2-Chloro-6-methylaniline
[CAS# 87-63-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 2-Chloro-6-methylaniline
• Synonyms: 2-Amino-3-chlorotoluene; 6-Chloro-o-toluidine
• Molecular Formula: C₇H₈ClN
• Molecular Weight: 141.60
• CAS Registry Number: 87-63-8
• EC Number: 201-759-2
• SMILES: CC1=C(C(=CC=C1)Cl)N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*, 1.152 g/mL (Expl.)
• Melting point: 10 - 12 °C (Expl.)
• Boiling point: 215.0 °C 760 mmHg (Calc.)^*, 215 °C (Expl.)
• Flash point: 98.9 °C (Calc.)^*, 105 °C (Expl.)
• Solubility: water: insoluble (Expl.)
• Index of refraction: 1.585 (Calc.)^*, 1.576 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H311-H312-H315-H319-H331-H332-H335-H341-H373
• Safety Statements: P203-P260-P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P317-P318-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	1	H370
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

• Transport Information: UN 2239; UN 3429

Discovery and Applications

2-Chloro-6-methylaniline is an aromatic amine compound characterized by a benzene ring substituted with a chlorine atom at the 2-position and a methyl group at the 6-position relative to the amino (-NH₂) group. Its molecular formula is C₇H₈ClN, reflecting its structure as a chlorinated methyl-substituted aniline derivative.

The compound was first identified and synthesized in the context of substituted aromatic amines, which are important intermediates in organic synthesis and industrial applications. 2-Chloro-6-methylaniline serves as a building block for the production of dyes, agrochemicals, pharmaceuticals, and polymers. Its synthesis typically involves selective chlorination and methylation of aniline or related precursors under controlled conditions to achieve the desired substitution pattern.

In organic synthesis, 2-chloro-6-methylaniline is valued for its reactivity due to the electron-donating amino group and the electron-withdrawing chlorine atom, which influence electrophilic and nucleophilic substitution reactions on the aromatic ring. This dual substitution pattern affects the compound’s chemical behavior, allowing for regioselective modifications and coupling reactions.

Applications of 2-chloro-6-methylaniline include its use as an intermediate in the manufacture of herbicides, fungicides, and insecticides, where it acts as a precursor for active molecules with pesticidal properties. In the pharmaceutical industry, derivatives of this compound are explored for their potential as pharmacophores in drug design, contributing to biological activities such as antimicrobial and anti-inflammatory effects.

Furthermore, 2-chloro-6-methylaniline is employed in the synthesis of azo dyes, where the amino group participates in diazotization reactions followed by azo coupling to form colored compounds used in textiles and inks. The presence of the chloro and methyl groups affects the hue, stability, and solubility of the resulting dyes.

Physicochemical properties of 2-chloro-6-methylaniline include moderate solubility in organic solvents and limited solubility in water. Its melting and boiling points, as well as spectral characteristics, have been well characterized using standard analytical techniques such as nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectrometry.

Safety considerations for handling 2-chloro-6-methylaniline involve precautions due to its potential toxicity and irritant properties common to aromatic amines. Appropriate protective measures are necessary during its synthesis, storage, and use to minimize exposure risks.

In summary, 2-chloro-6-methylaniline is an aromatic amine with chlorine and methyl substituents that influence its chemical reactivity and applications. Its role as an intermediate in the synthesis of dyes, agrochemicals, and pharmaceuticals underscores its significance in chemical manufacturing and research.

References

1988. The determination of substituted aromatic amines in water and sediment samples. Fresenius' Zeitschrift für analytische Chemie, 330(1).
DOI: 10.1007/bf00481897

1996. Use of incremental models to estimate the retention indexes of aromatic compounds. Chromatographia, 43(3-4).
DOI: 10.1007/bf02292946

2004. Testing a Flexible-receptor Docking Algorithm in a Model Binding Site. Journal of Molecular Biology, 337(5).
DOI: 10.1016/j.jmb.2004.02.015