Product features Chemical properties Uses Production methods
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Sulfanilamide

Product features Chemical properties Uses Production methods
Product Name
Sulfanilamide
CAS No.
63-74-1
Chemical Name
Sulfanilamide
Synonyms
SN;Sulfonamide;4-AMINOBENZENESULFONAMIDE;PRONTOSIL;SULPHANILAMIDE;Sulphonamide;AVC;STREPTOCIDE;Sulfanilamid;Sulfonylamide
CBNumber
CB6212562
Molecular Formula
C6H8N2O2S
Formula Weight
172.2
MOL File
63-74-1.mol
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Sulfanilamide Property

Melting point:
164-166 °C(lit.)
Boiling point:
400.5±47.0 °C(Predicted)
Density 
1.08
vapor pressure 
0.00001 hPa (70 °C)
refractive index 
1.6490 (estimate)
storage temp. 
2-8°C
solubility 
5.37g/l
pka
pKa 10.65(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
form 
powder
color 
white to faintly beige
Odor
Odorless
PH Range
5.8 - 6.1 (0.5% aq.sol.)
PH
5.8-6.1 (5g/l, H2O, 20℃)
Water Solubility 
7.5 g/L at 25 ºC
λmax
257nm(H2O)(lit.)
Merck 
14,8925
BRN 
511852
InChIKey
FDDDEECHVMSUSB-UHFFFAOYSA-N
LogP
-0.620
CAS DataBase Reference
63-74-1(CAS DataBase Reference)
NIST Chemistry Reference
Benzenesulfonamide, 4-amino-(63-74-1)
EPA Substance Registry System
Sulfanilamide (63-74-1)
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Safety

Hazard Codes 
Xn
Risk Statements 
40
Safety Statements 
24/25-36-22
WGK Germany 
3
RTECS 
WO8400000
F 
10
TSCA 
Yes
HazardClass 
8
HS Code 
29350090
Hazardous Substances Data
63-74-1(Hazardous Substances Data)
Toxicity
LD50 orally in mice: 3.8 g/kg (Marshall)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H303May be harmfulif swallowed

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1633007
Product name
Sulfanilamide
Purity
97%
Packaging
1g
Price
$295
Updated
2024/03/01
Sigma-Aldrich
Product number
1632004
Product name
Sulfanilamide
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
5g
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
1.11799
Product name
Sulfanilamide
Purity
GR for analysis Reag. Ph Eur
Packaging
100g
Price
$281
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB1306346
Product name
ANTI-CHROMOGRANIN-C (CENTER) antibody produced in rabbit
Purity
purified immunoglobulin, buffered aqueous solution
Packaging
400μL
Price
$461
Updated
2023/01/07
TCI Chemical
Product number
S0119
Product name
Sulfanilamide
Purity
>99.0%(HPLC)(T)
Packaging
25g
Price
$21
Updated
2024/03/01
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Sulfanilamide Chemical Properties,Usage,Production

Product features

Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.Without it, bacteria cannot replicate.

  1. Mechanism of action: mechanism of action is to interfere with the synthesis of nucleic acids required for pathogenic microorganisms,making bacteria lack of nutrition and stop the growth, development and reproduction, having suppression killing effect on hemolytic streptococcus, staphylococcus and meningococcal.
  2. Pharmacodynamics: Oral easily absorbed from the gastrointestinal tract, widely distributed in the body, can penetrate the blood-brain barrier into the brain tissue, and can penetrate the placental barrier into the fetus. Rapid excretion, mainly excreted in metabolites from kidney.
  3. Clinical application: Mainly used for trauma infection caused by infection hemolytic streptococcus, staphylococcus, and local wound infections.
  4. Uses: Sulfanilamide is lower toxicity in sulfa drugs, can be applied for infants, pregnant women, pregnant women and during menstruation, but not in large doses. Having effects on hemolytic streptococcal infection (erysipelas, puerperal fever, tonsillitis), urinary tract infection (gonorrhea) and so; also the intermediate for synthesis of other sulfa drug (such as sulfa amidine, pyrimidine and sulfamethoxazole sulfa methoxy-triazine, etc. ).

Chemical properties

White granular or crystalline powder, odorless. Slightly bitter taste. Slightly soluble in water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerol, hydrochloric acid, sodium hydroxide and potassium hydroxide solution, insoluble in chloroform, ether, benzene, petroleum ether.

Uses

  1. Sulfanilamide is the main raw material for the synthesis of sulfa drugs.
  2. Used as a reagent to determine nitrite, also used in the pharmaceutical industry.
  3. Used as intermediates for the synthesis of other sulfa drugs, even for wound disinfection.
  4. Amino benzene sulfonamide is intermediate of herbicide asulam, as well as intermediate of sulfa medicine.
  5. Veterinary medicine, topical anti-inflammatory drugs, for analysis and detection.
  6. Wide spectrum antibacterial, having antibacterial effects on hemolytic streptococcus, Neisseria meningitidis, Staphylococcus aureus and other Gram-positive and negative bacteria. This product is topical application, it can be partially absorbed from the wound. For trauma infections of hemolytic streptococcus and staphylococcus. It can also be used to quickly stop the bleeding wound.

Production methods

There are several methods for their preparation.
1. Acetyl aniline used as raw material
The acetanilide reacts with chlorosulfonic acid at 40~50 ℃, and then cooled slowly, added to water for acid decomposition, while precipitation, dried and filtered to give acetaminophen chloride and ammoniated, ammoniated temperature is controlled at 40~45 ℃, hydrolysis, acidification.
2. Method of mixed diphenyl urea
Condensation of aniline and urea is single-phenylurea and diphenyl urea (called mixed urea), and then obtained from chlorosulfonated, amination, hydrolysis, acid precipitation. The reaction procedure is as follows.
(1)Condensation condensation of aniline hydrochloride and urea, at a temperature of 101~110 ℃ reaction for 3~4 h, obtaining mixed diphenyl urea.
(2)Chlorosulfonated Chlorine acid is pressed into the sulfonated pot, stirring cooling, when the temperature drops below 10 ℃, uniformly added mixed phenyl urea under stirring, the reaction temperature is gradually increased, the addition is completed, at the 46~50 ℃ insulation and mixing for 2 h, cooled to below 10 ℃, added water for acid decomposition. Controlling that the decomposition temperature does not exceed 15 ℃, after the addition of water continued stirring for 20min, then by precipitation, washed with water, obtaining mixed phenylurea chloride.
(3)Ammoniated 2% aqueous ammonia is put into ammoniated pan, cooled to 25 ℃, stirring and added into a mixing phenyl urea chloride, control the temperature at 40 ℃, insulation and reaction for 3h, obtaining ammoniated liquid.
(4)Hydrolysis and neutralization The amide is heated up to 90 ℃, is added 3% lye, continue to heat 108~112 ℃, hydrolysis for 5 h, and moved in the crystallization pot, added hydrochloric acid to neutralize crystals and the crystals are cooled to 20 ℃, crystallization, filtration, washed with water, dry, products are obtained.

Description

Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.

Chemical Properties

White granules or powder crystals, odorless. Taste slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, easily soluble in boiling water, glycerin, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene and petroleum ether.

Uses

Sulfonamide antibacterial Sulfanilamide is an antibacterial and used in the treatment of vaginal yeast infections. It is a competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid. It serves as an intermediate for the preparation of 2,6-disubstituted anilines by electrophilic substitution followed by removal of the sulfonamide blocking group by desulfonation with sulfuric acid.

Uses

Sulfanilamide is an antibacterial agent and antimicrobial agent of sulfonamide type (topical and vaginal).

Definition

ChEBI: Sulfanilamide is a sulfonamide in which the sulfamoyl functional group is attached to aniline at the 4-position. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, an antibacterial agent and a drug allergen. It is a substituted aniline, a sulfonamide antibiotic and a sulfonamide.

Preparation

Sulfonamide is synthesized from acetanilide by chlorosulfonation, amination, hydrolysis, and neutralization:
Acetanilide is reacted with chlorosulfonic acid at 40～50℃, then cooled, slowly added to water for acid decomposition, precipitated at the same time, dried and filtered to obtain p-acetamidobenzenesulfonyl chloride, and then subjected to ammoniation, and the amination temperature is controlled at 40～ 45 ℃, and then hydrolyzed, acidified to obtain sulfonamide.

brand name

Acetonal vaginal;Amidrin;Avc cream suppositoty;Avc/dienestrol;Avril;Azol polvo;Azol pomada;Buco pental;Buco regis;Chemiovis;Daromid;Defonamid;Dorsec;Expseptoplix;Faderma;Fricton;Gagaril sulfamida;Gynaedron;Instilin;Jacosulfon;Medeyol;Mentol sedans sulfamidad;Nasopomada;Odamida;Oestro-gyneadron;Otocaina;Otonasal;Otorrilan;Ovuthricinol;Oxidermiol;Paraseptol;Pental forte;Pentalmicina;Polvo sulfamida leti;Polvo sulfamida orrvan;Polvos wilfe;Pomada heridas;Pomada wilfe;Prontablin;Pulvi bacteramide;Pyodental;Pyodron;Quimpeamida;Rhinamide;Rino glucol sulf;Sulfacromo;Sulfonamid spuman;Sulfonamide-spuman-style;Sulfonanilamid;Sulfosellan-salbe;Ung. vemleigh.

World Health Organization (WHO)

Sulfanilamide, a sulfonamide anti-infective agent, was introduced in 1936 for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Sulfanilamide is still used in some countries as a pessaries or as vaginal cream.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 9, p. 71, 1961 DOI: 10.1248/cpb.9.71

Antimicrobial activity

Sulfanilamide is a sulfonamide antibiotic. It is bacteriostatic against Streptococci in vitro at a concentration of 20 μg/ml and inhibits the growth of 106 clinically isolated strains of Gonococcus. Sulfanilamide reduces the concentration of Streptococcus in rabbit plasma ex vivo following four doses of 20 ml of a 2% sulfanilamide solution. Sulfonamide class antibiotics, of which sulfanilamide is a member, are bacteriostatic and inhibit bacterial synthesis of dihydrofolic acid by competing with 4-aminobenzoic acid for binding to dihydropteroate synthase. Formulations containing sulfanilamide have been used to treat T. vaginalis infections.

General Description

White powder. pH of 0.5% aqueous solution: 5.8-6.1.

Air & Water Reactions

May be unstable if exposed for long periods air and light . Slightly water soluble.

Reactivity Profile

Sulfanilamide is an amino acid. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May react with azo and diazo compounds to generate toxic gases.

Fire Hazard

Flash point data for Sulfanilamide are not available but Sulfanilamide is probably combustible.

Biochem/physiol Actions

Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: A competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid.Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion, subcutaneous, and intravenous routes. Human teratogenic effects by unspecified route: developmental abnormalities of the blood and lymphatic systems (including the spleen and bone marrow). Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Sulfanilamide Preparation Products And Raw materials

Raw materials

Diphenylurea 2-BENZOYLACETANILIDE Ammonium hydroxide Aniline hydrochloride Motor benzol N-Acetylsulfanilyl chloride Chlorosulfonic acid Hydrochloric acid Sodium hydroxide Acetanilide Ammonia

Preparation Products

Sulfacetamide sodium 30% sulfaclozine 4-AMINO-N-(3-CHLOROPYRAZINYL)BENZENESULFONAMIDE 3,5-DICHLOROSULFANILAMIDE Sulfaquinoxaline Asulam Fluorescent Brightener DCB 2,6-Dibromoaniline 4-AMINO-N-(6-CHLORO-5-METHOXY-4-PYRIMIDINYL)BENZENESULFONAMIDE Sulfachloropyridazine sodium SULFACHLOROPYRIDAZINE Sulfaguanidine 1,2,3-Trifluoro-4-nitrobenzene 3,5-DIBROMOSULFANILAMIDE AZOCASEIN 2,6-Dichloroaniline
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Sulfanilamide Suppliers

Belgium 1 Brazil 1 Canada 2 China 483 Czech Republic 1 Europe 3 France 3 Germany 11 India 41 Japan 5 Singapore 1 Slovakia 1 South Korea 1 Switzerland 1 The Netherlands 2 United Kingdom 10 United States 67 USA 1 Global 635
-Zhejiang Chemsyn Pharm Co.,Ltd,
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Macheng jinxin biotechnology co., LTD
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View Lastest Price from Sulfanilamide manufacturers

Henan Suikang Pharmaceutical Co.,Ltd.
Product
Sulfanilamide 63-74-1
Price
US $0.00/kg
Min. Order
25kg
Purity
99%
Supply Ability
10tons
Release date
2024-04-25
Ouhuang Engineering Materials (Hubei) Co., Ltd
Product
Sulfanilamide 63-74-1
Price
US $5.00/kg
Min. Order
1kg
Purity
99.92%
Supply Ability
50000tons
Release date
2024-04-25
Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Sulphanilamide 63-74-1
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2024-04-03

63-74-1, SulfanilamideRelated Search:

N-Fluorobenzenesulfonimide 4-Methoxybenzoyl chloride Fomesafen Benzenesulfonamide 2-Aminobenzenesulfonamide 4-Dimethylaminobenzoic acid Sulfanilic acid 4-Aminobenzoic acid Benzocaine P-AMINOBENZAMIDE GLUTAMIC ACID p-Anisidine 4-Aminophenylboronic acid Cyclopropanesulfonamide Sulfathiazole FUMING SULFURIC ACID Celecoxib Impurity 24 Celecoxib Impurity 23 Celecoxib Impurity 17

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