17279-31-1

Basic information

• Product Name: (S)-(-)-N,N-DIMETHYL-1-PHENETHYLAMINE
• Synonyms: ALPHA,N,N-TRIMETHYLBENZYLAMINE;(S)-(-)-N,N-DIMETHYL-1-PHENETHYLAMINE, 9 7%;(S)-(-)-N,N-Dimethyl-1-phenethylamine, 99+%;(s)-(-)-n,n,α-trimethylbenzylamine;(1S)-N,N-Dimethyl-1-phenylethanamine;(S)-N,N,α-Trimethylbenzenemethanamine;(αS)-N,N,α-Trimethylbenzenemethanamine;[(S)-α-Methylbenzyl]dimethylamine
• CAS NO: 17279-31-1
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 241-310-8
• Mol File: 17279-31-1.mol
• Article Data: 54

Chemical Properties

• Melting Point: 143°C (estimate)
• Boiling Point: 81 °C16 mm Hg(lit.)
• Flash Point: 148 °F
• Appearance: Clear colorless to yellow liquid
• Density: 0.905 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.568mmHg at 25°C
• Refractive Index: n20/D 1.503
• Storage Temp.: 0-6°C
• PKA: 8.88±0.50(Predicted)
• BRN: 3196218
• CAS DataBase Reference: (S)-(-)-N,N-DIMETHYL-1-PHENETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N,N-DIMETHYL-1-PHENETHYLAMINE(17279-31-1)
• EPA Substance Registry System: (S)-(-)-N,N-DIMETHYL-1-PHENETHYLAMINE(17279-31-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• RIDADR: 2810
• WGK Germany: 2
• F: 8-10-23
• Hazardous Substances Data: 17279-31-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Purification Methods

The amine is mixed with aqueous 10N NaOH and extracted with toluene. The extract is washed with saturated aqueous NaCl, dried over K2CO3, and transferred to fresh K2CO3 until the solution is clear, and is filtered. The filtrate is distilled. If a short column packed with glass helices is used, the yield is reduced but a purer product is obtained. [Ingersoll Org Synth 25 89 1945, Snyder & Brewster J Am Chem Soc 71 291 4165 1949, Cope et al. J Am Chem Soc 71 3931 1949.] The (-)-picrate has m 140-141o from EtOH). The racemate [1126-71-2] has b 88-89o/16mm, 92-94o/30mm, 194-195o/760mm, d4 0.908. [Beilstein 13 III 2392.]

InChI:InChI=1/C10H15N/c1-9(11(2)3)10-7-5-4-6-8-10/h4-9H,1-3H3/p+1/t9-/m0/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 827-36-1 2-(N,N-dimethylamino)-2-phenylacetonitrile 
• 50-00-0 formaldehyd 
• 618-36-0 rac-methylbenzylamine 
• 5350-67-4 α-(dimethylamino)-propionitrile 
• 5350-41-4 trimethylbenzylammonium bromide 
• 591-51-5 phenyllithium 
• 585-71-7 (1-bromoethyl)benzne 
• 124-40-3 dimethyl amine 
• 98-86-2 acetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 77-78-1 dimethyl sulfate 
• 13437-79-1 (α)-methylbenzylamine hydrochloride 

Downstream Products

• 1517-69-7 (R)-1-phenylethanol 
• 42142-07-4 dimethyl-(1-phenyl-ethyl)-amine oxide 
• 53759-17-4 α-methylbenzyl trimethyl ammonium iodide 
• 96990-21-5 Hexadecyl-dimethyl-(1-phenyl-ethyl)-ammonium; bromide 
• 50640-91-0 (S)-N,N-dimethyl-N-hexadecyl-n(α-methyl-benzyl)ammonium bromide 
• 36043-87-5 N,N,N-trimethyl-1-phenylethan-1-aminium bromide 
• 122571-79-3 α-methyl-N,N-dimethyl-2-hydroxymethylbenzylamine 
• 106997-31-3 (S)-dibutphos*HCl 
• 64234-71-5 lithium(N,N,α-trimethyl-benzylamine) 
• 14898-86-3 (R)-2-methyl-1-phenylpropan-1-ol 
• 84194-66-1 (R)-2-methyl-1-phenylpropyl acetate 
• 84194-67-2 (S)-2-methyl-1-phenylpropyl acetate 
• 2114-29-6 (R)-1-phenylpropyl acetate 
• 2114-29-6 (S)-1-phenylpropyl acetate 

Relevant articles and documents

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N-Methylation of Amines with Methanol at Room Temperature

N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups. (Chemical Presented)

Studies on the configuration of nitrogenous stereogenic centres in adducts of rhodium(II) tetraacylates with chiral amines: the application of 1H and 13C NMR spectroscopy

The 1H and 13C NMR spectra of enantiomerically pure amines (S)-N,N-dimethyl-1-phenylethylamine, (S)-N-methyl-1-phenylethylamine, (S)-N-ethyl-1-phenylethylamine and (S)-N-ethyl-N-methyl-1-phenylethylamine in the presence of a twofold molar excess of dirhodium(II) tetratrifluoroacetate and dirhodium(II) Mosher's acid derivatives [(4S) and (4R)] were measured in CDCl3 as a solvent. The amines having various substituents at the nitrogen atom (H, CH3 and CH2CH3) formed in such conditions as an equilibrium mixture of CSNR and CSNS 1:1 adducts. The signals of both diastereoisomers were observed in NMR spectra at either room temperature (303 K) or moderately decreased temperatures (263-273 K). The rates of mutual diastereoisomer conversion were estimated by selective inversion recovery experiments and varied from less than 0.1 to ca. 10 s-1, depending on the ligand and temperature. Analysis of 13C NMR data and NOE experimental data resulted in the unambiguous determination of the configuration at the nitrogen atom with respect to the carbon stereogenic centre. Modelling of adduct structures and calculations of molecular energy and NMR parameters (GIAO) using Density Functional Theory (DFT) were performed in order to support the experimental findings. The calculations were carried out using 3-21G//B3LYP (structure optimizing) and 311G(2d,p)/LanL2DZ//B3LYP theory levels (molecular energy and NMR shielding).

Pd(II)-Mediated C?H Activation for Cysteine Bioconjugation

Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition-metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C?H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user-friendly synthesis, common Pd(II) sources, and a more cost-effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.