16419-60-6

Basic information

• Product Name: 2-Tolylboronic acid
• Synonyms: 2-METHYLPHENYLBORONIC ACID;2-METHYLBENZENEBORONIC ACID;2-TOLYLBORONIC ACID;AKOS BRN-0017;TOLUENE-2-BORONIC ACID;O-TOLYLBORONIC ACID;O-METHYLPHENYLBORONIC ACID;RARECHEM AH PB 0228
• CAS NO: 16419-60-6
• Molecular Formula: C₇H₉BO₂
• Molecular Weight: 135.96
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Boronic Acid series;Boron, Nitrile, Thio,& TM-Cpds;Substituted Boronic Acids;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;CHIRAL CHEMICALS;organic or inorganic borate;Boronate Ester;Potassium Trifluoroborate
• Mol File: 16419-60-6.mol
• Article Data: 44

Chemical Properties

• Melting Point: 162-164 °C(lit.)
• Boiling Point: 283.4 °C at 760 mmHg
• Flash Point: 125.2 °C
• Appearance: Beige/Crystalline Powder
• Density: 1.1 g/cm³
• Vapor Pressure: 8.13E-05mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 8.61±0.58(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 2935796
• CAS DataBase Reference: 2-Tolylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Tolylboronic acid(16419-60-6)
• EPA Substance Registry System: 2-Tolylboronic acid(16419-60-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: ED7777777
• HazardClass: IRRITANT
• Hazardous Substances Data: 16419-60-6(Hazardous Substances Data)

Usage

Description

2-Methylphenylboronic acid is an important organic boronic acid compound, which is widely used in Suzuki cross-coupling reaction and has important application value in the fields of organic synthesis and medicine and chemical industry.

Physical properties

beige crystalline powder

Uses

Different sources of media describe the Uses of 16419-60-6 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Methylbenzeneboronic acid is a reagent used for Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water, Ruthenium catalyzed direct arylation reactions, Ligand-free copper-catalyzed coupling reactions, Rhodium-catalyzed asymmetric 1,4-addition reactions. Reagent used in Preparation of chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction, Human farnesyl pyrophosphate synthase inhibitors as antitumor agents for multiple myeloma cells

InChI:InChI=1/C7H9BO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3

Synthetic route

2-methylphenylboronic acid pinacol ester (195062-59-0) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: 2-methylphenylboronic acid pinacol ester With potassium hydrogen difluoride In methanol at 20℃; for 0.25h; Stage #2: With chloro-trimethyl-silane; water In acetonitrile for 1h;	100%
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h;	90%

2-methylchlorobenzene (95-49-8) → 2,2'-dimethyl-1,1'-biphenyl (605-39-0) + 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With cesium fluoride; Pd(dba)2 In toluene	A n/a B 97%

2-methylphenyl bromide (95-46-5) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: 2-methylphenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃;	92%
Stage #1: 2-methylphenyl bromide With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;	35%
With n-butyllithium; Triisopropyl borate

potassium o-tolyltrifluoroborate → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h;	92%
With water; silica gel at 20℃; for 1h; Inert atmosphere;	61%

ortho-tolylmagnesium bromide (932-31-0) + diisopropopylaminoborane (22092-92-8) + water (7732-18-5) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: ortho-tolylmagnesium bromide; diisopropopylaminoborane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere;	88%

Trimethyl borate (121-43-7) + 2-methylphenyl bromide (95-46-5) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;	88%

Trimethyl borate (121-43-7) + Triisopropyl borate (5419-55-6) + 2-methylphenyl bromide (95-46-5) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: Triisopropyl borate; 2-methylphenyl bromide With magnesium; ethylene dibromide In tetrahydrofuran at 40 - 60℃; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran for 6h; Inert atmosphere; Reflux;	85%

(2-tolyl)tributyltin (68971-87-9) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With borane; water In tetrahydrofuran for 1h; Heating;	83%

2-methylphenyl N-methyliminodiacetic acid borate → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: 2-methylphenyl N-methyliminodiacetic acid borate With sodium hydroxide In tetrahydrofuran for 0.416667h; Stage #2: In aq. phosphate buffer; diethyl ether pH=7;	82%

2-methylphenyl triflate (66107-34-4) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: 2-methylphenyl triflate With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;	78%

ortho-tolylmagnesium bromide (932-31-0) + Trimethyl borate (121-43-7) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With sulfuric acid In diethyl ether 2M o-tolyl-magnesium bromide added dropwise with stirring at -60°C for 2 h to trimethylborate in ethyl ether, temp. allowed to rise to 0°C, water added, pH adjusted to pH 3 with 2M sulfuric acid; filtered, extd. (ethyl ether), evapd., washed (petroleum ether), recrystd. (water);	73%
In diethyl ether

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

Conditions	Yield
Stage #1: ortho-methylphenyl iodide With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;	73%

ortho-tolylmagnesium bromide (932-31-0) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: ortho-tolylmagnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #2: With hydrogenchloride In water	63%

tetrahydroxydiboron (13675-18-8) + o-toluidine (95-53-4) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: o-toluidine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h; Stage #2: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;	63%
Stage #1: o-toluidine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h; Stage #2: tetrahydroxydiboron With potassium carbonate In water at 20℃; for 0.333333h;

(2-methylphenyl)lithium (6699-93-0) + diborane (19287-45-7) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With copper(I) bromide In not given Li educt added to CuBr slurry in ether at 0°C under N2, reacted for 10 min, B2H6 soln. added, stirred for 18 h at room temp.; hydrolyzed with H2O, then with aq. NaOH, extd. with ether, aq. phase acidified with aq. HCl, extd. with ether, exts. dried (MgSO4), ether removed, solid recrystd. (petroleum ether);	60%

hydrogenchloride (7647-01-0) + Trimethyl borate (121-43-7) + 2-methylphenyl bromide (95-46-5) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Stage #1: 2-methylphenyl bromide With iodine; magnesium In tetrahydrofuran at 50 - 60℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -15 - 20℃; for 2h; Inert atmosphere; Stage #3: hydrogenchloride In tetrahydrofuran; water at 0℃; pH=2 - 3;	50%

tetrahydroxydiboron (13675-18-8) + 2-methylphenyl diazonium tetrafluoroborate (2093-46-1) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.25h;	36%

ortho-tolylmagnesium bromide (932-31-0) + triisobutyl borate (13195-76-1) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With diethyl ether und anschliessenden Hydrolyse;

(2-methylphenyl)dichloroborane (4250-48-0) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With water

(2-methylphenyl)dichloroborane (4250-48-0) + water (7732-18-5) → 2-Methylphenylboronic acid (16419-60-6)

tri-o-tolylboroxine (7294-50-0) + water (7732-18-5) → 2-Methylphenylboronic acid (16419-60-6)

bis(2-tolyl) mercury (616-99-9) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: BCl3 / 150 - 180 °C 2: water View Scheme

Trimethyl borate (121-43-7) + 2-methylphenyl bromide (95-46-5) + tert.-butyl lithium (594-19-4) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; pentane

borane (13283-31-3) + tetra-o-tolyltin (5728-01-8) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With water In tetrahydrofuran; diethyl ether; ethanol to THF soln. of Sn compd. added BH3 (N2, room temp.),refluxed (4 h), added H2O,stirred (30 min),extd. (Et2O), dried (MgSO4),evapd. in vac.,heated with pentane,filtered ArB(OH)2; ArB(OH)2 recrystd. from H2O; identified by m. p., IR, NMR;

Triisopropyl borate (5419-55-6) + 2-bromo-3,4-dimethoxybenzylaldehyde (55171-60-3) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran dissolved aromatic bromide in THF, added n-BuLi dropwise, mixt. stirredat -78°C for 15 min; added freshly distd. ((CH3)2CHO)3B, stirredat -78°C for 30 min, warmed to room temp., stirred for further 20 min; cooled to 0°C, acidified, extracted with CH2Cl2, dried, evapd. under vac.;	>99

Triisopropyl borate (5419-55-6) + 2-bromophenyl methyl ketone (2142-69-0) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran dissolved aromatic bromide in THF, added n-BuLi dropwise, mixt. stirredat -78°C for 15 min; added freshly distd. ((CH3)2CHO)3B, stirredat -78°C for 30 min, warmed to room temp., stirred for further 20 min; cooled to 0°C, acidified, extracted with CH2Cl2, dried, evapd. under vac.;	>99

Trimethyl borate (121-43-7) + 2-bromo-3,4-dimethoxybenzylaldehyde (55171-60-3) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran dissolved aromatic bromide in THF, added n-BuLi dropwise, mixt. stirredat -78°C for 15 min; added freshly distd. (CH3O)3B, stirred at -78°C for 30 min, warmed to room temp., stirred for further 20 min; cooled to 0°C, acidified, extracted with CH2Cl2, dried, evapd. under vac.;	>99

Trimethyl borate (121-43-7) + 2-bromophenyl methyl ketone (2142-69-0) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran dissolved aromatic bromide in THF, added n-BuLi dropwise, mixt. stirredat -78°C for 15 min; added freshly distd. (CH3O)3B, stirred at -78°C for 30 min, warmed to room temp., stirred for further 20 min; cooled to 0°C, acidified, extracted with CH2Cl2, dried, evapd. under vac.;	>99

dimethoxy-o-tolyl-borane (110180-68-2) → 2-Methylphenylboronic acid (16419-60-6)

Conditions	Yield
With hydrogenchloride; water Inert atmosphere;	2.07 g
With hydrogenchloride In water at 20℃; Inert atmosphere; Schlenk technique;

2-Methylphenylboronic acid (16419-60-6) → tri-o-tolylboroxine (7294-50-0)

Conditions	Yield
In benzene Heating;	100%
With sulfuric acid
(dehydration);

2-bromo-pyridine (109-04-6) + 2-Methylphenylboronic acid (16419-60-6) → 2-(2-methylphenyl)pyridine (10273-89-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 12h; Suzuki Coupling; Inert atmosphere;	96%
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 1h; Suzuki coupling;	94%

1-bromo-4-methoxy-benzene (104-92-7) + 2-Methylphenylboronic acid (16419-60-6) → 4'-methoxy-2-methylbiphenyl (92495-54-0)

Conditions	Yield
With C31H26N6O4Pd; potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura coupling;	100%
With C38H53Cl2N2O2PPd*CH2Cl2; tetrabutylammomium bromide; potassium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique;	100%
With potassium phosphate; (PdCl2)(2-pyridyl)-6-isopropyl cis piperidine complex In water; N,N-dimethyl-formamide at 110℃; for 2h;	99%

4-Bromobenzoic acid (586-76-5) + 2-Methylphenylboronic acid (16419-60-6) → 4-(2-methylphenyl)benzoic acid (5748-43-6)

Conditions	Yield
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;	100%
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;	99%
With 4C3H6N6*Pd(2+)*2C2H3O2(1-); sodium carbonate In water at 80℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry;	97%

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-bromophenyl methyl ketone (2142-69-0) + 2-Methylphenylboronic acid (16419-60-6) → 1-(2′-methyl-[1,1′-biphenyl]-2-yl)ethanone (217468-51-4)

Conditions	Yield
With potassium phosphate; CyJohnPhos; polymer-incarcerated palladium In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol Product distribution; Heating; Suzuki coupling of bromo-acylbenzenes resp. bromo-indole carbaldehydes with boronic acids;	98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol rt, 15 min; reflux, 48 h;	98%

1-bromo-4-tert-butylbenzene (3972-65-4) + 2-Methylphenylboronic acid (16419-60-6) → 2-methyl-4'-tert-butylbiphenyl

Conditions	Yield
With potassium phosphate; palladium-incarcerated polystyrene-based copolymer; tris(o-methoxyphenyl)phosphine In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;	100%
With C25H29N3; potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 90℃; for 2h; Suzuki-Miyaura Coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene at 110℃; for 1.5h; Suzuki-Miyaura reaction;	98%

3-Chloropyridine (626-60-8) + 2-Methylphenylboronic acid (16419-60-6) → 3-(p-methylphenyl)pyridine (90395-49-6)

Conditions	Yield
With potassium phosphate monohydrate; R-Phos; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 0.333333h; Suzuki-Miyaura reaction; Inert atmosphere;	100%
With NHC-Pd(II)-Im; potassium tert-butylate In water at 80℃; for 12h; Suzuki-Miyaura coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran; toluene at 100℃; for 10h; Suzuki-Miyaura reaction;	97%

para-bromotoluene (106-38-7) + 2-Methylphenylboronic acid (16419-60-6) → 2,4'-dimethylbiphenyl (611-61-0)

Conditions	Yield
With potassium phosphate; water In toluene at 100℃; for 1h; Suzuki coupling reaction;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 50℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium carbonate In water at 80℃; for 3h; Suzuki coupling;	99%

2-methylphenyl bromide (95-46-5) + 2-Methylphenylboronic acid (16419-60-6) → 2,2'-dimethyl-1,1'-biphenyl (605-39-0)

Conditions	Yield
With potassium phosphate monohydrate; R-Phos; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 1h; Suzuki coupling; Inert atmosphere;	100%
With dichloro bis(acetonitrile) palladium(II); C10H11N3S; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling; Schlenk technique; Inert atmosphere;	99%
With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 14h; Suzuki coupling;	98%

2-Methylphenylboronic acid (16419-60-6) + para-chloroacetophenone (99-91-2) → 4-acetyl-2'-methylbiphenyl (56917-39-6)

Conditions	Yield
With potassium fluoride; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 6h; Suzuki cross-coupling;	100%
With C38H53Cl2N2O2PPd*CH2Cl2; tetrabutylammomium bromide; potassium hydroxide In water at 80℃; for 6h; Suzuki-Miyaura Coupling; Schlenk technique;	100%
With caesium carbonate; palladium diacetate In toluene for 21h; Suzuki coupling; Heating;	99%

2-Methylphenylboronic acid (16419-60-6) + para-bromoacetophenone (99-90-1) → 4-acetyl-2'-methylbiphenyl (56917-39-6)

Conditions	Yield
With potassium phosphate; water In toluene at 100℃; for 1h; Suzuki coupling reaction;	100%
With potassium carbonate; N,N-diethylaminopropyl-Al2O3-Pd(OAc)2 In ethanol; water at 80℃; for 2h; Suzuki-Miyaura reaction; microwave irradiation;	100%
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura reaction; Inert atmosphere;	100%

2-Methylphenylboronic acid (16419-60-6) + 4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one (14628-57-0) → 5-methoxy-2-methyl-4-(2-methylphenyl)-3(2H)-pyridazinone (335349-37-6)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; Suzuki cross-coupling;	100%

bromobenzene (108-86-1) + 2-Methylphenylboronic acid (16419-60-6) → 2-methylbiphenyl (643-58-3)

Conditions	Yield
With potassium phosphate; water In toluene at 100℃; for 1h; Suzuki coupling reaction;	100%
With potassium phosphate tribasic trihydrate In ethanol; water at 50℃; for 1.25h; Suzuki coupling;	99%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 25℃; for 1h; Catalytic behavior; Suzuki Coupling; Microwave irradiation;	99%

2-Methylphenylboronic acid (16419-60-6) + 4-(N,N-diethylamino)benzenediazonium tetrafluoroborate (347-46-6) → 4-N,N-diethylamino-2'-methylbiphenyl

Conditions	Yield
[(1,3-dimesitylimidazol-2-ylidene)(naphthoquinone)Pd(0)]2 In methanol at 50℃; for 1h; Suzuki coupling;	100%

4-bromopyridin (1120-87-2) + 2-Methylphenylboronic acid (16419-60-6) → 4-(2-methylphenyl)pyridine (30456-66-7)

Conditions	Yield
With potassium phosphate; palladium-incarcerated polystyrene-based copolymer; tris(o-methoxyphenyl)phosphine In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;	100%
With potassium phosphate; tris(o-methoxyphenyl)phosphine; polymer-incarcerated palladium In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;	88%
With potassium phosphate tribasic trihydrate; trans-[(2-mesitylpy)2PdCl2] In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;	64%

4-methoxycarbonylphenyl bromide (619-42-1) + 2-Methylphenylboronic acid (16419-60-6) → 4-methyloxycarbonyl-2'-methyl-1,1'-biphenyl (89900-99-2)

Conditions	Yield
With potassium phosphate; tris(o-methoxyphenyl)phosphine; polymer-incarcerated palladium In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;	100%
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 6h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	88%

1-bromo-2,4,6-tri-tert-butylbenzene (3975-77-7) + 2-Methylphenylboronic acid (16419-60-6) → 1-methxyl-2-[2-methyl-2-(3,5-di-tert-buthylphenyl)propyl]benzene

Conditions	Yield
With potassium phosphate monohydrate; Ethyl 4-bromobenzoate; C52H49PRu; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 8h; Inert atmosphere;	100%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 18h; Suzuki-Miyaura coupling;	96%

2-Methylphenylboronic acid (16419-60-6) + 3-bromo-1-phenylsulfonyl indole (99655-68-2) → 3-(2-methylphenyl)-1-(phenylsulfonyl)-1H-indole (883141-48-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol; water for 18h; Suzuki-Miyaura coupling; Heating;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water Suzuki-Miyaura reaction; Reflux;	68%

2-Methylphenylboronic acid (16419-60-6) → Na{2-CH3-C6H4B(OH)3}

Conditions	Yield
With sodium hydroxide In toluene	100%

2-Methylphenylboronic acid (16419-60-6) + ortho-bromobenzaldehyde (6630-33-7) → 2'-methylbiphenyl-2-carboxaldehyde (7111-68-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate In tetrahydrofuran at 20℃; for 6h; Suzuki coupling; Inert atmosphere;	100%
With potassium phosphate monohydrate; 1‐ethyl‐2‐(1‐ethylindol-2-yl)benzoimidazole; palladium diacetate In 1,4-dioxane at 60℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	90%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide for 6h; Suzuki Coupling; Inert atmosphere; Reflux;	82%

2-chloro-5-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]pyridine (848952-90-9) + 2-Methylphenylboronic acid (16419-60-6) → 5-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-2-(2-methylphenyl)pyridine

Conditions	Yield
With caesium carbonate; [2-[(dimethylamino-kN)methyl]phenyl-kC](tricyclohexylphosphine)(trifluoroacetato-kO)-palladium In 1,4-dioxane at 20℃; for 21h; Heating / reflux;	100%

4-bromo-3-trifluoromethylbenzoic acid methyl ester (107317-58-8) + 2-Methylphenylboronic acid (16419-60-6) → methyl 2'-methyl-2-(trifluoromethyl)biphenyl-4-carboxylate (1140462-05-0)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 3h; Suzuki-Miyaura coupling; Reflux; Inert atmosphere;	100%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 3h; Heating / reflux;	80%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 3h; Inert atmosphere; Reflux;

methyl 3-(acetyloxy)methyl-4-bromobenzoate (254746-41-3) + 2-Methylphenylboronic acid (16419-60-6) → methyl 2-[(acetyloxy)methyl]-2'-methylbiphenyl-4-carboxylate (1140462-17-4)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 2h; Heating / reflux;	100%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 2h; Suzuki-Miyaura coupling; Reflux;

methyl 4-bromo-3-(methoxymethyl)benzoate (1141473-84-8) + 2-Methylphenylboronic acid (16419-60-6) → methyl 2-(methoxymethyl)-2’-methylbiphenyl-4-carboxylate (1141473-85-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 110℃; for 1h; Inert atmosphere;	100%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 1h; Heating / reflux;
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 1h; Suzuki-Miyaura coupling; Reflux; Inert atmosphere;
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene Inert atmosphere; Reflux;
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 1h; Suzuki-Miyura coupling; Inert atmosphere of N2; Reflux;

2-Methylphenylboronic acid (16419-60-6) → ortho-cresol (95-48-7)

Conditions	Yield
With 3,3'-dihexyloxy-1,1'-binaphthylidene-4,4'-dione; potassium hydroxide In tetrahydrofuran; water at 20℃;	100%
With dihydrogen peroxide at 20℃; for 0.25h; Green chemistry;	98%
With water; oxygen; sodium sulfite at 50℃; for 1h; Green chemistry;	97%

6-bromo-N-cyclohexyl-N-methylpyridin-2-amine (1225280-81-8) + 2-Methylphenylboronic acid (16419-60-6) → N-cyclohexyl-N-methyl-6-o-tolylpyridin-2-amine (1309609-65-1)

Conditions	Yield
With potassium phosphate; dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In toluene at 80℃; for 0.25h; Suzuki coupling;	100%

piperidine (110-89-4) + 2-Methylphenylboronic acid (16419-60-6) + Glyoxilic acid (298-12-4) → 2-(piperidin-1-yl)-2-o-tolylacetic acid (1017212-36-0)

Conditions	Yield
In dichloromethane at 20℃;	100%

3-bromobenzo[b]thiophene-2-carbaldehyde (10135-00-9) + 2-Methylphenylboronic acid (16419-60-6) → 3-o-tolylbenzo[b]thiophene-2-carbaldehyde (1393176-58-3)

Conditions	Yield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In water at 130℃; for 0.75h; Microwave irradiation; Inert atmosphere; Sealed tube;	100%

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 68971-87-9 (2-tolyl)tributyltin 
• 121-43-7 Trimethyl borate 
• 594-19-4 tert.-butyl lithium 
• 13283-31-3 borane 
• 5728-01-8 tetra-o-tolyltin 
• 2142-69-0 2-bromophenyl methyl ketone 
• 932-31-0 ortho-tolylmagnesium bromide 
• 5419-55-6 Triisopropyl borate 
• 616-99-9 bis(2-tolyl) mercury 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 7294-50-0 tri-o-tolylboroxine 
• 7732-18-5 water 
• 4250-48-0 (2-methylphenyl)dichloroborane 

Downstream Products

• 7294-50-0 tri-o-tolylboroxine 
• 91983-14-1 2-bromomethylphenylboronic acid 
• 112627-02-8 (2-Br₂CHC₆H₄)B(OH)2 
• 24341-76-2 (2-CH₃-3.5-(NO₂)2C₆H₂)B(OH)2 
• 93349-94-1 Methyl 5-(2-Methylphenyl)nicotinate 
• 90395-49-6 3-(p-methylphenyl)pyridine 
• 223462-87-1 4''''-iodo-2,2',2'',2''',3''''-pentamethyl-[1,1';4',4'';1'',1''';4''',1'''']quinquephenyl 
• 7111-77-5 2'-methyl[1,1'-biphenyl]-carboxylic acid 
• 59693-92-4 cyclohexyl 2-methylphenyl sulfide 
• 10273-89-9 2-(2-methylphenyl)pyridine 
• 5916-21-2 o-methyl-β,β-dimethylstyrene 
• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 10273-87-7 2,2',6'-trimethylbiphenyl 
• 56917-39-6 4-acetyl-2'-methylbiphenyl 

Relevant articles and documents

Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates

An efficient two-step procedure for the deprotection of pinacolyl organoboronate esters is described. Reaction with excess potassium hydrogen fluoride produces the corresponding stable, crystalline potassium organotrifluoroborate salts. Treatment of the trifluoroborates with either inorganic base or trimethylsilyl chloride and water affords the corresponding organoboronic acid in high yield.

Aryllead triacetates in the synthesis of oxaphenanthrene derivatives

Ortho-Halomethylphenyllead triacetates (halo = bromine or chlorine) react with phenols in the presence of triethylamine and a pyridine derivative to afford modest to good yields of dibenzo[b,d]-6H-pyrans.

Method for synthesizing sodium 2-carboxyphenylborate

The invention discloses a method for synthesizing sodium 2-carboxyphenylborate. The method comprises the following two steps of: 1) taking methyl 2-bromobenzoate as an initial raw material, through bromine removal by butyl lithium, carrying out a one-pot reaction with triisopropyl borate or trimethyl borate to obtain a product 2-methoxycarbonyl phenylboronic acid, and 2) hydrolyzing the 2-methoxycarbonyl phenylboronic acid in a sodium hydroxide methanol solution, and pulping with acetone to obtain sodium 2-carboxyphenylborate monohydrate. The method has the advantages of easily available raw materials, simple operation, safety, environmental protection, low cost and high yield.

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.

Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles

Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.