4-Chlorostyrene

4-Chlorostyrene Basic information
Product Name:4-Chlorostyrene
Synonyms:CHLOROSTYRENE-4;4-CHLOROSTYRENE , STABILIZED WITH 0.1% 4-TERT-BUTYLCATECHOL;4-CHLOROSTYRENE Stabilised with 0.1% 4-tert-butylcatechol;p-chloro-styren;Styrene, p-chloro-;styrene,p-chloro-;4-CHLOROSTYRENE;4-VINYLCHLOROBENZENE
CAS:1073-67-2
MF:C8H7Cl
MW:138.59
EINECS:214-028-8
Product Categories:Styrenes;Monomers;Polymer Science;Styrene and Functionalized Styrene Monomers
Mol File:1073-67-2.mol
4-Chlorostyrene Structure
4-Chlorostyrene Chemical Properties
Melting point -16 °C
Boiling point 192 °C(lit.)
density 1.155 g/mL at 25 °C(lit.)
vapor pressure 0.68 mm Hg ( 20 °C)
refractive index n20/D 1.565(lit.)
Fp 140 °F
storage temp. 2-8°C
form Liquid
Specific Gravity1.155
color Clear colorless to slightly yellow
Water Solubility Immiscible with water.
BRN 1098859
CAS DataBase Reference1073-67-2(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-chloro-4-ethenyl-(1073-67-2)
EPA Substance Registry SystemBenzene, 1-chloro-4-ethenyl- (1073-67-2)
Safety Information
Hazard Codes Xi,F
Risk Statements 36/37/38
Safety Statements 23-24/25-37/39-26-36
RIDADR 1993
WGK Germany 3
RTECS CZ0533000
TSCA T
HazardClass 3
PackingGroup III
HS Code 29036990
Hazardous Substances Data1073-67-2(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 5200 mg/kg
MSDS Information
ProviderLanguage
p-ChlorostyreneEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
4-Chlorostyrene Usage And Synthesis
Chemical Propertiesclear colourless to slightly yellow liquid. The side chain of p-chlorostyrene is a C=C double bond, so its chemical properties are more active. The compound can polymerize slowly at room temperature, and a polymerization inhibitor (stabilizer) can be added for storage.
Uses4-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.
Uses4-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.
PreparationSynthesis of 4-chlorostyrene: carry out catalytic dehydration reaction by 4-chlorophenethylalcohol at 280°C, the used catalyst is a modified aluminum silicate catalyst, and the yield is 80%.
Synthesis Reference(s)p-Chlorostyrene is commercially produced as a monomer from p-chloroethylbenzene by an oxidation technique. It is also produced as a mixture with o-chlorostyrene.
Journal of the American Chemical Society, 69, p. 852, 1947 DOI: 10.1021/ja01196a033
Tetrahedron Letters, 31, p. 5061, 1990 DOI: 10.1016/S0040-4039(00)97806-7
General Description4-Chlorostyrene is a para-halogenated styrene derivative. It undergoes graft copolymerization with acrylonitrile (AN) onto ethylene-propylene-diene terpolymer (EPDM) in the presence of benzoyl peroxide (initiator).
4-Chlorostyrene Preparation Products And Raw materials
Raw materials3-Buten-2-one, 4-(4-chlorophenyl)-, (3E)-–>2-(4-CHLOROPHENYL)OXIRANE–>1-CHLORO-4-(1,2-DIBROMOETHYL)BENZENE–>4-Chlorocinnamic acid–>4-Chlorobenzyl bromide–>4-Chlorobenzyl chloride–>Benzeneethanesulfonylazide, 4-chloro-–>6-Chloroindole–>5H-Cyclopenta[b]pyridine, 4-chloro-6,7-dihydro-–>6-CHLORO-2,3-DIHYDRO-1H-INDOLE
Preparation Products3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethyl cyclopropane carboxylic acid–>4-Chlorophenethylamine–>DIPHENYL(P-VINYLPHENYL)PHOSPHINE–>P-TRIMETHYLSILYL STYRENE–>3-(4-Chlorophenyl)propan-1-ol

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