CAS No.81-81-2,Warfarin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	81-81-2
Name:	Warfarin
Article Data:	72

Formula:	C₁₉H₁₆O₄
Molecular Weight:	308.334
Synonyms:	Coumarin,3-(a-acetonylbenzyl)-4-hydroxy- (7CI,8CI);(RS)-Warfarin;1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone;3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin;3-(a-Acetonylbenzyl)-4-hydroxycoumarin;3-(a-Phenyl-b-acetylethyl)-4-hydroxycoumarin;4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one;Athrombine-K;Brumolin;Co-Rax;Compound 42;Coumafen;Coumaphen;Coumefene;DL-3-(a-Acetonylbenzyl)-4-hydroxycoumarin;Kumader;Kumadu;Ratron;Rodafarin;Rodafarin C;Rodex;Vampirinip II;Vampirinip III;W.A.R.F. 42;WARF compound 42;Warfarin;Zoocoumarin;rac-Warfarin;
EINECS:	201-377-6
Density:	1.308 g/cm³
Melting Point:	162-164 °C(lit.)
Boiling Point:	515.155 °C at 760 mmHg
Flash Point:	188.828 °C
Solubility:	Practically insoluble
Appearance:	crystalline solid
Hazard Symbols:	T
Risk Codes:	61-48/25-52/53
Safety:	53-45-61-52
Transport Information:	UN 2811 6.1/PG 1
PSA:	67.51000
LogP:	3.60960

Synthetic route

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With C23H24N2O6S*Li(1+) In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 48h; Reagent/catalyst; Michael Addition;	99%
With lipase In water at 50℃; for 168h; Temperature; Michael Addition; Enzymatic reaction;	99.1%
With N-ethyl-N,N-diisopropylamine In water for 20h; Michael Addition; Reflux;	93%

: 81-81-2
warfarin

Conditions

Conditions	Yield
With polystyrene-divinylbenzene support prepared cyclohexanol as porogen with immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene at 100℃; for 96h; Reagent/catalyst; Solvent; Temperature; Time; Michael Addition; Green chemistry;	96%
With L-proline In dimethyl sulfoxide at 20℃; for 15h; Michael addition;	85%
With rac-Pro-OH In dimethyl sulfoxide at 20℃; for 24h;	80%
With cetyltrimethylammonim bromide; 1,4-dihydropyridine-enolate In water at 20℃; for 10h; Michael addition;	50%

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 60-12-8
2-phenylethanol

: 516-06-3
D,L-valine

: 81-81-2
warfarin

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 16h;	84%

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 5381-93-1, 86734-67-0, 86734-69-2, 127707-68-0
1-hydroxy-1-phenyl-3-butanone

: 81-81-2
warfarin

Conditions

Conditions	Yield
With cyclopentene In chlorobenzene; toluene at 100℃; for 8h; Inert atmosphere; regioselective reaction;	83%

: 86795-49-5
3-(phenyl-λ3-iodanylidene)chromane-2,4-dione

: 1896-62-4
(E)-benzalacetone

: 81-81-2
warfarin

Conditions

Conditions	Yield
In acetonitrile at 80℃; for 12h;	76%

: 38063-51-3
(+/-)-Warfarin 4-methyl ether

: 81-81-2
warfarin

Conditions

Conditions	Yield
With boron tribromide In dichloromethane -78 up to 0 deg C;

: 102077-97-4
2-methoxywarfarin

: 81-81-2
warfarin

Conditions

Conditions	Yield
With boron tribromide In dichloromethane -78 up to 0 deg C;

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 7732-18-5
water

: 1896-62-4
(E)-benzalacetone

: 81-81-2
warfarin

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 116-11-0
2-Methoxypropene

: 100-52-7
benzaldehyde

: 81-81-2
warfarin

Conditions

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

...Expand

quat-ammonium salt: quat-ammonium salt

: 1896-62-4
(E)-benzalacetone

: 81-81-2
warfarin

Conditions

Conditions	Yield
In water

Raw Materials

1076-38-6

100-52-7

116-11-0

122-57-6

Downstream Products

129-06-6

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History

1. The early 1920s saw the outbreak of a previously unrecognized disease of cattle in the northern United States and Canada. Cattle would die of uncontrollable bleeding from very minor injuries, or sometimes drop dead of internal hemorrhage with no external signs of injury. In 1921, Frank Schofield, a Canadian veterinarian, determined that the cattle were ingesting moldy silage made from sweet clover that functioned as a potent anticoagulant.In 1929, North Dakota veterinarian Dr L.M. Roderick demonstrated that the condition was due to a lack of functioning prothrombin.
2. After an incident in 1951, where a US Army inductee unsuccessfully attempted suicide with warfarin and recovered fully,studies began in the use of warfarin as a therapeutic anticoagulant
3. A 2003 theory posits that warfarin was used by a conspiracy of Lavrenty Beria, Nikita Khrushchev and others to poison Soviet leader Joseph Stalin.

Specification

The CAS registry number of Warfarin is 81-81-2. The IUPAC name is 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one. Its EINECS registry number is 201-377-6. In addition, the molecular formula is C₁₉H₁₆O₄ and the molecular weight is 308.33. It is a kind of white to off-white crystalline powder and belongs to the classes of Coumarins; Insecticide; Intermediates & Fine Chemicals; Pharmaceuticals; Miscellaneous Compounds. And it is a synthetic derivative of dicoumarol, a 4-hydroxycoumarin-derived mycotoxin anticoagulant originally discovered in spoiled sweet clover-based animal feeds.

Physical properties about this chemical are: (1)ACD/LogP: 3.13 ; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 21; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 157; (7)ACD/KOC (pH 7.4): 3; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 63.6 Å²; (12)Index of Refraction: 1.635; (13)Molar Refractivity: 84.447 cm³; (14)Molar Volume: 235.758 cm³; (15)Polarizability: 33.477 ×10^-24cm³; (16)Surface Tension: 58.658 dyne/cm; (17)Density: 1.308 g/cm³; (18)Flash Point: 188.828 °C; (19)Enthalpy of Vaporization: 82.854 kJ/mol; (20)Boiling Point: 515.155 °C at 760 mmHg.

Preparation of Warfarin: it can be prepared by 4-hydroxy-chromen-2-one and 4-phenyl-but-3-en-2-one. This reaction will need catalyst triethylbenzylammonium chloride and solvent H₂O. The reaction time is 2 hours by heating. The yield is about 82%.

Warfarin can be prepared by 4-hydroxy-chromen-2-one and 4-phenyl-but-3-en-2-one

Uses of Warfarin: is used to decrease the tendency for thrombosis or as secondary prophylaxis (prevention of further episodes) in those individuals that have already formed a blood clot (thrombus). And is also used in antiphospholipid syndrome. It has been used occasionally after heart attacks (myocardial infarctions), but is far less effective at preventing new thromboses in coronary arteries. In addition, it can be used to get 3-fluoro-3-(3-oxo-1-phenyl-butyl)-chroman-2,4-dione. This reaction will need reagent (CF₃SO₂)₂NF and solvent CHCl₃ and H₂O. The reaction time is 15 minutes at reaction temperature of 35 °C. The yield is about 92%.

Warfarin can be used to get 3-fluoro-3-(3-oxo-1-phenyl-butyl)-chroman-2,4-dione

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed and may cause harm to the unborn child. And it has danger of serious damage to health by prolonged exposure. In addition, it is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. It is refer to special instructions/safety data sheets. Avoid exposure - obtain special instructions before use. During using it, not recommended for interior use on large surface areas. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). You should avoid release to the environment.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)CC(C\1=C(/O)c2ccccc2OC/1=O)c3ccccc3
(2)InChI: InChI=1/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
(3)InChIKey: PJVWKTKQMONHTI-UHFFFAOYAW

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD50	oral	6mg/kg (6mg/kg)		Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
chicken	LD50	oral	942mg/kg (942mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE LUNGS, THORAX, OR RESPIRATION: DYSPNEA BLOOD: HEMORRHAGE	Bulletin of Environmental Contamination and Toxicology. Vol. 37, Pg. 544, 1986.
dog	LD50	oral	3mg/kg (3mg/kg)		Defense des Vegetaux. Vol. 43(255-256), Pg. 20, 1989.
guinea pig	LD50	oral	180mg/kg (180mg/kg)		Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
human	LDLo	oral	6667ug/kg (6.667mg/kg)		Yakkyoku. Pharmacy. Vol. 28, Pg. 329, 1977.
man	TDLo	oral	10200ug/kg (10.2mg/kg)	BLOOD: HEMORRHAGE	"Clinical Memoranda on Economic Poisons," U.S. Dept. HEW, Public Health Service, Communicable Disease Center, Atlanta, GA, 1956Vol. -, Pg. 1, 1956.
mouse	LD50	intraperitoneal	750mg/kg (750mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 30, Pg. 531, 1995.
mouse	LD50	intravenous	165mg/kg (165mg/kg)		"Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 274, 1973.
mouse	LD50	oral	3mg/kg (3mg/kg)		Defense des Vegetaux. Vol. 43(255-256), Pg. 20, 1989.
mouse	LD50	unreported	60mg/kg (60mg/kg)		Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.
mouse	LDLo	subcutaneous	800mg/kg (800mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL)	Trudy, VNIIVS. Transactions of the All-Union Scientific Research Institute of Veterinary Sanitation. Vol. 58, Pg. 122, 1977.
pig	LD50	oral	1mg/kg (1mg/kg)		Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
rabbit	LD50	oral	800mg/kg (800mg/kg)		Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
rat	LC50	inhalation	320mg/m³ (320mg/m³)		Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 49, 1978.
rat	LD50	oral	1600ug/kg (1.6mg/kg)		Toxicology and Applied Pharmacology. Vol. 11, Pg. 327, 1967.
rat	LD50	skin	1400mg/kg (1400mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE KIDNEY, URETER, AND BLADDER: HEMATURIA BEHAVIORAL: MUSCLE WEAKNESS	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 49, 1978.
rat	LD50	unreported	50mg/kg (50mg/kg)		Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.
rat	LDLo	intraperitoneal	420mg/kg (420mg/kg)		Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
women	TDLo	oral	250ug/kg/2D-I (0.25mg/kg)	VASCULAR: STRICTIRA; CJAMGES OM VESSE;S	American Journal of Emergency Medicine. Vol. 16, Pg. 541, 1998.
women	TDLo	oral	15mg/kg/21W-I (15mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE BLOOD: CHANGE IN CLOTTING FACTORS	Southern Medical Journal. Vol. 75, Pg. 242, 1982.