(Benzoylmethylene)triphenylphosphorane

Base Information

• Chemical Name: (Benzoylmethylene)triphenylphosphorane
• CAS No.: 859-65-4
• Molecular Formula: C₂₆H₂₁OP
• Molecular Weight: 380.426
• Hs Code.: 29319000
• European Community (EC) Number: 212-727-2
• NSC Number: 167167
• DSSTox Substance ID: DTXSID90235228
• Nikkaji Number: J500.736D,J79.987D
• Wikidata: Q83117108
• ChEMBL ID: CHEMBL3247919
• Mol file: 859-65-4.mol

Synonyms:SK and F 45349;SKF 45349;SKF-45349

Chemical Property of (Benzoylmethylene)triphenylphosphorane

Chemical Property:

• Vapor Pressure: 3.48E-12mmHg at 25°C
• Melting Point: 183-186°C
• Boiling Point: 550.9°C at 760 mmHg
• Flash Point: 287°C
• PSA: 26.88000
• Density: 1.18g/cm³
• LogP: 4.66560
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Solubility.: Soluble in Methanol (almost transparency).
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 380.133002287
• Heavy Atom Count: 28
• Complexity: 489

Purity/Quality:

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

(Benzoylmethylene)triphenylphosphorane ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C=P(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: It is used in organic synthesis, wittig reagent.

Technology Process of (Benzoylmethylene)triphenylphosphorane

There total 50 articles about (Benzoylmethylene)triphenylphosphorane 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%

triphenylphenacylphosphonium bromide (6048-29-9) → (Benzoylmethylene)triphenylphosphorane (20913-05-7,859-65-4)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 23 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jacs.9b09373

Reference yield: 99.0%

α-bromoacetophenone (70-11-1) + triphenylphosphine (603-35-0) → (Benzoylmethylene)triphenylphosphorane (20913-05-7,859-65-4)

Guidance literature:

α-bromoacetophenone; triphenylphosphine; for 1h; steel ball-milling;

With potassium carbonate; for 3h; Further stages.; steel ball-milling;

DOI:10.1021/ja017908p

Reference yield: 97.0%

Phenacyltriphenylphosphonium iodide (6230-82-6) → (Benzoylmethylene)triphenylphosphorane (20913-05-7,859-65-4)

Guidance literature:

With sodium methylate; In methanol; for 0.0833333h;

DOI:10.1055/s-1981-29497

upstream raw materials:

α-bromoacetophenone

bromobenzene

Bestmann ylide

trimethylsilyl benzoate

Downstream raw materials:

phenacyldiphenylphosphine oxide

1-methyl-2-((phenylcarbonyl)methyl)-1-cyclohexene

2-(4-tert-Butyl-cyclohex-1-enyl)-1-phenyl-ethanone

trans-1,10-diphenyl-2,8-decadiene-1,10-dione

Refernces

• 1、 Zhong, Chun-Hong,Huang, Wenhua. "Synthesis of tertiary phosphine oxides by alkaline hydrolysis of quaternary phosphonium zwitterions using excess t-BuOK and stoichiometric water". supporting information. p. 1537 - 1546. Retrieved 2021/01/07.
• 2、 Liu, Qiang-Qiang,Zheng, Chao,You, Shu-Li. "Silica gel-promoted synthesis of multisubstituted spiroindolenines from tryptamines and γ-chloro-α,β-unsaturated ketones". . . Retrieved 2020/12/02.