4-Chlorostyrene

Base Information

• Chemical Name: 4-Chlorostyrene
• CAS No.: 1073-67-2
• Molecular Formula: C8H7Cl
• Molecular Weight: 138.597
• Hs Code.: 29036990
• European Community (EC) Number: 214-028-8
• NSC Number: 18603
• UNII: T0J05U220F
• DSSTox Substance ID: DTXSID4061464
• Nikkaji Number: J2.125C
• Wikidata: Q27289507
• Mol file: 1073-67-2.mol

Synonyms:4-chlorostyrene;p-chlorostyrene

Chemical Property of 4-Chlorostyrene

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 0.68 mm Hg ( 20 °C)
• Melting Point: -16 °C
• Refractive Index: n20/D 1.565(lit.)
• Boiling Point: 192.688 °C at 760 mmHg
• Flash Point: 61.196 °C
• PSA: 0.00000
• Density: 1.088 g/cm³
• LogP: 2.98300
• Storage Temp.: 2-8°C
• Water Solubility.: Immiscible with water.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 138.0236279
• Heavy Atom Count: 9
• Complexity: 90.7

Purity/Quality:

99% ^*data from raw suppliers

4-Chlorostyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Styrenes
• Canonical SMILES: C=CC1=CC=C(C=C1)Cl
• Uses: 4-Chlorostyrene is used in the preparation of new bis(pyrazolyl)borato olefin complexes of copper(I). It is also employed in the investigation of regioselectivity in the cationic Heck reaction of 4-substituted styrenes. Further, it plays an important role in the preparation of 4-[(4-chloro-phenyl)-thioacetyl]-morpholine. 4-Chlorostyrene was used in the following studies:Study of chemical and biochemical properties of the vinyl group of styrene by the development of structure activity relationships (SAR).Preparation of new bis(pyrazolyl)borato olefin complexes of copper(I).To investigate the regioselectivity in the cationic Heck reaction of 4-substituted styrenes.

Technology Process of 4-Chlorostyrene

There total 115 articles about 4-Chlorostyrene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-Chlorostyrene oxide (2788-86-5) → 4-vinylbenzyl chloride (1073-67-2,24991-47-7)

Guidance literature:

With sodium iodide; tin(ll) chloride; In ethanol; for 0.0666667h; Reflux; Green chemistry;

DOI:10.1055/s-0034-1378821

Reference yield: 79.0%

bromochlorobenzene (106-39-8) + Vinyl bromide (593-60-2,25951-54-6) → 4-vinylbenzyl chloride (1073-67-2,24991-47-7)

Guidance literature:

With palladium diacetate; C₂₂H₂₇P; triethylamine; In 1,4-dioxane; Hexadecane; at 120 ℃; for 20h; under 15001.5 Torr; Schlenk technique; Inert atmosphere;

DOI:10.3390/molecules25153421

Reference yield: 62.6%

4-chloro-β-phenethylsulfonyl azide (54664-52-7) → 4-vinylbenzyl chloride (1073-67-2,24991-47-7) + 6-chloroindole (17422-33-2) + 6-chloroindoline (52537-00-5) + 4-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (54664-55-0)

Guidance literature:

at 650 ℃; for 0.26h; Product distribution;

DOI:10.1021/ja00396a039

upstream raw materials:

ethanol

sodium ethanolate

(4-chloro-phenethyl)-dimethyl sulfonium ; bromide

3-(4-chlorophenyl)prop-2-enoic acid

Downstream raw materials:

1-(1-bromo-3,3,3-trichloro-propyl)-4-chloro-benzene

1,2-dibromo-1-(4-chlorophenyl)ethane

4-(trimethylsilyl)styrene

para-chloroacetophenone

Refernces

• 1、 Seitz, David E.,Zapata, Antonio. "(TRIMETHYLSILYLMETHYL)TRIBUTYLTIN: A CONVENIENT IN SITU PRECURSOR OF TRIMETHYLSILYLMETHYLLITHIUM". . p. 3451 - 3454. Retrieved 1980.
• 2、 Kanoh et al.. "". . p. 106,107,109,112. Retrieved 1963.
• 3、 Ando, Kaori,Kobayashi, Takahisa,Uchida, Nariaki. "Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents". . p. 2554 - 2557. Retrieved 2015.
• 4、 Lau, Kelvin Chi Yin,Chiu, Pauline. "The application of non-cross-linked polystyrene-supported triphenylarsine in Stille coupling reactions". . p. 1813 - 1816. Retrieved 2007.
• 5、 Ando, Kaori,Oguchi, Mai,Kobayashi, Takahisa,Asano, Haruka,Uchida, Nariaki. "Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone". . p. 9936 - 9943. Retrieved 2020.
• 6、 Brooks. "-". . p. 1295,1297. Retrieved 1944.
• 7、 Marvel,Schertz. "-". . p. 2054,2056. Retrieved 1943.
• 8、 Lando, Vanusa R.,Monteiro, Adriano L.. "Simple and efficient protocol for the synthesis of functionalized styrenes from 1,2-dibromoethane and arylboronic acids". . p. 2891 - 2894. Retrieved 2003.
• 9、 Lee, Yeong Jin,Shin, Jeong Won,Yoo, Byung Woo. "Mild and efficient desulfurization of thiiranes with MoCl5/Zn system". . . Retrieved 2021/11/10.
• 10、 Dong, Bingbing,Lu, Jiansha,Bao, Honghao,Zhang, Yuanyuan,Liu, Yingguo,Leng, Yuting. "Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides". supporting information. p. 3769 - 3776. Retrieved 2021/07/14.