14542-93-9

Basic information

• Product Name: 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE
• Synonyms: 2-isocyano-2,4,4-trimethyl-pentan;TERT-OCTYL ISOCYANIDE;TERT-OCTYLISONITRILE;WALBORSKY REAGENT;WALBORSKY'S REAGENT;1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE;1,1,3,3-TETRAMETHYLBUTYLISONITRILE;1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE, TEC H., 90+%
• CAS NO: 14542-93-9
• Molecular Formula: C₉H₁₇N
• Molecular Weight: 139.24
• EINECS: 238-577-8
• Mol File: 14542-93-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 55-57 °C11 mm Hg(lit.)
• Flash Point: 125 °F
• Appearance: /
• Density: 0.794 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.787mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• Storage Temp.: 2-8°C
• BRN: 2076559
• CAS DataBase Reference: 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE(14542-93-9)
• EPA Substance Registry System: 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE(14542-93-9)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22
• Safety Statements: 23-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 14542-93-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

1,1,3,3-Tetramethylbutyl isocyanide was used in the synthesis of substituted furans and imides.

Preparation

To a stirred solution of 83.0 g (0.528 mole) of N-(l,l,3,3-tetramethylbutyl) formamide in 11 of DMF was added dropwise, under a nitrogen atmosphere, a solution made up of thionyl chloride (40.3 ml, 0.55 mole) dissolved in 150 ml of DMF. The addition was at such a rate that the temperature did not exceed -50°C. After the addition, the cooling bath was removed momentarily to allow the temperature to increase to -35°C and then it was replaced while 118.0 g (1.11 mole) of sodium carbonate (anhydrous grade) was added. Then the cooling bath was removed and the reaction mixture was diluted with ice-cold water in a separatory funnel and then extracted with pentane. The pentane extract was dried over sodium sulfate and concentrated, and the product distilled to yield 68.4 g (93% yield), b.p. 55.5-56.6°C (11 mm). Infrared spectrum (neat) 2110 c m " 1 (s); nmr (neat) 51.08 [s, 9, C(CH3) 2] , 1.43 [t, 6, J = 2Hz, C(CH3) 2] , 1.58 (t, 2, J = 2.3 Hz, CH2).

InChI:InChI=1/C9H17NO/c1-8(2,3)6-9(4,5)10-7-11/h6H2,1-5H3

Upstream product

• 1449007-88-8 1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-1,3-dihydronaphtho[1,2-c]furan-1-carbonitrile 
• 1449007-84-4 N-[3-cyano-3-(phenylmethoxy)-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 
• 1449007-83-3 N-[3-butoxy-3-cyano-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 
• 1449007-82-2 N-[3-cyano-3-(1-methylethoxy)-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 
• 1449007-81-1 N-[3-cyano-3-propoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 
• 1449007-80-0 N-[3-cyano-3-methoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 
• 107-45-9 tert-Octylamine 
• 10151-02-7 N-(2,4,4-trimethylpentan-2-yl)formamide 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 74-90-8 hydrogen cyanide 

Downstream Products

• 268737-22-0 4-[3-(1,1,3,3-tetramethyl-butylamino)-imidazo[1,2-a]pyridin-2-yl]-benzoic acid methyl ester 
• 268737-23-1 4-[3-(1,1,3,3-tetramethyl-butylamino)-imidazo[1,2-a]pyrimidin-2-yl]-benzoic acid methyl ester 
• 268737-24-2 4-[3-(1,1,3,3-tetramethyl-butylamino)-imidazo[1,2-a]pyrazin-2-yl]-benzoic acid methyl ester 

Relevant articles and documents

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

Efficient isocyanide-less isocyanide-based multicomponent reactions

Isocyanides are the Jekyll and Hyde of organic chemistry allowing for extremely interesting transformations that are not only extremely odorous but also noxious. Therefore, an isocyanide-less isocyanide-based multicomponent reaction (IMCR) has been developed, and this protocol is expected to replace many of the old procedures in the future not only in IMCR but in other areas of organic chemistry as well.

Multicomponent cascade cycloaddition involving tropone, allenoate, and isocyanide: A rapid access to a 7,6,5-fused tricyclic skeleton

Multicomponent cascade cycloaddition of tropone, allenoate, and isocyanide has been disclosed. This method allows for the rapid construction of a highly unusual tricyclic skeleton in an efficient manner. The proposed transformation proceeds through [8 + 2 + 1] cycloaddition, [1,5]-H shift, and cyclization followed by an alkoxy group migration process.