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5720-05-8

Basic Information
CAS No.: 5720-05-8
Name: Boronic acid,B-(4-methylphenyl)-
Molecular Structure:
Molecular Structure of 5720-05-8 (Boronic acid,B-(4-methylphenyl)-)
Formula: C7H9BO2
Molecular Weight: 135.96
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;
EINECS: 611-480-1
Density: 1.1 g/cm3
Melting Point: 256-263 °C(lit.)
Boiling Point: 275.2 °C at 760 mmHg
Flash Point: 120.2 °C
Solubility: It is soluble in water.
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
Transport Information:
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
ConditionsYield
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
ConditionsYield
With lithium In tetrahydrofuran97.5%
22092-92-8

diisopropopylaminoborane

4294-57-9

para-methylphenylmagnesium bromide

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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%
195062-57-8

p-tolylboronic pinacol ester

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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
ConditionsYield
With hydrogenchloride In water91%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With borane; water In tetrahydrofuran for 1h; Heating;85%
106-38-7

para-bromotoluene

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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 tetrahydrofuran80%
624-31-7

4-tolyl iodide

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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
ConditionsYield
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%
121-43-7

Trimethyl borate

106-38-7

para-bromotoluene

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
With Mg; I2 In tetrahydrofuran80%
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
ConditionsYield
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
ConditionsYield
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%

potassium (4-methylphenyl)trifluoroborate

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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
ConditionsYield
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

A

5720-05-8

4-methylphenylboronic acid

B

5720-07-0

4-methoxyphenylboronic acid

C

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

Conditions
ConditionsYield
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%
4294-57-9

para-methylphenylmagnesium bromide

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;A 67%
B 15%
121-43-7

Trimethyl borate

C7H7BrMg*ZnCl2*LiCl

5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
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
ConditionsYield
With dipotassium peroxodisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water; water-d2 at 20℃; for 4h; Mechanism; Inert atmosphere;A 60%
B n/a
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
ConditionsYield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;A 52%
B 18%
5419-55-6

Triisopropyl borate

106-43-4

para-chlorotoluene

A

5720-05-8

4-methylphenylboronic acid

B

108-88-3

toluene

Conditions
ConditionsYield
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
873-32-5

2-Chlorobenzonitrile

5720-05-8

4-methylphenylboronic acid

114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium hydroxide In toluene100%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With tricyclohexylphosphine; allyl(cyclopentadiene)palladium(II) In N,N-dimethyl-formamide at 80℃; for 1h;100%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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    4-Methylphenylboronic acid

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    4-Tolylboronic acid CAS No.:5720-05-8 Name: 4-Tolylboronic acid Synonyms: 4-Methylphenylboronic acid Molecular Structure Molecular

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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.