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939-99-1 Usage

Chemical Properties

Colorless to light yellow liqui

Uses

4-(Trifluoromethyl)benzyl chloride may be used in the synthesis of novel series of dithiocarbamates, via reaction with sodium salts of N,N-disubstituted dithiocarbamic acids.

General Description

Electrochemical reduction of 4-(trifluoromethyl)benzyl chloride catalyzed by Co(salen) (H2salen, N,N′-bis(salicylidene)-ethane-1,2-diamine) in acetonitrile is reported.

Check Digit Verification of cas no

The CAS Registry Mumber 939-99-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 9 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 939-99:
(5*9)+(4*3)+(3*9)+(2*9)+(1*9)=111
111 % 10 = 1
So 939-99-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H6ClF3/c9-5-6-1-3-7(4-2-6)8(10,11)12/h1-4H,5H2

939-99-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (B20861)  4-(Trifluoromethyl)benzyl chloride, 98%   

  • 939-99-1

  • 1g

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (B20861)  4-(Trifluoromethyl)benzyl chloride, 98%   

  • 939-99-1

  • 5g

  • 819.0CNY

  • Detail
  • Alfa Aesar

  • (B20861)  4-(Trifluoromethyl)benzyl chloride, 98%   

  • 939-99-1

  • 25g

  • 3693.0CNY

  • Detail

939-99-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Trifluoromethylbenzyl chloride

1.2 Other means of identification

Product number -
Other names 1-(chloromethyl)-4-(trifluoromethyl)benzene

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:939-99-1 SDS

939-99-1Synthetic route

4-methylbenzotrifluoride
6140-17-6

4-methylbenzotrifluoride

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 16h; Time; Sealed tube; Inert atmosphere;87%
With hypochlorous anhydride In tetrachloromethane at 25℃; relative rate constant;
4-(trifluoromethyl)benzylic alcohol
349-95-1

4-(trifluoromethyl)benzylic alcohol

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 70℃; for 1.08333h;86.7%
With 1-pyrrolidinecarboxaldehyde; benzoyl chloride In 1,4-dioxane at 20℃; for 24h; Sealed tube;85%
With tetra-(n-butyl)ammonium iodide; 1,2-dichloro-ethane; triphenylphosphine at 120℃; for 0.5h; Sealed tube; Inert atmosphere;82%
4-(trifluoromethyl)benzylic alcohol
349-95-1

4-(trifluoromethyl)benzylic alcohol

Benzotrichlorid
98-07-7

Benzotrichlorid

A

benzylidene dichloride
98-87-3

benzylidene dichloride

B

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
With TOP; phenylsilane In neat (no solvent) at 100℃; for 24h; Appel Halogenation; Inert atmosphere;A n/a
B 69%
4-trifluoromethylbenzoic acid
455-24-3

4-trifluoromethylbenzoic acid

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
With gallium(III) trichloride; Hexamethyldisiloxane; copper dichloride In 1,2-dichloro-ethane at 20℃; for 5h; Sealed tube; Inert atmosphere;33%
Multi-step reaction with 2 steps
1: LiAlH4 / diethyl ether
2: SOCl2
View Scheme
Multi-step reaction with 2 steps
1: LiAlH4
2: SOCl2
View Scheme
1-(1-Chloro-2,2,2-trifluoro-ethyl)-4-fluoro-benzene
81577-13-1

1-(1-Chloro-2,2,2-trifluoro-ethyl)-4-fluoro-benzene

C8H6F3(1+)
109418-80-6

C8H6F3(1+)

A

C8H5F4(1+)
128408-32-2

C8H5F4(1+)

B

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
at 69.85℃; Thermodynamic data; chloride-transfer;
C9H6ClF3O

C9H6ClF3O

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 25℃; Kinetics;
4-(trifluoromethyl)benzylic alcohol
349-95-1

4-(trifluoromethyl)benzylic alcohol

A

bis(p-trifluoromethylbenzyl) sulfite
1396318-77-6

bis(p-trifluoromethylbenzyl) sulfite

B

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
With pyridine; thionyl chloride In dichloromethaneA 8.8 %Spectr.
B 5.8 %Spectr.
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C
2: thionyl chloride / 1.08 h / 0 - 70 °C
View Scheme
1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-(4-(trifluoromethyl)benzyl)-4-aza-1-azonia-bicyclo[2.2.2]octane chloride

1-(4-(trifluoromethyl)benzyl)-4-aza-1-azonia-bicyclo[2.2.2]octane chloride

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;100%
In tetrahydrofuran at 20℃; for 12h;92%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

C61H57F9N2O6(2+)*2Cl(1-)

C61H57F9N2O6(2+)*2Cl(1-)

Conditions
ConditionsYield
With triethylhexadecylammonium chloride In water at 200℃; for 0.1h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;97.11%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

2-hydroxy-4-(methoxymethyloxy)benzaldehyde
95332-26-6

2-hydroxy-4-(methoxymethyloxy)benzaldehyde

4-methoxymethoxy-2-[4-(trifluoromethyl)benzyloxy]benzaldehyde
1257999-32-8

4-methoxymethoxy-2-[4-(trifluoromethyl)benzyloxy]benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h;96%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

phenol
108-95-2

phenol

1-(phenoxymethyl)-4-(trifluoromethyl)benzene
19962-24-4

1-(phenoxymethyl)-4-(trifluoromethyl)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone94.2%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-(4-methoxybenzyl)-4-(trifluoromethyl)-benzene

1-(4-methoxybenzyl)-4-(trifluoromethyl)-benzene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); 1,3-bis(diphenylphosphino)-1H-indole; sodium hydroxide In N,N-dimethyl acetamide at 120℃; for 6h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;94%
With C36H49Cl2N3Pd; sodium t-butanolate In ethanol at 50℃; for 1h; Suzuki-Miyaura Coupling; Sealed tube;70 %Chromat.
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

4-(2-(diphenylmethoxy)ethyl]piperidine
204064-81-3

4-(2-(diphenylmethoxy)ethyl]piperidine

4-[2-(diphenylmethoxy)ethyl]-1-[((4-trifluoromethyl)phenyl)methyl]piperidine
333363-98-7

4-[2-(diphenylmethoxy)ethyl]-1-[((4-trifluoromethyl)phenyl)methyl]piperidine

Conditions
ConditionsYield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 65℃;92%
With potassium carbonate; triethylamine In DMF (N,N-dimethyl-formamide)92%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-(4-bromophenyl)-1H-tetrazole-5-thiol
22347-29-1

1-(4-bromophenyl)-1H-tetrazole-5-thiol

1-(4-bromo-phenyl)-5-(4-trifluoromethyl-benzylsulfanyl)-1H-tetrazole

1-(4-bromo-phenyl)-5-(4-trifluoromethyl-benzylsulfanyl)-1H-tetrazole

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In toluene Heating;92%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

4-benzoxy-salicylaldehyde
52085-14-0

4-benzoxy-salicylaldehyde

4-benzyloxy-2-[4-(trifluoromethyl)benzyloxy]benzaldehyde
1257999-13-5

4-benzyloxy-2-[4-(trifluoromethyl)benzyloxy]benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h;92%
Pentafluorobenzene
363-72-4

Pentafluorobenzene

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1,2,3,4,5-pentafluoro-6-(4-(trifluoromethyl)benzyl)benzene
1234340-47-6

1,2,3,4,5-pentafluoro-6-(4-(trifluoromethyl)benzyl)benzene

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; triphenylphosphine; Trimethylacetic acid In toluene at 140℃; for 12h; Inert atmosphere;91%
N-methylacetohydroxamic acid
13115-24-7

N-methylacetohydroxamic acid

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

N-methyl-N-((4-(trifluoromethyl)benzyl)oxy)acetamide
1352918-97-8

N-methyl-N-((4-(trifluoromethyl)benzyl)oxy)acetamide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;91%
1-(2-hydroxyphenyl)-imidazole
10041-04-0

1-(2-hydroxyphenyl)-imidazole

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

C17H14F3N2O(1+)*Cl(1-)

C17H14F3N2O(1+)*Cl(1-)

Conditions
ConditionsYield
In acetonitrile for 4h; Reflux;91%
carbon dioxide
124-38-9

carbon dioxide

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

A

4-methylbenzotrifluoride
6140-17-6

4-methylbenzotrifluoride

B

4-Trifluoromethylphenylacetic acid
32857-62-8

4-Trifluoromethylphenylacetic acid

Conditions
ConditionsYield
With salcomine; tetrabutylammonium perchlorate; water In acetonitrile at 25℃; electrochemical reaction;A 90.5%
B 3.3%
With salcomine; tetrabutylammonium perchlorate In acetonitrile at 25℃; electrochemical reaction;A 13.8%
B 84.3%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

2-mercapto-5-methylbenzimidazole
27231-36-3

2-mercapto-5-methylbenzimidazole

6-methyl-2-(4-trifluoromethyl-benzylsulfanyl)-1H-benzoimidazole

6-methyl-2-(4-trifluoromethyl-benzylsulfanyl)-1H-benzoimidazole

Conditions
ConditionsYield
Stage #1: 2-mercapto-5-methylbenzimidazole With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 4-trifluoromethylbenzyl chloride In methanol; N,N-dimethyl-formamide at 20℃;
90%
1-(4-methylphenyl)tetrazole-5-thiol
13980-77-3

1-(4-methylphenyl)tetrazole-5-thiol

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-p-tolyl-5-(4-trifluoromethyl-benzylsulfanyl)-1H-tetrazole

1-p-tolyl-5-(4-trifluoromethyl-benzylsulfanyl)-1H-tetrazole

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In toluene Heating;90%
3-[2-hydroxy-4-(2-methoxyethoxy)phenyl]propanoic acid ethyl ester
888740-22-5

3-[2-hydroxy-4-(2-methoxyethoxy)phenyl]propanoic acid ethyl ester

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

3-(4-(2-methoxyethoxy)-2-{[4-(trifluoromethyl)benzyl]oxy}phenyl)propanoic acid ethyl ester
888740-72-5

3-(4-(2-methoxyethoxy)-2-{[4-(trifluoromethyl)benzyl]oxy}phenyl)propanoic acid ethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide90%
Stage #1: 3-[2-hydroxy-4-(2-methoxyethoxy)phenyl]propanoic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide for 0.5h;
Stage #2: 4-trifluoromethylbenzyl chloride In N,N-dimethyl-formamide for 2h;
90%
C11H15F2NO2

C11H15F2NO2

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

4-(2,2-difluoroethylamino)-3-[4-(trifluoromethyl)benzyl]-1-oxaspiro[4.5]dec-3-en-2-one

4-(2,2-difluoroethylamino)-3-[4-(trifluoromethyl)benzyl]-1-oxaspiro[4.5]dec-3-en-2-one

Conditions
ConditionsYield
Stage #1: C11H15F2NO2 With caesium carbonate In acetonitrile at 0 - 20℃; for 4h;
Stage #2: 4-trifluoromethylbenzyl chloride In acetonitrile for 12h; Reflux; regioselective reaction;
89%
anthranil
271-58-9

anthranil

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

molybdenum hexacarbonyl
13939-06-5, 199620-15-0

molybdenum hexacarbonyl

3-(4-(trifluoromethyl)phenyl)quinolin-2(1H)-one

3-(4-(trifluoromethyl)phenyl)quinolin-2(1H)-one

Conditions
ConditionsYield
With water; palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine In 1,2-dimethoxyethane at 100℃; for 26h; Sealed tube; Inert atmosphere;89%
2-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile

2-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-(4-fluorophenyl)-2-(4-trifluoromethylphenyl)-N,N-dimethylethenylamine

1-(4-fluorophenyl)-2-(4-trifluoromethylphenyl)-N,N-dimethylethenylamine

Conditions
ConditionsYield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 5 - 30℃; for 2h;88.3%
allylmagnesium bromide
2622-05-1

allylmagnesium bromide

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-(but-3-en-1-yl)-4-(trifluoromethyl)benzene

1-(but-3-en-1-yl)-4-(trifluoromethyl)benzene

Conditions
ConditionsYield
In diethyl ether for 16h; Condensation; Heating;88%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

N-(4-chloro-2-mercapto-5-methylbenzenesulfonyl)cyanamide dipotassium salt

N-(4-chloro-2-mercapto-5-methylbenzenesulfonyl)cyanamide dipotassium salt

N-{4-chloro-5-methyl-2-[(4-trifluoromethylbenzyl)thio]benzenesulfonyl}cyanamide potassium salt

N-{4-chloro-5-methyl-2-[(4-trifluoromethylbenzyl)thio]benzenesulfonyl}cyanamide potassium salt

Conditions
ConditionsYield
In ethanol at 20℃; for 4h;88%
at 20℃;
piperazine
110-85-0

piperazine

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-(4-trifluoromethylbenzyl)piperazine
107890-32-4

1-(4-trifluoromethylbenzyl)piperazine

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Reflux; Inert atmosphere;88%
In dichloromethane at 0 - 20℃; for 6h;
In dichloromethane at 0℃;
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

N,N-dimethyl (trimethylsilyl)methanamide
479486-96-9

N,N-dimethyl (trimethylsilyl)methanamide

N,N-dimethyl-2-(4-(trifluoromethyl)phenyl)acetamide
869337-11-1

N,N-dimethyl-2-(4-(trifluoromethyl)phenyl)acetamide

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 1h;87%
Thiomorpholine-4-carbodithioate sodium salt

Thiomorpholine-4-carbodithioate sodium salt

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

4-(trifluoromethyl)benzyl thiomorpholine-4-carbodithioate
1498922-64-7

4-(trifluoromethyl)benzyl thiomorpholine-4-carbodithioate

Conditions
ConditionsYield
In acetone at 20℃; for 3h;87%
2-phenylpropane-1, 3-diol
1570-95-2

2-phenylpropane-1, 3-diol

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

(S)-2-phenyl-3-(p-trifluoromethylbenzyloxy)propan-1-ol

(S)-2-phenyl-3-(p-trifluoromethylbenzyloxy)propan-1-ol

Conditions
ConditionsYield
With (R)-2,4-dimethyl-7-(2-(trityloxy)naphthalen-1-yl)-5H-benzo[c]naphtho[2,3-e][1,2]oxaborinin-5-ol; potassium carbonate; potassium iodide In acetonitrile at 20℃; for 24h; Sealed tube; enantioselective reaction;87%
2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

2-((4-(trifluoromethyl)benzyl)thio)benzo[d]thiazole
758716-82-4

2-((4-(trifluoromethyl)benzyl)thio)benzo[d]thiazole

Conditions
ConditionsYield
With potassium hydroxide In water at 50℃; for 0.5h; Sealed tube; Green chemistry;86%
With potassium carbonate In water at 50℃; for 0.5h; Solvent; Sealed tube; Green chemistry;
1-benzyl-4-(4-fluorophenyl)piperidin-3-one oxime
1280635-01-9

1-benzyl-4-(4-fluorophenyl)piperidin-3-one oxime

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

(Z)-1-benzyl-4-(4-fluorophenyl)piperidin-3-one O-4-trifluoromethylbenzyl oxime
1280635-08-6

(Z)-1-benzyl-4-(4-fluorophenyl)piperidin-3-one O-4-trifluoromethylbenzyl oxime

Conditions
ConditionsYield
Stage #1: 1-benzyl-4-(4-fluorophenyl)piperidin-3-one oxime With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 4-trifluoromethylbenzyl chloride In N,N-dimethyl-formamide at 50℃; for 120h;
85%
sodium N-morpholinocarbamodithioate
873-58-5

sodium N-morpholinocarbamodithioate

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

4-(trifluoromethyl)benzyl morpholine-4-carbodithioate
1498922-66-9

4-(trifluoromethyl)benzyl morpholine-4-carbodithioate

Conditions
ConditionsYield
In acetone at 20℃; for 3h;85%
2-(3-methoxyphenyl)-5, 5-dimethyl-1,3,2-dioxaborinane
1003858-50-1

2-(3-methoxyphenyl)-5, 5-dimethyl-1,3,2-dioxaborinane

4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

1-methoxy-3-(4-(trifluoromethyl)benzyl)benzene

1-methoxy-3-(4-(trifluoromethyl)benzyl)benzene

Conditions
ConditionsYield
With 1-methyl-2-azepanone; copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; lithium tert-butoxide at 60℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;85%

939-99-1Relevant articles and documents

Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors

Yan, Yu-Hang,Li, Wenfang,Chen, Wei,Li, Chao,Zhu, Kai-Rong,Deng, Ji,Dai, Qing-Qing,Yang, Ling-Ling,Wang, Zhenling,Li, Guo-Bo

, (2021/11/17)

Production of metallo-β-lactamases (MBLs) in bacterial pathogens is an important cause of resistance to the ‘last-resort’ carbapenem antibiotics. Development of effective MBL inhibitors to reverse carbapenem resistance in Gram-negative bacteria is still needed. We herein report X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives by considering how to engage with the active-site flexible loops and improve penetration into Gram-negative bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallographic analyses. Of the tested ICA inhibitors, 55 displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clinically isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphologic and internal structural changes of bacterial cells after treatment further demonstrated that 55 crossed the outer membrane and reversed the activity of meropenem. Moreover, 55 showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-negative carbapenem resistance.

Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling

Longwitz, Lars,Jopp, Stefan,Werner, Thomas

, p. 7863 - 7870 (2019/06/27)

A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.

Halogenation through Deoxygenation of Alcohols and Aldehydes

Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang

supporting information, p. 3061 - 3064 (2018/05/28)

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

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