ChemicalBook >> CAS DataBase List >>Sulfanilamide

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
Molecular Weight:
172.2
MDL Number:
MFCD00007939
MOL File:
63-74-1.mol
MSDS File:
SDS
Last updated:2023-08-17 13:06:49

Sulfanilamide Properties

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
PH 5.8-6.1 (5g/l, H2O, 20℃)
Odor Odorless
PH Range 5.8 - 6.1 (0.5% aq.sol.)
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)
EWG's Food Scores 1-4
NCI Dictionary of Cancer Terms sulfonamide
FDA UNII 21240MF57M
ATC code D06BA05,J01EB06
NIST Chemistry Reference Benzenesulfonamide, 4-amino-(63-74-1)
EPA Substance Registry System Sulfanilamide (63-74-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS05
Signal word  Warning
Hazard statements  H303-H315-H314-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P260h-P301+P330+P331-P303+P361+P353
Hazard Codes  Xn
Risk Statements  40
Safety Statements  24/25-36-22
WGK Germany  3
RTECS  WO8400000
10
TSCA  Yes
HazardClass  8
HS Code  29350090
Toxicity LD50 orally in mice: 3.8 g/kg (Marshall)
NFPA 704
1
2 1

Sulfanilamide price More Price(62)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1633007 Sulfanilamide 97% 63-74-1 1g $295 2024-03-01 Buy
Sigma-Aldrich 1632004 Sulfanilamide United States Pharmacopeia (USP) Reference Standard 63-74-1 5g $436 2024-03-01 Buy
Sigma-Aldrich 1.11799 Sulfanilamide GR for analysis Reag. Ph Eur 63-74-1 100g $281 2024-03-01 Buy
Sigma-Aldrich SAB1306346 ANTI-CHROMOGRANIN-C (CENTER) antibody produced in rabbit purified immunoglobulin, buffered aqueous solution 63-74-1 400μL $461 2023-01-07 Buy
TCI Chemical S0119 Sulfanilamide >99.0%(HPLC)(T) 63-74-1 25g $21 2024-03-01 Buy
Product number Packaging Price Buy
1633007 1g $295 Buy
1632004 5g $436 Buy
1.11799 100g $281 Buy
SAB1306346 400μL $461 Buy
S0119 25g $21 Buy

Sulfanilamide Chemical Properties,Uses,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

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

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.

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.

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.

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.

121-61-9
63-74-1
Synthesis of Sulfanilamide from 4-Acetamidobenzenesulfonamide
Global( 630)Suppliers
Supplier Tel Email Country ProdList Advantage
Dayang Chem (Hangzhou) Co.,Ltd.
571-88938639 +8617705817739 info@dycnchem.com CHINA 52867 58
LEAP CHEM CO., LTD.
+86-852-30606658 market18@leapchem.com China 24738 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671 sales@tnjchem.com China 34572 58
Anhui Zhongda Biotechnology Co., Ltd
+8615689548120 linda@zhongda-biotech.com China 204 58
Shandong Huisheng Import & Export Co., Ltd.
+86-13176845580 +86-13176845580 da@zhongda-biotech.com China 248 58
Anhui Zhongda Biotechnology Co., Ltd
+8619956560829 justine@zhongda-biotech.com China 300 58
Anhui Ruihan Technology Co., Ltd
+8617756083858 daisy@anhuiruihan.com China 994 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9354 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60

Related articles

View Lastest Price from Sulfanilamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sulfanilamide pictures 2023-11-03 Sulfanilamide
63-74-1
US $0.00-0.00 / g 1g 99% 100000tons Anhui Zhongda Biotechnology Co., Ltd
Sulfanilamide pictures 2023-10-20 Sulfanilamide
63-74-1
US $90.00-70.00 / kg 1kg 99% 10000/month Anhui Zhongda Biotechnology Co., Ltd
Sulfanilamide pictures 2023-10-20 Sulfanilamide
63-74-1
US $90.00-70.00 / kg 1kg 99% 10000/month Anhui Zhongda Biotechnology Co., Ltd
  • Sulfanilamide pictures
  • Sulfanilamide
    63-74-1
  • US $0.00-0.00 / g
  • 99%
  • Anhui Zhongda Biotechnology Co., Ltd
  • Sulfanilamide pictures
  • Sulfanilamide
    63-74-1
  • US $90.00-70.00 / kg
  • 99%
  • Anhui Zhongda Biotechnology Co., Ltd
  • Sulfanilamide pictures
  • Sulfanilamide
    63-74-1
  • US $90.00-70.00 / kg
  • 99%
  • Anhui Zhongda Biotechnology Co., Ltd
p-amino-benzenesulfonamid p-Aminobenzensulfonamide p-Aminophenylsulfonamide Prontalbin Prontosil i Prontosil white prontosilalbum prontosili prontosilwhite Prontylin Pronzin album pronzinalbum Proseptal Proseptine Proseptol p-Sulfamidoaniline p-Sulfamoylaniline Pysococcine Rubiazol A SULFANILAMIDE (BEST QUALITY) sulfanilic amide Sulfanilamide crystalline 4-Aminobenzene sulphonamide SULFANILAMIDE STANDARD SOLUTION SULFANILAMIDE VETRANAL, 250 MG SULFANILAMIDE, 99+% SulfanilamideBp(Vet) SulphanilamideGr Sulfanilamide,Pharma SulphanilamideExtraPure Benzenesulfonamide, 4-amino- (9CI) Sulfanilamide,98% Sulfanilamide,97+% Sulfanilamide (technical) anilin-4-sufonic acid amide sulfanilamide solution 4-AMINOBENZENESULFONAMIDE(SULFANILAMIDE) PARA-AMINOBENZENESULPHONAMIDE SULPHONILAMIDE Sulfanilamide [for Diazotization Titration] SULFANILAMINE PURE Sulphanyl acid amide Sulfanilamide melting point standard CHGC EM66 SgII ANTI-CHROMOGRANIN-C (CENTER) antibody produced in rabbit SCG2 Secretogranin II Secretogranin-2 IndustrialSulfanilamide Sulfanilamide Melting Point Standard (1 g) (Approximately 165 degrees) Sulfanilamide solution,100ppm Sulfanilamide puriss. p.a., >=99% (calc. to the dried substance) Sulfanilamide Vetec(TM) reagent grade, 98% SULFANILAMIDE, VETEC 1162 F 1162f