N-Cyanobenzamide

Base Information

• Chemical Name: N-Cyanobenzamide
• CAS No.: 15150-25-1
• Molecular Formula: C8H6 N2 O
• Molecular Weight: 146.148
• Hs Code.: 2926909090
• European Community (EC) Number: 239-210-4
• NSC Number: 48654
• UNII: H5GU9QY9KM
• DSSTox Substance ID: DTXSID4065862
• Nikkaji Number: J218.358G
• Wikidata: Q81992468
• ChEMBL ID: CHEMBL57018
• Mol file: 15150-25-1.mol

Synonyms:N-Cyanobenzamide;15150-25-1;Benzamide, N-cyano-;benzoylcyanamide;benzoyl cyanamide;EINECS 239-210-4;NSC 48654;NSC-48654;N-cyano-benzamide;N-Benzoylcyanamide;H5GU9QY9KM;Oprea1_807948;CHEMBL57018;SCHEMBL262369;DTXSID4065862;NSC48654;MFCD00158929;STL231865;AKOS002295730;LS-05244;CS-0205161;FT-0701795;EN300-44160;E84173;J-008813;J-523535;Z276572712

Chemical Property of N-Cyanobenzamide

Chemical Property:

• Vapor Pressure: 0.000793mmHg at 25°C
• Melting Point: 141-142 °C
• Boiling Point: 293.3°Cat760mmHg
• PKA: 6.46±0.46(Predicted)
• Flash Point: 131.2°C
• PSA: 52.89000
• Density: 1.186g/cm³
• LogP: 1.28838
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.048012819
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

98%min ^*data from raw suppliers

BENZOYLCYANAMIDE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC#N

Technology Process of N-Cyanobenzamide

There total 24 articles about N-Cyanobenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

N-benzoylthiourea (614-23-3) → N-cyanobenzamide (15150-25-1)

Guidance literature:

With copper(l) iodide; sodium hydroxide; In dimethyl sulfoxide; at 90 ℃; for 2.5h;

DOI:10.1002/adsc.201000383

Reference yield: 90.0%

sodium cyanamide (19981-17-0,20611-81-8,123092-13-7,17292-62-5) + benzoic acid (65-85-0,8013-63-6) → N-cyanobenzamide (15150-25-1)

Guidance literature:

With trichloroisocyanuric acid; triphenylphosphine; In dichloromethane; water; at 25 - 30 ℃; for 0.166667h; Solvent; Sonication;

DOI:10.1055/s-0039-1691583

Reference yield: 88.0%

iodobenzene (591-50-4) + CYANAMID (420-04-2) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → N-cyanobenzamide (15150-25-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In 1,4-dioxane; at 65 ℃; for 20h; Sealed tube;

DOI:10.1016/j.tetlet.2013.10.040

upstream raw materials:

N-benzoyl-carbonimidic acid dichloride

N-benzoylthiourea

N-benzoyl O-ethyl isouree

tetrachloromethane

Downstream raw materials:

2-(N-benzoyldiaminomethylene)cyclohexane-1,3-dione

1-benzoylurea

N-(3-phenyl-[1,2,4]oxadiazol-5-yl)-benzamide

N-benzoyl-O-propyl-isourea

Refernces

• 1、 Mane, Rajendra S.,Nordeman, Patrik,Odell, Luke R.,Larhed, Mats. "Palladium-catalyzed carbonylative synthesis of N-cyanobenzamides from aryl iodides/bromides and cyanamide". . p. 6912 - 6915. Retrieved 2013.
• 2、 Phakhodee, Wong,Yamano, Dolnapa,Pattarawarapan, Mookda. "Ultrasound-Assisted Synthesis of N -Acylcyanamides and N -Acyl-Substituted Imidazolones from Carboxylic Acids by Using Trichloroisocyanuric Acid/Triphenylphosphine". supporting information. p. 703 - 707. Retrieved 2020/04/08.
• 3、 Sahoo, Santosh K.,Jamir, Latonglila,Guin, Srimanta,Patel, Bhisma K.. "Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides". experimental part. p. 2538 - 2548. Retrieved 2010/12/29.