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333549

Sigma-Aldrich

3-Bromocyclohexene

technical grade, 90%

Synonym(s):

2-Cyclohexen-1-yl bromide

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About This Item

Empirical Formula (Hill Notation):
C6H9Br
CAS Number:
1521-51-3
Molecular Weight:
161.04
Beilstein/REAXYS Number:
635953
MDL number:
MFCD00013775
UNSPSC Code:
12352100
PubChem Substance ID:
24860144
NACRES:
NA.22

grade

technical grade

Quality Level

100

assay

90%

form

liquid

refractive index

n20/D 1.528 (lit.)

bp

57-58 °C/12 mmHg (lit.)

density

1.4 g/mL at 25 °C (lit.)

functional group

bromo

storage temp.

−20°C

SMILES string

BrC1CCCC=C1

InChI

1S/C6H9Br/c7-6-4-2-1-3-5-6/h2,4,6H,1,3,5H2

Inchi Key

AJKDUJRRWLQXHM-UHFFFAOYSA-N

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Application

3-Bromocyclohexene was used in the synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine. It was also used in the synthesis of enantiopure cyclohexitols such as muco-quercitol, D-chiro-inocitol and allo-inocitol.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

129.2 °F - closed cup

flash_point_c

54 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT1965
MKCQ2753
MKBN7704V
MKBH1405V
09122BJ

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Synthesis of enantiopure cyclitols from (?)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S, S)-hydrobenzoin and (S)-mandelic acid as chiral sources.
Lee YJ, et al.
Tetrahedron, 61(8), 1987-2001 (2005)
Y Nishiyama et al.
Chemical & pharmaceutical bulletin, 49(2), 233-235 (2001-02-24)
A facile and efficient synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine [Boc-Tyr(Chx)-OH] is described. Boc-Tyr-OH was treated with NaH in dimethylformamide and then with 3-bromocyclohexene to give N-Boc-O-(cyclohex-2-enyl)-L-tyrosine [Boc-Tyr(Che)-OH] in 70% yield. Hydrogenation of Boc-Tyr(Che)-OH over PtO2 afforded Boc-Tyr(Chx)-OH in almost quantitative yield. The

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