16939-57-4

Basic information

• Product Name: 1-PHENYL-1,3-BUTADIENE
• Synonyms: 1-PHENYL-1,3-BUTADIENE;1-Phenyl-1,3-butadiene(E);Benzene, 1,3-butadienyl-, (E)-;trans-1-Phenyl-1,3-butadiene;[(E)-1,3-Butadienyl]benzene;(E)-BUTA-1,3-DIENYL BENZENE;(1E)-1-Phenyl-1,3-butadiene;trans-1-Phenylbutadiene
• CAS NO: 16939-57-4
• Molecular Formula: C₁₀H₁₀
• Molecular Weight: 130.19
• Product Categories: Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 16939-57-4.mol

Chemical Properties

• Melting Point: 2.3°C
• Boiling Point: 96℃ (18 Torr)
• Flash Point: 55°C
• Appearance: /
• Density: 0.9286
• Vapor Pressure: 0.355mmHg at 25°C
• Refractive Index: 1.65044 (20℃)
• Storage Temp.: ?20°C
• BRN: 1901458
• CAS DataBase Reference: 1-PHENYL-1,3-BUTADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-1,3-BUTADIENE(16939-57-4)
• EPA Substance Registry System: 1-PHENYL-1,3-BUTADIENE(16939-57-4)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20-36/38
• Safety Statements: 26
• RIDADR: UN 1993C 3 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 16939-57-4(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Resin Production:
1-Phenyl-1,3-butadiene is used as a monomer in the polymer industry for the production of various polymers and resins. Its unique structure allows for the creation of polymers with specific properties, such as enhanced strength, flexibility, and durability.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-Phenyl-1,3-butadiene is employed as a reactant in the synthesis of various pharmaceutical compounds. Its reactivity and versatility enable the development of new drugs with improved therapeutic effects and reduced side effects.
Used in Agricultural Chemical Production:
1-Phenyl-1,3-butadiene is also utilized in the agricultural sector as a reactant in the synthesis of agricultural chemicals. Its incorporation into these products can enhance their effectiveness in pest control and crop protection, contributing to increased agricultural productivity.

InChI:InChI=1/C10H10/c1-2-3-7-10-8-5-4-6-9-10/h2-9H,1H2/b7-3+

Upstream product

• 61752-38-3 (4E)-3-hydroxy-5-phenylpent-4-enoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 19493-09-5 Methylenetriphenylphosphorane 
• 591-50-4 iodobenzene 
• 71504-26-2 (E)-1-(trimethylsilyl)buta-1,3-diene 
• 42599-24-6 E-styryl iodide 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 97112-42-0 1-phenyl-1,2,3,4-tetrabromobutane 
• 85125-31-1 threo-1-phenyl-2-(trimethylsilyl)-3-buten-1-ol 
• 68724-63-0 (1S,2R)-1-Phenyl-2-trimethylsilanyl-but-3-en-1-ol 
• 88086-59-3 1-chloro-3-iodoprop-1(Z)-ene 
• 100-52-7 benzaldehyde 
• 88086-63-9 1-bromo-3-iodoprop-1-ene 
• 4141-48-4 allyldiphenylphosphine oxide 

Downstream Products

• 102754-35-8 1,2-dibenzoyl-3-phenyl-1,2,3,6-tetrahydro-pyridazine 
• 107620-57-5 (+/-)-1-methyl-2t-phenyl-cyclohex-3-ene-r-carboxylic acid 
• 107620-57-5 (+/-)-1-methyl-2c-phenyl-cyclohex-3-ene-r-carboxylic acid 
• 39677-54-8 3-phenyl-3,6-dihydro-pyridazine-1,2-dicarboxylic acid diethyl ester 
• 16605-99-5 biphenyl-2-carboxylic acid methyl ester 
• 16606-00-1 methyl 3-phenylbenzoate 
• 75025-13-7 methyl 2-phenyl-3-cyclohexenecarboxylate 
• 75025-14-8 methyl 5-phenyl-3-cyclohexenecarboxylate 
• 192884-89-2 dimethyl 3-phenylcyclohexa-1,4-diene-1,2-dicarboxylate 
• 341-44-6 2-phenyl-6-trifluoromethyl-cyclohex-3-enecarboxylic acid 
• 202589-95-5 (1S,2S)-1-phenyl-but-3-ene-1,2-diol 
• 145376-17-6 (1R,2R)-1-phenyl-but-3-ene-1,2-diol 
• 209864-30-2 (2R,3E)-4-phenylbut-3-ene-1,2-diol 

Relevant articles and documents

A convenient method for the synthesis of terminal (E)-1,3-dienes

Lithiated allylic phosphonates undergo efficient olefination reactions with a variety of aldehydes in the presence of HMPA to give terminal 1,3-dienes with high selectivity for the E-isomer. This method is general and procedurally simple.

Palladium-catalyzed inter- and intramolecular hydroamination of methylenecyclopropanes with amines

The inter- and intramolecular addition of nitrogen pronucleophiles to methylenecyclopropanes proceeds smoothly in the presence of palladium catalyst, giving the corresponding hydroamination products in good to excellent yields. The reaction proceeds mainl

Catalyst Controlled Regiodivergent Arylboration of Dienes

A method for the regiodivergent arylboration of dienes is presented. These reactions allow for the formation of a diverse range of synthetically versatile products from simple precursors. Through mechanistic studies, these reactions likely operate by init

Enantioselective Addition of Pyrazoles to Dienes**

We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd0-catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.

A STEREO- AND REGIO-SPECIFIC ADDITION OF ν3-TRIMETHYLSILYLALLYLTITANIUM COMPOUND WITH ALDEHYDES. A FACILE AND STEREOCONTROLLED SYNTHESIS OF E- AND Z-TERMINAL DIENES

ν3-Trimethylsilylallyltitanium compound, (ν5-C5H5)2Ti(ν3-1-trimethylsilylallyl), reacts with aldehydes to give (+/-)-(R,S)-3-trimethylsilyl-4-hydroxy-1-alkenes in excellent yields, which can be deoxysilylated to either E- or Z-1,3-dienes.

Tandem Cyclopropanation/Vinylogous Cloke-Wilson Rearrangement for the Synthesis of Heterocyclic Scaffolds

Cyclopropanation of 1,3-dienes with ethyl 2-formyldiazoacetate under rhodium catalysis results in either a tandem cyclopropanation/Cloke-Wilson rearrangement or a vinylogous variant, depending on the diene used. These adducts may be subjected to an oxygen

Copolymerization of 1,3-butadiene with phenyl/phenethyl substituted 1,3-butadienes: a direct strategy to access pendant phenyl functionalized polydienes

Copolymerization of 1,3-butadiene with various types of phenyl substituted 1,3-butadiene derivatives, including (E)-1-phenyl-1,3-butadiene (PBD), 1-phenethyl-1,3-butadiene (PEBD), 1-(4-methoxylphenyl)-1,3-butadiene (p-MEPBD), 1-(2-methoxylphenyl)-1,3-buta

Synthesis and heck reactions of ethenyl- and (Z)-butadien-1-yl nonaflate obtained by the fragmentation of furan derivatives

The nonaflation of lithium enolates or of silyl enol ethers, formally derived from acetaldehyde or crotonaldehyde, with nonafluorobutanesulfonyl fluoride gave ethenyl nonaflate (1b) and (Z)-buta-1,3-dien-1-yl nonaflate (2) in good yields. The required enolates were obtained by aldehyde-free routes by the lithiation of tetrahydrofuran or 2,5-dihydrofuran followed by the cyclofragmentation of the metallated heterocycles. The application of this approach to the synthesis of allenyl nonaflate 3 failed, presumably due to the intrinsic instability of this allene derivative. The nonaflates 1b and 2 were also prepared by the fluoride-catalysed reaction of the corresponding silyl enol ethers 5 and 7 with nonafluorobutanesulfonyl fluoride; however, the overall yields are slightly lower for these two-step pathways. The cyclofragmentation of lithiated 2,2-dimethyl-4-methylene-[1,3]dioxolane allowed the easy preparation of trimethylsiloxyallene (10) in moderate yield. The nonaflates 1b and 2 reacted smoothly with monosubstituted alkenes in the presence of a catalytic amount of palladium(II) acetate to give the anticipated Heck coupling products in good to moderate yields and with high stereoselectivities.

Stereoselective and Atom-Economic Alkenyl C-H Allylation/Alkenylation in Aqueous Media by Iridium Catalysis

A practical and atom-economic protocol for the stereoselective preparation of various 1,4-and 1,3-diene skeletons through iridium-catalyzed directed olefinic C-H allylation and alkenylation of NH-Ts acrylamides in water was developed. This reaction tolerated a wide scope of substrates under simple reaction conditions and enabled successful gram-scale preparation. Furthermore, an asymmetric variant of this reaction giving enantioenriched 1,4-dienes was achieved employing a chiral diene-iridium complex as the catalyst.

A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission

Substituted 1,3-dienes are valuable synthetic intermediates used in myriad catalytic transformations, yet modern catalytic methods for their preparation in a highly modular fashion using simple precursors are relatively few. We report here an aerobic boron Heck reaction with cyclobutene that forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic acids, rather than typical Heck products (i.e., substituted cyclobutenes). Experimental and computational mechanistic data support a pericyclic mechanism for C-C bond cleavage that enables the cycloalkene to circumvent established limitations associated with diene reagents in Heck-type reactions.