Methyl 2-iodobenzoate supplier

Name
Methyl 2-iodobenzoate
EINECS 210-243-6
CAS No. 610-97-9
Article Data86
CAS DataBase
Density 1.753 g/cm³
Solubility insoluble in water
Melting Point 64 °C
Formula C₈H₇IO₂
Boiling Point 258.8 °C at 760 mmHg
Molecular Weight 262.047
Flash Point 110.3 °C
Transport Information
Appearance clear yellow liquid
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzoicacid, o-iodo-, methyl ester (6CI,7CI,8CI);2-Iodobenzoic acid methyl ester;Methyl o-iodobenzoate;NSC 34638;
PSA 26.30000
LogP 2.07780

Synthetic route

: 67-56-1
methanol

: 88-67-5
2-Iodobenzoic acid

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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%

: 67-56-1
methanol

: 609-67-6
2-Iodobenzoyl chloride

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 88-67-5
2-Iodobenzoic acid

: 74-88-4
methyl iodide

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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%

: 693232-15-4
2-(methoxycarbonyl)phenylzinc iodide

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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%

: 431-47-0
trifluoroacetic acid-methyl ester

: 32730-83-9
1-(2-iodophenyl)pentan-1-one

A: 360-34-9
1,1,1-trifluoro-2-hexanone

B: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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%

...Expand

: 134-20-3
2-carbomethoxyaniline

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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℃;

: 723259-89-0
2-iodo-N-(quinolin-8-yl)benzamide

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 93-58-3
benzoic acid methyl ester

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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;

: 353-42-4
boron trifluoride dimethyl etherate

: 88-67-5
2-Iodobenzoic acid

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 88-67-5
2-Iodobenzoic acid

: 616-38-6
carbonic acid dimethyl ester

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 1634-04-4
tert-butyl methyl ether

: 88-67-5
2-Iodobenzoic acid

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 88-67-5
2-Iodobenzoic acid

: 61985-23-7
methyl 1-imidazolecarboxylate

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 4376-18-5
Monomethyl phthalate

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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%

: 1225463-02-4
2-iodo-N-methoxybenzamide

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 105230-44-2
methyl 2-(tosyldiazenyl)benzoate

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 88-67-5
2-Iodobenzoic acid

: 3240-34-4
[bis(acetoxy)iodo]benzene

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 7169-58-6
1-(2-iodophenyl)diazonium tetrafluoroborate

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

...Expand

: 88-67-5
2-Iodobenzoic acid

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 828-76-2
2-dichloroiodanyl-benzoic acid methyl ester

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 118-92-3
anthranilic acid

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 33757-48-1
N-quinolin-8-yl-benzamide

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 98-88-4
benzoyl chloride

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 610-94-6
2-bromobenzoic acid methyl ester

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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;

: 51207-44-4
methyl 2-{[(4-methylphenyl)sulfonyl]oxy}benzoate

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 610-97-9
o-iodo-methyl-benzoic acid

Conditions

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

: 610-97-9
o-iodo-methyl-benzoic acid

: 104089-17-0
ethyl 4-(iodozincio)butanoate

: 105986-53-6
ethyl 4-[(2-methoxycarbonyl)phenyl]butanoate

Conditions

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

: 610-97-9
o-iodo-methyl-benzoic acid

: 107-19-7
propargyl alcohol

: 103606-72-0
methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoate

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 536-74-3
phenylacetylene

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

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 1066-54-2
trimethylsilylacetylene

: 107793-07-7
methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 5720-07-0
4-methoxyphenylboronic acid

: 17103-25-2
methyl 4'-methoxybiphenyl-2-carboxylate

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 166757-15-9
2-(1-Hydroxypropyl)-1-ethynylbenzene

: 166757-17-1
Methyl 2-<2-<2-(1-hydroxy-1-propyl)phenyl>ethynyl>benzoate

Conditions

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

: 610-97-9
o-iodo-methyl-benzoic acid

: 5720-06-9
2-Methoxyphenylboronic acid

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

Conditions

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%

: 201230-82-2
carbon monoxide

: 610-97-9
o-iodo-methyl-benzoic acid

: 108-91-8
cyclohexylamine

: 2133-65-5
N-cyclohexylphthalimide

Conditions

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%

...Expand

: 201230-82-2
carbon monoxide

: 610-97-9
o-iodo-methyl-benzoic acid

: 100-46-9
benzylamine

: 2142-01-0
N-benzylphthalimide

Conditions

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%

...Expand

: 610-97-9
o-iodo-methyl-benzoic acid

: 32947-58-3
dimethyl (1,1'-biphenyl)-2,3'-dicarboxylate

Conditions

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%

: 6746-94-7
Cyclopropylacetylene

: 610-97-9
o-iodo-methyl-benzoic acid

: methyl 2-(cyclopropylethynyl)benzoate

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 766-97-2
4-n-methylphenylacetylene

: 118520-72-2
methyl 2-[(4-methylphenyl)ethynyl]benzoate

Conditions

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%

: 201230-82-2
carbon monoxide

: 610-97-9
o-iodo-methyl-benzoic acid

: 109-73-9
N-butylamine

: 1515-72-6
N-butylphthalimide

Conditions

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%

...Expand

: 873-73-4
4-n-chlorophenylacetylene

: 610-97-9
o-iodo-methyl-benzoic acid

: 118520-71-1
2-(2-(4-chlorophenyl)ethynyl)benzoic acid methyl ester

Conditions

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;

: 610-97-9
o-iodo-methyl-benzoic acid

: 1066-54-2
trimethylsilylacetylene

: 33577-99-0
2-ethynyl-benzoic acid methyl ester

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 123324-71-0
4-tert-butylphenylboronic acid

: 1528793-37-4
methyl 4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylate

Conditions

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;

: 19879-84-6
tetraacetyl thioglucose

: 610-97-9
o-iodo-methyl-benzoic acid

: 112023-27-5
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

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%

: 67237-53-0
3-ethynylthiophene

: 610-97-9
o-iodo-methyl-benzoic acid

: methyl 2-[2-(thiophen-3-yl)ethynyl]benzoate

Conditions

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;

: 610-97-9
o-iodo-methyl-benzoic acid

: 10365-98-7
3-methoxyphenylboronic acid

: 38087-96-6
3'-methoxy-[1,1'-biphenyl]-2-carboxylic acid

Conditions

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%

: 705-28-2
1-ethynyl-3-trifluoromethylbenzene

: 610-97-9
o-iodo-methyl-benzoic acid

: methyl 2-((3-(trifluoromethyl)phenyl)ethynyl)benzoate

Conditions

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%

: 111-26-2
hexan-1-amine

: 201230-82-2
carbon monoxide

: 610-97-9
o-iodo-methyl-benzoic acid

: 20320-48-3
N-hexylphthalimide

Conditions

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

...Expand

: 201230-82-2
carbon monoxide

: 610-97-9
o-iodo-methyl-benzoic acid

: 99-92-3
4-Aminoacetophenone

: 40101-59-5
2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione

Conditions

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

...Expand

: 107-10-8
propylamine

: 201230-82-2
carbon monoxide

: 610-97-9
o-iodo-methyl-benzoic acid

: 5323-50-2
N-propylphthalimide

Conditions

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

...Expand

: 930-51-8
cyclopentylacetylene

: 610-97-9
o-iodo-methyl-benzoic acid

: methyl 2-(cyclopentylethynyl)benzoate

Conditions

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%

: 627-19-0
1-Pentyne

: 610-97-9
o-iodo-methyl-benzoic acid

: 90584-93-3
methyl 2-(pent-1-yn-1-yl)benzoate

Conditions

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%

: 5390-04-5
pent-1-yn-5-ol

: 610-97-9
o-iodo-methyl-benzoic acid

: 152771-70-5
2-(5-hydroxypent-1-ynyl)benzoic acid methyl ester

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 693-02-7
hex-1-yne

: 462637-40-7
2-(1-hexynyl)benzoic acid methyl ester

Conditions

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%

: 610-97-9
o-iodo-methyl-benzoic acid

: 213318-44-6
N-Boc-indole-2-boronic acid

: 1095343-62-6
methyl 2-[1-(tert-butoxycarbonyl)-1H-indol-2-yl]benzoate

Conditions

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%

: 917-92-0
2,2-dimethyl-3-butyne

: 610-97-9
o-iodo-methyl-benzoic acid

: 934701-48-1
methyl 2-(3,3-dimethylbut-1-yn-1-yl)benzoate

Conditions

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%

Methyl 2-iodobenzoate Standards and Recommendations

ASSAY: 98.0% min

Methyl 2-iodobenzoate Specification

The IUPAC name of this product is methyl 2-iodobenzoate. With the CAS registry number 610-97-9, it is also named as Benzoic acid, 2-iodo-, methyl ester; AI3-11097; NSC 34638. The product's categories are aromatic esters, acids & esters, iodine compounds, carbonyl compounds and esters.

The Methyl 2-iodobenzoate is clear yellow liquid which is sensitive to light. This chemical must be stored in tightly sealed containers in a cool place. It is irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

The Methyl 2-iodobenzoate is a starting material for the preparation of iodosobenzoate, useful oxidants (such as 2-Iodoxybenzoic acid) which performs the synthesis of carbonyl compounds from primary/secondary alcohols and unsaturated carbonyl compounds from carbonyl compounds.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.74; (4)ACD/LogD (pH 7.4): 2.74; (5)ACD/BCF (pH 5.5): 70.9; (6)ACD/BCF (pH 7.4): 70.9; (7)ACD/KOC (pH 5.5): 735; (8)ACD/KOC (pH 7.4): 735; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.597; (13)Molar Refractivity: 50.93 cm³; (14)Molar Volume: 149.3 cm³; (15)Polarizability: 20.19×10^-24 cm³; (16)Surface Tension: 45.3 dyne/cm; (17)Enthalpy of Vaporization: 49.64 kJ/mol; (18)Vapour Pressure: 0.0134 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 261.949072; (21)MonoIsotopic Mass: 261.949072; (22)Topological Polar Surface Area: 26.3; (23)Heavy Atom Count: 11.

People can use the following data to convert to the molecule structure. SMILES: O=C(OC)c1ccccc1I; InChI: InChI=1/C8H7IO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3; InChIKey: BXXLTVBTDZXPTN-UHFFFAOYAN. Methyl 2-iodobenzoate has many suppliers, such as BenzChem Co., Ltd., Changzhou Ilhang Fine Chemical Co., Ltd. and Changzhou Xixialong International Co., Ltd..

Product Name

Methyl 2-iodobenzoate

Synthetic route

Methyl 2-iodobenzoate Standards and Recommendations

Methyl 2-iodobenzoate Specification

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