Sulfamethizole supplier | CasNO.144-82-1

Name
SULFAMETHIZOLE
EINECS 205-641-1
CAS No. 144-82-1
Article Data14
CAS DataBase
Density 1.562g/cm³
Solubility Insoluble at 6.5, soluble at 7.5 x and SO_x. See also SULFONATES.
Risk Codes R43
Molecular Structure
Hazard Symbols
Synonyms Sulfanilamide,N1-(5-methyl-1,3,4-thiadiazol-2-yl)- (6CI,7CI,8CI); 2-Methyl-5-sulfanilamido-1,3,4-thiadiazole;2-Sulfanilamido-5-methyl-1,3,4-thiadiazole;4-Amino-N-(5-methyl-[1,3,4]thiadiazol-2-yl)benzenesulfonamide;5-Methyl-2-sulfanilamido-1,3,4-thiadiazole; Ayerlucil; Famet; Lucosil;Methazol; Microsul; N-(5-Methyl-1,3,4-thiadiazol-2-yl)-4-aminobenzenesulfonamide;N1-(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanilamide; Renasul; Rufol; Salimol;Sulfamethiazole; Sulfamethizol; Sulfamethizole; Sulfamethylthiadiazole;Sulfapyelon; Sulfstat; Sulfurine; Sulphamethizole; Tetracid; Thidicur;Thiosulfil; Thiosulfil Forte; Ultrasul; Urocydal; Urodiaton; Urolucosil;Urosulfin; VK 53
PSA 134.59000
LogP 2.96450

Synthetic route

: 349621-24-5
N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-nitrobenzenesulfonamide

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
With hydrogenchloride; iron In ethanol; water for 3h; Reflux;	100%

: 39719-87-4
N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
Stage #1: N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide With hydrogenchloride In water for 0.5h; Reflux; Stage #2: With sodium carbonate In water	72%
Stage #1: N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide With hydrogenchloride In water for 0.5h; Reflux; Stage #2: With sodium carbonate In water	72%
With hydrogenchloride
With sodium hydroxide

: 108-33-8
5-methyl-1,3,4-thiadiazol-2-amine

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
anschliessend Erwaermen mit Eisen in wss.-aethanol. HCl;

: 108-33-8
5-methyl-1,3,4-thiadiazol-2-amine

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
With pyridine anschliessend Erwaermen mit wss. NaOH;
With hydrogenchloride

: 2302-95-6
acetaldehyde thiosemicarbazone

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
With pyridine anschliessend Erwaermen mit Ca32 in wss.-alkal. Loesung;

: 75-36-5
acetyl chloride

1-acetyl-4-<N-acetyl-sulfanilyl>-thiosemicarbazide: 1-acetyl-4-<N-acetyl-sulfanilyl>-thiosemicarbazide

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
anschliessend Hydrolysieren mit Mineralsaeure;

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous HCl View Scheme
Multi-step reaction with 2 steps 1: pyridine / 1 h / 95 °C 2: hydrogenchloride / water / 0.5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: pyridine / 0 - 95 °C 2: hydrogenchloride / water / 0.5 h / Reflux View Scheme

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 144-82-1
sulfamethizole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane; pyridine / 2 h / 20 °C 2: hydrogenchloride / iron / ethanol; water / 3 h / Reflux View Scheme

: 144-82-1
sulfamethizole

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 4-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dimethyl sulfoxide; toluene Condensation;	100%

: 144-82-1
sulfamethizole

: methyl 3-formyl-5-iodobenzoate

: methyl 3-iodo-5-((4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenylamino)-methyl)benzoate

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;	99%

: 117-80-6
2,3-Dichloro-1,4-naphthoquinone

: 144-82-1
sulfamethizole

: 1204290-30-1
4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
In ethanol at 115℃; for 72h;	98%

: tetrafluoroboric acid

: 144-82-1
sulfamethizole

: 7632-00-0
sodium nitrite

: C9H8N5O2S2(1+)*BF4(1-)

Conditions

Conditions	Yield
In water at 0℃; for 0.75h; Inert atmosphere;	96%

...Expand

: 144-82-1
sulfamethizole

: 112-13-0
n-decanoyl chloride

: 1191951-65-1
N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide

Conditions

Conditions	Yield
With pyridine at 95℃; for 1h;	95%
With pyridine at 0 - 95℃;	95%

: 5034-74-2
5-bromo-3-methoxysalicylaldehyde

: 144-82-1
sulfamethizole

: (E)-4-((5-bromo-2-hydroxy-3-methoxy benzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 78℃; for 6h;	92%

: 144-82-1
sulfamethizole

: 920-46-7
Methacryloyl chloride

: methacryloyl sulfamethizole

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; for 1.5h; Cooling with ice;	91%

: 89-55-4
5-bromosalicyclic acid

: 144-82-1
sulfamethizole

: (E)-4-((5-bromo-2-hydroxybenzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 78℃; for 6h;	90%

: 81-84-5
1,8-Naphthalic anhydride

: 144-82-1
sulfamethizole

: 4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 10h;	85%

: 33987-02-9
4-chlorobenzoquinazoline

: 144-82-1
sulfamethizole

: 4-(benzo[g]quinazolin-4-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2yl)benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 24h; Reflux;	82%

: 28900-10-9
2-chloro-6-methylnicotinonitrile

: 144-82-1
sulfamethizole

: 4-(3-cyano-6-methylpyridin-2-ylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 18h; Reflux;	82%

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

: 144-82-1
sulfamethizole

: 107090-15-3
4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide

Conditions

Conditions	Yield
In methanol for 4h; Heating;	81%

: 64-17-5
ethanol

: 144-82-1
sulfamethizole

: 17422-74-1
3-Formylchromone

: 1449215-86-4
4-{[(2-ethoxy-4-oxo-2H-chromen-3(4H)ylidene)methyl]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid Heating;	81%

...Expand

: 144-82-1
sulfamethizole

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 4-{(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 6h; Reflux;	81%

: 144-82-1
sulfamethizole

: 99876-68-3
2-Chloromethyl-4(7)-nitro-benzimidazole

: 107090-22-2
N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(4-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide

Conditions

Conditions	Yield
In methanol for 4h; Heating;	80%

: 144-82-1
sulfamethizole

: methyl 3-formyl-5-(6-methoxypyridin-3-yl)benzoate

: methyl 3-(6-methoxypyridin-3-yl)-5-((4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenylamino)methyl)benzoate

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;	80%

: 6484-25-9
4-chloro-2-phenylquinazoline

: 144-82-1
sulfamethizole

: N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(2-phenylquinazolin-4-ylamino)benzenesulfonamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 22h; Reflux;	80%

: 144-82-1
sulfamethizole

: 127172-22-9
(E)-3-(N,N-dimethylamino)-1-(3,4-dimethoxyphenyl)-2-propen-1-one

: Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With acetic acid In ethanol for 22h; Reflux;	80%

: 144-82-1
sulfamethizole

: 57-06-7
N-allyl isothiocyanate

: C13H15N5O2S3

Conditions

Conditions	Yield
In butan-1-ol Heating;	79%

: 144-82-1
sulfamethizole

: 74-88-4
methyl iodide

: (Z)-N-(3,5-dimethyl-1,3,4-thiadiazol-2(3H)-ylidene)-4-(dimethylamino)benzenesulfonamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	79%

: 50-00-0
formaldehyd

: 144-82-1
sulfamethizole

: 418790-13-3
N-(4-carbamoylphenyl)nicotinamide

: N-[4-({[4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenylamino]-methyl}-carbamoyl)-phenyl]-nicotinamide

Conditions

Conditions	Yield
Stage #1: formaldehyd; N-(4-carbamoyl-phenyl)-nicotinamide With hydrogenchloride In methanol at 0℃; for 0.5h; pH=3.5; Stage #2: sulfamethizole Heating;	78%

...Expand

: 144-82-1
sulfamethizole

: 371756-61-5
((E)-3-(3-(dimethylamino)acryloyl))-2H-chromen-2-one

: (Z)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)benzenesulfonamide

Conditions

Conditions	Yield
In ethanol for 21h; Reflux;	77%

: 144-82-1
sulfamethizole

: (Z)-3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one

: (Z)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-(3-oxo-3-(10H-phenothiazine-2yl)prop-1-enylamino)benzenesulfonamide

Conditions

Conditions	Yield
In ethanol for 18h; Reflux;	77%

: 144-82-1
sulfamethizole

: 79-04-9
chloroacetyl chloride

: 24694-13-1
2-chloro-N-[4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-acetamide

Conditions

Conditions	Yield
With triethylamine In acetone at 20℃; Cooling with ice;	76%

: 14625-39-9
2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole

: 144-82-1
sulfamethizole

: 107090-30-2
N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide

Conditions

Conditions	Yield
In methanol for 4h; Heating;	73%

: 144-82-1
sulfamethizole

: 718604-99-0
4-propyl-phenyl isothiocyanate

: N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-{[(4-propylphenyl)carbamothioyl]amino}benzenesulfonamide

Conditions

Conditions	Yield
In acetone at 20 - 80℃; for 6.5h;	70%

: 144-82-1
sulfamethizole

: 108-24-7
acetic anhydride

: 5794-88-7
5-Bromo-2-aminobenzoic acid

: 4-(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
Stage #1: acetic anhydride; 5-Bromo-2-aminobenzoic acid for 4h; Reflux; Stage #2: sulfamethizole With acetic acid for 4h; Reflux;	70%

...Expand

: 144-82-1
sulfamethizole

: 108-24-7
acetic anhydride

: 635-21-2
5-chloroanthranilic acid

: 4-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
Stage #1: acetic anhydride; 5-chloroanthranilic acid for 4h; Reflux; Stage #2: sulfamethizole With acetic acid for 4h; Reflux;	69%

...Expand

Sulfamethizole Chemical Properties

Chemistry informtion about Sulfamethizole (CAS NO.144-82-1) is:
IUPAC Name: 4-Amino-N-(5-Methyl-1,3,4-Thiadiazol-2-Yl)Benzenesulfonamide
Synonyms: 4-Amino-N-[5-Methyl-1,3,4-Thiadiazol-2-Yl]-Benzenesulfonamide ; Labotest-Bb Lt00772293 ; Sulfamethylthiadiazole ; Sulfamethiazole ; Sulfamethizol ; Sulfamethizole ; Sulphamethizole ; N1-(5-Methyl-1,3,4-Thiadiazol-2-Yl)Sulfanilamide
MF: C₉H₁₀N₄O₂S₂
MW: 270.33
EINECS: 205-641-1
Density: 1.562 g/cm³
Melting Point: 210 °C
Flash Point: 259.1 °C
Boiling Point: 504.9 °C at 760 mmHg
Vapour Pressure: 2.56E-10 mmHg at 25°C
Enthalpy of Vaporization: 77.44 kJ/mol
Storage temp.: 2-8°C
Merck: 8916
Following is the molecular structure of Sulfamethizole (CAS NO.144-82-1) is:

Sulfamethizole Uses

Sulfamethizole (CAS NO.144-82-1) is used in the prevention and treatment of bacterial infections, diabetes mellitus, edema, hypertension, and gout. Sulfa drug includes:
Topical sulfonamides: sulfacetamide; silver sulfadiazine; mafenide;
Rapidly absorbed and eliminated sulfonamides: sulfisoxazole diolamine; sulfadiazine; sulfamethoxazole;
Hydrophylic sulfonamides: phtalylsulfacetamide; phtalylsulfathiazole; sulfasalazine; sulfaguanidine;
Long lasting sulfonamides: sulfadoxine;
Others: sulfamazole; sulfamazone; sulfametopirazine; sulfametoxypiridazine; sulfametrol; succinylsulfathiazole;

Sulfamethizole Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intramuscular	3668mg/kg (3668mg/kg)	Drugs in Japan Vol. 6, Pg. 388, 1982.
mouse	LD50	intraperitoneal	3290mg/kg (3290mg/kg)	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse	LD50	intravenous	1820mg/kg (1820mg/kg)	Drugs in Japan Vol. 6, Pg. 388, 1982.
mouse	LD50	oral	> 10gm/kg (10000mg/kg)	Drugs in Japan Vol. 6, Pg. 388, 1982.
mouse	LD50	subcutaneous	1210mg/kg (1210mg/kg)	"Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 111, 1969.
rat	LD50	intramuscular	4444mg/kg (4444mg/kg)	Drugs in Japan Vol. 6, Pg. 388, 1982.
rat	LD50	intravenous	2710mg/kg (2710mg/kg)	Drugs in Japan Vol. 6, Pg. 388, 1982.
rat	LD50	oral	3500mg/kg (3500mg/kg)	Yakugaku Zasshi. Journal of Pharmacy. Vol. 83, Pg. 778, 1963.
rat	LD50	subcutaneous	> 6560mg/kg (6560mg/kg)	Drugs in Japan Vol. 6, Pg. 388, 1982.

Sulfamethizole Consensus Reports

Reported in EPA TSCA Inventory.

Sulfamethizole Safety Profile

Moderately toxic by ingestion and subcutaneous routes. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and SO_x. See also SULFONATES.
Hazard Codes:
Irritant Xi
Risk Statements:
R43:May cause sensitization by skin contact.
Safety Statements:
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 2
RTECS: WP0875000

Sulfamethizole Specification

Sulfamethizole (CAS NO.144-82-1) is a sulfonamide antibiotic. It is a white to pale yellow crystalline powder.And it is insoluble in water. Flammability data is lacking for it. Also it is probably non-flammable.

Product Name

SULFAMETHIZOLE

Synthetic route

Sulfamethizole Chemical Properties

Sulfamethizole Uses

Sulfamethizole Toxicity Data With Reference

Sulfamethizole Consensus Reports

Sulfamethizole Safety Profile

Sulfamethizole Specification

Related Products

Hot Products