95255-51-9

Basic information

• Product Name: Phenol, 2-[(1E)-1-[[(1R)-1-phenylethyl]imino]ethyl]-
• CAS NO: 95255-51-9
• Molecular Formula: C16H17NO
• Molecular Weight: 239.317
• Mol File: 95255-51-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Phenol, 2-[(1E)-1-[[(1R)-1-phenylethyl]imino]ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2-[(1E)-1-[[(1R)-1-phenylethyl]imino]ethyl]-(95255-51-9)
• EPA Substance Registry System: Phenol, 2-[(1E)-1-[[(1R)-1-phenylethyl]imino]ethyl]-(95255-51-9)

Safety Data

• Hazardous Substances Data: 95255-51-9(Hazardous Substances Data)

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 19019-21-7 1-(2-hydroxyphenyl)-3-methylbutan-1-one 
• 3226-15-1 1-(2-hydroxyphenyl)hexan-1-one 
• 223269-04-3 (4R)-4-methyl-3-<(1'R)-1'-phenylethyl>-3,4-dihydro-2H-1,3-benzoxazine 
• 123983-05-1 2?[(1R)?1-aminoethyl]phenol 

Relevant articles and documents

Asymmetric Syntheses of 2-(1-Aminoethyl)phenols

Three different routes were probed for the synthesis of enantiomerically enriched 2-(1-aminoethyl)phenols and their methyl ethers. The first route centers on diastereoselective nucleophile addition to chiral imines. The second route has as key steps the enantioselective reduction of a ketone followed by nucleophilic substitution, and the third route involves a diastereoselective imine reduction. The efficiency of the approach depends on the substrate substitution pattern. All three methods work well for the parent compound 2-(1-aminoethyl)phenol (1) but the third route is the most efficient, providing the compound with >96% enantiomer excess in three steps with an overall yield of 71%. Conversely, for the ortho-methyl analogue 2, the first method is best. For the t-Bu-substituted analogue 3, only moderate enantiomeric enrichment was achieved.

Ready N-alkylation of enantiopure aminophenols: Synthesis of tertiary aminophenols

A regioselective indirect alkylation of aminophenols to enantiopure tertiary aminophenols, which are useful chiral ligands for metal-catalysed asymmetric reactions, is reported. This very simple synthetic methodology, through reduction or alkylation of an intermediate benzoxazine, was performed in mild conditions, suitable for the conservation of the configuration of the stereogenic centres. Some crystalline aminophenols show the phenomenon of 'crystallization-induced asymmetric transformation'.

Rhodium(I) complexes of β-diketonates and related ligands as hydrosilylation catalysts

The complexes (O-O)Rh(CH2CH2)2 ((O-OH)=FcC(O)CH2C(O)CH3, PhC(O)CH2C(O)CH3, 1,2-(CH3CO)(OH)C6H4, 3-benzoyl-(+)-camphor) are catalysts for the hydrosilylation of PhMeCO with Ph2SiH2.The optical yield from the reaction catalyzed by the camphor derivative is too low to measure.Only low optical yields (max 8.7percent e.e.) are obtained from the same reaction by using similar in situ catalysts with ligands prepared from (+)-PhCH(Me)NH2.Bases such as H- and PhCH(Me)NH- catalyze the hydrosilylation reaction in the absence of rhodium salts, but only low optical yields are obtained.Ph2SiH2 reacts with 2-cyclohexen-1-one under these conditions and the mode of reaction depends on the reaction conditions.