879-97-0

Basic information

• Product Name: 4-tert-butyl-2,6-xylenol
• Synonyms: 4-tert-butyl-2,6-xylenol;4-(1,1-Dimethylethyl)-2,6-dimethylphenol
• CAS NO: 879-97-0
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.27072
• EINECS: 212-910-7
• Mol File: 879-97-0.mol

Chemical Properties

• Melting Point: 82.4°C
• Boiling Point: 248.05°C
• Flash Point: 114.7°C
• Appearance: /
• Density: 0.9160
• Vapor Pressure: 0.0158mmHg at 25°C
• Refractive Index: 1.5091 (estimate)
• CAS DataBase Reference: 4-tert-butyl-2,6-xylenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-butyl-2,6-xylenol(879-97-0)
• EPA Substance Registry System: 4-tert-butyl-2,6-xylenol(879-97-0)

Safety Data

• Hazardous Substances Data: 879-97-0(Hazardous Substances Data)

Usage

Uses

Used in Personal Care and Cosmetic Products:
4-tert-butyl-2,6-xylenol is used as an antioxidant and preservative for its ability to inhibit the growth of bacteria and fungi, making it a popular ingredient in soaps, lotions, and other skincare products.
Used in Plastics, Rubbers, and Adhesives Manufacturing:
4-tert-butyl-2,6-xylenol is used as a stabilizer and antioxidant in the manufacturing of plastics, rubbers, and adhesives to prevent degradation and extend the shelf life of these products.
However, there have been concerns about the potential harmful effects of 4-tert-butyl-2,6-xylenol on human health and the environment, leading to regulatory restrictions in some countries.

InChI:InChI=1/C12H18O/c1-8-6-10(12(3,4)5)7-9(2)11(8)13/h6-7,13H,1-5H3

Upstream product

• 42014-60-8 2,6-dimethyl-4-tert-butylaniline 
• 13464-23-8 2-hydroxy-3-methyl-5-tert-butylbenzyl alcohol 
• 576-26-1 2.6-dimethylphenol 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 507-19-7 t-butyl bromide 
• 98-19-1 5-tert-Butyl-m-xylene 
• 2203-14-7 4-tert-butyl-2,5-bis(hydroxymethyl)phenol 
• 98-54-4 para-tert-butylphenol 
• 3634-86-4 bis(2-hydroxy-3-methyl-5-tert-butylphenyl)methane 

Downstream Products

• 86509-74-2 c-4-t-butyl-c-2,c-6-dimethylcyclohexan-r-1-ol 
• 121078-62-4 2-Butoxy-5-tert-butyl-1,3-dimethyl-benzene 
• 85202-97-7 9a-tert-butyl-6a,8-dimethyl-5,6,6a,7,9a,9b-hexahydro-7-oxo-4H-1,2,3-triazolo<4,5,1-ij>benzquinoline 
• 125259-50-9 (15N)-4-t-butyl-2,6-dimethyl-4-nitrocyclohexa-2,5-dienone 
• 91734-85-9 4-t-butyl-c-6-hydroxy-2,6-dimethyl-r-2,c-5-dinitrocyclohex-3-enone 
• 91734-85-9 4-t-butyl-t-6-hydroxy-2,6-dimethyl-r-2,t-5-dinitrocyclohex-3-enone 
• 91734-82-6 4-t-butyl-2,6-dimethyl-r-2,t-5,c-6-trinitrocyclohex-3-enone 
• 91734-82-6 4-t-butyl-2,6-dimethyl-r-2,c-5,t-6-trinitrocyclohex-3-enone 
• 91734-82-6 4-t-butyl-2,6-dimethyl-r-2,t-5,t-6-trinitrocyclohex-3-enone 
• 91734-82-6 4-t-butyl-2,6-dimethyl-r-2,c-5,c-6-trinitrocyclohex-3-enone 
• 91734-80-4 c-6-hydroxy-2,6-dimethyl-r-2,4-c-5-trinitrocyclohex-3-enone 
• 91734-80-4 t-6-hydroxy-2,6-dimethyl-r-2,4,t-5-trinitrocyclohex-3-enone 
• 30168-86-6 2,6-Dimethyl-4-<(3,5-dichloro-4-hydroxypenyl)imino>-2,5-cyclohexadien-1-one 
• 26319-95-9 4-tert-Butyl-2,6-dimethylphenyl-allylether 

Relevant articles and documents

Catalytic Activation of Unstrained C(Aryl)-C(Alkyl) Bonds in 2,2′-Methylenediphenols

Catalytic activation of unstrained and nonpolar C-C bonds remains a largely unmet challenge. Here, we describe our detailed efforts in developing a rhodium-catalyzed hydrogenolysis of unstrained C(aryl)-C(alkyl) bonds in 2,2′-methylenediphenols aided by removable directing groups. Good yields of the monophenol products are obtained with tolerating a wide range of functional groups. In addition, the reaction is scalable, and the catalyst loading can be reduced to as low as 0.5 mol %. Moreover, this method proves to be effective to cleave C(aryl)-C(alkyl) linkages in both models of phenolic resins and commercial novolacs resins. Finally, detailed experimental and computational mechanistic studies show that with C-H activation being a competitive but reversible off-cycle reaction, this transformation goes through a directed C(aryl)-C(alkyl) oxidative addition pathway.

Site-selective Oxidative Dearomatization of Phenols and Naphthols into ortho-Quinols or Epoxy ortho-Quinols using Oxone as the Source of Dimethyldioxirane

A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step. (Figure presented.).

Process preparation method of 4-substituted-2, 6-dimethylphenol

The present invention discloses a process preparation method of 4-substituted-2, 6-dimethyl phenol. According to the process preparation method, a preparation route method is improved and optimized, reaction conditions are optimized, post-treatment and purification methods are improved, so that the danger grade of operation and the production cost are reduced; and the requirement for the corrosionresistance grade of reaction container equipment is low, the operation is safe, and the post-treatment is environment-friendly; and the prepared 4-substituted-2, 6-dimethyl phenol has less impurities, thus, the purity and the quality of an intermediate product are greatly improved while the yield is improved as well, the difficulty of process control in the production process of a subsequent rawmaterial medicine product is improved, and the quality and qualification rate of the subsequent raw material medicine product are improved; and the steps of the preparation method is simple to operate, the solvent and the process conditions are safe and easy to achieve, environment-friendly production is achieved, and the preparation method has wide application prospect.

Synthesis of phenols and aryl silyl ethers via arylation of complementary hydroxide surrogates

Two transition-metal-free methods to access substituted phenols via the arylation of silanols or hydrogen peroxide with diaryliodonium salts are presented. The complementary reactivity of the two nucleophiles allows synthesis of a broad range of phenols without competing aryne formation, as illustrated by the synthesis of the anesthetic Propofol. Furthermore, silyl-protected phenols can easily be obtained, which are suitable for further transformations.

C-H borylation by platinum catalysis

Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.

An Unprecedented Photochemical Reaction for Anthracene-Containing Derivatives

A series of anthracene-containing derivatives have been synthesised and characterised. The photochemical behaviour of these derivatives have been investigated by 1H NMR spectroscopy. An unprecedented photolysis reaction for anthracene-containing derivatives was observed in the case of anthracenes directly armed with a -CH2O-R group upon UV irradiation. The photolysis reaction process has been demonstrated to occur in three steps. Firstly, the anthracene-containing derivatives are converted into the corresponding endoperoxide intermediate upon UV irradiation in the presence of air; then, the endoperoxide intermediate is decomposed to the corresponding starting compound and 9-anthraldehyde; finally, 9-anthraldehyde is further oxidised to anthraquinone. Additionally, the photolysis reaction of anthracene-containing derivatives is significantly promoted in the presence of a thiacalix[4]arene platform.

C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes

Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.

Partial OH → Me Replacement in the Calixarene Scaffold: Preparation, Conformation, and Stereodynamics of Tetra-terf-butyl-25,27-dihydroxy-26,28-dimethylcalix[4]arene and Its Dimethyl Ether Derivative

The first example of the replacement of hydroxyl groups of a calixarene by methyls is described. Reaction of the bis(spirodienone) calixarene derivative 3B with MeLi afforded the bis addition product 4 which is derived, as shown by X-ray crystallography, from attack on the face of the carbonyls which is anti to the ether oxygen. The reaction of the alternant bis(spirodienone) calixarene derivative 3A with excess MeLi resulted in addition to the C=O groups, but with a concomitant cleavage of the spiro bonds. Ionic hydrogenation (CF3COOH/Et3SiH) of this product (5) yielded 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dimethylcalix[4]arene (6) while ionic hydrogenation of 4 resulted in fragmentation of the macrocyclic ring. Calixarene 6 adopts a 1,3-alternate conformation both in solution and in the solid state. 6 is conformationally flexible, and an inversion barrier of 15.1 kcal mol-1 was measured for it by DNMR. The dimethyl ether derivative of 6 (i.e., 7) exists in a partial cone (paco) conformation and undergoes two distinct dynamic processes possessing barriers of 13.3 and 18.1 kcal mol-1. Molecular mechanics calculations predict correctly the preferred conformation of 6 and 7 and indicate that the topomerization pathways resulting in the mutual exchange of the protons within a methylene group are the following: 1,3-alt → paco(CH3) → 1,2 alt → paco(CH3)* → 1,3-alt* for 6, and paco(CH3) → 1,3-alt → paco(OCH3) → 1,2 alt → paco(OCH3)* → 1,3-alt* → paco(CH3)* for 7 with calculated barriers of 15.0 and 16.1 kcal mol-1, respectively.

Silica Gel as an Effective Catalyst for the Alkylation of Phenols and Some Heterocyclic Compounds

In the presence of silica gel, the reaction of phenol with t-BuBr was examined under a variety of conditions and it was found that silica gel is an effective catalyst for the alkylation.As a result of this work 2-tert-butyl-, 2,6-di-tert-butyl-, and 2,4,6-tri-tert-butylphenols, all of which are hard to obtain directly by the Friedel-Crafts process, could be prepared easily by this one-step reaction.Several other alkyl halides were also used in this reaction.The alkylations of some heterocyclic aromatic compounds which cannot be alkylated by the conventional Friedel-Crafts method were also succesfully performed by this reaction.