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75706-12-6

Basic Information
CAS No.: 75706-12-6
Name: Leflunomide
Article Data: 21
Molecular Structure:
Molecular Structure of 75706-12-6 (Leflunomide)
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: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36
Transport Information: UN 2811 6.1/PG 3
PSA: 55.13000
LogP: 3.32710
Synthetic route

C40H45AuF6N4O2

75706-12-6

Leflunomide

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In dichloromethane at 40℃;98%
42831-50-5

5-methyl-1,2-oxazole-4-carboxylic acid

455-14-1

4-trifluoromethylphenylamine

75706-12-6

Leflunomide

Conditions
ConditionsYield
With triethylamine; 1,1'-carbonyldiimidazole In dichloromethane at 0℃; Reagent/catalyst; Heating;94%
67305-24-2

5-methylisoxazole-4-carbonyl chloride

455-14-1

4-trifluoromethylphenylamine

75706-12-6

Leflunomide

Conditions
ConditionsYield
In diethyl ether for 0.5h; Ambient temperature;93%
With sodium hydrogencarbonate In N,N-dimethyl acetamide; toluene86%
With sodium hydrogencarbonate In water; toluene at 20 - 60℃; for 18h;43%
455-14-1

4-trifluoromethylphenylamine

75706-12-6

Leflunomide

Conditions
ConditionsYield
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%
210627-03-5

N-(4-aminophenyl)-5-methylisoxazole-4-carboxamide

Umemoto's reagent

75706-12-6

Leflunomide

Conditions
ConditionsYield
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%
42831-50-5

5-methyl-1,2-oxazole-4-carboxylic acid

75706-12-6

Leflunomide

Conditions
ConditionsYield
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
455-14-1

4-trifluoromethylphenylamine

A

67305-24-2

5-methylisoxazole-4-carbonyl chloride

B

75706-12-6

Leflunomide

Conditions
ConditionsYield
With sodium hydrogencarbonate In water

4-methylisoxazole-4-carbonyl chloride

455-14-1

4-trifluoromethylphenylamine

75706-12-6

Leflunomide

Conditions
ConditionsYield
In acetonitrile
42831-50-5

5-methyl-1,2-oxazole-4-carboxylic acid

90774-69-9

4-aminobenzotrifluoride hydrochloride

75706-12-6

Leflunomide

Conditions
ConditionsYield
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;

C5H4ClNO3

106-50-3

1,4-phenylenediamine

75706-12-6

Leflunomide

Conditions
ConditionsYield
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
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    Chemical Name leflunomide Synonyms N-(4-trifluoromethyl-phenyl)-5-methylisoxazole-4-carboxamide;Leflunomidum;Arava;lefunamide;5-methyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide;Expan

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Specification

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%.

Leflunomide can be produced by 5-methyl-isoxazole-4-carbonyl chloride and 4-trifluoromethyl-aniline

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%.

Leflunomide can react with dimethoxymethyl-dimethyl-amine to get dimethoxymethyl-dimethyl-amine

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,

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