Benzyl isocyanide

Base Information

• Chemical Name: Benzyl isocyanide
• CAS No.: 10340-91-7
• Molecular Formula: C8H7 N
• Molecular Weight: 603.734
• Hs Code.: 29269090
• European Community (EC) Number: 233-738-9
• UNII: UEU57DSL26
• DSSTox Substance ID: DTXSID50145819
• Nikkaji Number: J10.461B
• Wikidata: Q83010476
• Mol file: 10340-91-7.mol

Synonyms:Benzyl isocyanide;10340-91-7;BenzylIsocyanide;(isocyanomethyl)benzene;Isocyanomethylbenzene;Benzene, isocyanomethyl-;Benzyl isonitrile;(benzylimino)methylidene;EINECS 233-738-9;1-(isocyanomethyl)benzene;UEU57DSL26;MFCD00000004;benzylisonitrile;Tolyl isocyanide;benzylisonit-rile;isocyanomethylbenzol;isocyanomethyl-benzene;UNII-UEU57DSL26;SCHEMBL168131;DTXSID50145819;CS-M2850;BBL020653;GEO-02805;STK893343;AKOS001476193;CS-13439;NS-01021;B2185;FT-0636686;A18033;EN300-257838;A934910;J-000960

Chemical Property of Benzyl isocyanide

Chemical Property:

• Refractive Index: n20/D 1.521(lit.)
• Boiling Point: °Cat760mmHg
• PKA: 27.4
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: 1.33660
• Storage Temp.: ?20°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.057849228
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzyl isocyanide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [C-]#[N+]CC1=CC=CC=C1
• Uses: Benzyl Isocyanide is used in the preparation of arylamide compounds. also used as a catalyst in the cycloaddition of norbornenes with internal and terminal acetylenes.

Technology Process of Benzyl isocyanide

There total 25 articles about Benzyl isocyanide 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: 100.0%

Benzeneacetamide (103-81-1) → Benzyl isocyanide (88333-03-3,10340-91-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at -10 ℃;

DOI:10.1002/ejoc.201901776

Reference yield: 96.0%

dichlorure de l'acide N-(phenylmethyl) carbonimidique (6181-92-6) → Benzyl isocyanide (88333-03-3,10340-91-7)

Guidance literature:

With lithium perchlorate; sodium carbonate; In N,N-dimethyl-formamide; at 15 ℃; cathodic reduction at -1.75 V (vs. SCE);

DOI:10.1016/S0040-4039(00)61284-4

Reference yield: 84.0%

5-benzylamino-tetrazole (14832-58-7) → Benzyl isocyanide (88333-03-3,10340-91-7)

Guidance literature:

With sodium hypobromide; sodium hydroxide; In dichloromethane; water; at 0 ℃; for 0.25h;

DOI:10.15227/orgsyn.061.0014

upstream raw materials:

silver(I) cyanide

iodomethylbenzene

chloroform

benzylamine

Downstream raw materials:

1-Benzylimino-3,3,5,5-tetraphenyl-cyclopentadion-(2,4)

4-phenyl-1-oxa-3-aza-spiro[4.4]non-2-ene

5c-methyl-4r,5t-diphenyl-4,5-dihydro-oxazole

5t-methyl-4r,5c-diphenyl-4,5-dihydro-oxazole

Refernces

• 1、 Waibel,Nickisch,M?hl,Seim,Meier. "A more sustainable and highly practicable synthesis of aliphatic isocyanides". . p. 933 - 941. Retrieved 2020.
• 2、 Zeng, Debin,Ma, Yuying,Zhang, Rui,Nie, Quandeng,Cui, Zhengjie,Wang, Yaxin,Shang, Luqing,Yin, Zheng. "Synthesis and structure–activity relationship of α-keto amides as enterovirus 71 3C protease inhibitors". . p. 1762 - 1766. Retrieved 2016.
• 3、 Si, Yi-Xin,Zhu, Peng-Fei,Zhang, Song-Lin. "Synthesis of isocyanides by reacting primary amines with difluorocarbene". . p. 9086 - 9090. Retrieved 2020.
• 4、 Guirado, Antonio,Zapata, Andres,Fenor, Manuel. "ELECTROCHEMICAL REDUCTION OF CARBONIMIDOYL DICHLORIDES. A NEW METHOD FOR THE PREPARATION OF ISOCYANIDES". . p. 4779 - 4782. Retrieved 1992.
• 5、 Mohy El Dine, Tharwat,Evans, David,Rouden, Jacques,Blanchet, Jér?me. "Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions". . p. 5894 - 5898. Retrieved 2016.
• 6、 Leech, Matthew C.,Petti, Alessia,Tanbouza, Nour,Mastrodonato, Andrea,Goodall, Iain C. A.,Ollevier, Thierry,Dobbs, Adrian P.,Lam, Kevin. "Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides". . p. 9371 - 9375. Retrieved 2021/12/09.
• 7、 Barther, Dennis,Malliaridou, Triantafillia,Meier, Michael A. R.,Moatsou, Dafni,Waibel, Kevin A.. "One-Pot Synthesis of Thiocarbamates". supporting information. p. 4508 - 4516. Retrieved 2021/08/30.