127-71-9

Basic information

• Product Name: Sulfabenzamide
• Synonyms: N1-Benzoylsulfanilamide;Sulfabenzamide,N-(4-Aminobenzenesulfonyl)benzamide;Sulfabenzamide 1g [127-71-9];Sulfabenzamide (200 mg);Sulfabenzamide, 98.5%;SulfabenzaMide, USP;SulfabenzaMide, 98.5% 50GR;N-(Benzoyl)-4-aMinobenzenesulfonaMide
• CAS NO: 127-71-9
• Molecular Formula: C₁₃H₁₂N₂O₃S
• Molecular Weight: 276.31
• EINECS: 204-859-4
• Product Categories: Sulfonamides (Antibiotics for Research and Experimental Use);Aromatics;Sulfur & Selenium Compounds;SULFABENZIDE;Antibiotics for Research and Experimental Use;Biochemistry
• Mol File: 127-71-9.mol

Chemical Properties

• Melting Point: 180-184 °C
• Appearance: White to almost white/Powder
• Density: 1.3261 (rough estimate)
• Refractive Index: 1.6360 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.57(at 25℃)
• Water Solubility: 0.3 g/L (20 ºC)
• Merck: 14,8897
• BRN: 2139003
• CAS DataBase Reference: Sulfabenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfabenzamide(127-71-9)
• EPA Substance Registry System: Sulfabenzamide(127-71-9)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: 3249
• WGK Germany: 3
• RTECS: CV5802500
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 127-71-9(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white powder

Uses

Different sources of media describe the Uses of 127-71-9 differently. You can refer to the following data:
1. Has anti-bacterial activity.
2. It is used for the same indications, primarily in the form of ointments for vaginal infections. A synonym of this drug is sulfabenzide.

General Description

Chemical structure: sulfonamide

Synthesis

Sulfabenzamide, N1 -benzoylsulfanilamide (33.1.46), is synthesized just like sulfacetamide.

InChI:InChI=1/C13H12N2O3S/c14-11-6-8-12(9-7-11)19(17,18)15-13(16)10-4-2-1-3-5-10/h1-9H,14H2,(H,15,16)

Upstream product

• 93-99-2 benzoic acid phenyl ester 
• 63-74-1 sulfanilamide 
• 55871-46-0 benzyl 4-sulfamoylphenylcarbamate 
• 65-85-0 benzoic acid 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 55-21-0 benzamide 
• 1449004-77-6 benzyl 4-(N-benzoylsulfamoyl)phenylcarbamate 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 98-88-4 benzoyl chloride 
• 724423-50-1 N-benzoyl-sulfanilic acid benzoylamide 
• 5661-33-6 N-benzoyl-4-(acetamido)benzenesulfonamide 
• 623-11-0 1-methyl-4-nitrosobenzene 

Downstream Products

• 632622-54-9 4-{2-[5-chloro-2-(4-fluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-N-(1-phenyl-methanoyl)benzenesulfonamide 
• 632622-55-0 4-{2-[5-chloro-2-(2,4-difluoro-benzyloxy)-phenyl]-5-methyl-pyrrol-1-yl}-N-(1-phenyl-methanoyl)-benzenesulfonamide 
• 632625-12-8 4-{2-[5-bromo-2-(benzyloxy)-phenyl]-5-methyl-pyrrol-1-yl}-N-(1-phenyl-methanoyl)-benzenesulfonamide 
• 1204290-27-6 N-(4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)phenylsulfonyl)benzamide 
• 1204290-33-4 N-(4-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)phenylsulfonyl)benzamide 
• 1204290-36-7 N-(4-(1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)phenylsulfonyl)benzamide 
• 1350967-14-4 1,2-(trifluoroacetoxy)-3,4-di(p-sulfonamoylphenylimino)cyclobut-2-ene 
• 1350966-61-8 C₂₀H₁₅FN₂O₃S 
• 1350966-11-8 C₃₀H₂₂N₄O₈S₂ 
• 1290142-72-1 N-butyl-N-(4-aminophenylsulfonyl)benzamide 
• 1290142-73-2 N-pentyl-N-(4-aminophenylsulfonyl)benzamide 
• 1290142-66-3 N-trideuteromethyl-N-(4-di(trideuteromethyl)aminophenylsulfonyl)benzamide 

Relevant articles and documents

A STUDY OF TRANSMISSION EFFECTS OF SULFONYL AND CARBONYL GROUPS

Seventeen p-substituted N-phenylsulfonylbenzamides of general formulas XC6H4SO2NHCOC6H5 and C6H5SO2NHCOC6H4X have been synthesized and their structure has been confirmed by elemental analysis and 1H NMR spectra.The dissociation constants of all compounds have been measured by potentiometric titration in methanol, acetonitrile, dimethylformamide, dimethyl sulfoxide, and pyridine.The obtained pKHA values have been correlated with three sets of Hammett substituent constants using simple or double linear regression.The solvent and substituent effects are discussed on the basis of experimental results, and the difference between the substituent effects from sulfonamide and benzamide sections is evaluated.It has been found that due to extensive delocalization of negative charge in the conjugated base the transmission effects of carbonyl and sulfonyl groups on the transmission of substituent effect are roughly the same.The experimental data have been interpreted by the methods with latent variables: the principal component analysis (PCA), the conjugated deviation analysis (CDA), and the method of projection to latent structures (PLS).The results obtained by these procedures were similar.

Structure-activity relationships of agonists for the orphan G protein-coupled receptor GPR27

GPR27 belongs, with GPR85 and GPR173, to a small subfamily of three receptors called “Super-Conserved Receptors Expressed in the Brain” (SREB). It has been postulated to participate in key physiological processes such as neuronal plasticity, energy metabolism, and pancreatic β-cell insulin secretion and regulation. Recently, we reported the first selective GPR27 agonist, 2,4-dichloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (I, pEC50 6.34, Emax 100%). Here, we describe the synthesis and structure-activity relationships of a series of new derivatives and analogs of I. All products were evaluated for their ability to activate GPR27 in an arrestin recruitment assay. As a result, agonists were identified with a broad range of efficacies including partial and full agonists, showing higher efficacies than the lead compound I. The most potent agonist was 4-chloro-2,5-difluoro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7y, pEC50 6.85, Emax 37%), and the agonists with higher efficacies were 4-chloro-2-methyl-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7p, pEC50 6.04, Emax 123%), and 2-bromo-4-chloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7r, pEC50 5.99, Emax 123%). Docking studies predicted the putative binding site and interactions of agonist 7p with GPR27. Selected potent agonists were found to be soluble and devoid of cellular toxicity within the range of their pharmacological activity. Therefore, they represent important new tools to further characterize the (patho)physiological roles of GPR27.

Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

Human African trypanosomiasis (HAT) is one of the most neglected diseases in the tropic regions, which is fatal if not treated in time. There is an urgent need for new therapeutics, especially those in new chemical classes. Leucyl-tRNA synthetase (LeuRS) has been paid much attention as a recently clinically validated antimicrobial target. Our group has previously reported T. brucei LeuRS (TbLeuRS) inhibitors, including benzoxaboroles targeting the editing site and pyrrolinones targeting the synthetic site. Here we report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of TbLeuRS inhibitors. The R1 and R2 groups, reminiscent of the leucyl and adenyl regions of aa-AMP and aa-AMS, were optimized to result in a significant 13-fold increase of inhibitory activity (compound 19, IC 50 = 13.7 μM). Aided by ligand-protein docking, the 1,3-substitution at the central phenyl ring was predicted and proved to give significantly improved activity (59, IC50 = 1.1 μM). This work provided a new scaffold for the exploration of novel inhibitors against TbLeuRS, which may become potential therapeutics for the treatment of HAT.

Synthesis, characterization, and copolymerization of a series of novel acid monomers based on sulfonimides for proton conducting membranes

The synthesis and characterization of a series of novel acid monomers based on sulfonimides with different acidities are described. Copolymerization of the acid monomers with acrylonitrile was carried out, and the proton exchange membranes were cast from solutions of the resulting copolymers. Flexible, mechanically strong, and transparent membranes with different equivalent weights could be prepared. The membranes with lower equivalent weights and higher acidities exhibited higher proton conductivity under humidifying conditions compared to those with higher equivalent weights and lower acidities. The membrane electrode assembly was fabricated using a synthesized sulfonimide copolymer. The H2/O2 fuel cell performance was tested in a single cell, which revealed potential applicability of the sulfonimide membranes to polymer electrolyte fuel cells.

Novel urea (thiourea) derivative and thermal recording sheet using same

Compounds of formula (I) : wherein A is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, hydroxy or nitro; R1, R2, and R3, which may be the same or different, are each hydrogen, C1-C4 alkyl, C1-C4 alkoxy, hydroxy or nitro, or R1 and R2 form, together with the carbon atoms to which they are attached, an aromatic ring; and Y is a sulphur or oxygen atom; and formula (II) : wherein B is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, hydroxy or nitro; R1, R2, and R3, which may be the same or different, are each hydrogen, C1-C4 alkyl, C1-C4 alkoxy, hydroxy or nitro, or R1 and R2 form, together with the carbon atoms to which they are attached, an aromatic ring; and Y is a sulphur of oxygen atom; are used in the color developing layer of a thermal recording sheet which comprises a basic colorless dye and an organic color developer.

Process for formulating a synthetic drug for use in animal feed, and resulting formulation

A method of formulating a synthetic drug for use in animal feed, for the purpose of reducing carry-over of the synthetic drug to subsequent lots of animal feed in the feed mill.