COUMACHLOR

Base Information

• Chemical Name: COUMACHLOR
• CAS No.: 81-82-3
• Molecular Formula: C19H15ClO4
• Molecular Weight: 342.779
• Mol file: 81-82-3.mol

Synonyms:Coumachlor(6CI);Coumarin, 3-(a-acetonyl-p-chlorobenzyl)-4-hydroxy- (7CI,8CI);(?à)-3-(a-Acetonyl-4-chlorobenzyl)-4-hydroxy coumarin;(?à)-Coumachlor;(?à)-p-Chlorowarfarin;3-(a-Acetonyl-4-chlorobenzyl)-4-hydroxycoumarin;3-(a-p-Chlorophenyl-b-acetylethyl)-4-hydroxycoumarin;3-[1-(p-Chlorophenyl)-2-acetylethyl]-4-hydroxycoumarin;Cumachlor;DL-3-(a-Acetonyl-4-chlorobenzyl)-4-hydroxycoumarin;Experimental Rodenticide 332;Geigy Rodenticide Exp. 332;Racemic coumachlor;Tomorin;p-Chlorowarfarin;

Chemical Property of COUMACHLOR

Chemical Property:

• Appearance/Colour: light yellow powder
• Melting Point: 168-170 °C
• Boiling Point: 543.108 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 282.262 °C
• PSA: 67.51000
• Density: 1.384 g/cm³
• LogP: 4.26300
• Storage Temp.: Refrigerator
• Solubility.: acetone: soluble

Purity/Quality:

99% ^*data from raw suppliers

Coumachlor ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 48/22-52/53
• Safety Statements: 37-61

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Rodenticide. Coumachlor was used as internal standard for simultaneous enantioseparation of (+/-)-warfarin by chiral capillary electrochromatography with electrospray ionization mass spectrometry. An internal standard in the analysis of the rodenticide Warfarin.

Technology Process of COUMACHLOR

There total 17 articles about COUMACHLOR 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%

4-(4-chlorophenyl)-3-buten-2-one (3160-40-5) + 4-hydroxydihydrocoumarin → (R)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one (81-82-3,70888-76-5,95041-39-7,95271-89-9)

Guidance literature:

With (S,S)-N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine; p-Toluic acid; In toluene; at 20 ℃; for 72h; enantioselective reaction;

DOI:10.1039/c2ob26334c

Reference yield: 96.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + (3E)-4-(4-chlorophenyl)-3-buten-2-one (30626-03-0) → coumachlor (81-82-3)

Guidance literature:

With polystyrene-divinylbenzene support prepared with 1-chlorodecane as porogen with immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene; at 100 ℃; for 96h; Reagent/catalyst; Time; Green chemistry;

DOI:10.1016/j.jcat.2013.10.009

Reference yield: 91.0%

4-(4-chlorophenyl)-3-buten-2-one (3160-40-5) + 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → (R)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one (81-82-3,70888-76-5,95041-39-7,95271-89-9) + (S)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one (81-82-3,95041-39-7,95271-89-9,70888-76-5)

Guidance literature:

With (1R,2R)-1,2-cyclohexanediamine-MIL-4; In tetrahydrofuran; at 10 ℃; for 96h; enantioselective reaction;

DOI:10.1002/adsc.201300554

upstream raw materials:

4-(4-chlorophenyl)-3-buten-2-one

4-hydroxy[1]benzopyran-2-one

2-Methoxypropene

4-chlorobenzaldehyde

Downstream raw materials:

3-fluoro-3-<1-(4-chlorophenyl)-3-oxobutyl>-2H-benzopyran-2,4-dione

(R)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one

(S)-3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one

4-hydroxy-3-[1-(4-chloro-phenyl)-5-furan-2-yl-3-oxo-pent-4-enyl]-chromen-2-one

Refernces

• 1、 Kucherenko, Alexander S.,Kostenko, Alexey A.,Zhdankina, Galina M.,Kuznetsova, Olga Yu.,Zlotin, Sergei G.. "Green asymmetric synthesis of Warfarin and Coumachlor in pure water catalyzed by quinoline-derived 1,2-diamines". supporting information. p. 754 - 759. Retrieved 2018/02/14.
• 2、 Kumagai, Jun,Kohari, Yoshihito,Seki, Chigusa,Uwai, Koji,Okuyama, Yuko,Kwon, Eunsang,Nakano, Hiroto. "Chiral primary amino amide alcohol organocatalyst for the asymmetric Michael addition of 4-hydroxycoumarin with α,β-unsaturated ketones". . p. 1124 - 1134. Retrieved 2015/04/27.