959-28-4

Basic information

• Product Name: TRANS-1,2-DIBENZOYLETHYLENE
• Synonyms: TIMTEC-BB SBB007664;TRANS-DIPHENACYLIDENE;TRANS-1,2-DIBENZOYLETHYLENE;TRANS-1,4-DIPHENYL-2-BUTENE-1,4-DIONE;(2E)-1,4-Diphenyl-2-butene-1,4-dione;2-Butene-1,4-dione, 1,4-diphenyl-, (E)-;4-diphenyl-4-dion(e)-2-butene-1;1,2-DIBENZOYLETHYLENE
• CAS NO: 959-28-4
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.27
• EINECS: 213-498-1
• Product Categories: Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 959-28-4.mol
• Article Data: 47

Chemical Properties

• Melting Point: 109-112 °C(lit.)
• Boiling Point: 338.73°C (rough estimate)
• Flash Point: 138.2 °C
• Appearance: White to yellow to beige-brown/Powder, Crystals or Flakes
• Density: 1.1223 (rough estimate)
• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• BRN: 743958
• CAS DataBase Reference: TRANS-1,2-DIBENZOYLETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1,2-DIBENZOYLETHYLENE(959-28-4)
• EPA Substance Registry System: TRANS-1,2-DIBENZOYLETHYLENE(959-28-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: EM7000000
• TSCA: Yes
• Hazardous Substances Data: 959-28-4(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

(E)-1,4-Diphenylbut-2-ene-1,4-dione is a key intermediate for the Michael adducts-source for biologically potent heterocycles with antimicrobial properties.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 360, 1990 DOI: 10.1021/jo00288a066Journal of the American Chemical Society, 45, p. 1303, 1923 DOI: 10.1021/ja01658a026

Purification Methods

It crystallises from MeOH or EtOH as yellow needles [Koller et al. Helv Chim Acta 29 512 1946]. The dioxime has m 210-211o(dec) from AcOH. [IR: Kuhn et al. J Am Chem Soc 72 5058 1950, Yates J Am Chem Soc 74 5375 1952, Erickson et al. J Am Chem Soc 73 5301 1951, Beilstein 7 IV 2578.]

InChI:InChI=1/C16H12O2/c17-15(13-7-3-1-4-8-13)11-12-16(18)14-9-5-2-6-10-14/h1-12H/b12-11+

Upstream product

• 959-27-3 (Z)-1,4-diphenylbut-2-ene-1,4-dione 
• 65218-88-4 (+)-(R)-o-methoxyphenylphenyl free sulfimide 
• 32147-16-3 meso-2,3-dibromo-1,4-diphenyl-1,4-butanedione 
• 955-83-9 2,5-diphenylfuran 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 91-22-5 quinoline 
• 108-24-7 acetic anhydride 
• 60-29-7 diethyl ether 
• 7664-41-7 ammonia 
• 70-11-1 α-bromoacetophenone 
• 7647-01-0 hydrogenchloride 
• 7446-08-4 selenium(IV) oxide 
• 64-17-5 ethanol 

Downstream Products

• 860549-74-2 9,10-dibenzoyl-1,2,3,4,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene 
• 857580-26-8 2,3-dibenzoyl-benz[de]anthracen-7-one 
• 975-70-2 trans dibenzoyl-4,5 dimethyl-1,2 cyclohexene 
• 2461-81-6 3-benzoyl-1,5-diphenyl-pentane-1,5-dione 
• 29235-05-0 2-methoxy-1,4-diphenyl-1,4-butanedione 
• 13249-75-7 (Z)-1,2,4-triphenyl-2-butene-1,4-dione 
• 102553-32-2 2-butylsulfanyl-1,4-diphenyl-butane-1,4-dione 
• 102447-45-0 2-pentylsulfanyl-1,4-diphenyl-butane-1,4-dione 
• 15441-15-3 3-benzoyl-1,5-diphenyl-pent-2-ene-1,5-dione 
• 34086-34-5 (+/-)-trans-11,12-dibenzoyl-9,10-dihydro-9,10-ethano-anthracene 
• 103045-98-3 2-(1-methyl-2-phenyl-ethylsulfanyl)-1,4-diphenyl-butane-1,4-dione 
• 854395-09-8 3,4-dibenzoyl-1,2,2a,3,4,4a,5,6-octahydro-dibenzo[c,g]phenanthrene 
• 26463-62-7 1,4-diphenyl-2-(p-tolylamino)but-2-ene-1,4-dione 
• 72709-59-2 diethyl 2-(1,2-dibenzoylethyl)propanedioate 

Relevant articles and documents

A Novel Synthesis of 4-Dioxy-2-enones from 1,3-Dienes using Pyridinium Dichromate-tert-Butyl Hydroperoxide

Treatment of 1,3-dienes with the pyridinium dichromate (PDC)-t-BuOOH reagent system leads directly to the formation of 4-tert-butyldioxy-2-enones in good yield under mild reaction conditions.

Stereoselective Synthesis of cis-2-Ene-1,4-diones via Aerobic Oxidation of Substituted Furans Catalyzed by ABNO/HNO3

We report a highly efficient and selective catalytic system, ABNO (9-azabicyclo-[3.3.1]nonane N-oxyl)/HNO3, for the aerobic oxidation of substituted furans to cis-2-ene-1,4-diones under mild reaction conditions using oxygen as the oxidant. The catalyst system is amenable to various substituted (mon-, di-, and tri-) furans and tolerates diverse functional groups, including cyano, nitro, naphthyl, ketone, ester, heterocycle, and even formyl groups. Based on the control and 18O-labeling experiments, the possible mechanism of the oxidation is proposed.

Diastereoselective sp3-C–H Functionalization of Arylmethyl Ketones and Transformation of E- to Z-Products Through Photocatalysis

We have developed an efficient metal-free route for the synthesis of 1,4-enedione derivatives under microwave irradiation by reacting easily available arylmethylketones with DMSO or diphenyl sulfoxide in the presence of TBAI and persulfate. The reaction is very clean and completes within very short time. All the reagents and catalysts are cheap and environmentally benign. In addition, the E-isomer of the products can easily be transformed into the Z-isomer by using eosin Y photocatalyst under the irradiation of white CFL.