913-86-0

Basic information

• Product Name: 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL
• Synonyms: 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL;Tetrakismethylphenylethanediol;1,1,2,2-Tetra(4-methylphenyl)ethane-1,2-diol;1,1,2,2-Tetrakis(4-methylphenyl)ethane-1,2-diol;1,1,2,2-Tetra-p-tolylethane-1,2-diol;Tetrakis(4-methylphenyl)-1,2-ethanediol;1,1,2,2-TETRA-P-TOLYL-1,2-ETHANEDIOL
• CAS NO: 913-86-0
• Molecular Formula: C₃₀H₃₀O₂
• Molecular Weight: 422.56
• Mol File: 913-86-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 177 °C
• Boiling Point: 560 °C at 760 mmHg
• Flash Point: 239 °C
• Appearance: /
• Density: 1.139 g/cm³
• CAS DataBase Reference: 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL(913-86-0)
• EPA Substance Registry System: 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL(913-86-0)

Safety Data

• Hazardous Substances Data: 913-86-0(Hazardous Substances Data)

Usage

General Description

1,1,2,2-Tetrakis(4-methylphenyl)-1,2-ethanediol is a chemical compound commonly used as an antioxidant in various industrial and commercial applications. It is a white, crystalline solid that is soluble in organic solvents. 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL is known for its ability to inhibit the oxidation of materials, which makes it valuable for preserving the quality and stability of products such as plastics, rubber, and lubricants. Additionally, 1,1,2,2-Tetrakis(4-methylphenyl)-1,2-ethanediol is also used in the production of pharmaceuticals and personal care products due to its antioxidant properties. Despite its usefulness, caution should be taken when handling this compound, as it may cause skin and eye irritation and should be used in a well-ventilated area.

Upstream product

• 611-97-2 bis(p-methylphenyl)-methanone 
• 122-51-0 orthoformic acid triethyl ester 
• 885-77-8 4,4'-dimethylbenzhydrol 
• 67-64-1 acetone 
• 17314-40-8 3-Methyl-2-butenyl-trimethylstannane 
• 762-73-2 trimethyl(allyl)stannane 
• 762-72-1 allyl-trimethyl-silane 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 464-72-2 1,1,2,2-Tetraphenyl-ethane-1,2-diol 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 

Downstream Products

• 464-72-2 tetraphenylethane-1,2-diol 
• 63838-73-3 1,1-diphenyl-2,2-ditolylethanediol 
• 885-77-8 4,4'-dimethylbenzhydrol 
• 1219492-23-5 1,1-bis(4-methylphenyl)-1-(2-methoxyphenyl)-methanol 
• 611-97-2 bis(p-methylphenyl)-methanone 
• 5831-43-6 1,1,2,2-tetrakis(4-methylphenyl)ethylene 
• 19920-02-6 tetrakis(4-methylphenyl)ethanone 

Relevant articles and documents

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

Light-enabled metal-free pinacol coupling by hydrazine

Efficient carbon-carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C-C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N2 and H2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.