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O0376

Sigma-Aldrich

Oxalic acid dihydrate

ReagentPlus®, ≥99.0% (GC)

Synonym(s):

Ethanedioic acid dihydrate

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About This Item

Linear Formula:
HO2CCO2H · 2H2O
CAS Number:
6153-56-6
Molecular Weight:
126.07
Beilstein:
3679436
EC Number:
205-634-3
MDL number:
MFCD00149102
UNSPSC Code:
12352100
eCl@ss:
39021701
PubChem Substance ID:
57654475
NACRES:
NA.21

vapor density

4.4 (vs air)

Quality Level

200

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

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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

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312,H318

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000385511
0000378527
0000357424
0000357425
0000323386

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Charge density studies on small organic molecules around 20 K: oxalic acid dihydrate at 15 K and acetamide at 23 K.
Zobel D, et al.
Acta Crystallographica Section B, Structural Science, 48(6), 837-848 (1992)
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)
A Convenient Method for the Oxidation of Urazoles to Their Corresponding Triazolinediones Under Mild and Heterogeneous Conditions with Sodium Nitrite and Oxalic Dihydrate.
Zolfigolo MA and Mallakpour SE.
Synthetic Communications, 29(22), 4061-4069 (1999)
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)
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