Methyl 2-azidoacetate

Base Information

• Chemical Name: Methyl 2-azidoacetate
• CAS No.: 1816-92-8
• Molecular Formula: C3H5 N3 O2
• Molecular Weight: 115.092
• Hs Code.: 2929909090
• European Community (EC) Number: 687-878-4
• DSSTox Substance ID: DTXSID70398587
• Nikkaji Number: J1.247.582I
• Wikidata: Q82200659
• Mol file: 1816-92-8.mol

Synonyms:Methyl 2-azidoacetate;1816-92-8;Methyl azidoacetate;Azidoacetic acid methyl ester;Acetic acid, 2-azido-, methyl ester;METHYLAZIDOACETATE;Acetic acid, azido-, methyl ester;azido-acetic acid methyl ester;Azidoacetic acid, methyl ester;methyl azido-acetate;methyl-2-azidoacetate;Methyl 2-azidoacetate, 97%;SCHEMBL13482799;DTXSID70398587;BCP32408;AKOS005174463;FS-4142;BB 0257904;FT-0685510;EN300-72572;V10130;J-521949;6-(2-PYRIDIN-2-YL-PYRROLIDIN-1-YL)-NICOTINICACID

Chemical Property of Methyl 2-azidoacetate

Chemical Property:

• Refractive Index: n20/D1.440
• Boiling Point: 35 °C
• Flash Point: 48℃
• PSA: 76.05000
• Density: 1.182 g/mL at 25 °C
• LogP: -0.07754
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 115.038176411
• Heavy Atom Count: 8
• Complexity: 127

Purity/Quality:

97% ^*data from raw suppliers

Methyl 2-azidoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 5-10-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CN=[N+]=[N-]
• Uses: Methyl 2-azidoacetate is widely used as a precursor to build triazole derivatives via alkyne-azide click chemistry. Some of the examples include the synthesis of coumarin-triazole derivatives as potential antiplasmodial agents and macrocyclic triazole containing largazole analogs as histone deacetylases-1 (HDAC1) inhibitors.It can be used to synthesize various pyrrole derivatives by Knoevenagel condensation as in the synthesis of near-infrared boron dipyrromethene (BODIPY) donors for organic tandem solar cells.It can also be used in Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles.Synthesis of highly fluorescent pyreno[2,1-b]pyrroles using methyl 2-azidoacetate as one of the reagents.

Technology Process of Methyl 2-azidoacetate

There total 7 articles about Methyl 2-azidoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

bromoacetic acid methyl ester (96-32-2) → Methyl azidoacetate (1816-92-8)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 20h;

DOI:10.1021/ol061918j

Reference yield: 99.0%

methyl chloroacetate (96-34-4) → Methyl azidoacetate (1816-92-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 24h;

DOI:10.1016/j.tet.2018.01.013

Reference yield: 82.0%

→ Methyl azidoacetate (1816-92-8)

Guidance literature:

upstream raw materials:

methyl chloroacetate

bromoacetic acid methyl ester

glycine ethyl ester hydrochloride

tetrabutylammoniun azide

Downstream raw materials:

Azidamfenicol

β-(N-Benzyl-3-indolyl-)-α-azidoacrylsaeuremethylester

(Z)-methyl 2-azido-3-phenylacrylate

2-azido-3-(4'-methoxyphenyl)acrylic acid methyl ester

Refernces

Entry into 6-methoxy-D(+)-tryptophans. Stereospecific synthesis of 1-benzenesulfonyl-6-methoxy-D(+)-tryptophan ethyl ester

10.1080/00397919208021343

The research aimed to develop a strategy for synthesizing optically active ring-A methoxylated indole alkaloids, specifically targeting the preparation of 1-benzenesulfonyl-6-methoxy-D(+)-tryptophan ethyl ester (16). This amino ester is crucial for the synthesis of Alstonia bisindole alkaloids, such as macralstonine, which exhibit potent hypotensive properties. The researchers employed the Moody azide/Schollkopf chiral auxiliary protocol to achieve the stereospecific synthesis of the target compound. Key chemicals used in the research included methyl azidoacetate, 4-methoxybenzaldehyde, benzenesulfonyl chloride, sodium borohydride, and various reagents for specific reactions like formylation and decarboxylation. The study successfully synthesized the desired compound in high yield, demonstrating the feasibility of the chosen synthetic route. The findings open avenues for the synthesis of other biologically active indole alkaloids, highlighting the potential for further exploration in the field of natural product synthesis.