fraction). It is also present in deposits, contributing to the light composition used in geochemical analyses to assess maturity and origin. This compound serves as a bacterial , produced by microbial communities under anaerobic conditions in biogenic gas reservoirs, where it forms part of the isoalkane profile generated through bacterial degradation of . Trace amounts of 2,3-Dimethylpentane have been detected in volatiles and essential oils, such as those from species during early domestication stages, though it constitutes a small fraction (e.g., up to 4.76% in some samples) compared to dominant straight-chain alkanes. Similar minor occurrences appear in root exudates and leaf emissions of other s like olives under stress conditions.

Safety and environmental aspects

Health and safety hazards

2,3-Dimethylpentane is a highly with a of -7 °C, posing a significant and hazard when exposed to ignition sources such as heat, sparks, or open flames. Vapors can form explosive mixtures with air, necessitating the use of , non-sparking tools, and proper grounding of containers during handling to prevent static discharge. Exposure to 2,3-Dimethylpentane can cause to the skin and eyes upon contact, leading to redness, discomfort, and potential with prolonged exposure. Inhalation of vapors may result in effects, including , , and drowsiness, while ingestion poses an aspiration hazard that could lead to or pulmonary failure. Acute oral toxicity is low (LD50 > 2 g/kg in rats, estimated from analogous isomers), similar to other isomers. Safe handling requires the use of (PPE), including chemical-resistant gloves, safety goggles, and protective clothing, along with adequate ventilation to minimize inhalation risks. Under the Globally Harmonized System (GHS), it is classified as a (Category 2), skin irritant (Category 2), specific target organ toxicant (Category 3, ), and aspiration hazard (Category 1). Storage should occur in a cool, well-ventilated area away from incompatible materials, and spills must be contained and cleaned up using non-sparking tools to avoid ignition.

Environmental impact

2,3-Dimethylpentane demonstrates good biodegradability in environmental compartments such as and , where it serves as a sole carbon source for acclimated microbial communities under aerobic conditions. Research using porous pot reactors has shown that mixed microbial from gasoline-polluted sites can effectively degrade it, with biodegradation rates enhanced by the presence of electron acceptors like or in less agitated simulations. This indicates its potential for natural attenuation in contaminated , though rates may vary based on microbial acclimation and environmental factors. The compound exhibits low bioaccumulation potential in aquatic organisms, attributed to its estimated (log Kow) of approximately 3.6–3.8, similar to related C7 alkylates, which corresponds to a factor (BCF) below 100. Safety assessments for analogous branched pentanes confirm minimal uptake in and due to this moderate hydrophobicity, reducing risks of trophic magnification in webs. However, spills can lead to , as evidenced by detections in petroleum-impacted aquifers at concentrations up to several μg/L, necessitating remediation to prevent long-term plume migration. Regarding aquatic toxicity, 2,3-Dimethylpentane is classified under GHS as very toxic to aquatic with long-lasting effects, with estimated 96-hour LC50 values for around 0.1–2.2 mg/L based on quantitative structure-activity relationship (QSAR) models and read-across from similar alkanes. These values suggest acute risks to sensitive species like at low concentrations, though its low water solubility (approximately 5 mg/L at 25 °C) limits exposure in practice. It is regulated as a (VOC) in air quality standards by the U.S. EPA and directives, subject to emission controls in ozone non-attainment areas, but its minimal formation potential—quantified by a maximum incremental reactivity () of 1.31 g O3/g VOC—results in negligible contribution to tropospheric compared to more reactive alkenes or aromatics.

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