527-18-4

Basic information

• Product Name: DUROHYDROQUINONE
• Synonyms: 1,4-Benzenediol, 2,3,5,6-tetramethyl-;2,3,5,6-Tetramethyl-1,4-benzenediol;2,3,5,6-Tetramethylhydroquinone;Duro-p-hydroquinone;Hydroquinone, tetramethyl-;DUROHYDROQUINONE;DIHYDROXYDURENE;TETRAMETHYLHYDROQUINONE
• CAS NO: 527-18-4
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol File: 527-18-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: 233°
• Boiling Point: 254.44°C (rough estimate)
• Flash Point: 151.3°C
• Appearance: /
• Density: 1.0060 (rough estimate)
• Vapor Pressure: 0.000297mmHg at 25°C
• Refractive Index: 1.5277 (estimate)
• Solubility: almost transparency in hot Methanol
• PKA: 11.33±0.33(Predicted)
• Merck: 14,3469
• CAS DataBase Reference: DUROHYDROQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: DUROHYDROQUINONE(527-18-4)
• EPA Substance Registry System: DUROHYDROQUINONE(527-18-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 527-18-4(Hazardous Substances Data)

Usage

General Description

Durohydroquinone is a chemical compound used in the production of antioxidants and pharmaceuticals. It is a derivative of hydroquinone, a common ingredient found in skincare and haircare products. Durohydroquinone is known for its ability to inhibit melanin production, making it effective in the treatment of hyperpigmentation and skin discoloration. It is also used in the synthesis of complex organic compounds, particularly in the manufacture of pharmaceuticals. Additionally, durohydroquinone is utilized as a stabilizer and antioxidant in food and beverage packaging materials, helping to extend the shelf life of perishable products. However, due to its potential harmful effects on the environment and human health, the use of durohydroquinone is subject to strict regulations and guidelines.

InChI:InChI=1/C10H14O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h11-12H,1-4H3

Upstream product

• 527-17-3 Duroquinone 
• 68-11-1 mercaptoacetic acid 
• 94-71-3 2-Ethoxyphenol 
• 503-17-3 dimethylacetylene 
• 59-02-9 Tocopherol 
• 22311-37-1 durosemiquinone radical 
• 97-93-8 triethylaluminum 
• 996-82-7 sodium diethylmalonate 
• 71-43-2 benzene 
• 100-63-0 phenylhydrazine 
• 62-53-3 aniline 
• 873977-07-2 1,4-bis-hexadecyloxy-2,3,5,6-tetramethyl-benzene 
• 103043-11-4 4-Hexadecyloxy-2,3,5,6-tetramethyl-phenol 
• 700-12-9 pentamethylbenzene, 

Downstream Products

• 139200-62-7 1,2,4,5-Tetramethyl-3,6-dipropoxy-benzene 
• 120255-25-6 1,4-Bis(methoxymethoxy)-2,3,5,6-tetramethylbenzol 
• 21219-18-1 4-Benzoyloxy-2,3,5,6-tetramethyl-phenol 
• 5796-23-6 1,4-diacetoxy-2,3,5,6-tetramethylbenzene 
• 22311-37-1 durosemiquinone radical 
• 527-35-5 2,3,5,6-tetramethylphenol 
• 527-17-3 Duroquinone 
• 873977-07-2 1,4-bis-hexadecyloxy-2,3,5,6-tetramethyl-benzene 
• 103043-11-4 4-Hexadecyloxy-2,3,5,6-tetramethyl-phenol 
• 100964-15-6 Butyl-(4-hydroxy-2.3.5.6-tetramethyl-phenyl)-aether 
• 139200-63-8 1,4-dibutoxy-2,3,5,6-tetramethyl-benzene 

Relevant articles and documents

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Preparation, crystal structure and photochemistry of a novel molecular compound between duroquinone and durene

A 2:1 crystalline molecular compound (3) of duroquinone (1) and durene (2) has been prepared in two ways of evaporating the solution and solidifying the melt. The crystal structure of 3 was determined by X-ray crystallography. Irradiation of 3 caused the intermolecular hydrogen abstraction reaction, which was specific in the solid state, to give durohydroquinone (4) and a photoadduct (5).

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.

Reactivity of iPrPCPIrH4 with para-benzoquinones

In the interest of investigating new hydrogen acceptors for pincer–iridium catalyzed dehydrogenations with the ability to be catalytically recycled, a series of para-benzoquinones have been reacted with iPrPCPIrH4 in various solvents and conditions. Preliminary results indicate that a wide range of quinones are capable of dehydrogenating iPrPCPIrH4, and that several turn-overs in alcohol dehydrogenation by iPrPCPIr are possible at room temperature using benzoquinone acceptors. However, strong acceptor–catalyst interactions are inhibitory toward catalysis when the acceptor is used in excess. A new class of (bis)-η2 pi-adducts, formed between iPrPCPIr and benzoquinones, nicknamed “barber-chairs”, has been identified and 3 examples have been characterized.