5729-47-5

Basic information

• Product Name: acetylacrolein
• Synonyms: acetylacrolein;4-OXO-2-PENTENAL;2-Pentene-1,4-dione
• CAS NO: 5729-47-5
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.11
• Mol File: 5729-47-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 199.5°C at 760 mmHg
• Flash Point: 70.5°C
• Appearance: /
• Density: 0.989g/cm³
• Vapor Pressure: 0.341mmHg at 25°C
• Refractive Index: 1.427
• CAS DataBase Reference: acetylacrolein(CAS DataBase Reference)
• NIST Chemistry Reference: acetylacrolein(5729-47-5)
• EPA Substance Registry System: acetylacrolein(5729-47-5)

Safety Data

• Hazardous Substances Data: 5729-47-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H6O2/c1-5(7)3-2-4-6/h2-4H,1H3/b3-2+

Upstream product

• 94145-20-7 ammonium salt of 2,6-dihydroxy-3-(β-hydroxyethyl)-4-methyl-5-cyanopyridine 
• 100-46-9 benzylamine 
• 534-22-5 2-methylfuran 
• 111957-98-3 Pent-4-en-2-ol 

Downstream Products

• 1632-76-4 3-methylpyridazine 

Relevant articles and documents

Synthetic approaches to phomactins: Novel oxidation of homoallylic alcohols using tetra-n-propylammonium perruthenate

Previous studies of a synthesis of phomactin A had resulted in the synthesis of a 15-methylenebicyclo[9.3.1]pentadecadiene. The next step in the synthesis was to be the epoxidation of this methylenecyclohexane that was hoped would lead to a 1-(hydroxymethyl)cyclohexene by rearrangement of the exocyclic epoxide, but the epoxidation was difficult to carry out regioselectively on advanced intermediates. However, oxidation of a 15-methylenebicyclo[9.3.1]pentadeca-3,7-dien-14-ol using tetra-n-propylammonium perruthenate and N-methylmorpholine-N-oxide led to conversion of this homoallylic alcohol into the corresponding 14-oxobicyclo[9.3.1]pentadeca-1(15),3,7-triene-15-carboxaldehyde in one step. Reduction of this using DIBAL-H gave a promising intermediate for a synthesis of a phomactin. The scope of this oxidation of homoallylic alcohols was briefly investigated.

DERIVATIVES OF AZYINDOLES. 65. SYNTHESIS OF 1-BENZYL-4-METHYL-5-CYANO-6-HYDROXY-7-AZAINDOLINE

Treatment of the ammonium (I) or benzylammonium salt of 2,6-dihydroxy-3-(β-hydroxyethyl)-4-methyl-5-cyanopyridine (II) with a mixture of benzylamine and phosphorus pentoxide yielded 2-benzylamino-3-(β-hydroxyethyl)-4-methyl-5-cyano -6-hydroxypyridine (III), which, when heated with phosphorus oxychloride, is converted to 1-benzyl-4-methyl-5-cyano-6-hydroxy-7-azaindoline (IV).The products of thermal fragmentation of II with benzylamine were studied by the method of chromato-mass spectrometry.In addition to compound III, N,N'-dibenzylurea (V) and the dibenzylamide of malonic acid (VI) were preparatively isolated from the reaction products .The cyclization of I and II to 4-methyl-6-hydroxy-2,3-dihydro-7-azabenzofuran (VII) and 4-methyl-5-cyano-6-hydroxy-2,3-dihydro-7-azabenzofuran (VIII) was carried out.Heating VIII with benzylamine at 200-210 grad C led to compound III.