Acetonyltriphenylphosphonium chloride

Base Information

• Chemical Name: Acetonyltriphenylphosphonium chloride
• CAS No.: 1235-21-8
• Molecular Formula: C21H20ClOP
• Molecular Weight: 354.816
• Hs Code.: 29319019
• European Community (EC) Number: 214-974-1
• NSC Number: 6741
• UNII: 5WP8HJ7H8U
• DSSTox Substance ID: DTXSID50924520
• Mol file: 1235-21-8.mol

Synonyms:1235-21-8;Acetonyltriphenylphosphonium chloride;(2-oxopropyl)triphenylphosphonium chloride;2-Oxopropyltriphenylphosphonium chloride;Phosphonium, (2-oxopropyl)triphenyl-, chloride;Phosphonium, acetonyltriphenyl-, chloride;Acetonyl triphenylphosphonium chloride;2-oxopropyl(triphenyl)phosphanium;chloride;NSC 6741;EINECS 214-974-1;5WP8HJ7H8U;NSC-6741;MFCD00011813;Phosphonium, (2-oxopropyl)triphenyl-, chloride (1:1);acetonyl(triphenyl)phosphonium chloride;UNII-5WP8HJ7H8U;C21H20OP.Cl;ghl.PD_Mitscher_leg0.307;SCHEMBL1251194;C21-H20-O-P.Cl;WLN: 1V1PR&R&R &G;DTXSID50924520;AKOS015904016;CS-W011845;LS-106868;(2-Oxopropyl)(triphenyl)phosphanium chloride;A1305;FT-0621809;D88412;A805112;J-004949

Chemical Property of Acetonyltriphenylphosphonium chloride

Chemical Property:

• Appearance/Colour: white to slight grayish crystaline powder
• Melting Point: 243-245 °C(lit.)
• PSA: 30.66000
• LogP: 0.57350
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in hot water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 354.0940299
• Heavy Atom Count: 24
• Complexity: 328

Purity/Quality:

98%, ^*data from raw suppliers

Acetonyltriphenylphosphonium Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-S24/25-S22-60-37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-]
• Uses: Acetonyltriphenylphosphonium chloride is used to investigate the antimycobacterial activities of Me alkenyl quinolones. It is used as a reactant for synthesis of unsaturated esters and ketones containing multiple aromatic and heteroaromatic rings using Suzuki coupling - Wittig olefination. Used to investigate the antimycobacterial activities of Me alkenyl quinolonesReactant for synthesis of: Unsaturated esters and ketones containing multiple aromatic and heteroaromatic rings using Suzuki coupling - Wittig olefinationFused oxygen and nitrogen heterocycles via regioselective cyclocondensation Reactant for Wittig olefinations

Technology Process of Acetonyltriphenylphosphonium chloride

There total 10 articles about Acetonyltriphenylphosphonium 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: 99.0%

chloroacetone (78-95-5) + triphenylphosphine (603-35-0) → acetonyltriphenylphosphonium chloride (1235-21-8)

Guidance literature:

In chloroform; for 18.5h; Heating;

DOI:10.1055/s-1987-28168

Reference yield: 61.0%

1-Chloro-2,2-dicyanoethylen (10472-09-0) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → acetonyltriphenylphosphonium chloride (1235-21-8) + 1-Acetyl-3,3-dicyano-2-propen-1-ylidentriphenylphosphorane (81787-13-5)

Guidance literature:

In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1055/s-1982-29724

Reference yield:

chloroacetone (78-95-5) → acetonyltriphenylphosphonium chloride (1235-21-8)

Guidance literature:

With sodium carbonate; triphenylphosphine; In chloroform; at 20 ℃; Reflux;

DOI:10.1016/j.bmcl.2013.05.016

upstream raw materials:

chloroacetone

triphenylphosphine

1-triphenylphosphoranylidene-2-propanone

triphenylphosphorane

Downstream raw materials:

[Ph3PCH2COMe][PtCl3(η(2)-C2H4)]

(E)-7-Phenyl-3-hepten-2-on-7,7-d⁽²⁾

(E)-hepta-6,3-dien-2-one

(E)-6-phenyl-3-hexen-2-one

Refernces

• 1、 Schuda, Paul Francis,Ebner, Cynthia B.,Potlock, Steven J.. "The Synthesis of 4-Oxo-2-pentenoic Esters by Wittig Reaction Using α-Oxoesters". . p. 1055 - 1057. Retrieved 1987.
• 2、 -. "4-furfurylthiopentanone-2 preparation method". Paragraph 0018; 0039-0044; 0049-0054; 0059-0064; 0069-0073. . Retrieved 2019/11/04.