35558-49-7

Basic information

• Product Name: BROMOCYCLOHEXANE-D11
• Synonyms: CYCLOHEXYL-D11 BROMIDE;BROMOCYCLOHEXANE-D11;CYCLOHEXYL-D11 BROMIDE, 98 ATOM % D;cyclohexyl bromide-d11
• CAS NO: 35558-49-7
• Molecular Formula: C₆H₁₁Br
• Molecular Weight: 174.12
• Mol File: 35558-49-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 166-167 °C(lit.)
• Flash Point: 145 °F
• Appearance: /
• Density: 1.412 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.492(lit.)
• CAS DataBase Reference: BROMOCYCLOHEXANE-D11(CAS DataBase Reference)
• NIST Chemistry Reference: BROMOCYCLOHEXANE-D11(35558-49-7)
• EPA Substance Registry System: BROMOCYCLOHEXANE-D11(35558-49-7)

Safety Data

• Statements: 52
• Safety Statements: 27-36/37/39
• RIDADR: UN 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 35558-49-7(Hazardous Substances Data)

Usage

Uses

Bromocyclohexane-d11 is used in the synthetic preparation and regioselective bromination of sp3 C-H bonds by organophotoredox catalysis.

Upstream product

• 1735-17-7 Cyclohexane-d12 

Downstream Products

• 1189190-98-4 d₁₆-cyclohexyl-phenyl-trimethylsilanyloxy-acetic acid methyl ester 

Relevant articles and documents

Site-Selective Aliphatic C-H Chlorination Using N-Chloroamides Enables a Synthesis of Chlorolissoclimide

Methods for the practical, intermolecular functionalization of aliphatic C-H bonds remain a paramount goal of organic synthesis. Free radical alkane chlorination is an important industrial process for the production of small molecule chloroalkanes from simple hydrocarbons, yet applications to fine chemical synthesis are rare. Herein, we report a site-selective chlorination of aliphatic C-H bonds using readily available N-chloroamides and apply this transformation to a synthesis of chlorolissoclimide, a potently cytotoxic labdane diterpenoid. These reactions deliver alkyl chlorides in useful chemical yields with substrate as the limiting reagent. Notably, this approach tolerates substrate unsaturation that normally poses major challenges in chemoselective, aliphatic C-H functionalization. The sterically and electronically dictated site selectivities of the C-H chlorination are among the most selective alkane functionalizations known, providing a unique tool for chemical synthesis. The short synthesis of chlorolissoclimide features a high yielding, gram-scale radical C-H chlorination of sclareolide and a three-step/two-pot process for the introduction of the β-hydroxysuccinimide that is salient to all the lissoclimides and haterumaimides. Preliminary assays indicate that chlorolissoclimide and analogues are moderately active against aggressive melanoma and prostate cancer cell lines.

On the Mechanism of Carbon-Hydrogen Activation in Gif-type Reactions. Kinetic Isotopic Effects in Pyridine Solution.

Kinetic isotopic effects (KIE) were measured for oxidation, bromination and selenylation of c-C6H12/c-C6D12 in pyridine solution for different Gif-type, Fenton and other systems.The comparison of KIE and relative reactivity data for the pair c-C5H10/c-C6H12 proved that the mechanism of activation in Gif-type reactions is different from a hydrogen atom abstraction.