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Safety Information

331929

Sigma-Aldrich

trans,trans-Farnesyl bromide

95%

Synonym(s):

trans,trans-1-Bromo-3,7,11-trimethyl-2,6,10-dodecatriene

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About This Item

Linear Formula:
(CH3)2C=CH[CH2CH2C(CH3)=CH]2CH2Br
CAS Number:
28290-41-7
Molecular Weight:
285.26
MDL number:
MFCD00054465
UNSPSC Code:
12352100
PubChem Substance ID:
24860010
NACRES:
NA.22

Quality Level

200

Assay

95%

form

liquid

refractive index

n20/D 1.509 (lit.)

bp

100-110 °C/15 mmHg (lit.)

density

1.052 g/mL at 25 °C (lit.)

functional group

alkyl halide
bromo

storage temp.

2-8°C

SMILES string

[H]\C(CBr)=C(\C)CC\C([H])=C(/C)CC\C=C(\C)C

InChI

1S/C15H25Br/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+

InChI key

FOFMBFMTJFSEEY-YFVJMOTDSA-N

Related Categories

Application

Farnesyl bromide was used in the preparation of:
  • S-trans, trans-farnesyl-L-cysteine methylester, a post translational modified amino acid
  • umbelliprenin, starting reagent for the synthesis of (±)-farnesiferol A and (±)-farnesiferol C
  • prenylated peptides

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Precautionary Statements

P261 - P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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

331929-VAR:
331929-1G:
331929-5G:
331929-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000411741
0000411741
0000388796
0000314090
0000388796

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Biogentic-type synthesis of (?)-farnesiferol A and (?)-farnesiferol C.
van Tamelen EE and Coates RM.
Chemical Communications (Cambridge, England), 13, 413-415 (1996)
O Kisselev et al.
The Journal of biological chemistry, 270(43), 25356-25358 (1995-10-27)
Post-translational prenylation of the carboxyl-terminal cysteine is a characteristic feature of the guanine nucleotide-binding protein (G protein) gamma subunits. Recent findings show that the farnesylated COOH-terminal tail of the gamma 1 subunit is a specific determinant of rhodopsin-transducin coupling. We
M Liakopoulou-Kyriakides et al.
Amino acids, 2(3), 285-288 (1992-10-01)
S-trans, trans-farnesyl-L-cysteine methylester, a post translational modified amino acid, was synthesized from farnesyl bromide and L-cysteine methylester hydrochloride salt in the presence of triethylamine. Its purification as well as separation from the other isomers by HPLC on RP Vydac C4

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