766-90-5

Basic information

• Product Name: cis-1 -Propenylbenzene
• Synonyms: Benzene,(1Z)-1-propenyl- (9CI);Benzene, 1-propenyl-, (Z)-;Benzene, propenyl-, (Z)- (8CI);(1Z)-1-Propenylbenzene;(Z)-(1-Propenyl)benzene;(Z)-1-Phenylpropene;(Z)-1-Propenylbenzene;(Z)-Propenylbenzene;(Z)-b-Methylstyrene;cis-1-Phenyl-1-propene;cis-1-Phenylpropene;cis-1-Propenylbenzene;cis-Propenylbenzene
• CAS NO: 766-90-5
• Molecular Formula: C₉H₁₀
• Molecular Weight: 118.18
• EINECS: 212-848-0
• Mol File: 766-90-5.mol
• Article Data: 316

Chemical Properties

• Boiling Point: 167.5 °C at 760 mmHg
• Flash Point: 49.4 °C
• Appearance: /
• Density: 0.906 g/cm³
• Vapor Pressure: 2.24mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: cis-1 -Propenylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: cis-1 -Propenylbenzene(766-90-5)
• EPA Substance Registry System: cis-1 -Propenylbenzene(766-90-5)

Safety Data

• Hazardous Substances Data: 766-90-5(Hazardous Substances Data)

Usage

General Description

cis-1-Propenylbenzene, also known as α-methylstyrene, is a chemical compound that belongs to the class of aromatic hydrocarbons. It is a colorless liquid with a characteristic odor, and it is commonly used as a monomer in the production of various polymers and copolymers, such as polystyrene and acrylonitrile-butadiene-styrene (ABS) resins. It is also used in the manufacture of thermoplastic elastomers, coatings, adhesives, and specialty chemicals. Cis-1-Propenylbenzene is considered to be a hazardous chemical and should be handled with caution due to its flammability and potential health hazards if not used properly.

InChI:InChI=1/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-8H,1H3/b6-2-

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 873-49-4 cyclopropylbenzene 
• 127209-44-3 (3S,4R)-1-Dimethylsilanyl-2,2,3-trimethyl-4-phenyl-[1,2]azasiletidine 
• 93272-23-2 (2R,3R)-3-(Dimethyl-phenyl-silanyl)-2-methyl-3-phenyl-propionic acid 
• 93272-23-2 (2S,3R)-3-(Dimethyl-phenyl-silanyl)-2-methyl-3-phenyl-propionic acid 
• 88726-28-7 (2R,3R)-2-Methyl-3-phenyl-3-tributylstannanyl-propionic acid 
• 88726-28-7 (2S,3R)-2-Methyl-3-phenyl-3-tributylstannanyl-propionic acid 
• 63103-81-1 (1RS,2SR)-1-phenyl-2-(diphenylphosphinoyl)propan-1-ol 
• 127649-10-9 2,2,2-trifluoroethyl ethanesulfonate 
• 100-52-7 benzaldehyde 
• 106445-90-3 Ethylidene-tri-o-tolyl-λ⁵-phosphane 
• 106445-89-0 Tris-(2,6-difluoro-phenyl)-ethylidene-λ⁵-phosphane 
• 128399-07-5 tris(2-methoxymethoxyphenyl)phosphonioethanide 
• 1530-32-1 ethyltriphenylphosphonium bromide 

Downstream Products

• 23355-97-7 1-phenylpropylene oxide 
• 4541-87-1 cis-1-phenylpropene oxide 
• 111558-85-1 erythro-1-tert-butoxy-1-phenyl-2-chloropropane 
• 111558-86-2 threo-1-tert-butoxy-1-phenyl-2-chloropropane 
• 111558-87-3 erythro-1-tert-butoxy-1-phenyl-2-bromopropane 
• 111558-88-4 threo-1-tert-butoxy-1-phenyl-2-bromopropane 
• 111558-79-3 threo-1-tert-butoxy-1-phenyl-2-iodopropane 
• 873-66-5 1-propenylbenzene 
• 92387-04-7 2-(p-methoxyphenylsulfonyl)-1-phenylpropene 
• 56895-69-3 (cis-2,2-Dichloro-3-methylcyclopropyl)benzene 
• 124315-40-8 4,5-Diazafluorene-9-spiro-1'-(trans-2'-methyl-3'-phenyl)cyclopropane 
• 90299-47-1 5,5'-hydrazine-1,2-diylidene-bis(5H-pyrido[3',2':4,5]cyclopenta[1,2-b]pyridine) 

Relevant articles and documents

Characterization of water/sucrose laurate/n-propanol/ allylbenzene microemulsions

Water/n-propanol/sucrose laurate/allylbenzene micellar systems were formulated and applied in the isomerization of allylbenzene in the presence of heterogenized derivatives of some platinum group catalysts. The ratio (w/w) of n-propanol/surfactant studied herewith was 2/1. Temperature insensitive microemulsions were found. The microemulsions were characterized by the volumetric parameters, density, excess volume, ultrasonic velocity, and isentropic compressibility. The densities increase with increases in the water volume fraction. Excess volumes of the microemulsions decrease for water volume fractions below 0.2, level off for water volume fractions between 0.2 and 0.6 then increase for water volume fractions above 0.6. Excess volumes of the studied micellar systems increase with temperature. Isentropic compressibilities increase with temperature for water volume fractions below 0.8 and decrease for water volume fractions above 0.8. Structural transitions from water-in-oil to bicontinuous to oil-in-water occur along the microemulsion phase. The particle hydrodynamic diameter of the oil-in-water microemulsions at the 0.95 water volume fraction was found to decrease with temperature. AOCS 2012.

Small molecule activation by mixed methyl/methylidene rare earth metal complexes

Diverse reactivity patterns of mixed tetramethyl/methylidene rare-earth complexes bearing bulky benzamidinate coligands L3Ln3(μ2-Me)3(μ3-Me)(μ3-CH2) [L = [PhC(NC6H3iPr2-2,6)2]-; Ln = Y(1a), Lu(1b)] with PhCN, alkynes, and CS2 have been established. Reaction of complexes 1 with PhCN gave the μ3-CH2 addition complexes (NCNdipp)3Lu3(μ2-Me)3(μ3-Me)[μ-η1:η1:η3-CH2C(Ph)N] [Ln = Y(2a), Lu(2b)]. Treatment of complexes 1 with phenylacetylene afforded unexpected alkenyl dianion complexes L3Ln3(μ2-Me)3(μ3-Me)(μ-η1:η3-PhC≡CMe) [Ln = Y(3a), Lu(3b)] through the insertion of rare earth methylidene into a C-H bond in a reductive fashion. However, reaction of complexes 1 and HC≡CSiMe3 gave μ3-Me protonolysis complexes L3Ln3(μ2-Me)3(μ3-C≡CSiMe3)(μ3-CH2) [Ln = Y (4a), Lu (4b)] in excellent yields. Treatment of complexes 1 with CS2 led to the formation of the methyl activation complexes L3Ln3(μ2-Me)2(μ3-CH2)(μ3-η1:η2:η2-S2C≡CH2) [Ln = Y(5a), Lu(5b)]. All the new complexes were fully characterized.

Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton containing group 14 and 15 elements with benzaldehyde

Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton containing Group 14 and 15 elements (PhSi, PhGe, PhSn, n-BuSn, P, As, Sb, and Bi) at another bridgehead position with benzaldehyde provided (Z)-olefins as a major product in the cases of period 3 elements (PhSi, P) and (E)-olefins as a major product in the cases of below period 4 elements (PhGe, PhSn, n-BuSn, As, Sb, and Bi). These results are attributed to stereochemical drift of the intermediates come from the heteroatom effect at another bridgehead position of the phosphaheteratriptycene skeleton.

The phenylcarbene rearrangement as a source of real carbenes

The phenylcarbene rearrangement is used to produce carbenes that are compared to the intermediates formed on photolysis and pyrolysis of diazo compounds.

Singlet-state cis-trans photoisomerization of 1-phenylpropene

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FACILE PHOTOGENERATION OF COORDINATIVELY UNSATURATED ACTIVE SPECIES FROM HYDRIDOPHOSPHONITECOBALT(I) COMPLEX AND ITS APPLICATION TO DOUBLE-BOND MIGRATION OF OLEFIN

Pyrex-filtered irradiation of thermally inert complex 4> dissociated PPh(OMe)2 from cobalt without cleavage of a hydrido-cobalt bond, yielding an active species "CoH3".The photogenerated species caused double-bond migration of 3-phenylpropene to (E)- and (Z)-1-phenylpropenes.

Heteroatom effects toward isomerization of intermediates in Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton with benzaldehyde

Isomerization of intermediates, cis- and trans-1,2-oxaphosphetanes, in Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton containing group 14 (PhSi, PhGe, PhSn, n-BuSn) and 15 (P, As, Sb, and Bi) elements with benzaldehyde (PhCHO) was investigated by variable-temperature (VT)31P{1H} NMR spectroscopy. The isomerization from the cis-1,2-oxaphosphetane to the trans-form occurred at lower temperatures as the row number of the same group elements increases. Wittig reactions under the same conditions gave the (Z)-olefin as a major product in the cases of period 3 elements (PhSi and P) and the (E)-olefin as a major product in the cases of elements from period 4 and below (PhGe, PhSn, n-BuSn, As, Sb, and Bi). The selectivity of olefin formation is considered to depend on the isomerization temperature of the intermediates, because each olefin must be obtained from the corresponding 1,2-oxaphosphetane. The VT-31P{1H} NMR spectra showed that the cis-1,2-oxaphosphetanes were the kinetic products in the first step of Wittig reactions and the trans-forms were the thermodynamically stable products formed by isomerization from the cis-forms via ring-opening and ring-closing reactions of phosphonium ylides with PhCHO. Density functional theory (DFT) calculations indicated that cis-1,2-oxaphosphetanes were less stable than the trans-forms by ~2?kcal/mol, supporting thermodynamically favorable isomerization from cis-forms to trans-forms, as observed by VT-31P{1H} NMR spectroscopy. Heteroatoms at the bridgehead position of the phosphaheteratriptycene skeleton significantly affected the isomerization temperature as well as the phosphorus-31 signals in the 31P{1H} NMR spectra, which were observed at lower field as row number of the same group element increases.

RELATIVE THERMODYNAMIC STABILITIES OF THE ISOMERIC PROPENYLBENZENES

The relative thermodynamic stabilities of 2-propenylbenzene (allylbenzene), and the E and Z forms of 1-propenylbenzene were determined over the temperature range 50-170 deg C by chemical equilibration in DMSO solution with t-BuOK as catalyst.The values of the thermodynamic parameters ΔG, ΔH and ΔS at 298.15 K for each isomerization reaction between the title compounds were evaluated.

Norrish type II reactions of acyl azolium salts

The photochemical reactivity of acyl azolium salts derived from aliphatic carboxylic acids has been investigated. These species, which serve as models for intermediates generated in N-heterocyclic carbene (NHC) organocatalysis, undergo Norrish type II elimination reactions under irradiation with UVA light in analogy to structurally related aromatic ketones. Moreover, efficient Norrish-Yang cyclization was observed from an adamantyl-substituted derivative. These results further demonstrate the ability of NHCs to influence the absorption properties and photochemical reactivity of carbonyl groups during a catalytic cycle.

Illuminatinganti-hydrozirconation: controlled geometric isomerization of an organometallic species

A general strategy to enable the formalanti-hydrozirconation of arylacetylenes is reported that mergescis-hydrometallation using the Schwartz Reagent (Cp2ZrHCl) with a subsequent light-mediated geometric isomerization atλ= 400 nm. Mechanistic delineation of thecontra-thermodynamic isomerization step indicates that a minor reaction product functions as an efficientin situgenerated photocatalyst. Coupling of theE-vinyl zirconium species with an alkyne unit generates a conjugated diene: this has been leveraged as a selective energy transfer catalyst to enableE→Zisomerization of an organometallic species. Through anUmpolungmetal-halogen exchange process (Cl, Br, I), synthetically useful vinyl halides can be generated (up toZ?:?E= 90?:?10). This enabling platform provides a strategy to access nucleophilic and electrophilic alkene fragments in both geometric forms from simple arylacetylenes.