Bis(pinacolato)diboron
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
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
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
254.1860696 g/mol
Monoisotopic Mass
254.1860696 g/mol
Topological Polar Surface Area
36.9Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
286
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
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 |
