14542-93-9 Usage
Description
1,1,3,3-Tetramethylbutyl isocyanide, also known as TMI, is a clear colorless liquid with unique chemical properties. It is an organic compound that is widely utilized in the synthesis of various chemical compounds due to its reactive nature and versatility.
Uses
Used in Chemical Synthesis:
1,1,3,3-Tetramethylbutyl isocyanide is used as a synthetic building block for the creation of substituted furans and imides. Its reactivity and compatibility with various chemical reactions make it a valuable component in the synthesis process, contributing to the development of new and innovative compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,1,3,3-Tetramethylbutyl isocyanide is used as a key intermediate in the synthesis of various drug molecules. Its unique chemical properties allow for the development of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Material Science:
1,1,3,3-Tetramethylbutyl isocyanide is also utilized in the field of material science, where it is employed in the synthesis of advanced polymers and materials with specific properties. These materials can be used in a wide range of applications, from coatings and adhesives to high-performance plastics and elastomers.
Used in Agrochemical Industry:
In the agrochemical industry, 1,1,3,3-Tetramethylbutyl isocyanide is used as a starting material for the synthesis of various agrochemicals, including pesticides and herbicides. Its role in the development of these products helps to improve agricultural productivity and protect crops from pests and diseases.
Overall, 1,1,3,3-Tetramethylbutyl isocyanide is a versatile and valuable compound with a wide range of applications across various industries, including chemical synthesis, pharmaceuticals, material science, and agrochemicals. Its unique properties and reactivity make it an essential component in the development of new and innovative products with potential benefits for society and the environment.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 14542-93-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,5,4 and 2 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 14542-93:
(7*1)+(6*4)+(5*5)+(4*4)+(3*2)+(2*9)+(1*3)=99
99 % 10 = 9
So 14542-93-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H17NO/c1-8(2,3)6-9(4,5)10-7-11/h6H2,1-5H3
14542-93-9Relevant articles and documents
Isocyanide 2.0
Ahmadian-Moghaddam, Maryam,D?mling, Alexander,Patil, Pravin
supporting information, p. 6902 - 6911 (2020/11/09)
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
Neochoritis, Constantinos G.,Stotani, Silvia,Mishra, Bhupendra,D?mling, Alexander
supporting information, p. 2002 - 2005 (2015/04/27)
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
Jia, Shuanglong,Su, Shikuan,Li, Chunju,Jia, Xueshun,Li, Jian
, p. 5604 - 5607 (2015/02/19)
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.