tert-BUTYL ISOCYANIDE

Base Information

• Chemical Name: tert-BUTYL ISOCYANIDE
• CAS No.: 7188-38-7
• Molecular Formula: C₅H₉N
• Molecular Weight: 83.1332
• Hs Code.: 2929109000
• European Community (EC) Number: 230-553-5
• NSC Number: 141687
• UNII: 22S4Z857K3
• DSSTox Substance ID: DTXSID60222145
• Nikkaji Number: J2.267.272J,J42.749G
• Wikipedia: Tert-Butyl_isocyanide
• Wikidata: Q3266872
• Mol file: 7188-38-7.mol

Synonyms:1,1-dimethylethyl isocyanide;t-butyl isocyanide;tert-Bu-NC;tert-butyl isocyanide

Chemical Property of tert-BUTYL ISOCYANIDE

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Melting Point: 148-150 °C
• Refractive Index: n20/D 1.376(lit.)
• Boiling Point: 91 °C(lit.)
• Flash Point: -2 °C
• PSA: 0.00000
• Density: 0.735 g/mL at 25 °C(lit.)
• LogP: 0.93490
• Storage Temp.: Flammables area
• Solubility.: Soluble in organic solvents such as ethanol, methanol, ether, to
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 83.073499291
• Heavy Atom Count: 6
• Complexity: 77.8

Purity/Quality:

98%, ^*data from raw suppliers

tert-Butyl isocyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FT
• Hazard Codes: F,T
• Statements: 11-23-2017/11/23
• Safety Statements: 16-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)[N+]#[C-]
• Uses: tert-Butyl isocyanide is used in a tin-free procedure for alkyl radical reactions in the presence of a free-radical initiator. It is a useful intermediate in multicomponent reactions. It is also used in the synthesis of coumarines, 4H-chromenes, isoxazolines and to trap 2-cyclopropylidene-1,3-diones.

Technology Process of tert-BUTYL ISOCYANIDE

There total 58 articles about tert-BUTYL 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%

carbon monoxide (201230-82-2) + lithium tert-butyl-trimethylsilylamide (18270-42-3) → tert-butylisonitrile (119072-55-8,7188-38-7)

Guidance literature:

In benzene-d6; at 20 ℃; for 12h; under 3040.2 Torr; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.202105909

Reference yield: 97.0%

tert-butylamine (75-64-9) + orthoformic acid triethyl ester (122-51-0) → tert-butylisonitrile (119072-55-8,7188-38-7)

Guidance literature:

With dmap; tetrabutylammomium bromide; In 5,5-dimethyl-1,3-cyclohexadiene; at 20 - 60 ℃; for 12h; Industrial scale;

Reference yield: 96.0%

t-butylformamide (2425-74-3) → tert-butylisonitrile (119072-55-8,7188-38-7)

Guidance literature:

With quinoline; p-toluenesulfonyl chloride; at 75 ℃; for 1h; under 1 Torr; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.5b05033

upstream raw materials:

potassium cyanide

silver(I) cyanide

tert-Butyl iodide

t-butylformamide

Downstream raw materials:

N-methyl-tert-butylamine

2.2-dimethylpropylamine

2-[N'-Benzoyl-N-(3-chloro-propionyl)-hydrazino]-N-tert-butyl-2-methyl-propionamide

2-(N'-Benzoyl-N-phenylacetyl-hydrazino)-N-tert-butyl-3-phenyl-propionamide

Refernces

• 1、 -. "Process method for preparing tert-butyl isocyanide". Paragraph 0038-0047; 0058-0066. . Retrieved 2020/06/09.
• 2、 Liu, Na,Chao, Fei,Liu, Ming-Guo,Huang, Nian-Yu,Zou, Kun,Wang, Long. "Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides". . p. 2366 - 2371. Retrieved 2019/05/16.