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Sulfathiazole

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Name

Sulfathiazole

EINECS 200-771-5
CAS No. 72-14-0 Density 1.561 g/cm3
PSA 121.70000 LogP 3.26110
Solubility poorly soluble in water, soluble in acetone, diluted hydrochloric acid, ammonia water and aqueous alkali Melting Point 200-202 °C(lit.)
Formula C9H9N3O2S2 Boiling Point 479.5 °C at 760 mmHg
Molecular Weight 255.321 Flash Point 243.8 °C
Transport Information UN 3249 Appearance white to cream powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 72-14-0 (Sulfathiazole) Hazard Symbols IrritantXi
Synonyms

Sulfanilamide,N1-2-thiazolyl- (8CI);Sulfanilamide, N1-4-thiazolin-2-ylidene- (6CI,7CI);2-(Sulfanilylamino)thiazole;2-(p-Aminobenzenesulfonamido)thiazole;2-(p-Aminobenzenesulphonamido)thiazole;2-Sulfathiazole;4-Amino-N-2-thiazolylbenzenesulfonamide;4-[(1,3-Thiazol-2-yl)aminosulfonyl]aniline;Azoquimiol;Azoseptale;Chemosept;Ciba3714;Cibazol;Dulana;Eleudron;Enterobiocine;N-(Thiazol-2-yl)-4-aminobenzenesulfonamide;N1-(2-Thiazolyl)sulfanilamide;NSC 31812;NSC 683531;Norsulfazol;Planomide;Poliseptil;Sanotiazol;Sulfamul;Sulfanilamidothiazole;Sulfathiazol;Sulfavitina;Thiazamide;Thiozamide;Sulfathiazole (ST);

Article Data 40

Sulfathiazole Synthetic route

N,N-bis(4-acetamidobenzenesulfonyl)-2-aminothiazole

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With water; sodium hydroxide at 75℃; for 0.75h; Reflux;75%
Multi-step reaction with 2 steps
1: ammonium hydroxide / water; acetone / 2.5 h / 65 °C
2: sodium hydroxide / water / 2 h / 65 °C
View Scheme
33119-99-2

2-(p-Carbomethoxyaminobenzenesulfamido)thiazole

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With calcium hydroxide In water for 2h; Heating;74.5%
3034-53-5

2-bromo-1,3-thiazole

63-74-1

sulfanilamide

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With copper; potassium carbonate at 180 - 200℃;
96-50-4

2-thiazolylamine

98-60-2

4-chlorobenzenesulfonyl chloride

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With pyridine Erhitzen des Reaktionsprodukts mit Kupferchlorid und konz. NH3 unter Druck auf 160-180grad;
With pyridine Erhitzen des Reaktionsprodukts mit Kupferchlorid und konz. NH3 unter Druck auf 160-180grad;
473-42-7

Nisulfazole

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With sodium hydroxide; iron(II) hydroxide
With hydrogenchloride; iron
With hydrogenchloride; tin
127-76-4

4'-(thiazol-2-ylsulfamoyl)acetanilide

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With hydrogenchloride
With sodium hydroxide
With sodium hydroxide In water at 65℃; for 2h;
5664-51-7

2-sulfanilylamino-thiazole-5-carboxylic acid

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With nitrobenzene
With sodium hydroxide
at 180 - 190℃;
Erhitzen bis zur Schmelze;
2183-24-6

4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With sodium hydroxide
With hydrogenchloride
With sodium hydroxide
96-50-4

2-thiazolylamine

24939-24-0

4-aminobenzenesulfonyl chloride

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With pyridine
4-phenylazo-benzenesulfonic acid thiazol-2-ylamide

4-phenylazo-benzenesulfonic acid thiazol-2-ylamide

72-14-0

Sulfathiazole

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite

Sulfathiazole Specification

The Benzenesulfonamide,4-amino-N-2-thiazolyl-, with the CAS registry number 72-14-0, is also known as 2-(p-Aminobenzenesulfonamido)thiazole. It belongs to the product categories of Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds. Its EINECS number is 200-771-5. This chemical's molecular formula is C9H9N3O2S2 and molecular weight is 255.32. What's more, its systematic name is 4-Amino-N-(1,3-thiazol-2-yl)benzenesulfonamide. Its classification codes are: (1)Anti-Infective Agents; (2)Antibacterial; (3)Human Data; (4)Mutation data; (5)Reproductive Effect; (6)Tumor data. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from light. This chemical is mainly used to cure infectious diseases such as hemolytic streptococcus, meningococci and pneumonia. It is also used in biochemical research. It is an organosulfur compound that has been used as a short-acting sulfa drug. It once was a common oral and topical antimicrobial until less toxic alternatives were discovered.

Physical properties of Benzenesulfonamide,4-amino-N-2-thiazolyl- are: (1)ACD/LogP: 0.05; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.04; (4)ACD/LogD (pH 7.4): -0.34; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 24.90; (8)ACD/KOC (pH 7.4): 10.46; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 121.7 Å2; (13)Index of Refraction: 1.704; (14)Molar Refractivity: 63.489 cm3; (15)Molar Volume: 163.535 cm3; (16)Polarizability: 25.169×10-24cm3; (17)Surface Tension: 83.0879974365234 dyne/cm; (18)Density: 1.561 g/cm3; (19)Flash Point: 243.799 °C; (20)Enthalpy of Vaporization: 74.383 kJ/mol; (21)Boiling Point: 479.509 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by (4-thiazol-2-ylsulfamoyl-phenyl)-carbamic acid methyl ester by heating. This reaction will need reagent calcium hydroxide and solvent H2O with the reaction time of 2 hours. The yield is about 74.5%.

Benzenesulfonamide,4-amino-N-2-thiazolyl- can be prepared by (4-thiazol-2-ylsulfamoyl-phenyl)-carbamic acid methyl ester by heating

Uses of Benzenesulfonamide,4-amino-N-2-thiazolyl-: it can be used to produce N-(4-thiazol-2-ylsulfamoyl-phenyl)-succinamic acid. It will need solvent acetone. The yield is about 73%.

Benzenesulfonamide,4-amino-N-2-thiazolyl- can be used to produce N-(4-thiazol-2-ylsulfamoyl-phenyl)-succinamic acid

When you are using this chemical, please be cautious about it as the following:
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. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(Nc1nccs1)c2ccc(N)cc2
(2)Std. InChI: InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)
(3)Std. InChIKey: JNMRHUJNCSQMMB-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo unreported 250mg/kg/23D- (250mg/kg) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Journal of Pathology and Bacteriology. Vol. 59, Pg. 501, 1947.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   National Technical Information Service. Vol. AD277-689.
mouse LD50 intravenous 990mg/kg (990mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 164, 1959.
mouse LD50 oral 4500mg/kg (4500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 571, 1971.
mouse LD50 subcutaneous 1450mg/kg (1450mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 164, 1959.
rat LD50 intravenous 1370mg/kg (1370mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950.
rat LDLo intraperitoneal 1250mg/kg (1250mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 164, 1959.
rat LDLo parenteral 1gm/kg (1000mg/kg)   Acta Radiologica. Vol. 37, Pg. 258, 1952.

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