2321-76-8

Basic information

• Product Name: 2-iminocyclopentanecarbonitrile
• Synonyms: 2-iminocyclopentanecarbonitrile;2-Cyanocyclopentaneimine;2-Imino-1-cyclopentanecarbonitrile;2-Iminocyclopentane-1-carbonitrile
• CAS NO: 2321-76-8
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.14112
• EINECS: 219-033-9
• Mol File: 2321-76-8.mol

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 320.9°Cat760mmHg
• Flash Point: 147.9°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.000308mmHg at 25°C
• Refractive Index: 1.585
• PKA: 9.67±0.40(Predicted)
• CAS DataBase Reference: 2-iminocyclopentanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-iminocyclopentanecarbonitrile(2321-76-8)
• EPA Substance Registry System: 2-iminocyclopentanecarbonitrile(2321-76-8)

Safety Data

• Hazardous Substances Data: 2321-76-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 5483, 1958 DOI: 10.1021/ja01553a043

InChI:InChI=1/C6H8N2/c7-4-5-2-1-3-6(5)8/h5,8H,1-3H2/b8-6+

Upstream product

• 64-17-5 ethanol 
• 111-69-3 hexanedinitrile 
• 141-52-6 sodium ethanolate 
• 7732-18-5 water 
• 108-88-3 toluene 
• 60-29-7 diethyl ether 
• 110-71-4 1,2-dimethoxyethane 
• 64661-04-7 2,5-dicyano-adipic acid diethyl ester 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 1418199-98-0 trans-2-[6-benzenesulfonyl-2-((R)-1-hydroxy-ethyl)-6H-1,3,5,6-tetraaza-as-indacen-1-yl]-cyclopentanecarbonitrile 
• 120-92-3 cyclopentanone 
• 335421-55-1 2-oxo-1-(3-oxopentyl)cyclopentanecarbonitrile 
• 335421-62-0 7-methyl-6-oxo-1,2,3,4,5,6-hexahydro-3aH-indene-3a-carbonitrile 
• 21544-02-5 2-(aminomethyl)-cyclopentylamine 
• 924669-64-7 2-((6-chloropyridin-3-yl)methylamino)cyclopentanecarbonitrile 
• 80501-45-7 2-amino-cyclopentanecarbonitrile 
• 2941-29-9 2-oxocyclopentanecarbonitrile 

Relevant articles and documents

ENHANCED EXTRACTION OF IMPURITIES FROM MIXTURE COMPRISING NITRILES

Disclosed herein are methods for recovering phosphorus-containing ligand from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the phosphorus-containing ligand.

INTEGRATED PROCESS FOR NITRILE MANUFACTURE WITH ENHANCED LIQUID-LIQUID EXTRACTION

Phosphorus-containing ligands are recovered from mixtures comprising 3-pentenenitrile (3PN) and adiponitrile (ADN), using liquid-liquid extraction. ADN is produced by hydrocyanation of 3PN. The ADN is hydrogenated to produce a hexamethyiene diamine (HMD) and at Ieast one byproduct including bis-hexamethylene triamine (BHMT) or 1,2-diaminocyclohexane. At Ieast a portion of the HMD product or byproduct is used to enhance the liquid-liquid extraction to recover phosphorus-containing ligand.

An Alternative to the Classical α-Arylation: The Transfer of an Intact 2-Iodoaryl from ArI(O2CCF3)2

The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ3-iodanes. Here, we describe an alternative metal-free α-arylation using ArI(O2CCF3)2 as the source of a 2-iodoaryl group. The reaction is applicable to activated ketones, such as α-cyanoketones, and works with substituted aryliodanes. This formal C-H functionalization reaction is thought to proceed through a [3,3] rearrangement of an iodonium enolate. The final α-(2-iodoaryl)ketones are versatile synthetic building blocks.

FUSED TRICYCLIC COMPOUNDS FOR USE AS INHIBITORS OF JANUS KINASES

The invention provides novel compounds of formula (I) having the general formula (I) wherein R1, V, W, X, Y and Z are as described herein. Accordingly, the compounds may be provided in pharmaceutically acceptable compositions and used for the treatment of immunological or hyperproliferative disorders.

Syntheses and biological activities of octahydro-1H-cyclopenta[d]pyrimidine derivatives

Various nitromethylene derivatives were synthesized regioselectively. Compounds 8a-f were obtained by the reaction of 1-((5-chloropyridin-2-yl)methyl) -2-(nitromethylene)-octahydro-1H-cyclopenta[d]-pyrimidine (3) with primary amines and formaldehyde. The synthesized compounds were identified by 1H NMR, HRMS (EI), and IR, and preliminary bioassays indicated that most of them showed moderate insecticidal activities against Aphis craccivora. The relationship between hydrophobicity and biological activity was also discussed.

A modified Robinson annulation process to α,α-disubstituted-β,γ-unsaturated cyclohexanone system. Application to the total synthesis of nanaimoal

4-Cyano-2-cyclohexenones were found to be susceptible to reductive alkylation reactions, giving the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. This newly developed methodology has been successfully applied towards the total synthesis, in racemic form, of the marine natural product nanaimoal.

Method for preparing aminonitrile and diamine

The present invention relates to a process for the preparation of aminonitrile and of diamine by catalytic hydrogenation of dinitrile. It consists of a process for the preparation of aminonitrile and of diamine by catalytic hydrogenation of aliphatic dinitrile having from 3 to 12 carbon atoms, characterized in that the final reaction mixture, the catalyst of which has been separated beforehand, is acidified by addition of a sufficient amount of an inorganic or organic acid, before being subjected to an operation of distillation of the products of the reaction and of the unconverted dinitrile. It relates more particularly to the preparation of 6-aminocapronitrile and of hexamethylenediamine by hydrogenation of adiponitrile. The 6-aminocapronitrile can be hydrolysed in the liquid phase or in the gas phase to result in caprolactam. The hexamethylenediamine can be used very particularly to prepare polyamide-6,6 by reaction with adipic acid.