2082-61-3

Basic information

• Product Name: 2-PHENYL-2-BUTENE
• Synonyms: (1-methyl-1-propenyl)benzene;2-butene,2-phenyl-,(cis+trans);2-phenyl-2-butene(cis+trans);alpha,beta-Dimethylstyrene;Benzene, (1-methyl-1-propenyl)-;benzene,(1-methyl-1-propenyl)-;α,β-dimethylstyrene;2-PHENYL-2-BUTENE
• CAS NO: 2082-61-3
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.2
• Mol File: 2082-61-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 174°Cat760mmHg
• Flash Point: 55.7°C
• Appearance: /
• Density: 0.879g/cm³
• Vapor Pressure: 1.65mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 2-PHENYL-2-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-2-BUTENE(2082-61-3)
• EPA Substance Registry System: 2-PHENYL-2-BUTENE(2082-61-3)

Safety Data

• Hazardous Substances Data: 2082-61-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 2531, 1980 DOI: 10.1016/0040-4039(80)80120-1

InChI:InChI=1/C10H12/c1-3-9(2)10-7-5-4-6-8-10/h3-8H,1-2H3/b9-3+

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 98-86-2 acetophenone 
• 87931-48-4 3-phenyl-pent-3-enoic acid 
• 100-42-5 styrene 
• 74-85-1 ethene 
• 110-86-1 pyridine 
• 515-40-2 neophyl chloride 
• 98-85-1 1-Phenylethanol 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 826-54-0 2-methyl-2-phenyl-propanamide 
• 66957-26-4 (C₄H₉)3SnOC(CH₃)(C₆H₅)CH(CH₃)COOCH₃ 
• 4894-61-5 trans-but-2-enyl chloride 
• 67-56-1 methanol 
• 2039-93-2 1-ethylstyrene 

Downstream Products

• 4564-81-2 1-phenyl-1,2-dimethyloxirane 
• 59341-61-6 3-phenylselenophene 
• 824-90-8 1-phenylbut-1-ene 
• 104-51-8 1-butylbenzene 
• 135-98-8 sec-Butylbenzene 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 143097-80-7 2-bromo-4-phenylbutane 
• 52392-57-1 2-bromo-3-phenyl-but-2c-ene 
• 52392-58-2 2-bromo-3-phenyl-but-2t-ene 
• 2404-87-7 3-phenylthiophene 
• 860687-81-6 (1,2-dibromo-1-methyl-propyl)-benzene 
• 65674-14-8 1,2-dibromo-4-phenylbutane 
• 40527-60-4 3-Brom-2-methyl-1,1,1-trinitro-2-phenyl-butan 
• 127704-39-6 (2,2-Dibromo-1,3-dimethyl-cyclopropyl)-benzene 

Relevant articles and documents

NOBIN-based phosphoramidite and phosphorodiamidite ligands and their use in asymmetric nickel-catalysed hydrovinylation

Phosphoramidite and P-stereogenic phosphorodiamidite ligands derived from (Sa)-2-phenylamino-2′-hydroxy-1,1′-binaphthyl (N-Ph-NOBIN) and bis(1-phenyl-ethyl)amine were synthesised, fully characterised, and the absolute configuration of the stereogenic phosphorus atoms was assigned. The phosphoramidite ligand L2 features three non-bridged substituents at phosphorus comprising the bis(1-phenylethyl)amine and two NOBIN moieties. The NOBIN units are bound to the phosphorus through the oxygen atoms with two pendant nitrogen atoms. In the Ni-catalysed hydrovinylation of styrene no conversion was observed with the phosphorodiamidites, while the phosphoramidite ligands led to active catalysts with a marked co-operative effect on selectivities. Whereas the racemic product was obtained with the (S a,Sa,SC,SC) diastereomer, the (Sa,Sa,RC,RC) diastereomer proved to be one of the best ligands for this reaction, leading to almost perfect selectivity and ees of up to 91%.

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Highly selective cobalt-catalyzed hydrovinylation of styrene

Phosphine complexes of cobalt halide salts activated by diethylaluminum chloride are shown to yield highly active catalysts in the hydrovinylation of styrene, with unprecedented high selectivity to the desired product 3-phenyl-1-butene (3P1B). Double-bond isomerization, a common problem in codimerization reactions, only occurs after full conversion with these catalyst systems, even at elevated temperature. The most active catalysts are based on cobalt halide species combined with either C1- or C 2-bridged diphosphines, heterodonor P,N or P,O ligands, flexible bidentate phosphine ligands or monodentate phosphine ligands. Kinetic investigations show an order >1 in catalyst, which indicates either the involvement of dinuclear species in the catalytic cycle or partial catalyst decomposition via a bimolecular pathway.

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.

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.

The effects of using an ionic liquid as a solvent for a reaction that proceeds through a phenonium ion

A unimolecular reaction that proceeds predominantly through a phenonium ion intermediate was investigated in mixtures of an ionic liquid and methanol. Varying the proportion of the ionic liquid in the reaction mixture led to an increase in the rate constant compared with methanol when very small amounts of ionic liquid were present in the reaction mixture and a decrease when higher proportions of the salt were present. Activation parameters determined for the process showed that the effect of changing the solvent composition on the rate constant was due to a key interaction between the ionic liquid and the transition state of the process, similar to other unimolecular processes. Analysis of the stereochemistry of the products demonstrated that the ionic liquid had no effect on either the ratio of the stereochemistry of the substitution products, or the ratio of the substitution and eliminations mechanisms occurring in solution.