Bis(pinacolato)diboron

Inquiry

Molecular Formula:

C12H24O4B2

Molecular Weight:

253.94

CAS Number:

73183-34-3

Catalog Number:

73183-34-3

Product Information

Molecular Formula:

C12H24O4B2

Molecular Weight:

253.94

Description

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.

Synonyms

4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-(4,4,5,5-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 °C at 760 mmHg

Melting Point

137-140 °C (lit.)

Flash Point

Not applicable

Purity

99 %

Density

0.97 g/cm³

Appearance

Colorless solid

Application

Used as a boron source in organic syntheses.

LogP

2.24920

Safety Information

Precautionary Statement

P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501

Signal Word

Danger

Computed Properties

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Exact Mass

254.1860696 g/mol

Monoisotopic Mass

254.1860696 g/mol

Topological Polar Surface Area

36.9Å²

Heavy Atom Count

Formal Charge

Complexity

286

Isotope Atom Count

Defined Atom Stereocenter Count

Undefined Atom Stereocenter Count

Defined Bond Stereocenter Count

Undefined Bond Stereocenter Count

Covalently-Bonded Unit Count

Compound Is Canonicalized

Yes

Patents

Publication Number	Title	Priority Date
CN-114181048-A	Preparation method of high-yield 4-fluorodiphenol	2021-12-20
CN-114181220-A	Solenoid-shaped magnetic carbon nano material and preparation method thereof	2021-12-17
JP-2022031355-A	Pest control method	2021-12-15
CN-113929712-A	Simple preparation method of benzyl borate compound	2021-11-17
CN-114057616-A	Method for synthesizing N-substituted benzene sulfonamide compound	2021-11-12
CN-114032129-A	Surface modification method for transition metal sulfide and application thereof	2021-11-03
CN-113801154-A	Synthesis method of 9H-carbazole-2-boronic acid pinacol ester with C2-position of carbazole directly boronated by C-H	2021-10-20
CN-113861228-A	Alkyl borane derivative and synthetic method thereof	2021-10-13
CN-113896732-A	Preparation method and application of anti-cancer drug carbamatinib	2021-10-13
CN-114057775-A	Super-base material, preparation method thereof and organic light-emitting diode	2021-10-13

Literatures

PMID	Publication Date	Title	Journal
19505078	2009-07-08	Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration	Journal of the American Chemical Society
18007422	2004-02-27	Biaryl product formation from cross-coupling in palladium-catalyzed borylation of a Boc protected aminobromoquinoline compound	Molecules (Basel, Switzerland)
12945899	2003-06-21	Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A	Organic & biomolecular chemistry
12095344	2002-07-10	Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence	Journal of the American Chemical Society
5697	1976-06-01	Cell-mediated immunity: mechanisms, significance, and evaluation	Pediatric annals
3779	1976-02-01	Detrimental effect of in vitro salivary contamination of acid-etched enamel	Proceedings of the Finnish Dental Society. Suomen Hammaslaakariseuran toimituksia
5235	1976-01-01	Effect of acetylcholine and high external potassium ions on 45Ca movements in molluscan smooth muscle	Comparative biochemistry and physiology. C: Comparative pharmacology
5022	1975-12-01	[The utilization of EB 51 in parenteral feeding. Clinical, biological and anatomopathological control. Statistical study on 30 patients]	Annales de l'anesthesiologie francaise

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