Warfarin

Base Information

• Chemical Name: Warfarin
• CAS No.: 81-81-2
• Molecular Formula: C19H16O4
• Molecular Weight: 308.334
• Mol file: 81-81-2.mol

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;

Chemical Property of Warfarin

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 162-164 °C(lit.)
• Boiling Point: 515.155 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 188.828 °C
• PSA: 67.51000
• Density: 1.308 g/cm³
• LogP: 3.60960
• Storage Temp.: 2-8°C
• Water Solubility.: Practically insoluble

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,T+,Xn,F
• Statements: 61-48/25-52/53-28-21-36-20/21/22-11
• Safety Statements: 53-45-61-52-36/37-28-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of Warfarin

There total 61 articles about Warfarin 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: 100.0%

(S)-4-Methoxywarfarin (60431-20-1) → S-(-)-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 25 ℃; for 6h;

DOI:10.1021/ol0619157

Reference yield: 94.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + 1-Phenylbut-1-en-3-one (122-57-6) → R-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8) + S-(-)-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8)

Guidance literature:

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

DOI:10.1002/adsc.201300554

Reference yield: 94.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + 1-Phenylbut-1-en-3-one (122-57-6) → R-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8) + S-(-)-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8)

Guidance literature:

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

DOI:10.1002/adsc.201300554

upstream raw materials:

4-hydroxy[1]benzopyran-2-one

1-Phenylbut-1-en-3-one

(+/-)-Warfarin 4-methyl ether

2-methoxywarfarin

Downstream raw materials:

4'-Hydroxywarfarin

R-warfarin

S-(-)-warfarin

3-fluoro-3-(1-phenyl-3-oxobutyl)-2H-benzopyran-2,4-dione

Refernces

• 1、 Yuan, Yusheng,Yang, Liu,Liu, Shaopu,Yang, Jidong,Zhang, Hui,Yan, Jingjing,Hu, Xiaoli. "Enzyme-catalyzed Michael addition for the synthesis of warfarin and its determination via fluorescence quenching of L-tryptophan". . p. 183 - 188. Retrieved 2017.
• 2、 Velayutham Pillai,Rajeswari,Vidhyasagar. "Spectral assignments and structural studies of a warfarin derivative stereoselectively formed by tandem cyclization". . p. 447 - 454. Retrieved 2015.
• 3、 Shahnani, Mostafa,Sefidbakht, Yahya,Maghari, Shokoofeh,Mehdi, Ahmad,Rezadoost, Hassan,Ghassempour, Alireza. "Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study". supporting information. p. 1289 - 1298. Retrieved 2020/08/19.
• 4、 Arunachalam, Rajendran,Chinnaraja, Eswaran,Natarajan, Ramalingam,Samanta, Krishanu,Subramanian, Palani S.. "Enantioselective Michael Addition Reaction Catalysed by Enantiopure Binuclear Nickel(II) Close-Ended Helicates". . . Retrieved 2020/02/04.