Циклобутансульфонилхлорид

Description

Cyclobutanesulfonyl chloride is the acid chloride of cyclobutanesulfonic acid. Belongs to the same class of cycloalkylsulfonyl chlorides as the cyclopentane analogue, but with a more strained four-membered ring; used as a sulfonylation reagent in fine organic synthesis.

Basic Attributes

• CAS No: 338453-16-0
• Chemical formula: C4H7ClO2S
• English name: Cyclobutane Sulfonyl chloride
• Synonyms: Cyclobutanesulfonyl chloride, Cyclobutylsulfonyl chloride
• Molecular weight: 154.62
• Exact weight: 153.985519 (153.9855283)
• DSSTox ID: DTXSID10627186
• HS code: 2904909090

Physico-chemical properties

• PSA: 42.5
• XLogP3: 1.17
• Density: 1.4±0.1 g/cm3
• Boiling point: 217 °C
• Flash point: 85 °C
• Refractive index: 1.506
• Number of hydrogen bond acceptors: 2; rotating links: 1

Danger

GHS classification: hazardous, H302 (100%) - harmful if swallowed. Precautions: P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501. GHS information provided by one company from one notification to the ECHA C&L Register.

Scope of application

Cyclobutanesulfonyl chloride, like its cyclopentane analogue, is used as a sulfonylation reagent: chlorine at the sulfur atom is easily replaced by amines and alcohols, giving sulfonamides and sulfonate esters of the cyclobutyl series. The four-membered ring has a noticeable angular strain, which distinguishes the properties of the resulting derivatives from larger cycloalkylsulfonamides and makes the compound a distinct building block in the development of biologically active molecules for pharmaceuticals and agrochemicals.

• reagent for the synthesis of sulfonamides of the cyclobutyl series
• raw materials for sulfonate esters
• building block of pharmaceutical and agrochemical chemistry

Storage and transportation

Store in an airtight container, away from moisture - the sulfonyl chloride group is hydrolyzed by water to release hydrogen chloride. Work with gloves and safety glasses; the substance is harmful if swallowed.

Place in the series of cycloalkylsulfonyl chlorides

Cyclobutanesulfonyl chloride opens a practical series of cycloalkylsulfonyl chlorides, continuing with cyclopentane and larger cyclohexyl analogues. The four-membered ring carries a noticeable angular strain, which is why the reagent is slightly different in reactivity from less strained homologues: under certain conditions, the cyclobutane ring is capable of participating in side opening reactions, which must be taken into account when selecting sulfonylation conditions and makes the substance a separate, independent building block, and not just a junior member of the series.

Comparison by physical properties

The boiling point of cyclobutanesulfonyl chloride (217 °C) is noticeably higher than that of the cyclopentane analogue (99 °C at a reduced pressure of 7 mmHg), which, when converted to normal pressure, reflects the higher polarity and molecular order of the strained four-membered ring in combination with the sulfonyl group.