34645-25-5

Basic information

• Product Name: (R)-1,2-Diphenylethylamine
• Synonyms: (R)-1,2-Diphenylethylamine;(1R)-1,2-Diphenylethanamine;(1R)-1,2-Diphenylethane-1-amine;(R)-α-Benzylbenzenemethaneamine;(1R)-1,2-Diphenylethan-1-amine
• CAS NO: 34645-25-5
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.28
• Mol File: 34645-25-5.mol

Chemical Properties

• Boiling Point: 120 °C(Press: 0.3 Torr)
• Appearance: /
• Density: 1.052±0.06 g/cm3(Predicted)
• PKA: 8.78±0.10(Predicted)
• CAS DataBase Reference: (R)-1,2-Diphenylethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,2-Diphenylethylamine(34645-25-5)
• EPA Substance Registry System: (R)-1,2-Diphenylethylamine(34645-25-5)

Safety Data

• Hazardous Substances Data: 34645-25-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1,2-Diphenylethylamine is used as a chiral building block for the production of various pharmaceuticals. Its unique chiral nature allows for the creation of drugs with specific therapeutic effects, enhancing the efficacy and selectivity of medications.
Used in Agrochemical Industry:
(R)-1,2-Diphenylethylamine is used as a chiral building block in the synthesis of agrochemicals. Its incorporation into these compounds can lead to improved pest control and crop protection, as well as reduced environmental impact.
Used in Fragrance Industry:
(R)-1,2-Diphenylethylamine is used as a chiral building block in the creation of fragrances. (R)-1,2-Diphenylethylamine's chirality can contribute to the development of scents with distinct and complex olfactory profiles.
Used in Asymmetric Synthesis:
(R)-1,2-Diphenylethylamine is used as a valuable compound in asymmetric synthesis. Its chiral nature plays a crucial role in the development of novel synthetic methods and the production of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical applications.
Used in Catalysis:
(R)-1,2-Diphenylethylamine is used in catalysis due to its chiral properties. It can serve as a catalyst or be incorporated into catalysts to facilitate enantioselective reactions, leading to the production of enantiomerically enriched products with potential applications in various industries.

Upstream product

• 25611-78-3 (R,S)-1,2-diphenylethylamine 
• 131214-11-4 (2R,1'R)-2-<(1',2'-diphenylethyl)amino>-2-phenylethanol 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 6921-34-2 benzylmagnesium chloride 
• 451-40-1 phenyl benzyl ketone 
• 121328-33-4 3-benzyl-(4S)-isopropyl-1,3-oxazolidin-2-one 
• 100-44-7 benzyl chloride 
• 128013-82-1 (1S,4R)-2-[(E)-(R)-1,2-Diphenyl-ethylimino]-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide 
• 33366-96-0 N'-(1,2-diphenylethylidene)benzohydrazide 
• 49855-40-5 L_g-threo-α'-chloro-bibenzyl-α-ylamine 
• 3938-96-3 ethyl 2-methoxyacetate 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 530-36-9 (1S,2S)-2-amino-1,2-diphenylethanol 

Downstream Products

• 28057-75-2 C₁₅H₁₃NO 
• 79349-11-4 R-N-<(-)-1,2-diphenylethyl>-o-methoxybenzamide 
• 135638-32-3 (2,2-Diethoxy-ethyl)-((R)-1,2-diphenyl-ethyl)-amine 
• 135365-22-9 (R)-3,4-dihydro-1-methyl-3-phenylisoquinoline 
• 1106777-33-6 (R)-N-(1,2-diphenylethyl)benzamide 
• 127529-17-3 (R)-(-)-1-(1,2-diphenylethyl)piperidine 
• 948902-88-3 C₂₅H₃₂N₂O₃ 
• 74619-81-1 N-benzylidene-(-)-1,2-diphenylethylamine 
• 66730-28-7 N-benzoyl-(-)-1,2-diphenylethylamine 
• 134540-83-3 (5R)-5-(4-imidazolylmethyl)-3-<(R)-1,2-diphenylethyl>-2,4-imidazolidinedione 
• 146530-34-9 (R)-2-formyl-1,2,3,4-tetrahydro-3-phenylisoquinoline 
• 146530-36-1 (R)-3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 350678-45-4 (R)-1-Benzyl-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 350678-37-4 N-(2-Benzenesulfinyl-ethyl)-N-((R)-1,2-diphenyl-ethyl)-formamide 

Relevant articles and documents

Engineering the Active Site of an (S)-Selective Amine Transaminase for Acceptance of Doubly Bulky Primary Amines

A protein engineering approach for expanding the substrate scope of the (S)-selective Chromobacterium violaceum amine transaminase is presented. Amino acid residues in the small binding pocket of the active site were targeted in order to increase the pocket size for acceptance of primary amines bearing two bulky groups. A highly sensitive fluorescence assay was then used to evaluate the generated enzyme variants for their activity towards propyl- and benzyl-substituted screening substrates. The best variant, L59A/F88A, was successfully applied in the kinetic resolution of 1,2-diphenylethylamine using different conditions and substrate loadings. The variant L59A/F88A generated enantiomerically pure (R)-1,2-diphenylethylamine with ee>99% under all tested conditions. The variant also holds great promise for synthesis of hydrophobic compounds as it shows optimum activity when 20-30% (v/v) DMSO is applied as cosolvent. The variant L59A/F88A provides a great addition to the available catalyst toolbox for synthesis of chiral amines, as it is the first published (S)-selective amine transaminase showing activity towards benzyl-substituted primary amines. (Figure presented.).

Highly efficient enantioselective liquid-liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts

Access to enantiopure compounds on large scale in an environmentally friendly and cost-efficient manner remains one of the greatest challenges in chemistry. Resolution of racemates using enantioselective liquid-liquid extraction has great potential to meet that challenge. However, a relatively feeble understanding of the chemical principles and physical properties behind this technique has hampered the development of hosts possessing sufficient resolving power for their application to large scale processes. Herein we present, employing the previously untested SPINOL based phosphoric acids host family, an in depths study of the parameters affecting the efficiency of the resolution of amino-alcohols in the optic of further understanding the core principles behind ELLE. We have systematically investigated the dependencies of the enantioselection by parameters such as the choice of solvent, the temperature, as well as the pH and bring to light many previously unsuspected and highly intriguing interactions. Furthermore, utilizing these new insights to our advantage, we developed novel, highly efficient, extraction and resolving protocols which provide remarkable levels of enantioselectivity. It was shown that the extraction is catalytic in host by demonstrating transport in a U-tube and finally it was demonstrated how the solvent dependency could be exploited in an unprecedented triphasic resolution system.

Candida antarctica lipase A and Pseudomonas stutzeri lipase as a pair of stereocomplementary enzymes for the resolution of 1,2-diarylethanols and 1,2-diarylethanamines

Candida antarctica lipase A (CALA) and Pseudomonas stutzeri lipase (PSL) displayed opposite enantioselectivities in the acylation of 1,2-diphenylethanol and 1,2-diphenylethanamine. CALA was (S)-selective while PSL was (R)-selective. In addition, fourteen different 1,2-diarylethanols were tested as the substrates of CALA. It was found that most of them were accepted by CALA with high enantioselectivity. The DKR of five representative substrates by the combination of CALA and a ruthenium-based racemization catalyst provided good yields (82-91%) and acceptable enantiopurities (87-94% ee).

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds

We resolved 1,2-diphenylethylamine (DPEA) into its (S)- and (R)-enantiomer and used them as precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine, flexible homeomorphs of the NMDA channel blocker MK-801. We also describe the synthesis o

Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.

π-π Stacking versus steric effects in stereoselectivity control: Highly diastereoselective synthesis of syn-1,2-diarpropylamines

N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at Cl depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by π-π stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl) arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.

Determination of ring conformation in 1-benzyl-1,2,3,4- tetrahydroisoquinolines and a new synthesis of the chiral compounds

The conformation of the piperideine ring in 1-benzyl-1,2,3,4- tetrahydroisoquinolines was determined as 2H3 form with a pseudoaxial position of the 1-benzyl group by circular dichroism (CD) spectral comparison with 1-methyl-1,2,3,4-tetrahydroisoquinolines. The chiral center at C-1 of 1,2,3,4-tetrahydroisoquinoline (TIQ) was constructed in an unambiguous manner by applying a new method of TIQ synthesis utilizing the Pummerer reaction as a key step. Enantiomerically pure (R)- and (S)-1-methyl- and 1- benzyltetrahydroisoquinolines (1) were prepared starting from readily available chiral amines (2) in good overall yields.

Stereoselective addition reactions to chiral N-benzylidene-P-toluenesulfinamides. Application to the synthesis of optically active 1,2-diphenylethylamines

An efficient and enantiospecific synthesis of substituted 1,2-diphenyl-ethylamines 5 from benzaldehydes is described using a recyclable chiral auxiliary.

A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries

(+)-2-hydroxy-3-pinanone ((+)-HyPN,(+)-2a) and (-)-3-hydroxy-2-caranone ((-)-2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2-thiazolyl)methylamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (-)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27a-d.