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Basic Information

Molecular Structure:
CAS No.:	72-14-0
Name:	Sulfathiazole
Article Data:	40

Formula:	C₉H₉N₃O₂S₂
Molecular Weight:	255.321
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);
EINECS:	200-771-5
Density:	1.561 g/cm³
Melting Point:	200-202 °C(lit.)
Boiling Point:	479.5 °C at 760 mmHg
Flash Point:	243.8 °C
Solubility:	poorly soluble in water, soluble in acetone, diluted hydrochloric acid, ammonia water and aqueous alkali
Appearance:	white to cream powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
Transport Information:	UN 3249
PSA:	121.70000
LogP:	3.26110

Synthetic route

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

: 72-14-0
Sulfathiazole

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With copper; potassium carbonate at 180 - 200℃;

: 96-50-4
2-thiazolylamine

: 98-60-2
4-chlorobenzenesulfonyl chloride

: 72-14-0
Sulfathiazole

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide
With hydrogenchloride
With sodium hydroxide

: 96-50-4
2-thiazolylamine

: 24939-24-0
4-aminobenzenesulfonyl chloride

: 72-14-0
Sulfathiazole

Conditions

Conditions	Yield
With pyridine

4-phenylazo-benzenesulfonic acid thiazol-2-ylamide: 4-phenylazo-benzenesulfonic acid thiazol-2-ylamide

: 72-14-0
Sulfathiazole

Conditions

Conditions	Yield
With sodium hydroxide; sodium dithionite

Raw Materials

96-50-4

24939-24-0

3034-53-5

121-60-8

473-42-7

63-74-1

Downstream Products

96-50-4

85-73-4

29817-76-3

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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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