2-Phenyl-1,3,2-dioxaborolane

• CAS: 4406-72-8
• Catalog Number: ACM4406728
• Category: Main Products
• Molecular Weight: 147.97
• Molecular Formula: C8H9BO2

Case Study

2-Phenyl-1,3,2-Dioxaborolane: Structural Effects on Boronic-Ester Stability and Transesterification Behavior

Roy, Chandra D., et al. Journal of organometallic chemistry 692.4 (2007): 784-790.

2-Phenyl-1,3,2-dioxaborolane was subjected to transesterification reactions with a wide variety of structurally modified diols. The study systematically compared the relative rates of these reactions and the resulting equilibrium compositions. Key structural variables examined included the ring size of the resulting boronic ester, the stereochemistry of cyclic 1,2-diols, the influence of alkyl substituents on the diol, and the chelating ability of heteroatom-containing diols.
· Steric substitution on diols: Alkyl substituents on the α-carbons of diols slow transesterification (kinetic effect) but increase the thermodynamic stability of the resulting boronic ester.
· Ring size matters: Six-membered boronic esters are thermodynamically more stable than the analogous five-membered species.
· Stereochemistry: For cyclic 1,2-diols, cis geometry is required for exchange - cis-1,2-cyclopentanediol displaces ethylene glycol almost instantaneously, whereas trans-1,2-cyclopentanediol is essentially unreactive. cis-1,2-cyclohexanediol displaces ethylene glycol only partially (≈48% conversion), suggesting ring strain and conformational accessibility modulate reactivity.
· Steric tuning: Among substituted cis-1,2-cyclopentanediols, the isopropyl substituent most strongly drives equilibrium toward the new boronic ester (i.e., produces the most stable ester), while cis-1,2-dimethylcyclopentanediol is the most sterically hindered and less favorable for exchange.
· Chelation: Diethanolamine rapidly displaces ethylene glycol and forms a stable bicyclic chelate in which nitrogen coordinates to boron. N-methyldiethanolamine is less effective (~70% conversion), and N-tert-butyldiethanolamine fails to displace ethylene glycol, indicating that substitution at nitrogen can block chelate formation.

Custom Q&A

What is the molecular formula of 2-Phenyl-1,3,2-dioxaborolane?

The molecular formula of 2-Phenyl-1,3,2-dioxaborolane is C8H9BO2.

What are some synonyms for 2-Phenyl-1,3,2-dioxaborolane?

Some synonyms for 2-Phenyl-1,3,2-dioxaborolane include "1,3,2-Dioxaborolane, 2-phenyl-", "Benzeneboronic acid, cyclic ethylene ester", and "starbld0012963".

What is the molecular weight of 2-Phenyl-1,3,2-dioxaborolane?

The molecular weight of 2-Phenyl-1,3,2-dioxaborolane is 147.97 g/mol.

When was 2-Phenyl-1,3,2-dioxaborolane created?

2-Phenyl-1,3,2-dioxaborolane was created on March 27, 2005.

What is the IUPAC name of 2-Phenyl-1,3,2-dioxaborolane?

The IUPAC name of 2-Phenyl-1,3,2-dioxaborolane is "2-phenyl-1,3,2-dioxaborolane".

What is the InChI of 2-Phenyl-1,3,2-dioxaborolane?

The InChI of 2-Phenyl-1,3,2-dioxaborolane is "InChI=1S/C8H9BO2/c1-2-4-8(5-3-1)9-10-6-7-11-9/h1-5H,6-7H2".

What is the InChIKey of 2-Phenyl-1,3,2-dioxaborolane?

The InChIKey of 2-Phenyl-1,3,2-dioxaborolane is "HVEMPDZEMICSMG-UHFFFAOYSA-N".

What is the canonical SMILES of 2-Phenyl-1,3,2-dioxaborolane?

The canonical SMILES of 2-Phenyl-1,3,2-dioxaborolane is "B1(OCCO1)C2=CC=CC=C2".

What is the CAS number of 2-Phenyl-1,3,2-dioxaborolane?

The CAS number of 2-Phenyl-1,3,2-dioxaborolane is 4406-72-8.

What is the hydrogen bond acceptor count of 2-Phenyl-1,3,2-dioxaborolane?

The hydrogen bond acceptor count of 2-Phenyl-1,3,2-dioxaborolane is 2.