610-97-9

Basic information

• Product Name: Methyl 2-iodobenzoate
• Synonyms: METHYL O-IODOBENZOATE;METHYL 2-IODOBENZOATE;BENZOIC ACID, 2-IODO-, METHYL ESTER;IBM;2-IODOBENZOIC ACID METHYL ESTER;O-IODOBENZOIC ACID METHYL ESTER;RARECHEM AL BF 0562;2-iodo-benzoicacimethylester
• CAS NO: 610-97-9
• Molecular Formula: C₈H₇IO₂
• Molecular Weight: 262.04
• EINECS: 210-243-6
• Product Categories: Aromatic Esters;Acids & Esters;Iodine Compounds;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 610-97-9.mol
• Article Data: 82

Chemical Properties

• Melting Point: 64°C
• Boiling Point: 149-150 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystalling or Flaky Powder
• Density: 1.784 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: n20/D 1.604(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate (Slightly), Methanol
• Water Solubility: INSOLUBLE
• Sensitive: Light Sensitive
• Stability: Light Sensitive
• BRN: 2206859
• CAS DataBase Reference: Methyl 2-iodobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-iodobenzoate(610-97-9)
• EPA Substance Registry System: Methyl 2-iodobenzoate(610-97-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 610-97-9(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW LIQUID

Uses

Methyl 2-iodobenzoate may be used in the preparation of:N-substituted 4-methylene-3,4-dihydro-1(2H)-isoquinolin-1-onesmethyl diphenylacetylene-2-carboxylatemethyl 2-heptynylphenylbenzoate(E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoic acid methyl ester4-(2-carbomethoxyphenyl)-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione3-(2-carbomethoxyphenyl)-4-methylcyclobuten-3-ene-1,2-dione 2-(ethylene acetal)

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4845, 1971 DOI: 10.1021/ja00748a030

General Description

Methyl 2-iodobenzoate can be prepared from 2-iodobenzoic acid via esterification. It undergoes cobalt-catalyzed cyclization with aldehydes to form phthalide derivatives. The microbial dihydroxylation of methyl 2-iodobenzoate forms a nonracemic iodocyclohexene carboxylate intermediate. This intermediate forms the precursor for preparing kibdelone C.

InChI:InChI=1/C8H7IO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3

Synthetic route

methanol (67-56-1) + 2-Iodobenzoic acid (88-67-5) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With sulfuric acid Reflux;	100%
With sulfuric acid for 3h; Reflux;	99%
With sulfuric acid at 80℃; for 2.5h; Inert atmosphere;	99%

methanol (67-56-1) + 2-Iodobenzoyl chloride (609-67-6) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With sulfuric acid Reflux;	98%
With sodium hydroxide
With oxalyl dichloride In dichloromethane for 0.5h; Inert atmosphere;
With triethylamine at 0 - 20℃; for 2h;
With triethylamine at 0 - 20℃; for 0.5h;	0.42 g

2-Iodobenzoic acid (88-67-5) + methyl iodide (74-88-4) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With potassium carbonate In acetone	98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	96%
Stage #1: 2-Iodobenzoic acid With caesium carbonate In N,N-dimethyl-formamide Stage #2: methyl iodide In N,N-dimethyl-formamide at 50℃; for 1h;	95%

2-(methoxycarbonyl)phenylzinc iodide (693232-15-4) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.166667h; Substitution;	96%
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.166667h;	48%

trifluoroacetic acid-methyl ester (431-47-0) + 1-(2-iodophenyl)pentan-1-one (32730-83-9) → 1,1,1-trifluoro-2-hexanone (360-34-9) + o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Stage #1: trifluoroacetic acid-methyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 1-(2-iodophenyl)pentan-1-one In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;	A n/a B 96%

2-carbomethoxyaniline (134-20-3) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Stage #1: 2-carbomethoxyaniline With sulfuric acid; sodium nitrite In water at 0 - 7℃; Inert atmosphere; Stage #2: With sulfuric acid; sodium hydrogensulfite; potassium iodide In water at -5 - 80℃; for 1.58333h; Inert atmosphere;	93%
Stage #1: 2-carbomethoxyaniline With sulfuric acid; sodium nitrite Stage #2: With potassium iodide
Stage #1: 2-carbomethoxyaniline With toluene-4-sulfonic acid In acetonitrile at 20℃; for 0.166667h; Stage #2: With potassium iodide; sodium nitrite In water; acetonitrile at 0 - 20℃;

2-iodo-N-(quinolin-8-yl)benzamide (723259-89-0) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 110℃; for 36h; Sealed tube;	93%

benzoic acid methyl ester (93-58-3) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Stage #1: benzoic acid methyl ester With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; chemoselective reaction;	89%
Stage #1: benzoic acid methyl ester With (2,2,6,6-tetramethylpiperidido)2Ag(CN)Li2 In tetrahydrofuran at -40℃; for 2h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; chemoselective reaction;	86%
With N-iodo-succinimide; silver hexafluoroantimonate; trifluorormethanesulfonic acid; nickel diacetate In 1,2-dichloro-ethane at 80℃; for 12h; regioselective reaction;	77%
Stage #1: benzoic acid methyl ester With cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction;	62%
With 2,2,6,6-tetramethylpiperidinyl-lithium; iodine; di-tert-butylzinc 1.) THF, RT, 2.) THF, RT; Yield given; Multistep reaction;

boron trifluoride dimethyl etherate (353-42-4) + 2-Iodobenzoic acid (88-67-5) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
at 120℃; for 4h; Reflux;	89%

2-Iodobenzoic acid (88-67-5) + carbonic acid dimethyl ester (616-38-6) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;	88%

tert-butyl methyl ether (1634-04-4) + 2-Iodobenzoic acid (88-67-5) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique;	85%

2-Iodobenzoic acid (88-67-5) + methyl 1-imidazolecarboxylate (61985-23-7) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	84%

Monomethyl phthalate (4376-18-5) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In 1,2-dichloro-ethane for 24h; Irradiation; Inert atmosphere; Reflux;	80%
With N-iodo-succinimide; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; iodine; caesium carbonate In 1,2-dichloro-ethane at 50℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;	65%

2-iodo-N-methoxybenzamide (1225463-02-4) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With N-Bromosuccinimide In toluene at 60℃; for 1h;	76%

methyl 2-(tosyldiazenyl)benzoate (105230-44-2) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With 18-crown-6 ether; potassium iodide In diethyl ether; acetonitrile for 4h; Ambient temperature;	74%

2-Iodobenzoic acid (88-67-5) + [bis(acetoxy)iodo]benzene (3240-34-4) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With copper diacetate; acetic anhydride In N,N-dimethyl-formamide; acetonitrile at 130℃; for 1h; Sealed tube;	57%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 1-(2-iodophenyl)diazonium tetrafluoroborate (7169-58-6) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With fluorescein free acid In acetonitrile at 20℃; under 60804.1 Torr; for 21h; Autoclave; Irradiation;	50%

2-Iodobenzoic acid (88-67-5) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With hydrogenchloride; methanol
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Inert atmosphere 2: oxalyl dichloride / dichloromethane / 0.5 h / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / benzene / 2 h / 80 °C 2: triethylamine / 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 1 h 2: triethylamine / 0.5 h / 0 - 20 °C View Scheme

2-dichloroiodanyl-benzoic acid methyl ester (828-76-2) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With (dissociation) In acetic acid at 15℃; Rate constant;

anthranilic acid (118-92-3) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 - 5 °C / Inert atmosphere 1.2: 1 h / 10 - 90 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Inert atmosphere 3.1: oxalyl dichloride / dichloromethane / 0.5 h / Inert atmosphere View Scheme

N-quinolin-8-yl-benzamide (33757-48-1) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nickel dichloride; ammonium thiocyanate; potassium carbonate / N,N-dimethyl-formamide / 3 h / 120 °C 1.2: -10 °C 2.1: toluene-4-sulfonic acid / methanol / 36 h / 110 °C / Sealed tube View Scheme

benzoyl chloride (98-88-4) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere 1.2: 3 h / 0 - 20 °C / Inert atmosphere 2.1: nickel dichloride; ammonium thiocyanate; potassium carbonate / N,N-dimethyl-formamide / 3 h / 120 °C 2.2: -10 °C 3.1: toluene-4-sulfonic acid / methanol / 36 h / 110 °C / Sealed tube View Scheme

2-bromobenzoic acid methyl ester (610-94-6) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With copper(l) iodide; sodium iodide; zinc(II) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; under 1500.15 Torr; for 24h; Reagent/catalyst; Finkelstein Reaction; Autoclave; Inert atmosphere; Schlenk technique;

methyl 2-{[(4-methylphenyl)sulfonyl]oxy}benzoate (51207-44-4) → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: (1,2-dimethoxyethane)dichloronickel(II); 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene / N,N-dimethyl-formamide; ethylene dibromide / 20 h / 20 °C / Schlenk technique 2: iodine / 0.17 h / 0 °C View Scheme

C15H14O5SZn → o-iodo-methyl-benzoic acid (610-97-9)

Conditions	Yield
With iodine at 0℃; for 0.166667h;	501 mg

o-iodo-methyl-benzoic acid (610-97-9) + ethyl 4-(iodozincio)butanoate (104089-17-0) → ethyl 4-[(2-methoxycarbonyl)phenyl]butanoate (105986-53-6)

Conditions	Yield
dichlorobis(tri-O-tolylphosphine)palladium In N,N-dimethyl acetamide; benzene at 60℃; for 0.5h;	100%

o-iodo-methyl-benzoic acid (610-97-9) + propargyl alcohol (107-19-7) → methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoate (103606-72-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 40℃; for 0.5h; Sonogashira Cross-Coupling; Microwave irradiation;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile for 3h; Inert atmosphere; Reflux;	92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutylammomium bromide; triethylamine In benzene at 60℃; for 0.5h;	90%

o-iodo-methyl-benzoic acid (610-97-9) + phenylacetylene (536-74-3) → methyl 2-(phenylethynyl)benzoate (33578-05-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 55℃; Sonogashira coupling;	99%
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 55℃; Inert atmosphere;	99%

o-iodo-methyl-benzoic acid (610-97-9) + trimethylsilylacetylene (1066-54-2) → methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate (107793-07-7)

Conditions	Yield
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; Sonogashira coupling reaction;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 15h; Sonogashira coupling; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 24h; Inert atmosphere;	100%

o-iodo-methyl-benzoic acid (610-97-9) + 4-methoxyphenylboronic acid (5720-07-0) → methyl 4'-methoxybiphenyl-2-carboxylate (17103-25-2)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; acetonitrile at 60℃; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With bis(triphenylphosphine)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water at 80℃; for 14h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;	95%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In toluene for 18h; Heating;	80%

o-iodo-methyl-benzoic acid (610-97-9) + 2-(1-Hydroxypropyl)-1-ethynylbenzene (166757-15-9) → Methyl 2-<2-<2-(1-hydroxy-1-propyl)phenyl>ethynyl>benzoate (166757-17-1)

Conditions	Yield
With copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; triethylamine for 16h; Heating;	100%

o-iodo-methyl-benzoic acid (610-97-9) + 2-Methoxyphenylboronic acid (5720-06-9) → 2'-methoxy-biphenyl-2-carboxylic acid methyl ester (63506-58-1)

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In water; N,N-dimethyl-formamide for 18h; Suzuki coupling; Ionic liquid; Reflux; Inert atmosphere;	100%
With potassium phosphate; SBA-Si-PEG-Pd(PPh3)n In water at 50℃; for 10h; Suzuki coupling;	89%
With di-tert-butylphosphine; (2,6-iPr2-C6H3OCO-N)-imidazolium-(N-CH2C6H4-2-Br) bromide; caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 150℃; for 48h; Suzuki-Miyaura coupling;	86%
With potassium carbonate In water at 80℃; for 10h; Suzuki-Miyaura Coupling; Green chemistry;	26%

carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) + cyclohexylamine (108-91-8) → N-cyclohexylphthalimide (2133-65-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon In toluene at 120℃; under 4654.46 Torr; for 2h; Autoclave;	93%
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; caesium carbonate In toluene at 95℃; for 24h;	92%

carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) + benzylamine (100-46-9) → N-benzylphthalimide (2142-01-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; caesium carbonate In toluene at 95℃; for 24h; Reactivity; Reagent/catalyst; Concentration; Solvent; Temperature; Time;	91%
With triethylamine In toluene at 100℃;	80%

o-iodo-methyl-benzoic acid (610-97-9) → dimethyl (1,1'-biphenyl)-2,3'-dicarboxylate (32947-58-3)

Conditions	Yield
With norborn-2-ene; palladium diacetate; caesium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 90℃; for 1.5h; Sealed vial;	100%
With norbornene; palladium/alumina; potassium carbonate; benzyl alcohol at 105℃; for 72h;	80%

Cyclopropylacetylene (6746-94-7) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-(cyclopropylethynyl)benzoate

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine at 20℃; Sonogashira coupling;	100%
Stage #1: Cyclopropylacetylene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine	99%

o-iodo-methyl-benzoic acid (610-97-9) + 4-n-methylphenylacetylene (766-97-2) → methyl 2-[(4-methylphenyl)ethynyl]benzoate (118520-72-2)

Conditions	Yield
Stage #1: o-iodo-methyl-benzoic acid; 4-n-methylphenylacetylene With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 1.5h; Sonogashira Cross-Coupling; Inert atmosphere;	100%
Stage #1: o-iodo-methyl-benzoic acid With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 0.0833333h; Stage #2: 4-n-methylphenylacetylene In tetrahydrofuran for 16h; Reflux;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira coupling; Inert atmosphere;	95%

carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) + N-butylamine (109-73-9) → N-butylphthalimide (1515-72-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%
With triethylamine In toluene at 100℃;	79%

4-n-chlorophenylacetylene (873-73-4) + o-iodo-methyl-benzoic acid (610-97-9) → 2-(2-(4-chlorophenyl)ethynyl)benzoic acid methyl ester (118520-71-1)

Conditions	Yield
Stage #1: 4-n-chlorophenylacetylene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere;	100%
Stage #1: 4-n-chlorophenylacetylene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.166667h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 1h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
Sonogashira Cross-Coupling;

o-iodo-methyl-benzoic acid (610-97-9) + trimethylsilylacetylene (1066-54-2) → 2-ethynyl-benzoic acid methyl ester (33577-99-0)

Conditions	Yield
Stage #1: o-iodo-methyl-benzoic acid; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere;	100%

o-iodo-methyl-benzoic acid (610-97-9) + 4-tert-butylphenylboronic acid (123324-71-0) → methyl 4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylate (1528793-37-4)

Conditions	Yield
With bis(triphenylphosphine)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water at 80℃; for 14h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;	100%
With palladium diacetate; sodium carbonate In water; acetonitrile at 60℃; Suzuki-Miyaura Coupling; Inert atmosphere;	90%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 20 - 80℃; Suzuki Coupling; Schlenk technique; Inert atmosphere;
With potassium phosphate; palladium diacetate; triphenylphosphine In toluene at 80℃; Inert atmosphere; Schlenk technique;

tetraacetyl thioglucose (19879-84-6) + o-iodo-methyl-benzoic acid (610-97-9) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (112023-27-5)

Conditions	Yield
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;	100%

3-ethynylthiophene (67237-53-0) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-[2-(thiophen-3-yl)ethynyl]benzoate

Conditions	Yield
Stage #1: 3-ethynylthiophene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 3h; Sonogashira Cross-Coupling; Inert atmosphere;	100%
Stage #1: o-iodo-methyl-benzoic acid With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 1h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: 3-ethynylthiophene In N,N-dimethyl-formamide at 80 - 85℃; for 15h; Sonogashira Cross-Coupling; Inert atmosphere;	82%
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In acetonitrile for 18h; Inert atmosphere; Schlenk technique;	78%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 85℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;

o-iodo-methyl-benzoic acid (610-97-9) + 3-methoxyphenylboronic acid (10365-98-7) → 3'-methoxy-[1,1'-biphenyl]-2-carboxylic acid (38087-96-6)

Conditions	Yield
Stage #1: o-iodo-methyl-benzoic acid; 3-methoxyphenylboronic acid With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,2-dimethoxyethane; water at 180℃; for 0.25h; Microwave irradiation; Stage #2: With sodium hydroxide In methanol; water at 150℃; for 0.0833333h; Microwave irradiation;	100%

1-ethynyl-3-trifluoromethylbenzene (705-28-2) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-((3-(trifluoromethyl)phenyl)ethynyl)benzoate

Conditions	Yield
Stage #1: 1-ethynyl-3-trifluoromethylbenzene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 1.5h; Sonogashira Cross-Coupling; Inert atmosphere;	100%
Stage #1: 1-ethynyl-3-trifluoromethylbenzene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.166667h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 1.5h; Sonogashira Cross-Coupling; Inert atmosphere;	77%

hexan-1-amine (111-26-2) + carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) → N-hexylphthalimide (20320-48-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%

carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) + 4-Aminoacetophenone (99-92-3) → 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione (40101-59-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%

propylamine (107-10-8) + carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) → N-propylphthalimide (5323-50-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%

cyclopentylacetylene (930-51-8) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-(cyclopentylethynyl)benzoate

Conditions	Yield
Stage #1: cyclopentylacetylene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere;	100%

1-Pentyne (627-19-0) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-(pent-1-yn-1-yl)benzoate (90584-93-3)

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 24h; Arylation;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; Condensation;	99%
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 24h; Sonogashira coupling reaction;	98%

pent-1-yn-5-ol (5390-04-5) + o-iodo-methyl-benzoic acid (610-97-9) → 2-(5-hydroxypent-1-ynyl)benzoic acid methyl ester (152771-70-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 15h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
With copper(l) iodide; triethylamine; trans-bis(triphenylphosphine)palladium(II) chloride at 25℃; for 12h;	92%
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Sonogashira coupling reaction;	86%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 55℃; Sonogashira coupling;	85%
Stage #1: o-iodo-methyl-benzoic acid With triethylamine for 0.0833333h; Inert atmosphere; Stage #2: pent-1-yn-5-ol With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; for 7h; Sonogashira coupling; Inert atmosphere;	84%

o-iodo-methyl-benzoic acid (610-97-9) + hex-1-yne (693-02-7) → 2-(1-hexynyl)benzoic acid methyl ester (462637-40-7)

Conditions	Yield
Stage #1: o-iodo-methyl-benzoic acid With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine at 20℃; for 1h; Inert atmosphere; Stage #2: hex-1-yne at 0 - 20℃; Inert atmosphere;	99%
Stage #1: hex-1-yne With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: o-iodo-methyl-benzoic acid In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere; Schlenk technique;	98%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	96%

o-iodo-methyl-benzoic acid (610-97-9) + N-Boc-indole-2-boronic acid (213318-44-6) → methyl 2-[1-(tert-butoxycarbonyl)-1H-indol-2-yl]benzoate (1095343-62-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 12h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 12h; Suzuki coupling; Reflux;	97%

2,2-dimethyl-3-butyne (917-92-0) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-(3,3-dimethylbut-1-yn-1-yl)benzoate (934701-48-1)

Conditions	Yield
Stage #1: 3,3-Dimethylbut-1-yne; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide In N,N-dimethyl-formamide at 50℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-butylamine In diethyl ether Sonogashira coupling;	98%
Stage #1: 3,3-Dimethylbut-1-yne With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: o-iodo-methyl-benzoic acid In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere; Schlenk technique;	91%

Upstream product

• 67-56-1 methanol 
• 88-67-5 2-Iodobenzoic acid 
• 693232-15-4 2-(methoxycarbonyl)phenylzinc iodide 
• 61985-23-7 methyl 1-imidazolecarboxylate 
• 1225463-02-4 2-iodo-N-methoxybenzamide 
• 616-38-6 carbonic acid dimethyl ester 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 201230-82-2 carbon monoxide 
• 7169-58-6 1-(2-iodophenyl)diazonium tetrafluoroborate 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 723259-89-0 2-iodo-N-(quinolin-8-yl)benzamide 
• 98-88-4 benzoyl chloride 
• 353-42-4 boron trifluoride dimethyl etherate 
• 342-54-1 2-(methoxycarbonyl)benzenediazonium tetrafluoroborate 

Downstream Products

• 69352-05-2 2-(2-iodophenyl)propan-2-ol 
• 73183-74-1 2-(10-Phenothiazinyl)benzoesaeure-methylester 
• 64511-19-9 6-(2-carboxy-phenyl)-benzo[1,3]dioxole-5-carboxylic acid 
• 107412-71-5 3'-methyl-[1,1'-biphenyl]-2-carboxylic acid 
• 145439-10-7 3-(2-Methoxycarbonylphenyl)furan-2(5H)-one 
• 147298-11-1 methyl 2-(cyclohex-1-en-1-ylethynyl)benzoate 
• 142458-80-8 methyl 2-(3-methyl-1-butynyl)benzoate 
• 118476-16-7 methyl 2-(hept-1-yn-1-yl)benzoate 
• 133446-39-6 methyl 2-(6-hydroxy-1-hexynyl)benzoate 
• 146406-45-3 methyl 2-(methoxycarbonyl)phenylphosphinate 
• 104033-88-7 2-<(2-Acetylphenyl)(4-methoxyphenyl)amino>benzoesaeure-methylester 
• 104014-19-9 2,2'-<(4-Methylphenyl)imino>bisbenzoesaeure-dimethylester 
• 93-58-3 benzoic acid methyl ester 
• 5216-35-3 1,2-bis(4-chlorophenyl)ethane 

Relevant articles and documents

Connecting binuclear Pd(III) and mononuclear Pd(IV) chemistry by Pd-Pd bond cleavage

Oxidation of binuclear Pd(II) complexes with PhICl2 or PhI(OAc)2 has previously been shown to afford binuclear Pd(III) complexes featuring a Pd-Pd bond. In contrast, oxidation of binuclear Pd(II) complexes with electrophilic trifluoromethylating ("CF3 +") reagents has been reported to afford mononuclear Pd(IV) complexes. Herein, we report experimental and computational studies of the oxidation of a binuclear Pd(II) complex with "CF3 +" reagents. These studies suggest that a mononuclear Pd(IV) complex is generated by an oxidation-fragmentation sequence proceeding via fragmentation of an initially formed, formally binuclear Pd(III), intermediate. The observation that binuclear Pd(III) and mononuclear Pd(IV) complexes are accessible in the same reactions offers an opportunity for understanding the role of nuclearity in both oxidation and subsequent C-X bond-forming reactions.

Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate

The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.

Development of Novel N-hydroxypyridone Derivatives as Potential Anti-Ischemic Stroke Agents

Our previous study had identified ciclopirox (CPX) as a promising lead compound for treatment of ischemic stroke. To find better neuroprotective agents, a series of N-hydroxypyridone derivatives based on CPX were designed, synthesized, and evaluated in this study. Among these derivatives, compound 11 exhibits significant neuroprotection against oxygen glucose deprivation and oxidative stress-induced injuries in neuronal cells. Moreover, compound 11 possesses good blood-brain barrier permeability and superior antioxidant capability. In addition, a complex of compound 11 with olamine-11·Ola possesses good water solubility, negligible hERG inhibition, and superior metabolic stability. The in vivo experiment demonstrates that 11·Ola significantly reduces brain infarction and alleviates neurological deficits in middle cerebral artery occlusion rats. Hence, compound 11·Ola is identified in our research as a prospective prototype in the innovation of stroke treatment.