615-37-2

Basic information

• Product Name: 2-Iodotoluene
• Synonyms: Toluene,o-iodo-;2-IODOTOLUENE;1-Iodo-2-methylbenzene,;O-IODOTOLUENE;2-Iodotoluene98%;2-Iodotoluene (stabilized with Copper chip);(2-Methylphenyl) iodide;2-Methyl-1-iodobenzene
• CAS NO: 615-37-2
• Molecular Formula: C₇H₇I
• Molecular Weight: 218.03
• EINECS: 210-422-9
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Iodine Compounds;alkyl Iodine
• Mol File: 615-37-2.mol
• Article Data: 93

Chemical Properties

• Melting Point: 11.27°C (estimate)
• Boiling Point: 211 °C(lit.)
• Flash Point: 194 °F
• Appearance: Clear yellow to orange/Liquid
• Density: 1.713 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: n20/D 1.608(lit.)
• Storage Temp.: Room temperature.
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Sensitive: Light Sensitive
• BRN: 1634294
• CAS DataBase Reference: 2-Iodotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodotoluene(615-37-2)
• EPA Substance Registry System: 2-Iodotoluene(615-37-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37-36/37/39-27
• RIDADR: UN 2810
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 615-37-2(Hazardous Substances Data)

Usage

Chemical Properties

Liquid

Uses

Different sources of media describe the Uses of 615-37-2 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Iodotoluene is used as a reagent in the synthesis of aryl substituted quinones as β-secretase inhibitors.

Definition

ChEBI: An iodoarene that is 2-methylbenzene substituted by an iodo group at position 1.

InChI:InChI=1/C7H7I/c1-6-4-2-3-5-7(6)8/h2-5H,1H3

Synthetic route

2-Methylphenylboronic acid (16419-60-6) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With N-iodo-succinimide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) at 90℃; for 0.0833333h; Reagent/catalyst; Microwave irradiation;	100%
With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1h;	88%
With copper(I) oxide; ammonium hydroxide; oxygen; potassium iodide In water at 25℃; for 24h;	81%

2-methylphenyl diazonium tetrafluoroborate (2093-46-1) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With potassium iodide In water at 25℃; for 0.0833333h; Sandmeyer Reaction;	96%
With iodine; potassium iodide In dimethyl sulfoxide at 15℃;
With diiodomethane; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;	53 %Chromat.
With trimethylsilyl iodide at 60 - 70℃; Inert atmosphere; Ionic liquid;

2-methylphenyl bromide (95-46-5) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In acetonitrile at 150℃; for 1h; Buchwald's halogen exchange reaction; Inert atmosphere; Microwave irradiation;	89%
With copper(l) iodide; pyrographite In neat (no solvent) at 150℃; for 23h;	86%
With copper(I) oxide; L-proline; potassium iodide In ethanol at 110℃; for 30h; Schlenk technique; Inert atmosphere; Sealed tube;	28%

potassium o-tolyltrifluoroborate → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With chloroamine-T; sodium iodide In tetrahydrofuran; water at 20℃; for 0.166667h;	86%

2-iodobenzyliodide (4622-38-2) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With indium; water for 11h; ultrasound;	85%

potassium 4-methyl-1-(o-tolyl)-2,6,7-trioxa-1-borabicyclo-[2.2.2]octan-1-uide → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With chloroamine-T; sodium iodide In tetrahydrofuran; water at 20℃; for 0.333333h;	80%

tri-tert-butyl phosphine (13716-12-6) + [(t-Bu)3P](o-tolyl)PdI → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;	79%

o-toluidine (95-53-4) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
Stage #1: o-toluidine With sulfuric acid; silica gel; sodium nitrite at 20℃; grinding; Neat (no solvent); Stage #2: With water at 20℃; grinding; Neat (no solvent); Stage #3: With potassium iodide at 20℃; for 0.166667h; Sandmeyer reaction; grinding; Neat (no solvent);	78%
Diazotization.Behandlung der Diazoniumsulfatloesung mit Jodwasserstoffsaeure;
Multi-step reaction with 2 steps 1: 1) HCl, NaNO2, 2) K2CO3 / 1) H2O, 0 degC, 30 min 2: 72 percent / NaI, sulfonic acid resin (H+ form, Bio-Rad AG 50W-12) / acetonitrile / 0.13 h / 75 °C View Scheme

C6H4S2O4N(1-)*N2C6H5CH2(1+) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 0.75h; Substitution;	75%

carbon monoxide (201230-82-2) + 1-iodyl-2-methylbenzene (16825-70-0) → ortho-methylbenzoic acid (118-90-1) + ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With sodium tetrachloropalladate; sodium carbonate In water at 40℃; for 10h; Yields of byproduct given;	A 74% B n/a

3,3-diethyl-1-(o-tolyl)triaz-1-ene (36719-44-5) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With sulfonic acid resin (H+ form, Bio-Rad AG 50W-12); sodium iodide In acetonitrile at 75℃; for 0.133333h;	72%

toluene (108-88-3) → ortho-methylphenyl iodide (615-37-2) + 4-tolyl iodide (624-31-7)

Conditions	Yield
With iodine; lithium perchlorate In various solvent(s) Ambient temperature; anodic oxidation;	A 30% B 70%
With dinitrogen tetraoxide; pyrographite; ferric nitrate; sodium iodide at 20℃; for 20h;	A 40% B 60%
With iodine In nitromethane at 120℃; for 1h; Sealed tube; Overall yield = 88 %; regioselective reaction;	A 41% B 47%

toluene (108-88-3) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With potassium hydrogensulfate; isoquinolinium dichromate; potassium iodide In water at 20℃; Reagent/catalyst; Temperature; Sonication;	69%
With isoquinolinium dichromate; tetra-(n-butyl)ammonium iodide In water at 25 - 30℃; for 4h; Reagent/catalyst;	66%
With iodine; silver perchlorate; calcium carbonate Ausschluss von Licht;
With sulfuric acid; iodine; nitric acid; acetic acid

4-Phenyl-1-butene (768-56-9) + 4-Iodobenzotrifluoride (455-13-0) + (4-4′-di-tert-butyl-2,2′-bipyridine)NiII(2-tolyl)(I) (1474011-55-6) → ortho-methylphenyl iodide (615-37-2) + 1-(4-phenylbutan-2-yl)-4-(trifluoromethyl)benzene + 1-methyl-2-(4-phenylbutan-2-yl)benzene

Conditions	Yield
With monoisopropoxy(phenyl)silane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; (±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II); 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate at 22℃; Reagent/catalyst; Inert atmosphere; Glovebox;	A 5% B 68% C 1.7%

2-iodobenzyl alcohol (5159-41-1) → ortho-methylphenyl iodide (615-37-2) + bis(2-iodobenzyl) sulfide

Conditions	Yield
With hydrogen sulfide In Hexadecane; toluene at 180℃; under 3000.3 Torr; for 18h; Autoclave;	A 9 %Chromat. B 54%

ortho-methylbenzoic acid (118-90-1) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
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;	52%
With potassium phosphate; iodine In acetonitrile at 140℃; for 16h; Temperature; Solvent; Glovebox; Inert atmosphere; chemoselective reaction;	40%

2-methylchlorobenzene (95-49-8) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
Stage #1: 2-methylchlorobenzene With potassium fluoride; 1,1,1,2,2,2-hexamethyldisilane; water; tris-(dibenzylideneacetone)dipalladium(0); CyJohnPhos In 1,4-dioxane at 100℃; for 24h; Stage #2: With Iodine monochloride In 1,4-dioxane; dichloromethane at 20℃; for 4h; Further stages.;	51%
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In acetonitrile at 200℃; for 1h; Buchwald's halogen exchange reaction; Inert atmosphere; Microwave irradiation;

2-(chloromethyl)iodobenzene (59473-45-9) → ortho-methylphenyl iodide (615-37-2) + phenanthrene (85-01-8) + 9,10-dihydrophenanthrene (776-35-2) + 1,1'-(1,2-Ethylenediyl)bis(2-iodobenzene) (2582-56-1)

Conditions	Yield
With magnesium at 600℃;	A 1% B 12% C 31% D 40%

ortho-tolylmagnesium bromide (932-31-0) + diiodoacetylene (624-74-8) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With diethyl ether unter Kuehlung;

ortho-tolylmagnesium bromide (932-31-0) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
With diethyl ether; iodine

di-o-tolyl-iodonium ; iodide (55145-92-1) → ortho-methylphenyl iodide (615-37-2)

Conditions	Yield
at 155℃;

2-methylphenyl bromide (95-46-5) → ortho-methylphenyl iodide (615-37-2) + 2,2'-dimethyl-1,1'-biphenyl (605-39-0)

Conditions	Yield
With tributylphosphine; potassium iodide; nickel dibromide In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 50℃; for 3h;	A 66 % Chromat. B 23 % Chromat.

toluene (108-88-3) + trifluoroacetic acid (76-05-1) → ortho-methylphenyl iodide (615-37-2) + 4-tolyl iodide (624-31-7) + benzyl trifluoroacetate (351-70-2) + benzaldehyde (100-52-7)

Conditions	Yield
With cobalt(III) acetate; potassium iodide In water at 25℃; for 0.166667h; Product distribution; Mn(OAc)3 or (NH4)2Ce(SO4)3 instead Co(OAc)3; object of study: oxidative iodination promoted by Co(III), Ni(III) or Ce(IV);
With cobalt(III) acetate In water at 25℃; for 0.166667h; Yield given. Yields of byproduct given;

toluene (108-88-3) → ortho-methylphenyl iodide (615-37-2) + 3-Iodotoluene (625-95-6) + 4-tolyl iodide (624-31-7)

Conditions	Yield
With iodine In acetonitrile Mechanism; Product distribution; electrochemical iodination in presence of benzene; anode: platinum beaker, cathode: nickel spiral, electrolyte: sodium perchlorate; further reagent (CH3-C=N-I)(1+)*ClO4(1-);
With aluminum oxide; iodine for 20h; Ambient temperature; Yield given. Yields of byproduct given;

toluene (108-88-3) → ortho-methylphenyl iodide (615-37-2) + 4-tolyl iodide (624-31-7) + benzyl trifluoroacetate (351-70-2) + benzaldehyde (100-52-7)

Conditions	Yield
With cobalt(III) acetate; trifluoroacetic acid In water at 25℃; for 0.166667h; Yield given. Yields of byproduct given;

toluene (108-88-3) → ortho-methylphenyl iodide (615-37-2) + 3-Iodotoluene (625-95-6) + 4-tolyl iodide (624-31-7) + Dibromo-iodo-p-tolyl-silane + Dibromo-iodo-m-tolyl-silane + Dibromo-iodo-o-tolyl-silane

Conditions	Yield
With Silicon dibromide; Iodine monochloride at -90℃; Product distribution;

toluene (108-88-3) → ortho-methylphenyl iodide (615-37-2) + 3-Iodotoluene (625-95-6)

Conditions	Yield
With iodine; silver trifluoroacetate In dichloromethane

(2-Methylphenyl)(4'-methoxyphenyl)iodonium trifluoroacetate → ortho-methylphenyl iodide (615-37-2) + 2-Fluorotoluene (95-52-3) + para-iodoanisole (696-62-8) + methoxybenzene (100-66-3)

Conditions	Yield
With cesium fluoride In acetonitrile at 85℃; for 0.666667h; GC-MS estimated relative yields;

o-tolyl(p-tolyl)iodonium trifluoromethanesulfonate → p-fluorotoluene (352-32-9) + ortho-methylphenyl iodide (615-37-2) + 2-Fluorotoluene (95-52-3) + 4-tolyl iodide (624-31-7) + toluene (108-88-3)

Conditions	Yield
With cesium fluoride In acetonitrile at 85℃; for 0.666667h; GC-MS estimated relative yields;

ortho-methylphenyl iodide (615-37-2) → toluene (108-88-3)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 12h; Inert atmosphere;	100%
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 5h; ultrasonic acceleration of reduction;	95%
With 2,2'-azobis(isobutyronitrile); poly(n-hexylsilane) In benzene-d6 at 82 - 85℃; for 3h; sealed;	99 % Spectr.

ortho-methylphenyl iodide (615-37-2) + benzene-1,4-diboronic acid bispinacol ester (99770-93-1) → 2,2”-dimethyl-1,1‘:4’,1“-terphenyl (53092-64-1)

Conditions	Yield
With silver carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 16h; Suzuki cross-coupling reaction; Heating;	100%

ortho-methylphenyl iodide (615-37-2) + trimethylsilylacetylene (1066-54-2) → trimethyl[(2-methylphenyl)ethynyl]silane (3989-15-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 4h; Sonogashira Cross-Coupling; Inert atmosphere;	98%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling; Inert atmosphere;	97%

ortho-methylphenyl iodide (615-37-2) + dimethyl(hept-1-yn-1-yl)aluminum → 1-(1-heptynyl)-2-methylbenzene (64146-63-0)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In 1,2-dimethoxyethane; n-heptane at 85℃; for 3h;	100%

ortho-methylphenyl iodide (615-37-2) + para-thiocresol (106-45-6) → (2‑methylphenyl)(4‑methylphenyl) sulfide (4279-70-3)

Conditions	Yield
Stage #1: para-thiocresol With potassium hydroxide In methanol at 70℃; for 0.25h; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: ortho-methylphenyl iodide With copper(l) iodide In methanol at 110℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	100%
With sodium hydroxide; copper(l) iodide; tetrabutylammomium bromide In toluene for 22h; Ullmann coupling; Heating;	96%
With caesium carbonate In 1,4-dioxane; N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;	91%
With copper(ll) sulfate pentahydrate; caesium carbonate; sodium L-ascorbate In dodecane at 100℃; for 16h; Catalytic behavior; Schlenk technique; Green chemistry;	90%
With pyridine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	92 %Spectr.

norborn-2-ene (498-66-8) + ortho-methylphenyl iodide (615-37-2) → exo-5-Methyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide; palladium diacetate; triphenylphosphine In water; toluene at 80℃; for 12h; Inert atmosphere; Sealed vial; regioselective reaction;	100%

ortho-methylphenyl iodide (615-37-2) + stilbene (588-59-0) → 1-(2-Methylphenyl)-1,2-diphenylethen (70588-52-2, 70588-53-3, 1985-77-9)

Conditions	Yield
With silver(I) acetate; palladium diacetate In acetic acid at 110℃; for 6h; Heck Reaction; Inert atmosphere;	100%

ortho-methylphenyl iodide (615-37-2) + phenylboronic acid (98-80-6) → 2-methylbiphenyl (643-58-3)

Conditions	Yield
With 3-(2-(diphenylarsinyl)benzyl)-1-phenyl-1H-imidazol-3-ium chloride; palladium diacetate; caesium carbonate In ISOPROPYLAMIDE at 60℃; for 19h; Suzuki coupling; Inert atmosphere;	99%
With sodium carbonate In water at 100℃; Suzuki-Miyaura reaction;	99.5%
With potassium carbonate In toluene at 80℃; for 6h; Suzuki coupling; Inert atmosphere;	99%

ortho-methylphenyl iodide (615-37-2) + thiophenol (108-98-5) → 2-(phenylthio)toluene (13963-35-4)

Conditions	Yield
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; sodium t-butanolate In 1,2-dimethoxyethane at 70℃; for 24h; Inert atmosphere;	99%
With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate In toluene at 110℃; for 24h;	96%
With sodium t-butanolate; copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline In toluene at 110℃; for 24h; Product distribution / selectivity;	96%

ortho-methylphenyl iodide (615-37-2) + acrylic acid methyl ester (292638-85-8) → methyl (E)-3-(2-methylphenyl)-2-propenoate (70625-62-6, 75950-75-3, 130451-86-4)

Conditions	Yield
With trihexyl(tetradecyl)phosphonium chloride; sodium acetate; palladium diacetate In water at 50℃; for 2h; Heck reaction;	99%
With triethylamine; bis-<(4-Cl-2-PdCl-Ph)-(4-Cl-Ph)-methanone oxime> In N,N-dimethyl-formamide at 110℃; for 3h; Product distribution; Further Variations:; Reaction partners; Reagents; Temperatures; Heck-Mizoroki reaction;	99%
With triethylamine In water; N,N-dimethyl-formamide; toluene at 100℃; for 20h; Mizoroki-Heck reaction;	99%

ortho-methylphenyl iodide (615-37-2) + phenylacetylene (536-74-3) → 1-phenylethynyltoluene (14309-60-5)

Conditions	Yield
With copper(l) iodide; rac-N2,N2'-bis(benzyl)-1,1'-binaphthyl-2,2'-diamine; potassium carbonate In N,N-dimethyl-formamide at 140 - 145℃; for 8h; Sonogashira coupling; Inert atmosphere;	99%
With C19H25CuN5(1+)*F6P(1-); potassium carbonate In N,N-dimethyl-formamide at 135 - 140℃; Sonogashira Cross-Coupling; Sealed tube;	99%
With palladium diacetate; potassium carbonate In ethanol at 80℃; for 24h;	99%

ortho-methylphenyl iodide (615-37-2) + 4-methylphenylboronic acid (5720-05-8) → 2,4'-dimethylbiphenyl (611-61-0)

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	99%
With Ti0998Pd0002; potassium carbonate In methanol at 120℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	88%
With potassium hydroxide; PEG-PS resin-supported Pd-monophosphine at 25℃; for 24h;	80%
With potassium carbonate In ethanol; water at 80℃; for 3h; Suzuki Coupling;	95 %Chromat.

ortho-methylphenyl iodide (615-37-2) + 2-Methylphenylboronic acid (16419-60-6) → 2,2'-dimethyl-1,1'-biphenyl (605-39-0)

Conditions	Yield
With potassium carbonate In ethanol Suzuki-Miyaura Coupling; Schlenk technique; Heating;	99%
With potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 20℃; for 2.5h; Suzuki cross-coupling;	98%
With potassium fluoride; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 5h; Suzuki cross-coupling;	98%

ortho-methylphenyl iodide (615-37-2) + 4-acetylphenylboronic acid (149104-90-5) → 4-acetyl-2'-methylbiphenyl (56917-39-6)

Conditions	Yield
With silver tetrafluoroborate; C16H36N(1+)*C32H25Cl2Fe2N2O3PdS(1-); potassium carbonate In water for 0.25h; Suzuki coupling; Microwave irradiation;	99%
With potassium fluoride; silver tetrafluoroborate; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 20h; Suzuki cross-coupling;	98%
With potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 20℃; for 1h; Suzuki cross-coupling;	96%
With potassium fluoride; potassium carbonate In water at 100℃; for 6h; Suzuki-Miyaura coupling;	93%

ortho-methylphenyl iodide (615-37-2) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)-2-methylbenzenamine (85448-89-1)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); sodium t-butanolate; DavePhos In 1,4-dioxane at 45℃;	99%
With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃;	95%
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 45℃; for 15h;	92%
With sodium t-butanolate; C42H52O3NP; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 45℃;	89%
With potassium phosphate; tris(1,10-phenanthroline)ruthenium(II) complex; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH3CN)2](PF6)2 In acetonitrile for 24h; Irradiation;	30%

ortho-methylphenyl iodide (615-37-2) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2-methyl-4-(2-methylphenyl)-3-butyn-2-ol (40888-14-0)

Conditions	Yield
With copper(l) iodide; tetra-(n-butyl)ammonium iodide; diethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 70℃; for 2.5h;	99%
With potassium carbonate; copper(l) chloride In methanol; acetonitrile at 25 - 30℃; for 12h; Sonogashira Cross-Coupling; Inert atmosphere; Irradiation;	90%
With copper(l) iodide; tetra-(n-butyl)ammonium iodide; diethylamine; bis-triphenylphosphine-palladium(II) chloride

ortho-methylphenyl iodide (615-37-2) + bicyclopropylidene (27567-82-4) + acrylic acid methyl ester (292638-85-8) → methyl syn/anti-8-(2-methylphenyl)spiro[2.5]oct-7-ene-5-carboxylate

Conditions	Yield
With tetraethylammonium chloride; potassium carbonate; triphenylphosphine; palladium diacetate In acetonitrile at 80℃; for 48h; domino Heck-Diels-Alder reaction;	99%

acetamide (60-35-5) + ortho-methylphenyl iodide (615-37-2) → N-(2-methylphenyl)acetamide (120-66-1)

Conditions	Yield
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In toluene at 110℃; for 8h;	99%
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 80℃; for 23h;	95%
With aluminum oxide; potassium fluoride; copper(l) iodide; N,N'-Dibenzylethylenediamine In toluene at 110℃; for 3h; Ullmann reaction; Inert atmosphere;	90%

ortho-methylphenyl iodide (615-37-2) + acrylic acid (79-10-7) → (E)-3-(2-methylphenyl)acrylic acid (939-57-1, 2373-76-4, 41397-71-1)

Conditions	Yield
With potassium hydroxide; PS-PEG-NH-C(O)C6H4PPh2-PdCl(η3-C3H5) at 50℃; Heck reaction;	99%
With tri-n-propylamine; triphenylphosphine; 3-methyl-1-[2-(perfluorodecyl)ethyl]imidazolium iodide; palladium diacetate In various solvent(s) at 120℃; for 2h; Mizoroki-Heck arylation;	91%
With sodium carbonate In water at 120℃; for 12h; Green chemistry;	62.3%
With potassium carbonate In water at 80℃; for 20h; Heck reaction;	47 %Spectr.

ortho-methylphenyl iodide (615-37-2) + diphenyl diselenide (1666-13-3) → phenyl o-tolyl selenide (94800-50-7)

Conditions	Yield
With copper(II) sulfide; iron; potassium carbonate In dimethyl sulfoxide at 110℃; for 6h; Inert atmosphere; chemoselective reaction;	99%
With copper(I) oxide; [2,2]bipyridinyl; magnesium In N,N-dimethyl-formamide at 110℃; for 30h;	92%
With magnesium In N,N-dimethyl-formamide at 110℃; for 30h; Inert atmosphere; Schlenk technique; Green chemistry;	90%

ortho-methylphenyl iodide (615-37-2) + acrylic acid n-butyl ester (141-32-2) → butyl 3-o-tolylacrylate

Conditions	Yield
With potassium carbonate at 120℃; for 0.5h; Catalytic behavior; Heck Reaction;	99%
With triethylamine at 100℃; for 1.66667h; Reagent/catalyst; Heck Reaction; Sealed tube;	98%
With triethylamine In N,N-dimethyl-formamide at 85℃; for 0.333333h; Catalytic behavior; Solvent; Heck Reaction;	97%

ortho-methylphenyl iodide (615-37-2) + acrylic acid n-butyl ester (141-32-2) → butyl (2E)-3-(2-methylphenyl)acrylate (163977-61-5)

Conditions	Yield
With C68H96Br2N2O8P2Pd2; triethylamine; 3,3'-di-tert-butyl-5,5'-dimethoxybiphenyl-2,2'-diyl diisopropylphosphoramidite In 1-methyl-pyrrolidin-2-one at 80℃; for 16h; Mizoroki-Heck reaction; Inert atmosphere; regioselective reaction;	99%
With tributyl-amine; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In 1-methyl-pyrrolidin-2-one at 140℃; for 15h; Heck Reaction; Inert atmosphere;	99%
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; diamminedichloropalladium(II); tributyl-amine In water at 140℃; for 48h; Mizoroki-Heck cross-coupling; Sealed tube;	95%

ortho-methylphenyl iodide (615-37-2) + (3E)-4-[isopropoxy(dimethyl)silyl]-1-phenylbut-3-an-1-ol (119093-12-8) → (3E)-4-(2-methylphenyl)-1-phenylbut-3-en-1-ol

Conditions	Yield
With tetrabutyl ammonium fluoride; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 20℃; for 3h;	99%

ortho-methylphenyl iodide (615-37-2) + N-o-tolyl-hydrazinecarboxylic acid tert-butyl ester (380383-85-7) → N,N'-di-o-tolyl-hydrazinecarboxylic acid tert-butyl ester

Conditions	Yield
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 2h; Heating;	99%

ortho-methylphenyl iodide (615-37-2) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → atomoxetine hydrochloride (82248-59-7)

Conditions	Yield
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=11 - 12;	99%
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=11 - 12;	94%
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium phosphate; copper(l) iodide In toluene for 24h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=12 - 14;	82%

ortho-methylphenyl iodide (615-37-2) + p-toluidine (106-49-0) → N-(4-methylphenyl)-2-methylaniline (34160-14-0)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 48h;	99%
With nickel(II) iodide; potassium phosphate; 2-Phenyl-1,3,2-dioxaborinane In 1,4-dioxane at 115℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; chemoselective reaction;	86%

triethylsilane (617-86-7) + ortho-methylphenyl iodide (615-37-2) → (2-methylphenyl)triethylsilane (18412-78-7)

Conditions	Yield
With potassium phosphate; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate In 1-methyl-pyrrolidin-2-one at 20℃; for 96h;	99%

1-octyl-4-phenyl-1H-[1,2,3]triazole (853052-50-3) + ortho-methylphenyl iodide (615-37-2) → 1-N-octyl-4-phenyl-5-(2-tolyl)-1H-1,2,3-triazole (1037412-34-2)

Conditions	Yield
With copper(l) chloride; lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 9h; Inert atmosphere;	99%
With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 20h; Inert atmosphere; regioselective reaction;	98%

ortho-methylphenyl iodide (615-37-2) + 2,4,5-trimethylphenylacetylene → 1,2,4-trimethyl-5-[(2-methylphenyl)ethynyl]benzene (1191900-12-5)

Conditions	Yield
With potassium phosphate; C28H47ClN4P2Pd In 1,4-dioxane; ethylene glycol at 140℃; for 0.25h; Sonogashira coupling; Inert atmosphere;	99%

Upstream product

• 7553-56-2 iodine 
• 7697-37-2 nitric acid 
• 108-88-3 toluene 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 76-03-9 trichloroacetic acid 
• 64-19-7 acetic acid 
• 4622-38-2 2-iodobenzyliodide 
• 210823-54-4 2-methylphenyl(mesityl)iodonium trifluoromethanesulfonate 
• 16419-60-6 2-Methylphenylboronic acid 
• 59473-45-9 2-(chloromethyl)iodobenzene 
• 76-05-1 trifluoroacetic acid 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 101895-72-1 N-(2-methyl-phenyl)-phenothiazine 
• 730984-84-6 2-(diphenylamino)-3-methylbenzoic acid 
• 617-00-5 2,2'-dimethyldiphenylamine 
• 7287-73-2 2,2',2''-Trimethyltriphenylamine 
• 132145-21-2 3-(o-tolyl)-4-methyl-7-diethylamino-2H-benzopyran-2-one 
• 118-90-1 ortho-methylbenzoic acid 
• 70625-62-6 methyl (E)-3-(2-methylphenyl)-2-propenoate 
• 98288-15-4 methyl 2-methoxycinnamate 
• 577-16-2 2-Methylacetophenone 
• 137-06-4 2-thiocresol 
• 129081-98-7 diethyl <4-(o-tolyl)but-2-enyl>malonate 
• 129082-02-6 diethyl bis<4-(o-tolyl)but-2-enyl>malonate 
• 86239-16-9 (2-Methylphenyl)malononitrile 
• 10175-33-4 1-(2-iodophenyl)-N,N-dimethylmethanamine 

Relevant articles and documents

Direct Aromatic Iodination Using IF Prepared from I2 and F2

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Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles

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Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive

Convenient access to diverse libraries of internal alkynes via decarboxylative Sonogashira reaction of alkynyl-carboxylic acids with iodoarenes, employing imidazolium-ILs as solvent, along with piperidine-appended imidazolium [PAIM][NTf2] as task-specific basic IL is demonstrated, without the need for any ligand or additive. The feasibility to perform these reactions by sequential one-pot iododediazoniation/decarboxylative Sonogashira reaction is also shown, and the scope of the methods is underscored by providing 29 examples. The potential for recycling and reuse of the IL solvent is also examined.