(2-Methylbenzyl)triphenylphosphonium chloride

Base Information

• Chemical Name: (2-Methylbenzyl)triphenylphosphonium chloride
• CAS No.: 63368-36-5
• Molecular Formula: C26H24ClP
• Molecular Weight: 402.903
• Hs Code.: 2931900090
• European Community (EC) Number: 264-112-3
• DSSTox Substance ID: DTXSID40885757
• ChEMBL ID: CHEMBL3229242
• Mol file: 63368-36-5.mol

Synonyms:63368-36-5;(2-METHYLBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE;Phosphonium, [(2-methylphenyl)methyl]triphenyl-, chloride;(2-methylphenyl)methyl-triphenylphosphanium;chloride;EINECS 264-112-3;MFCD00031577;((2-Methylphenyl)methyl)triphenylphosphonium chloride;Phosphonium, ((2-methylphenyl)methyl)triphenyl-, chloride;Phosphonium, ((2-methylphenyl)methyl)triphenyl-, chloride (1:1);[(2-methylphenyl)methyl]triphenylphosphonium chloride;Phosphonium, [(2-methylphenyl)methyl]triphenyl-, chloride (1:1);(2-Methylbenzyl)triphenylphosphoniumchloride;SCHEMBL2450028;CHEMBL3229242;DTXSID40885757;AC1063;Benzofuran-5-ylmethanesulfonylchloride;AKOS004907757;SY021251;2-Methylbenzyltriphenylphosphonium chloride;CS-0044349;FT-0605002;FT-0613014;A834347

Chemical Property of (2-Methylbenzyl)triphenylphosphonium chloride

Chemical Property:

• Appearance/Colour: WHITE CRYSTALLINE POWDER
• Melting Point: 275-277oC
• PSA: 13.59000
• LogP: 2.49310
• Sensitive.: Hygroscopic
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 402.1304155
• Heavy Atom Count: 28
• Complexity: 380

Purity/Quality:

99% ^*data from raw suppliers

(2-METHYLBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Cl-]

Technology Process of (2-Methylbenzyl)triphenylphosphonium chloride

There total 2 articles about (2-Methylbenzyl)triphenylphosphonium chloride 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%

1-chloromethyl-2-methylbenzene (552-45-4) + triphenylphosphine (603-35-0) → ortho-methylbenzyltriphenylphosphonium chloride (63368-36-5)

Guidance literature:

In toluene; at 110 ℃; Inert atmosphere;

DOI:10.1002/ejoc.200900841

Reference yield: 89.0%

triphenylphosphine (603-35-0) + 2-methylbenzyl bromide (89-92-9) → ortho-methylbenzyltriphenylphosphonium chloride (63368-36-5)

Guidance literature:

at 100 ℃; for 0.166667h; Inert atmosphere; neat (no solvent);

DOI:10.1021/ja300943z

Reference yield: 88.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + ortho-methylbenzyltriphenylphosphonium chloride (63368-36-5) → (E)-3-(2-methylstyryl)-1H-indole

Guidance literature:

ortho-methylbenzyltriphenylphosphonium chloride; With sodium hydride; In toluene; mineral oil; at 20 ℃; for 0.5h;

Indole-3-carboxaldehyde; In toluene; mineral oil; at 80 ℃; for 2h;

DOI:10.1021/acs.orglett.9b01675

upstream raw materials:

1-chloromethyl-2-methylbenzene

triphenylphosphine

2-methylbenzyl bromide

Downstream raw materials:

2,2'-dimethyl-stilbene

di-o-tolylethyne

α,α'-dibromo-2,2'-dimethyl-bibenzyl

2-m-tolyl-1-o-tolylethyne

Refernces

• 1、 Guan, Xu-Kai,Liu, Guo-Feng,An, Dong,Zhang, Heng,Zhang, Suo-Qin. "Chiral Imidodiphosphoric Acid-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Poly-Substituted 3,4-Dihydro-2 H-pyrans: [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketoesters and 3-Vinylindoles". supporting information. p. 5438 - 5442. Retrieved 2019/08/01.
• 2、 Byrne, Peter A.,Gilheany, Declan G.. "Unequivocal experimental evidence for a unified lithium salt-free wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products". supporting information; experimental part. p. 9225 - 9239. Retrieved 2012/07/14.