| Identification | More | [Name]
3-Methoxycarbonylphenylboronic acid | [CAS]
99769-19-4 | [Synonyms]
3-(METHOXYCARBONYL)BENZENEBORONIC ACID
3-METHOXYCARBONYLPHENYLBORONIC ACID
AKOS BRN-0125
METHYL 3-BORONOBENZOATE
M-(METHOXYCARBONYL)PHENYLBORONIC ACID
3-METHOXYCARBONYLPHENYLBARONIC ACID
3-(Methoxycarbonyl)phenylboronic Acid (contains varying amounts of Anhydride) | [Molecular Formula]
C8H9BO4 | [MDL Number]
MFCD02093046 | [Molecular Weight]
179.97 | [MOL File]
99769-19-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light yellow crystal powde | [Melting point ]
205-208 °C(lit.) | [Boiling point ]
359.9±44.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [form ]
Powder | [pka]
7.74±0.10(Predicted) | [color ]
White to off-white | [Water Solubility ]
Reacts with water. | [InChI]
InChI=1S/C8H9BO4/c1-13-8(10)6-3-2-4-7(5-6)9(11)12/h2-5,11-12H,1H3 | [InChIKey]
ALTLCJHSJMGSLT-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=CC(B(O)O)=C1 | [CAS DataBase Reference]
99769-19-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light yellow crystal powde | [Uses]
3-Methoxycarbonylphenylboronic acid can be used in the preparation of substituted pyrazolylpyrimidinamine derivative for use as protein kinase inhibitors and suzuki reaction.
| [Uses]
Reagent used for tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, one-pot ipso-nitration of arylboronic acids, copper-catalyzed nitration, cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling. Reagent used in Preparation of biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6, chromenones and their bradykinin B1 antagonistic active, Pt nanoparticles at Photoactive metal-organic frameworks resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injecti, salicylate-based thienylbenzoic acids as E. coli methionine aminopeptidase inhibitor. | [Uses]
suzuki reaction | [Synthesis]
In a 20 L reactor, 8.0 Kg of anhydrous methanol and 1.66 Kg (10 mol) of 3-carboxyphenylboronic acid were added and stirring was initiated. The reaction mixture was heated to 55°C and the temperature was maintained in the range of 55-65°C. 1.78Kg (15mol) of thionyl chloride was slowly added dropwise to the reaction kettle. After completion of the reaction, reflux was continued for 2-3 hours. The completion of the reaction was confirmed by TLC (unfolding agent: n-heptane/ethyl acetate = 2:1). The reaction solution was then cooled and subjected to reduced pressure distillation to remove the solvent. N-heptane was added and the mixture was cooled to -10 to 0°C and filtered with continuous stirring for 1 hour. The solid product was collected and dried at 80 °C until the absence of impurities was confirmed by HNMR (DMSO-d6, δ=3.16 ppm). The dried solid was stirred at room temperature and water was added, filtered and dried at room temperature to give 1.75 Kg of the final white solid product m-Carbomethoxyphenylboronic acid in 97.1% yield. | [References]
[1] Patent: CN106188117, 2016, A. Location in patent: Paragraph 0015 |
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