98-83-9

Basic information

• Product Name: 2-Phenyl-1 -propene
• Synonyms: Benzene,(1-methylethenyl)-
• CAS NO: 98-83-9
• Molecular Formula: C9H10
• Molecular Weight: 118.1757
• EINECS: 202-705-0
• Mol File: 98-83-9.mol

Chemical Properties

• Melting Point: -23℃
• Boiling Point: 162.5 °C at 760 mmHg
• Flash Point: 45.556 °C
• Appearance: clear to yellow liquid
• Density: 0.874 g/cm³
• Refractive Index: 1.537-1.539
• Water Solubility: insoluble
• CAS DataBase Reference: 2-Phenyl-1 -propene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-1 -propene(98-83-9)
• EPA Substance Registry System: 2-Phenyl-1 -propene(98-83-9)

Safety Data

• Hazard Codes: Xi:Irritant;; <
• Statements: R10:; R36/37:; R51/53:
• Safety Statements: S61:
• RIDADR: 2303
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 98-83-9(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
2-Phenyl-1-propene is used as a monomer in the production of polystyrene, a widely used plastic material known for its clarity, versatility, and resistance to water, chemicals, and impact. Polystyrene is favored for applications such as packaging materials, disposable cutlery, and insulation due to its lightweight and moldable properties.
Used in Synthesis of Rubber and Resins:
In the chemical industry, 2-Phenyl-1-propene serves as a critical component in the synthesis of synthetic rubbers and resins. These materials are utilized in a variety of applications, including automotive parts, adhesives, and coatings, due to their flexibility, durability, and resistance to various environmental conditions.
Used in Fiberglass Production:
2-Phenyl-1-propene is also utilized in the manufacturing process of fiberglass, a composite material that combines glass fibers with a resin matrix. Fiberglass is valued for its strength, lightweight, and corrosion resistance, making it suitable for applications in the aerospace, automotive, and construction industries.
Used in Research and Development:
In the scientific community, 2-Phenyl-1-propene is employed as a model compound in various research studies, particularly in the fields of polymer chemistry and material science. Its reactivity and structural properties make it an ideal candidate for understanding polymerization processes and developing new materials with enhanced properties.

InChI:InChI=1/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3

Upstream product

• 98-86-2 acetophenone 
• 19493-09-5 Methylenetriphenylphosphorane 
• 98-82-8 Isopropylbenzene 
• 253185-03-4 tert-butylbenzene 
• 591-50-4 iodobenzene 
• 72824-04-5 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane 
• 593-71-5 Chloroiodomethane 
• 509-14-8 tetranitromethane 
• 1889-67-4 dicumene 
• 873-49-4 cyclopropylbenzene 
• 80-15-9 Cumene hydroperoxide 
• 98-81-7 1-bromovinylbenzene 
• 917-54-4 methyllithium 
• 16917-35-4 (E)-(1-bromoprop-1-en-2-yl)benzene 

Downstream Products

• 37918-82-4 1-(3-phenylbut-3-en-1-yl)pyrrolidine 
• 109933-22-4 1-(3-phenylbut-3-en-1-yl)piperidine 
• 37918-84-6 4-(3-phenylbut-3-en-1-yl)morpholine 
• 874511-88-3 2,5-bis-(1-methyl-1-phenyl-ethyl)-thiophene 
• 64651-63-4 acetic acid-(1-methyl-4-phenyl-[4]piperidyl ester) 
• 13147-09-6 3-demethylprodine 
• 36122-28-8 ethyl 2-methyl-2-phenylcyclopropane-1-carboxylate 
• 4894-24-0 3,5-diphenyl-5-methyl-4,5-dihydroisoxazole 
• 102182-26-3 bis-(2-phenyl-propylmercapto)-[1,3,4]thiadiazole 
• 7306-12-9 1-acetoxy-3-phenyl-but-3-ene 
• 20883-16-3 1-acetoxy-3-phenylbut-2-ene 
• 7534-40-9 2-phenylallyl acetate 
• 64713-71-9 1,1,1-trichloro-4-phenyl-pent-4-en-2-ol 
• 70738-48-6 phenyl 2-phenylpropyl sulfone 

Relevant articles and documents

Selective C(sp3)?N Bond Cleavage of N,N-Dialkyl Tertiary Amines with the Loss of a Large Alkyl Group via an SN1 Pathway

Polar disconnection of the C(sp3)?N bond of N,N-dialkyl-substituted tertiary amines via ammonium species conventionally favored the loss of the smaller alkyl group by an SN2 displacement, while selective C(sp3)?N bond cleavage by cutting off the larger alkyl group is still underdeveloped. Herein, we present a novel Pd0-catalyzed [2+2+1] annulation, proceeding through an alkyne-directed palladacycle formation and consecutive diamination with a tertiary hydroxylamine by cleaving its N?O bond and one C(sp3)?N bond, for the rapid assembly of tricyclic indoles in a single-step transformation. Noteworthy, experimental results indicated that large tert-butyl and benzyl groups were selectively cleaved via an SN1 pathway, in the presence of a smaller alkyl group (Me, Et, iPr). Under the guidance of this new finding, tricyclic indoles bearing a removable alkyl group could be exclusively obtained by using a (α-methyl)benzyl/benzyl or tert-butyl/2-(methoxycarbonyl)ethyl mixed amino source.

Experimental and Computational Studies of Palladium-Catalyzed Spirocyclization via a Narasaka-Heck/C(sp3or sp2)-H Activation Cascade Reaction

The first synthesis of highly strained spirocyclobutane-pyrrolines via a palladium-catalyzed tandem Narasaka-Heck/C(sp3 or sp2)-H activation reaction is reported here. The key step in this transformation is the activation of a δ-C-H bond via an in situ generated σ-alkyl-Pd(II) species to form a five-membered spiro-palladacycle intermediate. The concerted metalation-deprotonation (CMD) process, rate-determining step, and energy barrier of the entire reaction were explored by density functional theory (DFT) calculations. Moreover, a series of control experiments was conducted to probe the rate-determining step and reversibility of the C(sp3)-H activation step.

Palladium-Aminopyridine Catalyzed C?H Oxygenation: Probing the Nature of Metal Based Oxidant

A mechanistic study of direct selective oxidation of benzylic C(sp3)?H groups with peracetic acid, catalyzed by palladium complexes with tripodal amino-tris(pyriylmethyl) ligands, is presented. The oxidation of arylalkanes having secondary and tertiary benzylic C?H groups, predominantly yields, depending on the substrate and conditions, either the corresponding ketones or alcohols. One of the three 2-pyriylmethyl moieties, which is pending in the starting catalyst, apparently, facilitates the active species formation and takes part in stabilization of the high-valent Pd center in the active species, occupying the axial coordination site of palladium. The catalytic, as well as isotopic labeling experiments, in combination with ESI-MS data and DFT calculations, point out palladium oxyl species as possible catalytically active sites, operating essentially via C?H abstraction/oxygen rebound pathway. For the ketones formation, O?H abstraction/в-scission mechanism has been proposed.

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes

Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

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.

Enantioselective Hydrothiolation: Diverging Cyclopropenes through Ligand Control

In this article, we advance Rh-catalyzed hydrothiolation through the divergent reactivity of cyclopropenes. Cyclopropenes undergo hydrothiolation to provide cyclopropyl sulfides or allylic sulfides. The choice of bisphosphine ligand dictates whether the pathway involves ring-retention or ring-opening. Mechanistic studies reveal the origin for this switchable selectivity. Our results suggest the two pathways share a common cyclopropyl-Rh(III) intermediate. Electron-rich Josiphos ligands promote direct reductive elimination from this intermediate to afford cyclopropyl sulfides in high enantio- A nd diastereoselectivities. Alternatively, atropisomeric ligands (such as DTBM-BINAP) enable ring-opening from the cyclopropyl-Rh(III) intermediate to generate allylic sulfides with high enantio- A nd regiocontrol.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.