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Cas Database

16939-57-4

16939-57-4

Identification

  • Product Name:Benzene,(1E)-1,3-butadienyl-

  • CAS Number: 16939-57-4

  • EINECS:

  • Molecular Weight:130.189

  • Molecular Formula: C10H10

  • HS Code:

  • Mol File:16939-57-4.mol

Synonyms:1,3-Butadiene,1-phenyl-, (E)- (8CI); Benzene, 1,3-butadienyl-, (E)-;(1E)-1-Phenyl-1,3-butadiene; (E)-1,3-Butadienylbenzene; (E)-1-Phenyl-1,3-butadiene;(E)-1-Phenyl-1,3-butadiene; [(1E)-1,3-Butadienyl]benzene;trans-1-Phenyl-1,3-butadiene; trans-1-Phenylbutadiene; trans-b-Vinylstyrene

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Safety information and MSDS view more

  • Pictogram(s):Xn

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H319 Causes serious eye irritation H331 Toxic if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:(E)-Buta-1,3-dienylBenzene
  • Packaging:50mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:(E)-Buta-1,3-dienylBenzene
  • Packaging:100mg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:trans-1-Phenyl-1,3-butadiene ≥95.0% (HPLC)
  • Packaging:1g
  • Price:$ 164
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  • Manufacture/Brand:Ambeed
  • Product Description:(E)-Buta-1,3-dien-1-ylbenzene 95%
  • Packaging:5g
  • Price:$ 666
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  • Manufacture/Brand:Ambeed
  • Product Description:(E)-Buta-1,3-dien-1-ylbenzene 95%
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  • Manufacture/Brand:Ambeed
  • Product Description:(E)-Buta-1,3-dien-1-ylbenzene 95%
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  • Manufacture/Brand:Ambeed
  • Product Description:(E)-Buta-1,3-dien-1-ylbenzene 95%
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Relevant articles and documentsAll total 194 Articles be found

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

Wang,West

, p. 99 - 103 (2002)

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

Nakamura,Itagaki,Yamamoto

, p. 1532 - 1540 (2001)

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

Sardini, Stephen R.,Brown, M. Kevin

, p. 9823 - 9826 (2017)

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**

Dong, Vy M.,Jiu, Alexander Y.,Slocumb, Hannah S.,Yang, Xiao-Hui,Yeung, Charles S.

, p. 19660 - 19664 (2021)

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

Sato, Fumie,Suzuki, Yoshito,Sato, Masao

, p. 4589 - 4592 (1982)

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

Piotrowski, Mathew L.,Kerr, Michael A.

, p. 7624 - 7627 (2018)

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

Li, Dexin,Lin, Juan,Liu, Heng,Wang, Feng,Zhang, Chunyu,Zhang, Xuequan

, p. 23184 - 23191 (2021)

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

-

Block,E.,Aslam,M.

, p. 6165 (1983)

-

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

Lyapkalo, Ilya M.,Webel, Matthias,Reissig, Hans-Ulrich

, p. 4189 - 4194 (2001)

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

Ding, Liyuan,Huang, Yinhua,Lu, Xiunan,Shen, Wenzhou,Xu, Liangyao,Yu, Feifei,Zhang, Jian,Zhong, Guofu,Zhong, Liangjun

, p. 7225 - 7237 (2020)

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

McAlpine, Neil J.,Wang, Long,Carrow, Brad P.

, p. 13634 - 13639 (2018)

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.

A Practical Synthesis of 1,3-Diene Using Allyltriphenylsilane and Titanium Tetraisopropoxide

Ikeda, Yoshihiko,Yamamoto, Hisashi

, p. 657 - 658 (1986)

A practical method for the stereoselective preparation of 1,3-dienes by the use of allyltriphenylsilane as a key reagent is described.

Dynamic kinetic resolution of acyclic allylic acetates using lipase and palladium

Choi, Yoon Kyung,Suh, Jong Hwa,Lee, Donghyun,Lim, In Taek,Jung, Jae Yoon,Kim, Mahn-Joo

, p. 8423 - 8424 (1999)

-

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

Tran, Hai N.,Stanley, Levi M.

supporting information, p. 395 - 399 (2021/12/27)

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides

Wang, Chengdong,Guo, Yingjie,Wang, Xiaoming,Wang, Zheng,Ding, Kuiling

supporting information, p. 15903 - 15907 (2021/10/07)

An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,

Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji-Trost of Benzotriazoles with 1,3-Dienes

Li, Yin-Lin,Wu, Hai-Hong,Zhang, Junliang,Zhang, Pei-Chao

supporting information, p. 13010 - 13015 (2021/09/07)

The asymmetric denitrogenative cycloaddition has emerged as a powerful tool to build chiral aza-heterocyles. However, only one example of asymmetric denitrogenative cycloaddition of benzotriazole with unsaturated hydrocarbons has been explored so far, bec

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Jiang, Yimin,Shi, Zhaojiang,Wu, Jinnan,Wu, Shaofen,Ye, Keyin,Yu, Yi,Yuan, Yaofeng

supporting information, (2021/11/17)

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Process route upstream and downstream products

Process route

phenylium
17333-73-2

phenylium

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

1,4-dihydronaphthalene
612-17-9

1,4-dihydronaphthalene

3-Methylindene
767-60-2

3-Methylindene

Conditions
Conditions Yield
With oxygen; trimethylamine; under 30 Torr; Mechanism; Product distribution; also with 3H-labelled compound, nuclear decay of a tritium atom, further pressures, additives;
3%
3%
4%
9%
4%
trimethyl ((1E,3E)-4-phenylbuta-1,3-dien-1-yl)silane
70960-88-2

trimethyl ((1E,3E)-4-phenylbuta-1,3-dien-1-yl)silane

acetic anhydride
108-24-7

acetic anhydride

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

(E,E)-6-phenyl-3,5-hexadien-2-one
4173-44-8

(E,E)-6-phenyl-3,5-hexadien-2-one

Conditions
Conditions Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; In toluene; at 120 ℃; for 24h; Inert atmosphere;
4-allyl-2-phenyl-Δ<sup>2</sup>-1,3,4-oxadiazolin-5-one
55084-88-3

4-allyl-2-phenyl-Δ2-1,3,4-oxadiazolin-5-one

2-phenyl-1,3-butadiene
2288-18-8

2-phenyl-1,3-butadiene

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

1-phenylbut-3-en-1-one
6249-80-5

1-phenylbut-3-en-1-one

Conditions
Conditions Yield
at 700 ℃; under 0.01 Torr; flash vacuum pyrolysis;
5%
30%
25%
40%
at 700 ℃; under 0.01 Torr;
30%
25%
5%
40%
at 700 ℃; under 0.01 Torr; Flash vacuum pyrolysis;
40%
30%
25%
5%
allyltriphenylphosphonium bromide
1560-54-9

allyltriphenylphosphonium bromide

benzaldehyde
100-52-7

benzaldehyde

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

(Z)-1-Phenylbuta-1,3-diene
31915-94-3

(Z)-1-Phenylbuta-1,3-diene

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
Conditions Yield
With Carbowax 6000 (liquid); potassium carbonate; at 150 ℃; under 15 Torr; Yield given. Yields of byproduct given;
(E)-ethyl 1-phenylbut-2-enyl carbonate
1352656-24-6

(E)-ethyl 1-phenylbut-2-enyl carbonate

phenylboronic acid
98-80-6

phenylboronic acid

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

ethyl (E)-1-phenylbut-1-en-3-ol
36004-04-3

ethyl (E)-1-phenylbut-1-en-3-ol

Conditions
Conditions Yield
With water; palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 50 ℃; for 24h; stereoselective reaction;
82%
(S)-trans-4-phenyl-3-buten-2-ol
81176-43-4

(S)-trans-4-phenyl-3-buten-2-ol

phenylboronic acid
98-80-6

phenylboronic acid

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 80 ℃; for 36h; Inert atmosphere;
79%
(E)-tert-butyl (4-phenylbut-3-en-2-yl) carbonate

(E)-tert-butyl (4-phenylbut-3-en-2-yl) carbonate

phenylboronic acid
98-80-6

phenylboronic acid

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

ethyl (E)-1-phenylbut-1-en-3-ol
36004-04-3

ethyl (E)-1-phenylbut-1-en-3-ol

Conditions
Conditions Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; water; palladium diacetate; In tetrahydrofuran; at 50 ℃; for 24h; stereoselective reaction;
54%
(E)-tert-butyl (4-phenylbut-3-en-2-yl) carbonate

(E)-tert-butyl (4-phenylbut-3-en-2-yl) carbonate

phenylboronic acid
98-80-6

phenylboronic acid

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

Conditions
Conditions Yield
With water; palladium diacetate; tricyclohexylphosphine; In tetrahydrofuran; at 50 ℃; for 24h; stereoselective reaction;
20%
4-phenyl-3-butenyl para-toluenesulfonate
93652-37-0,7515-44-8

4-phenyl-3-butenyl para-toluenesulfonate

phenylboronic acid
98-80-6

phenylboronic acid

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

(E)-1,4-diphenylbut-1-ene
27066-35-9

(E)-1,4-diphenylbut-1-ene

Conditions
Conditions Yield
With dichloro bis(acetonitrile) palladium(II); tri-tert-butyl phosphine; 2-Methoxynaphthalene; caesium carbonate; In toluene; at 80 ℃; for 24h;
41%
With dichloro bis(acetonitrile) palladium(II); 2-Methoxynaphthalene; caesium carbonate; tri-p-tolylphosphite; In toluene; at 80 ℃; for 24h;
13%
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

phenylboronic acid
98-80-6

phenylboronic acid

(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; benzene; Reflux;
38%
14%

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