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377392

(R)-(−)-Citronellyl bromide

Name: (<I>R</I>)-(−)-Citronellyl bromide
Brand: ALDRICH

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.)

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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)

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)

Hierarchical self-assembly of an azobenzene dyad with inverted amide connection into toroidal and tubular nanostructures.

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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