175460-84-1

Basic information

• Product Name: N,N-dibenzyl-2-cyanoacetamide
• Synonyms: IVK/9056107;N,N-bis(benzyl)-2-cyano-acetamide;Oprea1_770322;N,N-dibenzyl-2-cyanoacetamide;2-cyano-N,N-bis(phenylmethyl)acetamide;2-cyano-N,N-bis(phenylmethyl)ethanamide
• CAS NO: 175460-84-1
• Molecular Formula: C₁₇H₁₆N₂O
• Molecular Weight: 264.32174
• Mol File: 175460-84-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N-dibenzyl-2-cyanoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dibenzyl-2-cyanoacetamide(175460-84-1)
• EPA Substance Registry System: N,N-dibenzyl-2-cyanoacetamide(175460-84-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 175460-84-1(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 372-09-8 cyanoacetic acid 
• 103-49-1 dibenzylamine 

Downstream Products

• 1627143-02-5 2-benzyl-3-oxo-2,3-dihydrocyclohepta[c]pyrrole-3a(1H)-carbonitrile 

Relevant articles and documents

Asymmetric Intramolecular Buchner Reaction: From High Stereoselectivity to Coexistence of Norcaradiene, Cycloheptatriene, and an Intermediate Form in the Solid State

Bicyclic compounds bearing a quaternary stereogenic center have been obtained using asymmetric intramolecular Buchner reaction with excellent yields and level of enantioselectivity. X-ray crystallography determination of the absolute configuration of one product has led to the serendipitous observation of an unusual behavior within the crystal structure, with equilibrating norcaradiene and cycloheptatriene valence isomers at the solid state, as well as an even more unexpected intermediate form. DFT calculations were performed to support these observations.

3-Alkylperoxy-3-cyano-oxindoles from 2-Cyano-2-diazo-N-phenyl-acetamides via Cyclizing Carbene Insertion and Subsequent Radical Oxidation

A transition-metal-free one-pot sequence for the synthesis of 3-peroxy-substituted oxindoles from readily prepared 2-cyano-2-diazo-acetamides is reported. The two-step tandem process includes a highly efficient thermal intramolecular C-H-carbene insertion

2-Amino-3-benzoylthiophene allosteric enhancers of A1, adenosine agonist binding: New 3, 4-, and 5-modifications

2-Amino-3-aroylthiophenes are agonist allosteric enhancers (AE) at the A1, adenosine receptor (A1AR). Here we report the syntheses of three kinds of novel 2-aminothiophenes and assays of their AE activity at the human A1AR (hA1AR), namely, (1) 2-amino-4,5-diphenylthiophene-3-carboxylates, 3a-h, (2) 2-amino-3-benzoyl-4,5-diphenylthiophenes, 7a-p, and (3) 2-amino-5-bromo-3-benzoyl-4-phenylthiophenes, 10a-h. An in vitro assay employing the A1AR agonist [125I]ABA and membranes from CHO-K1 cells stably expressing the hA1AR measured an index of AE activity, the ability of a candidate AE to stabilize the agonist-A1AR-G protein ternary complex, scored as the percentage of ternary complex remaining after 10 min of dissociation initiated by CPX and GTPγS. The AE activity score of 2-amino-4,5-dimethyl-3-(3-trifluoromethylbenzoyl)thiophene (PD 81,723), which was 19%, served as a standard for comparison. Two 3-carboxythiophene 3-trifluoromethylbenzyl esters, 3d (49%) and 3f (63%), had substantial AE activity. The 3-(1-naphthoyl) substituent of 7e (52%) also supported AE activity. Compounds in series 3 tended to be more potent, 10a and 10c having scores of 91 and 80%, respectively. The activity of 2-amino-5-bromo-3-ethoxycarbonyl-4-(3-nitrophenyl)thiophene, 10h (26%), is an exception to the rule that a 3-ethoxycarbonyl substituent cannot support AE activity.