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MilliporeSigma

377406

Sigma-Aldrich

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

99%

Synonym(s):

Dimethyl squarate

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1 G
$28.30
5 G
$107.00

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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$28.30


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Quality Level

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

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This Item
310778339792123447
assay

99%

assay

98%

assay

98%

assay

≥99.0% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

form

solid

form

liquid

form

liquid

form

solid

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

mp

55-57 °C (lit.)

mp

-

mp

-

mp

>300 °C (lit.)

functional group

ether

functional group

ether, ketone

functional group

ether, ketone

functional group

-

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.[1]

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[2]
  • 3-(hydroxyamino)-4-methoxy-3-cyclobutene-1,2-dione[3]
  • squarate derivatives of the O-SP-core antigens[4]
  • methyl squarate derivative of the Ogawa O-SP-core antigen[5]
  • o-quinodimethanes[6]
  • benzocyclobutenes[6]
  • quinones[7][8]

pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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