2439-54-5

Basic information

• Product Name: N-METHYLOCTYLAMINE
• Synonyms: METHYL-N-OCTYLAMINE;N-METHYLOCTYLAMINE;N-METHYL-N-OCTYLAMINE;N-OCTYLMETHYLAMINE;1-Octanamine,N-methyl-;methyl(octyl)amine;Methyloctylamine;n-methyl-1-octanamin
• CAS NO: 2439-54-5
• Molecular Formula: C₉H₂₁N
• Molecular Weight: 143.27
• EINECS: 219-462-1
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Polyamines
• Mol File: 2439-54-5.mol

Chemical Properties

• Melting Point: -13°C
• Boiling Point: 68 °C (8 mmHg)
• Flash Point: 63 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.79
• Vapor Pressure: 0.867mmHg at 25°C
• Refractive Index: 1.426-1.428
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.93±0.10(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: N-METHYLOCTYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLOCTYLAMINE(2439-54-5)
• EPA Substance Registry System: N-METHYLOCTYLAMINE(2439-54-5)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 34-43-41-26-22
• Safety Statements: 36/37/39-28A-25-37-36-26
• RIDADR: 2735
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2439-54-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

InChI:InChI=1/C9H21N/c1-3-4-5-6-7-8-9-10-2/h10H,3-9H2,1-2H3

Upstream product

• 111-85-3 n-chlorooctane 
• 74-89-5 methylamine 
• 111-83-1 1-bromo-octane 
• 63493-49-2 N,N,N',N'-Tetramethyl-N''-octanoyl-guanidine 
• 1119-57-9 N-methyloctanoylamide 
• 128326-42-1 2-[methyl(octyl)amino]acetonitrile 
• 109-73-9 N-butylamine 
• 111-86-4 n-Octylamine 
• 2258-42-6 formyl acetic anhydride 
• 67-56-1 methanol 
• 7647-01-0 hydrogenchloride 
• 855895-81-7 1,2-dimethyl-hexahydro-azocin-3-one 
• 7732-18-5 water 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 23580-89-4 methyl-(3-phenyl-propyl)-amine 
• 87462-13-3 1-(n-octylamino)-3-phenylpropane 
• 143832-72-8 (R)-5-[N-methyl-N-(n-octyl)]-amino-2-(3,4,5-trimethoxyphenyl)-2-isopropylvaleronitrile 
• 7378-99-6 N,N-dimethyloctanamide 
• 129-73-7 bis(4-dimethylaminophenyl)phenylmethane 
• 1383141-03-4 4,4'-bis(methylbutylamino)triphenylmethane 
• 1383141-06-7 4-dimethylamino-4'-(methyloctylamino)triphenylmethane 
• 1213299-82-1 N₅-octyl-N₅-methyl-N₁-(4-chlorobenzyl)biguanide 
• 1213230-49-9 N₅-octyl-N₅-methyl-N₁-(3,4-dichlorobenzyl)biguanide hydrochloride 
• 1213230-48-8 N₅-octyl-N₅-methyl-N₁-(4-chlorobenzyl)biguanide hydrochloride 
• 1213230-21-7 N₄-octyl-N₄-methyl-1,6-dihydro-6,6-dimethyl-N₂-(4-methylbenzyl)-1,3,5-triazine-2,4-diamine 
• 1213230-11-5 N₄-octyl-N₄-methyl-1,6-dihydro-6,6-dimethyl-N₂-(3,4-dichlorobenzyl)-1,3,5-triazine-2,4-diamine 
• 1213230-22-8 N₄-octyl-N₄-methyl-1,6-dihydro-6,6-dimethyl-N₂-(4-methylbenzyl)-1,3,5-triazine-2,4-diamine acetate 
• 1213230-12-6 N₄-octyl-N₄-methyl-1,6-dihydro-6,6-dimethyl-N₂-(3,4-dichlorobenzyl)-1,3,5-triazine-2,4-diamine acetate 

Relevant articles and documents

Extraction of U(VI) with N,N'-dimethyl-N,N'-dioctylmalonamide from nitrate media

The extraction of uranyl nitrate with the novel extractant N,N '-dimethyl-N,N '-dioctylmalonamide (DMDOMA) from aqueous sodium nitrate (and nitric acid) was investigated. The extraction mechanism was established and the stoichiometry of the main extracted species confirms to UO2(NO 3)2 · DMDOMA. The IR spectral study was also made of the extracted species. Methyl substituent improves the extraction ability of malonamide for U(VI) compared with that of N,N,N ', N '-tertrabutylmalonamide (TBMA). Pleiades Publishing, Ltd., 2010.

A METHOD FOR PREPARING ALKYLATED AMINES

The present invention pertains to a method for preparing an alkylated amine by reacting a primary or secondary amine with an alcohol in the presence of hydrogen, a metal catalyst supported by photosensitive titanium oxide, and UV irradiation. Advantageously, the reaction can be carried out under mild reaction conditions.

Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for N, N-Dimethylamine Derivatives

A new catalytic system for N,N-dimethylamination of primary alcohols using aqueous dimethylamine in the absence of additional organic solvents has been developed. The reaction proceeds via borrowing hydrogen processes, which are atom-efficient and environmentally benign. An iridium catalyst bearing an N-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable N,N-dimethylamine derivatives, including biologically active and pharmaceutical molecules, were synthesized. The practical application of this methodology was demonstrated by a gram-scale reaction.

Ru-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source

Methanol can be employed as a green and sustainable methylating agent to form C-C and C-N bonds via borrowing hydrogen (BH) methodology. Herein we explored the activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions. Our catalytic system shows great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products. We investigated the mechanistic details, kinetic progress, and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, is the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chemistry metrics are calculated. Furthermore, dimerization of 2-naphthol via methylene linkage and formation of N-methylation of amine are also described in this study, which offers a wide range of substrate scope with a good to excellent yield.

N-Methylation of amines and nitroarenes with methanol using heterogeneous platinum catalysts

We report herein the selective N-methylation of amines and nitroarenes with methanol under basic conditions using carbon-supported Pt nanoparticles (Pt/C) as a heterogeneous catalyst. This method is widely applicable to four types of N-methylation reactions: (1) N,N-dimethylation of aliphatic amines under N2, (2) N-monomethylation of aliphatic amines under 40 bar H2, (3) N-monomethylation of aromatic amines under N2, and (4) tandem synthesis of N-methyl anilines from nitroarenes and methanol under 2 bar H2. All these reactions under the same catalytic system showed high yields of the corresponding methylamines for a wide range of substrates, high turnover number (TON), and good catalyst reusability. Mechanistic studies suggested that the reaction proceeded via a borrowing hydrogen methodology. Kinetic results combined with density functional theory (DFT) calculations revealed that the high performance of Pt/C was ascribed to the moderate metal–hydrogen bond strength of Pt.

Selective Monomethylation of Amines with Methanol as the C1 Source

The N-monomethyl functionality is a common motif in a variety of synthetic and natural compounds. However, facile access to such compounds remains a fundamental challenge in organic synthesis owing to selectivity issues caused by overmethylation. To address this issue, we have developed a method for the selective, catalytic monomethylation of various structurally and functionally diverse amines, including typically problematic primary aliphatic amines, using methanol as the methylating agent, which is a sustainable chemical feedstock. Kinetic control of the aliphatic amine monomethylation was achieved by using a readily available ruthenium catalyst at an adequate temperature under hydrogen pressure. Various substrates including bio-related molecules and pharmaceuticals were selectively monomethylated, demonstrating the general utility of the developed method.

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.

One-pot anti-markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination

A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.

Synthesis of nonsymmetrical dialkylamines on the basis of diphenylphosphinic amides

A facile method for the synthesis of nonsymmetrical dialkylamines (C nH2n+1)2NH (n = 1-12) using the Ph 2P(O) protecting group was developed. The method includes successive transformation of monoalkylamines to primary diphenylphosphinic N-alkylamides Ph2P(O)NHR' (R' = CnH2n+1, n = 1-12) by the Todd-Atherton reaction, phase transfer N-alkylation of these compounds, and hydrolysis of the secondary amides Ph2P(O)NR'R″ thus formed. When the (EtO)2P(O) and Bu2P(O) protecting groups are used, N-alkylation of primary amides is accompanied by the formation of Et-O and P-N bond cleavage products, respectively. A study of the stability of the N-alkylamides R2P(O)NHR' (R = Ph, p-MeC6H4, p-CIC6H4, Bu) under strong alkaline conditions used in the phase transfer N-alkylation showed that an increase in the electron-donating ability of substituents at both the nitrogen atom and the phosphorus atom results in a decrease in the degree of P-N bond cleavage. The primary and secondary diphenylphosphinic amides containing a β-hydroxyethyl group at the nitrogen atom are extremely unstable under the alkaline conditions and are converted quantitatively to the diphenylphosphinic acid salt.

Gas-phase selective N-alkylation of amines with alcohols over γ- alumina

Gas-phase conditions were successfully used for fine chemistry, in the N-alkylation of amines with alcohols as alkylating agents and γ-alumina as a catalyst. The method is also suitable for chiral compounds.