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Structure

Bis(pinacolato)diboron

CAS
73183-34-3
Catalog Number
ACM73183343-1
Category
Other
Molecular Weight
253.94
Molecular Formula
C12H24B2O4

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Specification

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
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.)
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
1
EC Number
615-925-0
Exact Mass
254.18607g/mol
Formal Charge
0
H-Bond Acceptor
4
H-Bond Donor
0
Heavy Atom Count
18
Monoisotopic Mass
254.18607g/mol
Rotatable Bond Count
1
UNII
I906W26P4U

Downstream Synthesis Route 1

  • 180691-65-0
  • 73183-34-3
  • 885693-20-9

Reference: [1]Patent: WO2006/47277,2006,A2 .Location in patent: Page/Page column 97

Downstream Synthesis Route 2

  • 100-66-3
  • 73183-34-3
  • 10365-98-7
  • 5720-07-0

Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250

Downstream Synthesis Route 3

  • 944401-56-3
  • 73183-34-3
  • 944401-57-4
  • 106447-97-6

Reference: [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779

Downstream Synthesis Route 4

  • 207799-10-8
  • 73183-34-3
  • 1095708-32-9

Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637

* For details of the synthesis route, please refer to the original source to ensure accuracy.

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