| Identification | More | [Name]
3-Tolylboronic acid | [CAS]
17933-03-8 | [Synonyms]
3-METHYLBENZENEBORONIC ACID
3-METHYLPHENYLBORONIC ACID
3-TOLYBORONIC ACID
3-TOLYLBORONIC ACID
AKOS BRN-0018
M-METHYLPHENYLBORONIC ACID
M-TOLYLBORONIC ACID
RARECHEM AH PB 0229
TOLUENE-3-BORONIC ACID
3-Methylpenylboronic Acid
3-Methylphenylboric acid
-Tolylboronic acid
m-Tolylboronicacid,min.97%
M-TOLYBORONICACID
3-METHYLPHENYLBORONIC ACID, 3-TOLYLBORONIC ACID, M-TOLYLBORONIC ACID
3-TOLYLBORONIC ACID 98%
3-Methylphenylboronic Acid (contains varying amounts of Anhydride)
Boronic acid, (3-methylphenyl)-
m-Methylbenzeneboronic acid
m-Methylborophenylic acid | [EINECS(EC#)]
605-855-9 | [Molecular Formula]
C7H9BO2 | [MDL Number]
MFCD00040198 | [Molecular Weight]
135.96 | [MOL File]
17933-03-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
160-162 °C(lit.)
| [Boiling point ]
290.4±33.0 °C(Predicted) | [density ]
1.10±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [Water Solubility ]
Slightly soluble in water | [form ]
Powder and Chunks | [pka]
8.63±0.10(Predicted) | [color ]
Beige | [Detection Methods]
HPLC,NMR | [BRN ]
2935968 | [InChI]
InChI=1S/C7H9BO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5,9-10H,1H3 | [InChIKey]
BJQCPCFFYBKRLM-UHFFFAOYSA-N | [SMILES]
B(C1=CC=CC(C)=C1)(O)O | [CAS DataBase Reference]
17933-03-8(CAS DataBase Reference) |
| 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 ]
ED7788888 | [Hazard Note ]
Irritant | [TSCA ]
No | [HazardClass ]
IRRITANT | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
Suzuki coupling reactions | [Uses]
suzuki reaction | [Application]
3-Tolylboronic acid is an impurity of Eltrombopag, Eltrombopag is used to treat low blood platelet counts in adults with chronic immune (idiopathic) thrombocytopenia (ITP), when certain other medicines, or surgery to remove the spleen, have not worked well enough. | [Synthesis]
The general procedure for the synthesis of 3-methylphenylboronic acid from trimethyl borate and 3-bromomethylbenzene is as follows: 0.10 mol (0.1 eq.) of 3-bromomethylbenzene, 1.1 mol (1.1 eq.) of magnesium scraps, a few iodine crystals, and 800 mL of tetrahydrofuran (THF) were added to a reaction flask, stirred and heated to reflux. When the Grignard reaction was initiated, 0.90 mol (0.9 eq.) of 3-bromomethylbenzene was slowly added dropwise under reflux conditions, and the reaction was continued at reflux after completion of the dropwise addition. After completion of the reaction, the reaction system was cooled down to -50.0 °C. Subsequently, 2.2 mol (2.2 eq.) of trimethyl borate was slowly added dropwise and the reaction was kept at a low temperature until the feedstock was completely consumed. Upon completion of the reaction, the temperature was gradually increased and water was added to quench the reaction. Then, hydrochloric acid was added dropwise to adjust the pH to 1-2 and the reaction was continued with stirring. After completion of the reaction, the solvent was removed by rotary evaporation and the product was dried by filtration to give 0.90 mol of 3-methylphenylboronic acid as a white solid with 0.03% water content, 98.86% purity and 90.0% yield. | [References]
[1] Patent: CN106946924, 2017, A. Location in patent: Paragraph 0009; 0020; 0023; 0026
[2] Patent: US5183653, 1993, A |
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