611-70-1

Basic information

• Product Name: Isobutyrophenone
• Synonyms: PHENYL ISOPROPYL KETONE;ALPHA-METHYLPROPIOPHENONE;2-METHYL-1-PHENYL-1-PROPANONE;ISOBUTYROPHENONE;ISOBUTYRYLBENZENE;ISOPROPYL PHENYL KETONE;1-Propanone, 2-methyl-1-phenyl-;1-Propanone,2-methyl-1-phenyl-
• CAS NO: 611-70-1
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.2
• EINECS: 210-275-0
• Mol File: 611-70-1.mol
• Article Data: 330

Chemical Properties

• Melting Point: 1 °C
• Boiling Point: 217 °C(lit.)
• Flash Point: 184 °F
• Appearance: clear colorless to very slightly yellow liquid
• Density: 0.988 g/mL at 25 °C(lit.)
• Vapor Pressure: 1 mm Hg ( 50 °C)
• Refractive Index: n20/D 1.517(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility: immiscible
• BRN: 774499
• CAS DataBase Reference: Isobutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutyrophenone(611-70-1)
• EPA Substance Registry System: Isobutyrophenone(611-70-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 611-70-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to very slightly yellow liquid

Uses

Isobutyrophenone is used as an internal standard in the determination of hydroxyzine hydrochloride and benzyl alcohol in injection solutions. It is also used in the preparation of alpha-hydroxyisobutyrophenone. Isobutyrophenone is employed as photosensitizer intermediate. It can react with bromoacetic acid ethyl ester to get 3-hydroxy-4-methyl-3-phenyl-valeric acid ethyl ester.

Preparation

Isobutyrophenone synthesis: Benzene underwent a Friedel–Crafts acylation with isobutyryl chloride to synthesize isobutyrophenone. The reaction was performed using excess benzene as a replacement for a typical solvent and heat to reflux (88 °C) for a period of 3 hours. Any unreacted benzene was recovered after the reaction during the distillation process. A 66 % yield of isobutyrophenone was obtained from the solar synthesis, compared to a 44 % yield from an in-lab, electrical heating analysis.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1061, 1949 DOI: 10.1021/ja01171a084The Journal of Organic Chemistry, 32, p. 404, 1967 DOI: 10.1021/jo01288a032Tetrahedron Letters, 14, p. 2491, 1973

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H12O/c1-8(2)10(11)9-6-4-3-5-7-9/h3-8H,1-2H3

Upstream product

• 33950-46-8 1-phenyl-2,2-dimethyl-1,3-propanediol 
• 79-30-1 isobutyryl chloride 
• 71-43-2 benzene 
• 463-49-0 1,2-propanediene 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 39158-85-5 2-methyl-1-phenyl-1-trimethylsiloxy-1-propene 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 124326-38-1 isobutyrophenone enolate 
• 920-39-8 isopropylmagnesium bromide 
• 185245-65-2 3-methylthio-3-N-piperidino-1-phenyl-2-propen-1-one 
• 106367-32-2 [3-Chloro-2,2-dimethyl-1-phenyl-prop-(E)-ylidene]-isopropyl-amine 
• 97119-10-3 2-methyl-N-propionylpropionamide 
• 591-51-5 phenyllithium 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 2762-71-2 2-methyl-1-phenyl-1-(pyridin-2-yl)propan-1-ol 
• 6668-27-5 2-methyl-1-phenyl-propylamine 
• 21297-90-5 3-carbethoxy-2-(1-methylethyl)-2-phenyloxirane 
• 35929-19-2 2,2-Dimethyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-one 
• 7721-20-2 α-Pyrrolidino-β,β-dimethyl styrene 
• 53344-40-4 1-(4-morpholinyl)-1-phenyl-2-methylpropene 
• 107402-07-3 N-(3,3-Dimethyl-4-oxo-4-phenyl-butyl)-benzamide 
• 126256-10-8 2-Methyl-1-phenyl-1-(9-xanthyl)-1-propanol 
• 93291-99-7 3-cyclohexyl-3-hydroxy-2,2-dimethyl-1-phenyl-1-propanone 
• 76963-04-7 3-(4-methoxyphenyl)-2,2-dimethyl-1-phenylpropan-1-one 
• 113493-79-1 3-Hydroxy-2,2-dimethyl-3-(4-nitro-phenyl)-1-phenyl-propan-1-one 
• 75990-52-2 3-hydroxy-2,2-dimethyl-1,3-diphenylpropan-1-one 
• 13031-08-8 4-phenylpivalophenone 
• 96863-70-6 3-Hydroxy-3-(4-methoxy-phenyl)-2,2-dimethyl-1-phenyl-propan-1-one 

Relevant articles and documents

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Kinetics of Ketonization of Isobutyrophenone Enol in Aqueous Solution. Broensted Relations and Analysis of Data by Marcus and Lewis-More O'Ferrall Rate Theories

The enol isomer of isobutyrophenone was generated in aqueous solution from its alkali-metal enolates, and rates of ketonization of the enol in this solvent were measured under catalysis by HCl, NaOH, H3PO4, H2PO4(1-), six carboxylic acids (RCO2H), and six

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