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Merck
CN

O0376

Oxalic acid dihydrate

≥99.0% (GC), ReagentPlus®

Synonym(s):

Ethanedioic acid dihydrate

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About This Item

Linear Formula:
HO2CCO2H · 2H2O
CAS Number:
Molecular Weight:
126.07
NACRES:
NA.21
PubChem Substance ID:
eCl@ss:
39021701
UNSPSC Code:
12352100
EC Number:
205-634-3
MDL number:
Beilstein/REAXYS Number:
3679436
Assay:
≥99.0% (GC)
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Product Name

Oxalic acid dihydrate, ReagentPlus®, ≥99.0% (GC)

vapor density

4.4 (vs air)

Quality Level

vapor pressure

<0.01 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99.0% (GC)

mp

104-106 °C (lit.)

functional group

carboxylic acid

SMILES string

[H]O[H].[H]O[H].OC(=O)C(O)=O

InChI

1S/C2H2O4.2H2O/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);2*1H2

InChI key

GEVPUGOOGXGPIO-UHFFFAOYSA-N

General description

Oxalic acid dihydrate (OAD) crystals are reported to be monoclinic with P21/n space group. The electron density of OAD has been obtained using X-ray diffraction studies under high resolution.

Application

Oxalic acid dihydrate may be used:
  • As a catalyst in the preparation of tetrahydroquinoline derivatives via imino Diels-Alder reaction.
  • As a homogeneous catalyst in the preparation of highly functionalized piperidines via multi-component reaction.
  • As an oxidant for the formation of triazolinediones from corresponding urazoles and bisurazoles via oxidation.
  • In the transformation of thiols to nitrosothiols by reacting with sodium nitrite.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany


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pictograms

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signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Imino Diels-Alder reactions catalyzed by oxalic acid dihydrate. Synthesis of Tetrahydroquinoline derivatives.
Nagarajan R and Perumal PT.
Synthetic Communications, 31(11), 1733-1736 (2001)
An Efficient Method for Production and Storage of Unstable S-Nitrosothiols Under Mild and Heterogeneous Condition with Sodium Nitrite and Oxalic Acid Dihydrate.
Zolfigol MA, et al.
Synthetic Communications, 29(13), 2277-2280 (1999)
One-pot five-component synthesis of highly functionalized piperidines using oxalic acid dihydrate as a homogenous catalyst.
Sajadikhah SS, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 23(5), 569-572 (2012)



Global Trade Item Number

SKUGTIN
O0376-500G04061834212584
O0376-3KG04061832750835
O0376-100G04061834212546
O0376-1KG04061826196519
O0376-10MG04061834212560