873-49-4

Basic information

• Product Name: CYCLOPROPYLBENZENE
• Synonyms: PHENYLCYCLOPROPANE;1-CYCLOPROPYLBENZENE;CYCLOPROPYLBENZENE;1-Phenylcyclopropane;Cyclopropane, phenyl-;Cyclopropylbenzen;BENZENE,CYCLOPROPYL-
• CAS NO: 873-49-4
• Molecular Formula: C₉H₁₀
• Molecular Weight: 118.18
• EINECS: 212-839-1
• Product Categories: Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 873-49-4.mol
• Article Data: 78

Chemical Properties

• Melting Point: -31°C
• Boiling Point: 173.6 °C753 mm Hg(lit.)
• Flash Point: 111 °F
• Appearance: /
• Density: 0.94 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.55mmHg at 25°C
• Refractive Index: n20/D 1.533(lit.)
• Storage Temp.: Room temperature.
• CAS DataBase Reference: CYCLOPROPYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPROPYLBENZENE(873-49-4)
• EPA Substance Registry System: CYCLOPROPYLBENZENE(873-49-4)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 873-49-4(Hazardous Substances Data)

Usage

Description

Cyclopropylbenzene is a cyclopropylarene, a type of aromatic compound with a cyclopropane ring fused to a benzene ring. It has been studied for its oxidation by rabbit liver microsomal cytochrome P-450, and its gas-phase structure has been analyzed using ab initio computational, microwave spectroscopic, and electron diffraction techniques.

Uses

Used in Chemical Synthesis:
Cyclopropylbenzene is used as a chemical intermediate in the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for the formation of diverse chemical products through reactions like oxidation, reduction, and substitution.
Used in Research and Development:
Cyclopropylbenzene serves as a valuable compound in academic and industrial research for studying the properties and reactions of cyclopropylarenes. Its use in research helps to advance the understanding of the structure, reactivity, and potential applications of this class of compounds.
Used in Material Science:
Cyclopropylbenzene can be used as a building block for the development of new materials with specific properties, such as polymers with unique mechanical, thermal, or electrical characteristics. Its incorporation into polymer structures can lead to the creation of innovative materials for various applications.
Used in Pharmaceutical Industry:
Cyclopropylbenzene is used as a key component in the synthesis of certain pharmaceutical drugs. Its unique structure can contribute to the development of new drugs with improved efficacy, selectivity, and reduced side effects.
Used in Agrochemical Industry:
Cyclopropylbenzene can be utilized in the development of agrochemicals, such as pesticides and herbicides, with enhanced performance and reduced environmental impact. Its incorporation into agrochemical formulations can lead to the creation of more effective and sustainable products for agricultural use.

InChI:InChI=1/C9H10/c1-2-4-8(5-3-1)9-6-7-9/h1-5,9H,6-7H2

Upstream product

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• 14371-10-9 (E)-3-phenylpropenal 
• 2415-80-7 1,1-dichloro-2-phenylcyclopropane 
• 186581-53-3 diazomethane 
• 591-50-4 iodobenzene 
• 203861-73-8 cyclopropylzinc chloride 
• 936-47-0 5-phenyl-4,5-dihydro-1H-pyrazole 
• 64-17-5 ethanol 
• 17714-42-0 1,3-dibromo-1-phenylpropane 
• 74-85-1 ethene 
• 4819-11-8 bis(iodomethyl)mercury 
• 6120-96-3 1-phenyl-1-cyclopropanecarboxamide 
• 108-86-1 bromobenzene 

Downstream Products

• 1530-03-6 1,1-diphenylpropane 
• 6921-44-4 4-nitrophenylcyclopropane 
• 10292-65-6 2-nitrophenylcyclopropane 
• 4489-23-0 1-bromo-4-(prop-1-en-1-yl)benzene 
• 2114-36-5 1-bromopropylbenzene 
• 17714-42-0 1,3-dibromo-1-phenylpropane 
• 21040-45-9 Cinnamyl acetate 
• 62296-03-1 rac-3-acetoxy-1-phenylpropan-1-ol 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 6270-04-8 1,3-diacetoxy-1-phenyl-propane 
• 62872-48-4 1-phenyl-3-iodo-1-(trifluoroacetoxy)propane 
• 62872-49-5 1,3-bis(trifluoroacetoxy)-1-phenylpropane 
• 62872-50-8 1,3-bis(trifluoroacetoxy)-1-(p-iodophenyl)propane 
• 62296-04-2 3-Hydroxy-1-phenylpropylacetat 

Relevant articles and documents

S-Alkylation of α-Thioether Iron Compounds by + and +

Treatment of the thiomethyl complexes (R=Me or Ph0 with + or (CO)2(=CH2)>+ results in S-alkylation, affording the sulphonium salts >+ and Fe(η-C5Me

Dichloromethane activation by chlorochromium(II) complexes with TpiPr2: Generation of an electrophilic Cr-methylene species without the action of an external Cl-abstraction reagent

Five-coordinated chlorochromium(II) complexes with TpiPr2 activate CH2Cl2 to give a metal-carbene species without the action of an external Cl-abstraction reagent, and the resulting methylene fragment is trapped by nucleop

Scalable On-Demand Production of Purified Diazomethane Suitable for Sensitive Catalytic Reactions

We have developed a convenient development-scale reactor (0.44 mol/h) to prepare diazomethane from N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) in ～80% yield. Diazomethane (CH2N2) made with this reactor is extracted into nitrogen gas from the liquid reaction mixture, effectively removing it from reagents and byproducts that may interfere in subsequent reactions. Vertically oriented tubular reactors were used to produce and consume diazomethane in situ. Key features of this reactor include high productivity and correspondingly low reactor volume (reactor volume/liquid flow rate = 6.5 min) and a commercially available gas/liquid separator equipped with a selectively permeating hydrophilic membrane. The design of the reactor keeps the inventory below 53 mg of CH2N2 during normal operation. The reactor was demonstrated by generating CH2N2 that was used in a connected continuous reactor. We evaluated esterification reactions and a continuous Pd-catalyzed cyclopropanation reaction with the reactor and achieved high conversion with 1.5 and 4.1 equiv of MNTS precursor, respectively.

Air-Stable Iron-Based Precatalysts for Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Aryl Boronic Esters

The development of an air-stable iron(III)-based precatalyst for the Suzuki-Miyaura cross-coupling reaction of alkyl halides and unactivated aryl boronic esters is reported. Despite benefits to cost and toxicity, the proclivity of iron(II)-based complexes to undergo deactivationviaoxidation or hydrolysis is a limiting factor for their widespread use in cross-coupling reactions compared to palladium-based or nickel-based complexes. The new octahedral iron(III) complex demonstrates long-term stability on the benchtop as assessed by a combination of1H NMR spectroscopy, M?ssbauer spectroscopy, and its sustained catalytic activity after exposure to air. The improved stability of the iron-based catalyst facilitates an improved protocol in which Suzuki-Miyaura cross-coupling reactions of valuable substrates can be assembled without the use of a glovebox and access a diverse scope of products similar to reactions assembled in the glovebox with iron(II)-based catalysts.