Циклогексанацетилхлорид

Description

Cyclohexane acetyl chloride (2-cyclohexylacetyl chloride, cyclohexylacetic acid chloride) is a carboxylic acid chloride with a six-membered cyclohexane ring, CAS 23860-35-7, gross formula C8H13ClO. Like other acyl chlorides of the cycloaliphatic series, it is used in organic synthesis to introduce a cyclohexylacetyl fragment into target molecules. Prepared by chlorination of cyclohexylacetic acid with thionyl chloride, oxalyl chloride or phosphorus trichloride; completes the series of cycloalkylacetyl chlorides (cyclopropyl-, cyclopentyl-, cyclohexyl-), differing in ring size and, accordingly, in the lipophilicity of the resulting derivatives.

Basic Attributes

• CAS No.: 23860-35-7
• Chemical formula: C8H13ClO
• Molecular Weight: 160.643
• Exact weight: 160.64
• EU number: 607-279-3
• DSSTox ID: DTXSID20374114
• HS code: 2915900090
• PSA specifications: 17.07000
• XLogP3: 2.72220

Physico-chemical characteristics

• Density: 1.047 g/ml at 25 °C (according to literature data)
• Boiling point: 98–100 °C at 23 Torrent pressure
• Flash point: 178°F (81°C)
• Refractive index: 1.461

Scope of application

The reagent is used for the acylation of amines, alcohols and other nucleophiles to produce amides, esters and ketones containing a cyclohexylacetyl substituent. Such derivatives are in demand in pharmaceutical and agrochemical synthesis, where the cyclohexane ring sets the volumetric non-planar geometry of the side chain of the molecule and increases the lipophilicity of the compound (XLogP3 2.72 - higher than that of the cyclopropyl and cyclopentyl analogues). Reactions are carried out in the presence of an acceptor for the liberated hydrogen chloride (tertiary amine or aqueous alkali solution), controlling the temperature to minimize side hydrolysis of the reagent.

Safety Information

• Transport codes: UN 3265, 8/page. 3
• WGK Germany: 2
• Hazard class code: 22-34
• Safety instructions: 26-36/37/39-45
• Tags: C
• Precautionary Statement: P280-P305+P351+P338-P310
• Hazard statements: H302-H314 (harmful if swallowed, causes severe skin burns and eye damage)
• GHS classification: hazardous, H302 (100%) - acute oral toxicity warning; full list of GHS precautions: P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
• Aggregated information on the GHS was provided by 39 companies from 2 notifications and separately by 11 companies from 1 notification to the ECHA C&L Register

Storage and transportation conditions

The substance is hydrolyzed by water with the release of hydrogen chloride and cyclohexylacetic acid, therefore it is stored in a hermetically sealed container, in a dry, cool, well-ventilated area, away from water, bases and oxidizing agents. Transported as a corrosive substance (UN code 3265). When working, use a fume hood, acid-resistant gloves, eye and face protection; in case of contact with skin or eyes, immediately rinse with plenty of water. The spilled reagent is not washed off with a large volume of water - it is first neutralized with a dry sorbent, then treated with a weak alkali solution. The dual hazard classification (H302 and H314) reflects both toxicity if swallowed and severe corrosiveness to skin and mucous membranes, requiring more stringent protective measures than when working with less aggressive acyl chlorides of the same series.