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TRANS,TRANS-FARNESYL BROMIDE manufacturers
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| | TRANS,TRANS-FARNESYL BROMIDE Basic information |
| Product Name: | TRANS,TRANS-FARNESYL BROMIDE | | Synonyms: | TRANS,TRANS-1-BROMO-3,7,11-TRIMETHYL-2,6,10-DODECATRIENE;TRANS,TRANS-FARNESYL BROMIDE;(2E,6E)-;1-Bromo-3,7,11-trimethyl-2,6,10-dodecatriene;3,7,11-Trimethyl-2,6,10-dodecatrienyl bromide;(E,E)-Farnesyl Bromide;trans,trans-Farnesyl bromide 95%;-1-Bromo-3,7,11-trimethyldodeca-2,6,10-triene | | CAS: | 28290-41-7 | | MF: | C15H25Br | | MW: | 285.26 | | EINECS: | | | Product Categories: | Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Aliphatics | | Mol File: | 28290-41-7.mol |  |
| | 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.) | | Fp | >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 |
| 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 |
| | 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 0C 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).
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| | TRANS,TRANS-FARNESYL BROMIDE Preparation Products And Raw materials |
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