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| | Bis(hexylene glycolato)diboron Basic information |
| Product Name: | Bis(hexylene glycolato)diboron | | Synonyms: | 4,4,6-TRIMETHYL-2-(4,4,6-TRIMETHYL-1,3,2-DIOXABORINAN-2-YL)-1,3,2-DIOXABORINANE;4,4,4',4',6,6'-HEXAMETHYL-2,2'-BI-1,3,2-DIOXABORINANE;BIS(2-METHYL-2,4-PENTANEDIOLATO)DIBORON;BIS(1,3,3-TRIMETHYL-1,3-PROPANEDIOLATO)DIBORON;BIS(HEXYLENE GLYCOLATO)DIBORON;Bis(1,3,3-trimethyl-1,3-propanediolato)diboron
Bis(2-methyl-2,4-pentanediolato)diboron
4,4,4',4',6,6'-Hexamethyl-2,2'-bi-1,3,2-dioxaborinane;Bis(hexyleneglycolato)diboron,99%;Bis(diisopropyl-L-tartrate glycolato)diboron | | CAS: | 230299-21-5 | | MF: | C12H24B2O4 | | MW: | 253.94 | | EINECS: | | | Product Categories: | B (Classes of Boron Compounds);Diboron Esters;CHIRAL CHEMICALS;Borylation Reagents;Boronic Acids and Derivatives;Organometallic Reagents;DIBORON SERIES;Organoborons | | Mol File: | 230299-21-5.mol |  |
| | 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) |
| 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 |
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ACROS
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| | 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 CC 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 Preparation Products And Raw materials |
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