4-Tolylboronic acid supplier

Name
4-Tolylboronic acid
EINECS 611-480-1
CAS No. 5720-05-8
Article Data98
CAS DataBase
Density 1.1 g/cm³
Solubility It is soluble in water.
Melting Point 256-263 °C(lit.)
Formula C₇H₉BO₂
Boiling Point 275.2 °C at 760 mmHg
Molecular Weight 135.958
Flash Point 120.2 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Boronicacid, (4-methylphenyl)- (9CI);p-Tolueneboronic acid (7CI,8CI);(4-Methylphenyl)boronic acid;(p-Methylphenyl)boronic acid;4-Tolueneboronic acid;NSC62870;p-Methylbenzeneboronic acid;p-Tolylboronic acid;4-Methylphenylboronic acid;4-Tolylboronic acid;4-Methylphenylboronic Acid;p-Methyl phenylboronic Acid;
PSA 40.46000
LogP -0.32520

Synthetic route

: 13675-18-8
tetrahydroxydiboron

: 6140-15-4
trimethyl-p-tolylammonium iodide

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 121-43-7
Trimethyl borate

: 106-43-4
para-chlorotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

Conditions	Yield
With lithium In tetrahydrofuran	97.5%

: 22092-92-8
diisopropopylaminoborane

: 7732-18-5
water

: 4294-57-9
para-methylphenylmagnesium bromide

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

...Expand

: 195062-57-8
p-tolylboronic pinacol ester

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

: 40881-45-6
4-tolylboronic dimethyl ester

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 5419-55-6
Triisopropyl borate

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 5720-05-8
4-methylphenylboronic acid

Conditions

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℃;

: 106-49-0
p-toluidine

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 32203-14-8
2,3-dihydro-2-(4-methylphenyl)benzo[d][1,3,2]diazaborinin-4(1H)-one

A: 5720-05-8
4-methylphenylboronic acid

B: 28144-70-9
anthranilic acid amide

Conditions

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

: 121-43-7
Trimethyl borate

: 4294-57-9
para-methylphenylmagnesium bromide

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

: 29540-83-8
p-tolyl triflate

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

: 31614-66-1
tributyl(p-tolyl)stannane

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

: 624-31-7
4-tolyl iodide

: 5720-05-8
4-methylphenylboronic acid

Conditions

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;

: 121-43-7
Trimethyl borate

: 5419-55-6
Triisopropyl borate

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

...Expand

: 121-43-7
Trimethyl borate

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

: 13675-18-8
tetrahydroxydiboron

: 106-49-0
p-toluidine

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

: 67-56-1
methanol

: 55124-35-1
diisopropylamine borane

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

...Expand

: 7732-18-5
water

: potassium (4-methylphenyl)trifluoroborate

: 5720-05-8
4-methylphenylboronic acid

Conditions

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;

: 13675-18-8
tetrahydroxydiboron

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

Conditions

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℃;

: 104-92-7
1-bromo-4-methoxy-benzene

: 55124-35-1
diisopropylamine borane

: 106-38-7
para-bromotoluene

: 7732-18-5
water

A: 5720-05-8
4-methylphenylboronic acid

B: 5720-07-0
4-methoxyphenylboronic acid

C: B-(4-methoxyphenyl)-B-(4-methylphenyl)borinic acid

Conditions

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%

...Expand

: 13283-31-3
borane

: 4294-57-9
para-methylphenylmagnesium bromide

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 121-43-7
Trimethyl borate

: 106-38-7
para-bromotoluene

: 7439-95-4
magnesium

: 5720-05-8
4-methylphenylboronic acid

Conditions

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%

...Expand

: 5419-55-6
Triisopropyl borate

: C7H7BrMg*ZnCl2*LiCl

A: 5720-05-8
4-methylphenylboronic acid

B: 66117-64-4
di(p-tolyl)borinic acid

Conditions

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

...Expand

: 121-43-7
Trimethyl borate

: C7H7BrMg*ZnCl2*LiCl

: 5720-05-8
4-methylphenylboronic acid

Conditions

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

: 3796-24-5
4-trifluoromethylpyridine

: potassium (4-methylphenyl)trifluoroborate

A: 1246851-48-8
2-(p-tolyl)-4-(trifluoromethyl)pyridine

B: 5720-05-8
4-methylphenylboronic acid

Conditions

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

...Expand

: 121-43-7
Trimethyl borate

: C7H7BrMg*ZnCl2*LiCl

A: 5720-05-8
4-methylphenylboronic acid

B: 66117-64-4
di(p-tolyl)borinic acid

Conditions

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

...Expand

: 5419-55-6
Triisopropyl borate

: 106-43-4
para-chlorotoluene

A: 5720-05-8
4-methylphenylboronic acid

B: 108-88-3
toluene

Conditions

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

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

...Expand

: 873-32-5
2-Chlorobenzonitrile

: 5720-05-8
4-methylphenylboronic acid

: 114772-53-1
2-Cyano-4'-methylbiphenyl

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 99-90-1
para-bromoacetophenone

: 5748-38-9
4-acetyl-4'-methylbiphenyl

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 613-33-2
(4,4'-dimethyl-1,1'-biphenyl)

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 184042-10-2
4-bromo-N-(3-methyl-5-isoxazolyl)benzenesulfonamide

: 184036-44-0
4-(4-tolyl)-N-(3-methyl-5-isoxazolyl)benzenesulfonamide

Conditions

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%

: 108-86-1
bromobenzene

: 5720-05-8
4-methylphenylboronic acid

: 644-08-6
4-Methylbiphenyl

Conditions

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%

: 591-50-4
iodobenzene

: 5720-05-8
4-methylphenylboronic acid

: 644-08-6
4-Methylbiphenyl

Conditions

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%

: 624-31-7
4-tolyl iodide

: 5720-05-8
4-methylphenylboronic acid

: 613-33-2
(4,4'-dimethyl-1,1'-biphenyl)

Conditions

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%

: 142-08-5
2-Pyridone

: 5720-05-8
4-methylphenylboronic acid

: 19006-80-5
1-(4-methylphenyl)-1,2-dihydropyridin-2-one

Conditions

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%

: 104-92-7
1-bromo-4-methoxy-benzene

: 5720-05-8
4-methylphenylboronic acid

: 53040-92-9
4-(4-tolyl)anisole

Conditions

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%

: 2042-37-7
o-cyanobromobenzene

: 5720-05-8
4-methylphenylboronic acid

: 114772-53-1
2-Cyano-4'-methylbiphenyl

Conditions

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%

: 106-38-7
para-bromotoluene

: 5720-05-8
4-methylphenylboronic acid

: 613-33-2
(4,4'-dimethyl-1,1'-biphenyl)

Conditions

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%

: 696-62-8
para-iodoanisole

: 5720-05-8
4-methylphenylboronic acid

: 53040-92-9
4-(4-tolyl)anisole

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 188112-24-5
trifluoro-methanesulfonic acid 4-diisopropylcarbamoyl-phenyl ester

: 188112-26-7
N,N-diisopropyl-4'-methyl-[1,1'-biphenyl]-3-carboxamide

Conditions

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

: 930-68-7
cyclohexenone

: 5720-05-8
4-methylphenylboronic acid

: 99495-15-5
3-(p-tolyl)cyclohexan-1-one

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 100-44-7
benzyl chloride

: 620-83-7
1-methyl-4-(phenylmethyl)benzene

Conditions

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%

: 578-57-4
2-bromoanisole

: 5720-05-8
4-methylphenylboronic acid

: 92495-53-9
2-methoxy-4'-methylbiphenyl

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 176525-98-7
1-(1,1-dimethylethyl) 3-ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

: 1-tert-butyl 3-ethyl 4-(p-tolyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate

Conditions

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;

: 1666-13-3
diphenyl diselenide

: 5720-05-8
4-methylphenylboronic acid

: 83859-32-9
4-tolyl phenyl selenide

Conditions

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%

: 302-22-7
chlormadinone acetate

: 5720-05-8
4-methylphenylboronic acid

: 17-acetoxy-6-(4-methylphenyl)pregna-4,6-diene-3,20-dione

Conditions

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%

: 619-42-1
4-methoxycarbonylphenyl bromide

: 5720-05-8
4-methylphenylboronic acid

: 49742-56-5
methyl 4-(4-tolyl)benzoate

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: sodium (4-methylphenyltrihydroxyborate)

Conditions

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

: 930-68-7
cyclohexenone

: 5720-05-8
4-methylphenylboronic acid

: 610273-86-4
(R)-3-p-tolyl-cyclohexanone

Conditions

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

: 5720-05-8
4-methylphenylboronic acid

: 2-(2-thienyl)-3-(4-methylphenyl)-1H-inden-1-ol

Conditions

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

: 110-91-8
morpholine

: 59046-72-9
o-(phenylethynyl)benzaldehyde

: 5720-05-8
4-methylphenylboronic acid

: 3-morpholino-1-(4-methylphenyl)-2-phenyl-1H-indene

Conditions

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

...Expand

: 616878-80-9
2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

: 5720-05-8
4-methylphenylboronic acid

: 2-{4-[3,5-dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

Conditions

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

: 863783-61-3
3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

: 5720-05-8
4-methylphenylboronic acid

: 5,6-Dimethyl-3-(6-p-tolyl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions

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

: 863783-73-7
3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

: 5720-05-8
4-methylphenylboronic acid

: 5,6-Dimethyl-3-(7-p-tolyl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions

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

: 5720-05-8
4-methylphenylboronic acid

: 2-fluoro-6-[(3-methoxy-4'-methylbiphenyl-4-yl)oxy]pyridine

Conditions

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%

: 5720-05-8
4-methylphenylboronic acid

: 67718-18-7
2-chloro-6-phenyl-furo[2,3-b]pyrazine

: 1011736-51-8
C19H14N2O

Conditions

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%

: 637-87-6
1-Chloro-4-iodobenzene

: 5720-05-8
4-methylphenylboronic acid

: 19482-11-2
4-chloro-4'-methylbiphenyl

Conditions

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%

4-Tolylboronic acid Specification

The 4-Tolylboronic acid, with the CAS registry number 5720-05-8, is also known as 4-Methylphenylboric acid. It belongs to the product categories of Blocks; Boronic Acids; Substituted Boronic Acids; Boronic Acids; Boronic Acid; Aryl; Organoborons; B (Classes of Boron Compounds); Chiral Chemicals; Benzene Derivatives. This chemical's molecular formula is C₇H₉BO₂ and molecular weight is 135.95616. Its IUPAC name is called (4-methylphenyl)boronic acid. What's more, the product should be sealed and stored in cool and dry place at 0-6 °C.

Physical properties of 4-Tolylboronic acid: (1)ACD/LogP: 2.05; (2)ACD/LogD (pH 5.5): 2.05; (3)ACD/LogD (pH 7.4): 2.03; (4)ACD/BCF (pH 5.5): 21.25; (5)ACD/BCF (pH 7.4): 20.52; (6)ACD/KOC (pH 5.5): 310.21; (7)ACD/KOC (pH 7.4): 299.58; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.527; (12)Molar Refractivity: 37.91 cm³; (13)Molar Volume: 123.1 cm³; (14)Surface Tension: 40.1 dyne/cm; (15)Density: 1.1 g/cm³; (16)Flash Point: 120.2 °C; (17)Enthalpy of Vaporization: 54.26 kJ/mol; (18)Boiling Point: 275.2 °C at 760 mmHg; (19)Vapour Pressure: 0.0025 mmHg at 25°C.

Uses of 4-Tolylboronic acid: it can be used to produce 3,5-dimethyl-4-p-tolyl-isoxazole with 4-iodo-3,5-dimethyl-isoxazole at temperature of 80 °C. This reaction will need reagents (PPh₃)₂PdCl₂, NaHCO₃ and solvents 1,2-dimethoxy-ethane, H₂O with reaction time of 18 hours. The yield is about 98%.

4-Tolylboronic acid can be used to produce 3,5-dimethyl-4-p-tolyl-isoxazole with 4-iodo-3,5-dimethyl-isoxazole

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: B(C1=CC=C(C=C1)C)(O)O
(2)InChI: InChI=1S/C7H9BO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5,9-10H,1H3
(3)InChIKey: BIWQNIMLAISTBV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	172mg/kg (172mg/kg)		Acta Physiologica Polonica. Vol. 12, Pg. 173, 1961.

Product Name

4-Tolylboronic acid

Synthetic route

4-Tolylboronic acid Specification

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