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5720-05-8

Basic Information
CAS No.: 5720-05-8
Name: 4-Tolylboronic acid
Article Data: 98
Molecular Structure:
Molecular Structure of 5720-05-8 (4-Tolylboronic acid)
Formula: C7H9BO2
Molecular Weight: 135.958
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
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%
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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.