66068-76-6

Basic information

• Product Name: (S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID
• Synonyms: (1S)-1-PHOSPHONO-1-ETHANAMINE;D(+)-1-AMINOETHYLPHOSPHONIC ACID;D-ALA(P);H-ALAP-(OH)2;H-AETPO-(OH)2;H-S-ALA(P)-OH;L-1-AMINO-ETHYLPHOSPHONIC ACID;(S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID
• CAS NO: 66068-76-6
• Molecular Formula: C₂H₈NO₃P
• Molecular Weight: 125.06
• Mol File: 66068-76-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 290 °C (dec.)(lit.)
• Boiling Point: 319.2 °C at 760 mmHg
• Flash Point: 146.9 °C
• Appearance: /
• Density: 1.475 g/cm³
• Vapor Pressure: 7.2E-05mmHg at 25°C
• Refractive Index: 1.495
• BRN: 4291033
• CAS DataBase Reference: (S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID(66068-76-6)
• EPA Substance Registry System: (S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID(66068-76-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 66068-76-6(Hazardous Substances Data)

Usage

General Description

(S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID is a chemical compound that is commonly referred to as (S)-Leucinol. It is a chiral phosphonic acid derivative and a key intermediate for the synthesis of various drugs and pharmaceutical products. (S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID is known for its ability to mimic the structure and function of natural amino acids, making it a valuable tool in drug development and research. (S)-(+)-(1-AMINOETHYL)PHOSPHONIC ACID has also been used in the synthesis of peptidomimetics and as a chiral auxiliary in asymmetric catalysis. Its unique structure and reactivity make it a versatile building block for the creation of complex molecules and pharmaceutical compounds.

InChI:InChI=1/C2H8NO3P/c1-2(3)7(4,5)6/h2H,3H2,1H3,(H2,4,5,6)/t2-/m0/s1

Upstream product

• 6323-97-3 1-aminoethanephosphonic acid 
• 65576-94-5 (-)-1-aminoethylphosphonous acid 
• 81069-92-3 (L,D)-1-(N-phenylacetylamino)ethylphosphonic acid 
• 79879-28-0 (D)-1-(N-phenylacetylamino)ethylphosphonic acid 

Downstream Products

• 60668-66-8 [(S)-1-((S)-2-Benzyloxycarbonylamino-propionylamino)-ethyl]-phosphonic acid 
• 65084-56-2 (S)-<1-(benzyloxycarbonylamino)ethyl>phosphonic acid 
• 98820-76-9 [(S)-1-((R)-2-Benzyloxycarbonylamino-propionylamino)-ethyl]-phosphonic acid 

Relevant articles and documents

Biocatalytic resolution of enantiomeric mixtures of 1-aminoethanephosphonic acid

Several fungal strains, namely Bauveria bassiana, Cuninghamella echinulata, Aspergillus fumigatus, Penicillium crustosum and Cladosporium herbarum, were used as biocatalysts to resolve racemic mixtures of 1-aminoethanephosphonic acid using L/D amino acid oxidase activity. The course of reaction was analyzed by 31P-NMR in the presence of cyclodextrin used as chiral discriminating agent. The best result (42% e.e of R-isomer) was obtained with a strain of Cuninghamella echinulata.

Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective enzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids

N-Phenylacetylated derivatives of 1-aminoalkylphosphonic acids were synthesized and high enantioselectivity of their hydrolysis by penicillin acylase (EC 3.5.1.11) was demonstrated. Stereoselective enzymatic hydrolysis of racemic 1-(N-phenylacetylamino) alkylphosphonic acids was used for preparation of enantiomeric 1-aminoalkylphosphonic acids. The kinetic regularities of penicillin acylase catalyzed hydrolysis were established and the biocatalytic process was optimized to increase the optical purity and the yield of the optically active product.

1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.