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2-Tolylboronic acid

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Name

2-Tolylboronic acid

EINECS -0
CAS No. 16419-60-6 Density 1.1 g/cm3
PSA 40.46000 LogP -0.32520
Solubility Slightly soluble in water. Melting Point 162-164 °C(lit.)
Formula C7H9BO2 Boiling Point 283.4 °C at 760 mmHg
Molecular Weight 135.958 Flash Point 125.2 °C
Transport Information N/A Appearance beige crystalline powder
Safety 26-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 16419-60-6 (2-Tolylboronic acid) Hazard Symbols IrritantXi
Synonyms

Boronicacid, (2-methylphenyl)- (9CI);o-Tolueneboronic acid (7CI,8CI);(2-Tolyl)boronic acid;2-Methyl-1-phenylboronic acid;2-Methylbenzeneboronicacid;2-Methylphenylboronic acid;2-Tolueneboronic acid;o-Boronotoluene;o-Methylphenylboronic acid;o-Tolylboronic acid;

Article Data 49

2-Tolylboronic acid Synthetic route

195062-59-0

2-methylphenylboronic acid pinacol ester

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
Stage #1: 2-methylphenylboronic acid pinacol ester With potassium hydrogen difluoride In methanol at 20℃; for 0.25h;
Stage #2: With chloro-trimethyl-silane; water In acetonitrile for 1h;
100%
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h;90%
95-49-8

2-methylchlorobenzene

A

605-39-0

2,2'-dimethyl-1,1'-biphenyl

B

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
With cesium fluoride; Pd(dba)2 In tolueneA n/a
B 97%
95-46-5

2-methylphenyl bromide

16419-60-6

2-Methylphenylboronic acid

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

potassium o-tolyltrifluoroborate

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h;92%
With water; silica gel at 20℃; for 1h; Inert atmosphere;61%
932-31-0

ortho-tolylmagnesium bromide

22092-92-8

diisopropopylaminoborane

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
Stage #1: ortho-tolylmagnesium bromide; diisopropopylaminoborane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere;
88%
121-43-7

Trimethyl borate

95-46-5

2-methylphenyl bromide

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;88%
121-43-7

Trimethyl borate

5419-55-6

Triisopropyl borate

95-46-5

2-methylphenyl bromide

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
Stage #1: Triisopropyl borate; 2-methylphenyl bromide With magnesium; ethylene dibromide In tetrahydrofuran at 40 - 60℃; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran for 6h; Inert atmosphere; Reflux;
85%
68971-87-9

(2-tolyl)tributyltin

16419-60-6

2-Methylphenylboronic acid

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

2-methylphenyl N-methyliminodiacetic acid borate

16419-60-6

2-Methylphenylboronic acid

Conditions
ConditionsYield
Stage #1: 2-methylphenyl N-methyliminodiacetic acid borate With sodium hydroxide In tetrahydrofuran for 0.416667h;
Stage #2: In aq. phosphate buffer; diethyl ether pH=7;
82%
66107-34-4

2-methylphenyl triflate

16419-60-6

2-Methylphenylboronic acid

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

2-Tolylboronic acid Specification

The Boronicacid, B-(2-methylphenyl)-, with the CAS registry number 16419-60-6, is also known as o-Tolylboronic acid. It belongs to the product categories of Blocks; Boronic Acids; Boronic Acid series; Boron, Nitrile, Thio,& TM-Cpds; Substituted Boronic Acids; Aryl; Organoborons; B (Classes of Boron Compounds); Chiral Chemicals; Organic or Inorganic Borate. This chemical's molecular formula is C7H9BO2 and molecular weight is 135.96. What's more, its systematic name is (2-methylphenyl)boronic acid. It is stable at common pressure and temperature, and it should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from strong oxides.

Physical properties of Boronicacid, B-(2-methylphenyl)- are: (1)ACD/LogP: 2.05; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.05; (4)ACD/LogD (pH 7.4): 2.02; (5)ACD/BCF (pH 5.5): 21.24; (6)ACD/BCF (pH 7.4): 20.01; (7)ACD/KOC (pH 5.5): 310.1; (8)ACD/KOC (pH 7.4): 292.16; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.527; (14)Molar Refractivity: 37.91 cm3; (15)Molar Volume: 123.1 cm3; (16)Polarizability: 15.02×10-24cm3; (17)Surface Tension: 40.1 dyne/cm; (18)Density: 1.1 g/cm3; (19)Flash Point: 125.2 °C; (20)Enthalpy of Vaporization: 55.17 kJ/mol; (21)Boiling Point: 283.4 °C at 760 mmHg; (22)Vapour Pressure: 0.00149 mmHg at 25°C.

Uses of Boronicacid, B-(2-methylphenyl)-: it can be used to produce 3-o-tolyl-chromen-4-one by heating. It will need reagent 2 M Na2CO3 and solvents H2O, benzene with the reaction time of 6 hours. This reaction will also need catalyst tetrakis(triphenylphosphine)palladium. The yield is about 94%.

Boronicacid, B-(2-methylphenyl)- can be used to produce 3-o-tolyl-chromen-4-one by heating

When you are using this chemical, please be cautious about it as the following:
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. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: OB(O)c1ccccc1C
(2)Std. InChI: InChI=1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3
(3)Std. InChIKey: NSJVYHOPHZMZPN-UHFFFAOYSA-N

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