2-Chloro-6-nitrotoluene
[CAS# 83-42-1]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 2-Chloro-6-nitrotoluene
• Synonyms: 1-Chloro-2-methyl-3-nitrobenzene
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• CAS Registry Number: 83-42-1
• EC Number: 201-475-9
• SMILES: CC1=C(C=CC=C1Cl)[N+](=O)[O-]

Properties

• Melting point: 33-37 °C
• Boiling point: 238 °C
• Flash point: 125 °C
• Water solubility: 92 mg/L (20 °C)

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H302-H315-H319-H335-H373-H411
• Safety Statements: P260-P264-P264+P265-P270-P273-P280-P301+P317-P302+P352-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 2433; UN 3457

Discovery and Applications

2-Chloro-6-nitrotoluene is an aromatic compound with the chemical formula C7H6ClNO2. Structurally, it consists of a toluene ring substituted with a chlorine atom at the 2-position and a nitro group at the 6-position. This configuration imparts distinct chemical properties to the molecule, making it a valuable intermediate in various industrial applications. Its discovery and development as a chemical substance were driven by the need to synthesize complex aromatic compounds used in dye, pharmaceutical, and agrochemical industries.

The compound can be synthesized through the nitration of 2-chlorotoluene, a reaction that introduces the nitro group into the aromatic ring. Nitration typically involves the use of concentrated nitric and sulfuric acids under controlled conditions. The resulting product, 2-chloro-6-nitrotoluene, is isolated and purified for further use.

2-Chloro-6-nitrotoluene is primarily used as an intermediate in the synthesis of various chemicals. In the dye industry, it serves as a key precursor for the production of azo dyes and pigments. The nitro and chloro substituents on the aromatic ring make it reactive towards further chemical modifications, such as reduction or substitution reactions, allowing for the creation of a wide range of colorants used in textiles and plastics.

In the pharmaceutical industry, 2-chloro-6-nitrotoluene is employed in the synthesis of active pharmaceutical ingredients (APIs). The presence of both nitro and chloro groups enables selective reactions, making it a useful building block for producing drugs with specific chemical functionalities. Additionally, it can be used in the development of agrochemicals, where its reactive structure allows for the production of herbicides, insecticides, and fungicides.

Despite its usefulness, 2-chloro-6-nitrotoluene must be handled with care, as it is classified as a hazardous material. The compound can be harmful if inhaled, ingested, or if it comes into contact with skin. Prolonged exposure can lead to irritation or more severe health issues, necessitating appropriate safety measures in industrial settings.

Overall, the discovery and application of 2-chloro-6-nitrotoluene have had a significant impact on multiple industries. Its role as a versatile intermediate in the synthesis of dyes, pharmaceuticals, and agrochemicals underscores its importance in chemical manufacturing.

References

2002. Molecular Characterization and Substrate Specificity of Nitrobenzene Dioxygenase from Comamonas sp. Strain JS765. Applied and Environmental Microbiology, 68(2).
DOI: 10.1128/aem.68.2.634-641.2002

2011. 1-Chloro-2-methyl-3-nitro-benzene. Acta crystallographica. Section E, Structure reports online, 67(Pt 3).
DOI: 10.1107/s1600536811004466

2021. The application of modern reactions in large-scale synthesis. Nature reviews. Chemistry, 5(6).
DOI: 10.1038/s41570-021-00288-z