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Key Documents

Safety Information

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:
Molecular Weight:
126.07
Beilstein:
3679436
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39021701
PubChem Substance ID:
NACRES:
NA.21

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

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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

Signal Word

Danger

Hazard Statements

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

O0376-BULK:
O0376-3KG:4548173204642
O0376-H:
O0376-10MG:4548173280080
O0376-100G:4548173204628
O0376-500G:4548173204659
O0376-1KG:4548173204635
O0376-VAR:


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Customers Also Viewed

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)
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)
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)
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)
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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