TRANS,TRANS-FARNESYL BROMIDE Chemical Properties

Boiling point:

100-110 °C15 mm Hg(lit.)

Density 

1.052 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.509(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Oil

color 

Colourless to Light Brown

InChI

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+

InChIKey

FOFMBFMTJFSEEY-YFVJMOTDSA-N

SMILES

C(Br)/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\C

CAS DataBase Reference

28290-41-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

RIDADR 

UN 3334

WGK Germany 

3

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Dam. 1
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich

TRANS,TRANS-FARNESYL BROMIDE Usage And Synthesis

Chemical Properties

Brown Oil

Uses

An analog of Farnesol, produced in the dimorphic fungus Candida albicans

Uses

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

Synthesis

Trans,trans-farnesyl bromide was prepared as follows: phosphorus tribromide (0.95 mL, 10.25 mmol) was added dropwise over a few minutes to a stirred solution of trans,trans-farnesyl alcohol 3 (6.9 g, 31.08 mmol) in ether (80 mL) at 0 ??C. The reaction mixture was stirred at 0??C for an additional 1 hour. The reaction was quenched with water (5 mL), the ether was removed under reduced pressure and the resulting slurry was suspended in water (100 mL). The aqueous slurry was extracted with hexane (3× 150 mL), dried with anhydrous Na2SO4, and the solvent was evaporated to give the desired bromide trans,trans-farnesyl bromide, Yield: 8.7 g (crude product); TLCRf: 0.93 (n-hexane solution of 10% EtOAc).

TRANS,TRANS-FARNESYL BROMIDE(28290-41-7)Related Product Information

• Allyl bromide
• SOLANESYL BROMIDE
• GERANYL GERANYL BROMIDE
• ALL TRANS GERANYL GERANYL BROMIDE, [1-3H]
• TRANS,TRANS-FARNESYL BROMIDE
• TRANS, TRANS FARNESYL BROMIDE, [1-3H]