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CAS NO:25015-63-8
EC NO:607-485-3
Pinacolborane is the borane with the formula (CH3)4C2O2BH.
Pinacolborane features a boron hydride functional group incorporated in a five-membered C2O2B ring. Like related boron alkoxides, pinacolborane is monomeric.
Pinacolborane is a colorless liquid.
Pinacolborane features a reactive B-H functional group.
Properties
Chemical formula C6H13BO2
Molar mass 127.98 g·mol−1
Appearance colorless liquid
Density 0.882 g/cm3
Boiling point 42–43 °C (108–109 °F; 315–316 K) 50 mmHg
Use in organic synthesis
In the presence of catalysts, pinacolborane hydroborates alkenes and, less rapidly, alkynes.
Pinacolborane also effects catalyst-free hydroboration of aldehydes, ketones, and carboxylic acids.
Pinacolborane is used in borylation, a form of C-H activation.
Dehydrogenation of pinacolborane affords dipinacolatodiborane (B2pin2):
2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2
Application
Pinacolborane may be used for:
Borylation at the benzylic C-H bond of alkylbenzenes in the presence of a palladium catalyst to form pinacol benzyl boronate.
Hydroboration of alkyl or aryl alkynes and alkenes in the presence of transition metal catalysts.
Coupling with aryl iodides in the presence of a copper catalyst to form aryl boronates.
Asymmetric hydroboration of 1,3-enynes to form chiral allenyl boronates.
Pinacolborane is used as a precursor of boronic esters by hydroboration or coupling reactions.
Pinacolborane acts as a monofunctional hydroborating agent.
Pinacolborane is used in the synthesis of unsymmetrical biaryls through aromatic C-H borylation-cross-coupling sequence.
Pinacolborane is involved in the preparation of 4,4,5,5-tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane by reacting with 2-iodo-thiophene. Further, it is used to prepare vinylboronates by palladium-catalyzed coupling with alkenyl triflates and iodides.
Chemical Properties
Clear colorless liquid
Uses
Pinacolborane is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.
Pinacolborane is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.
Application:
Used for hydroboration of alkenes and alkynes.
Used for catalytical borylation of aromatic compounds with formating of arylboronates which are further used in Suzuki cross-coupling reactions
Pinacolborane is a hydroboration reagent that offers several advantages over catecholborane; milder reaction conditions, higher functional group tolerance, and better regio- and stereo-selectivity. Compound can be used for the direct introduction of boronates by its reaction with alkenes, alkynes, or aryl halides. The resulting pinacolboronates, which display excellent aqueous and chromatographic stability, can be further used in C-C bond forming reactions, such as Suzuki-Miyaura couplings.
Description
Pinacolborane is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence,used to produce other chemicals.
Chemical Properties
Appearance Clear colorless liquid
CAS Number 25015-63-8
Density 0.882 g/ml
InChI 1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
InChIKey UCFSYHMCKWNKAH-UHFFFAOYSA-N
Molar Mass 127.98 g/mol
Molecular Formula C6H13BO2
About this substance
Helpful information
Pinacolborane is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
This substance is used at industrial sites.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using this substance. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Uses at industrial sites
Pinacolborane is used in the following products: pharmaceuticals.
Pinacolborane is used in the following areas: health services.
Release to the environment of Pinacolborane can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
IUPAC names
1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
4,4,5,5-tetramethyl-1,3,2λ²-dioxaborolane
Pinacolboran mit 1% Triethylamin
SYNONYMS:
1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl- [ACD/Index Name]
25015-63-8 [RN]
4,4,5,5-Tetramethyl-1,3,2-dioxaborolan [German] [ACD/IUPAC Name]
4,4,5,5-tetramethyl-1,3,2-dioxa-borolane
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane [ACD/IUPAC Name]
4,4,5,5-Tétraméthyl-1,3,2-dioxaborolane [French] [ACD/IUPAC Name]
HBpin
MFCD00674030 [MDL number]
Pinacolborane
1186310-96-2 [RN]
1186310-97-3 [RN]
'25015-63-8
4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
4,4,5,5-Tetramethyl[1,3,2]dioxaborolane
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-1,3,2λ2-dioxaborolane
4,4,5,5-tetramethyl-1,3,2λ2-dioxaborolane
4£¬4£¬5£¬5-Tetramethyl-1£¬3£¬2-dioxaborolane
56885-17-7 [RN]
boronic acid pinacol ester
PI-46098
Pinacol Borane
Pinacolatoborane
pinacolborane 97%, spcseal
pinacolborane(rs20007353)
pinacolborane, 97%, stabilized
pinacolborane,97%
