74739-36-9

Upstream product

• 7418-32-8 N-(2-nitrophenyl)formamide 

Downstream Products

• 74739-61-0 N,N-Diethyl-N'-(2-nitro-phenyl)-formamidine 
• 1029317-01-8 2-(N-(4-methoxybenzyl)-2,2,2-trifluoroacetamido)-N-(2-nitrophenyl)-4-phenylbutanamide 
• 1029316-96-8 (4aR,7R,7aS)-5-(4-methoxybenzyl)hexahydro-2,2,7-trimethyl-N-(2-nitrophenyl)-6-oxo[1,3]dioxino[5,4-b]pyrrole-4a-carboxamide 
• 1029316-93-5 1-(4-methoxybenzyl)-2-methyl-N-(2-nitrophenyl)-5-oxopyrrolidine-2-carboxamide 
• 805315-05-3 tetrakis(2-nitrophenyl isocyanide)nickel(O) 
• 1609132-56-0 C₂₉H₂₃N₃O₅ 
• 74755-79-6 (2-Nitro-phenyl)-[1-piperidin-1-yl-meth-(E)-ylidene]-amine 
• 74739-83-6 (2-Nitro-phenyl)-[1-pyrrolidin-1-yl-meth-(E)-ylidene]-amine 
• 74739-60-9 N,N-Diethyl-N'-(2-nitro-phenyl)-formamidine 
• 74739-71-2 [1-Aziridin-1-yl-meth-(E)-ylidene]-(2-nitro-phenyl)-amine 
• 74739-50-7 N,N-Dimethyl-N'-(2-nitro-phenyl)-formamidine 
• 74407-97-9 N,N-Dimethyl-N'-(2-nitro-phenyl)-formamidine 
• 74755-80-9 (2-Nitro-phenyl)-[1-piperidin-1-yl-meth-(Z)-ylidene]-amine 
• 74739-84-7 (2-Nitro-phenyl)-[1-pyrrolidin-1-yl-meth-(Z)-ylidene]-amine 

Relevant academic research and scientific papers

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

Synthesis of isonitriles from N-substituted formamides using triphenylphosphine and iodine

Treatment of N-substituted formamides with the reagent combination of triphenylphosphine and molecular iodine, in the presence of a tertiary amine, quickly produces the corresponding isocyanides in high yields under ambient conditions. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis of various alkyl and aryl isocyanides.

Metal-template-controlled stabilization of β-functionalized isocyanides

Reaction of 2-azidoethyl isocyanide 1, 2-azidophenyl isocyanide 2, or 2-nitrophenyl isocyanide 3 with complexes [Mo(CO)3(dppe)(py)] [4] or [W(CO)3(dppe)(Ni-≡CCH3)] [5] yields the isocyanide complexes [Mo(CO)3(dp

Synthesis of benzannulated N-heterocyclic carbene ligands by a template synthesis from 2-nitrophenyl isocyanide

The reaction of 2-nitrophenyl isocyanide 2 with [M(CO)5(thf)] (M = Cr, Mo, W) yields the isocyanide complexes [M(CO)5(2)] (3: M = Cr; 4: M = Mo; 5: M = W). Complexes 3-5 react with elemental tin under reduction of the nitro function of the isocyanide ligand to give the complexes with the unstable 2-aminophenyl isocyanide ligand. The coordinated 2-aminophenyl isocyanide ligand in all three complexes reacts spontaneously under intramolecular nucleophilic attack of the primary amine at the isocyanide carbon atom to yield the complexes with the NH,NH-benzimidazol-2-ylidene ligand (6: M = Cr; 7: M = Mo; 8: M = W). An incomplete reduction of the nitro group in 3-5 is observed when hydrazine hydrate is used instead of tin. Here the formation of complexes with a coordinated 2-hydroxylamine-functionalized phenyl isocyanide [(CO)5M-CN-C6H4--2-N(H)-OH] is postulated and this unstable ligand again undergoes intramolecular cyclization to give the NH,NOH-stabilized benzimidazol-2-ylidene complexes 9-11. The tungsten derivative 11 can be allylated stepwise by a deprotonation/ alkylation sequence first at the OH and then at the NH position to yield the monoallylated and diallylated species 12 and 13. The molecular structures of 3-5 and 12-13 were established by X-ray crystallography.