825-76-3

Basic information

• Product Name: alpha-cyclopropylstyrene
• Synonyms: alpha-cyclopropylstyrene;(1-Cyclopropylethenyl)benzene;(1-Phenylvinyl)cyclopropane;1-Cyclopropyl-1-phenylethene;α-Cyclopropylstyrene
• CAS NO: 825-76-3
• Molecular Formula: C₁₁H₁₂
• Molecular Weight: 144.21298
• EINECS: 212-547-4
• Mol File: 825-76-3.mol

Chemical Properties

• Boiling Point: 88-90 °C(Press: 8 Torr)
• Appearance: /
• Density: 0.9618 g/cm3(Temp: 21 °C)
• CAS DataBase Reference: alpha-cyclopropylstyrene(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-cyclopropylstyrene(825-76-3)
• EPA Substance Registry System: alpha-cyclopropylstyrene(825-76-3)

Safety Data

• Hazardous Substances Data: 825-76-3(Hazardous Substances Data)

Upstream product

• 5558-04-3 1-cyclopropyl-1-phenylethanol 
• 3481-02-5 cyclopropyl phenyl ketone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 132933-61-0 (2-Cyclopropyl-2-hydroxy-2-phenylethyl)trimethylsilane 
• 6226-34-2 1-Cyclopropyl-1-phenylethanol 
• 98-81-7 1-bromovinylbenzene 
• 106-96-7 propargyl bromide 
• 1822-00-0 trimethylsilylmethyllithium 
• 108-86-1 bromobenzene 
• 765-43-5 Cyclopropyl methyl ketone 
• 71-43-2 benzene 
• 67-71-0 dimethylsulfone 
• 1007-03-0 1-phenyl-1-cyclopropylmethanol 
• 2065-66-9 methyl-triphenylphosphonium iodide 

Downstream Products

• 106737-31-9 4-phenyl-cyclohePt-4-ene-1,2-dicarboxylic acid-anhydride 
• 111638-34-7 8-cyclopropyl-1,2,3,4,4a,5,6,7-octahydro-1,4-etheno-naphthalene-2,3,5,6-tetracarboxylic acid-2,3;5,6-dianhydride 
• 3481-02-5 cyclopropyl phenyl ketone 
• 58368-42-6 1-Cyclopropyl-1-phenyl-ethan-1,2-diol 
• 65322-27-2 2,2-Dichloro-1-phenyl-bicyclopropyl 
• 17421-69-1 4-Phenyl-2-methyl-cis-4-hepten 
• 67903-42-8 5-Chlor-(Z)-2-phenyl-2-penten 
• 6226-34-2 1-Cyclopropyl-1-phenylethanol 
• 56061-55-3 1-((Z)-2-Cyclopropyl-2-phenyl-vinylsulfanyl)-2,4-dinitro-benzene 
• 56061-54-2 1-((Z)-5-Chloro-2-phenyl-pent-2-enylsulfanyl)-2,4-dinitro-benzene 
• 111704-97-3 1-chloro-1-cyclopropyl-2-methoxy-1-phenylethane 
• 87959-46-4 (2,2-dibromo-[1,1'-bi(cyclopropan)]-1-yl)benzene 
• 30656-45-2 (E)-5-phenylhex-4-en-1-ol 
• 16510-30-8 α-cyclopropyl ethyl benzene 

Relevant articles and documents

Visible Light Induced Br?nsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones

A mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. A broad range of vinyl arenes and heteroarenes with high functional group tolerance, as well as a range of different diazo compounds, can efficiently undergo this transformation. This method features Br?nsted acid-assisted generation of hybrid palladium C(sp3)-centered radical intermediate, which allowed for new selective C?H functionalization protocol.

Regioselective Three-Component Synthesis of Vicinal Diamines via 1,2-Diamination of Styrenes

The vicinal diamine motif plays a significant role in natural products, drug design, and organic synthesis, and development of synthetic methods for the synthesis of diamines is a long-standing interest. Herein, we report a regioselective intermolecular three-component vicinal diamination of styrenes with acetonitrile and azodicarboxylates. The diamination products can be produced in moderate to excellent yields via the Ritter reaction. Synthetic applications and theoretical studies of this reaction have been conducted.

Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications

Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.

B(C6F5)3-Catalyzed Diastereoselective Formal (4 + 1)-Cycloaddition of Vinylcyclopropanes and Et2SiH2

A formal (4 + 1)-cycloaddition of vinylcyclopropanes and Et2SiH2 to afford 3,4-disubstituted silolanes is reported. The reaction sequence commences with the known B(C6F5)3-catalyzed alkene hydrosilylation with dihydrosilanes. Cleavage of the remaining Si-H bond in the hydrosilylation product assisted by B(C6F5)3 leads to formation of a cyclopropane-stabilized silylium ion. The activated cyclopropane ring is then opened by the in situ-generated borohydride accompanied by ring closure to the silolane. The diastereoselectivity is rationalized by a mechanistic model.

Photoinduced [3+2] Annulation of Alkene with o-Iodoanilines: An Expedient Approach to Indolines

A highly regioselective [3+2] cyclization of alkenes with 2-iodoanilines under the irradiation of UV light is described. This general, metal-free strategy facilitates the direct preparation of 2-mono-/disubstituted indolines as well as spiroindolines through alkene carboamination in one step. Mechanistic studies suggested that the photochemical protocol proceeded via a radical pathway.

Visible-Light-Induced Meerwein Fluoroarylation of Styrenes

An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.

Electrochemical fluorosulfonylation of styrenes

An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Base-Mediated Site-Selective Hydroamination of Alkenes

We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tertbutoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access-arylamines from terminal aliphatic alkenes.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):