5720-05-8

Basic information

• Product Name: 4-Tolylboronic acid
• Synonyms: 4-METHYLBENZENEBORONIC ACID;4-METHYLPHENYLBORIC ACID;4-METHYLPHENYLBORONIC ACID;P-METHYLPHENYLBORONIC ACID;P-TOLYLBORONIC ACID;RARECHEM AH PB 0227;TOLUENE-4-BORONIC ACID;(4-methylphenyl)-boronicaci
• CAS NO: 5720-05-8
• Molecular Formula: C₇H₉BO₂
• Molecular Weight: 135.96
• EINECS: 202-766-3
• Product Categories: blocks;BoronicAcids;Substituted Boronic Acids;Boronic acids;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);CHIRAL CHEMICALS;Benzene derivatives;organic or inorganic borate;OLED materials,pharm chemical,electronic;Boronate Ester;Potassium Trifluoroborate;Liquid crystal intermediates
• Mol File: 5720-05-8.mol
• Article Data: 86

Chemical Properties

• Melting Point: 256-263 °C(lit.)
• Boiling Point: 275.2 °C at 760 mmHg
• Flash Point: 120.2 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.1 g/cm³
• Vapor Pressure: 0.976mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.84±0.10(Predicted)
• Water Solubility: It is soluble in water.
• BRN: 2935970
• CAS DataBase Reference: 4-Tolylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Tolylboronic acid(5720-05-8)
• EPA Substance Registry System: 4-Tolylboronic acid(5720-05-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: XS7400000
• HazardClass: IRRITANT
• Hazardous Substances Data: 5720-05-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 5720-05-8 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Methylbenzeneboronic acid, is a commonly used chemical in Suzuki coupling reactions. It is also used as an intermediate in pharmaceutical industry
3. Reagent used forPalladium (Pd)-catalyzed direct arylationDirect Palladium(II)-Catalyzed SynthesisPalladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in waterCyclopalladationTandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequenceRuthenium catalyzed direct arylationRhodium-catalyzed asymmetric conjugate additionLigand-free copper-catalyzed cross-coupling reactionsRegioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactionsLigand-free Suzuki, Sonogashira, and Heck cross-coupling reactionsReagent used in Preparation ofCatalysts for Suzuki-Miyaura cross-coupling of aryl bromidesRecyclable Palladium nanoparticle catalysts immobilized by click ionic copolymers as for Suzuki-Miyaura cross-coupling reactions in water

InChI:InChI=1/C9H13N/c1-8(10-2)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-/m1/s1

Synthetic route

tetrahydroxydiboron (13675-18-8) + trimethyl-p-tolylammonium iodide (6140-15-4) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	98%

Trimethyl borate (121-43-7) + para-chlorotoluene (106-43-4) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With lithium In tetrahydrofuran	97.5%

diisopropopylaminoborane (22092-92-8) + water (7732-18-5) + para-methylphenylmagnesium bromide (4294-57-9) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: diisopropopylaminoborane; para-methylphenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere;	95%

p-tolylboronic pinacol ester (195062-57-8) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h;	94%
Stage #1: p-tolylboronic pinacol ester With potassium hydrogen difluoride In methanol at 20℃; for 0.25h; Stage #2: With lithium hydroxide In acetonitrile at 20℃; for 20h;	85%

4-tolylboronic dimethyl ester (40881-45-6) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With hydrogenchloride In water	91%
With hydrogenchloride In tetrahydrofuran; water for 5h;	55%
With sulfuric acid In tetrahydrofuran

Triisopropyl borate (5419-55-6) + para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 70℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran at 0℃; for 1h; Temperature; Concentration; Time;	91%
With magnesium; ethylene dibromide In tetrahydrofuran at 40 - 60℃; for 6h; Inert atmosphere;	58%
Stage #1: para-bromotoluene With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃;	52%
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane
Stage #1: para-bromotoluene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 25℃; for 0.333333h; Inert atmosphere;

potassium (4-methylphenyl)trifluoroborate → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With aluminum oxide; water at 70℃; for 0.25h; Microwave irradiation;	90%
With water; silica gel at 20℃; for 1h; Inert atmosphere;	76%
With water In tetrahydrofuran at 55℃; Kinetics; Reagent/catalyst;
With silica gel; sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃;

p-toluidine (106-49-0) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite In methanol; water at 0 - 5℃; for 0.5h; Stage #2: With tetrahydroxydiboron In methanol; water at 20℃; for 1h;	90%
Multi-step reaction with 3 steps 1.1: tetrafluoroboric acid / water / 0.17 h / 0 °C 1.2: 1 h / 0 °C 1.3: 20 °C / Inert atmosphere 2.1: 1 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / water View Scheme

2,3-dihydro-2-(4-methylphenyl)benzo[d][1,3,2]diazaborinin-4(1H)-one (32203-14-8) → 4-methylphenylboronic acid (5720-05-8) + anthranilic acid amide (28144-70-9)

Conditions	Yield
In 1,4-dioxane; water at 140℃; for 0.5h; Microwave irradiation; Sealed tube;	A 78% B 88%

Trimethyl borate (121-43-7) + para-methylphenylmagnesium bromide (4294-57-9) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
In tetrahydrofuran dropwise addn. of p-tolylmagnesium bromide to borane at -70°C; stirred below -60°C for 1 h; hydrolyzed (sulfuric acid); filtration; sepn. of org. layer; extn. of aq. layer (ether); combined org. layer washed (H2O); dried (Na2SO4); concn. of soln.; crystn.; washed (hexane, H2O); IR; NMR; mass spectra;	86%

p-tolyl triflate (29540-83-8) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: p-tolyl 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;	86%

tributyl(p-tolyl)stannane (31614-66-1) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With borane; water In tetrahydrofuran for 1h; Heating;	85%

para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: para-bromotoluene With magnesium In tetrahydrofuran Heating; Stage #2: With Trimethyl borate In tetrahydrofuran; diethyl ether at 20℃; for 2h; Stage #3: With hydrogenchloride In tetrahydrofuran; diethyl ether for 1h;	85%
Stage #1: para-bromotoluene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 10℃; Inert atmosphere;	85%
With Trimethyl borate; iodine; magnesium In tetrahydrofuran	80%

4-tolyl iodide (624-31-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: 4-tolyl 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;	84%
(i) (UV-irradiation), BBr3, (ii) aq. NaOH; Multistep reaction;

Trimethyl borate (121-43-7) + Triisopropyl borate (5419-55-6) + para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: Triisopropyl borate; para-bromotoluene With magnesium; ethylene dibromide In tetrahydrofuran at 40 - 60℃; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran for 6h; Inert atmosphere; Reflux;	81%

Trimethyl borate (121-43-7) + para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With Mg; I2 In tetrahydrofuran	80%
Stage #1: para-bromotoluene With magnesium In diethyl ether for 3 - 4h; Reflux; Stage #2: Trimethyl borate In diethyl ether at -12 - 20℃;	76%
With magnesium In tetrahydrofuran 1) Mg, THF, reflux; 2) B(OMe)3, THF, -78 to 23°C;	72%

tetrahydroxydiboron (13675-18-8) + p-toluidine (106-49-0) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: p-toluidine With hydrogenchloride In water at 20℃; for 0.0166667h; Stage #2: With sodium nitrite In water at 0℃; for 0.25h; Stage #3: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;	78%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: para-bromotoluene In tetrahydrofuran at 70℃; Stage #3: methanol Further stages;	78%

water (7732-18-5) + potassium (4-methylphenyl)trifluoroborate → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With 1H-imidazole; iron(III) chloride at 20℃; for 0.25h; Inert atmosphere;	76%
With glass or Cs2CO3 In tetrahydrofuran; water Kinetics; hydrolysis at 55°C in THF/H2O in the presence of glass powder or Cs2CO3; not isolated;

tetrahydroxydiboron (13675-18-8) + para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	76%
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; sodium acetate In dichloromethane; water at 40℃; for 6h; Inert atmosphere;
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4h; Miyaura Borylation Reaction; Schlenk technique; Inert atmosphere; Sealed tube;
With potassium tert-butylate In methanol at 0 - 20℃;

1-bromo-4-methoxy-benzene (104-92-7) + diisopropylamine borane (55124-35-1) + para-bromotoluene (106-38-7) + water (7732-18-5) → 4-methylphenylboronic acid (5720-05-8) + 4-methoxyphenylboronic acid (5720-07-0) + B-(4-methoxyphenyl)-B-(4-methylphenyl)borinic acid

Conditions	Yield
Stage #1: diisopropylamine borane; para-bromotoluene With magnesium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: 1-bromo-4-methoxy-benzene In tetrahydrofuran at 40℃; for 14h; Inert atmosphere; Stage #3: water In tetrahydrofuran Temperature; Inert atmosphere;	A 9% B 12% C 73%

borane (13283-31-3) + para-methylphenylmagnesium bromide (4294-57-9) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With water In tetrahydrofuran slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;	71%

Cedranediol p-tolylboronate → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
Stage #1: Cedranediol p-tolylboronate With 2,2'-iminobis[ethanol] Stage #2: With hydrogenchloride for 0.5h;	70%

Trimethyl borate (121-43-7) + para-bromotoluene (106-38-7) + magnesium (7439-95-4) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran (Ar); stirring (-30°C), stirring (room temp., overnight), hydrolysis (0°C, water, 4M HCl), evapn. of the solvent, extn. (ether); evapn. of the solvent, recrystn. (water); elem. anal.;	70%

Triisopropyl borate (5419-55-6) + C7H7BrMg*ZnCl2*LiCl → 4-methylphenylboronic acid (5720-05-8) + di(p-tolyl)borinic acid (66117-64-4)

Conditions	Yield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;	A 67% B 15%

Trimethyl borate (121-43-7) + C7H7BrMg*ZnCl2*LiCl → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Reagent/catalyst; Schlenk technique; Inert atmosphere;	63%

4-trifluoromethylpyridine (3796-24-5) + potassium (4-methylphenyl)trifluoroborate → 2-(p-tolyl)-4-(trifluoromethyl)pyridine (1246851-48-8) + 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water; water-d2 at 20℃; for 4h; Mechanism; Inert atmosphere;	A 60% B n/a

Trimethyl borate (121-43-7) + C7H7BrMg*ZnCl2*LiCl → 4-methylphenylboronic acid (5720-05-8) + di(p-tolyl)borinic acid (66117-64-4)

Conditions	Yield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;	A 52% B 18%

Triisopropyl borate (5419-55-6) + para-chlorotoluene (106-43-4) → 4-methylphenylboronic acid (5720-05-8) + toluene (108-88-3)

Conditions

Yield

With magnesium In tetrahydrofuran byproducts: Mg(2+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in THF containing (CF3SO2)2NLi, solvent and excess B(OiPr)3 evaporated under vacuum, medium hydrolysed at 0°C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), organic phase dried over sodium or magnesium sulfate and concentrated under vacuum, side product phenol formation avoided by work-up under inert atmosphere;

A 46% B n/a

2-Chlorobenzonitrile (873-32-5) + 4-methylphenylboronic acid (5720-05-8) → 2-Cyano-4'-methylbiphenyl (114772-53-1)

Conditions	Yield
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In n-heptane; water at 60℃; for 1.66667h; Suzuki Coupling; Inert atmosphere;	100%
With potassium carbonate In water; isopropyl alcohol at 100℃; for 7h; Catalytic behavior; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide; tetra(n-butyl)ammonium hydroxide; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 0.666667h; Suzuki-Miyaura coupling; Microwave irradiation;	99%

4-methylphenylboronic acid (5720-05-8) + para-bromoacetophenone (99-90-1) → 4-acetyl-4'-methylbiphenyl (5748-38-9)

Conditions	Yield
With C23H35N4O4Pd(1+)*Br(1-); potassium carbonate In water at 100℃; for 1h; Suzuki-Miyaura Coupling;	100%
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 5h; Suzuki Coupling;	100%
With potassium carbonate In water at 80℃; for 10.5h; Suzuki-Miyaura Coupling; Green chemistry;	100%

4-methylphenylboronic acid (5720-05-8) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2)

Conditions	Yield
With air; palladium diacetate In methanol at 20℃; for 5h;	100%
With p-benzoquinone; (IPr)Pd(OAc)2(H2O) In methanol at 20℃; for 24h;	100%
With sodium hydroxide In water at 120 - 130℃; Microwave irradiation;	99%

4-methylphenylboronic acid (5720-05-8) + 4-bromo-N-(3-methyl-5-isoxazolyl)benzenesulfonamide (184042-10-2) → 4-(4-tolyl)-N-(3-methyl-5-isoxazolyl)benzenesulfonamide (184036-44-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 24h; Suzuki coupling;	100%
With sodium carbonate; tetrakis (triphenylphosphine)palladium (O) In ethanol; toluene at 80℃; for 24h; biphasic mixture;	100%

bromobenzene (108-86-1) + 4-methylphenylboronic acid (5720-05-8) → 4-Methylbiphenyl (644-08-6)

Conditions	Yield
With potassium carbonate; palladium dichloride In pyridine for 3h; Suzuki cross-coupling; Heating;	100%
With potassium carbonate; carbapalladacycle complex*periodic mesoporous organosilica for 24h; Suzuki coupling; Heating;	100%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation;	100%

iodobenzene (591-50-4) + 4-methylphenylboronic acid (5720-05-8) → 4-Methylbiphenyl (644-08-6)

Conditions	Yield
With potassium carbonate In water at 80℃; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;	100%
With aluminum oxide; potassium fluoride; palladium at 100℃; for 4h; Suzuki reaction;	99%
With sodium hydroxide; tetrabutylammomium bromide; palladium on activated charcoal at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	99%

4-tolyl iodide (624-31-7) + 4-methylphenylboronic acid (5720-05-8) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2)

Conditions	Yield
With sodium carbonate In ethanol; water at 80℃; for 0.166667h; Catalytic behavior; Suzuki-Miyaura Coupling;	100%
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium phosphate tribasic trihydrate In ethanol; water at 60℃; for 0.166667h; Suzuki-Miyaura cross-coupling reaction;	99%

2-Pyridone (142-08-5) + 4-methylphenylboronic acid (5720-05-8) → 1-(4-methylphenyl)-1,2-dihydropyridin-2-one (19006-80-5)

Conditions	Yield
With pyridine; 4 Angstroem MS; oxygen; copper diacetate In dichloromethane at 20℃;	100%
With pyridine; copper diacetate; 4 A molecular sieve In dichloromethane at 20℃; for 48h; Arylation;	75%
With copper diacetate; 4 A molecular sieve; triethylamine In pyridine; dichloromethane at 20℃; for 48h; Arylation;	38%

1-bromo-4-methoxy-benzene (104-92-7) + 4-methylphenylboronic acid (5720-05-8) → 4-(4-tolyl)anisole (53040-92-9)

Conditions	Yield
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.166667h; Suzuki-Miyaura reaction;	100%
With sodium carbonate; polystyrene-supported N-heterocyclic carbene-Pd catalyst In N,N-dimethyl-formamide at 20℃; for 24h; Suzuki reaction;	99%
With C28H38Cl2N2O6PdS2(2-)*2Na(1+); potassium carbonate In ethanol; water at 70℃; for 1.5h; Suzuki coupling;	99%

o-cyanobromobenzene (2042-37-7) + 4-methylphenylboronic acid (5720-05-8) → 2-Cyano-4'-methylbiphenyl (114772-53-1)

Conditions	Yield
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; [1-cyclohexyl-3-(di-pyridin-2-yl-methyl)-urea][PdCl2] In water at 100℃; for 1h; Suzuki-Miyaura coupling;	99%
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.0833333h; Suzuki cross-coupling reaction;	99%

para-bromotoluene (106-38-7) + 4-methylphenylboronic acid (5720-05-8) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2)

Conditions	Yield
With potassium carbonate; palladium dichloride In pyridine for 4h; Suzuki cross-coupling; Heating;	100%
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 12h; Suzuki cross-coupling;	100%
With potassium phosphate; [Pd(Ph2PCH2CH(CH3)O)2] In tetrahydrofuran; water at 20℃; for 5h; Suzuki cross-coupling reaction;	99%

para-iodoanisole (696-62-8) + 4-methylphenylboronic acid (5720-05-8) → 4-(4-tolyl)anisole (53040-92-9)

Conditions	Yield
With potassium carbonate In water at 80℃; for 2h; Suzuki Coupling;	100%
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;	99%
With water; triethylamine; Pd(OAc)2EnCatTM In N,N-dimethyl-formamide at 120℃; for 0.25h; Suzuki-Miyaura reaction; microwave irradiation;	99%

4-methylphenylboronic acid (5720-05-8) + trifluoro-methanesulfonic acid 4-diisopropylcarbamoyl-phenyl ester (188112-24-5) → N,N-diisopropyl-4'-methyl-[1,1'-biphenyl]-3-carboxamide (188112-26-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride In ethanol; toluene Heating;	100%

cyclohexenone (930-68-7) + 4-methylphenylboronic acid (5720-05-8) → 3-(p-tolyl)cyclohexan-1-one (99495-15-5)

Conditions	Yield
With chloroform; caesium carbonate; triphenylphosphine; palladium diacetate In toluene at 80℃; for 24h;	100%
[Rh(OH)(cod)]2; β‐cyclodextrin In water at 50℃; for 6h; Product distribution; Further Variations:; Catalysts; Reaction partners; Temperatures;	99%
With 1,5-cis,cis-cyclooctadiene; rhodium-grafted hydrotalcite In 1,4-dioxane at 100℃; for 4h;	99%

4-methylphenylboronic acid (5720-05-8) + benzyl chloride (100-44-7) → 1-methyl-4-(phenylmethyl)benzene (620-83-7)

Conditions	Yield
With potassium phosphate; SP-4-[1,3-bis[2,6-diisopropylphenyl]-1,3-dihydro-2H-imidazol-2-ylidene]chloro[2-(1-methyl-1H-imidazol-2-yl-κN3)phenyl-κC]palladium(II) In ethanol at 60℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium phosphate tribasic trihydrate In ethanol at 80℃; for 0.166667h; Catalytic behavior; Suzuki-Miyaura Coupling;	99%
With C34H41Cl2N3OPd; potassium tert-butylate In water; isopropyl alcohol at 80℃; for 15h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%

2-bromoanisole (578-57-4) + 4-methylphenylboronic acid (5720-05-8) → 2-methoxy-4'-methylbiphenyl (92495-53-9)

Conditions	Yield
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.25h; Suzuki-Miyaura reaction;	100%
With Pd/C; potassium carbonate In ethanol; water at 100℃; for 3h; Suzuki-Miyaura Coupling;	95%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 25℃; for 1h; Catalytic behavior; Suzuki Coupling; Microwave irradiation;	94%

4-methylphenylboronic acid (5720-05-8) + 1-(1,1-dimethylethyl) 3-ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate (176525-98-7) → 1-tert-butyl 3-ethyl 4-(p-tolyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 4h; Inert atmosphere; Reflux;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate In ethanol at 80℃; Suzuki-Miyaura cross-coupling;

diphenyl diselenide (1666-13-3) + 4-methylphenylboronic acid (5720-05-8) → 4-tolyl phenyl selenide (83859-32-9)

Conditions	Yield
With Cu NPs/Ac In dimethyl sulfoxide at 20 - 100℃; for 4h; Sealed tube; Sonication;	100%
With [2,2]bipyridinyl; copper(l) iodide In water; dimethyl sulfoxide at 100℃; for 12h;	98%
With silver nitrate In 1,4-dioxane at 100℃; for 6h;	96%

chlormadinone acetate (302-22-7) + 4-methylphenylboronic acid (5720-05-8) → 17-acetoxy-6-(4-methylphenyl)pregna-4,6-diene-3,20-dione

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 100℃; for 13h; Suzuki-Miyaura coupling;	100%
With potassium carbonate; PdCl2(PPh2(CH2)4PPh2) In toluene at 100℃; for 13h; Suzuki-Miyaura cross-coupling;	100%

4-methoxycarbonylphenyl bromide (619-42-1) + 4-methylphenylboronic acid (5720-05-8) → methyl 4-(4-tolyl)benzoate (49742-56-5)

Conditions	Yield
With potassium phosphate; second generation phosphine dendrimer-stabilized palladium In 1,4-dioxane for 20h; Suzuki coupling; Heating;	100%
With sodium carbonate; bis(dibenzylideneacetone)-palladium(0); C78H99N6P(6+)*6Br(1-) In methanol; water at 65℃; for 3h; Reactivity; Kinetics; Reagent/catalyst; Time; Suzuki-Miyaura cross-coupling; Inert atmosphere;	100%
With potassium phosphate tribasic heptahydrate In 1,4-dioxane for 20h; Suzuki coupling; Reflux;	100%

4-methylphenylboronic acid (5720-05-8) → sodium (4-methylphenyltrihydroxyborate)

Conditions	Yield
With sodium hydroxide In toluene	100%
With sodium hydroxide In water; toluene Reflux;

cyclohexenone (930-68-7) + 4-methylphenylboronic acid (5720-05-8) → (R)-3-p-tolyl-cyclohexanone (610273-86-4)

Conditions	Yield
With potassium hydroxide; [{Rh(C2H4)2Cl}2]; (1-methyl-1-phenylethyl)cyclohexanol biphenol phosphite In 1,4-dioxane; water at 23℃; for 15h;	100%
With BF4(1-)*C68H44N2O4P2Rh(1+); water; potassium hydroxide In 1,4-dioxane at 60℃; for 1h; Anaerobic conditions; Combinatorial reaction / High throughput screening (HTS); optical yield given as %ee; enantioselective reaction;	99%
Stage #1: 4-methylphenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; C21H26O4S In tetrahydrofuran at 60℃; for 0.5h; Inert atmosphere; Stage #2: cyclohexenone With potassium dihydrogenphosphate In tetrahydrofuran; water at 60℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

2-(thiophen-2-ylethynyl)-benzaldehyde + 4-methylphenylboronic acid (5720-05-8) → 2-(2-thienyl)-3-(4-methylphenyl)-1H-inden-1-ol

Conditions	Yield
With tricyclohexylphosphine; tris(dibenzylideneacetone)dipalladium (0) In methanol at 100℃; for 5h;	100%

morpholine (110-91-8) + o-(phenylethynyl)benzaldehyde (59046-72-9) + 4-methylphenylboronic acid (5720-05-8) → 3-morpholino-1-(4-methylphenyl)-2-phenyl-1H-indene

Conditions	Yield
With tricyclohexylphosphine; allyl(cyclopentadiene)palladium(II) In N,N-dimethyl-formamide at 80℃; for 1h;	100%

2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (616878-80-9) + 4-methylphenylboronic acid (5720-05-8) → 2-{4-[3,5-dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

Conditions	Yield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; water for 16h; Heating / reflux;	100%

3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-61-3) + 4-methylphenylboronic acid (5720-05-8) → 5,6-Dimethyl-3-(6-p-tolyl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 3h;	100%

3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-73-7) + 4-methylphenylboronic acid (5720-05-8) → 5,6-Dimethyl-3-(7-p-tolyl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 1h;	100%

2-(4-chloro-2-methoxyphenoxy)-6-fluoropyridine + 4-methylphenylboronic acid (5720-05-8) → 2-fluoro-6-[(3-methoxy-4'-methylbiphenyl-4-yl)oxy]pyridine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 105℃; for 48h;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 105℃; for 48h; Inert atmosphere;	100%

4-methylphenylboronic acid (5720-05-8) + 2-chloro-6-phenyl-furo[2,3-b]pyrazine (67718-18-7) → C19H14N2O (1011736-51-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki coupling; microwave irradiation;	100%

1-Chloro-4-iodobenzene (637-87-6) + 4-methylphenylboronic acid (5720-05-8) → 4-chloro-4'-methylbiphenyl (19482-11-2)

Conditions	Yield
With potassium phosphate; tetrabutylammomium bromide In 1,4-dioxane; water at 120℃; for 2h; Suzuki Coupling; Inert atmosphere;	100%
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Catalytic behavior; Suzuki-Miyaura Coupling; Irradiation;	99%
With sodium hydroxide In ethanol; water at 25℃; for 3h; Suzuki Coupling;	94%

Upstream product

• 4250-45-7 dichloro-p-tolyl-borane 
• 66117-64-4 di(p-tolyl)borinic acid 
• 13195-76-1 triisobutyl borate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 688-74-4 boric acid tributyl ester 
• 624-31-7 4-tolyl iodide 
• 2417-95-0 p-tolyllithium 
• 7732-18-5 water 
• 4151-78-4 4-(dibromoboryl)toluene 
• 5084-80-0 tri(4-tolyl)boroxine 
• 106-38-7 para-bromotoluene 
• 106-43-4 para-chlorotoluene 
• 19287-45-7 diborane 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 40881-45-6 4-tolylboronic dimethyl ester 
• 32212-14-9 4-(4-chloro-phenyl)-2-p-tolyl-2,3-dihydro-[1,3,5,2]oxadiazaborole 
• 32203-14-8 2,3-dihydro-2-(4-methylphenyl)benzo[d][1,3,2]diazaborinin-4(1H)-one 
• 152684-18-9 3-methoxy-5-(4-methylphenyl)-2-nitropyridine 
• 644-08-6 4-Methylbiphenyl 
• 152609-42-2 1-(benzyloxy)-4-ethyl-5-<(6-methyl-6-cyanoheptyl)oxy>-2-(4-methylphenyl)benzene 
• 172975-76-7 N-(4-Methyl-[1,1';3',1'']terphenyl-2'-ylmethyl)-benzamide 
• 172975-83-6 N-(4-Chloro-4''-methyl-[1,1';3',1'']terphenyl-2'-ylmethyl)-benzamide 
• 174575-30-5 (2S,5S)-5-[4-Acetoxy-5-(diethoxy-phosphorylmethyl)-4'-methyl-biphenyl-3-ylmethyl]-2-tert-butyl-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester 
• 2143-88-6 4-nitro-4'-methyl-1,1'-biphenyl 
• 146012-94-4 3-bromo-4-(4-methylphenyl)thiophene 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 7148-03-0 o-tolylbenzoic acid 

Relevant articles and documents

Atropisomerism of the C-1-C′-1 axis of 2,2′,8,8′-unsubstituted 1,1′-binaphthyl derivatives

The Suzuki coupling of optically active (S)-binaphthyl bromide 10 with (S)-binaphthyl boronic acid 11 produced a diastereomeric mixture of tetrahydroxyquaternaphthyls 4. The coupling products 4 as well as their derivatives 5-7 can be considered as members of the family of 1,1′-binaphthyl-3,3′-diols. The C-1-C′-1 axis of all these compounds was found to have an unusually high rotational barrier. Generally, the barrier is higher for derivatives having more bulky substituents at the 3 and 3′ positions.

Bipyridinium and Phenanthrolinium Dications for Metal-Free Hydrodefluorination: Distinctive Carbon-Based Reactivity

The development of novel Lewis acids derived from bipyridinium and phenanthrolinium dications is reported. Calculations of Hydride Ion Affinity (HIA) values indicate high carbon-based Lewis acidity at the ortho and para positions. This arises in part from extensive LUMO delocalization across the aromatic backbones. Species [C10H6R2N2CH2CH2]2+ (R=H [1 a]2+, Me [1 f]2+, tBu [1 g]2+), and [C12H4R4N2CH2CH2]2+ (R=H [2 a]2+, Me [2 b]2+) were prepared and evaluated for use in the initiation of hydrodefluorination (HDF) catalysis. Compound [2 a]2+ proved highly effective towards generating catalytically active silylium cations via Lewis acid-mediated hydride abstraction from silane. This enabled the HDF of a range of aryl- and alkyl- substituted sp3(C?F) bonds under mild conditions. The protocol was also adapted to effect the deuterodefluorination of cis-2,4,6-(CF3)3C6H9. The dications are shown to act as hydride acceptors with the isolation of neutral species C16H14N2 (3 a) and C16H10Me4N2 (3 b) and monocationic species [C14H13N2]+ ([4 a]+) and [C18H21N2]+ ([4 b]+). Experimental and computational data provide further support that the dications are initiators in the generation of silylium cations.

Palladium-catalyzed B-diarylation of diethylaminoborane for the synthesis of diarylborinic acids

The palladium-catalyzed synthesis of diarylborinic acid derivatives by intermolecular cross-coupling between aryl iodides and (amino)dihydrideborane is reported. The key to success of the reaction is the use of a less bulky diethylaminoborane reagent, which facilitates the second B-arylation.