[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide

Base Information

• Chemical Name: [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide
• CAS No.: 62285-98-7
• Molecular Formula: C33H38BrP
• Molecular Weight: 545.542
• Mol file: 62285-98-7.mol

Synonyms:Phosphonium,[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl]triphenyl-,bromide (9CI);Phosphonium,[3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl]triphenyl-,bromide, (E,E)-;

Chemical Property of [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide

Chemical Property:

• PSA: 13.59000
• LogP: 5.01360

Purity/Quality:

99% ^*data from raw suppliers

[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl]triphenyl-phosphoniumBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl]triphenyl-phosphonium Bromide is used in the synthesis of all-trans-retinoic acid (ATRA), a precursor of vitamin A

Technology Process of [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide

There total 22 articles about [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium 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%

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol (59057-30-6) + triphenylphosphine hydrobromide (6399-81-1) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Guidance literature:

In methanol; for 75h; Ambient temperature;

DOI:10.1021/jo00185a020

Reference yield: 92.8%

3-methyl-5-bromo-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene (38987-92-7) + triphenylphosphine (603-35-0) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Guidance literature:

In acetonitrile; at 50 - 55 ℃; for 5h; Inert atmosphere;

Reference yield:

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (17974-55-9) + triphenylphosphine hydrobromide (6399-81-1) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Guidance literature:

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate; With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;

triphenylphosphine hydrobromide; In methanol; at 20 ℃; for 24h;

upstream raw materials:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol

triphenylphosphine hydrobromide

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

(E)-β-ionone

Downstream raw materials:

3,7,11,15,20,24,28,32-octamethyl-1,34-bis(2,6,6-trimethylcyclohex-1-enyl)tetratriaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29,31,33-heptadecaene

3,7,11,16,20,24-hexamethyl-1,26-bis(2,6,6-trimethylcyclohex-1-enyl)hexacosa-1,3,5,7,9,11,13,15,17,19,21,23,25-tridecaene

Retinol acetate

retinyl palmitate

Refernces

• 1、 -. "Preparation method of vitamin A acetate intermediate C15 and vitamin A acetate". Paragraph 0134-0137. . Retrieved 2020/08/18.
• 2、 Kildahl-Andersen, Geir,Anthonsen, Thorleif,Liaaen-Jensen, Synnove. "Longer polyenyl cations in relation to soliton theory". . p. 2803 - 2811. Retrieved 2008/03/12.