15150-25-1

Basic information

• Product Name: N-cyanobenzamide
• Synonyms: N-cyanobenzamide;Benzamide, N-cyano- (8CI,9CI);Benzamide, N-cyano-;Einecs 239-210-4;Nsc 48654;N-BenzoylcyanaMide;BENZOYLCYANAMIDE
• CAS NO: 15150-25-1
• Molecular Formula: C₈H₆N₂O
• Molecular Weight: 146.14604
• EINECS: 239-210-4
• Product Categories: AMIDE
• Mol File: 15150-25-1.mol

Chemical Properties

• Melting Point: 141-142 °C
• Boiling Point: 293.3°Cat760mmHg
• Flash Point: 131.2°C
• Appearance: /
• Density: 1.186g/cm³
• Vapor Pressure: 0.000793mmHg at 25°C
• Refractive Index: 1.559
• PKA: 6.46±0.46(Predicted)
• CAS DataBase Reference: N-cyanobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-cyanobenzamide(15150-25-1)
• EPA Substance Registry System: N-cyanobenzamide(15150-25-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 15150-25-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5440, 1955 DOI: 10.1021/ja01625a085

InChI:InChI=1/C8H6N2O/c9-6-10-8(11)7-4-2-1-3-5-7/h1-5H,(H,10,11)

Upstream product

• 3911-55-5 N-benzoyl-carbonimidic acid dichloride 
• 614-23-3 N-benzoylthiourea 
• 62432-77-3 N-benzoyl O-ethyl isouree 
• 56-23-5 tetrachloromethane 
• 420-04-2 CYANAMID 
• 98-88-4 benzoyl chloride 
• 19981-17-0 sodium cyanamide 
• 156-62-7 calcium cyanamide 
• 532-55-8 Benzoyl isothiocyanate 
• 64-17-5 ethanol 
• 100-64-1 cyclohexanone-oxime 
• 71-43-2 benzene 
• 65-85-0 benzoic acid 
• 108-86-1 bromobenzene 

Downstream Products

• 420-04-2 CYANAMID 
• 93-89-0 benzoic acid ethyl ester 
• 26899-30-9 N-(3-phenyl-[1,2,4]oxadiazol-5-yl)-benzamide 
• 92033-07-3 O-(i-Amyl)-N-benzoyl-isoharnstoff 
• 61679-73-0 C₁₄H₁₁N₃O₃ 
• 78555-57-4 benzoylamino-2 methyl-6 4H-oxazine-1,3 one-4 
• 128118-68-3 2-benzoylamino-6-chloro-4-oxo-5-phenyl-4H-1,3-oxazine 
• 400751-91-9 2-nitro-1-amino-1-benzoylamino-2-ethoxycarbonylethylene 
• 97267-71-5 N-[6-(4-Chloro-phenyl)-4-oxo-4H-[1,3]oxazin-2-yl]-benzamide 
• 80176-35-8 N'-Benzoyl-N-cyclohexyl-N-[2-hydroxy-3-(naphthalen-1-yloxy)-propyl]-guanidine 
• 80176-28-9 (m-methyl phenoxy-1 hydroxy-2 propyl)-1 cyclohexyl-1 benzoyl-3 guanidine 
• 80176-23-4 N'-Benzoyl-N-cyclohexyl-N-(2-hydroxy-3-o-tolyloxy-propyl)-guanidine 
• 80176-31-4 N'-Benzoyl-N-[3-(2-chloro-phenoxy)-2-hydroxy-propyl]-N-cyclohexyl-guanidine 
• 80176-33-6 N'-Benzoyl-N-[3-(4-chloro-phenoxy)-2-hydroxy-propyl]-N-cyclohexyl-guanidine 

Relevant articles and documents

Palladium-catalyzed carbonylative synthesis of N-cyanobenzamides from aryl iodides/bromides and cyanamide

A novel and convenient protocol for the synthesis of N-cyanobenzamides starting from readily available aryl halides and cyanamide via palladium-catalyzed aminocarbonylation has been developed. The protocol utilizes Mo(CO)6 as the CO source or CO(gas) and affords the desired N-cyanobenzamides in moderate to good yields.

Ultrasound-Assisted Synthesis of N -Acylcyanamides and N -Acyl-Substituted Imidazolones from Carboxylic Acids by Using Trichloroisocyanuric Acid/Triphenylphosphine

A convenient ultrasound-assisted one-pot synthesis of N -acylcyanamides starting from readily available carboxylic acids and sodium cyanamide has been developed. Upon activation in the presence of trichloroisocyanuric acid (TCCA) and triphenylphosphine, a range of carboxylic acids was converted into N -acylcyanamides in good to excellent yields within 10 minutes at room temperature without base. Remarkably, N -acyl-substituted imidazolones were readily accessible through guanylation-cyclization of the in situ generated N -acylcyanamides.

COMPOSITIONS AND METHODS COMPRISING SUBSTITUTED 2-AMINOIMIDAZOLES

The present invention presents 2-(acylamino)imidazoles with therapeutic activity, including selective activity against cancer cells, and compositions comprising them. Methods of using and preparing the 2-(acylamino)imidazoles are also presented.

Novel two-step, one-pot synthesis of primary acylureas

A new procedure for the synthesis of primary acylureas from cyanamide and a variety of carboxylic acids is described. Under mild reaction conditions, the products were obtained in good yield from commercially available starting materials.

Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides

We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).

Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl)amide

Sodium bis(trimethylsilyl)amide was first used as the desulfurizing agent for the conversion of isothiocyanates to cyanamides in a 'one-flask' reaction. Crown Copyright

Synthesis of bis(arylcarbonylamino-1H-benzimidazol-5-yl) ethers

A procedure has been developed for the synthesis of bis(arylcarbonylamino- 1H-benzimidazol-5-yl) ethers by reaction of the corresponding substituted benzoyl chloride with sodium cyanamide, followed by treatment of the resulting N-cyanobenzamide with 4-(3,4-diaminophenoxy)benzene-1,2-diamine in acid medium. Nauka/Interperiodica 2006.

Sodium bis(trimethylsilyl)amide in the 'one-flask' transformation of isocyanates to cyanamides

Cyanamides were successfully prepared in a 'one-flask' reaction from isocyanates by use of sodium bis(trimethylsilyl)amide as the deoxygenating agents in THF at room temperature. Georg Thieme Verlag Stuttgart.

Bis-arylsulfonamide derivatives of 2-amino-5(6)-(4-aminophenylthio)benzimidazole

Three different procedures have been developed for the preparation of bis-arylsulfonamide derivatives of 2-amino-5(6)-(4-aminophenylthio)benzimidazole, and biological activity of the products have been studied.

Acylated cyanamide composition for treating ethanol ingestion

Acylated cyanamide compounds useful for ethanol deterrence of the formula RCONHCN, wherein R is a lipophilic acyl group or is derived from an (N-substituted)-alpha-aminoacyl group.