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Sulfanilamide

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Name

Sulfanilamide

EINECS 200-563-4
CAS No. 63-74-1 Density 1.427 g/cm3
PSA 94.56000 LogP 2.27850
Solubility 7.5 g/L at 25 °C Melting Point 164-167 °C
Formula C6H8N2O2S Boiling Point 400.5 °C at 760 mmHg
Molecular Weight 172.208 Flash Point 196 °C
Transport Information N/A Appearance White to almost white crystalline powder
Safety 24/25-36-22 Risk Codes 40
Molecular Structure Molecular Structure of 63-74-1 (Sulfanilamide) Hazard Symbols HarmfulXn
Synonyms

Sulfanilamide (SN);Sulfanilamide(8CI);(4-(Aminosulfonyl)phenyl)amine;4-(Aminosulfonyl)aniline;4-Aminobenzenesulfonamide;4-Aminophenylsulfonamide;A-349;Albosal;Ambeside;Antistrept;Astreptine;Bactesid;Deseptyl;Dipron;Ergaseptine;Erysipan;Fourneau 1162;Gombardol;Infepan;NSC 7618;Neococcyl;Orgaseptine;PABS;Prontosil white;PronzinAlbum;Proseptine;Proseptol;Pysococcine;Ro 1-3354;Rubiazol A;Sanamid;Septamide Album;Septanilam;Septinal;Septoplex;Septoplix;Stramid;Strepamide;Strepsan;Streptasol;Streptocid;Streptocid album;Streptocide (white);Streptoclase;Strepton;Streptopan;Streptosil;Sulfamidyl;Sulfana;Sulfanalone;Sulfanidyl;Sulfanil;Sulfanilamide Vaginal Cream;Sulfonamide;Sulfonylamide;Sulphanilamide;Tolder;Whitestreptocide;p-Aminophenylsulfonamide;p-Anilinesulfonamide;p-Sulfamoylaniline;Sulfanilamide;

Article Data 103

Sulfanilamide Synthetic route

6325-93-5

p-nitrobenzenesulfonamide

63-74-1

sulfanilamide

Conditions
ConditionsYield
With hydrogen In methanol; ethyl acetate under 760.051 Torr; for 4h; Heating; Flow reactor; Green chemistry;99%
With maghemite-palladium nanocomposite; hydrogen In ethanol; ethyl acetate at 30℃; for 0.0125h;98%
With sodium tetrahydroborate In water at 20℃; for 0.5h; Green chemistry;98%
36326-86-0

4-azidobenzenesulfonamide

63-74-1

sulfanilamide

Conditions
ConditionsYield
With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction;99%
14860-69-6

(p-aminobenzene)sulfonyl azide

63-74-1

sulfanilamide

Conditions
ConditionsYield
With C24H21CuN3O3; sodium L-ascorbate In water; tert-butyl alcohol at 80℃; for 6h; Inert atmosphere;98%
With C27H34ClN2ORu(1+)*Cl(1-); sodium formate In aq. phosphate buffer at 37℃; for 24h; pH=7.4;
108-90-7

chlorobenzene

63-74-1

sulfanilamide

Conditions
ConditionsYield
Stage #1: chlorobenzene With chlorosulfonic acid; ammonium chloride In 1,2-dichloro-ethane at 55℃; for 4h;
Stage #2: With ammonia In water; 1,2-dichloro-ethane at 15 - 40℃; for 2h;
Stage #3: With copper(l) iodide In water; 1,2-dichloro-ethane at 160℃; for 12h; Reagent/catalyst; Temperature;
97.5%
57-67-0

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

A

722-27-0

bis(4-aminophenyl)disulfide

B

63-74-1

sulfanilamide

C

62-53-3

aniline

D

121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm;A n/a
B 4.4%
C 95.1%
D 2.7%
352542-64-4

tert-butyl (4-sulfamoylphenyl)carbamate

63-74-1

sulfanilamide

Conditions
ConditionsYield
With H-β zeolite In dichloromethane for 10h; Heating;91%
103-84-4

Acetanilid

63-74-1

sulfanilamide

Conditions
ConditionsYield
Stage #1: Acetanilid With chlorosulfonic acid; thionyl chloride; phosphorus pentoxide In tetrachloromethane at 60 - 90℃;
Stage #2: With ammonia In tetrachloromethane at 50℃; for 3h;
86.98%
Multi-step reaction with 3 steps
1.1: chlorosulfonic acid / 55 h / 40 °C
1.2: 3 h / 65 °C
2.1: ammonium hydroxide / 1,2-dichloro-ethane / 2.5 h / 15 - 40 °C / Large scale
3.1: sodium hydroxide / 3 h / 90 °C / Large scale
View Scheme
98-10-2

benzenesulfonamide

63-74-1

sulfanilamide

Conditions
ConditionsYield
With ammonia; dihydrogen peroxide In water; tert-butyl alcohol at 75℃; for 2h; Reagent/catalyst; Temperature; Molecular sieve;82.3%
2858-20-0

5-chloro-2,6-dimethyl-pyrimidin-4-ylamine

121-60-8

p-acetylaminobenzenesulfonyl chloride

A

54951-54-1

N-[4-(dimethylamino-4-ylsulfonyl)phenyl]acetamide

B

63-74-1

sulfanilamide

C

4015-18-3

Sulfaclomid

D

84729-42-0

C22H22ClN5O6S2

E

4049-04-1

4-(4'-Acetylaminobenzensulfonyl)amino-5-chlor-2,6-dimethylpyrimidin

Conditions
ConditionsYield
With trimethylamine In dichloromethane at 33 - 40℃; for 10h; Mechanism; Product distribution; further amines;A n/a
B n/a
C n/a
D 70%
E n/a
121-61-9

p-acetylaminobenzenesulfonamide

63-74-1

sulfanilamide

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol for 1h; Reflux;68%
With hydrogenchloride
With sodium hydroxide

Sulfanilamide Consensus Reports

SULFANILAMIDE's reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Sulfanilamide Specification

The IUPAC name of Sulfanilamide is 4-aminobenzenesulfonamide. With the CAS registry number 63-74-1 and EINECS 200-563-4, it is also named as Benzenesulfonamide, p-amino-. The product's categories are Sulfonamides (Antibiotics for Research and Experimental Use); Antibiotics for Research and Experimental Use; Biochemistry. It is white to almost white crystalline powder which is alightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerol, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene or petroleum ether. As an antibiotic, this chemical functions by competitively inhibiting (ie, by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA). Additionally, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of Sulfanilamide can be summarized as:
(1)ACD/LogP: -0.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.72; (4)ACD/LogD (pH 7.4): -0.72; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.66; (8)ACD/KOC (pH 7.4): 9.66; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 49 Å2; (13)Index of Refraction: 1.627; (14)Molar Refractivity: 42.8 cm3; (15)Molar Volume: 120.6 cm3; (16)Surface Tension: 63.7 dyne/cm; (17)Enthalpy of Vaporization: 65.13 kJ/mol; (18)Vapour Pressure: 1.27E-06 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 172.030648; (21)MonoIsotopic Mass: 172.030648; (22)Topological Polar Surface Area: 94.6; (23)Heavy Atom Count: 11; (24)Complexity: 211.

Preparation of Sulfanilamide:
It can be obtained by chlorosulfonation, amination, hydrolysis and neutralization of acetanilide.


Uses of Sulfanilamide: 
It is not only used as reagent in the determination of nitrite, but also used in the pharmaceutical industry. It is also the major raw material in the production of sulfonamides drug. What's more, it is used in organic synthesis. For example, it can react with furfural to get 4-(2-formyl-pyrrol-1-yl)-benzenesulfonic acid amide. This reaction needs reagent 2N-HCl and solvent ethanol by heating. The reaction time is 5 hours. The yield is 41%.


When you are using Sulfanilamide, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect. So people should not breathe dust and avoid contact with skin and eyes. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:O=S(=O)(c1ccc(N)cc1)N
2. InChI:InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) 
3. InChIKey:FDDDEECHVMSUSB-UHFFFAOYAI

The following are the toxicity data of Sulfanilamide:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 2gm/kg (2000mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 1079, 1966.
guinea pig LD50 oral 3130mg/kg (3130mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 82, Pg. 86, 1944.
mouse LD50 intraperitoneal 5mg/kg (5mg/kg)   Antibiotics Annual. Vol. 5, Pg. 886, 1957/1958.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Antibiotics Annual. Vol. 5, Pg. 972, 1957/1958.
mouse LD50 oral 3gm/kg (3000mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952.
mouse LD50 subcutaneous 2900mg/kg (2900mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
rabbit LD50 oral 1300mg/kg (1300mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 31(3), Pg. 11, 1966.
rat LD50 intravenous 1400mg/kg (1400mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950.
rat LD50 oral 3900mg/kg (3900mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1072, 1986.

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