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81-82-3

Basic Information
CAS No.: 81-82-3
Name: COUMACHLOR
Article Data: 22
Molecular Structure:
Molecular Structure of 81-82-3 (COUMACHLOR)
Formula: C19H15ClO4
Molecular Weight: 342.779
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;
EINECS: 201-378-1
Density: 1.384 g/cm3
Melting Point: 168-170 °C
Boiling Point: 543.108 °C at 760 mmHg
Flash Point: 282.262 °C
Solubility: water: 0.5 mg/L at 20 °C
Appearance: light yellow powder
Hazard Symbols:
Risk Codes: 48/22-52/53
Safety: 37-61
Transport Information: UN 2811
PSA: 67.51000
LogP: 4.26300
Synthetic route
1076-38-6

4-hydroxy[1]benzopyran-2-one

30626-03-0

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

81-82-3

coumachlor

Conditions
ConditionsYield
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; Michael Addition; Green chemistry;96%
3160-40-5

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

1076-38-6

4-hydroxy[1]benzopyran-2-one

81-82-3

coumachlor

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water for 14h; Heating;75%
Michael Addition;
1076-38-6

4-hydroxy[1]benzopyran-2-one

116-11-0

2-Methoxypropene

104-88-1

4-chlorobenzaldehyde

81-82-3

coumachlor

Conditions
ConditionsYield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 2-Methoxypropene; 4-chlorobenzaldehyde With ethylenediamine diacetic acid In 1,4-dioxane at 90℃; tandem Knoevenagel-hetero-Diels-Alder reaction;
Stage #2: With hydrogenchloride; silica gel In water; trifluoroacetic acid at 20℃;
81-82-3

coumachlor

14602-86-9

(1R,2S,5R)-menthyl chloroformate

Carbonic acid 3-[1-(4-chloro-phenyl)-3-oxo-butyl]-2-oxo-2H-chromen-4-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions
ConditionsYield
With TEA In 1,2-dichloro-ethane for 0.5h; Ambient temperature;100%
81-82-3

coumachlor

99-61-6

3-nitro-benzaldehyde

1253372-74-5

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

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;95%
81-82-3

coumachlor

141293-11-0, 141293-12-1

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

Conditions
ConditionsYield
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In chloroform; water at 35℃; for 0.25h;90%
81-82-3

coumachlor

104-88-1

4-chlorobenzaldehyde

1253372-72-3

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

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;90%
81-82-3

coumachlor

123-11-5

4-methoxy-benzaldehyde

1253372-73-4

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

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;90%
81-82-3

coumachlor

100-52-7

benzaldehyde

1253372-71-2

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

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;88%
98-01-1

furfural

81-82-3

coumachlor

1253372-75-6

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

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;85%
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Chemistry

IUPAC Name: 3-[1-(4-Chlorophenyl)-3-oxobutyl]-2-hydroxychromen-4-one 
Following is the structure of 2H-1-Benzopyran-2-one,3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy- (CAS NO.81-82-3):
                   
Empirical Formula: C19H15ClO4
Molecular Weight: 342.773 g/mol
EINECS: 201-378-1
Index of Refraction: 1.641
Molar Refractivity: 89.342 cm3
Molar Volume: 247.709 cm3
Density: 1.384 g/cm3
Flash Point: 282.262 °C
Melting point: 168-170 °C
Surface Tension: 60.061 dyne/cm
Enthalpy of Vaporization: 86.445 kJ/mol
Boiling Point: 543.108 °C at 760 mmHg
Product Categories of 2H-1-Benzopyran-2-one,3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy- (CAS NO.81-82-3): Pharmaceutical Intermediates
Water Solubility of 2H-1-Benzopyran-2-one,3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy- (CAS NO.81-82-3): 0.5 mg/L at 20 °C
Appearance of 2H-1-Benzopyran-2-one,3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy- (CAS NO.81-82-3): light yellow powder
Canonical SMILES: CC(=O)CC(C1=CC=C(C=C1)Cl)C2=C(OC3=CC=CC=C3C2=O)O
InChI: InChI=1S/C19H15ClO4/c1-11(21)10-15(12-6-8-13(20)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,23H,10H2,1H3
InChIKey: HENZOLWOIZODCT-UHFFFAOYSA-N

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 221mg/kg (221mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 30, Pg. 531, 1995.
mouse LD50 oral 392mg/kg (392mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 30, Pg. 531, 1995.
rat LD50 oral 187mg/kg (187mg/kg)   Pesticide Manual. Vol. 9, Pg. 186, 1991.
rat LD50 skin 33mg/kg (33mg/kg)   Pesticide Manual. Vol. 9, Pg. 186, 1991.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 48/22-52/53 
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 37-61 
S37:Wear suitable gloves. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 2
RTECS: GN4830000
HazardClass: 6.1(a)
PackingGroup: II

Specification

 2H-1-Benzopyran-2-one,3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxy- , its cas register number is 81-82-3. It also can be called Coumachlor ; 3-(1-(4-Chlorophenyl)-3-oxobutyl)-4-hydroxycoumarine ; and 3-(alpha-Acetonyl-p-chlorobenzyl)-4-hydroxycoumarin . Its classification code are Agricultural Chemical; Drug / Therapeutic Agent and Rodenticide.