136295-53-9

Basic information

• Product Name: 4-(3-OXO-PROPYL)-BENZONITRILE
• Synonyms: 4-(3-OXO-PROPYL)-BENZONITRILE;Benzonitrile, 4-(3-oxopropyl)-
• CAS NO: 136295-53-9
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18456
• Mol File: 136295-53-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 290.3°C at 760 mmHg
• Flash Point: 129.4°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.00209mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: 4-(3-OXO-PROPYL)-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-OXO-PROPYL)-BENZONITRILE(136295-53-9)
• EPA Substance Registry System: 4-(3-OXO-PROPYL)-BENZONITRILE(136295-53-9)

Safety Data

• Hazardous Substances Data: 136295-53-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H9NO/c11-8-10-5-3-9(4-6-10)2-1-7-12/h3-7H,1-2H2

Upstream product

• 20461-86-3 2,2-diethoxy acetic acid 
• 3435-51-6 4-ethenylbenzonitrile 
• 123-38-6 propionaldehyde 
• 100-47-0 benzonitrile 
• 201230-82-2 carbon monoxide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 107-18-6 allyl alcohol 
• 83101-12-6 4-(3-Hydroxypropyl)benzonitrile 
• 41917-85-5 p-cyanocinnamaldehyde 
• 3058-39-7 4-iodobenzonitrile 

Downstream Products

• 41917-85-5 p-cyanocinnamaldehyde 
• 62584-73-0 4-(3-(4-methoxyphenyl)-3-oxopropyl)benzonitrile 
• 95759-33-4 4-cyanocinnamaldehyde 
• 934622-24-9 diphenyl 1-(N-(benzyloxycarbonyl)amino)-1-(4-cyanophenyl)propanephosphonate 

Relevant articles and documents

VISIBLE-LIGHT MEDIATED ORGANOPHOTOREDOX CATALYTIC DEUTERATION OF AROMATIC AND ALIPHATIC ALDEHYDES

Described are methods for preparing a deuterated aldehyde using with a photocatalyst and a hydrogen atom transfer agent in a H2O free solvent comprising D2O and an organic solvent under an inert gas. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions.

Iron Catalyzed Hydroformylation of Alkenes under Mild Conditions: Evidence of an Fe(II) Catalyzed Process

Earth abundant, first row transition metals offer a cheap and sustainable alternative to the rare and precious metals. However, utilization of first row metals in catalysis requires harsh reaction conditions, suffers from limited activity, and fails to tolerate functional groups. Reported here is a highly efficient iron catalyzed hydroformylation of alkenes under mild conditions. This protocol operates at 10-30 bar syngas pressure below 100 °C, utilizes readily available ligands, and applies to an array of olefins. Thus, the iron precursor [HFe(CO)4]-[Ph3PNPPh3]+ (1) in the presence of triphenyl phosphine catalyzes the hydroformylation of 1-hexene (S2), 1-octene (S1), 1-decene (S3), 1-dodecene (S4), 1-octadecene (S5), trimethoxy(vinyl)silane (S6), trimethyl(vinyl)silane (S7), cardanol (S8), 2,3-dihydrofuran (S9), allyl malonic acid (S10), styrene (S11), 4-methylstyrene (S12), 4-iBu-styrene (S13), 4-tBu-styrene (S14), 4-methoxy styrene (S15), 4-acetoxy styrene (S16), 4-bromo styrene (S17), 4-chloro styrene (S18), 4-vinylbenzonitrile (S19), 4-vinylbenzoic acid (S20), and allyl benzene (S21) to corresponding aldehydes in good to excellent yields. Both electron donating and electron withdrawing substituents could be tolerated and excellent conversions were obtained for S11-S20. Remarkably, the addition of 1 mol % acetic acid promotes the reaction to completion within 16-24 h. Detailed mechanistic investigations revealed in situ formation of an iron-dihydride complex [H2Fe(CO)2(PPh3)2] (A) as an active catalytic species. This finding was further supported by cyclic voltammetry investigations and intermediacy of an Fe(0)-Fe(II) species was established. Combined experimental and computational investigations support the existence of an iron-dihydride as the catalyst resting state, which then follows a Fe(II) based catalytic cycle to produce aldehyde.

Photoredox activation for the direct β-arylation of ketones and aldehydes

The direct β-activation of saturated aldehydes and ketones has long been an elusive transformation. We found that photoredox catalysis in combination with organocatalysis can lead to the transient generation of 5π-electron β-enaminyl radicals from ketones and aldehydes that rapidly couple with cyano-substituted aryl rings at the carbonyl β-position. This mode of activation is suitable for a broad range of carbonyl β-functionalization reactions and is amenable to enantioselective catalysis.