(2-Aminobenzyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (2-Aminobenzyl)triphenylphosphonium bromide
• CAS No.: 78133-84-3
• Molecular Formula: C25H23 N P . Br
• Molecular Weight: 448.342
• European Community (EC) Number: 624-626-4
• DSSTox Substance ID: DTXSID50449889
• Mol file: 78133-84-3.mol

Synonyms:(2-aminobenzyl)triphenylphosphonium bromide

Chemical Property of (2-Aminobenzyl)triphenylphosphonium bromide

Chemical Property:

• Melting Point: 245 °C (dec.)(lit.)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 447.07515
• Heavy Atom Count: 28
• Complexity: 386

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2-Aminobenzyl)triphenylphosphonium bromide 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](CC2=CC=CC=C2N)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]
• Uses: Reactant for:Intramolecular Wittig reactionPreparation of 2,3-disubstituted indolesPreparation of pyrrolocarbazoles as poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors

Technology Process of (2-Aminobenzyl)triphenylphosphonium bromide

There total 3 articles about (2-Aminobenzyl)triphenylphosphonium 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: 95.0%

(2-nitrobenzyl)triphenylphosphonium bromide (23308-83-0) → (2-aminobenzyl)triphenylphosphonium bromide (78133-84-3)

Guidance literature:

With hydrogen bromide; zinc; In ethanol;

Reference yield: 88.0%

2-Aminobenzyl alcohol (5344-90-1) + triphenylphosphine hydrobromide (6399-81-1) → (2-aminobenzyl)triphenylphosphonium bromide (78133-84-3)

Guidance literature:

In acetonitrile; for 6h; Heating;

Reference yield:

1-methyl-2-nitrobenzene (88-72-2) → (2-aminobenzyl)triphenylphosphonium bromide (78133-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-bromosuccinimide (NBS), peroxyde de benzoyle / CCl₄

2: 69 percent / toluene / 1.) 3h, RT, 2.) 2h, reflux

3: 94 percent / 48percent HBr, Zn / ethanol / 2 h / Heating

With N-Bromosuccinimide; Perbenzoic acid; hydrogen bromide; zinc; In tetrachloromethane; ethanol; toluene;

DOI:10.1016/S0040-4020(01)96783-3

upstream raw materials:

2-Aminobenzyl alcohol

triphenylphosphine hydrobromide

(2-nitrobenzyl)triphenylphosphonium bromide

1-methyl-2-nitrobenzene

Downstream raw materials:

(E)-1-(tert-butoxycarbonyl)-2-(1-(4-((tert-butoxycarbonyl)oxy)phenyl)-3-methoxy-3-oxoprop-1-en-2-yl)-1H-indole-3-carboxylic acid

(E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate

triphenyl((ethyl(2-carbamoyl)acetate)-2-benzyl)phosphonium bromide

2-(2-methoxyphenyl)-1H-indole

Refernces

• 1、 Obermoser, Victoria,Urban, Margarethe E.,Murgueitio, Manuela S.,Wolber, Gerhard,Kintscher, Ulrich,Gust, Ronald. "New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile". supporting information. p. 138 - 152. Retrieved 2016/08/30.
• 2、 -. "COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES". . . Retrieved 2012/04/23.