40851-64-7

Usage

Uses

Used in Organic Synthesis:
[2-(azidomethyl)phenyl]acetic acid is used as a chemical precursor for the synthesis of various compounds. Its highly reactive azide group allows for the creation of a diverse range of molecules with specific properties, making it a valuable asset in the field of organic synthesis.
Used in Medicinal Chemistry:
In the domain of medicinal chemistry, [2-(azidomethyl)phenyl]acetic acid serves as a building block for the development of new pharmaceuticals. Its unique structure and reactivity enable the design and synthesis of innovative molecules with potential therapeutic applications.
Used in the Creation of New Molecules:
[2-(azidomethyl)phenyl]acetic acid is used as a fundamental building block for the development of novel molecules with specific properties. Its incorporation into molecular structures can lead to the discovery of new materials and compounds with unique characteristics, further expanding the horizons of chemical research and application.

InChI:InChI=1/C9H9N3O2/c10-12-11-6-8-4-2-1-3-7(8)5-9(13)14/h1-4H,5-6H2,(H,13,14)

Upstream product

• 40291-39-2 ethyl 2-(2-methylphenyl)acetate 
• 4385-35-7 isochroman-3-one 
• 39191-76-9 ethyl 2-(2-(bromomethyl)phenyl)acetate 
• 428501-02-4 ethyl 2-(2-(azidomethyl)phenyl)acetate 

Downstream Products

• 428500-96-3 methyl 6-O-[(2-azidomethyl)phenylacetyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 428500-95-2 p-methoxyphenyl 3-O-[(2-azidomethyl)phenylacetyl]-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 428500-98-5 methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside 
• 1062261-07-7 C₂₃H₂₂N₂O₄ 
• 1062261-06-6 C₂₈H₃₁N₃O₅ 
• 1062260-88-1 C₃₃H₃₈N₄O₆ 
• 1062260-99-4 C₃₄H₄₂N₄O₆ 
• 1062260-95-0 C₃₅H₄₄N₄O₆ 
• 1062260-91-6 C₃₄H₄₀N₄O₆ 
• 1062261-05-5 C₂₉H₃₃N₃O₅ 
• 1062261-04-4 C₃₅H₄₄N₄O₆ 
• 641-89-4 anhydrolycorine 
• 40360-71-2 anhydrolycorine-7-one 
• 7135-32-2 1-benzylindolin-2-one 

Relevant academic research and scientific papers

Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids

The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted into four natural alkaloids, namely, assoanine, anhydrolycorine, oxoassoanine, and anhydrolycorinone.

Ligands to the (IRAP)/AT4 receptor encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2

Analogues of the hexapeptide angiotensin IV (Ang IV, Val1-Tyr2-Ile3-His4-Pro5-Phe6) encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2 and a phenylacetic or benzoic acid moiety replacing His4-Pro5-Phe6 have been synthesized and evaluated in biological assays. The analogues inhibited the proteolytic activity of cystinyl aminopeptidase (CAP), frequently referred to as the insulin-regulated aminopeptidase (IRAP), and were found less efficient as inhibitors of aminopeptidase N (AP-N). The best Ang IV mimetics in the series were approximately 20 times less potent than Ang IV as IRAP inhibitors. Furthermore, it was found that the ligands at best exhibited a 140 times lower binding affinity to the membrane-bound IRAP/AT4 receptor than Ang IV. Although the best compounds still exert lower activities than Ang IV, it is notable that these compounds comprise only two amino acid residues and are considerably less peptidic in character than the majority of the Ang IV analogues previously reported as IRAP inhibitors in the literature.

(2-Azidomethyl)phenylacetyl as a new, reductively cleavable protecting group for hydroxyl groups in carbohydrate synthesis

The (2-azidomethyl)phenylacetyl group (AMPA) is described as a new protecting group for carbohydrates. AMPA was introduced to carbohydrate hydroxyl groups in the presence of DCC, while its removal was conveniently achieved via Lindlar catalyst-catalyzed hydrogenation that had no influence on other protecting groups including benzyl, acyl, acetal and ketal.

Preparation of amides from acids and resin bound azides: Suppression of intramolecular lactam formation

A new method for the formation of amides on solid phase has been developed. The procedure involves the reaction between activated acids in solution and resin bound iminophosphoranes generated from the corresponding azides and tributylphosphine. The method is particularly attractive when starting from δ azido acids since amides can form without internal cyclization to the lactam.