3-Amino-2-methylphenylboronic acid, pinacol ester Chemical Properties

Boiling point:

365.3±35.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

2-8°C, protect from light

pka

4.44±0.10(Predicted)

form 

solid

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C13H20BNO2/c1-9-10(7-6-8-11(9)15)14-16-12(2,3)13(4,5)17-14/h6-8H,15H2,1-5H3

InChIKey

JMKMGPGFYMANCA-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2931900090

3-Amino-2-methylphenylboronic acid, pinacol ester Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline from 4,4,5,5-tetramethyl-2-(2-methyl-3-nitrophenyl)-1,3,2-dioxaborolan-2-yl)aniline: in a 500 mL round-bottomed flask 4,4,5,5-tetramethyl-2-(2-methyl-3-nitrophenyl) -1,3,2-dioxaborolane(6) (8.44 g, 32.1 mmol) and methanol (150 mL) in a 500 mL round-bottom flask equipped with a magnetic stirrer. After the reaction system was evacuated twice and replaced with argon, 10% palladium carbon catalyst (50% wet weight, 425 mg dry weight) was added. The reaction system was again evacuated and replaced with hydrogen three times. The reaction was stirred at room temperature for 13 hours under hydrogen balloon pressure. Upon completion of the reaction, the system was evacuated twice and replaced with argon, filtered through a diatomaceous earth pad (521) and the filtrate was concentrated under vacuum. The resulting residue was dried under high vacuum for 24 h to afford 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (7) in quantitative yield (8.16 g) as a white solid with a melting point of 110-112 °C; mass spectrum (ESI+) m/z 234 (M+H).

References

[1] Patent: US2009/82330, 2009, A1. Location in patent: Page/Page column 24
[2] Patent: WO2008/33858, 2008, A2. Location in patent: Page/Page column 130; 137
[3] Patent: WO2009/137596, 2009, A1. Location in patent: Page/Page column 69-70
[4] Patent: WO2008/33858, 2008, A2. Location in patent: Page/Page column 130; 137
[5] Patent: WO2009/77334, 2009, A1. Location in patent: Page/Page column 87

3-Amino-2-methylphenylboronic acid, pinacol ester(882678-96-8)Related Product Information

• 4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL
• 4-AMINOMETHYLPHENYLBORONIC ACID HYDROCHLORIDE
• 4-AMINO-2-METHYLPHENYLBORONIC ACID, PINACOL ESTER
• 4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL
• 3-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL
• 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine
• 5-AMINO-2-METHYLPHENYLBORONIC ACID, PINACOL ESTER
• 3-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL
• 2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER
• 2-METHYL-3-NITROPHENYLBORONIC ACID, PINACOL ESTER
• 3-Amino-2-methylphenylboronic acid, pinacol ester