1009-61-6

Basic information

• Product Name: 1,4-DIACETYLBENZENE
• Synonyms: 1-(4-Acetyl-phenyl)-ethanone;1,1’-(1,4-phenylene)bis-ethanon;Benzene, p-diacetyl-;P-ACETYL ACETOPHENONE;P-DIACETYLBENZENE;TIMTEC-BB SBB008588;1,4-DIACETYLBENZENE;4'-ACETYLACETOPHENONE
• CAS NO: 1009-61-6
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 213-769-4
• Product Categories: Aromatic Ketones (substituted);C10;Carbonyl Compounds;Ketones
• Mol File: 1009-61-6.mol
• Article Data: 106

Chemical Properties

• Melting Point: 111-113 °C(lit.)
• Boiling Point: 120 °C / 1mmHg
• Flash Point: 112.06 °C
• Appearance: almost white to light brown crystalline powder
• Density: 1.0613 (rough estimate)
• Vapor Pressure: 0.00115mmHg at 25°C
• Refractive Index: 1.5120 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 6.309mg/L(25 oC)
• BRN: 1907515
• CAS DataBase Reference: 1,4-DIACETYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIACETYLBENZENE(1009-61-6)
• EPA Substance Registry System: 1,4-DIACETYLBENZENE(1009-61-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1009-61-6(Hazardous Substances Data)

Usage

Chemical Properties

ALMOST WHITE TO LIGHT BROWN CRYSTALLINE POWDER

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4308, 1961 DOI: 10.1021/jo01069a031Synthetic Communications, 26, p. 3175, 1996 DOI: 10.1080/00397919608004626

Purification Methods

Crystallise it from EtOH (m 114o) or *benzene and dry it in a vacuum over CaCl2. Also purify it by dissolving it in acetone, treating with Norit, evaporating and recrystallising from MeOH. The dioxime has m 248-259o. [Wagner et al. J Am Chem Soc 108 7727 1986]. [Beilstein 7 H 686, 7 II 624, 7 III 3504, 7 IV 2156.]

InChI:InChI=1/C10H10O2/c1-7(11)9-3-5-10(6-4-9)8(2)12/h3-6H,1-2H3

Upstream product

• 937-30-4 4-ethylacetophenone 
• 109-65-9 1-bromo-butane 
• 35768-36-6 1,4-diacetyl-cyclohexa-1,4-diene 
• 111-34-2 -butyl vinyl ether 
• 99-90-1 para-bromoacetophenone 
• 78-76-2 s-butyl bromide 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 141-78-6 ethyl acetate 
• 624-38-4 para-diiodobenzene 
• 75-36-5 acetyl chloride 
• 18090-43-2 3,6-bis(trimethylsilyl)cyclohexane-1,4-diene 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 100-20-9 terephthaloyl chloride 
• 594-27-4 tetramethylstannane 

Downstream Products

• 34838-67-0 1,4-bis-(3t-[2]furyl-acryloyl)-benzene 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 636-09-9 diethyl terephthalate 
• 221910-24-3 1-(4-(quinolin-2-yl)phenyl)ethan-1-one 
• 2176-75-2 2,2'-p-phenylene-bis-quinoline 
• 2948-46-1 α,α,α',α'-tetramethyl-1,4-benzenedimethanol 
• 101447-97-6 1,4-bis-(1-hydroxy-1-methyl-butyl)-benzene 
• 106596-70-7 1,4-bis-(1-hydroxy-1-methyl-allyl)-benzene 
• 2790-71-8 1,4-bis(trichloroacetyl)benzene 
• 2673-16-7 1,4-dioxoacetyl-benzene 
• 140-50-1 N,N'-diacetyl-1,4-phenylenediamine 
• 1905-26-6 1,4-bis-chloroacetyl-benzene 
• 100117-38-2 1-[4-(1-acetoxy-ethyl)-phenyl]-ethanone 
• 681462-41-9 1,4-diacetyl-2-nitro-benzene 

Relevant articles and documents

Development of a Flow Photochemical Aerobic Oxidation of Benzylic C-H Bonds

A continuous mesofluidic process has been developed for benzylic C-H oxidation with moderate to good yields using a photocatalyst (riboflavin tetraacetate, RFT) activated by a UV lamp and an iron additive [Fe(ClO4)2] via incorporation of singlet oxygen (1O2) for the direct formation of oxidized C=O or CH-OH compounds.

Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids

Arylations of electron-rich heteroatom-substituted olefins were performed with arylboronic acids. This appears to constitute the first example of palladium(II)-catalyzed internal Heck arylations. The novel protocol exploits oxygen gas for environmentally benign reoxidation and a stable 1,10-phenanthroline bidentate ligand to promote the palladium(II) regeneration and to control the regioselectivity. Internal arylation is strongly favored with electron-rich arylboronic acids. DFT calculations support a charge-driven selectivity rationale, where phenyls substituted with electron-donating groups prefer the electron-poor α-carbon of the olefin. Experiments, verified by calculations, confirm the cationic nature of the catalytic route. This Heck methodology provides a facile and mild access to functionalized enamides. Controlled microwave heating and increased oxygen pressure were used to further reduce the reaction time to 1 h.

Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride

Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]