91-65-6

Basic information

• Product Name: N,N-DIETHYLCYCLOHEXYLAMINE
• Synonyms: Cyclohexylamine, N,N-diethyl-;Cyclohexyldiethylamine;Diethylcyclohexylamine;n,n-diethyl-cyclohexanamin;N,N-Diethylcyclohexanamine;n,n-diethyl-cyclohexylamin;(DIETHYLAMINO)CYCLOHEXANE;DECHA
• CAS NO: 91-65-6
• Molecular Formula: C₁₀H₂₁N
• Molecular Weight: 155.28
• EINECS: 202-087-2
• Mol File: 91-65-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 193 °C
• Flash Point: 57°C
• Appearance: /
• Density: 0,84 g/cm3
• Vapor Pressure: 0.351mmHg at 25°C
• Refractive Index: n20/D 1.4562(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.69±0.20(Predicted)
• CAS DataBase Reference: N,N-DIETHYLCYCLOHEXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHYLCYCLOHEXYLAMINE(91-65-6)
• EPA Substance Registry System: N,N-DIETHYLCYCLOHEXYLAMINE(91-65-6)

Safety Data

• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-36/37/39-45-27-16
• RIDADR: 2734
• RTECS: GU5830125
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 91-65-6(Hazardous Substances Data)

Usage

Purification Methods

Dry the amine with BaO and fractionally distil it. The picrate has m 98-99o (from aqueous EtOH) and the methiodide has m 224o (from Me2CO/pet ether) [Cadogan J Chem Soc 1081 1957.] [Bain & Pollard J Am Chem Soc 61 2704 1939, Beilstein 12 H 6, 12 III 14, 12 IV 19.]

InChI:InChI=1/C10H21N/c1-3-11(4-2)10-8-6-5-7-9-10/h10H,3-9H2,1-2H3

Upstream product

• 64-67-5 diethyl sulfate 
• 108-91-8 cyclohexylamine 
• 75-03-6 ethyl iodide 
• 64-17-5 ethanol 
• 75-05-8 acetonitrile 
• 108-93-0 cyclohexanol 
• 108-94-1 cyclohexanone 
• 109-89-7 diethylamine 
• 617-84-5 N-formyldiethylamine 
• 56553-60-7 sodium tris(acetoxy)borohydride 
• 108-95-2 phenol 
• 5459-93-8 N-ethyl-cyclohexanamine 
• 64-19-7 acetic acid 
• 60-29-7 diethyl ether 

Downstream Products

• 108836-05-1 <2-(ω-chlorohexafluoro-n-butyryl)vinyl>ethylcyclohexylamine 
• 1071654-34-6 N-cyclohexyl-N-ethyl-N'-tosylformimidamide 
• 203450-53-7 1,1-diethyl-3-(pyridin-2-yl)urea 
• 1227614-32-5 C₁₄H₂₁N₃O 
• 1696-17-9 N,N-diethylbenzamide 
• 76187-22-9 N-cyclohexyl-N-ethylbenzamide 
• 91-66-7 N,N-diethylaniline 
• 5459-93-8 N-ethyl-cyclohexanamine 
• 75-07-0 acetaldehyde 
• 134694-58-9 Methyl 5S-Hydroxy-5-methyl-6R-(4-carbomethoxyphenylthio)eicosa-7E,9E,11Z,14Z-tetraenoate 
• 108-93-0 cyclohexanol 
• 42362-44-7 1,1-Bis-(2,4-dinitrophenylthio)-2-N-ethylcyclohexylamino-ethen 
• 52011-00-4 (perfluoro)N(methyl),N(ethyl)-n-hexylamine 
• 52011-01-5 (perfluoro)N,N-diethyl-n-hexylamine 

Relevant articles and documents

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

N-Alkylation of amines with phenols over highly active heterogeneous palladium hydride catalysts

Phenols are directly converted to secondary amines in considerable yield via hydrogenation and amination tandem reaction over Al2O3 supported palladium hydride (PdHx) bi-functional catalyst. Note that this system proceeds efficiently with mild conditions under H2 atmosphere, which was difficult to achieve in previous reports. The catalyst and the mechanism of reaction are both studied. Furthermore, various secondary amines can be formed in good yields under this conversion system.