13988-65-3

Basic information

• Product Name: 1,3-Pentanedione, 4-methyl-1-phenyl-
• Synonyms: 1,3-Pentanedione,4-methyl-1-phenyl;4-methyl-1-phenyl-1,3-pentadione;4-ISOBUTYRYLACETOPHENONE;4-Methyl-1-phenyl-pentan-1,3-dion;4-methyl-1-phenyl-pentane-1,3-dione;11.13-Dioxo-1-(14-metho-pentyl)-benzol;4-methyl-1-phenyl-1,3-pentanedione
• CAS NO: 13988-65-3
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol File: 13988-65-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 121-122 °C(Press: 5 Torr)
• Density: 1.031±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,3-Pentanedione, 4-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Pentanedione, 4-methyl-1-phenyl-(13988-65-3)
• EPA Substance Registry System: 1,3-Pentanedione, 4-methyl-1-phenyl-(13988-65-3)

Safety Data

• Hazardous Substances Data: 13988-65-3(Hazardous Substances Data)

Usage

Chemical Class

Ketone

Structure

Five-carbon chain with two ketone groups, a methyl group, and a phenyl group attached to the third carbon atom

Common Uses

a. Production of fragrances and flavorings
b. Synthesis of pharmaceuticals
c. Other industrial applications

Health Hazards

a. Linked to respiratory issues
b. Considered a respiratory irritant

Precautions

Careful consideration of potential health risks when handling and using the compound

Upstream product

• 3815-34-7 2,2-dimethyl-1-phenyl-1,3-butanedione 
• 98-86-2 acetophenone 
• 97-62-1 Ethyl isobutyrate 
• 563-80-4 3-methyl-butan-2-one 
• 93-99-2 benzoic acid phenyl ester 
• 5738-30-7 (2-phenyl-[1,3]dioxolan-2-yl)-acetonitrile 
• 920-39-8 isopropylmagnesium bromide 
• 60143-75-1 Benzoyl-isobutyryl-methan (Enolform); 1-Phenyl-4-methyl-1-hydroxy-3-oxo-penten-⁽¹⁾ 
• 98-88-4 benzoyl chloride 
• 84034-01-5 trans-2,3-epoxy-3-(2-propanyl)-1-phenyl-1-propanone 
• 1523-69-9 diethyl isobutyryl phosphonate 
• 60-29-7 diethyl ether 
• 79-30-1 isobutyryl chloride 
• 1204698-66-7 C₁₄H₁₆O₃ 

Downstream Products

• 60143-75-1 Benzoyl-isobutyryl-methan (Enolform); 1-Phenyl-4-methyl-1-hydroxy-3-oxo-penten-⁽¹⁾ 
• 20716-14-7 4-methyl-3-(4-nitro-benzoyloxy)-1-phenyl-pent-2-enone 
• 95766-51-1 5⁽³⁾-isopropyl-3⁽⁵⁾-phenylpyrazole 
• 61666-08-8 2-allyl-4-methyl-1-phenyl-1,3-pentanedione 
• 82145-67-3 2-ethyl-4-methyl-1-phenyl-1,3-pentanedione 
• 1048948-24-8 4-methyl-1-phenyl-3-(phenylamino)pent-2-en-1-one 
• 1176887-93-6 (Z)-1-amino-4-methyl-1-phenylpent-1-en-3-one 
• 1176887-92-5 (Z)-3-amino-4-methyl-1-phenylpent-2-en-1-one 
• 1361387-50-9 (E)-1-(methoxyimino)-4-methyl-1-phenylpentan-3-one 
• 1361387-76-9 (1Z)-2-diazo-1-(methoxyimino)-4-methyl-1-phenvIpentan-3-one 

Relevant articles and documents

-

-

I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives

An I2-promoted strategy has been developed for the synthesis of thiazol-2(3H)-one derivatives from 1,3-diketones with potassium thiocyanate. This [3+2] cyclization reaction involves C?S and C?N bond formation and exhibits good functional group tolerance. A series of thiazol-2(3H)-one derivatives are obtained in moderate to good yields. (Figure presented.).

Synthesis of 1,3-Diketones and β-Keto Thioesters via Soft Enolization

Ketones and thioesters undergo soft enolization and acylation using crude acid chlorides on treatment with MgBr2·OEt2 and i-Pr2NEt to give 1,3-diketones and β-keto thioesters, respectively. The use of crude acid chlorides adds efficiency and cost reduction by avoiding the need to purify and/or purchase them. The process is conducted in a direct fashion that does not require prior enolate formation, further enhancing its efficiency and making it very easy to carry out. The method is suitable for large scale applications. ?

1,4-Addition of Bis(iodozincio)methane to α,β-Unsaturated ketones: Chemical and theoretical/computational studies

1,4-Addition of bis(iodozincio)methane to simple α,β-unsaturated ketones does not proceed well; the reaction is slightly endothermic according to DFT calculations. In the presence of chlorotrimethylsilane, the reaction proceeded efficiently to afford a silyl enol ether of β-zinciomethyl ketone. The CZn bond of the silyl enol ether could be used in a cross-coupling reaction to form another C-C bond in a one-pot reaction. In contrast, 1,4-addition of the dizinc reagent to enones carrying an acyloxy group proceeded very efficiently without any additive. In this case, the product was a 1,3-diketone, which was generated in a novel tandem reaction. A theoretical/computational study indicates that the whole reaction pathway is exothermic, and that two zinc atoms of bis(iodozincio)methane accelerate each step cooperatively as effective Lewis acids.