3,5-Dihydroxybenzyltriphenylphosphonium bromide

Base Information

• Chemical Name: 3,5-Dihydroxybenzyltriphenylphosphonium bromide
• CAS No.: 29680-77-1
• Molecular Formula: C25H22O2P.Br
• Molecular Weight: 465.31900
• DSSTox Substance ID: DTXSID60585303
• Mol file: 29680-77-1.mol

Synonyms:3,5-Dihydroxybenzyltriphenylphosphonium bromide;29680-77-1;DTXSID60585303;(3,5-dihydroxyphenyl)methyl-triphenylphosphanium;bromide;[(3,5-Dihydroxyphenyl)methyl](triphenyl)phosphanium bromide

Chemical Property of 3,5-Dihydroxybenzyltriphenylphosphonium bromide

Chemical Property:

• PSA: 54.05000
• LogP: 1.59590
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 464.05408
• Heavy Atom Count: 29
• Complexity: 408

Purity/Quality:

97% ^*data from raw suppliers

3,5-DIHYDROXYBENZYLTRIPHENYLPHOSPHONIUM BROMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](CC2=CC(=CC(=C2)O)O)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]

Technology Process of 3,5-Dihydroxybenzyltriphenylphosphonium bromide

There total 8 articles about 3,5-Dihydroxybenzyltriphenylphosphonium 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: 85.0%

3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide (29680-76-0) → (3,5-dihydroxybenzyl)triphenylphosphonium bromide (29680-77-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 5h; Heating;

DOI:10.1071/CH07044

Reference yield: 72.3%

5-(hydroxymethyl)benzene-1,3-diol (29654-55-5) + triphenylphosphine hydrobromide (6399-81-1) → (3,5-dihydroxybenzyl)triphenylphosphonium bromide (29680-77-1)

Guidance literature:

In acetonitrile; for 12h; Reflux;

Reference yield:

3,5-dibenzyloxybenzyl alcohol (24131-31-5) → (3,5-dihydroxybenzyl)triphenylphosphonium bromide (29680-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C / ethanol

2: (i) PBr₃, THF, benzene, (ii) /BRN= 385737/, Py, (iii) /BRN= 610776/, benzene

3: TsOH / methanol

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol;

upstream raw materials:

3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide

5-(bromomethyl)benzene-1,3-diol

5-(hydroxymethyl)benzene-1,3-diol

5-(bromomethyl)-1,3-phenylene diacetate

Downstream raw materials:

trans-piceatannol

Refernces

• 1、 Chand, Satish,Banwell, Martin G.. "Biomimetic preparation of the racemic modifications of the stilbenolignan aiphanol and three congeners". . p. 243 - 250. Retrieved 2008/02/11.