2-Chlorobenzyl chloride
[CAS# 611-19-8]

Identification

• Classification: Chemical pesticide >> Herbicide >> Herbicide intermediate
• Name: 2-Chlorobenzyl chloride
• Synonyms: 1-Chloro-2-(chloromethyl)-benzene; OCBC
• Molecular Formula: C₇H₆Cl₂
• Molecular Weight: 161.03
• CAS Registry Number: 611-19-8
• EC Number: 210-258-8
• SMILES: Clc1ccccc1CBr

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*, 1.272 g/mL (Expl.)
• Melting point: -13 ºC (Expl.)
• Boiling point: 213.7±15.0 ºC 760 mmHg (Calc.)^*, 213 - 214 ºC (Expl.)
• Flash point: 82.2 ºC (Calc.)^*, 109 ºC (Expl.)
• Index of refraction: 1.547 (Calc.)^*, 1.559 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H227-H314-H317-H335-H410-H302+H312+H332
• Precautionary Statements: P210-P264-P270-P271-P272-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P370+P378-P362+P364-P403+P233-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	4	H332
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H336
Flammable liquids	Flam. Liq.	4	H227
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 2235

Discovory and Applicatios

2-Chlorobenzyl chloride is an organic compound with the chemical formula C7H6Cl2, consisting of a benzene ring with a chlorine atom attached to the benzyl group at the 2-position (relative to the benzyl group). It is a halogenated aromatic compound, and the presence of both chlorine atoms on the benzene ring and the benzyl group makes it a useful intermediate in various organic reactions.

The synthesis of 2-chlorobenzyl chloride is typically carried out by the chlorination of 2-chlorotoluene, where the methyl group in toluene is replaced by a chlorine atom in the presence of chlorine gas (Cl2) or other chlorinating agents such as phosphorus trichloride (PCl3) or thionyl chloride (SOCl2). This chlorination reaction usually proceeds via an electrophilic aromatic substitution mechanism, where the chlorine atom substitutes a hydrogen atom in the methyl group, yielding the desired 2-chlorobenzyl chloride product.

2-Chlorobenzyl chloride is widely used in organic synthesis, particularly in the production of various pharmaceuticals, agrochemicals, and functional materials. The compound's ability to undergo nucleophilic substitution reactions makes it a versatile intermediate in the synthesis of many important chemicals.

In pharmaceutical research, 2-chlorobenzyl chloride is used as a building block in the preparation of various bioactive compounds. Its reactivity in nucleophilic substitution reactions allows for the attachment of a wide range of functional groups to the benzyl position. This makes it valuable for designing compounds with antimicrobial, anticancer, or anti-inflammatory properties. It can also be used in the synthesis of benzylated derivatives, which are important in medicinal chemistry.

Moreover, 2-chlorobenzyl chloride is utilized in the synthesis of dyes and other organic materials. The chlorine atom on the benzyl group can participate in cross-coupling reactions with various nucleophiles, enabling the creation of a wide range of organic compounds with desired properties. These compounds can be applied in the production of polymeric materials, liquid crystals, or conductive materials for electronic applications.

In addition, 2-chlorobenzyl chloride can be employed in the development of agrochemicals, such as herbicides or insecticides. By modifying the benzyl group with different functional groups, compounds with specific activity can be synthesized, contributing to the agricultural industry's need for effective chemical agents.

Despite its usefulness, 2-chlorobenzyl chloride should be handled with care due to the potential health hazards associated with chlorinated organic compounds. It can be irritating to the skin, eyes, and respiratory system upon exposure, and long-term exposure to such compounds may have adverse health effects. Proper safety protocols should be followed, including the use of gloves, goggles, and ventilation equipment to minimize exposure.

In summary, 2-chlorobenzyl chloride is an important intermediate in organic synthesis with applications in pharmaceuticals, agrochemicals, materials science, and dye production. Its ability to undergo nucleophilic substitution reactions allows for the synthesis of a wide variety of useful compounds. However, it should be handled with caution to avoid health and environmental risks associated with its use.

References

1977. Anisotropy of polarizability and conformation of substituted benzyl chlorides. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 26(3).
DOI: 10.1007/bf01179462

2009. Large-Scale Preparation of Polyfunctional Benzylic Zinc Reagents by Direct Insertion of Zinc Dust into Benzylic Chlorides in the Presence of Lithium Chloride. Synthesis, 2009(22).
DOI: 10.1055/s-0029-1217134

2011. Synthesis, Crystal and Molecular Structure of 1-(2-Chlorobenzyl)-2-methylthio-1H-benzimidazole. Journal of Chemical Crystallography, 41(6).
DOI: 10.1007/s10870-011-9990-0