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73183-34-3 molecular structure
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4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane

ChemBase ID: 8893
Molecular Formular: C12H24B2O4
Molecular Mass: 253.93856
Monoisotopic Mass: 254.18607005
SMILES and InChIs

SMILES:
B1(B2OC(C(O2)(C)C)(C)C)OC(C(O1)(C)C)(C)C
Canonical SMILES:
CC1(C)OB(OC1(C)C)B1OC(C(O1)(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
InChIKey:
IPWKHHSGDUIRAH-UHFFFAOYSA-N

Cite this record

CBID:8893 http://www.chembase.cn/molecule-8893.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
IUPAC Traditional name
4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
bis(pinacolato)diboron
Synonyms
Bis(pinacolato)diboron
4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane
Bis(pinacolato)diboron
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis(1,3,2-dioxaborolane)
4,4',5,5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane
B2Pin2
Bis(pinacolate)diboron
Bis(pinacolato) diborate
Bis(pinacolato)diborane
Diboron Pinacol Ester
Dipinacoldiboron
Pinacol Diborane
4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
Bis(pinacolato)diboron 99%
4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane
Bis(Pinacolato)diborane
双戊酰二硼
双联频哪醇硼酸酯
双戊酰二硼
CAS Number
73183-34-3
MDL Number
MFCD00799570
Beilstein Number
7703552
PubChem SID
24870893
160972200
PubChem CID
2733548
Chemspider ID
2015334
Wikipedia Title
Bis(pinacolato)diboron

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 4.5764  LogD (pH = 7.4) 4.5764 
Log P 4.5764  Molar Refractivity 60.4776 cm3
Polarizability 28.11265 Å3 Polar Surface Area 36.92 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
133-139°C expand Show data source
137 - 140°C expand Show data source
137-140 °C expand Show data source
137-140 °C(lit.) expand Show data source
137-140°C expand Show data source
139-141°C expand Show data source
ca 135°C expand Show data source
Hydrophobicity(logP)
3.106 expand Show data source
Storage Condition
Refrigerator, Under Inert Atmosphere expand Show data source
Storage Warning
Irritant expand Show data source
IRRITANT, IRRITANT-HARMFUL, KEEP COLD expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-37/39-60 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
95% expand Show data source
96% expand Show data source
98+% expand Show data source
99% expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C12H24B2O4 expand Show data source

DETAILS

DETAILS

Apollo Scientific Apollo Scientific Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Apollo Scientific Ltd - OR5456 external link
Versatile reagent for the preparation of boronic esters:J.Org.Chem.1995, 60,7508-7510.
Sigma Aldrich - 473294 external link
Application
Reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis.1
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.
Packaging
1, 5, 25 g in glass bottle
100 g in poly bottle
500 g in glass bottle
Toronto Research Chemicals - B522770 external link
Bis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Ali, H.A. et al.: Arch. Pharm., 337, 183 (2004)
  • • Izumi, A. et al.: Chem. Lett., 7, 728 (2004)
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PATENTS

PATENTS

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INTERNET

INTERNET

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