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CAS No.: | 72-14-0 |
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Name: | Sulfathiazole |
Article Data: | 40 |
Molecular Structure: | |
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 |
Sulfathiazole
Conditions | Yield |
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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 |
2-(p-Carbomethoxyaminobenzenesulfamido)thiazole
Sulfathiazole
Conditions | Yield |
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With calcium hydroxide In water for 2h; Heating; | 74.5% |
Conditions | Yield |
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With copper; potassium carbonate at 180 - 200℃; |
Conditions | Yield |
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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; |
Conditions | Yield |
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With sodium hydroxide; iron(II) hydroxide | |
With hydrogenchloride; iron | |
With hydrogenchloride; tin |
Conditions | Yield |
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With hydrogenchloride | |
With sodium hydroxide | |
With sodium hydroxide In water at 65℃; for 2h; |
Conditions | Yield |
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With nitrobenzene | |
With sodium hydroxide | |
at 180 - 190℃; | |
Erhitzen bis zur Schmelze; |
4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide
Sulfathiazole
Conditions | Yield |
---|---|
With sodium hydroxide | |
With hydrogenchloride | |
With sodium hydroxide |
Conditions | Yield |
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With pyridine |
Sulfathiazole
Conditions | Yield |
---|---|
With sodium hydroxide; sodium dithionite |
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%.
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%.
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. |