• Name

  ACENOCOUMAROL

• EINECS 205-807-3
• CAS No. 152-72-7
• Article Data12
• CAS DataBase
• Density 1.427 g/cm³
• Solubility
• Melting Point 196-199 °C
• Formula C₁₉H₁₅NO₆
• Boiling Point 592.718 °C at 760 mmHg
• Molecular Weight 353.331
• Flash Point 312.265 °C
• Transport Information UN 2811
• Appearance White crystalline solid
• Safety 26-36/37
• Risk Codes 63-22-36/37/38
• Molecular Structure
• Hazard Symbols Xn
• Synonyms Acenocoumarol(6CI);Coumarin, 3-(a-acetonyl-p-nitrobenzyl)-4-hydroxy- (8CI);3-(Alpha-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;3-(a-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin;3-(a-p-Nitrophenyl-b-acetylethyl)-4-hydroxycoumarin;3-[a-(4'-Nitrophenyl)-b-acetylethyl]-4-hydroxycoumarin;3-[a-(p-Nitrophenol)-b-acetylethyl]-4-hydroxycoumarin;4-Hydroxy-2-oxo-3-[3-oxo-1-(4-nitrophenyl)butyl]-2H-chromene;Acenocoumarin;Acitrom;Ascumar;DL-3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;G 23,350;Minisintrom;Nicoumalone;Nitrowarfarin;Sinkumar;Sinthrome;Sintrom;Sintrom Mitis;Syncumar;Syntrom;Trombostop;Zotil;
• PSA 113.33000
• LogP 4.04100

Synthetic route

1076-38-6

4-hydroxy[1]benzopyran-2-one

946-49-6, 3490-37-7, 30625-98-0

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

152-72-7

acenocoumarol

Conditions

Conditions	Yield
With polystyrene-divinylbenzene support prepared with 2-ethylhexanoic acid as porogen with immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene at 100℃; for 72h; Reagent/catalyst; Michael Addition; Green chemistry;	96%
With N-ethyl-N,N-diisopropylamine In water for 18h; Michael Addition; Reflux;	96%

946-49-6, 3490-37-7, 30625-98-0

4-(p-nitrophenyl)-3-butene-2-one

1076-38-6

4-hydroxy[1]benzopyran-2-one

152-72-7

acenocoumarol

Conditions

Conditions	Yield
potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride In water for 2h; Product distribution; Heating; var. catalysts;	92%
potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride In water for 2h; Heating;	92%

1076-38-6

4-hydroxy[1]benzopyran-2-one

116-11-0

2-Methoxypropene

555-16-8

4-nitrobenzaldehdye

152-72-7

acenocoumarol

Conditions

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 2-Methoxypropene; 4-nitrobenzaldehdye 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℃;

...Expand

152-72-7

acenocoumarol

14602-86-9

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

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

Conditions

Conditions	Yield
With TEA In 1,2-dichloro-ethane for 0.5h; Ambient temperature;	100%

152-72-7

acenocoumarol

4-Hydroxy-3-[3-[(E)-hydroxyimino]-1-(4-nitro-phenyl)-butyl]-chromen-2-one

Conditions

Conditions	Yield
With pyridine; sodium hydroxide; hydroxylamine hydrochloride In ethanol 1) 12 h, 2) reflux, 6 h;	70%

67-56-1

methanol

152-72-7

acenocoumarol

2-methoxy-2-methyl-4-(4-nitro-phenyl)-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one

2-methoxy-2-methyl-4-(4-nitro-phenyl)-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one

Conditions

Conditions	Yield
With hydrogenchloride for 22h; Reflux;	A 12% B 64%

...Expand

152-72-7

acenocoumarol

108-24-7

acetic anhydride

4-acetoxy-3-<1-(4-nitrophenyl)-3-oxobutyl>-2H-1-benzopyran-2-one

Conditions

Conditions	Yield
for 1h; Heating;	49.4%

152-72-7

acenocoumarol

4'-Amino-warfarin

Conditions

Conditions	Yield
With hydrogen; nickel

152-72-7

acenocoumarol

4-[1-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-3-oxo-butyl]-benzenediazonium; chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney Ni 2: 1.) ice-bath, 1 h, 2.) 0 deg C, overnight View Scheme

Acenocoumarol Chemical Properties

Acenocoumarol Uses

Acenocoumarol Production

Acenocoumarol Toxicity Data With Reference

Acenocoumarol Safety Profile

Acenocoumarol Specification