All Photos(1)

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

Hazard Classifications

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)
Yong Qian et al.
Chemical communications (Cambridge, England), 46(17), 3004-3006 (2010-04-14)
Chiral squaramides are highly enantioselective catalysts for Friedel-Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85-96% yields and 84-96% ees.
Tetrahedron Letters, 34, 6177-6177 (1993)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service