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  • 4-Vinylbenzyl chloride 1592-20-7 Factory PRICE IN STOCK 4-(Chloromethyl)styrene COA CAS 1592-20-7

    Cas No: 1592-20-7

  • USD $ 3.5-5.0 / Kiloliter

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  • 1592-20-7 Structure
  • Basic information

    1. Product Name: 4-Vinylbenzyl chloride
    2. Synonyms: 1-(chloromethyl)-4-ethenyl-benzen;1-(chloromethyl)-4-ethenyl-Benzene;4-(CHLOROMETHYL)STYRENE;4-VINYLBENZYL CHLORIDE;1-(chloromethyl)-4-vinylbenzene;4-VINYLBENZYL CHLORIDE, STAB.;4-Vinylbenylchloride;4-Vinylbenzyl chloride, tech., 90%
    3. CAS NO:1592-20-7
    4. Molecular Formula: C9H9Cl
    5. Molecular Weight: 152.62
    6. EINECS: 250-005-9
    7. Product Categories: Intermediates of Dyes and Pigments;Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Chloromethy styrene
    8. Mol File: 1592-20-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 229 °C(lit.)
    3. Flash Point: 221 °F
    4. Appearance: Clear yellow/Liquid
    5. Density: 1.083 g/mL at 25 °C(lit.)
    6. Vapor Density: 5.3 (vs air)
    7. Vapor Pressure: 1 mm Hg ( 56.1 °C)
    8. Refractive Index: n20/D 1.572(lit.)
    9. Storage Temp.: −20°C
    10. Solubility: N/A
    11. Water Solubility: Insoluble in water
    12. BRN: 2204384
    13. CAS DataBase Reference: 4-Vinylbenzyl chloride(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Vinylbenzyl chloride(1592-20-7)
    15. EPA Substance Registry System: 4-Vinylbenzyl chloride(1592-20-7)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34-43-21/22
    3. Safety Statements: 26-36/37/39-45
    4. RIDADR: UN 3265 8/PG 3
    5. WGK Germany: 3
    6. RTECS:
    7. F: 8-19
    8. HazardClass: 8
    9. PackingGroup: III
    10. Hazardous Substances Data: 1592-20-7(Hazardous Substances Data)

1592-20-7 Usage

Chemical Properties

clear yellow liquid

Uses

Component of ion exchange resins, photo-resist polymers, cross-linkable fibers, coupling agents and electroconducting polymers.Starter for various copolymer preparations.Dual functional monomer. Readily derivatized by chloride displacement.

Purification Methods

Purify 4-vinylbenzyl chloride by dissolving it in Et2O, washing it with 0.5% of aqueous NaOH, separating, drying the organic layer (Na2SO4), evaporating and distilling the residual oil under N2 in vacuo. Add 0.05% of 4-tert-butylcatechol as stabilizer. It is lachrymatory. [Nishikubo et al. Tetrahedron Lett 22 3872 1981, Tanimoto et al. Synth Commun 4 193 1974, Beilstein 6 IV 3818.]

Check Digit Verification of cas no

The CAS Registry Mumber 1592-20-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,9 and 2 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1592-20:
(6*1)+(5*5)+(4*9)+(3*2)+(2*2)+(1*0)=77
77 % 10 = 7
So 1592-20-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H9Cl/c1-2-8-3-5-9(7-10)6-4-8/h2-6H,1,7H2

1592-20-7 Well-known Company Product Price

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  • CAS number
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  • Detail
  • Aldrich

  • (436887)  4-Vinylbenzylchloride  90%

  • 1592-20-7

  • 436887-25ML

  • 407.16CNY

  • Detail
  • Aldrich

  • (436887)  4-Vinylbenzylchloride  90%

  • 1592-20-7

  • 436887-100ML

  • 601.38CNY

  • Detail

1592-20-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Vinylbenzyl chloride

1.2 Other means of identification

Product number -
Other names 4-Vinylbenzyl Chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1592-20-7 SDS

1592-20-7Synthetic route

p-chloromethyl-α-bromoethylbenzene
35793-35-2

p-chloromethyl-α-bromoethylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With 18-crown-6 ether; potassium hydroxide In toluene at 40℃; for 4h; Reagent/catalyst; Temperature; Solvent;95%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; Tropone In dichloromethane at 20℃; for 0.25h; Inert atmosphere;84%
1-(2-chloroethyl)-4-(chloromethyl)benzene
53459-40-8

1-(2-chloroethyl)-4-(chloromethyl)benzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With 4-tert-Butylcatechol; sodium t-butanolate In tetrahydrofuran at 30℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere;83%
p-chloromethyl-2-bromoethylbenzene
24249-98-7

p-chloromethyl-2-bromoethylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide at 30℃; for 4h; different reagents, solvents and reaction times;77%
With tetrabutylammomium bromide; potassium hydroxide In tert-butyl alcohol at 30℃; for 4h;50.1%
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride In fluorobenzene; water at 20℃; Irradiation; Green chemistry;68%
poly 4-chlorostyrene

poly 4-chlorostyrene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
at 500 - 650℃;60%
styrene
292638-84-7

styrene

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With carbon disulfide; zinc(II) chloride at 40℃; for 5h; Reflux;13%
4-ethylbenzylchloride
1467-05-6

4-ethylbenzylchloride

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
(i) NBS, (PhCO)2O2, (ii) (heating), benzene-1,4-diol; Multistep reaction;
1-(4-chloromethylphenyl)ethanol
76297-21-7

1-(4-chloromethylphenyl)ethanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With potassium hydrogensulfate; 4-tert-Butylcatechol at 210℃;
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

A

α-chloro-p-methylstyrene
42107-37-9

α-chloro-p-methylstyrene

B

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

C

di- and trichlorinated products

di- and trichlorinated products

Conditions
ConditionsYield
With chlorine In water at 560℃; for 0.000222222h; Product distribution; gas phase reaction, oth. isomers;
4-chloromethylbenzaldehyde
73291-09-5

4-chloromethylbenzaldehyde

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: KHSO4, 4-tert-butyl-benzene-1,2-diol / 210 °C
View Scheme
4-chloromethylbenzaldehyde
73291-09-5

4-chloromethylbenzaldehyde

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 16h; Wittig Olefination;
ethylbenzene
100-41-4

ethylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bromine / 3 h / Reflux; Inert atmosphere
2: hydrogenchloride; zinc(II) chloride / 20 h / 40 °C / Reflux
3: potassium hydroxide; 18-crown-6 ether / toluene / 4 h / 40 °C
View Scheme
2-phenylethanol
60-12-8

2-phenylethanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen bromide; zinc(II) chloride / 6 h / 80 - 90 °C / Reflux
2: hydrogenchloride; zinc(II) chloride / 18 h / 30 °C / Reflux
3: tetrabutylammomium bromide; potassium hydroxide / tert-butyl alcohol / 4 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 8 h / 120 °C
2: hydrogenchloride; sulfuric acid; zinc(II) chloride / water / 5 h / 90 °C
3: sodium t-butanolate; 4-tert-Butylcatechol / tetrahydrofuran / 1 h / 30 °C / Inert atmosphere
View Scheme
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; zinc(II) chloride / 18 h / 30 °C / Reflux
2: tetrabutylammomium bromide; potassium hydroxide / tert-butyl alcohol / 4 h / 30 °C
View Scheme
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

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

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

Conditions
ConditionsYield
With Ph-HMS; bromine In dichloromethane for 5h; Ambient temperature; Irradiation;100%
With sodium periodate; acetic acid; lithium bromide at 25℃;96%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

2-bromo-1-(4-chloromethylphenyl)ethanol

2-bromo-1-(4-chloromethylphenyl)ethanol

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetonitrile at 20℃;100%
With sodium periodate; sulfuric acid; lithium bromide In water; acetonitrile at 25℃; pH=6.12;85%
With N-Bromosuccinimide; water In acetone at 0 - 20℃;
pyrrolidine
123-75-1

pyrrolidine

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

1-[(4-ethenylphenyl)methyl]-pyrrolidine
60472-54-0

1-[(4-ethenylphenyl)methyl]-pyrrolidine

Conditions
ConditionsYield
In hexane at 0 - 20℃;100%
In hexane at 20℃; for 20h; Cooling with ice;98%
In hexane at 0 - 20℃;
In hexane
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

dimethylamino-methanesulfonic acid ; sodium salt

dimethylamino-methanesulfonic acid ; sodium salt

4-vinylbenzyldimethylammonio methanesulfonate
1273544-34-5

4-vinylbenzyldimethylammonio methanesulfonate

Conditions
ConditionsYield
In ethanol; water at 45℃; for 24h; Inert atmosphere;100%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

trimethylamine
75-50-3

trimethylamine

N,N,N-trimethyl-1-(4-vinylphenyl)methanaminium chloride
7538-38-7

N,N,N-trimethyl-1-(4-vinylphenyl)methanaminium chloride

Conditions
ConditionsYield
In ethanol at 20℃; for 18h;100%
In water at 0℃; for 72h;
In N,N-dimethyl-formamide at 60℃; for 24h; Autoclave;
bis-(dimethylamino)methane
51-80-9

bis-(dimethylamino)methane

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

N,N'-(methylene)bis(N,N-dimethyl-1-(4-vinylphenyl)methanaminium) chloride

N,N'-(methylene)bis(N,N-dimethyl-1-(4-vinylphenyl)methanaminium) chloride

Conditions
ConditionsYield
In acetonitrile at 50℃; for 48h; Inert atmosphere;100%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

sodium acetate
127-09-3

sodium acetate

4-acetoxymethylstyrene
1592-12-7

4-acetoxymethylstyrene

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 48h; Heating;99%
In dimethyl sulfoxide at 50℃; for 47h;
In dimethyl sulfoxide at 45℃; for 24h; Inert atmosphere;
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

4-vinylbenzyl iodide
45817-37-6

4-vinylbenzyl iodide

Conditions
ConditionsYield
With sodium iodide In acetone for 20h; Inert atmosphere; Reflux;99%
With sodium iodide In acetonitrile for 12h; Inert atmosphere; Reflux;92%
With sodium iodide In butanone at 20℃; for 8h;91%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

triethylamine
121-44-8

triethylamine

triethyl-(4-vinylbenzyl)ammonium chloride
14350-43-7

triethyl-(4-vinylbenzyl)ammonium chloride

Conditions
ConditionsYield
In methanol at 30℃;99%
In acetonitrile at 40℃; for 93h;94%
With 2,6-di-tert-butyl-4-methyl-phenol at 50℃; for 48h; Inert atmosphere;
In N,N-dimethyl-formamide at 60℃; for 24h; Autoclave;
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

trioctyl(4-vinylbenzyl)phosphonium chloride

trioctyl(4-vinylbenzyl)phosphonium chloride

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 48h; Inert atmosphere;99%
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 48h; Inert atmosphere;
tributyl-amine
102-82-9

tributyl-amine

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

tri-n-butyl-(4-vinylbenzyl)ammonium chloride

tri-n-butyl-(4-vinylbenzyl)ammonium chloride

Conditions
ConditionsYield
In acetonitrile at 40℃; for 68h;99%
In dichloromethane at 20℃; for 48h;85%
In acetonitrile at 50℃; for 48h;82%
In acetonitrile at 40℃; for 24h; Inert atmosphere;80%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

C16H16Cl2O2S

C16H16Cl2O2S

Conditions
ConditionsYield
With [Cu(2,9-bis(p-anisyl)-1,10-phenanthroline)Cl2] In acetonitrile at 25 - 30℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; regioselective reaction;99%
N,N-dimethyldecylamine
1120-24-7

N,N-dimethyldecylamine

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

decyldimethyl-(4-vinylbenzyl)ammonium chloride

decyldimethyl-(4-vinylbenzyl)ammonium chloride

Conditions
ConditionsYield
In acetonitrile at 40℃; for 239h;99%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

potassium phtalimide
1074-82-4

potassium phtalimide

2-(4-ethenylbenzyl)-1H-isoindole-1,3(2H)-dione
63413-74-1

2-(4-ethenylbenzyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide98%
In N,N-dimethyl-formamide at 110℃; for 5h;88%
In N,N-dimethyl-formamide at 55℃; for 17h;81%
styrene
292638-84-7

styrene

1,4-Divinylbenzene
105-06-6

1,4-Divinylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

polymer; Monomer(s): styrene; 4-chloromethylstyrene; 1,4-divinylbenzene

polymer; Monomer(s): styrene; 4-chloromethylstyrene; 1,4-divinylbenzene

Conditions
ConditionsYield
With dibenzoyl peroxide at 80℃; for 24h;98%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide; water at 125℃; for 0.333333h;98%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 125℃; for 0.666667h;95%
With tetrabutylammomium bromide; sodium hydroxide In water at 125℃; for 2h; Inert atmosphere;57%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

phenyltriisopropoxytitanium(IV)
16635-23-7

phenyltriisopropoxytitanium(IV)

phenyl(p-vinylphenyl)methane
15866-31-6

phenyl(p-vinylphenyl)methane

Conditions
ConditionsYield
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 25℃; for 2h; Inert atmosphere;98%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

undecyl 4'-hydroxybiphenyl-4-carboxylate
132328-89-3

undecyl 4'-hydroxybiphenyl-4-carboxylate

undecyl 4'-(4-vinylbenzyloxy)biphenyl-4-carboxylate
1104078-17-2

undecyl 4'-(4-vinylbenzyloxy)biphenyl-4-carboxylate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 8h;98%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-(4-vinyl-benzylsulfanyl)-ethanol
129509-07-5

2-(4-vinyl-benzylsulfanyl)-ethanol

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium hydroxide In tetrahydrofuran; water Reflux;98%
1H-imidazole
288-32-4

1H-imidazole

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

1-(4-vinylbenzyl)-1H-imidazole
78430-91-8

1-(4-vinylbenzyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydroxide In tetrahydrofuran for 2h; Reflux;
Stage #2: 4-Vinylbenzyl chloride In tetrahydrofuran at 20℃;
98%
With sodium hydrogencarbonate In water; acetone at 20 - 50℃; for 20h;71%
With sodium hydrogencarbonate In acetonitrile at 50℃; for 20h;71%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

propargyl alcohol
107-19-7

propargyl alcohol

1-((prop-2-yn-1-yloxy)methyl)-4-vinylbenzene
132679-16-4

1-((prop-2-yn-1-yloxy)methyl)-4-vinylbenzene

Conditions
ConditionsYield
Stage #1: propargyl alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75h;
Stage #2: 4-Vinylbenzyl chloride With tetra-(n-butyl)ammonium iodide for 12h; Reflux;
98%
Stage #1: propargyl alcohol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4-Vinylbenzyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;
71%
Stage #1: propargyl alcohol With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice;
Stage #2: 4-Vinylbenzyl chloride With tetrabutylammomium bromide In tetrahydrofuran at 20℃; for 5h;
59%

1592-20-7Relevant articles and documents

FACILE SYNTHESIS OF p-CHLOROMETHYLATED STYRENE BY ELIMINATION REACTION OF p-(2-BROMOETHYL)BENZYLCHLORIDE USING POTASSIUM HYDROXIDE AS A BASE UNDER PHASE TRANSFER CATALYSIS

Nishikubo, Tadatomi,Iizawa, Takashi,Kobayashi, Kazuo,Okawara, Makoto

, p. 3873 - 3874 (1981)

Phase transfer catalyzed elimination reactions of p-(2-bromoethyl)-benzylchloride with potassium hydroxide gave p-chloromethylated styrene in high yield.

Preparation method of P-chloromethyl styrene

-

Paragraph 0076-0090, (2021/05/01)

The invention relates to the field of organic chemistry, in particular to a preparation method of p-chloromethyl styrene. The invention provides a preparation method of p-chloromethyl styrene, which comprises the following step: carrying out elimination reaction on 1-(2-chloroethyl)-4-chloromethylbenzene under alkaline conditions to prepare the p-chloromethyl styrene. According to the preparation method, the reaction raw materials with relatively low price are utilized, the manufacturing cost is reduced, the manufacturing process is simple and safe, various side reactions are less, the product conversion rate is high, the purity is high, and thus a good industrialization prospect can be realized.

Synthesis method of p-chloromethyl styrene

-

Paragraph 0043; 0046, (2019/11/25)

The invention relates to a synthesis method of an organic intermediate, in particular, a synthesis method of p-chloromethyl styrene. According to the synthesis method, a phase-transfer catalytic method is adopted; p-chloromethyl-alpha-bromoethylbenzene and potassium hydroxide are taken as the raw materials; toluene is taken as the solvent; and a phase-transfer catalysis is added to synthesize p-chloromethyl styrene. The synthesis method has the advantages that the reactions are mild, the energy consumption is low, no high pressure or high temperature is needed during the reaction process, thereactants do not react with the solvent or the phase-transfer catalyst, the yield is increased, the side reactions are reduced, and a high quality product is obtained.

Highly selective halogenation of unactivated C(sp3)-H with NaX under co-catalysis of visible light and Ag@AgX

Liu, Shouxin,Zhang, Qi,Tian, Xia,Fan, Shiming,Huang, Jing,Whiting, Andrew

, p. 4729 - 4737 (2018/10/23)

The direct selective halogenation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and yields higher than 90%, with the chlorination of toluene being 81%, far higher than the 40% conversion using dichlorine. Mechanistic studies demonstrated that the reaction is a free radical process using blue light (450-500 nm), with visible light being the most effective light source. Irradiation is proposed to cause AgCl bonding electrons to become excited and electron transfer from chloride ions induces chlorine radical formation which drives the substitution reaction. The reaction provides a potentially valuable method for the direct chlorination of saturated hydrocarbons.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Haubenreisser, Stefan,W?ste, Thorsten H.,Martnez, Claudio,Ishihara, Kazuaki,Muiz, Kilian

supporting information, p. 413 - 417 (2016/01/25)

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.

Aromatic cation activation: Nucleophilic substitution of alcohols and carboxylic acids

Nguyen, Thanh V.,Bekensir, Alp

supporting information, p. 1720 - 1723 (2014/04/17)

A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropylium cation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.

Polymerizable compound having mildew resistance and polymer thereof

-

, (2008/06/13)

A novel mildew resistant polymerizable compound of the formula: STR1 wherein X is --0-- or --S--; and Y is a residue of a known mildew proofing compound, preferably, a residue of a compound selected from the group consisting of phenol substituted with 1 to 5 halogen atoms, p-chloro-m-cresol, o-phenylphenol, p-chloro-m-xylenol, salicylanilide, 8-hydroxyquinoline, 2-(4'-thiazolyl)benzimidazole, 2,5-dibromo-4-methylaniline, 1,2-benzoisothiazolin-3-one and 2-pyridinethiol-1-oxide. A polymer of the compound [I] and polyurethane composition containing the polymer are also disclosed.

Carboxy containing monomers

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, (2008/06/13)

Certain ethylenically unsaturated polymerizable monomers having a reactive carboxy group are useful for preparing homo- and copolymers for a variety of uses, including diagnostic assays. The polymers can be supplied as latex particles in aqueous compositions. The monomers are represented by the structure: STR1 wherein: R is hydrogen, halo or alkyl of 1 to 3 carbon atoms, M is hydrogen, an alkali metal ion or an ammonium ion, and L is a linking group having from 8 to 50 atoms in its linking chain, and comprises two or more divalent hydrocarbon groups connected or terminated with one or more nitrogen, oxygen or sulfur atoms, or with one or more groups containing such atoms in the linking chain, provided L has at least one arylene which is not directly connected to the terminal STR2 group, and further provided that none of the hydrocarbon groups has non-aromatic unsaturation.

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