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377406 Sigma-Aldrich

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

99%

Synonym: Dimethyl squarate

  • CAS Number 5222-73-1

  • Linear Formula (CH3O)2C4(=O)2

  • Molecular Weight 142.11

  •  MDL number MFCD00101316

  •  PubChem Substance ID 24863502

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C3 to C6, Carbonyl Compounds, Chemical Synthesis, Ketones,
Quality Level   100
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

Description

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

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Protocols & Articles
Peer-Reviewed Papers
15

References

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