24593-48-4

Basic information

• Product Name: L-4-Methoxyphenylglycine
• Synonyms: (S)-2-amino-2-(4-methoxyphenyl)acetic acid;Benzeneacetic acid, a-aMino-4-Methoxy-, (aS)-;(S)-2-(4-Methoxyphenyl)glycine;S-4-methoxyphenylglycine
• CAS NO: 24593-48-4
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Mol File: 24593-48-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 248-249 °C
• Boiling Point: 339.5±37.0 °C(Predicted)
• Appearance: /
• Density: 1.246±0.06 g/cm3(Predicted)
• PKA: 2.09±0.10(Predicted)
• CAS DataBase Reference: L-4-Methoxyphenylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: L-4-Methoxyphenylglycine(24593-48-4)
• EPA Substance Registry System: L-4-Methoxyphenylglycine(24593-48-4)

Safety Data

• Hazardous Substances Data: 24593-48-4(Hazardous Substances Data)

Usage

General Description

L-4-Methoxyphenylglycine, also known as 4-Methoxyphenylglycine or MPG, is a chemical compound and an important intermediate in the synthesis of pharmaceuticals and agrochemicals. It is commonly used as a chiral building block in the production of various drugs, such as anti-inflammatory and anti-cancer medications. L-4-Methoxyphenylglycine is a white to off-white crystalline powder with a molecular formula C9H11NO3 and a molecular weight of 189.19 g/mol. It is considered a non-proteinogenic amino acid and is used in organic synthesis for the preparation of complex molecules. L-4-Methoxyphenylglycine’s applications extend to the pharmaceutical and agricultural industries, making it a valuable compound in the field of chemistry.

Upstream product

• 24593-47-3 DL-N-(chloroacetyl)-2-(4-methoxyphenyl)glycine 
• 74273-47-5 methyl 2-amino-2-(4-methoxyphenyl)acetate 
• 67-66-3 chloroform 
• 123-11-5 4-methoxy-benzaldehyde 
• 75984-71-3 (S)-(4-Methoxy-phenyl)-{[1-phenyl-meth-(E)-ylidene]-amino}-acetic acid methyl ester 
• 144744-44-5 (3S,5R,6S)-3-(4-Methoxy-phenyl)-5,6-diphenyl-morpholin-2-one 
• 144744-25-2 (3R,5S,6R)-2,3,5,6-Tetrahydro-3-(p-methoxyphenyl)-5,6-diphenyl-1,4-oxazin-2-one 
• 129505-13-1 (2S,2'S)-N-<2'-amino-2'-(4''-methoxyphenyl)acetyl>bornane-10,2-sultam hydrochloride 
• 52771-14-9 2-acetamido-2-(4-methoxyphenyl) acetic acid 
• 1037074-17-1 (S)-(4-Methoxy-phenyl)-{[1-phenyl-meth-(Z)-ylidene]-amino}-acetonitrile 
• 42456-26-8 2-amino-2-(4-methoxyphenyl)acetonitrile 
• 76986-15-7 2-amino-2-(4-methoxyphenyl)acetamide 
• 85803-46-9 (R)-N-(p-Methoxybenzylidene)-2-amino-2-phenylethanol 
• 139224-89-8 N-<(R)-2-hydroxy-1-phenylethyl>-(S)-α-amino-4-methoxybenzeneacetonitrile 

Downstream Products

• 32462-30-9 (S)-hydroxyphenylglycine 
• 169273-94-3 (S)-(N-benzyloxycarbonyl)-p-methoxyphenylglycine 
• 191109-48-5 (S)-2-amino-2-(4-methoxyphenyl)-1-ethanol 

Relevant articles and documents

Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC-MS

A high-throughput screening for the identification of nitrilases demonstrating activity towards alpha-aminonitriles is reported. A LC-MS assay giving access to both conversion and enantiospecificity was developed. 588 candidate enzymes were screened as cell lysates against six alpha-aminonitriles in 96-well microplates. The candidate enzymes were selected following two criteria, their sequence identity with a set of known nitrilases or their phylogenetic position among the nitrilase superfamily. Five enzymes were identified and found to hydrolyse alpha-aminonitrile into the corresponding alpha-aminoacid. The substrate range was found to be very narrow as only two different alpha-aminonitriles, 2-aminovaleronitrile and 2-amino-2- phenylacetonitrile, were found to be substrates. The biocatalytic capabilities of three enzymes were further investigated and the best result was obtained with an enzyme from Burkholderia xenovorans catalysing the enantiospecific hydrolysis of 2-aminovaleronitrile into (S)-norvaline with excellent conversion and enantiomeric excess.

Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles

Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

Syntheses of optically active α-amino nitrites by asymmetric transformation of the second kind using a principle of O. Dimroth

A mixture of solids As and Bs in equilibrium with the dissolved compounds A1 and B1 is transformed completely into one pure solid, say Bs, if the dissolved compounds A1?B1 are equilibrating in solution. This is applied to transform 1:1 mixtures of solid diastereomeric amygdalates (2-hydroxy-2-phenylacetates; mandelates) (R,R)-3 + (S,R)-3 prepared from racemic α-amino nitriles (R,S)-1 with (R)-mandelic acid 2 into stereochemically pure single diastereomers (R,R)-3, or (S,R)-3 (de > 97%) ('asymmetric transformation of the second kind by application of Dimroth's principle'). Decomposition of the amygdalates (R,R)-3, or (S,R)-3, with aqueous base affords the enantiomerically pure α-amino nitriles (A)-1, or (S)-1 (ten examples). The chiral auxiliary (R)-mandelic acid is recovered almost quantitatively. The optically active α-amino nitriles are hydrolyzed to amides 6, and further to α-N-alkylamino acids 7. N-Benzylamino acids 7 are hydrogenated to α-amino acids 8. Some of the optically active α-amino nitriles 1 are reduced to optically active 1,2-diamines 9. In most cases, absolute configurations could be assigned by comparison of the specific rotations observed with those of authentic compounds.