Skip to Content
Merck
All Photos(1)

Key Documents

377406

Sigma-Aldrich

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

99%

Synonym(s):

Dimethyl squarate

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
(CH3O)2C4(=O)2
CAS Number:
Molecular Weight:
142.11
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

mp

55-57 °C (lit.)

functional group

ether
ketone

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

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

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

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
Kerriann K Badal et al.
Cell reports, 26(3), 507-517 (2019-01-17)
Mechanisms that regulate the bi-directional transport of mitochondria in neurons for maintaining functional synaptic connections are poorly understood. Here, we show that in the pre-synaptic sensory neurons of the Aplysia gill withdrawal reflex, the formation of functional synapses leads to
Hydroxylamin-Derivate der Quadratsaure.
Zinner G, et al.
Arch. Pharm. (Weinheim), 318(11), 977-983 (1985)
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

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