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3932-97-6

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3932-97-6 Usage

Chemical Properties

White liquid or solid

Uses

2,4-Dichloro-5-trifluoromethylpyrimidine is a reactant in the preparation of pyrimidine derivatives as inhibitors of gene ALK protein Kinase phosphorylating kinase and as cell proliferation inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 3932-97-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,9,3 and 2 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3932-97:
(6*3)+(5*9)+(4*3)+(3*2)+(2*9)+(1*7)=106
106 % 10 = 6
So 3932-97-6 is a valid CAS Registry Number.
InChI:InChI=1/C5HCl2F3N2/c6-3-2(5(8,9)10)1-11-4(7)12-3/h1H

3932-97-6 Well-known Company Product Price

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  • Alfa Aesar

  • (H31822)  2,4-Dichloro-5-(trifluoromethyl)pyrimidine, 97%   

  • 3932-97-6

  • 250mg

  • 1262.0CNY

  • Detail
  • Alfa Aesar

  • (H31822)  2,4-Dichloro-5-(trifluoromethyl)pyrimidine, 97%   

  • 3932-97-6

  • 1g

  • 3520.0CNY

  • Detail
  • Aldrich

  • (684864)  2,4-Dichloro-5-(trifluoromethyl)pyrimidine  97%

  • 3932-97-6

  • 684864-250MG

  • 645.84CNY

  • Detail
  • Aldrich

  • (684864)  2,4-Dichloro-5-(trifluoromethyl)pyrimidine  97%

  • 3932-97-6

  • 684864-1G

  • 2,123.55CNY

  • Detail

3932-97-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4-Dichloro-5-(trifluoromethyl)pyrimidine

1.2 Other means of identification

Product number -
Other names 2,4-dichloro-5-(trifluoromethyl)pyrimidine

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:3932-97-6 SDS

3932-97-6Synthetic route

5-trifluoromethyluracil
54-20-6

5-trifluoromethyluracil

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

Conditions
ConditionsYield
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate at 85 - 100℃; for 20h;95%
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate In water at 85 - 100℃; for 20.25h;95%
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; phosphoric acid at 85 - 100℃; for 20.25h;95%
trifluoromethyluracil

trifluoromethyluracil

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

Conditions
ConditionsYield
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate at 85 - 100℃; for 20h;95%
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

2,4-dichloro-5-iodopyrimidine
13544-44-0

2,4-dichloro-5-iodopyrimidine

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; Trimethyl borate In dimethyl sulfoxide at 60℃; for 2h; Inert atmosphere;81%
2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine
170911-92-9

4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate
1393900-79-2

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.833333h;
Stage #2: 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 18h;
98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h;
Stage #2: 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 18h;
98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc dibromide In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h;
Stage #2: 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 3h;
72.3%
tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate
170011-57-1

tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate
1383682-52-7

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In cis-1,2-Dichloroethylene; diethyl ether; butan-1-ol at 20℃; for 0.166667h;
Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In cis-1,2-Dichloroethylene; diethyl ether; butan-1-ol at 20℃;
98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃; for 0.166667h;
Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃;
98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere;
Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 24.5h;
88%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere;
Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 24.5h;
88%
2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

tert-butyl (4-aminobenzyl)carbamate
94838-55-8

tert-butyl (4-aminobenzyl)carbamate

tert-butyl 4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzylcarbamate
1073160-22-1

tert-butyl 4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzylcarbamate

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃; for 0.333333h;
Stage #2: tert-butyl (4-aminobenzyl)carbamate With triethylamine at 20℃;
97%
4-[(tert-butyldimethylsilyl)oxy]aniline
111359-74-1

4-[(tert-butyldimethylsilyl)oxy]aniline

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-4-chloro-5-(trifluoromethyl)pyrimidin-2-amine

N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-4-chloro-5-(trifluoromethyl)pyrimidin-2-amine

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc dibromide In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h;
Stage #2: 4-[(tert-butyldimethylsilyl)oxy]aniline With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 20h;
97%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc dibromide In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h;
Stage #2: 4-[(tert-butyldimethylsilyl)oxy]aniline With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 20h;
97%
4-nitro-phenol
100-02-7

4-nitro-phenol

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

4-chloro-2-(4-nitrophenoxyl)-5-trifluoromethyl pyrimidine
1265228-21-4

4-chloro-2-(4-nitrophenoxyl)-5-trifluoromethyl pyrimidine

Conditions
ConditionsYield
With 4-methyl-morpholine In isopropyl alcohol at -5 - 20℃; for 4h;96%
With 4-methyl-morpholine In isopropyl alcohol at -5 - 20℃;90%
In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at -5 - 20℃; for 4h; Product distribution / selectivity;90%
With N-(2-(4-tert-butyl-piperazin-1-yl)-4-methoxyl-5-(6-(1-methyl-1H-indol-3-yl)-pyrimidin-4-ylamino)-phenyl)-acrylamide In isopropyl alcohol for 1h; Cooling with ice;
2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

phenol
108-95-2

phenol

2-chloro-4-phenoxy-5-(trifluoromethyl)pyrimidine

2-chloro-4-phenoxy-5-(trifluoromethyl)pyrimidine

Conditions
ConditionsYield
With potassium carbonate In acetone at 0℃; for 1h;96%
2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

4-chloro-2-methylsulfany l-5-(trifluoromethyl)pyrimidine
919116-36-2

4-chloro-2-methylsulfany l-5-(trifluoromethyl)pyrimidine

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether at 0℃; for 2h;
Stage #2: sodium thiomethoxide In diethyl ether at 0 - 20℃; for 48h;
95%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether at 0℃; for 2h;
Stage #2: sodium thiomethoxide In diethyl ether at 0 - 20℃; for 48h;
95%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether at 0℃; for 2h;
Stage #2: sodium thiomethoxide In diethyl ether at 0 - 25℃; for 48h;
95%
4-chloro-aniline
106-47-8

4-chloro-aniline

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

A

(4-chlorophenyl)-(4-chloro-5-trifluoromethyl-pyrimidin-2-yl)-amine
514842-83-2

(4-chlorophenyl)-(4-chloro-5-trifluoromethyl-pyrimidin-2-yl)-amine

B

C11H6Cl2F3N3
1448795-01-4

C11H6Cl2F3N3

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃;
Stage #2: 4-chloro-aniline With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃;
A 95%
B n/a
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

2,4-bis(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)pyrimidine

2,4-bis(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)pyrimidine

Conditions
ConditionsYield
Stage #1: 2,2,2-trifluoroethanol With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,4-dichloro-5-trifluoromethylpyrimidine In tetrahydrofuran; hexane at -20 - 40℃; for 24.5h; Inert atmosphere;
91%
Stage #1: 2,2,2-trifluoroethanol With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,4-dichloro-5-trifluoromethylpyrimidine In tetrahydrofuran; hexane at -20 - 40℃; for 24.5h; Inert atmosphere;
91%
Stage #1: 2,2,2-trifluoroethanol With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,4-dichloro-5-trifluoromethylpyrimidine In tetrahydrofuran; hexane at 40℃; for 24h;
91%
2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

5-trifluoromethyluracil
54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With acetic acid In water at 110℃; for 5h;90.6%
2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline
304897-49-2

4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl)piperazine-1-carboxylate
1393901-46-6

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h;
Stage #2: 4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃; Cooling with ice;
90%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere;
Stage #2: 4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃;
90%
3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester
875798-79-1

3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

tert-butyl 3-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate
1393900-90-7

tert-butyl 3-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h;
Stage #2: 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 60h;
90%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h;
Stage #2: 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 60h;
90%
tert-butyl 4-(4-amino-2-methylphenyl)-piperidine-1-carboxylate
955369-50-3

tert-butyl 4-(4-amino-2-methylphenyl)-piperidine-1-carboxylate

2,4-dichloro-5-trifluoromethylpyrimidine
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidine-2-yl)amino)-2-methylphenyl)piperidine-1-carboxylate
1383682-55-0

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidine-2-yl)amino)-2-methylphenyl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere;
Stage #2: tert-butyl 4-(4-amino-2-methylphenyl)-piperidine-1-carboxylate With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 16.5h;
89%

3932-97-6Downstream Products

3932-97-6Relevant articles and documents

Method for preparing 5-trifluoromethyl uracil

-

Paragraph 0036-0037, (2019/06/05)

The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing 5-trifluoromethyl uracil. The method comprises the following steps: firstly, carrying out chlorination reaction on 5-iodouracil and phosphorus oxychloride, thus obtaining 2,4-dichloro-5-iodopyrimidine; secondly, carrying out trifluoromethylation reaction on the 2,4-dichloro-5-iodopyrimidineand a trifluoromethylating reagent, thus obtaining 2,4-dichloro-5-trifluoromethylpyrimidine; finally, enabling the 2,4-dichloro-5-trifluoromethylpyrimidine to react with acetic acid, thus obtaining aproduct. According to the method disclosed by the invention, since chlorination reaction, trifluoromethylation reaction and hydrolysis reaction are adopted, a key intermediate-trifluoromethyl uracil of trifluorothymidine is synthesized in high yield, low cost and low pollution.

Trifluoroethoxy group as a leaving group for regioselective sequential substitution reactions of 5-trifluoromethylpyrimidine derivative with heteroatom nucleophiles

Kagawa, Takumi,Shigehiro, Daiki,Kawada, Kosuke

, p. 150 - 158 (2015/11/10)

Highly regioselective substitution reaction of 2,4-bis(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)pyrimidine (TFEFP) with aniline derivatives smoothly proceeded firstly at the 2-postion. For the subsequent nucleophilic substitution at the 4-position with alkoxides, trifluoroethoxy group at the 4-position serves as a practically efficient leaving group.

SYNTHESIS OF 2,4-DICHLORO-5-TRIFLUOROMETHYL-PYRIMIDINE

-

Paragraph 0060; 0061; 0062; 0063; 0064, (2014/05/20)

This invention relates to a novel method for the synthesis of 2,4-dichloro-5-trifluoromethyl-pyrimidine useful as intermediate in the manufacture of pharmaceutically active ingredients.

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