Bis(neopentyl glycolato)diboron Chemical Properties

Melting point:

180.5-184.5 °C(lit.)

Boiling point:

214.3±7.0 °C(Predicted)

Density 

0.99±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Liquid

color 

Clear colorless

Sensitive 

moisture sensitive

BRN 

8839038

InChI

InChI=1S/C10H20B2O4/c1-9(2)5-13-11(14-6-9)12-15-7-10(3,4)8-16-12/h5-8H2,1-4H3

InChIKey

MDNDJMCSXOXBFZ-UHFFFAOYSA-N

SMILES

O1CC(C)(C)COB1B1OCC(C)(C)CO1

CAS DataBase Reference

201733-56-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

TSCA 

N

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

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

Bis(neopentyl glycolato)diboron Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

suzuki reaction

Uses

Reagent to prepare boronic acid esters.

Uses

Bis(neopentyl glycolato)diboron can make borate adducts used for Suzuki coupling.

Synthesis

The general procedure for the synthesis of neopentyl glycol ester of biphenylboronic acid from neopentyl glycol was as follows: tetrakis(dimethylamino)diboron (9.89 g, 52.65 mmol) was slowly added to a solution of 2,2-dimethyl-1,3-propanediol (neopentyl glycol, 10.42 g, 100 mmol) in toluene (40 mL) at room temperature. The reaction mixture was then heated to 105°C, at which point dimethylamine gas began to be released. After maintaining this temperature and continuing the reaction for 60 min, the toluene solvent was removed by distillation under reduced pressure to give 11.39 g of white solid product in 95.8% yield. The crude product was purified by recrystallization from toluene to give 6.48 g of bis(neopentylglycolic acid)boron (molecular formula: C10H20B2O4; molecular weight: 225.89) in 54.5% yield. The melting point of the product was 182.5-184.5 °C. NMR hydrogen spectrum (CDCl3, 200 MHz) data: δ 0.94 (s, 12H), 3.58 (s, 6H) ppm; NMR carbon spectrum (CDCl3, 50 MHz) data: δ 22.3 (4×CH3), 31.9 (2×C), 71.7 (4×CH2) ppm. The mother liquor was retained for subsequent recrystallization.

References

[1] Patent: WO2004/76467, 2004, A1. Location in patent: Page 15

Bis(neopentyl glycolato)diboron(201733-56-4)Related Product Information

• Biphenyl dimethyl dicarboxylate
• Bis(pinacolato)diboron
• 2,2-Bis(bromomethyl)propane-1,3-diol
• 2,2-Dimethyl-1,3-propanediol
• Zinc borate
• Boric acid esters
• TETRAHYDROXYDIBORON
• Bis(neopentyl glycolato)diboron