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Sigma-Aldrich

(S)-(+)-Citronellyl bromide

95%

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Synonym(s):
8-Bromo-2,6-dimethyl-2-octene
Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CH2Br
CAS Number:
Molecular Weight:
219.16
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

liquid

optical activity

[α]20/D +6.8°, neat

refractive index

n20/D 1.474 (lit.)

bp

111 °C/12 mmHg (lit.)

density

1.11 g/mL at 25 °C (lit.)

SMILES string

C[C@H](CCBr)CC\C=C(\C)C

InChI

1S/C10H19Br/c1-9(2)5-4-6-10(3)7-8-11/h5,10H,4,6-8H2,1-3H3/t10-/m0/s1

InChI key

QPKCDMXLSDFCQD-JTQLQIEISA-N

Related Categories

General description

(S)-(+)-Citronellyl bromide is a chiral organic compound that is commonly used as a reagent in organic synthesis to prepare chiral building blocks with the citronellyl group, which is used in various organic syntheses. It can also be used in the formation of chiral catalysts, which are useful in the synthesis of enantiomerically pure compounds.

Application

(S)-(+)-Citronellyl bromide can be used as a reactant in the Negishi cross-coupling reaction. It is also used in the synthesis of spiroacetal parts of spirofungin A and B by reacting with epoxy alcohol via alkyne–lactone coupling reaction and diastereomeric separation.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

203.0 °F - closed cup

flash_point_c

95 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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