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377716

Sigma-Aldrich

(S)-(+)-Citronellyl bromide

95%

Synonym(s):

8-Bromo-2,6-dimethyl-2-octene

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CH2Br
CAS Number:
143615-81-0
Molecular Weight:
219.16
MDL number:
MFCD00134459
UNSPSC Code:
12352101
PubChem Substance ID:
24863519
NACRES:
NA.22

Quality Level

100

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

203.0 °F

Flash Point(C)

95 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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