81861-58-7

Basic information

• Product Name: 8Z-heptadecenyl bromide
• CAS NO: 81861-58-7
• Molecular Formula: C₁₇H₃₃Br
• Molecular Weight: 317.35
• Mol File: 81861-58-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 8Z-heptadecenyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 8Z-heptadecenyl bromide(81861-58-7)
• EPA Substance Registry System: 8Z-heptadecenyl bromide(81861-58-7)

Safety Data

• Hazardous Substances Data: 81861-58-7(Hazardous Substances Data)

Usage

General Description

8Z-heptadecenyl bromide is a chemical compound with the molecular formula C17H33Br. It is a long-chain alkyl bromide, consisting of a heptadecene group with a double bond at the 8th carbon position and a bromine atom attached to one of the carbons in the alkyl chain. 8Z-heptadecenyl bromide is commonly used in organic synthesis as a reagent for creating carbon-carbon bonds and as an intermediate in the production of various organic compounds. It is also used as a starting material for the synthesis of complex molecules in the field of pharmaceuticals and agrochemicals, making it an important building block in the chemical industry.

Upstream product

• 55110-76-4 (8Z)-heptadec-8-en-1-ol 
• 119520-40-0 (Z)-Octadec-9-enoic acid 2-thioxo-2H-pyridin-1-yl ester 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 112-80-1 cis-Octadecenoic acid 
• 10160-25-5 7-bromo-1-(2-tetrahydropyranyloxy)heptane 
• 10160-24-4 7-bromoheptyl alcohol 
• 62873-33-0 heptadec-8-yn-1-ol 

Downstream Products

• 219144-63-5 (Z)-1-(2,3,5,6-tetramethoxyphenyl)-8-heptadecene 
• 7432-41-9 8(Z)-heptadecenoic acid 
• 84306-79-6 3-<(7Z)-hexadecenyl>-4-methylfuran-2,5-dione 

Relevant articles and documents

A divergent synthesis of [1-14C]-mono-E isomers of fatty acids

A convenient synthesis of [1-14C]-mono-trans fatty acid using olefin inversion as a key-step is described. This methodology allows for a facile synthesis of [1-14C]-labelled mono-trans analogues of oleic, linoleic and linolenic acids. As an example, only eleven steps were necessary to obtain the [1-14C]-mono-E isomers of linolenic acid from its commercial all-Z form. In the first step, Barton's decarboxylation procedure yielded a bromo intermediate. Epoxidation of this compound resulted in the formation of three monoepoxides, which could be separated by HPLC. After identification by 1H NMR and MS, the pure monoepoxides were then subjected to inversion consisting of a stereospecific deoxygenation followed by a β-elimination step. Finally, the labelling was introduced by substitution of the bromine by a [14C]-cyano group followed by hydrolysis.

(Z)-Heptadec-8-enylboronic acid: a ppotential lipase inhibitor

(Z)-Heptadec-8-enylboronic acid, a potential lipase inhibitor that is isosteric with oleic acid, and that is unexpectedly sensitive to aerial oxidation, has been prepared in 23percent overall yield from dec-1-yne and 7-bromoheptanol.Disappointingly, the target compound proved inactive under conditions where lipase inhibition would have been expected.