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563-47-3

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563-47-3 Usage

Description

3-Chloro-2-methylpropene is used as an intermediate to produce carbofuran, herbicides, plastics, pharmaceuticals and other organics. It is also used as an additive in textile and perfumes. It was used to study ring opening polymerization of oxirane derivatives using organotin phosphate condensate and cationic polymerization of 3-Chloro-2-methylpropene with AICI3 and AIBr3 as initiators. It is also the reactant for the synthesis of cyclobutanone.

Chemical Properties

clear liquid

Uses

Different sources of media describe the Uses of 563-47-3 differently. You can refer to the following data:
1. 3-Chloro-2-methylpropene has been used as reactant in the synthesis of cyclobutanone. It is used as an intermediate in the production of plastics, pharmaceuticals and other organic chemicals.
2. 3-Chloro-2-methyl-1-propene was used to study ring opening polymerization of oxirane derivatives using organotin phosphate condensate. It was used to study cationic polymerization of 3-Chloro-2-methyl-1-propene using using AICI3 and A3IBr, as initiators.

Biological Functions

MAC is a valuable index for clinical anesthesia, but it is seldom employed without taking other factors into consideration. For example, inhibiting movement in only 50% of patients is not acceptable. Consequently, if an inhalational agent were being used alone—that is, without the administration of other anesthetics or analgesic drugs—the anesthesiologist would employ a multiple of its MAC value to ensure immobility.MAC is frequently multiplied by a factor of 1.3 to achieve nearly 100% clinical efficacy. On the other hand, useful clinical results may be achieved with doses of anesthetics below MAC levels. For example, mild analgesia and amnesia often occur with doses of inhalational agents that are near 0.5 MAC. In this state, it may even be possible to communicate with patients intraoperatively, while their recall is limited.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 824, 1981 DOI: 10.1021/jo00317a041

General Description

A colorless to straw-colored liquid with a sharp penetrating odor. Less dense than water and insoluble in water. Flash point below 0°F. May be toxic by ingestion. Irritating to skin and eyes. Used to make plastics and pharmaceuticals.

Air & Water Reactions

Highly flammable. 3-Chloro-2-methylpropene may react with water at elevated temperatures. . Insoluble in water.

Reactivity Profile

3-Chloro-2-methylpropene is sensitive to light. 3-Chloro-2-methylpropene can react vigorously with oxidizers. 3-Chloro-2-methylpropene is incompatible with strong bases. 3-Chloro-2-methylpropene may react with water at elevated temperatures. .

Hazard

Irritant; poison; anesthetic; questionable carcinogen; toxic.

Health Hazard

Inhalation causes irritation of nose and throat. Contact of vapor or liquid with eyes causes irritation. Liquid irritates skin. Ingestion causes irritation of mouth and stomach.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Experimental reproductive effects. An irritant. Human mutation data reported. Very dangerous fire hazard when exposed to heat, flame, or oxidizers. Moderately explosive when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, ALIPHATIC; and ALLYL COMPOUNDS.

Carcinogenicity

3-Chloro-2-methylpropene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Check Digit Verification of cas no

The CAS Registry Mumber 563-47-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 3 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 563-47:
(5*5)+(4*6)+(3*3)+(2*4)+(1*7)=73
73 % 10 = 3
So 563-47-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H7Cl/c1-4(2)3-5/h1,3H2,2H3

563-47-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (B22674)  3-Chloro-2-methylpropene, 98%   

  • 563-47-3

  • 50g

  • 435.0CNY

  • Detail
  • Alfa Aesar

  • (B22674)  3-Chloro-2-methylpropene, 98%   

  • 563-47-3

  • 250g

  • 718.0CNY

  • Detail
  • Alfa Aesar

  • (B22674)  3-Chloro-2-methylpropene, 98%   

  • 563-47-3

  • 1000g

  • 2269.0CNY

  • Detail
  • Aldrich

  • (281972)  3-Chloro-2-methyl-1-propene  contains ~250 ppm Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) as stabilizer, 98%

  • 563-47-3

  • 281972-100ML

  • 599.04CNY

  • Detail
  • Aldrich

  • (281972)  3-Chloro-2-methyl-1-propene  contains ~250 ppm Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) as stabilizer, 98%

  • 563-47-3

  • 281972-1L

  • 1,708.20CNY

  • Detail
  • Aldrich

  • (108030)  3-Chloro-2-methyl-1-propene  technical grade, 90%

  • 563-47-3

  • 108030-100ML

  • 273.78CNY

  • Detail
  • Aldrich

  • (108030)  3-Chloro-2-methyl-1-propene  technical grade, 90%

  • 563-47-3

  • 108030-1L

  • CNY

  • Detail

563-47-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Chloro-2-methylpropene

1.2 Other means of identification

Product number -
Other names 3-chloro-2-methylprop-1-ene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:563-47-3 SDS

563-47-3Synthetic route

3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine In sulfolane from 10 deg C to room temp.;95.7%
With pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran Ambient temperature;65%
With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine In sulfolane from 10 deg C to room temp., effect of reagents ratio and solvent volume discussed;
2-methallyl diphenylphosphate
32670-93-2

2-methallyl diphenylphosphate

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-formamide for 0.166667h; Ambient temperature;64%
Pd(CH2CHCH2)(C6H3Cl2)(As(C6H5)3)

Pd(CH2CHCH2)(C6H3Cl2)(As(C6H5)3)

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

CH2CHCH2C6H3Cl2
90220-53-4

CH2CHCH2C6H3Cl2

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
In dichloromethane O°C, AsPh3 was added, 24 h.;A 55%
B 20%
In dichloromethane O°C, AsPh3 was added, 1.33 h.;A 22%
B 2%
In dichloromethane O°C, AsPh3 was added, 0.67 h.;A 10%
B 0%
In dichloromethane O°C, AsPh3 was added, 0.33 h.;A 6%
B 0%
boric acid trimethallyl ester
78538-54-2

boric acid trimethallyl ester

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With boron trichloride at 120℃;
isopropenylmethyl ether
628-56-8

isopropenylmethyl ether

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With hydrogenchloride; copper(l) chloride at 30 - 50℃; under 89731.9 Torr;
N,N-dichlorourea
36942-09-3

N,N-dichlorourea

acetic acid
64-19-7

acetic acid

isobutene
115-11-7

isobutene

A

acetic acid-(chloro-tert-butyl ester)
57576-87-1

acetic acid-(chloro-tert-butyl ester)

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

N,N-dichlorourea
36942-09-3

N,N-dichlorourea

isobutene
115-11-7

isobutene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With acetic acid
With trichloroacetic acid
With chloroacetic acid
N,N-Dichlorobenzenesulfonamide
473-29-0

N,N-Dichlorobenzenesulfonamide

diethyl ether
60-29-7

diethyl ether

isobutene
115-11-7

isobutene

2-chloro-ethanol
107-07-3

2-chloro-ethanol

A

1-chloro-2-(2-chloroethoxy)-2-methylpropane
55982-53-1

1-chloro-2-(2-chloroethoxy)-2-methylpropane

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

isobutene
115-11-7

isobutene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
Chlorierung;
With chlorine at 0 - 70℃;
With chlorine at 0℃;
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

C

tertiary butyl chloride
507-20-0

tertiary butyl chloride

D

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 80℃; Chlorierung;
With chlorine In tetrachloromethane at 20℃;A n/a
B 6 % Chromat.
C n/a
D 77 % Chromat.
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
bei der Chlorierung;
isobutene
115-11-7

isobutene

A

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With nitrogen trichloride In dichloromethane
With chlorine at 70℃; under 760.051 Torr; for 24h; Inert atmosphere;A 8.73 %Chromat.
B 79.47 %Chromat.
1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 380.1℃; Kinetics; Thermodynamic data; pyrolysis; Ea; var. temp. and initial pressure;
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

2-chloromethyl-3-chloroprop-1-ene
1871-57-4

2-chloromethyl-3-chloroprop-1-ene

C

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

D

(E)-1,3-Dichloro-2-methyl-1-propene
35329-41-0

(E)-1,3-Dichloro-2-methyl-1-propene

E

(Z)-1,3-Dichloro-2-methyl-1-propene
35329-40-9

(Z)-1,3-Dichloro-2-methyl-1-propene

F

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With chlorine at 40 - 70℃; Product distribution; various conc.; further products;
tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

triethyl phosphite
122-52-1

triethyl phosphite

A

triethyl phosphate
78-40-0

triethyl phosphate

B

tertiary butyl chloride
507-20-0

tertiary butyl chloride

C

Ethyl tert-butyl ether
637-92-3

Ethyl tert-butyl ether

D

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

E

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

F

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
In dichloromethane at 20℃; Rate constant;
3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine In sulfolane from 10 deg C to room temp.;95.7%
With pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran Ambient temperature;65%
With 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine In sulfolane from 10 deg C to room temp., effect of reagents ratio and solvent volume discussed;
2-methallyl diphenylphosphate
32670-93-2

2-methallyl diphenylphosphate

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-formamide for 0.166667h; Ambient temperature;64%
Pd(CH2CHCH2)(C6H3Cl2)(As(C6H5)3)

Pd(CH2CHCH2)(C6H3Cl2)(As(C6H5)3)

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

CH2CHCH2C6H3Cl2
90220-53-4

CH2CHCH2C6H3Cl2

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
In dichloromethane O°C, AsPh3 was added, 24 h.;A 55%
B 20%
In dichloromethane O°C, AsPh3 was added, 1.33 h.;A 22%
B 2%
In dichloromethane O°C, AsPh3 was added, 0.67 h.;A 10%
B 0%
In dichloromethane O°C, AsPh3 was added, 0.33 h.;A 6%
B 0%
boric acid trimethallyl ester
78538-54-2

boric acid trimethallyl ester

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With boron trichloride at 120℃;
isopropenylmethyl ether
628-56-8

isopropenylmethyl ether

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With hydrogenchloride; copper(l) chloride at 30 - 50℃; under 89731.9 Torr;
N,N-dichlorourea
36942-09-3

N,N-dichlorourea

acetic acid
64-19-7

acetic acid

isobutene
115-11-7

isobutene

A

acetic acid-(chloro-tert-butyl ester)
57576-87-1

acetic acid-(chloro-tert-butyl ester)

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

N,N-dichlorourea
36942-09-3

N,N-dichlorourea

isobutene
115-11-7

isobutene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With acetic acid
With trichloroacetic acid
With chloroacetic acid
N,N-Dichlorobenzenesulfonamide
473-29-0

N,N-Dichlorobenzenesulfonamide

diethyl ether
60-29-7

diethyl ether

isobutene
115-11-7

isobutene

2-chloro-ethanol
107-07-3

2-chloro-ethanol

A

1-chloro-2-(2-chloroethoxy)-2-methylpropane
55982-53-1

1-chloro-2-(2-chloroethoxy)-2-methylpropane

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

isobutene
115-11-7

isobutene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
Chlorierung;
With chlorine at 0 - 70℃;
With chlorine at 0℃;
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

C

tertiary butyl chloride
507-20-0

tertiary butyl chloride

D

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 80℃; Chlorierung;
With chlorine In tetrachloromethane at 20℃;A n/a
B 6 % Chromat.
C n/a
D 77 % Chromat.
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
bei der Chlorierung;
isobutene
115-11-7

isobutene

A

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With nitrogen trichloride In dichloromethane
With chlorine at 70℃; under 760.051 Torr; for 24h; Inert atmosphere;A 8.73 %Chromat.
B 79.47 %Chromat.
1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 380.1℃; Kinetics; Thermodynamic data; pyrolysis; Ea; var. temp. and initial pressure;
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

2-chloromethyl-3-chloroprop-1-ene
1871-57-4

2-chloromethyl-3-chloroprop-1-ene

C

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

D

(E)-1,3-Dichloro-2-methyl-1-propene
35329-41-0

(E)-1,3-Dichloro-2-methyl-1-propene

E

(Z)-1,3-Dichloro-2-methyl-1-propene
35329-40-9

(Z)-1,3-Dichloro-2-methyl-1-propene

F

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With chlorine at 40 - 70℃; Product distribution; various conc.; further products;
tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

triethyl phosphite
122-52-1

triethyl phosphite

A

triethyl phosphate
78-40-0

triethyl phosphate

B

tertiary butyl chloride
507-20-0

tertiary butyl chloride

C

Ethyl tert-butyl ether
637-92-3

Ethyl tert-butyl ether

D

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

E

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

F

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
In dichloromethane at 20℃; Rate constant;
acetic acid
64-19-7

acetic acid

Methylcyclopropen
3100-04-7

Methylcyclopropen

A

methallyl acetate
820-71-3

methallyl acetate

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With hydrogenchloride at 0℃;
Methylcyclopropen
3100-04-7

Methylcyclopropen

A

methallyl acetate
820-71-3

methallyl acetate

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With hydrogenchloride In acetic acid at 0℃; Product distribution; var. concentration of HCl and reaction times, other substituted cyclopropene;
With hydrogenchloride In acetic acid at 0℃;
isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

C

tertiary butyl chloride
507-20-0

tertiary butyl chloride

D

1,2,3-trichloro-2-methylpropane
1871-58-5

1,2,3-trichloro-2-methylpropane

E

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With Bu3(PhCH2)NCl*2Cl2 In tetrachloromethane at 20℃; Product distribution; other reagents, other concentration;A n/a
B 69 % Chromat.
C n/a
D 19 % Chromat.
E 9 % Chromat.
isobutene
115-11-7

isobutene

A

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

B

1,2,3-trichloro-2-methylpropane
1871-58-5

1,2,3-trichloro-2-methylpropane

C

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With Bu3(PhCH2)NCl*2Cl2 In tetrachloromethane at 20℃;A 74 % Chromat.
B 18 % Chromat.
C 8 % Chromat.
With Bu3(PhCH2)NCl*2Cl2 In tetrachloromethane at 20℃;A 34 % Chromat.
B 62 % Chromat.
C 3 % Chromat.
chlorine
7782-50-5

chlorine

isobutene
115-11-7

isobutene

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 0℃; Mechanism;
water
7732-18-5

water

hypochloric acid
13898-47-0

hypochloric acid

isobutene
115-11-7

isobutene

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

3-chloro-2-methylpropan-2-ol
558-42-9

3-chloro-2-methylpropan-2-ol

C

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
Mechanism;
isobutene
115-11-7

isobutene

charcoal

charcoal

A

2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

B

1,2-dichloro-2-methylpropane
594-37-6

1,2-dichloro-2-methylpropane

C

tertiary butyl chloride
507-20-0

tertiary butyl chloride

D

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 200 - 450℃; Chlorierung;
N,N-Dichlorobenzenesulfonamide
473-29-0

N,N-Dichlorobenzenesulfonamide

chloroform
67-66-3

chloroform

isobutene
115-11-7

isobutene

phenol
108-95-2

phenol

A

(chloro-tert-butyl)-phenyl ether

(chloro-tert-butyl)-phenyl ether

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

C

1-chloro-2-benzenesulfonylamino-2-methyl-propane

1-chloro-2-benzenesulfonylamino-2-methyl-propane

water
7732-18-5

water

chlorine
7782-50-5

chlorine

isobutene
115-11-7

isobutene

A

3-chloro-2-methylpropan-2-ol
558-42-9

3-chloro-2-methylpropan-2-ol

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
at 100℃;
N,N-dichlorourea
36942-09-3

N,N-dichlorourea

acetic acid
64-19-7

acetic acid

isobutene
115-11-7

isobutene

A

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

B

tert-butyl>-acetate

tert-butyl>-acetate

formic acid
64-18-6

formic acid

N,N-dichlorourea
36942-09-3

N,N-dichlorourea

isobutene
115-11-7

isobutene

A

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

B

tert-butyl>-formate

tert-butyl>-formate

isobutylenechloro hydride

isobutylenechloro hydride

A

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

B

(CH3)2C:CHCl

(CH3)2C:CHCl

Conditions
ConditionsYield
With oxalic acid Beim Destillieren;
With phosphorus pentoxide Beim Destillieren;
3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

A

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

B

Ti(OCH2C(CH3)=CH2)4

Ti(OCH2C(CH3)=CH2)4

Conditions
ConditionsYield
With titanium tetrachloride
2-methylprop-1-enyl chloride
513-37-1

2-methylprop-1-enyl chloride

sulfuric acid
7664-93-9

sulfuric acid

A

3-chloro-2-methylpropan-2-ol
558-42-9

3-chloro-2-methylpropan-2-ol

B

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

ethyl 2-acetyl-4-methylpent-4-enoate
20962-70-3

ethyl 2-acetyl-4-methylpent-4-enoate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40 - 75℃; for 6h;100%
With tetrabutylammomium bromide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40 - 75℃; for 6h;100%
With tetrabutylammomium bromide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40 - 75℃; for 6h;100%
Conditions
ConditionsYield
With copper(l) iodide; TEA at 60℃;100%
With copper(l) iodide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; potassium iodide; sodium sulfite In water; benzene at 75 - 80℃; for 6h;92%
With potassium carbonate; copper(l) iodide; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide for 16h; Product distribution; Ambient temperature; variation of catalysts and reaction time;88%
4-bromo-phenol
106-41-2

4-bromo-phenol

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

1-(2’-methylallyloxy)-4-bromobenzene
5820-27-9

1-(2’-methylallyloxy)-4-bromobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 18h; Inert atmosphere;100%
With potassium carbonate In acetone Inert atmosphere; Reflux;87%
With potassium carbonate; acetone
With potassium carbonate In acetone
With potassium carbonate In N,N-dimethyl-formamide at 70℃;
3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

trichloro(2-methyl-2-propenyl)silane
18147-56-3

trichloro(2-methyl-2-propenyl)silane

Conditions
ConditionsYield
With tetrachlorosilane; 1,1,2-trichloro-1,2,2-trimethyldisilane; 1,1,2,2-tetrachloro-1,2-dimethyldisilane; N,N,N,N,N,N-hexamethylphosphoric triamide; nickelocene for 15h; Heating;100%
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrachlorosilane; nickelocene for 15h; Heating;100%
With tetrachlorosilane; triethylamine; copper(l) chloride78%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2-methyl-3-(2',2',2'-trifluoroethoxy)-prop-1-ene
74407-77-5

2-methyl-3-(2',2',2'-trifluoroethoxy)-prop-1-ene

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide100%
Stage #1: 2,2,2-trifluoroethanol With potassium hydroxide at 40℃;
Stage #2: 3-Chloro-2-methylpropene In water at 40℃;
78%
With potassium carbonate In N,N-dimethyl-formamide
4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide
286376-23-6

4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

N-(but-2-ynyl)-4-methyl-N-(2-methylallyl)benzenesulfonamide
292607-11-5

N-(but-2-ynyl)-4-methyl-N-(2-methylallyl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: 4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: 3-Chloro-2-methylpropene With sodium iodide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 9h; Further stages.;
100%
N-benzylidene ethylamine
27845-47-2

N-benzylidene ethylamine

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

Conditions
ConditionsYield
With zinc In tetrahydrofuran at 20℃; for 4h;100%
2-iodo-N,N-diallylaniline
73396-92-6

2-iodo-N,N-diallylaniline

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

N,N-diallyl-2-(2-methylprop-2-en-1-yl)aniline
882788-93-4

N,N-diallyl-2-(2-methylprop-2-en-1-yl)aniline

Conditions
ConditionsYield
Stage #1: 2-iodo-N,N-diallylaniline With TurboGrignard In tetrahydrofuran at -10℃; for 0.5h;
Stage #2: 3-Chloro-2-methylpropene In tetrahydrofuran at -10 - 20℃; for 12h;
100%
Stage #1: 2-iodo-N,N-diallylaniline With TurboGrignard In tetrahydrofuran at -10℃; for 1h;
Stage #2: 3-Chloro-2-methylpropene With copper(I) cyanide lithium chloride In tetrahydrofuran at -10 - 20℃; for 25h;
Stage #1: 2-iodo-N,N-diallylaniline With TurboGrignard In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere;
Stage #2: 3-Chloro-2-methylpropene With copper(I) cyanide di(lithium chloride) In tetrahydrofuran at -10 - 20℃;
568 mg
Stage #1: 2-iodo-N,N-diallylaniline With isopropylmagnesium chloride In tetrahydrofuran at -10℃;
Stage #2: 3-Chloro-2-methylpropene With copper(l) cyanide; lithium chloride at -10 - 20℃;
3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2-methyl-2-propenyl azide
104131-54-6

2-methyl-2-propenyl azide

Conditions
ConditionsYield
With sodium azide In dimethyl sulfoxide at 20℃; for 2.5h;100%
With sodium azide In dimethyl sulfoxide at 70℃; for 15h;
With sodium azide In dimethyl sulfoxide at 70℃; for 15h;
(R)-1-octyn-3-ol
32556-70-0

(R)-1-octyn-3-ol

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

C12H20O
913977-05-6

C12H20O

Conditions
ConditionsYield
With copper(l) iodide; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;100%
(R)-(tert-butyldiphenylsilyloxy)methyloxirane
107033-46-5

(R)-(tert-butyldiphenylsilyloxy)methyloxirane

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

C23H32O2Si
945468-53-1

C23H32O2Si

Conditions
ConditionsYield
Stage #1: 3-Chloro-2-methylpropene With magnesium In tetrahydrofuran at 24℃; for 1h;
Stage #2: (R)-(tert-butyldiphenylsilyloxy)methyloxirane In tetrahydrofuran at -40℃; for 5h; Further stages.;
100%
tert-butyl N-(7-(tert-butyl)-2,3-dihydro-2,2,4-trimethyl-1-benzofuran-5-yl]carbamate

tert-butyl N-(7-(tert-butyl)-2,3-dihydro-2,2,4-trimethyl-1-benzofuran-5-yl]carbamate

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

7-(tert-Butyl)-2,3-dihydro-5-(2-methyl-2-propenyl)amino-2,2,4-trimethyl-1-benzofurane

7-(tert-Butyl)-2,3-dihydro-5-(2-methyl-2-propenyl)amino-2,2,4-trimethyl-1-benzofurane

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; potassium iodide In methanol; N,N-dimethyl-formamide100%
With sodium hydroxide; concentrated hydrochloric acid; potassium iodide In methanol; sodium hydride; N,N-dimethyl-formamide
benzyl salicylate
118-58-1

benzyl salicylate

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

benzyl 2-(2-methylallyl-oxy)benzoate

benzyl 2-(2-methylallyl-oxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide100%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2-methylallyl 5-chloro-2-(2-methylallyloxy)benzoate

2-methylallyl 5-chloro-2-(2-methylallyloxy)benzoate

Conditions
ConditionsYield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 0.0833333h; Inert atmosphere;
Stage #2: 3-Chloro-2-methylpropene In N,N-dimethyl-formamide at 65℃; for 21h;
100%
With potassium carbonate In N-methyl-acetamide
1-<4-(1H-indol-3-yl)piperidino>ethanone
30030-83-2

1-<4-(1H-indol-3-yl)piperidino>ethanone

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

1-{4-[1-(2-methylallyl)-1H-indol-3-yl]-piperidin-1-yl}-ethanone
648882-71-7

1-{4-[1-(2-methylallyl)-1H-indol-3-yl]-piperidin-1-yl}-ethanone

Conditions
ConditionsYield
Stage #1: 1-<4-(1H-indol-3-yl)piperidino>ethanone With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.333333h;
Stage #2: 3-Chloro-2-methylpropene In DMF (N,N-dimethyl-formamide) at 20℃;
100%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

1-[3-(2-methylallyloxy)phenyl]ethanone
1017048-68-8

1-[3-(2-methylallyloxy)phenyl]ethanone

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃;100%
With potassium carbonate In acetonitrile for 17h; Reflux;

563-47-3Relevant articles and documents

METHOD FOR PREPARING 2-METHYLALLYL CHLORIDE FROM 1,2-DICHLOROTERT-BUTANE

-

Paragraph 0026, (2021/11/26)

The present invention relates to a method for preparing 2-methylallyl chloride from 1,2-dichloro-tert-butane. The method is characterized in that 1,2-dichloro-tert-butane and a sodium hydroxide aqueous solution are used as raw materials; reactive rectification is performed in a combined rectifying tower to eliminate hydrogen chloride so as to obtain 2-methylallyl chloride. A plate type tower is provided at the lower part of the combined rectifying tower; a packing tower is provided at the upper part of the combined rectifying tower; an inner reflux condenser is provided at the top of the combined rectifying tower. The sodium hydroxide aqueous solution is added from a first plate of the plate type tower; and 1,2-dichloro-tert-butane is added from the middle part of the plate type tower. The method has the advantages that the raw material 1 and 1,2-dichloro-tert-butane is fully converted; the selectivity of the 2-methylallyl chloride is high.

Method for co-producing methyl chloropropene and 2-chloro-2-methylpropane by chlorination of isobutene

-

Paragraph 0025; 0026, (2020/01/12)

The invention discloses a method for co-producing methyl chloropropene and 2-chloro-2-methylpropane by chlorination of isobutene. According to the method, a chlorination reaction is carried out on chlorine or a mixture of chlorine and inert gas and excessive isobutene to obtain products, namely methyl chloropropene and 2-chloro-2-methylpropane. The method can reduce influence of micro-mixing on arapid chlorination reaction of isobutene, decarburization and coking do not occur easily, and 2-chloro-2-methylpropane can be co-produced while the yield of methyl chloropropene is improved.

Quaternary ammonium polychlorides as efficient reagents for chlorination of unsaturated compounds

Zelikman,Tyurin,Smirnov,Zyk

, p. 1541 - 1546 (2007/10/03)

Chlorination of unsaturated compounds by benzyltributylammonium polychlorides results in higher yields of addition products compared to those obtained with molecular chlorine.

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