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655856

Sigma-Aldrich

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:
25015-63-8
Molecular Weight:
127.98
MDL number:
MFCD00674030
UNSPSC Code:
12352103
PubChem Substance ID:
24884127
NACRES:
NA.22

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

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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.

Related product

Product No.
Description
Pricing

907847

HB(trip)2, ≥95%

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225,H261

Hazard Classifications

Flam. Liq. 2 - Water-react 2

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

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

Certificates of Analysis (COA)

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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)
A study of hydroboration of alkenes and alkynes with pinacolborane catalyzed by transition metals.
Pereira S
Tetrahedron Letters, 37(19), 3283-3286 (1996)
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)
Palladium-catalyzed benzylic C?H borylation of alkylbenzenes with bis (pinacolato) diboron or pinacolborane.
Ishiyama T
Chemistry Letters (Jpn), 30(11), 1082-1083 (2001)

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