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900989 Sigma-Aldrich

1,3,5-Phenyltriboronic acid, tris(pinacol) ester

≥97%

Synonym: 1,3,5-Tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

  • CAS Number 365564-05-2

  • Empirical Formula (Hill Notation) C24H39B3O6

  • Molecular Weight 456.00

  •  MDL number MFCD17167305

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Properties

Related Categories Boronate Esters, Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Boronate Esters, Organometallic Reagents More...
Quality Level   100
assay   ≥97%
form   powder or crystals
mp   286-287 °C
SMILES string   CC1(C)OB(OC1(C)C)C2=CC(B3OC(C)(C)C(C)(C)O3)=CC(B4OC(C)(C)C(C)(C)O4)=C2
InChI   1S/C24H39B3O6/c1-19(2)20(3,4)29-25(28-19)16-13-17(26-30-21(5,6)22(7,8)31-26)15-18(14-16)27-32-23(9,10)24(11,12)33-27/h13-15H,1-12H3
InChI key   VKOLBYNBPONPAE-UHFFFAOYSA-N

Description

Application

1,3,5-Phenyltriboronic acid, tris(pinacol) ester can undergo Suzuki–Miyaura cross-coupling polycondensation reaction with 4,7-dibromobenzo[c][1,2,5]thiadiazole to afford conjugated polybenzothiadiazoles. It may also be used as a crosslinker for synthesizing conjugated microporous polymer (CMP) nanoparticles. This product was previously listed as BML00299.

Other Notes

Molecular engineering of conjugated polybenzothiadiazoles for enhanced hydrogen production by photosynthesis

Conjugated microporous polymer nanoparticles with enhanced dispersibility and water compatibility for photocatalytic applications

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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