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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

Signal Word

Danger

Hazard Statements

H225,H261

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

655856-BULK:
655856-5G:
655856-500G:
655856-25G:
655856-100G:
655856-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium-catalyzed benzylic C?H borylation of alkylbenzenes with bis (pinacolato) diboron or pinacolborane.
Ishiyama T
Chemistry Letters (Jpn), 30(11), 1082-1083 (2001)
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)

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