53179-04-7

Basic information

• Product Name: undec-10-enonitrile
• Synonyms: undec-10-enonitrile;10-Undecenenitrile;Undeca-10-enenitrile;Einecs 258-413-9
• CAS NO: 53179-04-7
• Molecular Formula: C₁₁H₁₉N
• Molecular Weight: 165.27526
• EINECS: 258-413-9
• Mol File: 53179-04-7.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: undec-10-enonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: undec-10-enonitrile(53179-04-7)
• EPA Substance Registry System: undec-10-enonitrile(53179-04-7)

Safety Data

• Hazardous Substances Data: 53179-04-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H19N/c1-2-3-4-5-6-7-8-9-10-11-12/h2H,1,3-10H2

Upstream product

• 151-50-8 potassium cyanide 
• 66605-77-4 9-decenyl p-toluenesulfonate 
• 57691-18-6 12-Cyano-2-dodecanon 
• 203940-73-2 12-bromo-2-dodecanone 
• 112-45-8 10-Undecenal 
• 62595-52-2 undec-10-en-1-amine 
• 88124-95-2 2-(undec-10-en-1-yl)isoindoline-1,3-dione 
• 161270-70-8 2-(10-hydroxydecyl)-1H-isoindole-1,3(2H)-dione 
• 56401-31-1 10-hydroxydecyl 4-methylbenzenesulfonate 
• 112-47-0 1,10-Decanediol 
• 13019-22-2 9-Decen-1-ol 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 82223-50-5 dodec-11-en-1-amine 
• 112-38-9 10-undecenoic acid 

Downstream Products

• 693-57-2 12-Aminododecanoic acid 
• 5810-18-4 11-cyanoundecanoic acid 
• 2244-07-7 undecanenitrile 
• 13050-14-1 12-oxododecanenitrile 
• 131379-24-3 Undec-9-enenitrile 
• 131379-24-3 (Z)-Undec-9-enenitrile 
• 131379-26-5 (E)-Undec-9-enenitrile 
• 74196-02-4 C₁₂H₂₁NO 
• 22915-49-7 11-cyanoundecanoic acid methyl ester 
• 53005-24-6 methyl 12-aminododecanoate 
• 117582-39-5 4-(10-cyanodecanyl)-acetophenone 
• 117582-48-6 3-(10-Cyanodecanyl)-5,5-dimethyl-2-cyclohexenone 
• 135508-11-1 (E)-12-Oxo-14-phenyl-13-tetradecenonitrile 

Relevant articles and documents

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

Triphenylbismuth Dichloride-Mediated Conversion of Thioamides to Nitriles

Thioamides were efficiently converted to nitriles using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process was also successfully extended to the synthesis of cyanamides starting from the corresponding thioureas and of thiocyanates from dithiocarbamates.