Merck
CN
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文件

392278

Sigma-Aldrich

6-溴己腈

95%

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别名:
5-Bromopentyl cyanide, 6-Bromocapronitrile
线性分子式:
Br(CH2)5CN
CAS号:
6621-59-6
分子量:
176.05
EC 号:
229-570-0
MDL编号:
MFCD00013834
PubChem化学物质编号:
24864440
NACRES:
NA.22

检测方案

95%

形式

liquid

折射率

n20/D 1.477 (lit.)

bp

134 °C/13 mmHg (lit.)

密度

1.328 g/mL at 25 °C (lit.)

SMILES string

BrCCCCCC#N

InChI

1S/C6H10BrN/c7-5-3-1-2-4-6-8/h1-5H2

InChI key

PHOSWLARCIBBJZ-UHFFFAOYSA-N

一般描述

6-Bromohexanenitrile (6-Bromohexanonitrile) is an ω-bromoalkanonitrile. Friedel Crafts alkylation of 6-bromohexanenitrile with benzene has been studied.

应用

6-Bromohexanenitrile (6-Bromocapronitrile, 6-Bromohexanonitrile) is suitable reagent used in the synthesis of (5-cyanopentyl)zinc(II) bromide, an organozinc reagent. It may be used in the synthesis of the following:
  • 6-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)hexanenitrile.
  • dimethyl 6,6′-dithiobiscaproimidate, a long-chain dithiobisimidate.
  • N-benzyloxy-(4-cyanopentyl)-carbamic acid ethyl ester, a N-benzyloxy carbamate derivative.
  • 1-hetarylsulfanyl-ω-cyanoalkanes.

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H315 - H319 - H335

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

235.4 °F - closed cup

闪点(°C)

113 °C - closed cup

个人防护装备

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Friedel-Crafts alkylation of benzene by normal ?-chloroalkanoic acids and their methyl esters and nitriles.
Zakharkin LI and Anikina EV
Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 36(2), 327-330 (1987)
H Peretz et al.
European journal of biochemistry, 63(1), 77-82 (1976-03-16)
This communication describes a simple method for synthesizing cleavable bifunctional imido esters of different chain lengths. These reagents, which form covalent crosslinks between lysine residues of proteins, contain a disulfide bond which is cleaved under mild conditions by reducing agents
?Green Chemical" Methods for the Regioselective Synthesis of 1-Hetarylsulfanyl-?-Cyanoalkanes."
Abele E, et al.
Latvijas Kimijas Zurnals, 49(1), 278-282 (2010)
NICKEL-CATALYZED ENANTIOSELECTIVE NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY α-BROMO AMIDES WITH ALKYLZINC REAGENTS: (S)-N-BENZYL-7-CYANO-2-ETHYL-N-PHENYLHEPTANAMIDE.
Sha Lou et al.
Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals, 87, 330-330 (2010-01-01)
Yuan Liu et al.
Tetrahedron, 67(12), 2206-2214 (2011-04-19)
N-Alkyl-N-benzyloxy carbamates, 2, undergo facile intramolecular cyclization with a variety of carbon nucleophiles to give functionalized 5- and 6-membered protected cyclic hydroxamic acids, 3, in good to excellent yields. This method can be extended to prepare seven-membered cyclic hydroxamic acids
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