| Identification | More | [Name]
2-Tolylboronic acid | [CAS]
16419-60-6 | [Synonyms]
2-METHYLBENZENEBORONIC ACID
2-METHYLPHENYLBORONIC ACID
2-TOLYLBORONIC ACID
AKOS BRN-0017
O-METHYLPHENYLBORONIC ACID
O-TOLYLBORONIC ACID
RARECHEM AH PB 0228
TOLUENE-2-BORONIC ACID
2-TOLYLBORONIC ACID(2-Methylbenzeneboronic acid)
2-Methylpenylboronic Acid
O-TOLYBORONIC ACID
2-Methylphenylboronic
o-Tolylboronicacid,min.97%
2-METHYLPHENYLBORONIC ACID, O-TOLYBORONIC ACID
2-METHYLSUFINYLPHENYLBORONIC ACID
2-Methylphenylboronic Acid (contains varying amounts of Anhydride)
2-Methylphenylboronic acid (o-Tolylboronic acid)
2-Tolueneboronic acid
o-Boronotoluene
2-Tolylboronic acid ,98% | [EINECS(EC#)]
605-351-9 | [Molecular Formula]
C7H9BO2 | [MDL Number]
MFCD00093526 | [Molecular Weight]
135.96 | [MOL File]
16419-60-6.mol |
| Chemical Properties | Back Directory | [Appearance]
beige crystalline powder | [Melting point ]
162-164 °C(lit.)
| [Boiling point ]
283.4±33.0 °C(Predicted) | [density ]
1.10±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
8.61±0.58(Predicted) | [color ]
Beige | [Water Solubility ]
Slightly soluble in water. | [Detection Methods]
HPLC,NMR | [BRN ]
2935796 | [InChI]
InChI=1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3 | [InChIKey]
NSJVYHOPHZMZPN-UHFFFAOYSA-N | [SMILES]
B(C1=CC=CC=C1C)(O)O | [CAS DataBase Reference]
16419-60-6(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Description]
2-Methylphenylboronic acid is an important organic boronic acid compound, which is widely used in Suzuki cross-coupling reaction and has important application value in the fields of organic synthesis and medicine and chemical industry. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
ED7777777 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Physical properties]
beige crystalline powder | [Uses]
2-Methylbenzeneboronic acid is a reagent used for Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water, Ruthenium catalyzed direct arylation reactions, Ligand-free copper-catalyzed coupling reactions, Rhodium-catalyzed asymmetric 1,4-addition reactions. Reagent used in Preparation of chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction, Human farnesyl pyrophosphate synthase inhibitors as antitumor agents for multiple myeloma cells | [Uses]
suzuki reaction | [Synthesis]
Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol %), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol %) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3×10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH ≤1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3×10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid named 2-Tolylboronic acid. |
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