CAS 73183-34-3 Bis(pinacolato)diboron - Materials / Alfa Chemistry

NAVIGATION

Bis(pinacolato)diboron

PRICE INQUIRY

Catalog Number

ACM73183343-1

CAS Number

73183-34-3

Product Name

Bis(pinacolato)diboron

Structure

Category

Salt; Organic Light-Emitting Diode (OLED) Materials; Other Electronic Materials

Synonyms

4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane

IUPAC Name

4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane

Molecular Weight

253.94

Molecular Formula

C12H24B2O4

Canonical SMILES

B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C

InChI

InChI=1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3

InChI Key

IPWKHHSGDUIRAH-UHFFFAOYSA-N

Boiling Point

222.6±7.0 °C

Melting Point

137-140 °C (lit.)

Purity

99.5%+

Density

0.98 g/ml

Appearance

White powder or platelets

Application

Bis(pinacolato)diboron serves as a versatile reagent in organic synthesis, primarily recognized for its role in the formation of pinacol boronic esters. This white crystalline powder is widely employed as a coupling and condensation agent in the preparation of poly(arylene)s and the synthesis of aryl, alkenyl, allyl, and alkylboronic esters. Additionally, it functions in the borylation of α,β-unsaturated ketones and is pivotal in the diborylation of alkynes. Bis(pinacolato)diboron also finds application in creating precursors for conducting polymers and synthesizing in vivo fluorescent probes. Furthermore, it exhibits potential as an inhibitor of matrix metallo-proteinase, specifically gelatinase A (EC 3.4.24.24), highlighting its diverse utility in both industrial and biomedical domains.

Complexity

286

Covalently-Bonded Unit Count

EC Number

615-925-0

Exact Mass

254.18607g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

B(P)DB;bis(pinacolato)diboron

Monoisotopic Mass