Products Categories
CAS No.: | 75706-12-6 |
---|---|
Name: | Leflunomide |
Article Data: | 21 |
Molecular Structure: | |
Formula: | C12H9F3N2O2 |
Molecular Weight: | 270.211 |
Synonyms: | 4-Isoxazolecarboxamide, 5-methyl-N-(4-(trifluoromethyl)phenyl)-;N-(4-Trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide;Leflunomidum [INN-Latin];sell leflunomide;5-methyl-N-[4-(trifluoromethyl)phenyl]oxazole-4-carboxamide;5-Methylisoxazole-4-(4-trifluoromethyl) carboxanilide;Leflunamide;Isoxazole-4-carboxamide, 5-methyl-N-[4-(trifluoromethyl)phenyl]-;5-Methylisoxazole-4-carboxylic acid (4-trifluoromethyl)anilide;Arava;Leflunomida [INN-Spanish]; |
EINECS: | 616-254-6 |
Density: | 1.392 g/cm3 |
Melting Point: | 163-168 °C |
Boiling Point: | 289.3 °C at 760 mmHg |
Flash Point: | 128.8 °C |
Appearance: | off white crystalline solid |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 22-36/37/38 |
Safety: | 26-36 |
Transport Information: | UN 2811 6.1/PG 3 |
PSA: | 55.13000 |
LogP: | 3.32710 |
Leflunomide
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate In dichloromethane at 40℃; | 98% |
5-methyl-1,2-oxazole-4-carboxylic acid
4-trifluoromethylphenylamine
Leflunomide
Conditions | Yield |
---|---|
With triethylamine; 1,1'-carbonyldiimidazole In dichloromethane at 0℃; Reagent/catalyst; Heating; | 94% |
5-methylisoxazole-4-carbonyl chloride
4-trifluoromethylphenylamine
Leflunomide
Conditions | Yield |
---|---|
In diethyl ether for 0.5h; Ambient temperature; | 93% |
With sodium hydrogencarbonate In N,N-dimethyl acetamide; toluene | 86% |
With sodium hydrogencarbonate In water; toluene at 20 - 60℃; for 18h; | 43% |
4-trifluoromethylphenylamine
Leflunomide
Conditions | Yield |
---|---|
Stage #1: 5-methyl-1,2-oxazole-4-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 25 - 70℃; for 6h; Stage #2: 4-trifluoromethylphenylamine In toluene at 0 - 30℃; for 6h; | 62.34% |
Conditions | Yield |
---|---|
With copper; isopentyl nitrite In acetonitrile at 0 - 15℃; for 8h; Sandmeyer Reaction; Schlenk technique; Inert atmosphere; | 58% |
With copper; isopentyl nitrite In acetonitrile at 0 - 15℃; Sandmeyer Reaction; Inert atmosphere; | 58% |
5-methyl-1,2-oxazole-4-carboxylic acid
Leflunomide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / SOCl2 / 1 h / 70 °C 2: 93 percent / diethyl ether / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 4 h / 40 °C 2: triethylamine / dichloromethane / 0 °C 3: copper; isopentyl nitrite / acetonitrile / 8 h / 0 - 15 °C / Schlenk technique; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / 50 °C / Inert atmosphere 2: sodium hydrogencarbonate / water; toluene / 18 h / 20 - 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride / 45 °C 2: caesium carbonate / butanone; water / 1 h / 45 - 55 °C View Scheme |
4-trifluoromethylphenylamine
A
5-methylisoxazole-4-carbonyl chloride
B
Leflunomide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water |
Conditions | Yield |
---|---|
In acetonitrile |
5-methyl-1,2-oxazole-4-carboxylic acid
4-aminobenzotrifluoride hydrochloride
Leflunomide
Conditions | Yield |
---|---|
Stage #1: 5-methyl-1,2-oxazole-4-carboxylic acid With 1,1'-carbonyldiimidazole In neat (no solvent) for 0.333333h; Milling; Stage #2: 4-aminobenzotrifluoride hydrochloride In neat (no solvent) for 5h; Milling; | |
Stage #1: 5-methyl-1,2-oxazole-4-carboxylic acid With 1,1'-carbonyldiimidazole for 0.333333h; Milling; Green chemistry; Stage #2: 4-aminobenzotrifluoride hydrochloride for 5h; Milling; Green chemistry; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: copper; isopentyl nitrite / acetonitrile / 8 h / 0 - 15 °C / Schlenk technique; Inert atmosphere View Scheme |
The Leflunomide, with the CAS registry number 75706-12-6, is also known as 4-Isoxazolecarboxamide, 5-methyl-N-(4-(trifluoromethyl)phenyl)-; 5-Methylisoxazole-4-carboxylic acid (4-trifluoromethyl)anilide; Arava. It belongs to the product categories of Active Pharmaceutical Ingredients; API; Osteoarthritis and Rheumatoid Arthritis; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Cytokine signaling; Aromatics; Heterocycles; An immunosuppressive agent. This chemical's molecular formula is C12H9F3N2O2 and molecular weight is 270.21. What's more, its systematic name is 5-Methyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide. In addition, Leflunomide(CAS 75706-12-6) is off white crystalline solid which should be sealed in the container and stored in the cool and dry place.
Physical properties about Leflunomide are: (1)ACD/LogP: 2.287; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.29; (4)ACD/LogD (pH 7.4): 2.29; (5)ACD/BCF (pH 5.5): 32.22; (6)ACD/BCF (pH 7.4): 32.22; (7)ACD/KOC (pH 5.5): 417.95; (8)ACD/KOC (pH 7.4): 417.92; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 55.13 Å2; (13)Index of Refraction: 1.541; (14)Molar Refractivity: 61.024 cm3; (15)Molar Volume: 194.108 cm3; (16)Polarizability: 24.192×10-24 cm3; (17)Surface Tension: 40.5660018920898 dyne/cm; (18)Density: 1.392 g/cm3; (19)Flash Point: 128.771 °C; (20)Enthalpy of Vaporization: 52.861 kJ/mol; (21)Boiling Point: 289.311 °C at 760 mmHg; (22)Vapour Pressure: 0.0020000000949949 mmHg at 25°C.
Preparation of Leflunomide(CAS 75706-12-6): It can be produced by 5-methyl-isoxazole-4-carbonyl chloride and 4-trifluoromethyl-aniline. This reaction needs solvent diethyl ether at ambient temperature. The yield is 93%.
Uses of Leflunomide: It is a DMARD which is used in active moderate to severe rheumatoid arthritis and psoriatic arthritis. It is also an immunomodulatory drug inhibiting dihydroorotate dehydrogenase. It can relieve symptoms of rheumatoid arthritis and psoriatic arthritis. What's more, Leflunomide (CAS 75706-12-6) can be used to produce other chemicals. For example, it can react with dimethoxymethyl-dimethyl-amine to get dimethoxymethyl-dimethyl-amine. This reaction needs solvent dioxane. The yield is 60%.
When you are using this chemical, please be cautious about it as the following: Leflunomide (CAS 75706-12-6) is harmful if swallowed. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. So people should wear suitable protective clothing when contact it.
You can still convert the following datas of Leflunomide (CAS 75706-12-6) into molecular structure:
(1) SMILES:O=C(Nc1ccc(cc1)C(F)(F)F)c2c(onc2)C
(2) Std. InChI:InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)
(3) Std. InChIKey:VHOGYURTWQBHIL-UHFFFAOYSA-N
The following are the toxicity data of Leflunomide (CAS 75706-12-6) which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 185mg/kg (185mg/kg) | United States Patent Document. Vol. #5494911, | |
mouse | LD50 | oral | 445mg/kg (445mg/kg) | United States Patent Document. Vol. #5494911, | |
rat | LD50 | intraperitoneal | 170mg/kg (170mg/kg) | United States Patent Document. Vol. #5494911, | |
rat | LD50 | oral | 235mg/kg (235mg/kg) | United States Patent Document. Vol. #5494911, |