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

• 112547-81-6 N-acetyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine 
• 112547-80-5 N-(2,6-dimethylphenylaminomethylene)-N'-methoxycarbonylhydrazine 
• 87-62-7 2,6-dimethylaniline 
• 542-69-8 1-iodo-butane 
• 154592-61-7 2,6-xylyl isoselenocyanate 
• 4440-01-1 lithium phenylacetylide 
• 112547-83-8 ethyl 2-acetylhydrazono-2-(2,6-dimethylphenylamino)acetate 
• 112547-82-7 N-benzoyl-N'-(2,6-dimethylphenylaminomethylene)hydrazine 
• 607-92-1 2,6-dimethylformanilide 
• 67-66-3 chloroform 
• 53178-41-9 2-lithio-2-phenyl-1,3-dithiane 
• 594-19-4 tert.-butyl lithium 
• 64-18-6 formic acid 
• 1434546-80-1 Ti(O(2-C₆H₄NSiMe₃)₂)(diphenyl hydrazido^(2-))(pyridine)(CN-2,6-C₆H₃Me₂) 

Downstream Products

• 25348-08-7 N,N'-di (2,6-dimethylphenyl) urea 
• 103400-37-9 1-(2',6'-Dimethyl-phenyl-imino)-3,3,5,5-tetraphenyl-cyclopentadion-(2,4) 
• 121573-74-8 (1,3-Diethyl-4,5,6,7-tetrahydro-inden-2-ylidene)-(2,6-dimethyl-phenyl)-amine 
• 112399-66-3 (2,6-Dimethyl-phenyl)-[6-phenyl-3a,4-dihydro-1H,3H-cyclopenta[c]furan-(5E)-ylidene]-amine 
• 121573-73-7 (1,3-Bis-trimethylsilanyl-4,5,6,7-tetrahydro-inden-2-ylidene)-(2,6-dimethyl-phenyl)-amine 
• 136213-32-6 2,2,3,3,4,4,5,5,6,6-decamethyl-1-(2,6-xylylimino)-2,3,4,5,6-pentasilacyclohexane 
• 130762-83-3 3-[(E)-2,6-Dimethyl-phenylimino]-2-[(Z)-2,6-dimethyl-phenylimino]-pentanoic acid methyl ester 
• 135579-02-1 C₂₇H₂₆N₂O₂ 
• 125569-40-6 1-Benzyloxy-2-[(E)-2,6-dimethyl-phenylimino]-3-ethyl-pentan-3-ol 
• 13220-57-0 tryptanthrine 
• 135579-01-0 C₂₇H₂₆N₂O 
• 135981-35-0 2,3-Bis-N-(2',6'-xylyl)imino-5-phenyl-2,3-dihydrofuran. 

Relevant articles and documents

Heterocyclopentanediyls vs heterocyclopentadienes: A question of silyl group migration

The reaction of the singlet biradical [P(μ-NHyp)]2 (Hyp = hypersilyl, (Me3Si)3Si) with different isonitriles afforded a series of five-membered N2P2C heterocycles. Depending on the steric bulk of the substituent at the isonitrile, migration of a Hyp group was observed, resulting in two structurally similar but electronically very different isomers. As evidenced by comprehensive spectroscopic and theoretical studies, the heterocyclopentadiene isomer may be regarded as a rather unreactive closed-shell singlet species with one localized N=P and one C=P double bond, whereas the heterocyclopentanediyl isomer represents an open-shell singlet biradical with interesting photochemical properties, such as photoisomerization under irradiation with red light to a [2.1.0]- housane-type species.

Reversible switching between housane and cyclopentanediyl isomers: An isonitrile-catalysed thermal reverse reaction

The photo-isomerization of an isolable five-membered singlet biradical based on C, N, and P ([TerNP]2CNDmp, 2a) selectively afforded a closed-shell housane-type isomer (3a) by forming a transannular P-P bond. In the dark, the housane-type species re-isomerized to the biradical, resulting in a fully reversible overall process. In the present study, the influence of tBuNC on the thermal reverse reaction was investigated: The isonitrile acted as a catalyst, thus allowing control over the thermal reaction rate. Moreover, tBuNC also reacted with the biradical to form an adductspecies ([TerNP]2CNDmp·CNtBu, 4a), which can be regarded as the resting state of the system. The reactive species 2a and 3a could be re-generated in situ by irradiation with red light. The results of this study extend our understanding of this new class of molecular switches.

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.