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377406
3,4-Dimethoxy-3-cyclobutene-1,2-dione
99%
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Synonym(s):
Dimethyl squarate
Linear Formula:
(CH3O)2C4(=O)2
CAS Number:
Molecular Weight:
142.11
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Personal Protective Equipment
RIDADR
NONH for all modes of transport
WGK Germany
WGK 3
Certificate of Analysis
Certificate of Origin
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...
Hydroxylamin-Derivate der Quadratsaure.
Zinner G, et al.
Arch. Pharm. (Weinheim), 318(11), 977-983 (1985)
The Journal of Organic Chemistry, 59, 3284-3284 (1994)
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...
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.
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