377406
3,4-Dimethoxy-3-cyclobutene-1,2-dione
99%
Synonym(s):
Dimethyl squarate
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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
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Assay
99%
form
solid
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
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
Certificates of Analysis (COA)
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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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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
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