2153-98-2

Usage

Uses

In the optical resolution of externally compensated acids.

Safety Profile

Different sources of media describe the Safety Profile of 2153-98-2 differently. You can refer to the following data:
1. Poison by intraperitoneal,subcutaneous and intravenous routes. When heated todecomposition it emits very toxic fumes of HCl and NOx.
2. Poison by intraperitoneal route.When heated to decomposition it emits very toxic fumesof HCl and NOx.

InChI:InChI=1/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H/t7-,9+;/m1./s1

Upstream product

• 492-41-1 (1R,2S)-norephedrine 
• 59686-10-1 1-phenyl-2-phthalimido-1-propanol 
• 257952-52-6 (4S,5S)-4-methyl-2,5-diphenyl-4,5-dihydro-1,3-oxazole 
• 5267-71-0 (1R,2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)benzamide 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 123537-84-8 (1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol 
• 123475-40-1 (1S,2S)-1-acetoxy-1-phenyl-3-iodo-2-phthalimidopropane 
• 1884-86-2 (1S,2S)-1-(4-nitrophenyl)-2-phthalimido-1,3-propanediol 
• 123475-39-8 (1S,2S)-1-hydroxy-1-phenyl-2-phthalimido-3-tosyloxy-propane 
• 123475-38-7 (1S,2S)-1(4-aminophenyl)-2-phthalimido-propane-1,3-diol 
• 123537-85-9 (1S,2S)-1-acetoxy-1-phenyl-2-phthalimido-propane 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 42407-55-6 (1RS,2RS)-2-dibenzylamino-1-phenyl-propan-1-ol; hydrochloride 

Downstream Products

• 92686-71-0 (1S,2S)-1-phenyl-1-trimethylsilyloxy-2-amino-propane 
• 92686-80-1 N'-(1S,2S)-1-phenyl-1-trimethylsilyloxy-3-metoxymethyl-2-amino propane 1,2,3,4-tetrahydroisoquinoline 
• 84010-65-1 [1-(3,4-Dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 84010-77-5 [1-[(S)-1-(4-Chloro-butyl)-3,4-dihydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-((R)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 4380-71-6 erythro-2-benzoylamino-1-phenylpropan-1-ol 

Relevant academic research and scientific papers

Stereochemical aspects of phenylethanolamine analogues as substrates of phenylethanolamine N-methyltransferase

Phenylethylamines and phenylethanolamines represent two major classes of ligands for the epinephrine synthesizing enzyme, phenylethanolamine N-methyltransferase (PNMT; EC 2.1.1.28). Phenylethylamines are usually competitive inhibitors and the isomers with the relative configuration as in (2S)-amphetamine and (2S)-2-aminotetralin are better inhibitors than their enantiomers. Phenylethanolamines are usually substrated of PNMT and the enzyme prefers the 1R isomers, such as (1R)-phenylethanolamine, in this class. Optically active norephedrines, norpseudoephedrines, and 2-amino-1-tetralols were used to study the stereochemical requirements of phenylethanolamines for PNMT active site binding. Although the norephedrines and the norpseudoephedrines were poorer ligands for PNMT than were the 2-amino-1-tetralols, (1R,2S)-(-)-norephedrine showed some activity as a pNMT substrate (K(m) = 1310 μM, V(max)/K(m) = 0.017). In the 2-amino-1-tetraols, the isomers with the 2S configuration showed higher affinity to PNMT (13, K(m) = 4.5 μM; 15, K(i) = 4.6 μM) and those with the 1R configuration were substrates for the PNMT-catalyzed methyl transfer (13, K(m) = 4.5 μM, V(max) = 0.16, 100 x V(max)/K(m) = 4.6; 16, K(m) = 195 μM, V(max) = 0.12, 100 x V(max)/K(m) = 0.062); the combination of 1R and 2S configurations, such as in (1R,2S)-2-amino-1-tetralol, was required for a good substrate. These stereochemical requirements derived from the norephedrines, the norpseudoephedrines, and the 2-amino-1-tetralols complement those for phenylethylamines and for phenylethanolamines and strongly suggest that phenylethylamine inhibitors bind to PNMT in the same orientation as do phenylethanolamine substrates.

Simple preparation process of syn phenylpropanolamines from racemic O-TBDPS cyanohydrins

In this article, a practically interesting route for the diastereoselective synthesis of phenylpropanolamines has been demonstrated for the first time. Using racemic O-tert-butyldiphenylsilyl (TBDPS) cyanohydrins as the starting materials, various syn phenylpropanolamines and derivatives (e.g., norpseudophedrine) have been successfully prepared in exellent diastereoselectivity via a practically interesting process.

Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a meso-cyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudoephedrine was developed.

(1S,2S)-2-Amino-1-aryl-propane-1,3-diols as Convenient Educts for the Synthesis of Homochiral (S,S)-Norpseudoephedrine

A convenient high yield synthesis of homochiral norpseudoephedrine starting from waste products of the chloramphenicol synthesis is described as an example of its utilization in chemical transformations.

STEREOCHEMICAL COURSE OF THE REACTION OF 2-HALOETHYL ISOTHIOCYANATES WITH NUCLEOPHILES. sTEREOSPECIFIC ROUTE TO 4,5-DISUBSTITUTED Δ2-THIAZOLINES AND THIAZOLIDINE-2-THIONES

Diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes have been prepared.They reacted stereospecifically with CH3ONa, diethylamine, aniline and NaSH to give pure cis or trans-4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones whose configuration was determined using the nuclear Overhauser effect.The preponderant conformation of diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes was estimated on the basis of coupling constants of vicinal protons.