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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

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...
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.
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...
The Journal of Organic Chemistry, 59, 3284-3284 (1994)

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