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Methyl 2-bromobenzoate is an organic compound that features a bromo substituent on the benzene ring and a methyl ester group. It is a versatile intermediate in various chemical reactions and synthesis processes.

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  • 610-94-6 Structure
  • Basic information

    1. Product Name: Methyl 2-bromobenzoate
    2. Synonyms: RARECHEM AL BF 0014;2-BROMOBENZOIC ACID METHYL ESTER;METHYL 2-BROMOBENZOATE;METHYL O-BROMOBENZOATE;2-bromo-benzoicacimethylester;Benzoicacid,2-bromo-,methylester;O-bromobenzoic acid, methyl ester;Methyl2-bromobenzoate,99%
    3. CAS NO:610-94-6
    4. Molecular Formula: C8H7BrO2
    5. Molecular Weight: 215.04
    6. EINECS: 210-241-5
    7. Product Categories: Aromatic Esters;Acids & Esters;Bromine Compounds;C8 to C9;Carbonyl Compounds;Esters
    8. Mol File: 610-94-6.mol
    9. Article Data: 72
  • Chemical Properties

    1. Melting Point: 252°C
    2. Boiling Point: 252 °C(lit.)
    3. Flash Point: >230 °F
    4. Appearance: Clear light yellow/Liquid
    5. Density: 1.532 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0368mmHg at 25°C
    7. Refractive Index: n20/D 1.559(lit.)
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. Water Solubility: insoluble
    11. BRN: 1862501
    12. CAS DataBase Reference: Methyl 2-bromobenzoate(CAS DataBase Reference)
    13. NIST Chemistry Reference: Methyl 2-bromobenzoate(610-94-6)
    14. EPA Substance Registry System: Methyl 2-bromobenzoate(610-94-6)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 610-94-6(Hazardous Substances Data)

610-94-6 Usage

Uses

Used in Organic Synthesis:
Methyl 2-bromobenzoate is used as a key intermediate for the synthesis of various organic compounds. Its reactivity and functional groups make it suitable for a wide range of reactions, including cross-coupling and Heck reactions.
Used in Pharmaceuticals:
In the pharmaceutical industry, Methyl 2-bromobenzoate is used as a building block for the development of new drugs. Its unique structure allows for the creation of novel compounds with potential therapeutic applications.
Used in Agrochemicals:
Methyl 2-bromobenzoate is also utilized in the agrochemical sector as a precursor for the synthesis of various agrochemical products, such as pesticides and herbicides. Its versatility in chemical reactions enables the development of new and effective compounds for agricultural use.
For example, under Heck reaction with acrylonitrile, Methyl 2-bromobenzoate undergoes lactonization to give the benzofuran-2-one 3-(cyanomethyl)-2-coumaranone, which is an important raw material and intermediate in the synthesis of pharmaceuticals and agrochemicals.

Purification Methods

A solution of the ester in ether is washed with 10% aqueous Na 2CO3, water, then dried and distilled. [Beilstein 9

Check Digit Verification of cas no

The CAS Registry Mumber 610-94-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 0 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 610-94:
(5*6)+(4*1)+(3*0)+(2*9)+(1*4)=56
56 % 10 = 6
So 610-94-6 is a valid CAS Registry Number.

610-94-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A12435)  Methyl 2-bromobenzoate, 99%   

  • 610-94-6

  • 25g

  • 323.0CNY

  • Detail
  • Alfa Aesar

  • (A12435)  Methyl 2-bromobenzoate, 99%   

  • 610-94-6

  • 100g

  • 1216.0CNY

  • Detail
  • Alfa Aesar

  • (A12435)  Methyl 2-bromobenzoate, 99%   

  • 610-94-6

  • 500g

  • 5454.0CNY

  • Detail

610-94-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 2-bromobenzoate

1.2 Other means of identification

Product number -
Other names methyl bromobenzoate

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:610-94-6 SDS

610-94-6Synthetic route

methanol
67-56-1

methanol

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid Reflux; Inert atmosphere;99%
With sulfuric acid Reflux;99%
With sulfuric acid at 0℃; for 20.25h; Fischer-Speier Esterification; Reflux;96%
methanol
67-56-1

methanol

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With perchloric acid; sodium percarbonate; vanadia for 1.3h; Cooling;96%
With tert.-butylhydroperoxide; potassium carbonate In water at 60℃; for 6h;87%
With magnesium hydroxide; oxygen at 90℃; under 2250.23 Torr; for 8h;
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

o-bromophenyl acetate
1829-37-4

o-bromophenyl acetate

Conditions
ConditionsYield
With hydrogenchloride In chloroform at 20℃; for 12h; Baeyer-Villiger oxidation;A 7%
B 91%
2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

methyl salicylate
119-36-8

methyl salicylate

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
Stage #1: 2-bromobenzoic-acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h;
Stage #2: methyl salicylate at 110℃; for 24h;
A 91%
B n/a
methanol
67-56-1

methanol

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h;86%
With potassium chloride; dihydrogen peroxide; C5H12CrMo6O25(3-)*3C16H36N(1+) In water at 65℃; for 36h; Schlenk technique;80%
With sodium hypochlorite; tetrabutylammomium bromide In ethyl acetate at 20℃; for 3.51667h;17%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 25℃; for 12h; Temperature; chemoselective reaction;24 %Chromat.
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 4%
B 85%
C 3%
carbon monoxide
201230-82-2

carbon monoxide

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 4%
B 85%
C 3%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid In methanol84%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: tert.-butylhydroperoxide; 2-methylphenyl bromide In water; dimethyl sulfoxide
Stage #2: In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube;
84%
With copper (II)-fluoride In water; dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry;25%
With ultrafine CuO particles dispersed on nitrogen-doped hollow carbon nanospheres In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube;86 %Chromat.
1-bromo-2-(methoxymethyl)benzene
52711-30-5

1-bromo-2-(methoxymethyl)benzene

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With oxygen In water at 25℃; for 12h; Irradiation; Green chemistry;80%
With copper(II) choride dihydrate; oxygen; hydroquinone at 30℃; for 16h; Sealed tube; Irradiation; Green chemistry;41%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With N-Bromosuccinimide; silver hexafluoroantimonate; trifluorormethanesulfonic acid; nickel diacetate In 1,2-dichloro-ethane at 80℃; for 12h; regioselective reaction;76%
Stage #1: benzoic acid methyl ester With acetic acid
Stage #2: With bromine; acetic acid at 0 - 25℃; for 12h;
66.9%
With N-Bromosuccinimide; dibenzoyl peroxide
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With copper (II)-fluoride In water; dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry;72%
With tetraethylammonium bromide; oxygen; potassium carbonate In water; dimethyl sulfoxide at 100℃; under 735.576 Torr; for 16h; Catalytic behavior; Mechanism;71%
methanol
67-56-1

methanol

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; under 11251.1 Torr; continuous flow reactor;69%
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; hydrazine In tetrahydrofuran; 1,4-dioxane at 100℃; under 11251.1 Torr; Flow reactor;69%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With copper (II)-fluoride In water; dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry;65%
Monomethyl phthalate
4376-18-5

Monomethyl phthalate

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; bromine In various solvent(s) for 22h; bromodecarboxylation; Heating; irradiation;57%
1-thiopropane
107-03-9

1-thiopropane

methyl 2-bromo-3-aminobenzoate
106896-48-4

methyl 2-bromo-3-aminobenzoate

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

methyl 2-bromo-3-propylthiobenzoate

methyl 2-bromo-3-propylthiobenzoate

Conditions
ConditionsYield
Stage #1: methyl 2-bromo-3-aminobenzoate With tert.-butylnitrite; boron trifluoride diethyl etherate In diethyl ether; dichloromethane at -15 - 5℃; Diazotization;
Stage #2: 1-thiopropane With triethylamine In acetonitrile at 80℃; for 18h; Alkylation; substitution; decomposition; deamination;
A n/a
B 38%
methanol
67-56-1

methanol

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With 3,3'-dimethyl-1,1'-(hexane-1,6-diyl)diimidazolium glutarate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-(n-butyl)-3-methylimidazolium triflate In tetrahydrofuran at 55℃; for 16h; Molecular sieve;A 8%
B 37%
With C12H22N6(2+)*2C2F6NO4S2(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 55℃; for 16h; Reagent/catalyst; Molecular sieve;A 25%
B 17%
With C14H22N2S2(2+)*2F6P(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 55℃; for 16h; Reagent/catalyst; Molecular sieve;A 8%
B 21%
methanol
67-56-1

methanol

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With carbon tetrabromide; oxygen for 24h; Irradiation;34%
methanol
67-56-1

methanol

2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

bromobenzene
108-86-1

bromobenzene

Methyl-tert.-butylperoxyoxalat
57031-51-3

Methyl-tert.-butylperoxyoxalat

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
In benzene Heating;
sodium acetoacetonate
15435-71-9

sodium acetoacetonate

copper(I) 2-bromobenzoate
121619-96-3

copper(I) 2-bromobenzoate

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

C

diphenic acid dimethyl ester
5807-64-7

diphenic acid dimethyl ester

D

3-(o-methoxycarbonylphenyl)pentane-2,4-dione
56741-51-6

3-(o-methoxycarbonylphenyl)pentane-2,4-dione

Conditions
ConditionsYield
1.) toluene, 1 h, 80 deg C; 2.) diethyl ether; Yield given. Multistep reaction. Yields of byproduct given;
Mechanism; Product distribution;
mesitylcopper(I)
75732-01-3

mesitylcopper(I)

copper(I) 2-bromobenzoate
121619-96-3

copper(I) 2-bromobenzoate

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

Mesityl 2-bromobenzoate
128499-36-5

Mesityl 2-bromobenzoate

C

Mesityl 2-mesitylbenzoate
128499-34-3

Mesityl 2-mesitylbenzoate

D

Mesityl methyl biphenyl-2,2'-dicarboxylate
128499-37-6

Mesityl methyl biphenyl-2,2'-dicarboxylate

Conditions
ConditionsYield
With oxygen 1.) toluene, 30 min, roomtemp.; 2.) 2 h, 80 deg C; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;
sodium methylate
124-41-4

sodium methylate

1-(2-bromobenzoyl)-3-(4-chlorophenyl)urea
107485-55-2

1-(2-bromobenzoyl)-3-(4-chlorophenyl)urea

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

N-(4-chlorophenyl)urea
140-38-5

N-(4-chlorophenyl)urea

Conditions
ConditionsYield
In methanol at 25℃; Kinetics; Mechanism; Rate constant;
1-thiopropane
107-03-9

1-thiopropane

C8H6BrN2O2(1+)*BF4(1-)

C8H6BrN2O2(1+)*BF4(1-)

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

methyl 2-bromo-3-propylthiobenzoate

methyl 2-bromo-3-propylthiobenzoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 80℃; for 18h; Alkylation; substitution; decomposition;A n/a
B 1.10 g
methyl iodide
74-88-4

methyl iodide

2-bromo-benzoate silver

2-bromo-benzoate silver

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

2-bromo-3-nitro-benzoic acid
573-54-6

2-bromo-3-nitro-benzoic acid

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: PCl5 / 0.08 h / 150 °C
1.2: 94 percent / 1 h / Heating
2.1: 87 percent / glacial acetic acid; iron / 2 h / 120 °C
3.1: 91 percent / BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
4.1: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1.1: PCl5 / 0.08 h / 150 °C
1.2: 94 percent / 1 h / Heating
2.1: 87 percent / glacial acetic acid; iron / 2 h / 120 °C
3.1: BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
3.2: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
2-bromo-3-nitro-benzoic acid methyl ester
5337-09-7

2-bromo-3-nitro-benzoic acid methyl ester

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / glacial acetic acid; iron / 2 h / 120 °C
2: 91 percent / BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
3: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 87 percent / glacial acetic acid; iron / 2 h / 120 °C
2.1: BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
2.2: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
methyl 2-bromo-3-aminobenzoate
106896-48-4

methyl 2-bromo-3-aminobenzoate

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
2: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
anhydro-2-hydroxymercuri-3-nitrobenzoic acid

anhydro-2-hydroxymercuri-3-nitrobenzoic acid

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: bromine; base
2.1: PCl5 / 0.08 h / 150 °C
2.2: 94 percent / 1 h / Heating
3.1: 87 percent / glacial acetic acid; iron / 2 h / 120 °C
4.1: 91 percent / BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
5.1: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1.1: bromine; base
2.1: PCl5 / 0.08 h / 150 °C
2.2: 94 percent / 1 h / Heating
3.1: 87 percent / glacial acetic acid; iron / 2 h / 120 °C
4.1: BF3*Et2O; t-butyl nitrite / CH2Cl2; diethyl ether / -15 - 5 °C
4.2: triethylamine / acetonitrile / 18 h / 80 °C
View Scheme
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

2-methoxynaphthylamine
2246-42-6

2-methoxynaphthylamine

methyl 2-[(2-methoxy-1-naphthyl)amino]benzoate

methyl 2-[(2-methoxy-1-naphthyl)amino]benzoate

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 20 - 80℃; for 15.525h;100%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 20 - 80℃; for 15.5h; Inert atmosphere;100%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methylmagnesium chloride
676-58-4

methylmagnesium chloride

2-(2-bromophenyl)propanol
7073-69-0

2-(2-bromophenyl)propanol

Conditions
ConditionsYield
Stage #1: 2-bromobenzoic acid methyl ester; methylmagnesium chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 20℃; Cooling with ice;
Stage #2: With hydrogenchloride In tetrahydrofuran; 2-methyltetrahydrofuran; water at 0℃; pH=6; Product distribution / selectivity;
100%
In tetrahydrofuran at 0℃; Inert atmosphere;82%
In tetrahydrofuran at 5 - 20℃; Inert atmosphere;
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 10 - 20℃; for 1.08333h;100%
With iodine; aluminium In acetonitrile at 80℃; for 18h;99%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile) In toluene at 90℃; for 5h;99%
Stage #1: 2-bromobenzoic acid methyl ester With sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -48℃; for 7.77778E-06h;
Stage #2: With methanol In tetrahydrofuran; hexane; cyclohexane at -48℃; for 0.000638889h;
74%
With copper(I) chloride; methanol; sodium tetrahydroborate at 0℃;93 % Chromat.
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

methyl 3’-nitro-[1,1’-biphenyl]-2-carboxylate
83527-96-2

methyl 3’-nitro-[1,1’-biphenyl]-2-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 85℃; Suzuki cross-coupling;99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 20 - 80℃; for 6h; Inert atmosphere;17%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol Suzuki cross-coupling; microwave irradiation;
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2'-methoxy-biphenyl-2-carboxylic acid methyl ester
63506-58-1

2'-methoxy-biphenyl-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; triphenylphosphine; [BMIM][Cl] In water; toluene for 3.5h; Suzuki coupling reaction; Heating;99%
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In ethanol; water; toluene at 78 - 80℃; for 8h; Inert atmosphere;92%
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In water; acetonitrile at 60℃; Suzuki-Miyaura reaction; Inert atmosphere; Sealed vessel;
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate In 1,2-dimethoxyethane at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

N-Methylurea
598-50-5

N-Methylurea

3-methyl-2,4(1H,3H)-quinazolinedione
607-19-2

3-methyl-2,4(1H,3H)-quinazolinedione

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 48h;99%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 24h;61%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

3,4,5-trimethoxyphenylboronic Acid
182163-96-8

3,4,5-trimethoxyphenylboronic Acid

3',4',5'-trimethoxybiphenyl-2-carboxylic acid methyl ester
928847-09-0

3',4',5'-trimethoxybiphenyl-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃;99%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; Suzuki reaction;45%
Octanethiol
111-88-6

Octanethiol

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methyl 2-octylthiobenzenecarboxylate
211228-57-8

methyl 2-octylthiobenzenecarboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;99%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

tri-n-butyl(thien-3-yl)tin
119405-65-1

tri-n-butyl(thien-3-yl)tin

methyl 2-(thiophen-3-yl)benzoate

methyl 2-(thiophen-3-yl)benzoate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Stille Cross Coupling; Reflux; Inert atmosphere;99%
Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methyl 2-(thiophen-3-yl)benzoate

methyl 2-(thiophen-3-yl)benzoate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 70℃; for 16h; Inert atmosphere; Schlenk technique;99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 70℃; for 16h; Suzuki Coupling; Inert atmosphere;98%
With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In tetrahydrofuran; water at 70℃; Suzuki-Miyaura Coupling; Inert atmosphere;92%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 70℃; for 36h; Inert atmosphere; Schlenk technique;89%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

2,4-dichlorophenylboronic acid
68716-47-2

2,4-dichlorophenylboronic acid

2',4'-Dichloro-biphenyl-2-carboxylic acid methyl ester

2',4'-Dichloro-biphenyl-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 120℃; for 3h;99%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

4-(pentafluorosulfanyl)aniline
2993-24-0

4-(pentafluorosulfanyl)aniline

N-(4-(pentafluorosulfanyl)phenyl)anthranilic acid methyl ester

N-(4-(pentafluorosulfanyl)phenyl)anthranilic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;99%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

(E)-3-methoxy-1-propenylboronic acid pinacol ester
165059-42-7

(E)-3-methoxy-1-propenylboronic acid pinacol ester

methyl (E)-2-(3-methoxyprop-1-en-1-yl)benzoate
1255651-89-8

methyl (E)-2-(3-methoxyprop-1-en-1-yl)benzoate

Conditions
ConditionsYield
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In tetrahydrofuran; water at 45℃; for 23h; Inert atmosphere; Sealed tube;99%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

potassium vinyltrifluoroborate

potassium vinyltrifluoroborate

methyl o-vinylbenzoate
27326-44-9

methyl o-vinylbenzoate

Conditions
ConditionsYield
With caesium carbonate; triphenylphosphine; palladium dichloride In tetrahydrofuran; water at 85℃; for 12h; Suzuki Coupling; Inert atmosphere;99%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-(2-bromophenyl)propanol
7073-69-0

2-(2-bromophenyl)propanol

Conditions
ConditionsYield
Stage #1: 2-bromobenzoic acid methyl ester; methylmagnesium bromide In tetrahydrofuran at 20℃; Cooling with ice;
Stage #2: With hydrogenchloride In water pH=5 - 6;
98.2%
Stage #1: 2-bromobenzoic acid methyl ester; methylmagnesium bromide In tetrahydrofuran; diethyl ether at 2 - 15℃; for 19.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 0 - 15℃; for 2h; Product distribution / selectivity;
97.48%
In tetrahydrofuran at 0 - 15℃; Inert atmosphere;97.5%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

N-(3-methylphenyl)anthranilic acid methyl ester
23868-14-6

N-(3-methylphenyl)anthranilic acid methyl ester

Conditions
ConditionsYield
With potassium phosphate; johnphos; tris(dibenzylideneacetone)dipalladium (0) In 1,2-dimethoxyethane at 100℃; for 24h; Arylation;98%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

tributyl(3-methoxyphenyl)stannane
122439-11-6

tributyl(3-methoxyphenyl)stannane

methyl 3'-methoxy-[1,1'-biphenyl]-2-carboxylate

methyl 3'-methoxy-[1,1'-biphenyl]-2-carboxylate

Conditions
ConditionsYield
With lithium chloride; dichlorobis(tris[4-(heptadecafluorooctyl)phenyl]phosphine-kP)palladium In N,N-dimethyl-formamide at 80℃; for 3h; Stille cross-coupling reaction;98%
With carbon dioxide; tetrabutyl-ammonium chloride; [(m-C8H17-C6H4)3P]2*PdCl2 at 90℃; for 24h; Stille coupling;61 % Spectr.
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

phenylacetylene
536-74-3

phenylacetylene

methyl 2-(phenylethynyl)benzoate
33578-05-1

methyl 2-(phenylethynyl)benzoate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira coupling; Inert atmosphere;98%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃; Cooling with liquid nitrogen; Sealed tube;97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h; Sonogashira coupling;96%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

methyl 4'-methylbiphenyl-2-carboxylate
114772-34-8

methyl 4'-methylbiphenyl-2-carboxylate

Conditions
ConditionsYield
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation;98%
With potassium fluoride; palladium diacetate In toluene at 80℃; for 1h; Suzuki-Miyaura coupling;93%
With sodium carbonate; [(PPh3)2Pd(N-succ)2] In tetrahydrofuran; water at 60℃; for 10h; Suzuki cross-coupling reaction;62%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate
375853-82-0, 286961-14-6

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

tert-butyl 4-(2-(methoxycarbonyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

tert-butyl 4-(2-(methoxycarbonyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 140℃; for 0.0833333h; Microwave irradiation;98%
With potassium carbonate; PdCl2*1,1'-bis(diphenylphosphine)ferrocene In N,N-dimethyl-formamide at 90℃; for 5h;
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

tributyl(thien-2-yl)stannane
54663-78-4

tributyl(thien-2-yl)stannane

o-(2-thienyl)benzoic acid methyl ester
17595-84-5

o-(2-thienyl)benzoic acid methyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 17h; Stille coupling; Inert atmosphere; Reflux;98%
3‐methyl‐1‐(2‐methylphenyl)‐1H‐pyrazol‐5‐amine
91331-68-9

3‐methyl‐1‐(2‐methylphenyl)‐1H‐pyrazol‐5‐amine

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

methyl 2-((3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl)amino)benzenecarboxylate
1209485-73-3

methyl 2-((3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl)amino)benzenecarboxylate

Conditions
ConditionsYield
Stage #1: 3‐methyl‐1‐(2‐methylphenyl)‐1H‐pyrazol‐5‐amine; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-bromobenzoic acid methyl ester With caesium carbonate In toluene at 95℃; Inert atmosphere;
98%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16h; Buchwald-Hartwig type cross-coupling; Reflux;
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

acetone
67-64-1

acetone

1-(2-bromophenyl)-butane-1,3-dione
57279-20-6

1-(2-bromophenyl)-butane-1,3-dione

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 100℃; for 18.5h;98%
With sodium hydride In tetrahydrofuran at 20℃; for 18h; Reflux;
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

4-(tert-butylamino)phthalazin-1(2H)-one
1346229-07-9

4-(tert-butylamino)phthalazin-1(2H)-one

Conditions
ConditionsYield
With palladium diacetate; hydrazine hydrate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dimethyl sulfoxide at 150℃; for 0.0833333h; Microwave irradiation; Inert atmosphere; regioselective reaction;98%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

hydrazine
302-01-2

hydrazine

4-(tert-butylamino)phthalazin-1(2H)-one
1346229-07-9

4-(tert-butylamino)phthalazin-1(2H)-one

Conditions
ConditionsYield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dimethyl sulfoxide at 150℃; for 0.0833333h; Inert atmosphere; Microwave irradiation; Sealed tube;98%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

3-pentafluorosulfuraniline
2993-22-8

3-pentafluorosulfuraniline

N-(3-(pentafluorosulfanyl)phenyl)anthranilic acid methyl ester

N-(3-(pentafluorosulfanyl)phenyl)anthranilic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;98%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

(E)-4,4,5,5-tetramethyl-2-(3-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane
177573-86-3

(E)-4,4,5,5-tetramethyl-2-(3-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane

methyl (E)-2-(3-phenylprop-1-en-1-yl)benzoate
1027255-60-2

methyl (E)-2-(3-phenylprop-1-en-1-yl)benzoate

Conditions
ConditionsYield
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In tetrahydrofuran; water at 45℃; for 17h; Inert atmosphere; Sealed tube;98%

610-94-6Relevant articles and documents

POLYCYCLIC AMIDES AS UBE2K MODULATORS FOR TREATING CANCER

-

Paragraph 0078-0080, (2021/07/10)

Provided are compounds of Formula (I) and pharmaceutically acceptable salts and compositions thereof, which are useful for treating conditions associated with modulation of UBE2K.

Antibacterial and Antiviral Activities of 1,3,4-Oxadiazole Thioether 4H-Chromen-4-one Derivatives

Cao, Xiao,Liu, Fang,Liu, Liwei,Liu, Tingting,Peng, Feng,Wang, Qifan,Xie, Chengwei,Xue, Wei,Yang, Jinsong

, p. 11085 - 11094 (2021/10/01)

Various 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives were conceived. The title compounds demonstrated striking inhibitory effects againstXac,Psa, andXoo. EC50data exhibited that A8 (19.7 μg/mL) had better antibacterial activity againstXoothan myricetin, BT, and TC. Simultaneously, the mechanism of action of A8 had been verified by SEM. The results of anti-tobacco mosaic virus indicated that A9 had the bestin vivoantiviral effect compared with ningnanmycin. From the data of MST, it could be seen that A9 (0.003 ± 0.001 μmol/L) exhibited a strong binding capacity, which was far superior to ningnanmycin (2.726 ± 1.301 μmol/L). This study shows that the 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives may become agricultural drugs with great potential.

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Zhou, Wenjuan,Xu, Chenhao,Dong, Guanjun,Qiao, Hui,Yang, Jing,Liu, Hongmin,Ding, Lina,Sun, Kai,Zhao, Wen

, (2021/03/24)

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

Wang, Jingjing,Jiang, Feng,Tao, Chaofu,Yu, Han,Ruhlmann, Laurent,Wei, Yongge

supporting information, p. 2652 - 2657 (2021/04/21)

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

Ultrafine Copper Oxide Particles Dispersed on Nitrogen-Doped Hollow Carbon Nanospheres for Oxidative Esterification of Biomass-Derived 5-Hydroxymethylfurfural

Gupta, Shyam Sunder R.,Vinu, Ajayan,Kantam, Mannepalli Lakshmi

, p. 259 - 269 (2021/03/01)

One-pot synthesis of furan-2,5-dimethylcarboxylate (FDMC) from 5-hydroxymethylfurfural (HMF) is highly demanding for the commercial production of polyethylene furanoate (PEF). Herein, a direct synthesis of FDMC is reported from oxidative esterification of HMF using ultrafine CuO particles dispersed on nitrogen-doped hollow carbon nanospheres (CuO/N?C?HNSs) as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidizing and methylating reagent. The CuO/N?C?HNSs was prepared through a template protection-sacrifice strategy using SiO2 as a sacrificial template and histidine as the precursor for N and C. N-doping facilitated a strong interaction between the support and copper species, affording formation of CuO nanoparticles of less than 10 nm in size. By virtue of the highly dispersed CuO nanoparticles and a high BET surface area 373 m2/g, the CuO/N?C?HNSsshows excellent catalytic performance in the selective conversion of HMF into FDMC affording 93 % yield of the desired product with a TON value of 49. Furthermore, the oxidative esterification involving SP3C?H bond functionalization is also demonstrated using the same catalyst.

Rh-Catalyzed Asymmetric Hydrogenation of α,β- and β,β-Disubstituted Unsaturated Boronate Esters

Hou, Guohua,Shen, Xin,Yan, Qiaozhi,Zi, Guofu

supporting information, (2020/05/08)

A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully transformed to the corresponding chiral alcohols, amines and other important derivatives with maintained enantioselectivities.

DHODH INHIBITORS AND THEIR USE AS ANTIVIRAL AGENTS

-

Page/Page column 56, (2020/11/22)

The present invention relates to a compound, or a dimer or a pharmaceutically acceptable salt or solvate of said compound or dimer, for use in a method for the treatment of a disease, disorder or condition caused by an RNA virus, said compound having the general structure shown in Formula (I).

Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents

Bai, Xue-Qian,Cui, Ming-Yue,Li, Chun-Shi,Liang, Cheng-Wu,Song, Ze-Wen,Wang, Hui-Yan,Zhang, Tian-Yi,Zheng, Xian-Jing

, (2020/05/08)

Twenty benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their anti-oxidant and anti-inflammatory activities. Among these compounds, 8h and 8l were appeared to have high radical scavenging efficacies as 0.05 ± 0.02 and 0.07 ± 0.03 mmol/L of IC50 values in ABTS+[rad] bioassay, respectively. In anti-inflammatory tests, compound 8h displayed good activity with 57.35% inhibition after intraperitoneal administration, which was more potent than the reference drug (indomethacin). Molecular modeling studies were performed to investigate the binding mode of the representative compound 8h into COX-2 enzyme. In vitro enzyme study implied that compound 8h exerted its anti-inflammatory activity through COX-2 inhibition.

Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors

Yuan, Chen,Yan, Jie,Song, Chen,Yang, Fan,Li, Chao,Wang, Cheng,Su, Huiling,Chen, Wei,Wang, Lijiao,Wang, Zhouyu,Qian, Shan,Yang, Lingling

, (2020/01/11)

The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.

Copper-catalyzed oxidative methyl-esterification of 5-hydroxymethylfurfural using TBHP as an oxidizing and methylating reagent: A new approach for the synthesis of furan-2,5-dimethylcarboxylate

Gupta, Shyam Sunder R.,Kantam, Mannepalli Lakshmi,Vinu, Ajayan

, p. 259 - 269 (2020/06/27)

Catalytic conversion of 5-hydroxymethylfurfural (HMF) into furan-2,5-dimethylcarboxylate (FDMC) is of great significance in the production of polyethylene furanoate (PEF), a renewable biomass-derived polymer that can replace the fossil dependent polyethylene terephthalate (PET). Herein, for the first time, we report the synthesis of FDMC from oxidative methyl-esterification of HMF using tert-butyl hydroperoxide (TBHP) as an oxidizing and methylating reagent catalyzed by mesoporous alumina nanospheres-embedded with CuO nanoparticles (CuO/m-Al2O3). The CuO/m-Al2O3 catalysts with different copper contents were prepared by evaporation-induced self-assembly of a structure-directing agent (Pluronic P-123). The decomposition of P-123 during calcination in air results into the formation of a mesoporous structure with highly dispersed CuO nanoparticles. The as-prepared 6-CuO/m-Al2O3 exhibits excellent catalytic activity towards oxidative methyl-esterification of HMF into FDMC with 92% yield and turnover frequency (TOF) of 0.56 h?1. Furthermore, oxidative methyl-esterification of a range of substrates through SP3 C[sbnd]H bond functionalization has also been demonstrated using the same catalyst.

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