655856
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
97%
Synonym(s):
HBpin, Pinacolborane
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About This Item
Empirical Formula (Hill Notation):
C6H13BO2
CAS Number:
Molecular Weight:
127.98
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Quality Level
assay
97%
refractive index
n20/D 1.396 (lit.)
bp
42-43 °C/50 mmHg (lit.)
density
0.882 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
CC1(C)OBOC1(C)C
InChI
1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
InChI key
UCFSYHMCKWNKAH-UHFFFAOYSA-N
Application
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane may be used for:
- Borylation at the benzylic C-H bond of alkylbenzenes in the presence of a palladium catalyst to form pinacol benzyl boronate.
- Hydroboration of alkyl or aryl alkynes and alkenes in the presence of transition metal catalysts.
- Coupling with aryl iodides in the presence of a copper catalyst to form aryl boronates.
- Asymmetric hydroboration of 1,3-enynes to form chiral allenyl boronates.
signalword
Danger
hcodes
Storage Class
4.3 - Hazardous materials which set free flammable gases upon contact with water
wgk
WGK 3
flash_point_f
41.0 °F - closed cup
flash_point_c
5 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Classifications
Flam. Liq. 2 - Water-react. 2
Regulatory Information
危险化学品
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Articles
Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.
Palladium-catalyzed benzylic C?H borylation of alkylbenzenes with bis (pinacolato) diboron or pinacolborane.
Ishiyama T
Chemistry Letters (Jpn), 30(11), 1082-1083 (2001)
Copper-Catalyzed Asymmetric Hydroboration of 1, 3-Enynes with Pinacolborane to Access Chiral Allenylboronates.
Sang HL
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry (2018)
Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature.
Zhu W
Organic Letters, 8(2), 261-263 (2006)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 655856-5G | 04061832733227 |
| 655856-100G | 04061838136138 |
| 655856-25G | 04061832733210 |
| 655856-500G | 04061838254139 |