610-96-8

Basic information

• Product Name: Methyl 2-chlorobenzoate
• Synonyms: O-CHLOROBENZOIC ACID METHYL ESTER;RARECHEM AL BF 0018;2-chloro-benzoicacimethylester;Benzoic acid, 2-chloro-, methyl ester;Benzoic acid, o-chloro-, methyl ester;2-CHLOROBENZOIC ACID METHYL ESTER;METHYL O-CHLOROBENZOATE;METHYL 2-CHLOROBENZOATE
• CAS NO: 610-96-8
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 210-242-0
• Product Categories: Aromatic Esters;pharmacetical;Benzoic acid;Acids & Esters;Chlorine Compounds;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 610-96-8.mol
• Article Data: 139

Chemical Properties

• Melting Point: 233-235 °C
• Boiling Point: 233-235 °C
• Flash Point: 108 °C
• Appearance: Clear colorless/Liquid
• Density: 1.191 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0868mmHg at 25°C
• Refractive Index: 1.5351-1.537
• Storage Temp.: Store below +30°C.
• BRN: 1364684
• CAS DataBase Reference: Methyl 2-chlorobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-chlorobenzoate(610-96-8)
• EPA Substance Registry System: Methyl 2-chlorobenzoate(610-96-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 610-96-8(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powder

Uses

Methyl 2-chlorobenzoate may be used in the synthesis of various quinazolinone derivatives. It was used as starting reagent in the synthesis of 2-chlorobenzohydrazide.

General Description

Methyl 2-chlorobenzoate, a methyl 2-halobenzoate, is an ester. It can be synthesized from 2-chlorobenzoyl chloride. Its reduction with NaBH4 in diglyme at 162°C affords 2-chlorobenzyl alcohol.

InChI:InChI=1/C8H7ClO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3

Synthetic route

methanol (67-56-1) + ortho-chlorobenzoic acid (118-91-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With sulfuric acid for 4h; Reflux;	100%
With sulfuric acid Heating;	99%
With 1,3,5-trichloro-2,4,6-triazine; sodium carbonate at 50℃; for 0.333333h; Sonication;	94%

tert.-butylhydroperoxide (75-91-2) + 2-chloro-benzaldehyde (89-98-5) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
Stage #1: tert.-butylhydroperoxide; 2-chloro-benzaldehyde In water; dimethyl sulfoxide Stage #2: In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube;	99%

N,N-Diethyl-2-chlorobenzamide (10345-79-6) + trimethoxonium tetrafluoroborate (420-37-1) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
Stage #1: N,N-Diethyl-2-chlorobenzamide; trimethoxonium tetrafluoroborate With disodium hydrogenphosphate In acetonitrile at 20℃; Methylation; Stage #2: With sodium hydrogencarbonate for 18h; Hydrolysis;	98%

2,6-dichlorobenzoic acid methyl ester (14920-87-7) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With methanol; sodium hydroxide In water Electrolysis;	98%

methanol (67-56-1) + 2'-chloro-sec-phenethyl alcohol (13524-04-4) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With N-iodo-succinimide; 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Molecular sieve;	98%
With oxygen; potassium carbonate at 150℃; under 4500.45 Torr; for 24h; Autoclave;	78 %Chromat.

methanol (67-56-1) + 2-chloro-benzaldehyde (89-98-5) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux;	97%
With aluminium(III) chloride hexahydrate; urea hydrogen peroxide adduct at 60℃; Green chemistry;	93%
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide at 20℃; for 5.3h; Reagent/catalyst;	89%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2-iodochlorobenzene (615-41-8) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With C57H43IP2Pd; triethylamine at 90℃; under 3750.38 Torr; for 12h; Autoclave;	97%

methanol (67-56-1) + o-chlorobenzoyl chloride (609-65-4) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With triethylamine at 20℃; for 10h;	95%

N,N-dimethyl-o-chlorobenzamide (6526-67-6) + trimethoxonium tetrafluoroborate (420-37-1) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
Stage #1: N,N-dimethyl-o-chlorobenzamide; trimethoxonium tetrafluoroborate With disodium hydrogenphosphate In acetonitrile at 20℃; Methylation; Stage #2: With sodium hydrogencarbonate for 18h; Hydrolysis;	95%

di-tert-butyl peroxide (110-05-4) + ortho-chlorobenzoic acid (118-91-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With copper(l) chloride In chlorobenzene at 130℃; for 12h; Schlenk technique; Inert atmosphere;	95%

methanol (67-56-1) + (1-phenyl-1H-imidazol-2-yl)(2-chlorophenyl)methanone → methyl chlorobenzoate (610-96-8)

Conditions	Yield
at 100℃; for 12h; Autoclave; Inert atmosphere;	94%

methanol (67-56-1) + 2-bromo-1-chlorobenzene (694-80-4) + carbon monoxide (201230-82-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With benzophenone; sodium methylate; cobalt(II) acetate at 40℃; under 750.075 Torr; for 15h; Irradiation;	93%

methanol (67-56-1) + 2-Chlorobenzyl alcohol (17849-38-6) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
Stage #1: methanol With sodium tetrachloroaurate(III) dihyrate; potassium carbonate at 20℃; for 0.0166667h; Green chemistry; Stage #2: 2-Chlorobenzyl alcohol at 20℃; for 0.0333333h; Green chemistry; Stage #3: With oxygen at 80℃; under 760.051 Torr; Autoclave; Green chemistry;	90%
With Au#Co; oxygen; potassium carbonate at 80℃; under 750.075 Torr; for 10h; Autoclave;	90%
With oxygen; potassium carbonate at 60℃; under 760.051 Torr; for 12h;	90%

1-(2-chlorophenyl)ethanone (2142-68-9) → methyl chlorobenzoate (610-96-8) + 2-chlorophenyl acetate (4525-75-1)

Conditions	Yield
With hydrogenchloride In chloroform at 20℃; for 12h; Baeyer-Villiger oxidation;	A 6% B 90%

ortho-chlorobenzoic acid (118-91-2) + methyl salicylate (119-36-8) → methyl chlorobenzoate (610-96-8) + salicylic acid (69-72-7)

Conditions	Yield
Stage #1: ortho-chlorobenzoic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl salicylate at 110℃; for 24h;	A 90% B n/a

tris(o-methoxyphenyl)phosphine (4731-65-1) + ortho-chlorobenzoic acid (118-91-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With dirhodium tetraacetate In cyclohexane at 120℃; for 12h; Schlenk technique; Inert atmosphere;	89%

methanol (67-56-1) + 2-chlorobenzamide (609-66-5) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With potassium hydrogensulfate at 65℃; for 72h;	89%

methanol (67-56-1) + 2,2'-dichlorobenzil (21854-95-5) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With sodium cyanide; potassium iodide at 15℃; Electrochemical reaction;	85%

dimethyl sulfate (77-78-1) + ortho-chlorobenzoic acid (118-91-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran for 2h; Methylation; esterification; Heating;	80%

anthranilic acid methyl ester hydrochloride (13516-02-4) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
Stage #1: anthranilic acid methyl ester hydrochloride With isopentyl nitrite In acetone at 0 - 15℃; Stage #2: With copper dichloride In ethanol; acetone at 10 - 20℃; Sandmeyer Reaction;	80%

methanol (67-56-1) + 2-bromo-1-chlorobenzene (694-80-4) + carbon monoxide (201230-82-2) → methyl chlorobenzoate (610-96-8) + phthalic acid dimethyl ester (131-11-3) + ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 10h; Irradiation;	A 76% B 12% C 3%

2-bromo-1-chlorobenzene (694-80-4) + carbon monoxide (201230-82-2) → methyl chlorobenzoate (610-96-8) + phthalic acid dimethyl ester (131-11-3) + ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 10h; Irradiation;	A 76% B 12% C 3%

methanol (67-56-1) + 2-chlorobenzotrichloride (2136-89-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
at 20℃; for 3h; UV-irradiation;	75%

trimethylsulphonium hydroxide (17287-03-5) + ortho-chlorobenzoic acid (118-91-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Esterification;	74%

methanol (67-56-1) + 2-chloro-benzaldehyde (89-98-5) → methyl chlorobenzoate (610-96-8) + ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
With dihydrogen peroxide at 20 - 70℃; for 12h; Green chemistry;	A 74% B 16%
With 3,3'-dimethyl-1,1'-(hexane-1,6-diyl)diimidazolium glutarate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 55℃; for 16h; Molecular sieve;	A 8% B 32%
With dihydrogen peroxide at 80℃; for 6h; Catalytic behavior; Dean-Stark;

2-methallyltrimethylsilane (18292-38-1) + methyl 2-chloro-4-iodobenzoate (156573-32-9) → methyl chlorobenzoate (610-96-8) + methyl 2-chloro-4-(2-methylallyl)benzoate

Conditions	Yield
With cesium fluoride In acetonitrile at -78 - 25℃; for 24h; Irradiation; Sealed tube; Inert atmosphere;	A n/a B 73%

ortho-chlorobenzoic acid (118-91-2) + trimethylphosphane (594-09-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With 1,3-diazido-propane In neat (no solvent) at 20℃; for 0.333333h;	72%

2-methoxymethylchlorobenzene (59579-08-7) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With oxygen In water at 25℃; for 12h; Irradiation; Green chemistry;	71%

benzoic acid methyl ester (93-58-3) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
With N-chloro-succinimide; silver hexafluoroantimonate; trifluorormethanesulfonic acid; nickel diacetate In 1,2-dichloro-ethane at 80℃; for 12h; regioselective reaction;	69%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 1,2-dichloro-benzene (95-50-1) → methyl chlorobenzoate (610-96-8) + ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 71h; Irradiation;	A 61% B 17%

methyl chlorobenzoate (610-96-8) → 2-Chlorobenzyl alcohol (17849-38-6)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; water for 6h; Ambient temperature;	100%
With methanol; sodium tetrahydroborate In tetrahydrofuran at 65℃; for 2h;	97%
With C31H26ClN2OPRu; hydrogen; sodium methylate In tetrahydrofuran at 80℃; for 5h;	94%

methyl chlorobenzoate (610-96-8) → ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h;	100%
With iodine; aluminium In acetonitrile at 80℃; for 18h;	98%
With potassium hydroxide In toluene at 150℃; for 0.166667h; microwave irradiation;	97%

methyl chlorobenzoate (610-96-8) + (2,3-dimethylphenyl)zinc chloride → 2-carbomethoxy-2',3'-dimethylbiphenyl

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); ruphos In tetrahydrofuran at 70℃; Negishi coupling;	100%

methyl chlorobenzoate (610-96-8) + tris(methylthio)methane (5418-86-0) → 1-(2-Chloro-phenyl)-2,2,2-tris-methylsulfanyl-ethanone

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -95℃;	98%

methyl chlorobenzoate (610-96-8) + 2-Methoxyphenylboronic acid (5720-06-9) → 2'-methoxy-biphenyl-2-carboxylic acid methyl ester (63506-58-1)

Conditions	Yield
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; potassium phosphate; palladium diacetate In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura coupling;	98%

methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate (905966-40-7) + methyl chlorobenzoate (610-96-8) → dimethyl (1,1'-biphenyl)-2,4'-dicarboxylate (55676-77-2)

Conditions	Yield
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube;	98%

methyl chlorobenzoate (610-96-8) + 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane (213596-33-9) → methyl 4'-methoxybiphenyl-2-carboxylate (17103-25-2)

Conditions	Yield
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube;	98%

methyl chlorobenzoate (610-96-8) + bis(pinacol)diborane (73183-34-3) → methyl 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2-(dimethyl(phenyl)silyl)-1-(6-methoxypyridin-2-yl)-2,3-dihydro-1H-naphtho[1,8-de]-[1,3,2]diazaborinine In hexane at 80℃; for 20h; Schlenk technique; Inert atmosphere;	98%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; diisopropyl(2-(isopropylthio)phenyl)silane In 2-methyltetrahydrofuran at 80℃; for 16h; Inert atmosphere;	83%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; diisopropyl(2-(isopropylthio)phenyl)silane In 2-methyltetrahydrofuran at 80℃; for 16h; Sealed tube; Inert atmosphere; Glovebox; regioselective reaction;	68%

methyl chlorobenzoate (610-96-8) + tris(allyl)aluminum (18854-66-5) → C13H15ClO

Conditions	Yield
In diethyl ether at 20℃; for 0.5h;	97%

methyl chlorobenzoate (610-96-8) → 2-chlorobenzoylhydrazide (5814-05-1)

Conditions	Yield
With hydrazine hydrate at 20℃; for 2.5h; Cooling with ice;	96%
With hydrazine In methanol Reflux;	94%
With hydrazine hydrate In methanol Reflux;	90%

methyl chlorobenzoate (610-96-8) + phenylboronic acid (98-80-6) → biphenyl-2-carboxylic acid methyl ester (16605-99-5)

Conditions	Yield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate In toluene at 80℃; for 3h; Suzuki-Miyaura coupling;	96%
Stage #1: phenylboronic acid With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-4-(3'-nitrophenyl)benzamide; palladium diacetate In tetrahydrofuran at 23℃; for 0.0166667h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Stage #2: methyl chlorobenzoate In tetrahydrofuran; water at 23℃; for 40h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	90%
With potassium phosphate; n-butyllithium; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide In 1,4-dioxane; hexane at 80℃; for 16h;	89%

methyl chlorobenzoate (610-96-8) + 5,5-dimethyl-1,3,2-dioxaborinane (668987-38-0) → 2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzoic acid methyl ester

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine; zinc In toluene at 100℃; for 1h; Inert atmosphere;	95%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine In toluene at 23 - 100℃; Inert atmosphere;	26%

methyl chlorobenzoate (610-96-8) + phenylmagnesium bromide (100-58-3) → biphenyl-2-carboxylic acid methyl ester (16605-99-5)

Conditions	Yield
Stage #1: methyl chlorobenzoate With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran; toluene Kumada Cross-Coupling; Inert atmosphere; Sealed tube; Stage #2: phenylmagnesium bromide In tetrahydrofuran; toluene at 20℃; for 1h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; chemoselective reaction;	95%

methyl chlorobenzoate (610-96-8) + 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane (380481-66-3) → methyl 4'-methylbiphenyl-2-carboxylate (114772-34-8)

Conditions	Yield
With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Sealed tube;	94%

methyl chlorobenzoate (610-96-8) + dicyanozinc (557-21-1) → methyl 2-cyanobenzoate (6587-24-2)

Conditions	Yield
With zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl acetamide at 120℃; for 2h; Substitution;	93%

methyl chlorobenzoate (610-96-8) + 2-bromo-N-isopentylaniline → 5-isopentylphenanthridin-6(5H)-one

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); bis(pinacol)diborane; tricyclohexylphosphine In 2-ethoxy-ethanol at 100℃; Inert atmosphere;	93%

methyl chlorobenzoate (610-96-8) + 4-methoxyphenylboronic acid (5720-07-0) → methyl 4'-methoxybiphenyl-2-carboxylate (17103-25-2)

Conditions	Yield
With trans-chloro(9-phenanthrenyl)bis(triphenylphosphine)nickel(II); potassium carbonate; triphenylphosphine In toluene at 110℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere;	92%

methyl chlorobenzoate (610-96-8) + methacrylic acid methyl ester (80-62-6) → (E)-3-(2-carbomethoxyphenyl)-2-methyl acrylic acid methyl ester

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; Cy2NMe2 In 1,4-dioxane at 20℃; for 24h; Heck coupling;	91%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; N-Methyldicyclohexylamine In 1,4-dioxane at 20℃; Heck Reaction;	90%

Upstream product

• 67-56-1 methanol 
• 118-91-2 ortho-chlorobenzoic acid 
• 57031-51-3 Methyl-tert.-butylperoxyoxalat 
• 108-90-7 chlorobenzene 
• 186581-53-3 diazomethane 
• 873-32-5 2-Chlorobenzonitrile 
• 57160-47-1 2-chloro-N-((2-chlorophenyl)carbamoyl)benzamide 
• 124-41-4 sodium methylate 
• 89-98-5 2-chloro-benzaldehyde 
• 609-65-4 o-chlorobenzoyl chloride 
• 694-80-4 2-bromo-1-chlorobenzene 
• 201230-82-2 carbon monoxide 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 17287-03-5 trimethylsulphonium hydroxide 

Downstream Products

• 100398-32-1 2-(2'-pyrido)-2-chloroacetophenone 
• 97221-97-1 2-chloro-benzoic acid dodecyl ester 
• 205985-98-4 methyl 2-chlorobenzoylacetate 
• 871879-82-2 N,N'-(9,10-dioxo-9,10-dihydro-anthracene-1,5-diyl)-di-anthranilic acid dimethyl ester 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 118-91-2 ortho-chlorobenzoic acid 
• 66774-02-5 o-chlorotriphenylmethanol 
• 6307-82-0 2-chloro-5-nitro-benzoic acid methyl ester 
• 17512-69-5 2-chlorophenylhydroxamic acid 
• 78325-26-5 5-(2-chloro-phenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol 
• 344-96-7 2-trifluoromethyl-benzoic acid methyl ester 
• 133391-52-3 Methyl 2-pentafluoroethyl-benzoate 
• 117671-81-5 (Z)-1-(2-Chloro-phenyl)-3-hydroxy-5,5-bis-methylsulfanyl-penta-2,4-dien-1-one 
• 127667-31-6 1-hydroxy-1-(2-chlorophenyl)-2-cyano-2-(4-fluorophenyl)ethylene 

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