Identification | More | [Name]
2,3-Dimethoxyphenylboronic acid | [CAS]
40972-86-9 | [Synonyms]
2,3-DIMETHOXYBENZENEBORONIC ACID 2,3-DIMETHOXYPHENYLBORONIC ACID AKOS BRN-0202 2,3-dimethoxyphenylboronci acid 2,3-Dimethoxyphenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
670-283-9 | [Molecular Formula]
C8H11BO4 | [MDL Number]
MFCD02683112 | [Molecular Weight]
181.98 | [MOL File]
40972-86-9.mol |
Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
67-71 °C (lit.) | [Boiling point ]
347.9±52.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [form ]
powder to crystal | [pka]
8.12±0.58(Predicted) | [color ]
White to Almost white | [BRN ]
3051295 | [InChI]
InChI=1S/C8H11BO4/c1-12-7-5-3-4-6(9(10)11)8(7)13-2/h3-5,10-11H,1-2H3 | [InChIKey]
VREWSCMOGIXMDQ-UHFFFAOYSA-N | [SMILES]
B(C1=CC=CC(OC)=C1OC)(O)O | [CAS DataBase Reference]
40972-86-9(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 . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT | [HS Code ]
29319090 |
Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
suzuki reaction | [General Description]
Contains varying amounts of anhydride | [Synthesis]
To a solution of N,N,N',N'-tetramethylethylenediamine (6.1 mL, 40.5 mmol) in diethyl ether (100 mL) was added n-butyllithium (26 mL, 1.6 M in hexane, 41.6 mmol) dropwise at 0° C. After 30 min the reaction mixture was cooled to -78° C., 1,2-dimethoxybenzene (5.0 g, 36.4 mmol) and stirred for 3 h at this temperature. Subsequently, trimethyl borate (9.7 mL, 86.4 mmol) was added, the cold bath was removed and the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the mixture was cooled to 0 °C, 150 mL of aqueous 2 M hydrochloric acid was added and stirred for 3 hours. The mixture was extracted with ethyl acetate (3 x 20 mL), the organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuum to afford 2,3-dimethoxyphenylboronic acid (1 g, 37% yield) as white crystals.
6-Bromo-2,2,4-trimethyl-1,2-dihydroquinoline (256 mg, 1.02 mmol) and 2,3-dimethoxyphenylboronic acid (370 mg, 2.03 mmol) were dissolved in DMSO (2 mL), and 2 M aqueous K3PO4 (1 mL) was added, followed by PdCl2 (dppf) (50 mg). The mixture was transferred to a microwave reaction tube and microwave irradiated at 120 °C for 15 min. After completion of the reaction, it was cooled to room temperature and the crude product was purified by column chromatography to afford 6-(2,3-dimethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (190 mg, 61% yield) as a white solid.
The product was brominated with N-bromosuccinimide, followed by a coupling reaction with 2-phenylethanethiol as described in Example 7 to give 45 mg of 2,3-dimethoxyphenylboronic acid as an oil. | [References]
[1] Chemical Communications, 1999, # 22, p. 2259 - 2260 [2] Patent: WO2004/18429, 2004, A2. Location in patent: Page 85 [3] Bulletin de la Societe Chimique de France, 1973, p. 767 - 769 |
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