103421-77-8

Basic information

• Product Name: R,S-N,N`-bis(α-methylbenzyl)ethylenediamine
• Synonyms: R,S-N,N`-bis(α-methylbenzyl)ethylenediamine
• CAS NO: 103421-77-8
• Molecular Weight: 268.402
• Mol File: 103421-77-8.mol

Chemical Properties

• CAS DataBase Reference: R,S-N,N`-bis(α-methylbenzyl)ethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: R,S-N,N`-bis(α-methylbenzyl)ethylenediamine(103421-77-8)
• EPA Substance Registry System: R,S-N,N`-bis(α-methylbenzyl)ethylenediamine(103421-77-8)

Safety Data

• Hazardous Substances Data: 103421-77-8(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 138812-17-6 N,N'-bis<(S)-1-phenylethyl>ethanediimine 
• 106-93-4 ethylene dibromide 
• 107-06-2 1,2-dichloro-ethane 
• 16888-80-5 bis(acetophenone)ethylenediamine 
• 98-84-0 D(+)-α-methylbenzylamine 
• 98-86-2 acetophenone 
• 107-15-3 ethylenediamine 

Downstream Products

• 1370700-77-8 1,3-di(1-phenylethyl)imidazolinium chloride 
• 76695-20-0 3-Ethyl-1,5-bis-(1-phenyl-ethyl)-[1,5,3]diazaphosphepane 
• 65837-86-7 2-phenyl-1,3-(S,S)-bis-(1-phenyl-ethyl)-[1,3,2]diazaphospholidine 
• 1130601-53-4 1,3-bis((S)-1-phenylethyl)imidazolidin-2-imine 
• 114613-23-9 cis-dichloro(R,S-N(R),N`(S)-bis(α-methylbenzyl)ethylenediamine)platinum(II) 
• 114613-24-0 cis(dichloro-R,S-N(S),N`(R)-bis(α-methylbenzyl)ethylenediamine)platinum(II) 
• 114613-25-1 trans-(dichloro-R,S-N,N`(S)-bis(α-methylbenzyl)ethylenediamine)platinum(II) 
• 76695-19-7 3-Cyclohexyl-1,5-bis-(1-phenyl-ethyl)-[1,5,3]diazaphosphepane 
• 76695-25-5 N,N'-Bis-{[(4-chloro-phenyl)-phenyl-phosphanyl]-methyl}-N,N'-bis-(1-phenyl-ethyl)-ethane-1,2-diamine 
• 76695-24-4 N,N'-Bis-{[(4-fluoro-phenyl)-phenyl-phosphanyl]-methyl}-N,N'-bis-(1-phenyl-ethyl)-ethane-1,2-diamine 
• 76695-23-3 N,N'-Bis-[(diphenylphosphanyl)-methyl]-N,N'-bis-(1-phenyl-ethyl)-ethane-1,2-diamine 
• 76695-18-6 3-Phenyl-1,5-bis-(1-phenyl-ethyl)-[1,5,3]diazaphosphepane 
• 76706-77-9 3-Methyl-1,5-bis-(1-phenyl-ethyl)-[1,5,3]diazaphosphepane 
• 235422-39-6 (Zn(C₂H₅)(C₆H₅CH(CH₃)NC₂H₄NCH(CH₃)C₆H₅CHC₆H₅O))2 

Relevant articles and documents

Enantioselective catalytic rearrangement of cyclohexene oxide with new homochiral bis-lithium amide bases

Cyclohexene oxide can be rearranged with good levels of induction (up to 68% ee) with substoichiometric amounts of chiral bases derived from readily available diamines. The influence of the steric bulk of the amine substituents on the rearrangement enantioselectivity has also been studied.

α-Phenylethylamine based chiral phospholidines; new agents for the determination of the enantiomeric excess of chiral alcohols, amines and thiols by means of 31P NMR

The synthesis and application of two new trivalent phosphorus derivatizing agents, based upon (S)-α-phenylethylamine, for the enantiomeric excess determination of alcohols, amines and thiols using 31P NMR, is presented.

Imidazolinium chloride salts bearing wingtip groups: Synthesis, molecular docking and metabolic enzymes inhibition

A series of symmetrical imidazolinium chloride salts bearing secondary N-alkyl substituents were synthesized in good yield by the reaction of N,N′-dialkylethane-1,2-diamines and HC(OEt)3 in the presence of NH4Cl. These salts were characterized by spectroscopic methods. All compounds were tested as enzyme inhibitory agents. These novel symmetrical imidazolinium chloride salts derivatives (3a-h) effectively inhibited the cytosolic hCA I and hCA II, BChE, α-glycosidase and AChE with Ki values in the range of 18.41–121.73 nM for hCA I, 12.50–63.12 nM for hCA II, 3.72–34.58 nM for AChE, 5.50–32.36 nM for BChE, and 94.72–364.51 nM for α-glycosidase, respectively. CA isoenzymes play a crucial roles including acid-base balance homeostasis by excreting and secreting protons (H+) due to the CO2 hydration, HCO3 ? reabsorption mechanisms, and renal NH4 + output. Also, the molecular modeling is an implementation for estimation of the binding proximity of symmetrical imidazolinium chloride salts bearing secondary wingtip groups and their inhibition mechanisms and kinetics in atomic levels at the catalytic domains.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate

Two chiral 2-azidoimidazolinium salts [(7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate (2) and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate (3)] were synthesized, and their structures were determined by X-ray single crystal structural analysis. Migratory amidation reaction of enol silyl ether with 3 proceeded, but good diastereoselectivity was not observed in the reaction.

Synthesis of chiral phosphorus reagents and their application in combination with lewis acid as a cocatalyst in morita-baylis-hillman reaction

Two novel chiral thiophosphoramides and two chiral phosphoramidites were synthesized starting from (S)-α-phenylethylamine and (R)-(+) or (S)-(-)-1,1'-Bi-2-naphthol (BINOL), respectively, and their application in combination with Lewis acid as cocatalysts in asymmetric Morita-Baylis-Hillman (MBH) reaction was investigated. Dramatic rate acceleration (the corresponding adducts were obtained in fair to excellent chemical yield within 15 min-5 h) was observed in these chiral phosphorus reagents/Lewis acid cocatalyzed MBH reaction between 4-nitrobenzaldehyde and activated alkenes, and in one case, moderate enantioselectivity was achieved (the corresponding adduct's ee value is 44%). Copyright Taylor and Francis Group, LLC.

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction

A series of chiral guanidines were synthesized and shown to efficiently catalyze the aza-Henry reaction. Modifications of the catalyst structure revealed important selectivity trends as well as an intriguing reversal in stereoselectivity with bisguanidine

Chiral bidentate aminophosphine ligands: Synthesis, coordination chemistry and asymmetric catalysis

Chiral aminophosphines Ph2PN(R)(CH2) nN(R)PPh21-4 [n = 2, R = CH(CH3)(Ph) 1; n = 3, R = CH(CH2CH3)(Ph) 2, n = 2, R = CH(CH3)(1- naphthyl) 3; n = 2, R = CH(CH3)(C6H11) 4] were synthesized by the reaction of ClPPh2 with the appropriate easily accessible enantiopure amine building blocks. For compounds 1 and 2, the corresponding selenides 5 and 6 were prepared to determine the electronic character of the phosphine moieties. By reaction of 1 with either PdCl 2(cod) or PdCl(CH3)(cod) the cis-complexes 7 and 8 were obtained. The molecular structure for complex 7, cis-[PdCl2(1)], was determined by X-ray crystallography. Reaction of PtCl2(cod) with 1 or 2 yielded the corresponding monomeric cis-isomers 9 and 10. The rhodium derivative [RhCl(CO)(1)] (11) was obtained as a mixture of cis and trans-isomers. Preliminary results in the rhodium catalyzed hydroformylation of styrene and vinyl acetate, with ee's up to 51% and high regioselectivities, showed the potential of these chiral aminophosphines for homogeneous catalysis.

Increased enantioselectivity in the addition of diethylzinc to benzaldehyde by the use of chiral ligands containing the α-phenylethylamino group in combination with achiral ligands

Chiral ligands (S,S)-1, (S,S)-2, (S,S)-3, (S)-4, (S)-5, (S,S)-6, (S,S)-7, and (S,S)-8 turned out to be effective promoters in the enantioselective addition of diethylzinc to benzaldehyde. Interestingly, diamine (S,S)-3 and amino alcohols (S)-5 and (S,S)-7 induce the preferential formation of carbinol (R)-10 (unlike stereoinduction) whereas amido analogues (S,S)-2, (S)-4, and (S,S)-6 favor (S)-10 (like stereoinduction). Molecular modeling at the semiempirical PM3 level provided a reasonable interpretation based on conformational effects in the corresponding transition structures. Combinations of chiral ligands 1-8 with an achiral, flexible ligand (9) gave rise to an activated catalytic system that resulted in faster and higher yielding reactions. Furthermore, substantial increases in the observed enantiomeric excesses of product 10 confirmed the relevant role of achiral bis-(sulfonamide) 9 as activator and "chiral environment amplifier".