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738859

Sigma-Aldrich

Methyl 2-azidoacetate

97%

Synonym(s):

Methyl azidoacetate

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About This Item

Empirical Formula (Hill Notation):
C3H5N3O2
CAS Number:
1816-92-8
Molecular Weight:
115.09
MDL number:
MFCD01311034
UNSPSC Code:
12352100
PubChem Substance ID:
329765305
NACRES:
NA.22

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.[1] Some of the examples include the synthesis of coumarin-triazole derivatives as potential antiplasmodial agents[2] and macrocyclic triazole containing largazole analogs as histone deacetylases-1 (HDAC1) inhibitors.[3]
  • It can be used to synthesize various pyrrole derivatives by Knoevenagel condensation[4] as in the synthesis of near-infrared boron dipyrromethene (BODIPY) donors for organic tandem solar cells.[5]
  • It can also be used in Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles.[6]
  • Synthesis of highly fluorescent pyreno[2,1-b]pyrroles using methyl 2-azidoacetate as one of the reagents.[7]

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

120.0 °F

flash_point_c

48.9 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF8212
MKCC7834
MKCB0849V
MKBW9163V
MKBV5810V

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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)
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)
In vitro antiplasmodial efficacy of synthetic coumarin-triazole analogs.
Yadav N, et al.
European Journal of Medicinal Chemistry (2018)
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)
Transition metal-catalyzed synthesis of pyrroles from dienyl azides.
Dong H, et al.
Organic Letters, 9(25), 5191-5194 (2007)
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