308293-22-3

Basic information

• Product Name: 2-Thiophenesulfonamide, N-(phenylmethylene)-
• CAS NO: 308293-22-3
• Molecular Formula: C11H9NO2S2
• Molecular Weight: 251.33
• Mol File: 308293-22-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Thiophenesulfonamide, N-(phenylmethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenesulfonamide, N-(phenylmethylene)-(308293-22-3)
• EPA Substance Registry System: 2-Thiophenesulfonamide, N-(phenylmethylene)-(308293-22-3)

Safety Data

• Hazardous Substances Data: 308293-22-3(Hazardous Substances Data)

Upstream product

• 6339-87-3 2-thiophensulfonamide 
• 100-52-7 benzaldehyde 

Downstream Products

• 905991-76-6 (S)-methyl 2,2-dimethyl-3-phenyl-3-[(2-thienylsulfonyl)amino]propanoate 
• 1068150-88-8 methyl (5R,2E)-2-methyl-5-(phenyl)-5-(2-thienylsulfonyl)amino-2-pentenoate 
• 5422-81-1 (E)-3-phenyl-1-(piperidin-1-yl)-prop-2-en-1-one 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 905991-06-2 (R)-S-tert-butyl 3-phenyl-3-[(2-thienyl)sulfonyl]amino-3-propanethioate 

Relevant articles and documents

Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

The decarboxylative Mannich reaction between imines and substituted malonic acids half-oxyesters (SMAHOs) has been developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. The reaction proceeds under simple reaction conditions and toler

Catalytic asymmetric synthesis of dihydroquinazolinones from imines and 2-aminobenzamides

An unprecedented catalytic asymmetric synthesis of aminal-containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β- unsaturated, and aliphatic imines react with 2-aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee. The enantioselectivity is significantly affected by the imine N-substituent through non-bonding interactions with the chiral phosphoric acid and the 2-aminobenzamide. Copyright

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.

Enantioselective C-C bond formation to sulfonylimines through use of the 2-pyridinesulfonyl group as a novel stereocontroller

Enantioselective C-C bond formation to 2-pyridinesulfonylimines afforded products with good enantioselectivity. Dynamic induction of chirality on the sulfur by coordination of a chiral Lewis acid to the pyridine nitrogen and one of the prochiral sulfonyl oxygens induces enantioselectivity. Since the 2-pyridine-sulfonyl group can easily be removed after the reaction, it acts not only as an activating group but also as an efficient Stereocontroller.

Lewis base assisted Bronsted base catalysis: Bidentate phosphine oxides as activators and modulators of bronsted basic lanthanum-aryloxides

(Chemical Equation Presented) Dynamic Duo: A Lewis basic bidentate phosphine oxide was effective for activating and modulating the properties of Bronsted basic lanthanum aryl oxides. The Lewis base 1/lanthanum aryl oxide system was suitable for anti-selective Mannich-type reactions of trichloromethyl ketones (see scheme), affording unique building blocks for azetidine-2-carboxylic acids as well as β-amino acids.

Copper(I)-fesulphos Lewis acid catalysts for enantioselective Mannich-type reaction of N-sulfonyl imines

Copper(I) complexes of Fesulphos ligands are efficient chiral Lewis acid catalysts in the Mannich-type addition of silyl enol ethers of ketones, esters, and thioesters to N-(2-thienyl)sulfonyl aldimines. The corresponding optically active β-amino carbonyl