132276-87-0

Basic information

• Product Name: 2-(4-Methoxybenzenesulfonyl)acetonitrile
• Synonyms: 2-(4-Methoxybenzenesulfonyl)acetonitrile
• CAS NO: 132276-87-0
• Molecular Formula: C₉H₉NO₃S
• Molecular Weight: 211.24
• Mol File: 132276-87-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 110-112 °C
• Boiling Point: 429.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.279±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-(4-Methoxybenzenesulfonyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methoxybenzenesulfonyl)acetonitrile(132276-87-0)
• EPA Substance Registry System: 2-(4-Methoxybenzenesulfonyl)acetonitrile(132276-87-0)

Safety Data

• Hazardous Substances Data: 132276-87-0(Hazardous Substances Data)

Usage

Appearance

White to off-white solid
The compound's appearance is described as a white to off-white solid, which indicates its physical form and color.

Chemical structure

Nitrile group attached to a benzene ring substituted with a methoxy group and a sulfonyl group
The structure of the compound consists of a nitrile group (CN) bonded to a benzene ring that has a methoxy group (-OCH3) and a sulfonyl group (-SO2-) as substituents.

Common uses

Reagent in organic synthesis, specifically in the production of pharmaceuticals and agrochemicals
The compound is widely used as a reagent in organic synthesis, particularly for creating pharmaceuticals and agrochemicals, due to its unique structure and reactivity.

Versatile building block

Synthesis of various important compounds
2-(4-Methoxybenzenesulfonyl)acetonitrile is known for its ability to act as a versatile building block, which means it can be used to create a variety of other important compounds.

Potential hazard

Handle with caution and proper safety measures
As a potentially hazardous substance, 2-(4-Methoxybenzenesulfonyl)acetonitrile should be handled with care and appropriate safety measures to avoid any adverse effects or accidents.

Upstream product

• 107-14-2 chloroacetonitrile 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 696-62-8 para-iodoanisole 
• 79506-66-4 2-acetonitrile(4-methoxylphenyl)sulfane 
• 696-63-9 4-Methoxybenzenethiol 

Downstream Products

• 41024-54-8 2-(4-methoxyphenylsulfonyl)-1-phenylethanone 
• 1383563-63-0 [3-(4-methoxybenzenesulfonyl)thieno[2,3-e][1,2,3]triazolo-[1,5-a]pyrimidin-5-yl]thiophen-2-ylmethylamine 
• 1383563-57-2 3-(4-methoxybenzenesulfonyl)-4H-thieno[2,3-e][1,2,3]-triazolo[1,5-a]pyrimidin-5-one 
• 866870-48-6 C₁₆H₁₂N₄O₄S 
• 132276-76-7 3-Amino-4-(4-methoxy-benzenesulfonyl)-5-(4-nitro-phenylamino)-thiophene-2-carboxylic acid ethyl ester 
• 132276-19-8 (4-Methoxy-benzenesulfonyl)-[3-(4-nitro-phenyl)-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 
• 132276-75-6 3-Amino-5-(4-ethoxy-phenylamino)-4-(4-methoxy-benzenesulfonyl)-thiophene-2-carboxylic acid ethyl ester 
• 132276-77-8 3-Amino-5-(4-iodo-phenylamino)-4-(4-methoxy-benzenesulfonyl)-thiophene-2-carboxylic acid ethyl ester 
• 132276-21-2 (4-Methoxy-benzenesulfonyl)-[3-naphthalen-2-yl-4-oxo-thiazolidin-(2Z)-ylidene]-acetonitrile 

Relevant articles and documents

A Concise Route to 2-Sulfonylacetonitriles from Sodium Metabisulfite

A three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3-azido-2-methylbut-3-en-2-ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2-arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room temperature without the need of any catalysts or additives. Moreover, the synthetic utility of this method is demonstrated by the transformation of 2-arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-arylsulfonylethylamine. (Figure presented.).

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.