2327-99-3

Basic information

• Product Name: 1-Phenylallene
• Synonyms: (1,2-Propadienyl)benzene;1,2-Propadienylbenzene;1-Phenylallene;1-Phenylpropadiene;Phenylallene;Phenylpropadiene
• CAS NO: 2327-99-3
• Molecular Formula: C₉H₈
• Molecular Weight: 116.1598
• Mol File: 2327-99-3.mol
• Article Data: 88

Chemical Properties

• Boiling Point: 195.7°Cat760mmHg
• Flash Point: 64.3°C
• Appearance: /
• Density: 0.889g/cm³
• Vapor Pressure: 0.581mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: 1-Phenylallene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylallene(2327-99-3)
• EPA Substance Registry System: 1-Phenylallene(2327-99-3)

Safety Data

• Hazardous Substances Data: 2327-99-3(Hazardous Substances Data)

Usage

Physical state

Colorless liquid at room temperature

Reactivity

Highly reactive

Uses

Synthesis of various organic compounds, reagent in organic chemistry, potential uses in pharmaceutical and material science applications

Safety

Should be handled with care and in accordance with proper safety protocols due to potential hazards.

InChI:InChI=1/C9H8/c1-2-6-9-7-4-3-5-8-9/h3-8H,1H2

Upstream product

• 53834-50-7 (Z)-1,2-dichloro-3-phenyl-2-propene 
• 10024-18-7 bromoallene 
• 28557-00-8 phenylzinc chloride 
• 627-09-8 Propargyl acetate 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 10147-11-2 propargyl benzene 
• 13099-50-8 2-methyl-1-phenyl-1-propene, β,β-dimethylstyrene 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 3355-31-5 1-chloro-3-phenyl-2-propyne 
• 130762-87-7 (3-phenyl-2-propynyl)hydrazine 
• 107-19-7 propargyl alcohol 
• 81797-75-3 7-ethylidenebicyclo<2.2.1>hepta-2,5-diene 
• 2415-80-7 1,1-dichloro-2-phenylcyclopropane 
• 4392-24-9 Cinnamyl bromide 

Downstream Products

• 22664-13-7 (-)-2-Phenyl-methylen-cyclopropan 
• 22645-12-1 (+)-Phenylspiropentan 
• 22645-12-1 (-)-Phenylspiropentan 
• 51483-54-6 ((E)-2-Iodo-3-phenyl-allyl)-carbamic acid methyl ester 
• 51483-55-7 (2-Iodo-1-phenyl-allyl)-carbamic acid methyl ester 
• 18753-56-5 3-Phenyl-5-(phenylmethyl)isoxazole 
• 42523-74-0 Formic acid 2-oxo-1-phenyl-propyl ester 
• 51787-26-9 3,3,1',2',2'-Pentachloro-2-phenyl-bicyclopropyl-1-ene 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 23970-90-3 2,3-dibromo-1-phenyl-1-propene 
• 135068-25-6 Allyldimethyl(α-methylstyryl)silane 
• 135068-21-2 2-Methylene-1,1-dimethyl-3-phenyl-1-silacyclohexane 
• 135068-23-4 2-Benzylidene-1,1-dimethyl-1-silacyclohexane 
• 120385-88-8 3,4-benzo-1,6-dichloro-7-methylene-8-phenylbicyclo<4.2.0>oct-3-ene-2,5-dione 

Relevant articles and documents

Formation of Nucleophilic Allylboranes from Molecular Hydrogen and Allenes Catalyzed by a Pyridonate Borane that Displays Frustrated Lewis Pair Reactivity

Here we report the in situ generation of nucleophilic allylboranes from H2 and allenes mediated by a pyridonate borane that displays frustrated-Lewis-pair reactivity. Experimental and computational mechanistic investigations reveal that upon H2 activation, the covalently bound pyridonate substituent becomes a datively bound pyridone ligand. Dissociation of the formed pyridone borane complex liberates Piers borane and enables a hydroboration of the allene. The allylboranes generated in this way are reactive towards nitriles. A catalytic protocol for the formation of allylboranes from H2 and allenes and the allylation of nitriles has been devised. This catalytic reaction is a conceptually new way to use molecular H2 in organic synthesis.

Zinc promoted asymmetric propargylation of N-(2-chlorotetrafluoroethanesulfin)imines

Zinc promoted asymmetric Barbier-type homopropargylation of aldimines is demonstrated. 2-Chlorotetrafluoroethanesulfinamide was used as the chiral auxiliary and the corresponding homopropargylamines were obtained in good yields with up to 98% diastereosel

Direct observation and retro-ene reaction of a propargylic diazene. Stereochemical assignment of monoalkyl diazenes

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Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Polymerization of Allenes by Using an Iron(II) β-Diketiminate Pre-Catalyst to Generate High Mn Polymers

Herein, we report an iron(II)-catalyzed polymerization of arylallenes. This reaction proceeds rapidly at room temperature in the presence of a hydride co-catalyst to generate polymers of weight up to Mn=189 000 Da. We have determined the polymer structure and chain length for a range of monomers through a combination of NMR, differential scanning calorimetry (DSC) and gel permeation chromatography (GPC) analysis. Mechanistically, we postulate that the co-catalyst does not react to form an iron(II) hydride in situ, but instead the chain growth is proceeding via a reactive Fe(III) species. We have also performed kinetic and isotopic experiments to further our understanding. The formation of a highly unusual 1,3-substituted cyclobutane side-product is also investigated.

Copper(ii)-catalyzed protoboration of allenes in aqueous media and open air

A method has been developed for the facile Cu(ii)-catalyzed protoboration of monosubstituted allenes in aqueous media under atmospheric conditions. The reaction occurs site selectively, favoring internal alkene protoboration to afford 1,1-disubstituted vinylboronic acid derivatives (up to 93?:?7) with modest to good yields. The method has been applied to a variety of phenylallene derivatives as well as alkyl-substituted allenes. This journal is