Nimesulide supplier | CasNO.51803-78-2

Name
Nimesulide
EINECS 257-431-4
CAS No. 51803-78-2
Article Data10
CAS DataBase
Density 1.451 g/cm³
Solubility Soluble in water (<50 µg/ml), 1:10 DMSO:PBS (pH 7.2) (<200 µg/ml), ethanol (1 mg/ml), DMSO (15 mg/ml), DMF (15 mg/ml), chloroform, dichloromethane, acetone (freely soluble), and 1N NaOH.
Melting Point 140-146 °C
Formula C₁₃H₁₂N₂O₅S
Boiling Point 442 °C at 760 mmHg
Molecular Weight 308.315
Flash Point 221.1 °C
Transport Information UN 2811 6
Appearance Yellow Needle-Like Crystals
Safety 36-26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 4'-Nitro-2'-phenoxymethansulfonanilid;Methanesulfonamide,N-(4-nitro-2-phenoxyphenyl)-;4-Nitro-2-phenoxy-methanesulfonanilide;Aulin;Flogovital;N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide;
PSA 109.60000
LogP 4.43560

Synthetic route

: sodium N-(methylsulfonyl)-N-(4-nitro-2-phenoxyphenyl)sulfamate

: 51803-78-2
nimesulide

Conditions

Conditions	Yield
With hydrogenchloride In water pH=~ 2;	100%

: 5422-92-4
1-amino-2-phenoxy-4-nitrobenzene

: 124-63-0
methanesulfonyl chloride

: 51803-78-2
nimesulide

Conditions

Conditions	Yield
Stage #1: 1-amino-2-phenoxy-4-nitrobenzene; methanesulfonyl chloride With triethylamine In dichloromethane at 20℃; for 23h; Cooling with ice; Stage #2: With sodium hydroxide In water for 16h; Reflux;	74.3%

: nimesulide radical anion

A: 51803-78-2
nimesulide

B: 4-nitrosonimesulide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; pH=9.0; Kinetics; Disproportionation;

: 51765-51-6
N-(2-Phenoxyphenyl)-methansulfonamid

: 51803-78-2
nimesulide

Conditions

Conditions	Yield
With sulfuric acid; nitric acid; acetic acid for 1h; Activation energy; Temperature;

: 121-88-0
2-Amino-5-nitrophenol

: 51803-78-2
nimesulide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetic acid / Reflux 2.1: copper diacetate; pyridine N-oxide; pyridine; oxygen / dichloromethane / 72 h / 20 °C / Molecular sieve 3.1: hydrazine hydrate / methanol / 6 h / Reflux 4.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice 4.2: 16 h / Reflux View Scheme

: 117346-07-3
2-(2-hydroxy-4-nitrophenyl)isoindoline-1,3-dione

: 51803-78-2
nimesulide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper diacetate; pyridine N-oxide; pyridine; oxygen / dichloromethane / 72 h / 20 °C / Molecular sieve 2.1: hydrazine hydrate / methanol / 6 h / Reflux 3.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice 3.2: 16 h / Reflux View Scheme

: 2-(4-nitro-2-phenoxyphenyl)isoindoline-1,3-dione

: 51803-78-2
nimesulide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / methanol / 6 h / Reflux 2.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice 2.2: 16 h / Reflux View Scheme

: 51803-78-2
nimesulide

: 51765-60-7
N-(4-amino-2-phenoxy phenyl) methanesulfonamide

Conditions

Conditions	Yield
With 5% Pd(II)/C(eggshell); hydrogen In ethyl acetate at 27℃; for 3h;	100%
With hydrogenchloride; tin In water at 90℃; for 3h;	100%
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;	97%

: 51803-78-2
nimesulide

: 74-88-4
methyl iodide

: 51765-67-4
N-Methyl-N-(4-nitro-2-phenoxy-phenyl)-methanesulfonamide

Conditions

Conditions	Yield
Stage #1: nimesulide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;	99%
With potassium carbonate In acetonitrile for 5h;	77%

: 51803-78-2
nimesulide

: C13H10(2)H2N2O5S

Conditions

Conditions	Yield
With [(1,5-cyclooctadiene)Ir(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)(PPh3)]PF6; deuterium In dichloromethane at 20℃; for 2h; Sealed tube;	96%

: 67969-82-8
tetrafluoroboric acid diethyl ether

: 51803-78-2
nimesulide

: 2,3,7,8-tetrafluorothianthrene-S-oxide

: C25H15F4N2O5S3(1+)*BF4(1-)

Conditions

Conditions	Yield
With 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;	93%

...Expand

: 67969-82-8
tetrafluoroboric acid diethyl ether

: 13755-29-8
sodium tetrafluoroborate

: 51803-78-2
nimesulide

: 2,3,7,8-tetrafluorothianthrene-S-oxide

: C25H15F4N2O5S3(1+)*BF4(1-)

Conditions

Conditions	Yield
Stage #1: tetrafluoroboric acid diethyl ether; nimesulide; 2,3,7,8-tetrafluorothianthrene-S-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube; Stage #2: sodium tetrafluoroborate In dichloromethane; water	93%

...Expand

: 51803-78-2
nimesulide

: silver nitrate

: 1364966-82-4
Ag-NMS

Conditions

Conditions	Yield
With KOH In water ligand, AgNO3, and KOH (1:1.1:1.1 molar ratio), stirred at room temp. for 1 h; ppt. filtered off, washed (water), dried (P2O5), elem. anal.;	89%

: 51803-78-2
nimesulide

: 100-39-0
benzyl bromide

: N-benzyl-N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	88%

: 51803-78-2
nimesulide

: 106-96-7
propargyl bromide

: 1601552-74-2
C16H14N2O5S

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃;	85%
Stage #1: nimesulide With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In acetone at 20℃; for 24h; Inert atmosphere;	80.6%

: 768-56-9
4-Phenyl-1-butene

: 51803-78-2
nimesulide

: N-(2-phenoxy-4-((1-phenylbutyl)amino)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With nickel(II) iodide; 6,6'-dimethyl-2,2'-bipyridine; (dimethoxy)methylsilane In N,N-dimethyl acetamide at 0 - 50℃; for 12.1667h; Inert atmosphere; Sealed tube; regioselective reaction;	83%

: 51803-78-2
nimesulide

: 4-nitro-2-phenoxymethanesulfonanilide sodium salt

Conditions

Conditions	Yield
With sodium In tetrahydrofuran for 4h; Heating;	79%
With sodium hydroxide In water at 45℃; for 1h; Temperature;

: 67-56-1
methanol

: 51803-78-2
nimesulide

: N-(4-(dimethylamino)-2-phenoxyphenyl)methanesulfonamide

Conditions

Conditions	Yield
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;	78%
With palladium 10% on activated carbon; potassium tert-butylate at 150℃; for 60h;

: 50-00-0
formaldehyd

: 51803-78-2
nimesulide

: N-(4-(methylamino)-2-phenoxyphenyl)methanesulfonamide

Conditions

Conditions	Yield
With hydrogen In 1,4-dioxane at 60℃; under 7500.75 Torr; for 24h; Autoclave;	77%

: 51803-78-2
nimesulide

: N-methyl-O-((4-nitrophenyl)sulfonyl)hydroxylammonium trifluoromethanesulfonate

A: N-(2-(4-(methylamino)phenoxy)-4-nitrophenyl)methanesulfonamide

B: N-(2-(2-(methylamino)phenoxy)-4-nitrophenyl)methanesulfonamide

Conditions

Conditions	Yield
With ferrous(II) sulfate heptahydrate at 40℃; for 16h; regioselective reaction;	A 64% B 10%

...Expand

: 51803-78-2
nimesulide

: 98-59-9
p-toluenesulfonyl chloride

: 4-methyl-N-(methylsulfonyl)-N-(4-nitro-2-phenoxyphenyl)benzenesulfonamide

Conditions

Conditions	Yield
With sodium carbonate In water at 35℃; pH=8 - 10;	56%

: 4857-04-9
2-chloromethyl-1H-benzimidazole

: 51803-78-2
nimesulide

: N-((1H-benzo[d]imidazol-2-yl)methyl)-N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

Conditions

Conditions	Yield
Stage #1: nimesulide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-chloromethyl-1H-benzimidazole In N,N-dimethyl-formamide at 25 - 60℃;	56%

: 53744-31-3, 7473-93-0
2-nitrochalcone

: 51803-78-2
nimesulide

: C28H23N3O4S

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; potassium carbonate In ethanol at 90℃; for 1h; Schlenk technique; Inert atmosphere;	54%

: 51803-78-2
nimesulide

: fenofibrate boronic acid

: isopropyl 2-methyl-2-(4-(4-(N-(4-(methylsulfonamido)-3-phenoxyphenyl)sulfamoyl)benzoyl)phenoxy)propanoate

Conditions

Conditions	Yield
With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	50%
With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere;	50%

: 51803-78-2
nimesulide

: C13H10(3)H2N2O5S

Conditions

Conditions	Yield
With tritium; [(1,5-cyclooctadiene)Ir(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)(PPh3)]PF6 In Isopropyl acetate at 20℃; for 4h;	12%

: 51803-78-2
nimesulide

A: 51765-60-7
N-(4-amino-2-phenoxy phenyl) methanesulfonamide

B: 109032-22-6
4-Hydroxy-Nimesulide

Conditions

Conditions	Yield
With sodium tetrahydroborate; oxygen; Cl8-5,10,15,20-tetraphenylporphyrinatoiron(III) chloride at 25℃; for 2h;	A 11 % Chromat. B 4.5 % Chromat.

: 51803-78-2
nimesulide

A: 51765-60-7
N-(4-amino-2-phenoxy phenyl) methanesulfonamide

B: 4-nitrosonimesulide

C: 503552-34-9
4-hydroxylamine nimesulide

Conditions

Conditions	Yield
With sodium tetrahydroborate; meso-tetraphenylporphyrin iron(III) chloride In methanol; dichloromethane at 20℃; for 1h; Product distribution; Further Variations:; Catalysts;

...Expand

: 51803-78-2
nimesulide

: 503552-34-9
4-hydroxylamine nimesulide

Conditions

Conditions	Yield
With ammonium chloride; zinc

: 51803-78-2
nimesulide

: 4-nitrosonimesulide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Zn; NH4Cl 2: potassium dichromate / 0 °C View Scheme

: 51803-78-2
nimesulide

: N-(4-Cyano-2-phenoxy-phenyl)-methanesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / H2 / 10percent Pd/C / ethanol / Ambient temperature 2: 1.) NaNO2, aq. HCl, 2.) NaCN / 1.) 5 deg C, 2.) H2O, benzene, from 0 to 40 deg C, 1.5 h View Scheme

: 51803-78-2
nimesulide

: N-[2-Phenoxy-4-(1H-tetrazol-5-yl)-phenyl]-methanesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / H2 / 10percent Pd/C / ethanol / Ambient temperature 2: 1.) NaNO2, aq. HCl, 2.) NaCN / 1.) 5 deg C, 2.) H2O, benzene, from 0 to 40 deg C, 1.5 h 3: 1.) Me3SnN3, 2.) silica gel / 1.) toluene, reflux, 24 h, 2.) MeOH, RT, 4 h View Scheme

Nimesulide Chemical Properties

IUPAC Name: N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide
Molecular Formula: C₁₃H₁₂N₂O₅S
Molecular Weight: 308.31 g/mol
Canonical SMILES: c1(c(ccc(c1)[N+](=O)[O-])NS(C)(=O)=O)Oc1ccccc1
InChI: InChI=1/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
EINECS: 257-431-4
Classification Code: Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory agents, non-steroidal; Antirheumatic Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Peripheral Nervous System Agents; Sensory System Agents
Product Categories: Active Pharmaceutical Ingredients; All Inhibitors;Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
Stability: Stable. Incompatible with strong oxidizing agents.
Index of Refraction: 1.638
Molar Refractivity: 76.32 cm³
Molar Volume: 212.3 cm³
Polarizability: 30.25×10^-24 cm³
Surface Tension: 62 dyne/cm
Density: 1.451 g/cm³
Flash Point: 221.1 °C
Enthalpy of Vaporization: 69.94 kJ/mol
Boiling Point: 442 °C at 760 mmHg
Melting Point: 140-146 °C
Storage temperature: 2-8 °C
Vapour Pressure of Nimesulide (CAS NO.51803-78-2): 5.19E-08 mmHg at 25 °C

Nimesulide History

Nimesulide (CAS NO.51803-78-2) was launched in Italy for the first time as Aulin and Mesulid in 1985. It has become a leading non-steroidal anti-inflammatory drug in over 50 countries worldwide. In 2002 nimesulide benefit/risk profile was reviewed by the EMEA following decision to temporarily suspend the drug from the market in March 2002.
Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.

Nimesulide Uses

Nimesulide (CAS NO.51803-78-2) is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.

Nimesulide Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	oral	100mg/kg/5W-I (100mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: "JAUNDICE, CHOLESTATIC" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Journal of Hepathology. Vol. 29, Pg. 135, 1998.
mouse	LD50	intraperitoneal	216mg/kg (216mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 1254, 1975.
mouse	LD50	oral	392mg/kg (392mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 1254, 1975.
rat	LD50	intraperitoneal	163mg/kg (163mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 1254, 1975.
rat	LD50	oral	200mg/kg (200mg/kg)		Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 34, Pg. 759, 1975.
women	TDLo	oral	2mg/kg (2mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: PROTEINURIS	Nephrology, Dialysis, Transplantation. Vol. 12, Pg. 1493, 1997.
women	TDLo	oral	84mg/kg/3W-I (84mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" BLOOD: EOSINOPHILIA	Journal of Hepathology. Vol. 29, Pg. 135, 1998.
women	TDLo	unreported	8mg/kg (8mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Allergy. Vol. 52(Suppl,

Nimesulide Safety Profile

Hazard Codes of Nimesulide (CAS NO.51803-78-2): Harmful Xn, Irritant Xi
Risk Statements: 22-36/37/38
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 36-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS of Nimesulide (CAS NO.51803-78-2): PB0970000

Nimesulide Specification

Nimesulide (CAS NO.51803-78-2), its Synonyms are 4'-Nitro-2'-phenoxymethansulfonanilid ; 4-Nitro-2-phenoxy-methanesulfonanilide ; Aulin ; Flogovital ; Mesulid ; N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide ; Nimed ; Nimesulida ; Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)- (9CI) ; Methanesulfonanilide, 4'-nitro-2'-phenoxy- . It is yellow needle-like crystals.

Product Name

Nimesulide

Synthetic route

Nimesulide Chemical Properties

Nimesulide History

Nimesulide Uses

Nimesulide Toxicity Data With Reference

Nimesulide Safety Profile

Nimesulide Specification

Related Products

Hot Products