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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[1].
  • Citronellyl derivatives of sulfoximines and sulfondiimines via alkylation using potassium hydroxide and dimethyl sulfoxide[2].
  • Citronellyltriphenylphosphonium bromide which can be used as a key intermediate to synthesize (+)-caparratriene via Witting reaction[3].

pictograms

Exclamation mark
GHS07

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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Certificates of Analysis (COA)

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

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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
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)

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