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13547-70-1 Usage

Description

1-Chloropinacolone, also known as 1-chloro-2-methoxypropanone, is an organic compound with the molecular formula C4H7ClO. It is a clear, slightly yellow liquid at room temperature and is commonly used as a synthetic intermediate in the production of various chemical compounds due to its reactive nature.

Uses

1. Used in Pharmaceutical Industry:
1-Chloropinacolone is used as an intermediate for the synthesis of triazole compounds, which possess significant biological activities. These triazole compounds are known for their antiviral, antibacterial, antifungal, and antituberculous properties, making them valuable in the development of new drugs and treatments for various diseases and infections.
2. Used in Chemical Synthesis:
1-Chloropinacolone serves as a versatile building block in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional group compatibility make it a popular choice for chemists working on the development of new molecules with potential applications in various industries.
3. Used in Research and Development:
In addition to its applications in the pharmaceutical and chemical industries, 1-Chloropinacolone is also utilized in research and development settings. Scientists and researchers use this compound to explore new reaction pathways, develop novel synthetic methods, and investigate the properties of related compounds, ultimately contributing to the advancement of chemical knowledge and innovation.

Hazard

A poison by ingestion. Low toxicity byinhalation.

Check Digit Verification of cas no

The CAS Registry Mumber 13547-70-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,5,4 and 7 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 13547-70:
(7*1)+(6*3)+(5*5)+(4*4)+(3*7)+(2*7)+(1*0)=101
101 % 10 = 1
So 13547-70-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H11ClO/c1-6(2,3)5(8)4-7/h4H2,1-3H3

13547-70-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A16576)  1-Chloropinacolone, 95%   

  • 13547-70-1

  • 25g

  • 342.0CNY

  • Detail
  • Alfa Aesar

  • (A16576)  1-Chloropinacolone, 95%   

  • 13547-70-1

  • 100g

  • 969.0CNY

  • Detail
  • Alfa Aesar

  • (A16576)  1-Chloropinacolone, 95%   

  • 13547-70-1

  • 500g

  • 4114.0CNY

  • Detail

13547-70-1SDS

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 1-Chloropinacolone

1.2 Other means of identification

Product number -
Other names monochloropinacolone

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:13547-70-1 SDS

13547-70-1Synthetic route

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With chlorine In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate92%
With p-toluenesulfonyl chloride; lithium diisopropyl amide In tetrahydrofuran -78 deg C to room t., 1 h;65%
With hydrogenchloride; sodium chlorate at 0℃; for 1h;48.8%
pinacoyl (4-methoxyphenyl)tellurium dichloride
112449-69-1

pinacoyl (4-methoxyphenyl)tellurium dichloride

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

bis(4-methoxyphenyl)ditelluride
35684-37-8

bis(4-methoxyphenyl)ditelluride

C

elemental tellurium

elemental tellurium

Conditions
ConditionsYield
at 210℃; under 30 Torr; for 0.0833333h;A 85%
B n/a
C n/a
3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene
17510-46-2

3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With copper dichloride In N,N-dimethyl-formamide 1) r.t., 3 h, 2) 50 deg C, 30 min; further reagent: FeCl3 in MeCN;65%
Multi-step reaction with 2 steps
1: 94 percent / benzene / 10 h / Heating
2: 85 percent / 0.08 h / 210 °C / 30 Torr
View Scheme
(E)-1-chloro-3,3-dimethyl-2-methylthiobut-1-ene
83759-13-1

(E)-1-chloro-3,3-dimethyl-2-methylthiobut-1-ene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With trifluoroacetic acid at 0℃; for 1h;60%
1-chloro-3,3-dimethyl-2-methylthiobut-1-ene

1-chloro-3,3-dimethyl-2-methylthiobut-1-ene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With trifluoroacetic acid at 0℃; for 1h;60%
1-chloro-3,3-dimethyl-2-p-tolylthiobut-1-ene

1-chloro-3,3-dimethyl-2-p-tolylthiobut-1-ene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With trifluoroacetic acid at 0℃; for 1h;60%
(Z)-1-chloro-3,3-dimethyl-2-p-tolylthiobut-1-ene
83759-14-2

(Z)-1-chloro-3,3-dimethyl-2-p-tolylthiobut-1-ene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With trifluoroacetic acid at 0℃; for 1h;60%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

1,1-dichloro-3,3-dimethylbutan-2-one
22591-21-5

1,1-dichloro-3,3-dimethylbutan-2-one

C

1,4-dichloro-3,3-dimethyl-butan-2-one
35039-88-4

1,4-dichloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
beim Chlorieren in der Dampfphase;
pivaloyl chloride
3282-30-2

pivaloyl chloride

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
(i), (ii) HCl; Multistep reaction;
(1-dichloromethyl-2,2-dimethyl-propoxy)-trimethyl-silane
36402-36-5

(1-dichloromethyl-2,2-dimethyl-propoxy)-trimethyl-silane

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; diethyl ether at -110 - -50℃;
1,1-dichloro-3,3-dimethyl-2-butanol
30263-69-5

1,1-dichloro-3,3-dimethyl-2-butanol

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With piperidine; n-butyllithium
at 130 - 140℃;
Multi-step reaction with 2 steps
1: Py / benzene / 18 h / Ambient temperature
2: nBuLi / diethyl ether; tetrahydrofuran / -110 - -50 °C
View Scheme
4-chloro-3-methoxy-2,3-dimethyl-butan-2-ol
14889-24-8

4-chloro-3-methoxy-2,3-dimethyl-butan-2-ol

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With sulfuric acid
((E)-1-tert-butyl-2-chloro-vinyloxy)-benzene

((E)-1-tert-butyl-2-chloro-vinyloxy)-benzene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With hydrogenchloride
2-tert-Butyl-2-chlorooxirane
76955-39-0

2-tert-Butyl-2-chlorooxirane

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

1-fluoro-3,3-dimethyl-2-butanone
4538-80-1

1-fluoro-3,3-dimethyl-2-butanone

Conditions
ConditionsYield
With F In diethyl ether at -75℃;
With silver tetrafluoroborate In diethyl ether for 1h; Ambient temperature; Yield given. Yields of byproduct given;
[1-Chloromethyl-2,2-dimethyl-prop-(E)-ylidene]-methyl-amine

[1-Chloromethyl-2,2-dimethyl-prop-(E)-ylidene]-methyl-amine

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With sulfuric acid for 0.25h;
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CCl4 / Ambient temperature
2: 60 percent / CF3COOH / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: CHCl3 / Ambient temperature
2: 60 percent / CF3COOH / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: CCl4 / Ambient temperature
2: 60 percent / CF3COOH / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: CHCl3 / Ambient temperature
2: 60 percent / CF3COOH / 1 h / 0 °C
View Scheme
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

aqueous glycolmonomethyl ether

aqueous glycolmonomethyl ether

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / benzene / 72 h / Heating
2: 85 percent / 0.08 h / 210 °C / 30 Torr
View Scheme
2-chloro-3,3-dimethyl-1-butene
27843-27-2

2-chloro-3,3-dimethyl-1-butene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60.5 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / Ambient temperature
2: AgBF4 / diethyl ether / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 31 percent / acide m-chloroperoxybenzoique / CH2Cl2 / 15 h / Ambient temperature
2: n-Bu3MePF / diethyl ether / -75 °C
View Scheme
pivalaldehyde
630-19-3

pivalaldehyde

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) nBuLi, (ii) /BRN= 506060/
2: nBuLi, piperidine
View Scheme
1,1-dichloro-3,3-dimethylbutan-2-one
22591-21-5

1,1-dichloro-3,3-dimethylbutan-2-one

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4, Et2O
2: 130 - 140 °C
View Scheme
tert-butyl-2-chloro-acetylene
16865-61-5

tert-butyl-2-chloro-acetylene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide; methanol
2: aq. HCl
View Scheme
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

1,1-dichloro-3,3-dimethylbutan-2-one
22591-21-5

1,1-dichloro-3,3-dimethylbutan-2-one

Conditions
ConditionsYield
With chlorine; hydrogenchloride at 150℃; Heating / reflux;
With chlorine; hydrogenchloride Heating / reflux;
With chlorine
With 1,3-dichloro-5,5-dimethylhydantoin; silica gel In methanol for 1h; Reflux;
1-chloro-3,3-dimethyl-2-phenoxy-1-butene

1-chloro-3,3-dimethyl-2-phenoxy-1-butene

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With hydrogenchloride; formic acid
1-hydroxy-3,3-dimethylbutan-2-one
38895-88-4

1-hydroxy-3,3-dimethylbutan-2-one

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

4-tert-butyl-5H-[1,2,3]oxathiazole 2,2-dioxide
1025506-09-5

4-tert-butyl-5H-[1,2,3]oxathiazole 2,2-dioxide

C

C6H13NO4S

C6H13NO4S

Conditions
ConditionsYield
With pyridine; formic acid; isocyanate de chlorosulfonyle In acetonitrile at 0 - 10℃; Inert atmosphere;
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

1,1-dichloro-3,3-dimethylbutan-2-one
22591-21-5

1,1-dichloro-3,3-dimethylbutan-2-one

C

1,4-dichloro-3,3-dimethyl-butan-2-one
35039-88-4

1,4-dichloro-3,3-dimethyl-butan-2-one

D

2,2,5,6,6-pentamethyl-hept-4-en-3-one
3205-31-0

2,2,5,6,6-pentamethyl-hept-4-en-3-one

E

1,1,1-trichloro-3,3-dimethyl-2-butanone
36965-30-7

1,1,1-trichloro-3,3-dimethyl-2-butanone

F

1,1,4-trichloro-3,3-dimethyl-butan-2-one
35039-89-5

1,1,4-trichloro-3,3-dimethyl-butan-2-one

G

4-chloro-3,3-dimethylbutane-2-one
13104-53-5

4-chloro-3,3-dimethylbutane-2-one

H

1,4-dichloro-3-chloromethyl-3-methyl-butan-2-one
35039-91-9

1,4-dichloro-3-chloromethyl-3-methyl-butan-2-one

I

1,1,4,4-tetrachloro-3,3-dimethyl-butan-2-one
35039-92-0

1,1,4,4-tetrachloro-3,3-dimethyl-butan-2-one

J

1,1,4-trichloro-3-chloromethyl-3-methyl-butan-2-one
35039-93-1

1,1,4-trichloro-3-chloromethyl-3-methyl-butan-2-one

K

1,1,1,4-tetrachloro-3-methyl-3-(chloromethyl)butan-2-one

1,1,1,4-tetrachloro-3-methyl-3-(chloromethyl)butan-2-one

L

1,1,4-trichloro-3,3-bis-(chloromethyl)butan-2-one

1,1,4-trichloro-3,3-bis-(chloromethyl)butan-2-one

M

C6H6Cl6O

C6H6Cl6O

N

C6H6Cl6O

C6H6Cl6O

O

1,1,1,4,4-pentachloro-3,3-bis(chloromethyl)butane-2-one

1,1,1,4,4-pentachloro-3,3-bis(chloromethyl)butane-2-one

P

1,1,1,4,4,4-hexachloro-3-(dichloromethyl)-3-(chloromethyl)butane-2-one

1,1,1,4,4,4-hexachloro-3-(dichloromethyl)-3-(chloromethyl)butane-2-one

Conditions
ConditionsYield
With chlorine In tetrachloromethane for 1h; Irradiation;
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

A

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

B

4-chloro-3,3-dimethylbutane-2-one
13104-53-5

4-chloro-3,3-dimethylbutane-2-one

Conditions
ConditionsYield
With sulfuryl dichloride In tetrachloromethane at 20℃;
3'-[4-(hydroxy)-3-methylphenyl]-3'-[4-methylthiophen-2-yl]pentane
633337-86-7

3'-[4-(hydroxy)-3-methylphenyl]-3'-[4-methylthiophen-2-yl]pentane

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-{4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one
633339-85-2

1-{4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With potassium carbonate In acetone Heating / reflux;100%
With potassium carbonate In acetone Heating / reflux;100%
3'-[4-(hydroxy)-3-methylphenyl]-3'-[5-methoxycarbonyl-4-methylthiophen-2-yl]pentane
633337-89-0

3'-[4-(hydroxy)-3-methylphenyl]-3'-[5-methoxycarbonyl-4-methylthiophen-2-yl]pentane

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

3'-[4-(2-oxo-3,3-dimethylbutoxy)-3-methylphenyl]-3'-[5-methoxycarbonyl-4-methylthiophen-2-yl]pentane
633337-84-5

3'-[4-(2-oxo-3,3-dimethylbutoxy)-3-methylphenyl]-3'-[5-methoxycarbonyl-4-methylthiophen-2-yl]pentane

Conditions
ConditionsYield
With potassium carbonate In acetone Heating / reflux;100%
With potassium carbonate In acetone at 20℃; Product distribution / selectivity; Heating / reflux;100%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-azido-3,3-dimethyl-2-butanone
76779-98-1

1-azido-3,3-dimethyl-2-butanone

Conditions
ConditionsYield
With sodium azide In acetone at 25℃;100%
With sodium azide In acetone for 36h; Inert atmosphere;79%
With sodium azide In acetone at 25℃;
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

methyl 3-(3-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-1H-indol-6-yl)propanoate
1445854-08-9

methyl 3-(3-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-1H-indol-6-yl)propanoate

methyl 3-(3-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1H-indol-6-yl)propanoate
1445854-09-0

methyl 3-(3-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1H-indol-6-yl)propanoate

Conditions
ConditionsYield
With potassium carbonate Inert atmosphere;100%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

pivalaldehyde
630-19-3

pivalaldehyde

5-hydroxy-2,2,6,6-tetramethyl-3-heptanone
42052-53-9

5-hydroxy-2,2,6,6-tetramethyl-3-heptanone

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at -78℃; for 1.41667h; Reformatsky type reaction; Inert atmosphere;99%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

1-cyclohexyl-1-hydroxy-4,4-dimethylpentan-3-one
65651-67-4

1-cyclohexyl-1-hydroxy-4,4-dimethylpentan-3-one

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at -78℃; for 1.41667h; Reformatsky type reaction; Inert atmosphere;99%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

p-toluidine
106-49-0

p-toluidine

N-(pivaloylmethyl)-4-methylaniline

N-(pivaloylmethyl)-4-methylaniline

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 75℃; for 48h;99%
7-hydroxy-3-methoxycarbonylmethyl-4-methyl-2H-chromen-2-one
95903-37-0

7-hydroxy-3-methoxycarbonylmethyl-4-methyl-2H-chromen-2-one

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

methyl [4-methyl-7-(3',3'-dimethyl-2'-oxobutoxy)-2-oxo-2H-benzopyran-3-yl]-acetate
664365-85-9

methyl [4-methyl-7-(3',3'-dimethyl-2'-oxobutoxy)-2-oxo-2H-benzopyran-3-yl]-acetate

Conditions
ConditionsYield
With triethylamine In water at 130℃; for 0.333333h; Microwave irradiation;98%
With potassium carbonate In acetone at 50 - 56℃; Williamson reaction;78%
4-[3-(4-amino-3-methylphenyl)pentan-3-yl]-2-methylphenol
863408-16-6

4-[3-(4-amino-3-methylphenyl)pentan-3-yl]-2-methylphenol

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-{4-[3-(4-amino-3-methylphenyl)pentan-3-yl]-2-methylphenoxy}-3,3-dimethylbutan-2-one
853404-33-8

1-{4-[3-(4-amino-3-methylphenyl)pentan-3-yl]-2-methylphenoxy}-3,3-dimethylbutan-2-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 1h;97%
With sodium hydride In N,N-dimethyl-formamide for 21h;97%
5-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]-3-methylthiophene-2-sulfonic acid dimethylaminemethyleneamide

5-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]-3-methylthiophene-2-sulfonic acid dimethylaminemethyleneamide

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

5-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-3-methylthiophene-2-sulfonic acid dimethylaminemethyleneamide

5-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-3-methylthiophene-2-sulfonic acid dimethylaminemethyleneamide

Conditions
ConditionsYield
With potassium carbonate In butanone Heating / reflux;97%
5-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-3-methyl-thiophene-2-sulfonic acid dimethylaminemethyleneamide

5-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-3-methyl-thiophene-2-sulfonic acid dimethylaminemethyleneamide

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

5-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-sulfonic acid dimethylaminemethyleneamide

5-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-sulfonic acid dimethylaminemethyleneamide

Conditions
ConditionsYield
With potassium carbonate In butanone Heating / reflux;97%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

5-(4-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one
59719-19-6

5-(4-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one

3-(4-chlorophenyl)-l-(3, 3-dimethyl-2-oxobutyl)-4, 5-dihydropyrazol-5-one
181067-65-2

3-(4-chlorophenyl)-l-(3, 3-dimethyl-2-oxobutyl)-4, 5-dihydropyrazol-5-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile97%
(R)-(-)-1-(2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-[3-(1-methyl-1-tert-butoxycarbonyl)ethylphenyl]urea
252209-94-2

(R)-(-)-1-(2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-[3-(1-methyl-1-tert-butoxycarbonyl)ethylphenyl]urea

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

(R)-(-)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-[3-(1-methyl-1-tert-butoxycarbonyl)ethylphenyl]urea

(R)-(-)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-[3-(1-methyl-1-tert-butoxycarbonyl)ethylphenyl]urea

Conditions
ConditionsYield
Stage #1: (R)-(-)-1-(2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-[3-(1-methyl-1-tert-butoxycarbonyl)ethylphenyl]urea With sodium hydride In N,N-dimethyl-formamide for 1h;
Stage #2: 1-chloro-3,3-dimethyl-butan-2-one In N,N-dimethyl-formamide at 20℃; for 1.5h;
97%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-hydroxy-3,3-dimethylbutan-2-one
38895-88-4

1-hydroxy-3,3-dimethylbutan-2-one

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water at 40 - 60℃; Reagent/catalyst;97%
With sodium hydroxide In water at 110℃; for 2h; Reagent/catalyst; Solvent;89%
3,5-dimethoxyphenol
500-99-2

3,5-dimethoxyphenol

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-(3',5'-dimethoxyphenoxy)pinacolone

1-(3',5'-dimethoxyphenoxy)pinacolone

Conditions
ConditionsYield
With potassium hydrogencarbonate; sodium iodide In butanone Heating;96%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

methyl (E)-3-(5-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-3-methylthiophen-2-yl)acrylate
1445853-98-4

methyl (E)-3-(5-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-3-methylthiophen-2-yl)acrylate

methyl (E)-3-(5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-3-methylthiophen-2-yl)acrylate
1445853-99-5

methyl (E)-3-(5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-3-methylthiophen-2-yl)acrylate

Conditions
ConditionsYield
With potassium carbonate Inert atmosphere;95%
sodium cyanide
773837-37-9

sodium cyanide

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With sodium carbonate; sodium iodide In methanol at 60℃; for 3h;95%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-(1,2,4-triazole)-yl-3,3-dimethyl-2-butanone

1-(1,2,4-triazole)-yl-3,3-dimethyl-2-butanone

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 50℃; for 5h;95%
methyl 2-(7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate
433703-81-2

methyl 2-(7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

methyl [4,8-dimethyl-7-(3',3'-dimethyl-2'-oxobutoxy)-2-oxo-2H-benzopyran-3-yl]-acetate
664365-86-0

methyl [4,8-dimethyl-7-(3',3'-dimethyl-2'-oxobutoxy)-2-oxo-2H-benzopyran-3-yl]-acetate

Conditions
ConditionsYield
With triethylamine In water at 130℃; for 0.333333h; Microwave irradiation;94%
With potassium carbonate In acetone at 50 - 56℃; Williamson reaction;81%
2-methyl-1,3,4-oxadiazol-5(4H)-one
3069-67-8

2-methyl-1,3,4-oxadiazol-5(4H)-one

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

5-methyl-3-(3,3-dimethyl-2-oxo-butyl)-3H-1,3,4-oxadiazol-2-one

5-methyl-3-(3,3-dimethyl-2-oxo-butyl)-3H-1,3,4-oxadiazol-2-one

Conditions
ConditionsYield
Stage #1: 2-methyl-1,3,4-oxadiazol-5(4H)-one With sodium methylate In methanol at 20℃; for 0.25h;
Stage #2: 1-chloro-3,3-dimethyl-butan-2-one; tetrabutylammomium bromide In chloroform at 20℃; Heating / reflux;
94%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

sodium thiocyanate

sodium thiocyanate

C7H13NOS

C7H13NOS

Conditions
ConditionsYield
In methanol at 55℃; for 2.5h; Product distribution / selectivity;94%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

sodium thiocyanide
540-72-7

sodium thiocyanide

3,3-dimethyl-2-oxobutyl thiocyanate
57518-71-5

3,3-dimethyl-2-oxobutyl thiocyanate

Conditions
ConditionsYield
In methanol at 55℃; for 2.5h;94%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

methyl 3-(3-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-1-methyl-1H-indol-6-yl)propanoate
1445854-13-6

methyl 3-(3-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-1-methyl-1H-indol-6-yl)propanoate

methyl 3-(3-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-methyl-1H-indol-6-yl)propanoate
1445854-14-7

methyl 3-(3-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-methyl-1H-indol-6-yl)propanoate

Conditions
ConditionsYield
With potassium carbonate Inert atmosphere;94%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

5-hydroxy-2,2,5,6,6-pentamethylheptan-3-one
3205-30-9

5-hydroxy-2,2,5,6,6-pentamethylheptan-3-one

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at -78℃; for 2.41667h; Reformatsky type reaction; Inert atmosphere;93%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

1-tert-butylimidazole
45676-04-8

1-tert-butylimidazole

1-(tert-butyl)-3-(3,3-dimethyl-2-oxobutyl)imidazolium chloride
1266108-71-7

1-(tert-butyl)-3-(3,3-dimethyl-2-oxobutyl)imidazolium chloride

Conditions
ConditionsYield
In toluene for 5h; Inert atmosphere; Schlenk technique; Reflux;93%
In toluene for 24h; Reflux;57%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

4-(3-(4-(benzyloxy)phenyl)pentan-3-yl)-2-methylphenol
1445854-37-4

4-(3-(4-(benzyloxy)phenyl)pentan-3-yl)-2-methylphenol

1-(4-(3-(4-(benzyloxy)phenyl)pentan-3-yl)-2-methylphenoxy)-3,3-dimethylbutan-2-one
1445854-38-5

1-(4-(3-(4-(benzyloxy)phenyl)pentan-3-yl)-2-methylphenoxy)-3,3-dimethylbutan-2-one

Conditions
ConditionsYield
With potassium carbonate Inert atmosphere;93%
With potassium carbonate In acetonitrile for 12h; Reflux;93%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

methyl 2-(benzyloxy)-5-(3-(4-hydroxy-3-methylphenyl)-pentan-3-yl)benzoate
1445854-18-1

methyl 2-(benzyloxy)-5-(3-(4-hydroxy-3-methylphenyl)-pentan-3-yl)benzoate

methyl 2-(benzyloxy)-5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)benzoate
1445854-19-2

methyl 2-(benzyloxy)-5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)benzoate

Conditions
ConditionsYield
With potassium carbonate Inert atmosphere;93%
With potassium carbonate In acetonitrile for 12h; Reflux;93%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

7-hydroxy-3-[2-(4-methoxyphenyl)-1,3-thiazolyl-4-yl]-2H-chromen-2-one

7-hydroxy-3-[2-(4-methoxyphenyl)-1,3-thiazolyl-4-yl]-2H-chromen-2-one

7-(3,3-dimethyl-2-oxobutoxy)-3-[2-(4-methoxyphenyl)-1,3-thiazolyl-4-yl]-2-oxo-2H-chromen-7-yl acetate

7-(3,3-dimethyl-2-oxobutoxy)-3-[2-(4-methoxyphenyl)-1,3-thiazolyl-4-yl]-2-oxo-2H-chromen-7-yl acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone Williamson Ether Synthesis; Heating;93%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

2-(N-benzyl-N-methylamino)-3,3-dimethyl-2-butanone
877869-93-7

2-(N-benzyl-N-methylamino)-3,3-dimethyl-2-butanone

Conditions
ConditionsYield
In 1,2-dimethoxyethane Heating;92%

13547-70-1Relevant articles and documents

Fahey,Zuech

, p. 3276 (1974)

Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH

Chen, Zizhan,Zhou, Bin,Cai, Huihua,Zhu, Wei,Zou, Xinzhuo

experimental part, p. 275 - 278 (2010/04/22)

New processes that can selectively prepare α-mono or α,α-dichloro ketones and β-ketoesters using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) are reported. Using silica gel as the catalyst and methanol as the solvent and heating for 1 h under reflux, α-monochlorinated products were selectively obtained in 86-98% yield. However using a deep eutectic solvent (choline chloride: p-TsOH = 1:1) as the solvent and stirring for 45 min at room temperature, α,α- dichlorinated products were selectively obtained in 86-95% yield.

Selective halogenation of ketones

-

Page 3, (2008/06/13)

The present invention provides a process and apparatus for selectively halogenating a ketone of the formula (I) wherein R represents unsubstituted or halogen-substituted C1-C16-alkyl, or aryloxy, R1, R2 and R3 independently represent hydrogen, halogen, C1-C16-alkyl or aryl, the process involving heating the ketone to reflux in a reaction vessel such that the ketone vapor contacts a condensor attached to the reaction vessel and condenses, reacting the condensed ketone with halogen gas, and collecting the selectively halogenated ketone in the reaction vessel.

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