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377392

Sigma-Aldrich

(R)-(−)-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:
10340-84-8
Molecular Weight:
219.16
MDL number:
MFCD00134453
UNSPSC Code:
12352101
PubChem Substance ID:
24863501
NACRES:
NA.22

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.)

functional group

alkyl halide
bromo

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-/m1/s1

InChI key

QPKCDMXLSDFCQD-SNVBAGLBSA-N

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Application

(R)-(−)-Citronellylbromide can be used as a reactant to synthesize:
  • (R)-3,7-dimethyloct-6-ene-1-amine via Gabriel synthesis which is then condensed with dicarboxylic acids to synthesize retro amides.
  • Citronellyl derivatives of sulfoximines and sulfondiimines via alkylation using potassium hydroxide and dimethyl sulfoxide.
  • Citronellyltriphenylphosphonium bromide which can be used as a key intermediate to synthesize (+)-caparratriene via Witting reaction.

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)

203.0 °F - closed cup

Flash Point(C)

95 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

377392-BULK:
377392-5G:
377392-1G:
377392-VAR:
377392-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN6400
09115BG
07805BR
04011BY
09516JA

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Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde
Vydrina V, et al.
Chemistry of Natural Compounds, 54, 461-463 (2018)
N-Alkylations of NH-Sulfoximines and NH-Sulfondiimines with Alkyl Halides Mediated by Potassium Hydroxide in Dimethyl Sulfoxide
Hendriks C, et al.
advanced synthesis and catalysis, 356, 1847-1852 (2014)
Takuho Saito et al.
Organic & biomolecular chemistry, 18(21), 3996-3999 (2020-05-16)
Inversion of the connectivity of amide groups in foldable azobenzene dyads with chiral side chains, which can self-assemble into toroids and nanotubes, significantly increases the thermal stability of these aggregates. The results can be explained by the geometrical difference of

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