20600-56-0

Basic information

• Product Name: Benzene, 1-isocyano-3,5-dimethyl- (9CI)
• Synonyms: Benzene, 1-isocyano-3,5-dimethyl- (9CI);3-Isocyano-1,5-dimethylbenzene
• CAS NO: 20600-56-0
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17446
• Product Categories: ISONITRITE
• Mol File: 20600-56-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzene, 1-isocyano-3,5-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-isocyano-3,5-dimethyl- (9CI)(20600-56-0)
• EPA Substance Registry System: Benzene, 1-isocyano-3,5-dimethyl- (9CI)(20600-56-0)

Safety Data

• Hazardous Substances Data: 20600-56-0(Hazardous Substances Data)

Upstream product

• 16618-52-3 N-(3,5-dimethylphenyl)formamide 
• 108-69-0 3,5-dimethylaminoaniline 

Downstream Products

• 1325218-07-2 N-(3,5-dimethylphenyl)-4-amino-6-methyl-2-phenylquinazoline 
• 1423780-87-3 1-(2,6-dimethylphenylimino)-1,2,4,5-tetrahydrobenzo[c]azepin-3-one 
• 1423780-88-4 2-(2-cyanoethyl)-N-(2,6-dimethylphenyl)benzamide 

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

Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines

A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.

Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

TEMPO-Catalyzed Aerobic Oxidative Selenium Insertion Reaction: Synthesis of 3-Selenylindole Derivatives by Multicomponent Reaction of Isocyanides, Selenium Powder, Amines, and Indoles under Transition-Metal-Free Conditions

A novel and efficient approach for the selenium functionalization of indoles was developed with selenium powder as the selenium source, catalyzed by 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and employing O2 as the green oxidant. This protocol provides a practical route for the synthesis of 3-selenylindole derivatives and has the advantages of readily available starting materials, mild reaction conditions, and a wide scope of substrates. Electron spin-resonance (ESR) studies reveal that the approach involves the formation of nitrogen-centered radicals and selenium radicals via oxidation of in situ generated selenoates.

Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD Ring Cores of Camptothecins

A new strategy for constructing indolizino[1,2-b]quinolin-9(11H)-ones (ring cores of camptothecins) from readily available isocyanoarenes and N-(alkyl-2-yn-1-yl)pyridin-2(1H)-ones has been developed through a visible-light-induced radical cascade cyclization process. The reaction proceeds under mild conditions with fair to excellent yields. The easy introduction of substituents for both reactants and the broad functional group tolerance of the reaction make it a straightforward route to the cores of the marketed camptothecins and their derivatives.

Cobalt(II)-Catalyzed Isocyanide Insertion Reaction with Sulfonyl Azides in Alcohols: Synthesis of Sulfonyl Isoureas

A Co(II)-catalyzed isocyanide insertion reaction with sulfonyl azides in alcohols to form sulfonyl isoureas via nitrene intermediate has been developed. This protocol provides a new, environmentally friendly, and simple strategy for the synthesis of sulfonyl isourea derivatives by employing a range of substrates under mild conditions.

Palladium-catalyzed intramolecular C(sp2)-H amidination by isonitrile insertion provides direct access to 4-aminoquinazolines from N-arylamidines

An efficient method for the synthesis of 4-amino-2-aryl(alkyl)quinazolines from readily available N-arylamidines and isonitriles via palladium-catalyzed intramolecular aryl C-H amidination by isonitrile insertion has been developed.

Lewis acid-promoted imine synthesis by the insertion of isocyanides into C-H bonds of electron-rich aromatic compounds

The Lewis acid-promoted insertion of isocyanides into aromatic C-H bonds is reported. An imine functionality containing an array of N-substituents can be introduced directly into electron-rich aromatics in good yields.

Thermal oligomerisation of aryl isocyanides: Formation of pyrazino[1,2-a:4,5-a′]diindoles and indigo diarylimines

The aryl isocyanides 1-4 are converted at 150°C into the hexameric pyrazino[1,2-a:4,5-a′]diindoles 15-19. 4-Fluorophenyl isocyanide, when heated at 135°C, gave the hexamer 19 and the tetrameric indigo di-arylimine 9, and when kept at ambient temperature g