377406

Sigma-Aldrich

3,4-Dimethoxy-3-cyclobutene-1,2-dione

99%

Synonym(s):
Dimethyl squarate
Linear Formula:
(CH3O)2C4(=O)2
CAS Number:
Molecular Weight:
142.11
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

mp

55-57 °C (lit.)

storage temp.

2-8°C

SMILES string

COC1=C(OC)C(=O)C1=O

InChI

1S/C6H6O4/c1-9-5-3(7)4(8)6(5)10-2/h1-2H3

InChI key

SZBNZTGCAMLMJY-UHFFFAOYSA-N

Related Categories

General description

3,4-Dimethoxy-3-cyclobutene-1,2-dione (Dimethyl squarate) is a cyclobutene derivative. It reacts with hydroxylamine derivatives to afford 3-hydroxyamino-4-methoxy-3-cyclobutene-1,2-diones.

Application

3,4-Dimethoxy-3-cyclobutene-1,2-dione (Dimethyl squarate) may be used in the synthesis of the following compounds:
  • chiral squaramides, highly enantioselective catalyst for the Friedel-Crafts reactions of indoles
  • 3-(hydroxyamino)-4-methoxy-3-cyclobutene-1,2-dione
  • squarate derivatives of the O-SP-core antigens
  • methyl squarate derivative of the Ogawa O-SP-core antigen
  • o-quinodimethanes
  • benzocyclobutenes
  • quinones

Packaging

1, 5 g in glass bottle

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

hazcat

Resp. Sens. 1 - Skin Sens. 1

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Hydroxylamin-Derivate der Quadratsaure.
Zinner G, et al.
Arch. Pharm. (Weinheim), 318(11), 977-983 (1985)
Peng Xu et al.
Bioconjugate chemistry, 22(10), 2179-2185 (2011-09-09)
Bacterial O-SP-core antigens can be conjugated to proteins in the same, simple way as synthetic, linker-equipped carbohydrates by applying squaric acid chemistry. Introduction of spacers (linkers) to either O-SP-core antigens or protein carriers, which is involved in commonly applied protocols...
The Journal of Organic Chemistry, 57, 6896-6896 (1992)
Tetrahedron Letters, 34, 6177-6177 (1993)
Mohammad Murshid Alam et al.
PLoS neglected tropical diseases, 8(2), e2683-e2683 (2014-02-12)
Protective immunity against cholera is serogroup specific. Serogroup specificity in Vibrio cholerae is determined by the O-specific polysaccharide (OSP) of lipopolysaccharide (LPS). Generally, polysaccharides are poorly immunogenic, especially in young children. Here we report the evaluation in mice of a...

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