4-(N-Boc-amino)phenylboronic acid pinacol ester Chemical Properties

Melting point:

167-170 °C(lit.)

Boiling point:

381.1±25.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

14.00±0.70(Predicted)

color 

White to off-white

InChI

InChI=1S/C17H26BNO4/c1-15(2,3)21-14(20)19-13-10-8-12(9-11-13)18-22-16(4,5)17(6,7)23-18/h8-11H,1-7H3,(H,19,20)

InChIKey

HSJNIOYPTSKQBD-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

CAS DataBase Reference

330793-01-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22-43

Safety Statements 

37/39-26-36-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(N-Boc-amino)phenylboronic acid pinacol ester Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

4-(Boc-amino)benzeneboronic acid pinacol ester is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

Anhydrous dioxane (100 mL) was added to a 250 mL round-bottom flask using pinacol ester of bisboronic acid (10.5 g, 41.5 mmol) and N-tert-butoxycarbonyl-4-bromoaniline (7.75 g, 28.5 mmol). Pd(dppf)Cl2 (0.79 g, 1.1 mmol) and potassium acetate (7.0 g, 71.4 mmol) were subsequently added. The reaction mixture was stirred at 110 °C for 12 h under argon protection. After completion of the reaction, it was cooled to room temperature, filtered and the filtrate was concentrated by rotary evaporator. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 10:1) to afford N-Boc-4-aminophenylboronic acid pinacol ester (3.26 g, 36% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ 9.53 (s, 1H), 7.56 (d, J = 8.5 Hz, 2H), 7.47 (d, J = 8.5 Hz, 2H), 1.48 (s, 9H), 1.29 (s, 12H).

References

[1] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
[2] Patent: US2002/156081, 2002, A1
[3] Patent: US6921763, 2005, B2
[4] Tetrahedron Letters, 2014, vol. 55, # 2, p. 305 - 309
[5] MedChemComm, 2014, vol. 5, # 10, p. 1507 - 1514

4-(N-Boc-amino)phenylboronic acid pinacol ester(330793-01-6)Related Product Information

• Phenylboronic acid
• Butyl acetate
• 3-Aminobenzeneboronic acid
• Sulfanilic acid
• Cyhalofop-butyl
• Aniline
• Sulfanilamide
• Methyl acrylate
• BUTYL OLEATE
• Tris(trimethylsilyl)phosphate
• Bis(pinacolato)diboron
• Dibutyl phthalate
• PHENYL VALERATE
• Diethylene glycol monobutyl ether
• 4-Aminobenzoic acid
• Dimethyl succinate
• 4-Aminophenylacetic acid
• Buprofezin