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Sigma-Aldrich

6-Bromohexanenitrile

95%

Synonym(s):

5-Bromopentyl cyanide, 6-Bromocapronitrile

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About This Item

Linear Formula:
Br(CH2)5CN
CAS Number:
6621-59-6
Molecular Weight:
176.05
EC Number:
229-570-0
MDL number:
MFCD00013834
UNSPSC Code:
12352100
PubChem Substance ID:
24864440
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.477 (lit.)

bp

134 °C/13 mmHg (lit.)

density

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

General description

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

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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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