Циклогексанацетилхлорид

Description

Cyclohexane acetyl chloride (2-cyclohexylacetyl chloride) is the acid chloride of cyclohexylacetic acid, completing the typical series of cycloalkylacetic acyl chlorides after the cyclopropyl, cyclobutyl and cyclopentyl members. Belongs to the class of aliphatic acyl chlorides with a saturated six-membered ring in the side chain.

Basic Attributes

• CAS No.: 23860-35-7
• Chemical formula: C8H13ClO
• English name: Cyclohexane Acetyl chloride
• Synonyms: 2-Cyclohexylacetyl chloride, Cyclohexylacetyl chloride, Cyclohexylacetic acid chloride
• Molecular weight: 160.643
• Exact weight: 160.64 (160.0654927)
• EU number: 607-279-3
• DSSTox ID: DTXSID20374114
• HS code: 2915900090

Physico-chemical properties

• PSA: 17.07
• XLogP3: 2.7222 (according to other sources 3.4)
• Density: 1.047 g/ml at 25 °C
• Boiling point: 98–100 °C at 23 mmHg. Art. (Torr)
• Flash point: 178°F (81.1°C)
• Refractive index: 1.461
• Number of hydrogen bond acceptors: 1; rotating links: 2
• Number of heavy atoms: 10; difficulty 116

Danger and transportation

• Transport codes: UN 3265, 8/PG 3
• WGK Germany: 2
• Hazard class code: 22-34
• Safety instructions: 26-36/37/39-45
• Mark: C
• Hazard Statements: H302-H314 - Harmful if swallowed, causes severe skin burns and eye damage
• 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 based on 2 notifications to the ECHA C&L Register, as well as separately by 11 companies from 1 notification.

Scope of application

Cyclohexane acetyl chloride completes the homologous series of cycloalkylacetic acyl chlorides and, like its other members, is used as an acylation reagent in the synthesis of pharmaceutical substances and agrochemicals: chlorine at the carbonyl atom is easily replaced by alcohols, amines and thiols. A more voluminous six-membered ring compared to the cyclopropyl and cyclopentyl analogues gives the resulting molecules increased lipophilicity, which is taken into account when selecting the structure of the active substance for the required solubility and permeability profile.

• acylating reagent for esters, amides, thioesters
• medicinal chemistry building block with cyclohexyl moiety
• raw materials for agrochemical products

Storage and transportation

Store in an airtight container, away from moisture and water - the substance causes severe skin burns and eye damage, and is harmful if swallowed. Work with gloves, safety glasses, and ventilation. Transportation - hazard class 8 cargo, UN number 3265, packing group III.

Place in the series of cycloalkylacetic acyl chlorides

Cyclohexane acetyl chloride is the largest and least strained member of the series of cycloalkylacetic acyl chlorides, beginning with cyclopropylacetyl chloride. The six-membered ring in the chair conformation does not create angular stress, so the reagent behaves like a standard aliphatic acyl chloride, and its use in the synthesis produces molecules with the highest lipophilicity among the entire homologous series.