Bis(hexylene glycolato)diboron Chemical Properties

Melting point:

98-102 °C (lit.)

Boiling point:

242.8±7.0 °C(Predicted)

Density 

0.97±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

white

Water Solubility 

Insoluble

InChI

1S/C12H24B2O4/c1-9-7-11(3,4)17-13(15-9)14-16-10(2)8-12(5,6)18-14/h9-10H,7-8H2,1-6H3

InChIKey

UEBSWKNVDRJVHN-UHFFFAOYSA-N

SMILES

CC1CC(C)(C)OB(O1)B2OC(C)CC(C)(C)O2

CAS DataBase Reference

230299-21-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29349990

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:ACROS

Bis(hexylene glycolato)diboron Usage And Synthesis

Chemical Properties

White crystalline powde

Uses

suzuki reaction

Uses

Bis(hexylene glycolato)diboron can be used as a reagent:

• To prepare aryl boronate esters via metal-catalyzed direct C-H borylation of aryl compounds.
• In the chemoselective synthesis of C?C coupling products via nickel catalyzed coupling of primary and secondary alkyl halides.
• In the nickel-catalyzed regioselective arylboration of terminal nonactivated alkenes to yield alkyl boranes.

Synthesis

General procedure for the synthesis of bis(2-methyl-2,4-pentanediol) borate from 2-methyl-2,4-pentanediol: 2-methyl-2,4-pentanediol (FW: 118.18; 22.0 g, 101.6 mmol) was dissolved in toluene (40 mL), and tetrakis(dimethylamino)diboron (FW: 197.926; 9.9 g, 50 mmol ). The reaction mixture was stirred at room temperature. the temperature was raised to 100 °C within 10 min and the release of dimethylamine started after about 5 min. The reaction temperature was maintained at 100 °C for 60 min, during which time the release of dimethylamine was complete at 30 min. At the end of the reaction, toluene was removed by distillation under reduced pressure to give a solid product (99.6% GC purity). The solid product was recrystallized from a solvent mixture of toluene and petroleum ether (boiling point 80°C-100°C) (1:9, v/v) to give a colorless solid bis(2-methyl-2,4-pentanediol) diboronate (MF: C12H24B2O4; FW: 253.94): the first batch of product was 8.83 g, the second batch of product was 3.69 g, with a combined yield of 12.52 g and a yield of 98.6%; GC purity was 99.6%. Melting point 99-101.6 °C. 1H NMR (200 MHz, CDCl3) δ: 1.21 (d, J = 7 Hz, 6H), 1.28 (s, 12H), 1.47 (dd, J = 12, 14 Hz, 2H), 1.70 (dd, J = 14, 3 Hz, 2H), 4.14 (dm, 2H) ppm. 13C NMR (50 MHz, CDCl3) δ: 23.1, 28.3, 31.2, 46.2, 64.1, 70.3 ppm.

References

[1] Patent: WO2004/76467, 2004, A1. Location in patent: Page 15
[2] Patent: CN105524099, 2016, A

Bis(hexylene glycolato)diboron(230299-21-5)Related Product Information

• Ethylene glycol monoethyl ether acetate
• 2-Butoxyethyl acetate
• 2-Methyl-2,4-pentanediol
• 2,2-Dimethyl-1,3-propanediol
• 2-METHYL-1,3-PROPANEDIOL
• Zolpidem tartrate
• Poly(tetrahydrofuran)
• Tylosin tartrate
• 1-Methoxy-2-propyl acetate
• 1,2-Pentanediol
• Bis-Mal-Lysine-PEG4-TFP ester
• Bis(2,4-dimethylpentane-2,4-glycolato)diboron
• Boron
• 2,4-PENTANEDIOL
• Bis(diisopropyl-D-tartrate glycolato)diboron
• Bis(diisopropyl-L-tartrate glycolato)diboron
• Boric acid
• TETRAHYDROXYDIBORON