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Sulfamerazine

CAS No.127-79-7
Chemical Name:Sulfamerazine
CBNumber:CB0693512
Molecular Formula:C11H12N4O2S
Formula Weight:264.3
MOL File:127-79-7.mol

Sulfamerazine Property

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)
form Solid
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)
UNSPSC Code 41116107
NACRES NA.24

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :26-36/37
WGK Germany :2
RTECS :WP0750000
F :10
TSCA :Yes
HS Code :2935904000
Toxicity :LD50 oral in mouse: 25gm/kg

NFPA 704:

	1
0		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264-P270-P301+P312-P501

Sulfamerazine Price More Price(8)

Brand: Sigma-Aldrich(India)
Product number: S8876
Product name : Sulfamerazine
Purity: ReagentPlus?, ≥99.0%
Packaging: 50G
Price: ₹3171.73
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: S8876
Product name : Sulfamerazine
Purity: ReagentPlus?, ≥99.0%
Packaging: 250G
Price: ₹7350.18
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: S8876
Product name : Sulfamerazine
Purity: ReagentPlus?, ≥99.0%
Packaging: 500G
Price: ₹13574.55
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: PHR1577
Product name : Sulfamerazine
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹12004.93
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 46826
Product name : Sulfamerazine
Purity: VETRANAL?, analytical standard
Packaging: 250MG
Price: ₹5131.05
Updated: 2022/06/14
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Sulfamerazine Chemical Properties,Usage,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.