1,4-Benzoquinone

Base Information

• Chemical Name: 1,4-Benzoquinone
• CAS No.: 106-51-4
• Molecular Formula: C6H4O2
• Molecular Weight: 108.097
• Hs Code.: H4(=O)2 MOL WT. 108.1
• European Community (EC) Number: 203-405-2,946-235-0
• ICSC Number: 0779
• NSC Number: 36324
• UN Number: 2587
• UNII: 3T006GV98U
• DSSTox Substance ID: DTXSID6020145
• Nikkaji Number: J5.052K,J952.047C,J956.405E
• Wikipedia: 1,4-Benzoquinone
• Wikidata: Q402719
• NCI Thesaurus Code: C95317
• Pharos Ligand ID: 8VAZT25NR7BJ
• Metabolomics Workbench ID: 38307
• ChEMBL ID: CHEMBL8320
• Mol file: 106-51-4.mol

Synonyms:1,4-benzoquinone;2,5-cyclohexadiene-1,4-dione;benzoquinone;NSC-36324;NSC36324;p-benzoquinone;para-benzoquinone;quinone

Chemical Property of 1,4-Benzoquinone

Chemical Property:

• Appearance/Colour: gold powder
• Vapor Pressure: 0.166mmHg at 25°C
• Melting Point: 113-115 ºC
• Refractive Index: n20/D 1.453
• Boiling Point: 174 ºC at 760 mmHg
• PKA: 7.7
• Flash Point: 59.3 ºC
• PSA: 34.14000
• Density: 1.256 g/cm³
• LogP: 0.25060
• Storage Temp.: 2-8°C
• Solubility.: 10g/l
• Water Solubility.: 10 g/L (25℃)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.021129366
• Heavy Atom Count: 8
• Complexity: 149
• Transport DOT Label: Poison

Purity/Quality:

99%min ^*data from raw suppliers

p-Benzoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,Xi,F
• Hazard Codes: T:Toxic;;
• Statements: R23/25:; R36/37/38:; R50:
• Safety Statements: S26:; S28A:; S45:; S61:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: C1=CC(=O)C=CC1=O
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the eyes. Exposure far above the OEL could cause respiratory failure and death.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the skin and eyes. This may result in discolouration, inflammation and injury of the corneal epithelium.
• Description: Quinone (p-benzoquinone) exists as a large yellow, monoclinic prism with an irritating odour resembling that of chlorine. Quinone is extensively used as a chemical intermediate, a polymerisation inhibitor, an oxidising agent, a photographic chemical, a tanning agent, and a chemical reagent. Quinone (p-benzoquinone) was first produced commercially in 1919 and has since been manufactured in several European countries. Its major use is in hydroquinone production, but it is also used as a polymerisation inhibitor and as an intermediate in the production of a variety of substances, including rubber accelerators and oxidising agents. It is used in the dye, textile, chemical, tanning, and cosmetic industries. In chemical synthesis for hydroquinone and other chemicals, quinone is used as an intermediate. It is also used in the manufacturing industries and chemical laboratory associated with protein fibre, photographic film, hydrogen peroxide, and gelatin making. Occupational exposure to quinone may occur in the dye, textile, chemical, tanning, and cosmetic industries. Inhalation exposure to quinone may occur from tobacco smoke.
• Physical properties: Light yellow crystals with an acrid odor resembling chlorine. Odor threshold concentration is 84 ppb (quoted, Amoore and Hautala, 1983).
• Uses: 1,4-Benzoquinone is used in the manufacture of dyes, fungicide, and hydroquinone; for tanning hides; as an oxidizing agent; in photography; making gelatin insoluble; strengthening animal fibers and as reagent.

Technology Process of 1,4-Benzoquinone

There total 770 articles about 1,4-Benzoquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

benzyl(4-methoxyphenyl)amine (17377-95-6) → benzaldehyde (100-52-7) + p-benzoquinone (106-51-4)

Guidance literature:

With 3-carboxypyridinium dichromate; In acetonitrile; at 20 ℃; for 0h;

DOI:10.1002/hlca.201100404

Reference yield: 77.0%

methoxybenzene (100-66-3) → para-methoxynitrobenzene (100-17-4) + p-benzoquinone (106-51-4)

Guidance literature:

With copper(II) nitrate/zeolite H-Y; for 0.0333333h; Further Variations:; heating mode; times; Product distribution; microwave irradiation;

DOI:10.1080/00397910801982456

Reference yield: 76.0%

benzyl alcohol (100-51-6,185532-71-2) → benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6) + p-benzoquinone (106-51-4)

Guidance literature:

With tert.-butylhydroperoxide; N-Bromosuccinimide; 1⁽⁴⁾,8⁽¹¹⁾,15⁽¹⁸⁾,22⁽²⁵⁾-tetrakis-{(10R,20R)-2-hydroxy-10,20-diphenylethoxy}phthalocyaninato cobalt(II); In acetonitrile; at 80 ℃; Reagent/catalyst; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.poly.2018.06.053

upstream raw materials:

styrene

N-phenyl benzoyl amide

N-methyl-p-aminophenol

iodobenzene

Downstream raw materials:

2,5-bis(1-aziridinyl)-1,4-benzoquinone

2,5-bis-aziridin-1-yl-hydroquinone

2,5-bis-azetidin-1-yl-[1,4]benzoquinone

2,5-bis(2-methylaziridinyl)-1,4-benzoquinone

Refernces

• 1、 Marino,Schwartz. "-". . p. 812. Retrieved 1974.
• 2、 Forni, Luigi G.,Mora-Arellano, Victor O.,Packer, John E.,Willson, Robin L.. "Nitrogen Dioxide and Related Free Radicals: Electron-transfer Reactions with Organic Compounds in Solutions containing Nitrite or Nitrate". . p. 1 - 6. Retrieved 1986.
• 3、 Fu, Weiwei,Wang, Runwei,Wu, Lele,Wang, Hongbin,Wang, Xu,Wang, Aijing,Zhang, Zongtao,Qiu, Shilun. "Synthesis of Cu2 (OH)PO4 crystals with various morphologies and their catalytic activity in hydroxylation of phenol". . p. 772 - 774. Retrieved 2013.
• 4、 Zhang, Hong,Jiang, Yingyu,Zhou, Baiqin,Wei, Zhuo,Zhu, Zhenya,Han, Lijuan,Zhang, Ping,Hu, Yingying. "Preparation and photocatalytic performance of silver-modified and nitrogen-doped TiO2nanomaterials with oxygen vacancies". . p. 4694 - 4704. Retrieved 2021.
• 5、 Dulog,Vogt. "-". . p. 1915. Retrieved 1967.
• 6、 Panda, Abhina K.,Mahapatro, Surendra N.,Panigrahi, Ganesh P.. "Peroxomonophosphoric Acid Oxidation. 7. Studies of the Kinetics and Substituent Effect in the Oxidation of Aniline". . p. 4000 - 4004. Retrieved 1981.
• 7、 Saa, Jose M.,Llobera, Antonia,Deya, Pedro M.. "Fermy's Salt Promoted Oxidative Degradation of p-Hydroxybenzylamines and p-Hydroxybenzamides. A Novel Approach to p-Quinones". . p. 771 - 774. Retrieved 1987.
• 8、 Shi, Fengwei,Zheng, Jinlong,Xu, Kai,Zhang, Long,Hu, Jianglei. "Synthesis of binary Cu-Pd-alginates dry bead and its high catalytic activity for hydroxylation of phenol". . p. 23 - 26. Retrieved 2012.
• 9、 Cao, Xiangyu. "Kinetics of chlorine dioxide oxidation of benzidine in wastewater". . p. 493 - 496. Retrieved 2013.
• 10、 Michaelis,Granick. "-". . p. 1636,1642, 1643. Retrieved 1941.