119072-55-8

Basic information

• Product Name: tert-butylisonitrile
• CAS NO: 119072-55-8
• Molecular Weight: 83.1332
• Mol File: 119072-55-8.mol

Chemical Properties

• CAS DataBase Reference: tert-butylisonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butylisonitrile(119072-55-8)
• EPA Substance Registry System: tert-butylisonitrile(119072-55-8)

Safety Data

• Hazardous Substances Data: 119072-55-8(Hazardous Substances Data)

Upstream product

• 151-50-8 potassium cyanide 
• 506-64-9 silver(I) cyanide 
• 558-17-8 tert-Butyl iodide 
• 2425-74-3 t-butylformamide 
• 507-20-0 tertiary butyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 66875-78-3 2-bromo-N-(tert-butyl)-2-methylpropanamide 
• 4472-41-7 d₇-N,N-dimethylformamide 
• 104014-80-4 3-tert-Butyl-3,5-dihydro-5,5-dimethyl-4H-1,2,3-triazol-4-on 
• 6552-73-4 sodium methoxide-d3 
• 130014-19-6 (3R)-1,3-di-tert-butylaziridinone 
• 137503-69-6 tert-Butyl-trifluoromethylphosphanylidenemethylene-amine 
• 118231-06-4 N-tert-butyl-2,2-dimethyl-1-methoxycyclopropylamine 
• 105361-43-1 2-benzoyl-N-t-butyl-2-methylpropanimine 

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 
• 69805-65-8 N-tert-butyl-3-methyl-2-morpholin-4-yl-butyramide 
• 1205-08-9 methyl hippurate 
• 33083-83-9 undecan-5-one 
• 6636-80-2 1-cyclopentylpentan-1-one 
• 95022-55-2 α-(α'-Formyl-β'-benzoyl-hydrazino)-isovaleriansaeure-tert.-butylamid 
• 94931-66-5 α--diaethylessigsaeure-tert-butylamid 
• 57014-99-0 tert-butyl-(2-phenyl-4,4-bis-trifluoromethyl-4H-thiazol-5-ylidene)-amine 
• 57015-01-7 tert-butyl-(2-p-tolyl-4,4-bis-trifluoromethyl-4H-thiazol-5-ylidene)-amine 

Relevant articles and documents

Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3

An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate α-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.

Uebergangsmetall - Carbin-Komplexe XCIII. Thermodynamisches Gleichgewicht zwischen einem neutralen und einem kationischen Isonitril-substituirten Diethylaminocarbin-Komplex des Wolframs

The reaction of I(CO)2(t-C4H9NC)2WCNEt2 (I) with t-C4H9NC in n-heptane at 70 deg C leads to an approximately equimolar mixture of neutral, yellow carbyne complex mer-I(t-C4H9NC)3(CO)WCNEt2 (II) and cationic, orange carbyne complex CNEt2>+I- (III).In the presence of t-C4H9NC, there is a thermodynamic equilibrium between II and III, which permits the quantitative conversion of II to III in CH2Cl2 at room temperature, and of III to II in toluene at + 70 deg C.The composition and structure of the new complexes II and III were determined by elemental analyses, and from their IR, (1)H NMR, (13)C NMR, and by mass spectra.

TRIMETHYLSILYL CYANIDE PROMOTED CYANATION OF TERTIARY ALKYL CHLORIDES AND OTHER SN1 ACTIVE COMPOUNDS

Tertiary chlorides are readily cyanated in a one-pot procedure using trimethylsilyl cyanide in the presence of SnCl4.The mechanism of this novel and synthetically useful reaction involves initial isonitrile formation followed by rearrangement to the tertiary nitrile.Other SN1 active compounds also undergo smooth cyanation.

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.

Multiple Roles of Isocyanides in Palladium-Catalyzed Imidoylative Couplings: A Mechanistic Study

Kinetic, spectroscopic and computational studies examining a palladium-catalyzed imidoylative coupling highlight the dual role of isocyanides as both substrates and ligands for this class of transformations. The synthesis of secondary amides from aryl halides and water is presented as a case study. The kinetics of the oxidative addition of ArI with RNC-ligated Pd0species have been studied and the resulting imidoyl complex [(ArC=NR)Pd(CNR)2I] (Ar=4-F-C6H4, R=tBu) has been isolated and characterized by X-ray diffraction. The unprecedented ability of this RNC-ligated imidoyl-Pd complex to undergo reductive elimination at room temperature to give the amide in the presence of water and an F?/HF buffer is demonstrated. Its behavior in solution has also been characterized, revealing an unexpected strong tendency to give cationic complexes, and notably [(ArC=NR)Pd(CNR)3]+with excess isocyanide and [(ArC=NR)Pd(PP)(CNR)]+with bidentate phosphines (PP). These species may be responsible for catalyst deactivation and side-reactions. Ab initio calculations performed at the DFT level allowed us to rationalize the multiple roles of RNC in the different steps of the catalytic cycle.

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.

Process method for preparing tert-butyl isocyanide

The invention discloses a process method for preparing tert-butyl isocyanide, which comprises the following step of: carrying out a reaction with tert-butylamine as a raw material and an ortho-formatecompound under the action of alkali and a catalyst to obtain the tert-butyl isocyanide. The method has the advantages of cheap and easily available raw materials, environment-friendly process, high safety, high yield and high product purity.

Facile, catalyst-free cascade synthesis of sulfonyl guanidines: Via carbodiimide coupling with amines

An expeditious catalyst-free cascade coupling of N,N-dibromoarylsulfonamides with isonitriles and amines via carbodiimide intermediates has been developed. The protocol represents an elegant pathway for sulfonyl guanidines at room temperature within a short time with high yields and wide substrate scope. The carbodiimide intermediate could also be isolated in an appreciable yield.

Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides

This paper reports the tandem reaction strategy of the Passerini/Staudinger/aza-Wittig reaction based on the in situ capture of isocyanides. According to this strategy, isocyanides are synthesized in situ and immediately work as the substrate for the Passerini reaction and postmodification tandem reaction in one pot. In addition, two types of new compounds, 5-oxo-3,5-dihydrobenzo[e][1,4]oxazepines and 6-oxo-5,6-dihydro-2H-1,4-oxazines, were synthesized using the tandem reaction strategy that includes five-step transformations in one pot.

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.