2565-54-0

Basic information

• Product Name: (6Z)-6-[(butylamino)methylidene]cyclohexa-2,4-dien-1-one
• CAS NO: 2565-54-0
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• Mol File: 2565-54-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 300.3°C at 760 mmHg
• Flash Point: 121.2°C
• Density: 1.073g/cm³
• Vapor Pressure: 0.00113mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: (6Z)-6-[(butylamino)methylidene]cyclohexa-2,4-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6Z)-6-[(butylamino)methylidene]cyclohexa-2,4-dien-1-one(2565-54-0)
• EPA Substance Registry System: (6Z)-6-[(butylamino)methylidene]cyclohexa-2,4-dien-1-one(2565-54-0)

Safety Data

• Hazardous Substances Data: 2565-54-0(Hazardous Substances Data)

Usage

General Description

(6Z)-6-[(butylamino)methylidene]cyclohexa-2,4-dien-1-one is a chemical compound with the chemical formula C12H17NO. It is also known as N-butylidene-n-butylamine and is a yellow to brown liquid with a faint odor. (6Z)-6-[(butylamino)methylidene]cyclohexa-2,4-dien-1-one is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in organic synthesis as a building block to create more complex chemical structures. However, it is important to handle this compound with caution as it may be harmful if swallowed, inhaled or comes in contact with the skin.

Upstream product

• 90-02-8 salicylaldehyde 
• 109-73-9 N-butylamine 
• 54396-25-7 N-phenyl-2-oxochromene-3-carboxamide 
• 19028-72-9 N-(2-hydroxybenzylidene)cyclohexylamine 
• 1846-99-7 N-(3-methylphenyl)-2-oxo-2H-chromene-3-carboxamide 
• 74556-01-7 coumarin-3-carboxy-(4-bromo-3-methyl)-anilide 
• 74555-99-0 N-(4-bromophenyl)-2-oxo-2H-chromene-3-carboxamide 
• 779-84-0 N-phenylsalicylaldimine 

Downstream Products

• 32009-02-2 NbCl₅*HOC₆H₄CHNCH₂CH₂CH₂CH₃*CH₃CN 
• 16456-97-6 [zinc(II)bis(N-butylsalicylideneiminate)] 
• 62498-73-1 N-butyl-N-(2-hydroxybenzyl)amine 
• 19028-72-9 N-(2-hydroxybenzylidene)cyclohexylamine 
• 109-73-9 N-butylamine 
• 13986-33-9 [copper(II)bis(N-butylsalicylideneiminate)] 
• 82056-87-9 MoOCl₃(OHC₆H₄CHN(CH₂)3CH₃)2 

Relevant articles and documents

Syntheses, structures and catalytic properties of ruthenium(II) nitrosyl complexes with bidentate and tetradentate Schiff base ligands

Treatment of Ru(NO)Cl3·xH2O with 1 equiv. bidentate Schiff bases in the presence of triethylamine in DMF/THF afforded a series of anionic ruthenium(II) nitrosyl complexes of the type [Et3NH][Ru(κ2-N,O-LR)(NO)Cl3] (HLR = 2-butyliminomethyl-phenol 1, 2-(benzylimino-methyl)-phenol 2, 2-[(4-chloro-phenylimino)-methyl]-phenol 3, 2-[(4-nitro-phenylimino)-methyl]-phenol 4, 2-[(2,6-diisopropyl-phenylimino)-methyl]-phenol 5). Interaction of Ru(NO)Cl3·xH2O and 1 equiv. tetradentate Schiff bases under the same condition led to isolation of an anionic complex [Et3NH][Ru(κ2-N,O-L-CH2CH2-NOH)-(NO)Cl3] (HL-CH2CH2-NOH = N,N′-disalicylidene-1,2-ethanediamine 6) and a neutral complex [Ru(salen-phn)(NO)Cl] (H2salen-phn = N,N′-disalicylidene-1,2-phenyldiamine 7). The molecular structures of 1·?C2H5OH, 2–6, and 7·CH2Cl2 have been determined by single-crystal X-ray crystallography. Investigation of the catalytic properties of ruthenium(II) nitrosyl complexes 1–7 showed that they are efficient catalytic precursors for the transfer hydrogenation of acetophenone.

Anagostic, mono- and hexahapta interactions in Tl(I) dithiocarbamates: A new precursor for the preparation of Tl2S nanoparticles

Two new homoleptic complexes, [Tl(bzfdtc)]2 (1) and [Tl(bu2-OHbzdtc)]2 (2) (where bzfdtc = N-benzyl-N-furfuryldithiocarbamate and bu2-OHbzdtc = (N-butyl-N-(2-hydroxybenzyl)dithiocarbamate), have been prepared an

Chemical reactivity and skin sensitization potential for benzaldehydes: Can Schiff base formation explain everything?

Skin sensitizers chemically modify skin proteins rendering them immunogenic. Sensitizing chemicals have been divided into applicability domains according to their suspected reaction mechanism. The widely accepted Schiff base applicability domain covers aldehydes and ketones, and detailed structure-activity-modeling for this chemical group was presented. While Schiff base formation is the obvious reaction pathway for these chemicals, the in silico work was followed up by limited experimental work. It remains unclear whether hydrolytically labile Schiff bases can form sufficiently stable epitopes to trigger an immune response in the living organism with an excess of water being present. Here, we performed experimental studies on benzaldehydes of highly differing skin sensitization potential. Schiff base formation toward butylamine was evaluated in acetonitrile, and a detailed SAR study is presented. o-Hydroxybenzaldehydes such as salicylaldehyde and the oakmoss allergens atranol and chloratranol have a high propensity to form Schiff bases. The reactivity is highly reduced in p-hydroxy benzaldehydes such as the nonsensitizing vanillin with an intermediate reactivity for p-alkyl and p-methoxy-benzaldehydes. The work was followed up under more physiological conditions in the peptide reactivity assay with a lysine-containing heptapeptide. Under these conditions, Schiff base formation was only observable for the strong sensitizers atranol and chloratranol and for salicylaldehyde. Trapping experiments with NaBH3CN showed that Schiff base formation occurred under these conditions also for some less sensitizing aldehydes, but the reaction is not favored in the absence of in situ reduction. Surprisingly, the Schiff bases of some weaker sensitizers apparently may react further to form stable peptide adducts. These were identified as the amides between the lysine residues and the corresponding acids. Adduct formation was paralleled by oxidative deamination of the parent peptide at the lysine residue to form the peptide aldehyde. Our results explain the high sensitization potential of the oakmoss allergens by stable Schiff base formation and at the same time indicate a novel pathway for stable peptide-adduct formation and peptide modifications by aldehydes. The results thus may lead to a better understanding of the Schiff base applicability domain.