2,6-Dimethylphenyl isocyanide

Base Information

• Chemical Name: 2,6-Dimethylphenyl isocyanide
• CAS No.: 2769-71-3
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.177
• Hs Code.: 2929900090
• European Community (EC) Number: 220-459-2
• NSC Number: 141690
• UNII: TD977ELU5R
• DSSTox Substance ID: DTXSID10182048
• Nikkaji Number: J1.923.624B,J100.427A
• Wikidata: Q83052704
• Mol file: 2769-71-3.mol

Synonyms:2,6-dimethylphenylisonitrile;2,6-DIMPI

Chemical Property of 2,6-Dimethylphenyl isocyanide

Chemical Property:

• Melting Point: 72-76 °C (lit.)
• Boiling Point: 205.6 °C at 760 mmHg
• Flash Point: 74.5 °C
• PSA: 0.00000
• Density: 0.98 g/cm³
• LogP: 2.08490
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 143

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dimethylphenyl isocyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)[N+]#[C-]
• Uses: 2,6-Dimethylphenyl isocyanate is used in the preparation of homoleptic metallaamidine complex, derivatized bets-cyclodextrins. It is used as chiral stationary phase in normal-phase liquid chromatography. It is also involved in the preparation of tris( 2,6-dimethylphenylimido)methylrhenium (VII) and 1-(2-isopropylphenyl)-3-(2,6-dimethylphenyl)urea. 2,6-Dimethylphenyl isocyanide may be employed for the synthesis of homoleptic metallaamidine complex, Mo(η2-Me2NCN-2,6-C6H3)4, via reaction with Mo(NMe2)4.

Technology Process of 2,6-Dimethylphenyl isocyanide

There total 26 articles about 2,6-Dimethylphenyl 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%

cobalt(Cl)2(2,6-xylyl isocyanide)4 (67662-53-7) + Benzyl isocyanide (88333-03-3,10340-91-7) → CoCl2(CNC6H3(CH3)2)3(CNCH2C6H5) + 2,6-dimethylphenyl isonitrile (119072-54-7,2769-71-3)

Guidance literature:

In benzene; at 80 °C, under Ar;

Reference yield: 85.0%

{Ir2(CN-2,6-Me2C6H3)5(bis(dimethylphosphino)methane)2}{PF6}2 → Ir2(2,6-Me2C6H3CN)4(dmpm)2 + 2,6-dimethylphenyl isonitrile (119072-54-7,2769-71-3)

Guidance literature:

With sodium amalgam; In benzene; under N2, excess sodium amalgam, stirred for 3 days; decanted, filtered, evapn. under vac., washed with benzene (removal of isocyanide), recrystn. (benzene/hexane); elem. anal.;

DOI:10.1021/ja00202a023

Reference yield: 65.0%

N-acetyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine (112547-81-6) → 2,6-dimethylphenyl isonitrile (119072-54-7,2769-71-3) + C22H26N6O2 (107322-05-4,112574-83-1)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 48h; Ambient temperature;

upstream raw materials:

2,6-dimethylformanilide

N-acetyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine

N-(2,6-dimethylphenylaminomethylene)-N'-methoxycarbonylhydrazine

N-benzoyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine

Downstream raw materials:

3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-thiazolidine-2-thione

2-<2,6-Dimethyl-phenylimino>-3,4-dimethyl-penten-(3)-saeure-<2,6-dimethyl-anilid>

(2,6-dimethyl-phenyl)-dithiocarbonimidic acid 5-chloro-benzothiazol-2-yl ester cyclohexyl ester

N-(2,6-dimethyl-phenyl)-formimidic morpholine-4-carbothioic thioanhydride

Refernces

• 1、 Weidlich, Frauke,Esumi, Naoto,Chen, Dongyang,Mück-Lichtenfeld, Christian,Zysman-Colman, Eli,Studer, Armido. "Mild C?F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm". . p. 376 - 383. Retrieved 2019/11/19.
• 2、 Beer, Henrik,Bresien, Jonas,Michalik, Dirk,Schulz, Axel,Villinger, Alexander. "Reversible switching between housane and cyclopentanediyl isomers: An isonitrile-catalysed thermal reverse reaction". supporting information. p. 13986 - 13992. Retrieved 2020/11/02.