4663-22-3

Basic information

• Product Name: ISO-PROPENYLCYCLOPROPANE
• Synonyms: (1-methylethenyl)cyclopropane;1-cyclopropyl-1-methylethylene;1-methyl-1-cyclopropylethylene;1-Methylethenylcyclopropane;2-Cyclopropyl-1-propene;2-Cyclopropylpropene;cyclopropane,(1-methylethenyl)-;Isopropneylcyclopropane
• CAS NO: 4663-22-3
• Molecular Formula: C₆H₁₀
• Molecular Weight: 82.14
• Mol File: 4663-22-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: -102.3°C
• Boiling Point: 70°C (estimate)
• Flash Point: °C
• Appearance: /
• Density: 0.7510
• Vapor Pressure: 159mmHg at 25°C
• Refractive Index: 1.4252
• CAS DataBase Reference: ISO-PROPENYLCYCLOPROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: ISO-PROPENYLCYCLOPROPANE(4663-22-3)
• EPA Substance Registry System: ISO-PROPENYLCYCLOPROPANE(4663-22-3)

Safety Data

• Hazardous Substances Data: 4663-22-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H10/c1-5(2)6-3-4-6/h6H,1,3-4H2,2H3

Upstream product

• 930-39-2 2-cyclopropyl-2-propanol 
• 108-88-3 toluene 
• 7664-93-9 sulfuric acid 
• 17396-98-4 2,2'-dicyclopropyl-2,2'-azopropane 
• 108-98-5 thiophenol 
• 67-56-1 methanol 
• 104131-89-7 <1-(1-Methylethyl)cyclopropyl>nitrosocarbamidsaeure-methylester 

Downstream Products

• 107-83-5 2-Methylpentane 
• 79-29-8 2,3-dimethylbutane 
• 625-27-4 2-methyl-2-pentene 
• 763-29-1 2-Methyl-1-pentene 
• 765-43-5 Cyclopropyl methyl ketone 
• 99848-37-0 2-cyclopropyl-2-hydroxy-propionic acid 
• 3638-35-5 2-cyclopropylpropane 
• 1003-17-4 2,2-dimethyltetrahydrofuran 
• 19434-65-2 3-chloropropanaldehyde 
• 7712-60-9 5-chloro-2-methyl-pent-2-ene 
• 58673-35-1 (1-chloro-1-methyl-ethyl)-cyclopropane 
• 191032-91-4 1,4-Dichloro-4-methyl-pentan-3-one 
• 91556-20-6 2-cyclopropyl-1-(phenylthio)propane 
• 66949-06-2 1-Chloro-4-(2-chloro-1-cyclopropyl-1-methyl-ethylsulfanyl)-benzene 

Relevant articles and documents

Clocking Tertiary Cyclopropylcarbinyl Radical Rearrangements

Three independent methods have been employed to estimate the rate constant, k1, for ring-opening of the 2-cyclopropyl-2-propyl radical, 1, at room temperature. These three estimates are based on chemical trapping of 1 and the ring-opened 4-methylpent-3-ene-1-yl radical by thiophenol (k1 = (1.65 ± 0.41) × 107 M-1 s-1), 9-azabicyclo[3.3.1]nonane-N-oxyl (k1 = (1.76 ± 0.34) × 107 M-1 s-1) and 2,2,6,6-tetramethylpiperidine-N-oxyl (k1 = (2.1 ± 0.4) × 107 M-1 s-1) and absolute rate constants for nonrearranging radicals structurally related to 1. The mean value for k1) ((1.84 ± 0.4) × 107 M-1 s-1) should be used when 1 is employed as a tertiary alkyl free radical clock at ambient temperatures.

Deamination Reactions, 44. Decomposition of 1-Alkylcyclopropanediazonium Ions

1-Methyl- (17), 1,2-dimethyl- (41, 44), 1-propyl- (64), 1-(1-methylethyl)cyclopropanediazonium ions (80), and -1-diazonium ions (93) have been generated by alkaline cleavage of the analogous nitrosocarbamates in methanol.Cyclopropyl-allyl transformation and nucleophilic displacement were the only reactions of 17, 41, 44, and 93 while elimination and 1,2-shifts of an α-hydrogen compete increasingly with 64 and 80.The stereochemistry of ring cleavage and nucleophilic displacement has been explored, using 2-D labels in the case of 17 and 93.Cyclopropanediazonium ions (1) and 41 react stereospecifically, 17 and 44 are moderately stereoselective (ca. 85:15), and 93 is entirely unselective.The data indicate a gradual changeover from concerted to stepwise mechanisms.Appreciable stabilization of the positive charge is required to reach the SN1 extreme.