| Identification | More | [Name]
Bis(neopentyl glycolato)diboron | [CAS]
201733-56-4 | [Synonyms]
5,5,5',5'-TETRAMETHYL-2,2'-BI-1,3,2-DIOXABORINANE
5,5,5',5'-TETRAMETHYL-2,2'-BIS(1,3,2-DIOXABORINANE)
BIS(2,2-DIMETHYL-1,3-PROPANEDIOLATO)DIBORON
BIS(NEOPENTYL GLYCOLATO)DIBORON
BIS(NEOPENTYLGLYCOLATO)DIBORN
Bis(neopentylglycolato)diboron,min.97%
Bis(neopentylglycolato)diboron, min. 97% | [EINECS(EC#)]
639-407-9 | [Molecular Formula]
C10H20B2O4 | [MDL Number]
MFCD02093062 | [Molecular Weight]
225.89 | [MOL File]
201733-56-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light yellow crystal powder | [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. ]
0-6°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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
N | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light yellow crystal powder | [Uses]
Reagent to prepare boronic acid esters. | [Uses]
Bis(neopentyl glycolato)diboron can make borate adducts used for Suzuki coupling.
| [Uses]
suzuki reaction | [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 |
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