269410-25-5

Basic information

• Product Name: 2,6-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL
• Synonyms: 2-(4-HYDROXY-3,5-DIMETHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2,6-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL;2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol,min.97%;3,5-Dimethyl-4-hydroxybenzeneboronic acid, pinacol ester;2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-;3,5-Dimethyl-4-hydroxyphenylboronic acid pinacol ester, 4-Hydroxy-3,5-dimethylphenylboronic acid, pinacol cyclic ester, 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, min. 97%;2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol,97%
• CAS NO: 269410-25-5
• Molecular Formula: C₁₄H₂₁BO₃
• Molecular Weight: 248.13
• Product Categories: Phenoles and thiophenoles;Heterocyclic Compounds;B (Classes of Boron Compounds);Boronic Acids Esters;organic or inorganic borate
• Mol File: 269410-25-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 100-105 °C(lit.)
• Boiling Point: 367.3 °C at 760 mmHg
• Flash Point: 176 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.06 g/cm³
• Vapor Pressure: 6.51E-06mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: Refrigerator (+4°C)
• PKA: 10.36±0.40(Predicted)
• Water Solubility: Insoluble in water
• CAS DataBase Reference: 2,6-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(269410-25-5)
• EPA Substance Registry System: 2,6-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(269410-25-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 269410-25-5(Hazardous Substances Data)

Usage

Chemical Properties

white to beige crystalline powder

Uses

3,5-Dimethyl-4-hydroxyphenylboronic acid, pinacol ester

InChI:InChI=1/C14H21BO3/c1-9-7-11(8-10(2)12(9)16)15-17-13(3,4)14(5,6)18-15/h7-8,16H,1-6H3

Upstream product

• 2374-05-2 4-bromo-2,6-dimethyl-phenol 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 934826-20-7 4-hydroxy-3,5-dimethylphenylboronic acid 

Downstream Products

• 1309682-18-5 4-(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)-2,6-dimethylphenol 
• 1404166-49-9 bis(3,5-dimethyl-4-hydroxy)phenyl-3,3'-dipentoxy-2,2'-bithiophene 
• 1321513-22-7 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2,6-dimethylphenol 
• 1309680-46-3 4-{[ 6-(4-hydroxy-3,5-dimethylphenyl)[1,2,4]triazolo[ 1,5-a]pyridin-2-yl]amino}-3-methoxybenzonitrile 
• 934826-20-7 4-hydroxy-3,5-dimethylphenylboronic acid 
• 1250968-57-0 4-(3-aminoquinoxalin-6-yl)-2,6-dimethylphenol 
• 869852-31-3 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-propan-1-one 
• 869852-16-4 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-ethanone 
• 1075196-45-0 2-(3,5-Dimethyl-4-propoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 870098-73-0 6-(tert-butyldimethylsiloxymethyl)-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester 
• 864780-61-0 4-[6-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-6-(4-hydroxy-3,5-dimethyl-phenyl)-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyridazin-3-one 

Relevant articles and documents

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.