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:

98%,99%, ^*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:

methyl 2-azido-3-(3-[1,3]dioxolan-2-ylphenyl)acrylate

methyl 2-azido-3-(3-methoxymethylphenyl)acrylate

methyl-2-azido-3-(2-fluoro-3-benzyloxyphenyl)propenoate

methyl 2-azido-3-[2-(2-methoxycarbonyl)ethylphenyl]acrylate

Refernces

• 1、 Stachel, Shawn J.,Egbertson, Melissa S.,Wai, Jenny,Machacek, Michelle,Toolan, Dawn M.,Swestock, John,Eddins, Donnie M.,Puri, Vanita,McGaughey, Georgia,Su, Hua-Poo,Perlow, Debbie,Wang, Deping,Ma, Lei,Parthasarathy, Gopal,Reid, John C.,Abeywickrema, Pravien D.,Smith, Sean M.,Uslaner, Jason M.. "Indole acids as a novel PDE2 inhibitor chemotype that demonstrate pro-cognitive activity in multiple species". . p. 1122 - 1126. Retrieved 2018.
• 2、 Zhang, Jenny Z.,Bonnitcha, Paul,Wexselblatt, Ezequiel,Klein, Alice V.,Najajreh, Yousef,Gibson, Dan,Hambley, Trevor W.. "Facile preparation of mono-, Di- and mixed-carboxylato platinum(IV) complexes for versatile anticancer prodrug design". . p. 1672 - 1676. Retrieved 2013.
• 3、 Bonacorso, Helio G.,Libero, Francieli M.,Dal Forno, Gean M.,Pittaluga, Everton P.,Back, Davi F.,H?rner, Manfredo,Martins, Marcos A.P.,Zanatta, Nilo. "New regioselective synthesis of polyfunctionalized 3-ferrocenyl-1H-pyrroles under microwave irradiation". . p. 4568 - 4573. Retrieved 2016.
• 4、 Karlsson, Staffan,Cook, Calum,Emten?s, Hans,Fan, Kenny,Gillespie, Paul,Mohamed, Mubina. "Development of a Safe Continuous Manufacturing Route to 2-(4-Isopropyl-1H-1,2,3-triazol-1-yl)acetic Acid". . p. 1668 - 1674. Retrieved 2017.
• 5、 Schmitz, Janina,Li, Tianwei,Bartz, Ulrike,Gütschow, Michael. "Cathepsin B Inhibitors: Combining Dipeptide Nitriles with an Occluding Loop Recognition Element by Click Chemistry". . p. 211 - 216. Retrieved 2016.
• 6、 Chun, Candy K. Y.,Payne, Richard J.. "Synthesis of MUC1 Peptide and Glycopeptide Dendrimers". . p. 1339 - 1343. Retrieved 2009.
• 7、 Legigan, Thibaut,Migianu-Griffoni, Evelyne,Redouane, Mohamed Abdenour,Descamps, Aurélie,Deschamp, Julia,Gager, Olivier,Monteil, Ma?lle,Barbault, Florent,Lecouvey, Marc. "Synthesis and preliminary anticancer evaluation of new triazole bisphosphonate-based isoprenoid biosynthesis inhibitors". . . Retrieved 2021/02/12.
• 8、 -. "Thienopyrrole derivative as well as preparation method and application thereof". Paragraph 0047-0050; 0062-0065; 0077-0080. . Retrieved 2020/09/08.