Sulfisoxazole supplier | CasNO.127-69-5

Name
Sulfisoxazole
EINECS 204-858-9
CAS No. 127-69-5
Article Data14
CAS DataBase
Density 1.411 g/cm³
Solubility Water: <0.1 g/100 mL at 22.5 °C
Melting Point 195 °C
Formula C₁₁H₁₃N₃O₃S
Boiling Point 482.207 °C at 760 mmHg
Molecular Weight 267.309
Flash Point 245.43 °C
Transport Information
Appearance white to cream powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3,4-Dimethyl-5-sulfanilamidoisoxazole;3,4-Dimethylisoaxazole-5-sulfanilimide;4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide;
PSA 106.60000
LogP 3.40940

Synthetic route

: 184644-22-2
N-(3,4-dimethylisoxazol-5-yl)-4-nitrobenzenesulfonamide

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
With acetic acid; zinc In acetonitrile at 0 - 20℃;	69%
With hydrogenchloride; zinc
With hydrogenchloride; zinc

: 122447-83-0
2-methyl-N-sulfanilyl-acetoacetamidine

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
With hydrogenchloride; hydroxylamine

: 4206-74-0
N4-Acetyl-N1-<3.4-dimethyl-5-isoxazolyl>-sulfanilamid

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
With hydrogenchloride
With sodium hydroxide
With sodium hydroxide In methanol Deacetylation; Heating;

: 19947-75-2
5-amino-3,4-dimethylisoxazol

: 24939-24-0
4-aminobenzenesulfonyl chloride

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
With pyridine

: 19947-75-2
5-amino-3,4-dimethylisoxazol

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: aq. NaOH / methanol / Heating View Scheme
Multi-step reaction with 2 steps 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 42 h 2: acetic acid; zinc / acetonitrile / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine / 25 °C / Inert atmosphere 2: sodium hydroxide; water / 2 h / 100 °C View Scheme

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

1.5-diamino-naphthalene hydrochloride: 1.5-diamino-naphthalene hydrochloride

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: aq. NaOH / methanol / Heating View Scheme

: 174079-07-3
(3,4-Dimethyl-isoxazol-5-yl)-carbamic acid tert-butyl ester

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: TFA / 20 °C 2: pyridine / 20 °C 3: aq. NaOH / methanol / Heating View Scheme

: 857728-49-5
2-methyl-3-oxo-butyrimidic acid ethyl ester

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: NH2OH+HCl View Scheme

: 108846-04-4
N-(N-acetyl-sulfanilyl)-2-methyl-acetoacetamidine

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NH2OH+HCl 2: aqueous NaOH View Scheme

: 63-74-1
sulfanilamide

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: NH2OH+HCl View Scheme

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 42 h 2: acetic acid; zinc / acetonitrile / 0 - 20 °C View Scheme

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 1: pyridine / 25 °C / Inert atmosphere 2: sodium hydroxide; water / 2 h / 100 °C View Scheme

: 4468-47-7, 128252-16-4
2-methyl-3-oxo-butyronitrile

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Na2CO3; SO2; HSO; NaNO2 3: aqueous NaOH View Scheme
Multi-step reaction with 3 steps 1: Na2CO3; SO2; HSO; NaNO2 3: aqueous NaOH View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; hydroxylamine 3: hydrogenchloride; zinc View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; hydroxylamine 3: sodium hydroxide View Scheme

: 19947-75-2
5-amino-3,4-dimethylisoxazol

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: sodium hydroxide / water View Scheme
Multi-step reaction with 2 steps 2: sodium hydroxide View Scheme

: 19947-75-2
5-amino-3,4-dimethylisoxazol

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 127-69-5
sulfisoxazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: hydrogenchloride; zinc View Scheme

: 98-03-3
thiophene-2-carbaldehyde

: 127-69-5
sulfisoxazole

: thiophene-2-carbaldehyde sulfisoxazole

Conditions

Conditions	Yield
In ethanol Heating;	92%
In ethanol for 4h; Heating;

: 1192-62-7
1-(2-furyl)-1-ethanone

: 127-69-5
sulfisoxazole

: 2-acetylfuran sulfisoxazole

Conditions

Conditions	Yield
In ethanol Heating;	90%
In ethanol for 4h; Heating;

: 127-69-5
sulfisoxazole

: 2949-22-6
Glycine ethyl ester isocyanate

: 166963-50-4
4-[N '-(Ethoxycarbonylmethyl)ureido]-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	90%

: 127-69-5
sulfisoxazole

: silver nitrate

: C11H12AgN3O3S

Conditions

Conditions	Yield
With potassium hydroxide In water at 20℃; for 2h;	90%

: 346-55-4
4-chloro-7-trifluoromethyl quinoline

: 127-69-5
sulfisoxazole

: 1489236-22-7
N-(3,4-dimethylisoxazol-5-yl)-4-(7-(trifluoromethyl)quinolin-4-ylamino)benzenesulfonamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 12h; Reflux;	89%

: 86-98-6
4,7-dichloroquinoline

: 127-69-5
sulfisoxazole

: 1449365-36-9
C20H17ClN4O3S

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 6h; Reflux;	88%

: 487-89-8
Indole-3-carboxaldehyde

: 127-69-5
sulfisoxazole

: N-(3,4-dimethylisoxazol-5-yl)-4-[(1H-indol-3-ylmethylene)amino]benzenesulfonamide

Conditions

Conditions	Yield
In ethanol Heating;	86%
In ethanol for 2h; Reflux;	83%
In ethanol for 4h; Heating;

: 33987-02-9
4-chlorobenzoquinazoline

: 127-69-5
sulfisoxazole

: 4-(benzo[g]quinazolin-4-ylamino)-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 24h; Reflux;	86%

: 127-69-5
sulfisoxazole

: 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-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide

Conditions

Conditions	Yield
With acetic acid In ethanol for 22h; Reflux;	86%

: 127-69-5
sulfisoxazole

: 100986-85-4
levofloxacin

: (S)−7-((4-(N-(3,4-dimethylisoxazol-5-yl)sulfamoyl)phenyl)imino)−9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)−2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In methanol for 2h; Microwave irradiation; Reflux;	85.73%

: 127-69-5
sulfisoxazole

: 80756-85-0
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

: (Z)-2-(2-aminothiazol-4-yl)-N-(4-(N-(3,4-dimethylisoxazol-5-yl)sulfamoyl)phenyl)-2-(methoxyimino)acetamide

Conditions

Conditions	Yield
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere;	83.1%

: 88-15-3
2-Acetylthiophene

: 127-69-5
sulfisoxazole

: 2-acetylthiophene sulfisoxazole

Conditions

Conditions	Yield
In ethanol Heating;	83%
In ethanol for 4h; Heating;

: 4-isothiocyanato-7-(triflouromethyl)quinoline

: 127-69-5
sulfisoxazole

: 1491007-12-5
(E)-N-(4-(N-(3,4-dimethylisoxazol-5-yl)sulfamoyl)phenyl)-N'-(7-(trifluoromethyl)quinolin-4-yl)carbamimidothioic acid

Conditions

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

: 127-69-5
sulfisoxazole

: 36140-83-7
1-cyanoacetyl-3,5-dimethylpyrazole

: 546090-57-7
2-cyano-N-(4-{[(3,4-dimethylisoxa-zole-5-yl)amino]sulfonyl}phenyl)acetamide

Conditions

Conditions	Yield
In 1,4-dioxane for 6h; Reflux;	82%
In 1,4-dioxane for 4h; Reflux;
In 1,4-dioxane

: 127-69-5
sulfisoxazole

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

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

Conditions

Conditions	Yield
In ethanol for 21h; Reflux;	81%

: 127-69-5
sulfisoxazole

: 90-02-8
salicylaldehyde

: 71308-95-7
(E)-N-(3,4-dimethylisoxazol-5-yl)-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide

Conditions

Conditions	Yield
With sodium acetate; acetic acid In ethanol for 4h; Heating;	80%
In ethanol for 4h; Heating;
With acetic acid In ethanol for 4h; Reflux;

: 127-69-5
sulfisoxazole

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

: 84819-63-6
2-hydroxy-1-naphthalidene-sulphafurazole

Conditions

Conditions	Yield
In ethanol Heating;	80%
In ethanol for 2h; Heating;

: 127-69-5
sulfisoxazole

: 93-91-4
1-phenylbutan-1,3-dione

: 275801-84-8
N-(3,4-Dimethyl-isoxazol-5-yl)-4-[(Z)-3-hydroxy-1-methyl-3-phenyl-prop-2-en-(E)-ylideneamino]-benzenesulfonamide

Conditions

Conditions	Yield
In ethanol Heating;	80%

: 884647-32-9
7-chloro-4-isothiocyanatoquinoline

: 127-69-5
sulfisoxazole

: 1449376-70-8
C21H18ClN5O3S2

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 18h; Reflux;	79%

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

: 127-69-5
sulfisoxazole

: N-(3,4-dimethylisoxazol-5-yl)-4-(2-phenylquinazolin-4-yl-amino)benzenesulfonamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 22h; Reflux;	77%

: 127-69-5
sulfisoxazole

: C11H9NO2S2

: C21H18N4O5S2

Conditions

Conditions	Yield
In acetic acid at 90℃; for 3h;	77%

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

: 127-69-5
sulfisoxazole

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

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 18h; Reflux;	76%

: 127-69-5
sulfisoxazole

: 3173-53-3
Cyclohexyl isocyanate

A: 166963-51-5
4-(N'-Cyclohexylureido)-N-(3,4-dimethyl-5-isoxazolyl)benzene sulfonamide

B: 4-(Phenylethynyl)-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

Conditions

Conditions	Yield
	A n/a B 75%

...Expand

: 127-69-5
sulfisoxazole

: ethyl 3-(4-chlorophenyl)-4-isothiocyanato-1H-pyrazol-5-carboxylate

: ethyl 3-(4-chlorophenyl)-3-(4-(N-(3,4-dimethyl[1,2]isooxazolo)sulfamoyl)phenyl)thioureido-1H-pyrazole-5-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Reflux;	75%

: 127-69-5
sulfisoxazole

: 108-24-7
acetic anhydride

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

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

Conditions

Conditions	Yield
Stage #1: acetic anhydride; 5-Bromo-2-aminobenzoic acid for 4h; Reflux; Stage #2: sulfisoxazole With acetic acid for 4h; Reflux;	75%

...Expand

: 127-69-5
sulfisoxazole

: 36185-83-8
N'-(2-cyanophenyl)-N,N-dimethylimidoformamide

: N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-[(quinazolin-4-yl)amino]benzene-1-sulfonamide

Conditions

Conditions	Yield
With acetic acid at 100℃; for 3h;	74%

: 127-69-5
sulfisoxazole

: 1761-61-1
5-bromosalicyclaldehyde

: 58757-70-3
N4-(5-Bromosalicylidene)-N1-(3,4-dimethyl-5-isoxazolyl)sulfanilamide

Conditions

Conditions	Yield
In ethanol for 3h; Reflux;	73%

: 127-69-5
sulfisoxazole

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: (E)-N-(3,4-dimethylisoxazol-5-yl)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzenesulfonamide

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 24h; Inert atmosphere; Reflux;	72%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 127-69-5
sulfisoxazole

: (E)-N-(3,4-dimethylisoxazol-5-yl)-4-((2-hydroxy-4-methoxybenzylidene)amino)benzenesulfonamide

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 24h; Inert atmosphere; Reflux;	72%

: 127-69-5
sulfisoxazole

: 100-10-7
4-dimethylamino-benzaldehyde

: (Z)-4-((4-(diethylamino)benzylidene)amino)-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 24.25h; Reflux;	72%

Sulfisoxazole Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 347.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 ,1980,p. 275.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 ,1980,p. 275.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (gavage); No Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-138 ,1979. . Reported in EPA TSCA Inventory.

Sulfisoxazole Specification

The Sulfisoxazole, also known as 3,4-Dimethyl-5-sulfanilamidoisoxazole, is sulfonamide antibacterial with the formula C₁₁H₁₃N₃O₃S. It belongs to the product category of Endothelin Receptor. Its EINECS registry number is 204-858-9. With the CAS registry number 127-69-5, its IUPAC name is 4-amino-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide. It is sometimes given in combination with erythromycin or phenazopyridine. It is used locally in a 4% solution or ointment.

Physical properties of Sulfisoxazole: (1)ACD/LogP: 1.01; (2)ACD/LogD (pH 5.5): 0.92; (3)ACD/LogD (pH 7.4): -0.22; (4)ACD/BCF (pH 5.5): 2.78; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 68.12; (7)ACD/KOC (pH 7.4): 4.98; (8)#H bond acceptors: 6; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.626; (12)Molar Refractivity: 67.07 cm³; (13)Molar Volume: 189.4 cm³; (14)Surface Tension: 66.3 dyne/cm; (15)Density: 1.411 g/cm³; (16)Flash Point: 245.4 °C; (17)Enthalpy of Vaporization: 74.71 kJ/mol; (18)Boiling Point: 482.2 °C at 760 mmHg; (19)Vapour Pressure: 1.86E-09 mmHg at 25°C.

Uses of Sulfisoxazole: it can be used to produce N-salicylidene-sulfanilic acid-(3,4-dimethyl-isoxazol-5-ylamide) by heating. This reaction will need reagents anhydrous sodium acetate, glacial acetic acid and solvent ethanol with reaction time of 4 hours. The yield is about 80%.

Sulfisoxazole can be used to produce N-salicylidene-sulfanilic acid-(3,4-dimethyl-isoxazol-5-ylamide) by heating

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=C(ON=C1C)NS(=O)(=O)C2=CC=C(C=C2)N
(2)InChI: InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
(3)InChIKey: NHUHCSRWZMLRLA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	> 5gm/kg (5000mg/kg)	Drugs in Japan Vol. 6, Pg. 391, 1982.
mouse	LD50	intravenous	2500mg/kg (2500mg/kg)	Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.
mouse	LD50	oral	6800mg/kg (6800mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 1441, 1965.
rabbit	LD50	oral	20gm/kg (20000mg/kg)	Drugs in Japan Vol. 6, Pg. 391, 1982.
rat	LD50	oral	10gm/kg (10000mg/kg)	Drugs in Japan Vol. 6, Pg. 391, 1982.

Product Name

Sulfisoxazole

Synthetic route

Sulfisoxazole Consensus Reports

Sulfisoxazole Specification

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