29289-35-8

Usage

Uses

Used in Organic Synthesis:
()-Azidophenylacetic acid serves as a precursor in the synthesis of a variety of organic compounds, such as pharmaceuticals and dyes. The presence of the azido group allows for easy conversion into an amino group, making it a valuable building block for the preparation of a wide array of chemical compounds.
Used in Photoaffinity Labeling Studies:
In biological systems, ()-azidophenylacetic acid is utilized for photoaffinity labeling studies. The azido group's reactivity enables it to form covalent bonds with target biomolecules upon exposure to ultraviolet light, facilitating the investigation of molecular interactions and mechanisms.
Used in Pharmaceutical Development:
Due to its ability to be converted into an amino group, ()-azidophenylacetic acid is employed in the development of pharmaceuticals. This conversion allows for the creation of new drug candidates with potential therapeutic applications.
Safety Note:
It is crucial to handle ()-azidophenylacetic acid with care, as azides are known to be potentially explosive and toxic. Proper safety measures should be taken during its use to minimize risks.

Upstream product

• 124718-93-0 2-azido-2-phenylethanol 
• 96-09-3 styrene oxide 
• 53432-39-6 (R)-1,1,1-trichloro-2-phenylethan-2-ol 
• 4870-65-9 2-bromophenylacetic acid 

Downstream Products

• 62802-17-9 (6S,7S)-7-(2-Amino-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; hydrochloride 
• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 
• 28357-46-2 azidocillin 
• 4695-47-0 7-chloro-3,5-diphenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 137959-54-7 7,8-Dimethoxy-5-methyl-3-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 2835-06-5 phenylglycin 
• 2935-35-5 (S)-2-phenylglycine 
• 875-74-1 (R)-phenylglycine 

Relevant academic research and scientific papers

Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine

A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.

REAGENTS AND METHODS FOR ESTERIFICATION

Methods and reagents for esterification of biological molecules including proteins, polypeptides and peptides. Diazo compounds of formula (I): where R is hydrogen, an alkyl, an alkenyl or an alkynyl, RA represents 1-5 substituents on the indicated phenyl ring and RM is an organic group, which includes a label, a cell penetrating group, a cell targeting group, or a reactive group or latent reactive group for reaction to bond to a label, a cell penetrating group, or a cell targeting group, among other organic groups are useful for esterification of biological molecules. Also provided are diazo compounds which are bifunctional and trifunctional coupling reagents as well as reagents for the synthesis of compounds of formula (I).

Optimized Diazo Scaffold for Protein Esterification

The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)-glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent. (Chemical Equation Presented).

A practical asymmetric synthesis of homochiral α-arylglycines

Enantioselective reduction of a series of substituted aryl trichloromethyl ketones with the CBS-catecholborane reagent afforded homochiral aryl trichloromethyl carbinols which have been elaborated to give homochiral α-arylglycines in high e.e.

Process for obtaining D(-)-and L(+)-α-azidophenylacetic acid

L(+)- or D(-)-α-azidophenylacetic acid is produced by a process which involves the steps of reacting a water-soluble salt of DL-α-azidophenylacetic acid with a water-soluble salt of an optically active α-phenylethylamine in an aqueous medium, effecting crystallization of the resulting reaction product, that is, the diastereomeric salt, and splitting of the thus-obtained salt.