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655856

Sigma-Aldrich

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

97%

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Synonym(s):
HBpin, Pinacolborane
Empirical Formula (Hill Notation):
C6H13BO2
CAS Number:
Molecular Weight:
127.98
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

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1 of 4

This Item
458945673943417149
refractive index

n20/D 1.396 (lit.)

refractive index

-

refractive index

n20/D 1.4096

refractive index

n20/D 1.409 (lit.)

bp

42-43 °C/50 mmHg (lit.)

bp

65-67 °C

bp

-

bp

73 °C/15 mmHg (lit.)

density

0.882 g/mL at 25 °C (lit.)

density

0.887 g/mL at 25 °C

density

0.9642 g/mL at 25 °C

density

0.912 g/mL at 25 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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.

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Pictograms

Flame

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 2 - Water-react 2

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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)
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)
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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