2769-71-3

Basic information

• Product Name: 2,6-DIMETHYLPHENYL ISOCYANIDE
• Synonyms: HANSA ISN-0083;2,6-DIMETHYLPHENYL ISOCYANIDE;RARECHEM AQ BD 0027;VIC-M-XYLYL ISOCYANIDE;2,6-xylyl isocyanide;Benzene, 2-isocyano-1,3-dimethyl- (9CI);m-xylyl isocyanide;2,6-dimethylphenylisonitrile
• CAS NO: 2769-71-3
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 220-459-2
• Product Categories: ISONITRITE
• Mol File: 2769-71-3.mol
• Article Data: 43

Chemical Properties

• Melting Point: 72-76 °C(lit.)
• Boiling Point: 50-53℃ (0.01 Torr)
• Flash Point: 74.5 °C
• Appearance: /Crystalline
• Density: 0.98 g/cm³
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• BRN: 3541909
• CAS DataBase Reference: 2,6-DIMETHYLPHENYL ISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYLPHENYL ISOCYANIDE(2769-71-3)
• EPA Substance Registry System: 2,6-DIMETHYLPHENYL ISOCYANIDE(2769-71-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2769-71-3(Hazardous Substances Data)

Usage

Description

2,6-DIMETHYLPHENYL ISOCYANIDE is an organic compound characterized by its isocyanide functional group and a 2,6-dimethylphenyl moiety. It is a versatile building block in organic synthesis and has found applications in various fields due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
2,6-DIMETHYLPHENYL ISOCYANIDE is used as a key intermediate in the synthesis of homoleptic metallaamidine complexes, such as Mo(η2-Me2NCN-2,6-C6H3)4, which are important in coordination chemistry and have potential applications in catalysis and materials science.
Used in Analytical Chemistry:
In the field of analytical chemistry, 2,6-DIMETHYLPHENYL ISOCYANIDE is utilized as a chiral stationary phase in normal-phase liquid chromatography. This application takes advantage of its chiral properties to separate enantiomers, which is crucial in pharmaceutical development and quality control.
Used in Derivatization of Cyclodextrins:
2,6-DIMETHYLPHENYL ISOCYANIDE is employed in the preparation of derivatized β-cyclodextrins, which are widely used in various industries, including pharmaceuticals, food, and cosmetics, for their ability to form inclusion complexes with a range of guest molecules.
Used in Coordination Chemistry:
The compound is involved in the preparation of tris(2,6-dimethylphenylimido)methylrhenium(VII) complexes, which have potential applications in homogeneous catalysis and as precursors for the synthesis of other organometallic complexes.
Used in Agrochemicals:
2,6-DIMETHYLPHENYL ISOCYANIDE may be used in the synthesis of 1-(2-isopropylphenyl)-3-(2,6-dimethylphenyl)urea, which is a key intermediate in the production of agrochemicals, specifically herbicides. This application highlights the compound's role in the development of products that contribute to agricultural productivity and crop protection.

InChI:InChI=1/C9H10N/c1-7-5-4-6-8(2)9(7)10-3/h3-6H,1-2H3/q+1

Upstream product

• 607-92-1 2,6-dimethylformanilide 
• 112547-81-6 N-acetyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine 
• 112547-80-5 N-(2,6-dimethylphenylaminomethylene)-N'-methoxycarbonylhydrazine 
• 112547-82-7 N-benzoyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine 
• 112547-83-8 ethyl 2-acetylhydrazono-2-(2,6-dimethylphenylamino)acetate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67-66-3 chloroform 
• 87-62-7 2,6-dimethylaniline 
• 542-69-8 1-iodo-butane 
• 594-19-4 tert.-butyl lithium 
• 154592-61-7 2,6-xylyl isoselenocyanate 
• 53178-41-9 2-lithio-2-phenyl-1,3-dithiane 
• 4440-01-1 lithium phenylacetylide 
• 111351-61-2 2,2,4,4-tetramethyl-3-(2,6-xylylimino)-2,4-disilapentane 

Downstream Products

• 66859-00-5 3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-thiazolidine-2-thione 
• 22747-89-3 2-<2,6-Dimethyl-phenylimino>-3,4-dimethyl-penten-(3)-saeure-<2,6-dimethyl-anilid> 
• 66858-90-0 (2,6-dimethyl-phenyl)-dithiocarbonimidic acid 5-chloro-benzothiazol-2-yl ester cyclohexyl ester 
• 53043-09-7 N-(2,6-dimethyl-phenyl)-formimidic morpholine-4-carbothioic thioanhydride 
• 66858-97-7 3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-3H-benzooxazole-2-thione 
• 66858-93-3 3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-3H-benzothiazole-2-thione 
• 115652-20-5 <2-methyl-1(2,6-xylylimino)propyl>trimethylsilane 
• 115652-18-1 N-2.6-Dimethylphenyl(trimethylsilyl)ethylimin 
• 66858-87-5 N-(2,6-dimethyl-phenyl)-2,6-dimethyl-morpholine-4-carboximidothioic acid cyclohexyl ester 
• 66858-88-6 N-(2,6-dimethyl-phenyl)-2-thioxo-benzothiazole-3-carboximidothioic acid cyclohexyl ester 
• 66858-89-7 (2,6-dimethyl-phenyl)-dithiocarbonimidic acid benzothiazol-2-yl ester cyclohexyl ester 
• 66858-94-4 5-chloro-3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-3H-benzothiazole-2-thione 
• 66858-96-6 3-[N-(2,6-dimethyl-phenyl)-formimidoyl]-6-ethoxy-3H-benzothiazole-2-thione 
• 35601-96-8 ethyl 2,6-dimethylphenylcarbamate 

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

Mild C?F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm

Fluorinated compounds have become important in the fields of agrochemical industry, pharmaceutical chemistry and materials sciences. Accordingly, various methods for their preparation have been developed in the past. Fluorinated compounds can be accessed via conjugation with fluorinated building blocks, via C?H fluorination or via selective activation of perfluorinated compounds to give the partially fluorinated congeners. Especially the direct activation of C?F bonds, one of the strongest σ-bonds, still remains challenging and new strategies for C?F activation are desirable. Herein a method for the photochemical activation of aromatic C?F bonds is presented. It is shown that isonitriles selectively insert into aromatic C?F bonds while aliphatic C?F bonds remain unaffected. Mechanistic studies reveal the reaction to proceed via the indirect excitation of the isonitrile to its triplet state by photoexcited acetophenone at 350 nm. Due to the relatively mild light used, the process shows high functional group tolerance and various compounds of the class of benzimidoyl fluorides are accessible from aryl isonitriles and commercially available perfluorinated arenes. (Figure presented.).

Crystal structures and spectroscopic characterization of MBr2(CNXyl)n (M = Fe and Co, n = 4; M = Ni, n = 2; Xyl = 2,6-dimethylphenyl), and of formally zero-valent iron as a cocrystal of Fe(CNXyl)5 and Fe2(CNXyl)9

Structures and spectroscopic characterization of the divalent complexes cisdibromidotetrakis( 2,6-dimethylphenyl isocyanide)iron(II) dichloromethane 0.771-solvate, [FeBr2(C9H9N)4]-0.771CH2Cl2 or cis-FeBr2(CNXyl)4-0.771CH2Cl2 (Xyl = 2,6-dimethylphenyl), trans-dibromidotetrakis(2,6-dimethylphenyl isocyanide)-iron(II), [FeBr2(C9H9N)4] or trans-FeBr2(CNXyl)4, trans-dibromidotetrakis(2,6-dimethylphenyl isocyanide)cobalt(II), [CoBr2(C9H9N)4] or trans-CoBr2(CNXyl)4, and trans-dibromidobis(2,6-dimethylphenyl isocyanide)nickel(II), [NiBr2(C9H9N)2] or trans-NiBr2(CNXyl)2, are presented. Additionally, crystals grown from a cold diethyl ether solution of zero-valent Fe(CNXyl)5 produced a structure containing a cocrystallization of mononuclear Fe(CNXyl)5 and the previously unknown dinuclear [Fe(CNXyl)3]2(-2-CNXyl)3, namely pentakis(2,6-dimethylphenyl isocyanide)iron(0) tris(-2-2,6-dimethylphenyl isocyanide)bis[tris(2,6-dimethylphenyl isocyanide)iron(0)], [Fe(C9H9N)5][Fe2(C9H9N)9]. The (M)C- N-C(Xyl) angles of the isocyanide ligand are nearly linear for the metals in the +2 oxidation state, for which the ligands function essentially as pure donors. The -CN stretching frequencies for these divalent metal isocyanides are at or above that of the free ligand. Relative to FeII, in the structure containing iron in the formally zero-valent oxidation state, the Fe-C bond lengths have shortened, the C N bond lengths have elongated, the (M)C-N-C(Xyl) angles of the terminal CNXyl ligands are more bent, and the -CN stretching frequencies have shifted to lower energies, all indicative of substantial M(d-).- backbonding.