738859
Methyl 2-azidoacetate
97%
Synonym(s):
Methyl azidoacetate
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About This Item
Empirical Formula (Hill Notation):
C3H5N3O2
CAS Number:
Molecular Weight:
115.09
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
liquid
refractive index
n20/D 1.440
density
1.182 g/mL at 25 °C
SMILES string
COC(=O)CN=[N+]=[N-]
InChI
1S/C3H5N3O2/c1-8-3(7)2-5-6-4/h2H2,1H3
InChI key
RXYCUKSOYJWGPE-UHFFFAOYSA-N
Application
- 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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
120.0 °F
Flash Point(C)
48.9 °C
Regulatory Information
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Highly fluorescent pyreno [2, 1-b] pyrroles: First syntheses, crystal structure, and intriguing photophysical properties.
Selvi S, et al.
The Journal of Organic Chemistry, 69(20), 6674-6678 (2004)
The hemetsberger-knittel synthesis of substituted 5-, 6-, and 7-azaindoles.
Roy P J, et al.
Synthesis, 2005(16), 2751-2757 (2005)
A Metal?Free Three?Component Reaction for the Regioselective Synthesis of 1, 4, 5?Trisubstituted 1, 2, 3?Triazoles.
Thomas J, et al.
Angewandte Chemie (International Edition in English), 53(38), 10155-10159 (2014)
Biological evaluation of new largazole analogues: alteration of macrocyclic scaffold with click chemistry.
Li X, et al.
ACS Medicinal Chemistry Letters, 4(1), 132-136 (2012)
Small Molecule Near-Infrared Boron Dipyrromethene Donors for Organic Tandem Solar Cells.
Li T Y, et al.
Journal of the American Chemical Society, 139(39), 13636-13639 (2017)
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