Bis(pinacolato)diboron - ≥99% , CAS No.73183-34-3

CAS: 73183-34-3 Cat. No.: B396365 Molecular Weight: 253.94 EC Number: 615-925-0

GRADE & PURITY ≥99%

Synonyms

4,4,5,5,4',4',5',5'-octamethyl-[2,2']bi[1,3,2]dioxaborolanyl | bis (pinacolato) diborane | Dipinacoldiboron | dipinacol-diboron | MFCD00799570 | UNII-I906W26P4U | B2Pin2 | Bis(2,2,3,3-tetramethyl-2,3-butanedionato)diboron | bis(pinacolate)diborane(4) | DT

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Bis(pinacolato)diboron or (B2pin2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.
Application
Reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis.
Substrate used in a new palladium-catalyzed cyclization of 1,6-enynes leading to homoallylic alkylboronates.
Used to construct a tetramethylpyrrolidine nitroxide scaffold for the synthesis of paramagnetic heterocycles by Suzuki coupling.

Specifications

Synonyms

4, 4, 5, 5, 4', 4', 5', 5'-octamethyl-[2, 2']bi[1, 3, 2]dioxaborolanyl | bis (pinacolato) diborane | Dipinacoldiboron | dipinacol-diboron | MFCD00799570 | UNII-I906W26P4U | B2Pin2 | Bis(2, 2, 3, 3-tetramethyl-2, 3-butanedionato)diboron | bis(pinacolate)diborane(4) | DT

Specifications & Purity

≥99%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C
• IUPAC Name: 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
• InChIKey: IPWKHHSGDUIRAH-UHFFFAOYSA-N
• 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
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C
• WGK Germany: 3
• Molecular Weight: 253.94
• Reaxy-Rn: 7703552
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7703552&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Dioxaborolanes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Dioxaborolanes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Dioxaborolanes
• Alternative Parents: Oxacyclic compounds Organic metalloid salts Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 1,3,2-dioxaborolane - Oxacycle - Organic metalloid salt - Organic oxygen compound - Hydrocarbon derivative - Organic salt - Organooxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dioxaborolanes. These are compounds containing a five-member saturated aliphatic heterocycle made up of two oxygen atoms, a boron atom, and three carbon atoms.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in tetrahydrofuran, dichloromethane, toluene, hexane and heptane. Insoluble in water.
• Sensitivity: Moisture & heat sensitive
• Melt Point(°C): 135-140°C
• Molecular Weight: 253.900 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.186 Da
• Monoisotopic Mass: 254.186 Da
• Topological Polar Surface Area: 36.900 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 286.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

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