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Merck

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:
6153-56-6
Molecular Weight:
126.07
NACRES:
NA.21
PubChem Substance ID:
57654475
eCl@ss:
39021701
UNSPSC Code:
12352100
EC Number:
205-634-3
MDL number:
MFCD00149102
Beilstein/REAXYS Number:
3679436
Assay:
≥99.0% (GC)

Key Documents

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Product Name

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

InChI key

GEVPUGOOGXGPIO-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor density

4.4 (vs air)

vapor pressure

<0.01 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99.0% (GC)

mp

104-106 °C (lit.)

functional group

carboxylic acid

Quality Level

200

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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

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

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.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCK3069
SLCH1661
SLCG2480
SLCF1178
SLCD3527

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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)
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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