4406-75-1

Basic information

• Product Name: 1,3,2-Dioxaborolane, 4-methyl-2-phenyl-
• CAS NO: 4406-75-1
• Molecular Formula: C9H11BO2
• Molecular Weight: 161.996
• Mol File: 4406-75-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 54-56 °C(Press: 0.5 Torr)
• Density: 1.03±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,3,2-Dioxaborolane, 4-methyl-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborolane, 4-methyl-2-phenyl-(4406-75-1)
• EPA Substance Registry System: 1,3,2-Dioxaborolane, 4-methyl-2-phenyl-(4406-75-1)

Safety Data

• Hazardous Substances Data: 4406-75-1(Hazardous Substances Data)

Usage

Type of compound

Boronic acid derivative

Usage

Building block in organic synthesis

Applications

Formation of carbon-carbon and carbon-heteroatom bonds

Industries

Pharmaceutical and agrochemical

Physical state

Clear, colorless liquid at room temperature

Sensitivity

Air, moisture, and heat

Flammability

Flammable

Safety precautions

Handle with care in a well-ventilated area

Upstream product

• 57-55-6 propylene glycol 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 53774-64-4 phenylboronic acid 1,2-butanediol ester 
• 98-80-6 phenylboronic acid 
• 2848-16-0 diphenyldiboronic acid 

Downstream Products

• 6638-66-0 phenylboronic acid 1,3-butanediol ester 

Relevant articles and documents

COMPOUND LIBRARY PREPARATION PROCESS BASED ON EXCHANGE REACTION BETWEEN DIFERENTLY SUBSTITUTED DIOXABOROLANES OR DIOXABORINANES

The present invention relates to the preparation of a compound library comprising the following steps: ? i. Having available at least two different compounds each comprising at least a dioxaborolane or dioxaborinane ring. In said compounds: ? -the boron of the dioxaborolane or dioxaborinane ring is directly linked to a carbon atom of a hydrocarbon radical; ? -at least one carbon atom of the dioxaborolane or dioxaborinane ring is monosubstituted, the other carbon atoms are non- substituted or monosubstituted; ? -in at least two compounds, the hydrocarbon radicals linked to the boron are different; ? - in at least two compounds, either the dioxaborolane or dioxaborinane ring carbon atoms are differently substituted and/ or the size varies. ? ii. Reacting the compounds of step (i.) and forming, by a boronic ester metathesis reaction, the library comprising at least four different compounds. The present invention also relates to a compound library. Illustrative for the present invention is the following figure:

Stability of boronic esters - Structural effects on the relative rates of transesterification of 2-(phenyl)-1,3,2-dioxaborolane

Relative rates of reaction of the achiral cyclic phenylboronic ester 2-(phenyl)-1,3,2-dioxaborolane with a wide variety of structurally modified diols, have been studied to understand the factors influencing the relative stabilities of boronic esters. It is found that the alkyl substituents on the α-carbons of diols slow down the transesterification, but produce thermodynamically more stable boronic ester. Six-membered boronic esters are thermodynamically more stable than their corresponding five-membered analogs. Amongst cyclic 1,2-diols, cis-1,2-cyclopentanediol displaces ethylene glycol instantaneously whereas trans-1,2-cyclopentanediol is totally unreactive, which suggests that the cis-stereochemistry of the 1,2-diol is a prerequisite for transesterification. Among the 1,5-diols, diethanolamine displaces ethylene glycol quite rapidly forming a more stable bicyclic chelate in which nitrogen is attached to boron by a coordinating bond (as evident by 11B NMR spectroscopy). The oxygen atom of di(ethylene glycol) and the sulfur atom of 2,2′-thiodiethanol do not assist in displacing the ethylene glycol from their boronic esters.

Diol lipids - Communication 27. Identification of C2-C4-diols in the form of cyclic esters of phenylboric acid by the method of combined gas chromatography and mass spectrometry

1. A new method was proposed for the analysis of small quantities of C2-C4-diols, formed in the cleavage of lipids, based on combined gas-chromatography and mass spectrography of their phenylborate esters. 2. Phenylborate esters of d