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25015-63-8 molecular structure
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4,4,5,5-tetramethyl-1,3,2-dioxaborolane

ChemBase ID: 91429
Molecular Formular: C6H13BO2
Molecular Mass: 127.97722
Monoisotopic Mass: 128.10086006
SMILES and InChIs

SMILES:
B1OC(C)(C)C(O1)(C)C
Canonical SMILES:
CC1(C)OBOC1(C)C
InChI:
InChI=1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
InChIKey:
UCFSYHMCKWNKAH-UHFFFAOYSA-N

Cite this record

CBID:91429 http://www.chembase.cn/molecule-91429.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4,4,5,5-tetramethyl-1,3,2-dioxaborolane
IUPAC Traditional name
4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Synonyms
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane solution
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
Pinacolborane
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
Pinacolborane
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
Pinacolatoborane
Pinacolborane
4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷 溶液
频哪醇硼烷
4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷
频那醇硼烷(PINB)
凤梨醇硼烷
CAS Number
25015-63-8
MDL Number
MFCD00674030
Beilstein Number
7802871
PubChem SID
162078128
24869184
24869353
24884127
PubChem CID
6364989

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.9622  LogD (pH = 7.4) 1.9622 
Log P 1.9622  Molar Refractivity 31.0388 cm3
Polarizability 14.41995 Å3 Polar Surface Area 18.46 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Boiling Point
42-43 °C/50 mmHg(lit.) expand Show data source
42-43°C/50mm expand Show data source
42-43°C/50mm expand Show data source
65-67 °C expand Show data source
Flash Point
-13 °F expand Show data source
-25 °C expand Show data source
41 °F expand Show data source
5 °C expand Show data source
5°C expand Show data source
5°C(41°F) expand Show data source
Density
0.882 expand Show data source
0.882 g/mL at 25 °C(lit.) expand Show data source
0.887 g/mL at 25 °C expand Show data source
Refractive Index
1.3970 expand Show data source
n20/D 1.396(lit.) expand Show data source
Storage Warning
Air Sensitive expand Show data source
Highly Flammable/Moisture Sensitive/Air Sensitive/Keep Cold/Store under Argon expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Irritant Irritant (Xi) expand Show data source
UN Number
3398 expand Show data source
3399 expand Show data source
UN3399 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
4.3 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Risk Statements
11-15 expand Show data source
11-15-19-36/37 expand Show data source
Safety Statements
16-26-43 expand Show data source
16-43 expand Show data source
7/8-9-16-33-43 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H261 expand Show data source
H225-H261-H319-H335 expand Show data source
GHS Precautionary statements
P210-P231 + P232-P261-P305 + P351 + P338-P422 expand Show data source
P210-P231 + P232-P422 expand Show data source
P210-P231+P232-P241-P303+P361+P353-P403+P235-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 3398 4.3/PG 2 expand Show data source
UN 3399 4.3/PG 2 expand Show data source
Supplemental Hazard Statements
May form explosive peroxides. expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
97% expand Show data source
Concentration
1.0 M in THF expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C6H13BO2 expand Show data source

DETAILS

DETAILS

Apollo Scientific Apollo Scientific Sigma Aldrich Sigma Aldrich TRC TRC
Apollo Scientific Ltd - OR7123 external link
Reportedly couples with aryl halides to produce aryl boronates:J.Org.Chem.(1997)62,6458-6459.
Sigma Aldrich - 458945 external link
Packaging
25, 4×25, 100 mL in Sure/Seal™
Sigma Aldrich - 456462 external link
Application
Borylation reagent recently used to prepare 2-borylpyrroles from 2-iodopyrroles via palladium catalysis.1 Also used to borylate aryl bromides and chlorides with Pd(dba)2 and di-tert-butylphosphinophenyl ether.2
Pinacolborane; reagent for selective reduction, hydroboration, and for the preparation of boronates for Suzuki-type couplings.
Packaging
25, 100 mL in Sure/Seal™
Sigma Aldrich - 655856 external link
Packaging
25, 100, 500 g in Sure/Seal™
5 g in glass bottle
Toronto Research Chemicals - P457500 external link
It is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Precursor of boronic esters by hydroboration or coupling reactions. Hydroboration of alkynes, in the presence of Rh or Ni catalysts, yields alkenylboronates: Tetrahedron Lett., 37, 3283 (1996). Hydroboration of alkenes in the presence of Chlorotris(triphenylphosphine)rhodium(I), 10468, affords the alkylboronate: Tetrahedron Lett., 37, 3283 (1996); with phosphine-free catalyst Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466, dehydrogenative borylation predominates to give the alkenylboronate: Tetrahedron Lett., 40, 213 (1999); Bull. Chem. Soc. Jpn., 75, 825 (2002):
  • • Coupling aryl iodides and bromides, catalyzed by [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride, 41225, gives the aryl pinacolboronates: J. Org. Chem., 62, 6458 (1997); 65, 164 (2000). In the presence of triphenylarsine, Pd-catalyzed coupling with alkenyl triflates and iodides affords vinylboronates: Synthesis, 778 (2000). For a brief review of uses of pinacolborane, see: Synlett, 1210 (2000).
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PATENTS

PATENTS

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INTERNET

INTERNET

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