2415-80-7

Basic information

• Product Name: (2,2-Dichlorocyclopropyl)benzene
• Synonyms: Benzene,(2,2-dichlorocyclopropyl)-;Cyclopropane, 1,1-dichloro, 2-phenyl;1,1-DICHLORO-2-PHENYLCYCLOPROPANE;(2,2-DICHLOROCYCLOPROPYL)BENZENE;1,1-Dichlorophenyl cyclopropane;(2,2-Dichlorocyclopropyl)benzene,97%;1,1-dichloro-2-phenyl cyclopropanen(ciprofibrate)
• CAS NO: 2415-80-7
• Molecular Formula: C₉H₈Cl₂
• Molecular Weight: 187.07
• EINECS: 219-326-1
• Product Categories: Halides;Aryl;C9 to C12;Halogenated Hydrocarbons
• Mol File: 2415-80-7.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 103 °C10 mm Hg(lit.)
• Flash Point: 220 °F
• Appearance: clear colorless to very slightly yellow liquid
• Density: 1.208 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0804mmHg at 25°C
• Refractive Index: n20/D 1.551(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1860351
• CAS DataBase Reference: (2,2-Dichlorocyclopropyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (2,2-Dichlorocyclopropyl)benzene(2415-80-7)
• EPA Substance Registry System: (2,2-Dichlorocyclopropyl)benzene(2415-80-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2415-80-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to very slightly yellow liquid

Uses

(2,2-Dichlorocyclopropyl)benzene may be used in the synthesis of p-(2,2-dichlorocyclopropyl)aniline.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 12, 1990Synthetic Communications, 25, p. 3821, 1995 DOI: 10.1080/00397919508011456Tetrahedron Letters, 16, p. 3013, 1975

InChI:InChI=1/C9H8Cl2/c10-9(11)6-8(9)7-4-2-1-3-5-7/h1-5,8H,6H2

Upstream product

• 100-42-5 styrene 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 123849-08-1 (-)-(R)-dichloromethyl p-tolyl sulfoxide 
• 96-09-3 styrene oxide 
• 67-66-3 chloroform 
• 56-23-5 tetrachloromethane 
• 74-95-3 1,1-dibromomethane 
• 1126-71-2 N,N-dimethylphenethylamine 
• 75-25-2 Bromoform 
• 75-09-2 dichloromethane 

Downstream Products

• 54458-54-7 γ-1-Chlor-1-methyl-t-2-phenylcyclopropan 
• 54458-54-7 γ-1-Chlor-1-methyl-c-2-phenylcyclopropan 
• 5324-00-5 2,3-diphenyl-1H-indene 
• 1961-97-3 3-phenyl-1H-indene 
• 18523-34-7 1,1-dimethoxy-2-phenylcyclopropane 
• 81676-49-5 trans-1-isopropoxy-1-methoxy-2-phenylcyclopropane 
• 81676-49-5 cis-1-isopropoxy-1-methoxy-2-phenylcyclopropane 
• 3356-89-6 3-phenyl-5-chloroisoxazole 
• 40641-94-9 p-2.2-Dichlorcyclopropylphenylessigsaeure 
• 40641-96-1 [4-(2,2-Dichloro-cyclopropyl)-phenyl]-acetic acid methyl ester 
• 40642-02-2 α-(p-2,2-Dichlorcyclopropylphenyl)aethanol 
• 40642-03-3 1-(1-Chloro-ethyl)-4-(2,2-dichloro-cyclopropyl)-benzene 
• 142598-83-2 3-(4-nitrophenyl)-5-chloroisoxazole 
• 22513-12-8 3-phenyl-1,1,5,5-tetrachloropenta-1,4-diene 

Relevant articles and documents

Generation of 'naked' fluoride ions in unprecedentedly high concentrations from a fluoropalladium complex

An F-/Cl- ligand exchange in the stable organopalladium fluoro complex 1 generates naked fluoride ions in unusually high concentrations. The released Freadily fluorinates dichloromethane under exceedingly mild conditions and deprotonates chloroform to produce dichlorocarbene.

Phase-transfer catalytic dichlorocyclopropanation of styrene under the influence of ultrasound conditions - A kinetic study

The kinetics for dichlorocyclopropanation of styrene with an excess of chloroform were studied under phase-transfer catalysis and ultrasound irradiation conditions using aqueous sodium hydroxide as the base and benzyltriethylammonium bromide as a catalyst. The reaction was carried out at 35 °C under pseudo-first order conditions by keeping aqueous sodium hydroxide and chloroform in excess and was monitored by gas chromatography (GC). The effects of agitation speed, quaternary ammonium salts, amount of catalyst, amount of sodium hydroxide and temperature on the kinetics of the conversion were investigated.

DIHALOMETHANES AS C-H ACIDS IN THE CATALYTIC TWO-PHASE (CTP) SYSTEM - A NEW METHOD FOR THE SYNTHESIS OF gem-DICHLOROCYCLOPROPANES

Dihalomethanes react with carbon tetrachloride and alkenes in the CTP system affording gem-dichlorocyclopropanes.

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Isotope effects and the mechanism of deoxygenation of epoxides with dichlorocarbene

The deoxygenation of styrene oxide with dichlorocarbene is studied by a combination of isotope effects and theoretical calculations. A normal 13C isotope effect of 1.016 is observed for the α-carbon of the styrene oxide but a surprising inverse isotope effect of 0.995 is observed at the β-carbon. This is indicative of a highly asynchronous process in which the Cα-O bond is broken without any progress in the breakage of Cβ-O bond. Theoretical calculations support this interpretation. This coarctate reaction is formally concerted as it avoids involving a high-energy intermediate, but it appears uninfluenced by transition state aromaticity.

Grafted Polyethylene Glycol–Graphene Oxide as a Novel Triphase Catalyst for Carbenes and Nucleophilic Substitution Reactions

Abstract: Separation and reusability had been main problems for the using of polyethylene glycol (PEG) as phase transfer catalysts (PTCs). To solve these problems, PEG was firstly and successfully grafted on graphene oxide (GO) using BF3·C2H5OC2H5 as Lewis acid catalyst. The solid GO-PEG composites were systemically investigated by characterization techniques (TG, FT-IR, XPS, ICP-AES etc.) and then applied to some carbenes and nucleophilic substitution reactions as novel triphase catalysts. As the results, GO-PEG showed not only equally excellent catalytic activity (≥ 93% yield of 7,7-dichlorobicyclo[4.1.0]heptane and iodooctane) but also incomparable reusability (≥ 85% yield of iodooctane after using for four times) in comparison with traditional PTCs (PEG). Graphic Abstract: [Figure not available: see fulltext.].

Rate Acceleration of Solid-Liquid Phase-Transfer Catalysis by Rotor-Stator Homogenizer

A rotor-stator homogenizer was found to be an effective mixing tool that accelerated solid-liquid phase-transfer reactions. In the asymmetric alkylation under phase-transfer conditions using the homogenizer, a considerably high turnover frequency was observed. (Figure presented.).