90-68-6

Basic information

• Product Name: 2,6-bis[[3-(tert-butyl)-2-hydroxy-5-tolyl]methyl]-4-methylphenol
• Synonyms: 2,6-bis[[3-(tert-butyl)-2-hydroxy-5-tolyl]methyl]-4-methylphenol;2,6-BIS(3-TERT-BUTYL-2-HYDROXY-5-METHYLBENZYL)-4-METHYLPHENOL;2,6-BIS(3-TERT-BUTYL-2-HYDROXY-5-METHYLBENZYL)-4-METHYLPHENO;2,2'-[(2-Hydroxy-5-methyl-1,3-phenylene)bismethylene]bis(4-methyl-6-tert-butylphenol);2,6-Bis(2-hydroxy-3-tert-butyl-5-methylbenzyl)-4-methylphenol;2,6-Bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol;2,6-Bis[[3-(1,1-dimethylethyl)-2-hydroxy-5-methylphenyl]methyl]-4-methylphenol
• CAS NO: 90-68-6
• Molecular Formula: C₃₁H₄₀O₃
• Molecular Weight: 460.6475
• EINECS: 202-011-8
• Mol File: 90-68-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 562.1°C at 760 mmHg
• Flash Point: 229.7°C
• Appearance: /
• Density: 1.082g/cm³
• Vapor Pressure: 3.06E-13mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 2,6-bis[[3-(tert-butyl)-2-hydroxy-5-tolyl]methyl]-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis[[3-(tert-butyl)-2-hydroxy-5-tolyl]methyl]-4-methylphenol(90-68-6)
• EPA Substance Registry System: 2,6-bis[[3-(tert-butyl)-2-hydroxy-5-tolyl]methyl]-4-methylphenol(90-68-6)

Safety Data

• Hazardous Substances Data: 90-68-6(Hazardous Substances Data)

Usage

General Description

2,6-bis[[3-(tert-butyl)-2-hydroxy-5-tolyl]methyl]-4-methylphenol, also known as BHT or butylated hydroxytoluene, is a synthetic antioxidant commonly used in food, cosmetics, and industrial products. It is a white crystalline powder that is insoluble in water but soluble in organic solvents. BHT is added to products to prevent oxidative rancidity and extend shelf life by inhibiting the formation of free radicals. However, there is some controversy surrounding its safety and potential health risks, as high doses have been linked to liver and kidney damage in animal studies, and it has been classified as a possible human carcinogen by some organizations. Despite this, BHT is still widely used in many consumer products.

InChI:InChI=1/C31H40O3/c1-18-10-21(16-23-12-19(2)14-25(28(23)33)30(4,5)6)27(32)22(11-18)17-24-13-20(3)15-26(29(24)34)31(7,8)9/h10-15,32-34H,16-17H2,1-9H3

Upstream product

• 91-04-3 2,6-bis(hydroxymethyl)-4-methylphenol 
• 2409-55-4 2-tert-Butyl-4-methylphenol 

Downstream Products

• 251920-11-3 4-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-6-diethylamino-2,10-dimethyldibenzo[d.g][1.3.2]dioxaphosphocin 
• 245058-02-0 6-diethylamino-4-(2-hydroxy-5-methylbenzyl)-2,10-dimethyldibenzo<1,3,2>-dioxaphosphacane 
• 6079-81-8 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methyl-anisole 
• 245058-03-1 8-tert-butyl-6-diethylamino-4-(2-hydroxy-3-tert-butyl-5-methylbenzyl)-2,10-dimethyldibenzo<1,3,2>-dioxaphosphacane 
• 35924-10-8 2,2'-dihydroxy-3-tert-butyl-3'-(2-hydroxy-5-methylbenzyl)-5,5'-dimethyldiphenylmethane 
• 1620-68-4 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol 

Relevant articles and documents

Solvent-free synthesis of trisphenols as starting precursors for the synthesis of calix[4]arenes using sulfonated multi-walled carbon nanotubes

The condensation of phenol derivatives (12 substrates) with 2,6-bis(hydroxymethyl)phenols (BMP) (6 examples) is reported using sulfonated multi-walled carbon nanotubes (SO3H@MWCNTs) under solvent-free conditions as starting precursors for the synthesis of macrocyclic molecules of calix[4]arenes. The new protocol provides a series of trisphenol derivatives (21 examples) in high yields (up to 94%) and relatively short reaction times (15-120 min). Also, direct synthesis of calix[4]arenes from different trisphenols by use of the catalyst was reported (5 examples). Furthermore, the synthesized calix[4]arene was obtained using a one-pot method from simple and easily available starting materials such as p-cresol for the synthesis of 5,11,17,23-tetramethylcalix[4]arene-25,26,27,28-tetraol. Also, in this process SO3H@MWCNTs can be reused for seven runs with almost consistent efficiency and can be recovered by easy filtration.

Lubricant composition

A composition comprising a) a lubricant or a hydraulic fluid and b) at least one compound of the general formula I STR1 in which x=1 or 2 and, if x=1, R is as defined for R1 or R3 --O-- or, if x=2, R is as defined for R8, and R1 and R3 are, for example, alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, or alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3, or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR2 or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3 and interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR3 and R2 is NR4 R5, --OR6 or --SR7, and R4 and R5 are identical or different and are, for example, --H, alkyl, phenyl, naphthyl, aralkyl or alkaryl, or R4 and R5, together with the N atom linking them, form, for example, a piperidine or morpholine radical, and R6 and R7 can be alkyl which may be interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR4 or are, for example, phenyl, naphthyl, alkaryl or aralkyl, and R8 can be alkylene which may be interrupted by at least one --O-- group or alkylidene which may be interrupted by at least one --O-- group. Some of the compounds of the formula I are novel. The compositions show an improved stability towards oxidative degradation, confer protection under extreme pressures and reduce frictional wear.

Metal-template ortho-regioselective mono- and bis-de-tert-butylation of poly-tert-butylated phenols

A metal-template ortho-regioselective mono- and bis-de-tert-butylation of poly-tert-butylated phenol-formaldehyde oligomers is reported.