1,4-Diacetylbenzene

Base Information

• Chemical Name: 1,4-Diacetylbenzene
• CAS No.: 1009-61-6
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 29143990
• European Community (EC) Number: 213-769-4
• NSC Number: 295548
• UNII: WM5GGF7BQ6
• DSSTox Substance ID: DTXSID7021657
• Nikkaji Number: J13.525I
• Wikidata: Q63399973
• ChEMBL ID: CHEMBL3186189
• Mol file: 1009-61-6.mol

Synonyms:Benzene,p-diacetyl- (6CI,8CI);4'-Acetylacetophenone;NSC 295548;p-Acetylacetophenone;p-Diacetylbenzene;

Chemical Property of 1,4-Diacetylbenzene

Chemical Property:

• Appearance/Colour: almost white to light brown crystalline powder
• Vapor Pressure: 0.00115mmHg at 25°C
• Melting Point: 111-113 °C(lit.)
• Refractive Index: 1.519
• Boiling Point: 300.068 °C at 760 mmHg
• Flash Point: 112.06 °C
• PSA: 34.14000
• Density: 1.064 g/cm³
• LogP: 2.09180
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 6.309mg/L(25 oC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

1,1''-(1,4-phenylene)bis-Ethanone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC(=O)C1=CC=C(C=C1)C(=O)C
• Uses: 1,1''-(1,4-phenylene)bis-Ethanone can undergo oxidative C-C Bond Cleavage to synthesize an aryl carboxylic acid with an iodine catalyst . 1,1''-(1,4-phenylene)bis-Ethanone is also capable of Suzuki-Miyaura coupling.

Technology Process of 1,4-Diacetylbenzene

There total 108 articles about 1,4-Diacetylbenzene 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: 99.0%

4-ethynylacetophenone (42472-69-5) → 1,4-Diacetylbenzene (1009-61-6)

Guidance literature:

With trifluorormethanesulfonic acid; silver trifluoromethanesulfonate; C₇₅H₅₂AuClN₂O₂; In methanol; dichloromethane; water; at 20 ℃; for 20h;

DOI:10.1002/adsc.201800605

Reference yield: 96.0%

1,4-diethynylbenzene (935-14-8) → 1,4-Diacetylbenzene (1009-61-6)

Guidance literature:

With trifluorormethanesulfonic acid; water; In 2,2,2-trifluoroethanol; at 25 ℃; for 45h; regioselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.6b00801

Reference yield: 96.0%

1-ethenyl-2-pyrrolidinone (88-12-0) + 4-acetylphenylboronic acid (149104-90-5) → 1,4-Diacetylbenzene (1009-61-6)

Guidance literature:

1-ethenyl-2-pyrrolidinone; 4-acetylphenylboronic acid; With 2.9-dimethyl-1,10-phenanthroline; p-benzoquinone; palladium diacetate; In acetonitrile; at 100 ℃; for 0.166667h; microwave irradiation;

With silica gel; In ethyl acetate; Further stages.;

DOI:10.1021/jo701434s

upstream raw materials:

terephthalonitrile

methyl magnesium iodide

diethyl ether

1,4-diethylbenzene

Downstream raw materials:

1,4-bis-(5t-phenyl-penta-2t,4-dienoyl)-benzene

1,4-benzenedicarboxylic acid dimethyl ester

1,4-bis-(1-hydroxy-1-methyl-pentyl)-benzene

1,4-bis-(2-chloro-cinnamoyl)-benzene

Refernces

• 1、 Fillon, Hyacinthe,Le Gall, Erwan,Gosmini, Corinne,Périchon, Jacques. "Pure acetonitrile as solvent for the efficient electrochemical conversion of aryl bromides in organozinc species and their coupling reaction with acetyl chloride". . p. 5941 - 5944. Retrieved 2002.
• 2、 Tan, Jiajing,Zheng, Tianyu,Yu, Yuqi,Xu, Kun. "TBHP-promoted direct oxidation reaction of benzylic Csp3-H bonds to ketones". . p. 15176 - 15180. Retrieved 2017.
• 3、 Zhou, Ying,Long, Jilan,Li, Yingwei. "Ni-based catalysts derived from a metal-organic framework for selective oxidation of alkanes". . p. 955 - 962. Retrieved 2016.
• 4、 Xie, Ya,Wang, Jingjing,Wang, Yunyun,Han, Sheng,Yu, Han. "Hydration of Alkynes to Ketones with an Efficient and Practical Polyoxomolybdate-based Cobalt Catalyst". . p. 4985 - 4989. Retrieved 2021/10/12.
• 5、 García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa. "Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis". supporting information. p. 3392 - 3399. Retrieved 2021/05/21.