889659-70-5

Basic information

• Product Name: 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol
• Synonyms: 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol;3-Hydroxy-5-methylphenylboronic acid, pinacol ester
• CAS NO: 889659-70-5
• Molecular Formula: C₁₃H₁₉BO₃
• Molecular Weight: 234.09916
• Mol File: 889659-70-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol(889659-70-5)
• EPA Substance Registry System: 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol(889659-70-5)

Safety Data

• Hazardous Substances Data: 889659-70-5(Hazardous Substances Data)

Usage

Uses

Used in Rubber Industry:
3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol is used as an antiozonant for rubber products to prevent the damaging effects of ozone on rubber, thereby enhancing the durability and longevity of rubber materials.
Used in Plastics and Rubber Materials:
3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol is used as an antioxidant in plastics and rubber materials to protect them from degradation caused by heat, light, and oxygen, ensuring the stability and performance of these materials over time.
Used in Flame Retardancy:
3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol is used as a flame retardant in various industrial applications to improve the fire resistance of materials, offering a safer alternative to traditional flame retardants due to its lower toxicity and environmental impact.
Used in Industrial Applications:
3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol is utilized in a variety of industrial applications to enhance the durability and longevity of materials, thanks to its high thermal stability and effectiveness in inhibiting the degradation of polymers.

Upstream product

• 504-15-4 orcinol 
• 889659-69-2 3-hydroxy-5-methylphenyl trifluoromethanesulfonate 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1256346-05-0 (3-ethoxy-5-methylphenyl)boronic acid 
• 1256345-76-2 (3-isopropoxy-5-methylphenyl)boronic acid 
• 1256355-61-9 (3-(benzyloxy)-5-methylphenyl)boronic acid 

Relevant articles and documents

Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion

Enantioselectivity values represent relative rate measurements that are sensitive to the structural features of the substrates and catalysts interacting to produce them. Therefore, well-designed enantioselectivity data sets are information rich and can provide key insights regarding specific molecular interactions. However, if the mechanism for enantioselection varies throughout a data set, these values cannot be easily compared. This premise, which is the crux of free energy relationships, exposes a challenging issue of identifying mechanistic breaks within multivariate correlations. Herein, we describe an approach to addressing this problem in the context of a chiral phosphoric acid catalyzed fluorination of allylic alcohols using aryl boronic acids as transient directing groups. By designing a data set in which both the phosphoric and boronic acid structures were systematically varied, key enantioselectivity outliers were identified and analyzed. A mechanistic study was executed to reveal the structural origins of these outliers, which was consistent with the presence of several mechanistic regimes within the data set. While 2- and 4-substituted aryl boronic acids favored the (R)-enantiomer with most of the studied catalysts, meta-alkoxy substituted aryl boronic acids resulted in the (S)-enantiomer when used in combination with certain (R)-phosphoric acids. We propose that this selectivity reversal is the result of a lone pair-π interaction between the substrate ligated boronic acid and the phosphate. On the basis of this proposal, a catalyst system was identified, capable of producing either enantiomer in high enantioselectivity (77% (R)-2 to 92% (S)-2) using the same chiral catalyst by subtly changing the structure of the achiral boronic acid.

Novel azo dye compound

A compound represented by formula (I): Formula (I) wherein Z1 and Z2 each are atoms necessary for forming an aromatic ring; V1 and V2 each are a substituent W1 or W2; when at least one V1 is W1, at least one V2 is W2, or when at least one V1 is W2, at least one V2 is W1; r is 1 to 4; s is 1 to 4; M1 is a counter ion; m1 is the number necessary for neutralizing charge; W1 is a hydroxyl, primary- or secondary- or tertiary-amino, acylamino, or sulfonamido group; W2 is a nitro, cyano, alkoxycarbonyl, aryloxycarbonyl, alkyl- or aryl-sulfonyl, carbamoyl, sulfamoyl, alkenyl, alkynyl, aryl, heterocyclic, sulfo, carboxyl, heterocyclic oxy, ammonio, alkyl- or aryl-sulfinyl, alkyl- or aryl-sulfonyl, acyl, or aryl- or heterocyclic-azo group; and the aromatic ring may have a substituent other than V1 and V2.