Farnesyl bromide

Base Information

• Chemical Name: Farnesyl bromide
• CAS No.: 28290-41-7
• Molecular Formula: C₁₅H₂₅Br
• Molecular Weight: 285.267
• European Community (EC) Number: 628-910-9
• Nikkaji Number: J29.154D,J882.628E
• Mol file: 28290-41-7.mol

Synonyms:28290-41-7;trans,trans-Farnesyl bromide;(E,E)-Farnesyl Bromide;Farnesyl bromide;(2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene;(2E,6E)-1-Bromo-3,7,11-trimethyl-2,6,10-dodecatriene;2,6,10-Dodecatriene, 1-bromo-3,7,11-trimethyl-, (2E,6E)-;farnesylbromide;e,e-farnesyl bromide;(E,E)-Farnesylbromide;2E,6E-Farnesyl Bromide;SCHEMBL255003;SCHEMBL11844741;BCP20951;trans,trans-Farnesyl bromide, 95%;MFCD00054465;AKOS025296196;AS-42993;BP-29841;A876746;J-017032;(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl bromide;(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienylbromide;(E,E) -3,7,11-Trimethyl-2,6,10-dodecatrienyl bromide;(E,E)-3,7,11,-Trimethyl-2,6,10-dodecatrienyl bromide;(2E,6E)-1-Bromo-3,7,11-trimethyl-2,6,10-dodecatriene #;(6E,10E)-12-BROMO-2,6,10-TRIMETHYLDODECA-2,6,10-TRIENE

Chemical Property of Farnesyl bromide

Chemical Property:

• Vapor Pressure: 0.000267mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Boiling Point: 333.3°Cat760mmHg
• Flash Point: 152.2°C
• PSA: 0.00000
• Density: 1.058g/cm³
• LogP: 5.80050
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 284.11396
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

97% ^*data from raw suppliers

(E,E)-FarnesylBromide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCBr)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CBr)/C)/C)C
• General Description: **TRANS,TRANS-FARNESYL BROMIDE** is a brominated terpenoid derivative characterized by its (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl structure, serving as a key intermediate in the synthesis of cyclic terpenoids. In the context of polyenic cyclisation reactions, it functions as a precursor for generating optically active intermediates, such as dihydropyran derivatives, which can be further transformed into bioactive terpenoid lactones like (+)-dihydroactinidiolide and (-)-norambreinolide. Its utility lies in facilitating stereoselective cyclisation processes mediated by reagents like SnCl4, contributing to efficient routes for cyclic terpenoid synthesis. **Return:** TRANS,TRANS-FARNESYL BROMIDE is a brominated terpenoid intermediate used in stereoselective cyclisation reactions to synthesize optically active cyclic terpenoids, such as lactones, via polyenic precursor pathways.

Technology Process of Farnesyl bromide

There total 31 articles about Farnesyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Farnesol (106-28-5) → farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7)

Guidance literature:

With pyridine; phosphorus tribromide; In diethyl ether; at 5 ℃; for 3h; Darkness;

DOI:10.1002/jlcr.3083

Reference yield: 96.0%

(+/-)-nerolidol (7212-44-4) → farnesyl bromide (24163-93-7,24163-94-8,28290-41-7,56881-57-3,6874-67-5)

Guidance literature:

With phosphorus tribromide; triethylamine; In toluene; at -5 - 23 ℃; for 1.33333h; Product distribution / selectivity;

Reference yield: 91.0%

farnesol (4602-84-0) → farnesyl bromide (24163-93-7,24163-94-8,28290-41-7,56881-57-3,6874-67-5)

Guidance literature:

With phosphorus tribromide; triethylamine; In toluene; at -5 ℃; for 2h; Product distribution / selectivity;

upstream raw materials:

(+/-)-nerolidol

(S)-(+)-nerolidol

farnesol

pyridine

Downstream raw materials:

farnesal

Farnesal

6,10,14-trimethyl-5,9,13-pentadecatrien-2-one

squalene

Refernces

Cyclisation of Polyenic β-Keto Sulphoxides. A Novel Route to Optically Active Intermediates for Cyclic Terpenoid Synthesis

10.1039/c39910001173

The research focuses on the cyclisation of polyenic β-keto sulphoxides as a novel route to optically active intermediates for cyclic terpenoid synthesis. The purpose of this study was to explore the potential of using polyenic β-keto sulphoxides as precursors for the biogenetic-like cyclisation of polyenes, which could lead to the synthesis of optically pure cyclic terpenoids. The researchers successfully demonstrated that optically active polyenic β-keto sulphoxides 4 and 5, when mediated by SnCl4, undergo cyclisation to yield diastereoisomeric dihydropyran derivatives 6a,b and 10a,b, respectively. These derivatives could be further converted into (+)-dihydroactinidiolide 7 and (-)-norambreinolide 11. The study concluded that this method provides an efficient route to optically active intermediates for the synthesis of cyclic terpenoids, using chemicals such as SnCl4, geranyl bromide, farnesyl bromide, and RuO2-NaIO4 in the process.

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