7188-38-7

Basic information

• Product Name: TERT-BUTYL ISOCYANIDE
• Synonyms: 2-ISOCYANO-2-METHYL-PROPANE;TERT-BUTYL ISOCYANIDE;TERT-BUTYL ISONITRILE;T-BUTYLISOCYANIDE;(CH3)3CNC;2-isocyano-2-methyl-propan;2-Methyl-2-isocyanopropane;Propane, 2-isocyano-2-methyl-
• CAS NO: 7188-38-7
• Molecular Formula: C₅H₉N
• Molecular Weight: 83.13
• EINECS: 230-553-5
• Product Categories: Isocyanides;Nitrogen Compounds;Organic Building Blocks;organic compound
• Mol File: 7188-38-7.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 91 °C(lit.)
• Flash Point: -2 °C
• Appearance: colorless/liquid
• Density: 0.735 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.376(lit.)
• Storage Temp.: Flammables area
• Solubility: Soluble in organic solvents such as ethanol, methanol, ether, to
• Stability: store cold
• BRN: 1903156
• CAS DataBase Reference: TERT-BUTYL ISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL ISOCYANIDE(7188-38-7)
• EPA Substance Registry System: TERT-BUTYL ISOCYANIDE(7188-38-7)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23-2017/11/23
• Safety Statements: 16-45
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• RTECS: EQ7102500
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 7188-38-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

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.

Preparation

Different sources of media describe the Preparation of 7188-38-7 differently. You can refer to the following data:
1. CAUTION: Use a well-ventilated hood and observe all precautions when using hydrogen cyanide.To a 1-1, stainless steel Hoke pressure cylinder in a well-ventilated hood is added 196 gm (3.5 moles) of isobutene, 95 gm (3.5 moles) of hydrogen cyanide, and 100 gm (0.7 mole) or cuprous bromide. The cylinder is closed, shaken for 15 hr at 70°C, cooled to room temperature, and vented cautiously in the hood, and the viscous residue is poured slowly into aqueous potassium cyanide (260 gm in 100 ml of water) to decompose the cuprous complex, liberating an organic layer. The organic layer is separated, dried, and distilled under reduced pressure to afford 97 gm, b.p. 60-63°C (314 mm Hg), ng 1.3749, IR 2143 s, 1472 m, 1368 m, 1230 m, 1208 m, 855 w c m - 1; yield, 33% based on starting isobutylene; 16% based on CuBr.
2. Phosgene (1.0 kg, 10.1 mol) was delivered through a wide tube into a stirred solution of N-t-butylformamide (1.01 kg, 10.0 mol) in triethylamine (1.30 kg) and o-dichlorobenzene (7.0 L) in a flask fitted with a reflux condenser charged with a freezing mixture of ice and salt (-20 C°). Water was added, the layers were separated, and the non-aqueous layer was dried over anhydrous potassium carbonate or magnesium sulfate and fractionated; bp 90–92 C°/750 mmHg; yield: 681 g (82%).

General Description

Carbon dative bond formation by tert-butyl isocyanide on the germanium (100) surface has been reported. It also forms complexes with metals and inserts into metal-carbon bonds to form iminoacyls.

InChI:InChI=1/C5H10N/c1-5(2,3)6-4/h4H,1-3H3/q+1

Upstream product

• 66875-78-3 2-bromo-N-(tert-butyl)-2-methylpropanamide 
• 67-56-1 methanol 
• 14387-85-0 1-tert-Butyl-3,3-dimethyl-2-aziridinon 
• 137503-69-6 tert-Butyl-trifluoromethylphosphanylidenemethylene-amine 
• 594-09-2 trimethylphosphane 
• 67-66-3 chloroform 
• 75-64-9 tert-butylamine 
• 1609-86-5 Tert-butyl isocyanate 
• 593-75-9 methyl isocyanate 
• 110039-30-0 MnBr₂(CNC(CH₃)3)(C₄H₈O)3 
• 998-40-3 tributylphosphine 
• 149-73-5 trimethyl orthoformate 
• 122-51-0 orthoformic acid triethyl ester 
• 471271-17-7 CH₃Re(NC₆H₃(CH(CH₃)2)2)2(CNC(CH₃)3)2 

Downstream Products

• 14610-37-8 N-methyl-tert-butylamine 
• 5813-64-9 2.2-dimethylpropylamine 
• 33867-28-6 3,3-Bis(chloromethyl)-4-tert.butoxy-butyronitril 
• 33867-27-5 3,3-Bis(jodomethyl)-4-tert.butoxy-butyronitril 
• 95275-47-1 2-[N'-Benzoyl-N-(3-chloro-propionyl)-hydrazino]-N-tert-butyl-2-methyl-propionamide 
• 96272-27-4 2-(N'-Benzoyl-N-phenylacetyl-hydrazino)-N-tert-butyl-3-phenyl-propionamide 
• 58861-77-1 4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 53229-12-2 L-4-Methoxycarbonyl-2-oxazolin 
• 64487-24-7 N-[1-(Butyl-tert-butyl-amino)-meth-(E)-ylidene]-benzamide 
• 64487-20-3 N-Butyl-N-[(E)-tert-butylimino-methyl]-benzamide 
• 64487-23-6 N-[1-(tert-Butyl-propyl-amino)-meth-(E)-ylidene]-benzamide 
• 64487-19-0 N-[(E)-tert-Butylimino-methyl]-N-propyl-benzamide 
• 64487-22-5 N-[1-(tert-Butyl-methyl-amino)-meth-(E)-ylidene]-benzamide 
• 64487-18-9 N-[(E)-tert-Butylimino-methyl]-N-methyl-benzamide 

Relevant articles and documents

Facile Synthesis of Cyanide and Isocyanides from CO

The reaction of K[N(SiMe3)2] with 13CO proceeds in C6D6 or THF affording K13CN and O(SiMe3)2 under mild conditions as confirmed by crystallographic characterization of K(18-crown-6)CN. Similarly reaction of the alkali metal amides, M[N(SiR3)R′] (M=Li, K; R=Ph, Me; R′=alkyl, aryl) provides the corresponding 13C labeled isocyanide RN13C and MOSiR3, generally in high yields. In some instances, the use of the sterically bulky Ph3Si-substituent is required to preclude 1,2-silyl migration affording the silylcarbamoyl salt M[Me3SiC(O)NR′]. These reactions have been used to obtain 19 examples of 13C labelled isocyanides, and several examples of gram scale reactions are reported. The mechanism of the reactions is probed via reliable DFT calculations.

Tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides: One-pot synthesis of heterocycles

This paper reports the tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides. According to this strategy, plenty of isocyanides have been synthesized, which is immediately used for the tandem reaction of Passerini/Wittig reaction in one pot. Compared to the previous work, this strategy avoids the separation, purification, and storage of isocyanides, which prominently solves the problems of isocyanide-based multicomponent reaction such as: (a) The environmentally unfriendly (strong foul odor), (a) the labile of Isocyanides, (c) high toxicity of isocyanides. In the meantime, in order to expand the application scope of our strategy, 1H-isochromenes and 3H-2-benzoxepin-1-ones have also been synthesized, which undergoes four-step transformations in one-pot. In addition, a relatively credible reaction mechanism has also been proposed, based on a series of control experiments. Furthermore, preliminary testing was performed on biological activity of some obtained compounds; These results showed that the synthesized compounds exhibited certain activity over P. digitatum and P. italicum. 2019 Elsevier Science. All rights reserved.

Magnesium Aldimines Prepared by Addition of Organomagnesium Halides to 2,4,6-Trichlorophenyl Isocyanide: Synthesis of 1,2-Dicarbonyl Derivatives

The selective addition of organomagnesium reagents to 2,4,6-trichlorophenyl isocyanide leading to magnesiated aldimines is reported. These aldimines react with Weinreb amides, ketones, or carbonates to provide the corresponding carbonyl derivatives after acidic cleavage. This allows for an efficient synthesis of 1,2-dicarbonyl compounds and α-hydroxy ketones.