Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

530352

Sigma-Aldrich

Methyl-1H-1,2,4-triazole-3-carboxylate

98%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C4H5N3O2
CAS Number:
4928-88-5
Molecular Weight:
127.10
MDL number:
MFCD00135989
UNSPSC Code:
12352100
PubChem Substance ID:
24877742
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

196-199 °C (lit.)

SMILES string

COC(=O)c1nc[nH]n1

InChI

1S/C4H5N3O2/c1-9-4(8)3-5-2-6-7-3/h2H,1H3,(H,5,6,7)

InChI key

QMPFMODFBNEYJH-UHFFFAOYSA-N

General description

Methyl-1H-1,2,4-triazole-3-carboxylate can be synthesized from 5-amino-1,2,4-triazole-3-carboxylic acid via esterification with methanol. It is utilized as precursor for preparing the nucleoside analogue, Ribavirin. The crystal structure of methyl-1H-1,2,4-triazole-3-carboxylate has been analyzed.

Application

Methyl-1H-1,2,4-triazole-3-carboxylate (1,2,4-Triazole-3-methylcarboxylate) may be used in the preparation of 1H-1,2,4-triazole-3-carbohydrazide.
It may also be used in the synthesis of the following nucleoside analogues:
  • 1-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta-[1,3]dioxol-4-yl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester
  • methyl 4,6-O-benzylidene-2-(methyl 1H-1,2,4-triazol-1-yl-3-carboxylate)-2-deoxy-<SC>D</SC>-altrohexopyranoside
  • 1,5-anhydro-4,6-O-benzylidene-2-(methyl 1H-1,2,4-triazol-1-yl-3-carboxylate)-2-deoxy-<SC>D</SC>-altro-hexitol

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Jong Hyun Cho et al.
Journal of medicinal chemistry, 49(3), 1140-1148 (2006-02-03)
A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by
Dinuclear, Tetranuclear and Chain (MnII, CoII) Complexes of Multifunctional Hydrazone Ligands?Structural and Magnetic Studies.
Bettle PJ, et al.
European Journal of Inorganic Chemistry, 2011(32), 5036-5042 (2011)
Arthur Van Aerschot et al.
Antiviral chemistry & chemotherapy, 14(1), 23-30 (2003-06-07)
Current standard therapy for the treatment of chronic infections with hepatitis C virus consists of combination therapy with (pegylated) interferon-alpha and ribavirin. 1,5-Anhydrohexitol nucleoside analogues are constrained congeners known to mimic the ribonucleoside conformation. Within this series some analogues are
Methyl 1H-1,2,4-triazole-3-carboxylate.
Guo XH and Wang QX.
Acta Crystallographica Section E, Structure Reports Online, 61(10), o3217-o3218 (2005)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service