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Sulfamerazine

CAS No.
127-79-7
Chemical Name:
Sulfamerazine
Synonyms
SMI;Sulphamerazine;A-310;rp2632;DEBENAL;2643-RP;Mebacid;Mesulfa;Romezin;RP 2632
CBNumber:
CB0693512
Molecular Formula:
C11H12N4O2S
Molecular Weight:
264.3
MDL Number:
MFCD00023212
MOL File:
127-79-7.mol
MSDS File:
SDS
Last updated:2024-04-02 22:45:52

Sulfamerazine Properties

Melting point 234-238°C
Boiling point 519.1±52.0 °C(Predicted)
Density 1.3364 (rough estimate)
refractive index 1.6440 (estimate)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
pka pKa 2.29(H2O t = 24.0 I = 0.5 (NaCl)) (Uncertain)
color White to Off-White
Water Solubility 202mg/L(20 ºC)
Merck 14,8913
BRN 249133
CAS DataBase Reference 127-79-7(CAS DataBase Reference)
FDA 21 CFR 556.660; 558.582; 558.4
FDA UNII UR1SAB295F
ATC code D06BA06,J01ED07
NIST Chemistry Reference Sulfamerazine(127-79-7)
EPA Substance Registry System Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)- (127-79-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36/37
WGK Germany  2
RTECS  WP0750000
10
TSCA  Yes
HS Code  2935904000
Toxicity LD50 oral in mouse: 25gm/kg
NFPA 704
1
0 0

Sulfamerazine price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 46826 Sulfamerazine VETRANAL , analytical standard 127-79-7 250mg $67.5 2024-03-01 Buy
Sigma-Aldrich 1628007 Sulfamerazine United States Pharmacopeia (USP) Reference Standard 127-79-7 500mg $381 2024-03-01 Buy
Alfa Aesar L04194 Sulfamerazine, 98+% 127-79-7 25g $21.8 2021-12-16 Buy
Alfa Aesar L04194 Sulfamerazine, 98+% 127-79-7 100g $58.4 2021-12-16 Buy
Sigma-Aldrich S8876 Sulfamerazine ReagentPlus , ≥99.0% 127-79-7 50g $65.3 2024-03-01 Buy
Product number Packaging Price Buy
46826 250mg $67.5 Buy
1628007 500mg $381 Buy
L04194 25g $21.8 Buy
L04194 100g $58.4 Buy
S8876 50g $65.3 Buy

Sulfamerazine Chemical Properties,Uses,Production

Chemical Properties

White Solid

Originator

Sulfamerazine,Lederle,US,1943

Uses

Antibacterial.This compound is a contaminant of emerging concern (CECs).

Definition

ChEBI: A sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position.

Manufacturing Process

To a well agitated solution of 6.95 grams of 2-amino-6-methyl pyrimidine in 40 cc of pyridine, 15 grams of p-acetylaminobenzenesulfonyl chloride are added in small portions over a 30 minute period. The reaction mixture is then heated on a steam bath for 30 minutes, the free pyridine being then removed under reduced pressure and the residue mixed with cold water, and the latter mixture is vigorously stirred. The solid reaction product is removed by filtration and washed with cold water.
There is obtained a yield of 14 grams of crude 2-(pacetylaminobenzenesulfonamido)- 6-methyl pyrimidine, which on recrystallization from alcohol and water melts at 238° to 239°C. The crude product is hydrolyzed by suspending it in 400 cc of 2 N hydrochloric acid and warming until solution is complete. The solution is neutralized with sodium carbonate and the precipitated 2-(sulfanilamido)-6-methyl pyrimidine is removed by filtration. The latter on recrystallization from alcohol and water shows a melting point of 225° to 226°C.

Therapeutic Function

Antibacterial

Antimicrobial activity

Like all examined sulfanilamides, this drug is effective in treating infections caused by streptococci, gonococci, pneumococci, staphylococci, and also colon bacillus. Synonyms of this drug are dosulfin, polagin, romezin, and others.

General Description

Chemical structure: sulfonamide

Pharmaceutical Applications

2-Sulfonamido-4-methylpyrimidine. A component of some triple sulfa combinations. Plasma half-life is c. 24 h and protein binding c. 75%. It is less active than sulfadiazine.

Safety Profile

Moderately toxic by intravenous and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NO, and SOx,.

Synthesis

Sulfamerazine, N1 -(4-methyl-2-pyrimidinyl)sulfanilamide (33.1.12), is also synthesized in the manner described above, which is by reacting 4-acetylaminobenzenesulfonyl chloride with 2-amino-4-methylpyrimidine (33.1.10), which is in turn synthesized by the traditional scheme of synthesizing derivatives of pyrimidine. Acetoacetic ester is condensed with guanidine to give 4-methyl-2-aminopyrimidin-6-one (33.1.8). Reacting this with phosphorous oxychloride gives 4-methyl-2-amino-6-chloropyrimidine (33.1.9). The chlorine atom at C6 of the pyrimidine ring is then removed by reduction with hydrogen using a palladium on carbon catalyst. The resulting 4-methyl-2-aminopyrimidine (33.1.10) is then reacted with 4-acetylaminobenzenesulfonyl chloride to make an acetanilide derivative (33.1.11), the subsequent hydrolysis of which with base leads to the formation of the desired sulfamerazine.

Synthesis_127-79-7

Sulfamerazine Preparation Products And Raw materials

Global( 276)Suppliers
Supplier Tel Email Country ProdList Advantage
Shaanxi TNJONE Pharmaceutical Co., Ltd
+86-13474506593 +86-13474506593 sarah@tnjone.com China 848 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21695 55
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679 +86-18949832763 info@tnjchem.com China 2989 55
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com China 2931 58
Xiamen AmoyChem Co., Ltd
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Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47465 58
Shaanxi Dideu Medichem Co. Ltd
18192627656 1012@dideu.com China 3504 58
SIMAGCHEM CORP
+86-13806087780 sale@simagchem.com China 17367 58

View Lastest Price from Sulfamerazine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sulphamerazine pictures 2024-04-02 Sulphamerazine
127-79-7
US $0.00 / kg 1kg 99% 1000kg Shaanxi TNJONE Pharmaceutical Co., Ltd
Sulfamerazine pictures 2024-03-16 Sulfamerazine
127-79-7
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Sulfamerazine pictures 2021-08-12 Sulfamerazine
127-79-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Sulphamerazine pictures
  • Sulphamerazine
    127-79-7
  • US $0.00 / kg
  • 99%
  • Shaanxi TNJONE Pharmaceutical Co., Ltd
  • Sulfamerazine pictures
  • Sulfamerazine
    127-79-7
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Sulfamerazine pictures
  • Sulfamerazine
    127-79-7
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
DEBENAL LABOTEST-BB LT00455132 METSULFA METHYLPYRIMAL 4-METHYL-2-SULFANILAMIDO-PYRIMIDINE 4-AMINO-N-[4-METHYL-2-PYRIMIDINYL]-BENZENESULFONAMIDE 4-AMINO-N-(4-METHYL-PYRIMIDIN-2-YL)-BENZENESULFONAMIDE 2-SULFANILAMIDO-4-METHYLPYRIMIDINE SulfaMerazine ReagentPlus(R), >=99.0% Sulfamerazine Solution, 100ppm Sulfamerazine Vetec(TM) reagent grade, 98% (p-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidin [German] Sulfamethyldiazine (sodium) Sulfamerazine solution,1000ppm 2(p-Aminobenzolsulfonamido)-4-methylpyrimidin Prestwick_17 SULFAMETHYLDIAZINE SULFAMERAZINE N1-(4-METHYLPYRIMIDIN-2-YL)SULFANILAMIDE PYRIMAL-M 2-Sulphanilamido-4-methylpyrimidine N1-(4-methylpyrimidin-2-yl)sulphanilamide SULFAMERAZINE PH FR-FU-USP Sulfamerazine solution SULFAMERAZINE STANDARD SOLUTION SULFAMERAZIN VETRANAL (4-AMINO-N-(4.METH SUSFAMERAZINE SULFAMERAZINE(SM1) (p-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidin 2-(4-Aminobenzenesulfonamido)-4-methylpyrimidine 2-(p-Aminobenzolsulfonamido)-4-methylpyrimidine 2632 R. P. 2643-RP 2-Sulfa-4-methylpyrimidine 4-amino-n-(4-methyl-2-pyrimidinyl)-benzenesulfonamid A-310 Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)- benzenesulfonamide,4-amino-N-(4-methyl-2-pyrimidinyl)- component of Sulfonamide Duplex Cremomerazine Debenal-M Kelamerazine Mebacid Mesulfa Methylsulfazin Methylsulfazine Metilsulfadiazin Metilsulfazin n-(4-methyl-2-pyrimidinyl) n-(4-methyl-2-pyrimidinyl)sulfanilamide N'-(4-Methyl-2-pyrimidyl) sulfanilamide N-(4-Methyl-2-pyrimidyl)sulfanilamide n(sup1)-(4-methyl-2-pyrimidinyl)-sulfanilamid N(sup1)-(4-Methyl-2-pyrimidinyl)sulfanilamide N1-(4-Methyl-2-pyrimidinyl)sulfanilamide Percoccide Pirimal-M Pyralcid