126891-45-0

Basic information

• Product Name: 4-BROMOBENZENESULPHONYLACETONITRILE
• Synonyms: AKOS BBS-00002850;4-BROMOBENZENESULFONYL ACETONITRILE;4-BROMOBENZENESULPHONYLACETONITRILE;IFLAB-BB F1673-4395;OTAVA-BB BB7119750093;4-BROMOBENZENESULFONYL ACETONITRILE, 90+%;[(4-Bromophenyl)sulphonyl]acetonitrile;4-Bromophenyl cyanomethyl sulphone
• CAS NO: 126891-45-0
• Molecular Formula: C₈H₆BrNO₂S
• Molecular Weight: 260.11
• Mol File: 126891-45-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 190-192°C
• Boiling Point: 438 °C at 760 mmHg
• Flash Point: 218.7 °C
• Appearance: /
• Density: 1.653 g/cm³
• Vapor Pressure: 7.16E-08mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 4-BROMOBENZENESULPHONYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOBENZENESULPHONYLACETONITRILE(126891-45-0)
• EPA Substance Registry System: 4-BROMOBENZENESULPHONYLACETONITRILE(126891-45-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 126891-45-0(Hazardous Substances Data)

Usage

General Description

4-Bromobenzenesulphonylacetonitrile is a chemical compound with the molecular formula C8H6BrNO2S. It is a white to off-white crystalline solid that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 4-BROMOBENZENESULPHONYLACETONITRILE is a key building block in the preparation of various sulfonamide and sulfonamide-based compounds, which are known for their antibacterial and antifungal properties. Additionally, 4-Bromobenzenesulphonylacetonitrile is also used in the production of dyes and other organic compounds. It is important to handle this compound with care, as it is considered to be hazardous and may cause skin and eye irritation upon contact.

InChI:InChI=1/C8H6BrNO2S/c9-7-1-3-8(4-2-7)13(11,12)6-5-10/h1-4H,6H2

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 107-14-2 chloroacetonitrile 
• 106-53-6 para-bromobenzenethiol 

Downstream Products

• 132275-67-3 2-(4-Bromo-benzenesulfonyl)-2-cyano-N-(4-ethoxy-phenyl)-thioacetamide 
• 1174392-13-2 C₁₅H₉BrN₄O₃S 
• 1174392-21-2 3-(4-bromobenzenesulfonyl)-4H-thieno[2,3-e][1,2,3]-triazolo[1,5-a]pyrimidin-5-one 
• 892749-46-1 [3-(4-bromobenzenesulfonyl)thieno[2,3-e][1,2,3]triazolo-[1,5-a]pyrimidin-5-yl]thiophen-2-ylmethylamine 
• 1174392-13-2 C₁₅H₉BrN₄O₃S 
• 132276-46-1 (4-Bromo-benzenesulfonyl)-[3-(4-nitro-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-82-5 3-Amino-4-(4-bromo-benzenesulfonyl)-5-p-tolylamino-thiophene-2-carboxylic acid ethyl ester 
• 132276-43-8 (4-Bromo-benzenesulfonyl)-[3-(4-ethoxy-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-42-7 (4-Bromo-benzenesulfonyl)-[3-(4-methoxy-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-45-0 (4-Bromo-benzenesulfonyl)-[3-(4-bromo-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-44-9 (4-Bromo-benzenesulfonyl)-[3-(4-chloro-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-41-6 (4-Bromo-benzenesulfonyl)-[4-oxo-3-p-tolyl-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-47-2 [3-Benzyl-4-oxo-thiazolidin-(2Z)-ylidene]-(4-bromo-benzenesulfonyl)-acetonitrile 
• 132276-40-5 (4-Bromo-benzenesulfonyl)-[4-oxo-3-phenyl-thiazolidin-(2Z)-ylidene]-acetonitrile 

Relevant articles and documents

Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation

Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, an aryl radical is generated in situ from aryl iodide, which undergoes subsequent sulfonylation via the insertion of sulfur dioxide leading to arylsulfonyl radical intermediates. Then the arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the corresponding 2-(arylsulfonyl)acetonitrile.

Nanomolar potency and metabolically stable inhibitors of kidney urea transporter UT-B

Urea transporters, which include UT-B in kidney microvessels, are potential targets for development of drugs with a novel diuretic ('urearetic') mechanism. We recently identified, by high-throughput screening, a triazolothienopyrimidine UT-B inhibitor, 1, that selectively and reversibly inhibited urea transport with IC50 = 25.1 nM and reduced urinary concentration in mice (Yao et al.J. Am. Soc. Nephrol., in press). Here, we analyzed 273 commercially available analogues of 1 to establish a structure-activity series and synthesized a targeted library of 11 analogues to identify potent, metabolically stable UT-B inhibitors. The best compound, {3-[4-(1,1-difluoroethyl)benzenesulfonyl]thieno[2,3-e][1,2,3]triazolo[1,5-a] pyrimidin-5-yl}thiophen-2-ylmethylamine, 3k, had IC50 of 23 and 15 nM for inhibition of urea transport by mouse and human UT-B, respectively, and ～40-fold improved in vitro metabolic stability compared to 1. In mice, 3k accumulated in kidney and urine and reduced maximum urinary concentration. Triazolothienopyrimidines may be useful for therapy of diuretic-refractory edema in heart and liver failure.