5397-43-3

Basic information

• Product Name: 2H-PYRAN-2-CARBONITRILE, TETRAHYDRO-
• Synonyms: 2H-PYRAN-2-CARBONITRILE, TETRAHYDRO-;tetrahydro-2H-pyran-2-carbonitrile;tetrahydro-2H-pyran-2-carbonitrile(WXC08528)
• CAS NO: 5397-43-3
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14176
• Mol File: 5397-43-3.mol

Chemical Properties

• Boiling Point: 224°Cat760mmHg
• Flash Point: 92.2°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 5.01E-10mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 2H-PYRAN-2-CARBONITRILE, TETRAHYDRO-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-PYRAN-2-CARBONITRILE, TETRAHYDRO-(5397-43-3)
• EPA Substance Registry System: 2H-PYRAN-2-CARBONITRILE, TETRAHYDRO-(5397-43-3)

Safety Data

• Hazardous Substances Data: 5397-43-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H22N2O4/c1-22-16-10-14(11-17(12-16)23-2)18(21)20-7-5-19(6-8-20)13-15-4-3-9-24-15/h3-4,9-12H,5-8,13H2,1-2H3

Upstream product

• 6581-66-4 2-methoxytetrahydropyran 
• 7677-24-9 trimethylsilyl cyanide 
• 3136-02-5 2-chlorotetrahydro-2H-pyran 
• 506-64-9 silver(I) cyanide 
• 110-87-2 3,4-dihydro-2H-pyran 
• 142-68-7 TETRAHYDROPYRANE 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 592-04-1 mercury(II) cyanide 
• 87319-39-9 2,6-dibromohexanenitrile 
• 2761-33-3 2-acetoxytetrahydropyran 

Downstream Products

• 55962-00-0 2-benzyl-3,4,5,6-tetrahydro-2H-pyran 
• 144688-86-8 2-benzyl-2-cyano-3,4,5,6-tetrahydro-2H-pyran 

Relevant articles and documents

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

A metal-free direct C (sp3)-H cyanation reaction with cyanobenziodoxolones

A metal-free protocol of direct C(sp3)-H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.

Stereocontrolled cyanohydrin ether synthesis through chiral Bronsted acid-mediated vinyl ether hydrocyanation

Vinyl ethers can be protonated to generate oxocarbenium ions that react with Me3SiCN to form cyanohydrin alkyl ethers. Reactions that form racemic products proceed efficiently upon conversion of the vinyl ether to an α-chloro ether prior to cya

Experimental Studies of the Anomeric Effect. Part VI. Ring Inversion Equilibria in Cyclohexane, Tetrahydropyran and Piperidine Rings Substituted by a Carbomethoxy or a Cyano Group.

The ring inversion equilibrium in carbomethoxycyclohexane is compared with those in 2-carbomethoxytetrahydropyran and 2-carbomethoxypiperidine through a variable temperature nmr study of the positions of equilibria.The derived ΔH0ae values (kcal mol-1) of -1.24 (cyclohexane), -1.69 (tetrahydropyran) and -0.54 (piperidine) can be rationalised in terms of competition between steric effects and endo-anomeric effects of the ring heteroatom.Variable temperature studies have also given ΔH0ae values (kcal mol-1) for ring inversions in cyanocylohexane, 2-cyanotetrahydropyran and 2-cyanopiperidine as -0.18, +0.36 and +2.22.Steric effects are small for CN, and the trend in ΔH0 values is consistent with the expected increase in stabilising endo-anomeric effect along the series C, O, N.

Preparation of Tetrahydropyran Derivatives with α-Electron-Withdrawing Substituents from 1,5-Dibromopentane Derivatives by Treatment with Silver Nitrate

When 1,5-dibromopentane derivatives having the electron-withdrawing groups at one terminus, wich were obtained by Cu(I)-catalyzed photochemical addition of 1,3-dibromopropanes to electron-deficient olefins, were subjected to treatment with silver nitrate, tetrahydropyran derivatives with the electron-withdrawing groups at the α-position to the oxygen atom were obtained.

TRIMETHYLSILYL CYANIDE PROMOTED CYANATION OF TERTIARY ALKYL CHLORIDES AND OTHER SN1 ACTIVE COMPOUNDS

Tertiary chlorides are readily cyanated in a one-pot procedure using trimethylsilyl cyanide in the presence of SnCl4.The mechanism of this novel and synthetically useful reaction involves initial isonitrile formation followed by rearrangement to the tertiary nitrile.Other SN1 active compounds also undergo smooth cyanation.

CYANOTRIMETHYLSILANE AS A VERSATILE REAGENT FOR INTRODUCING CYANIDE FUNCTIONALITY

Cyanotrimethylsilane adds to some α,β-unsaturated ketones in conjugate manner under the catalytic action of Lewis acids such as triethylaluminium, aluminium chloride, and SnCl2.Hydrolysis of the products gives β-cyano ketones which are identical to the hydrocyanated products of the starting enones.The title silicon reagent reacts with acetals and orthoesters under the catalytic action of SnCl2 or BF3*OEt2 affording 2-alkoxy- and 2,2-dialkoxyalkanenitriles.Application of the reaction to O-protected β-D-ribofuranoses gives selectively β-D-ribofuranosyl cyanide in excellent yield.