5722-11-2

Basic information

• Product Name: 2,2-Dimethylcyclopropyl cyanide
• Synonyms: 2,2-DIMETHYLCYCLOPROPYL CYANIDE;2,2-DIMETHYLCYCLOPROPANECARBONITRILE;1-CYANO-2,2-DIMETHYLCYCLOPROPANE;2,2-DIMETHYL CYCLOPROPYL CYANIDE 98+%;2,2-dimethylcyclopropane-1-carbonitrile
• CAS NO: 5722-11-2
• Molecular Formula: C₆H₉N
• Molecular Weight: 95.14
• EINECS: 1312995-182-4
• Mol File: 5722-11-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 140.9 °C at 760 mmHg
• Flash Point: 35.7 °C
• Appearance: /
• Density: 0.91 g/cm³
• Vapor Pressure: 5.99mmHg at 25°C
• Refractive Index: gt. 1.4250-1.4290
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,2-Dimethylcyclopropyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethylcyclopropyl cyanide(5722-11-2)
• EPA Substance Registry System: 2,2-Dimethylcyclopropyl cyanide(5722-11-2)

Safety Data

• RIDADR: 1993
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5722-11-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 3467, 1957 DOI: 10.1021/ja01570a041

InChI:InChI=1/C6H9N/c1-6(2)3-5(6)4-7/h5H,3H2,1-2H3

Upstream product

• 22308-12-9 1,3-bis((p-toluenesulfonyl)oxy)-2,2-dimethylpropane 
• 151-50-8 potassium cyanide 
• 141810-07-3 1,1,1-Trifluoro-4-iodo-4-methyl-2-(trifluoromethyl)pentane 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 1755-97-1 5,5-dimethyl-1,3,2-dioxathiane-2,2-dioxide 
• 107-13-1 acrylonitrile 
• 5161-49-9 dimethyldiazirine 

Downstream Products

• 22286-91-5 1-(2,2-dimethyl-cyclopropyl)-pentan-1-one 
• 29843-73-0 1-(2,2-Dimethyl-cyclopropyl)-pent-4-en-1-one 
• 872-75-3 1-(2,2-dimethyl-cyclopropyl)-ethanone 
• 5685-43-8 (2,2-dimethylcyclopropyl)(phenyl)methanone 
• 75885-59-5 2,2-dimethylcyclopropane-1-carboxylic acid 
• 26119-44-8 2,2-dimethylcyclopropane-1-carbaldehyde 
• 95188-09-3 2,2-dimethylcyclopropyl 2-pyridyl ketimine 
• 151538-87-3 3-(2,2-dimethylcyclopropyl)-3-chlorodiazirine 
• 95188-04-8 N-(2,2-dimethylcyclopropyl)methylidineaniline 
• 95188-06-0 N-(2,2-dimethylcyclopropyl)methylaniline 
• 50675-57-5 dl-2,2-dimethylcyclopropane-1-carboxylic acid chloride 
• 1759-55-3 (RS)-2,2-dimethylcyclopropanecarboxamide 
• 930-50-7 [(1RS)-2,2-dimethylcyclopropyl]methanol 
• 59671-39-5 1-(2,2-Dimethyl-cyclopropyl)-1-phenyl-ethanol 

Relevant articles and documents

Nucleophilic intermolecular chemistry and reactivity of dimethylcarbene

Experimental and computational studies find that dimethylcarbene (DMC), the parent dialkylcarbene, is both predicted to be and functions as a very reactive nucleophilic carbene in addition reactions with five simple alkenes. Activation energies and enthal

Kinetics of the Competitive 1,2-Carbon Migrations of an Unsymmetrically Substituted Cyclopropylchlorocarbene

Photolysis of 3-(2,2-dimethylcyclopropyl)-3-chlorodiazirine (4) at 25 deg C in pentane affords 81 percent of the 1,2-C migration products 1-chloro-3,3-dimethylcyclobutene (5) and 2-chloro-3,3-dimethylcyclobutene in a 4.8:1 distribution, as well as 19 percent of the fragmentation products, isobutene, and chloroacetylene.Experiments in the presence of the carbene trap trimethylethylene point to product formation from the electronically excited diazirine (4*), which affords 19-20 percent of fragmentation products, ca. 17 percent of 5 and 6 (3.8:1), and ca. 63 percent of 2,2-dimethylcyclopropylchlorocarbene (3).The carbene ring expands to 5 and 6 (5.2:1).Laser flash photolytic studies afford absolute rate constants for 3 -> 5 (1.3 * 106 s-1) and 3 -> 6 (2.5 * 105 s-1).The 5-fold preference of 3 for CH2 migration (to 5) over CMe2 migration (to 6) is attributed to differential steric affects.Ab initio calculations afford structures and energies for 3 and the CH2 and CMe2 transition state (8-CH2 and 8-CMe2).The calculations agree with the experimental findings in that ΔG* for CH2 migration is found to be 1.4 kcal/mol less than ΔG* for CMe2 migration, corresponding to a computed 10-fold kinetic preference for CH2 migration.The expected additional steric congestion is apparent in the 8-CMe2 transition state.

Conversion of trifluoromethyl groups into nitrile functions during cyclization of hexafluoroiodoalkanes with sodium amide

The cyclization of (CF3)CHCH2CIR1CHR2R3 (1) (1a: R1 = Me, R2 = H; 1b: R1 = H, R2 = R3 = Me; 1c: R1 = R2 = R3 = Bun) with so