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| CAS No.: | 152-72-7 |
|---|---|
| Name: | ACENOCOUMAROL |
| Molecular Structure: | |
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| Formula: | C19H15NO6 |
| Molecular Weight: | 353.331 |
| 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; |
| EINECS: | 205-807-3 |
| Density: | 1.427 g/cm3 |
| Melting Point: | 196-199 °C |
| Boiling Point: | 592.718 °C at 760 mmHg |
| Flash Point: | 312.265 °C |
| Appearance: | White crystalline solid |
| Hazard Symbols: | Xn |
| Risk Codes: | 63-22-36/37/38 |
| Safety: | 26-36/37 |
| Transport Information: | UN 2811 |
| PSA: | 113.33000 |
| LogP: | 4.04100 |
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- 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 | 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 | 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 | 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℃; |
- 152-72-7
acenocoumarol
- 14602-86-9
(1R,2S,5R)-menthyl chloroformate
| Conditions | Yield |
|---|---|
| With TEA In 1,2-dichloro-ethane for 0.5h; Ambient temperature; | 100% |
- 152-72-7
acenocoumarol
| Conditions | Yield |
|---|---|
| With pyridine; sodium hydroxide; hydroxylamine hydrochloride In ethanol 1) 12 h, 2) reflux, 6 h; | 70% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride for 22h; Reflux; | A 12% B 64% |
| Conditions | Yield |
|---|---|
| for 1h; Heating; | 49.4% |
- 152-72-7
acenocoumarol
| Conditions | Yield |
|---|---|
| With hydrogen; nickel |
- 152-72-7
acenocoumarol
| 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 |
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Chemistry
Chemistry informtion about Acenocoumarol (CAS NO.152-72-7) is:
IUPAC Name: 2-Hydroxy-3-[1-(4-Nitrophenyl)-3-Oxobutyl]Chromen-4-One
Synonyms: 3-(Alpha-(4'-Nitrophenyl)-Beta-Acetylethyl)-4-Hydroxycoumarin ; 3-(Alpha-(P-Nitrophenol)-Beta-Acetylethyl)-4-Hydroxycoumarin ; 3-(Alpha-Acetonyl-4-Nitrobenzyl)-4-Hydroxycoumarin ; 3-(Alpha-Acetonyl-P-Nitrobenzyl)-4-Hydroxy-Coumari ; 3-(Alpha-Acetonyl-P-Nitrobenzyl)-4-Hydroxy-Coumarin ; 3-(Alpha-P-Nitrophenyl-Beta-Acetylethyl)-4-Hydroxycoumarin ; 4-Hydroxy-3-(1-(4-Nitrophenyl)-3-Oxobutyl)-2h-1-Benzopyran-2-On ; 4-Hydroxy-3-(1-(4-Nitrophenyl)-3-Oxobutyl)-2h-1-Benzopyran-2-One
Product Categories: Aromatics ; Chiral Reagents ; Heterocycles ; Intermediates & Fine Chemicals ; Pharmaceuticals
MF: C19H15NO6
MW: 353.33
EINECS: 205-807-3
Density: 1.427 g/cm3
Melting Point: 196-1990°C
Flash Point: 312.3 °C
Boiling Point: 592.7 °C at 760 mmHg
Vapour Pressure: 6.78E-15 mmHg at 25°C
Enthalpy of Vaporization: 92.95 kJ/mol
Following is the molecular structure of Acenocoumarol (CAS NO.152-72-7) is:
Uses
Acenocoumarol (CAS NO.152-72-7) can be used as R-Enantiomer of Acenocoumarol. Vitamin K antagonist; It is structurally similar to Warfarin and used as Anticoagulant.
Production
Raw materials are 4-Hydroxycoumarin-->4-Phenyl-1-butene .
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 115mg/kg (115mg/kg) | "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 6, 1989. | |
| mouse | LD50 | oral | 1470mg/kg (1470mg/kg) | Therapie. Vol. 11, Pg. 85, 1956. | |
| rat | LD50 | oral | 513mg/kg (513mg/kg) | "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 3, 1969. |
Safety Profile
Poison by intraperitoneal route. Moderately toxic by ingestion. A human teratogen by an unspecified route. When heated to decomposition it emits toxic fumes such as NOx. See also WARFARIN.
RIDADR: 2811
HazardClass: 6.1(b)
PackingGroup: III
Specification
Acenocoumarol (CAS NO.152-72-7) is a white crystalline solidis.It is an anticoagulant that functions as a vitamin K antagonist (like warfarin). It is a derivative of coumarin and is marketed under the brand names Sintrom and Sinthrome.