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310778

Sigma-Aldrich

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

98%

Synonym(s):

Diethyl squarate, Squaric acid diethyl ester

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About This Item

Linear Formula:
(C2H5O)2C4(=O)2
CAS Number:
Molecular Weight:
170.16
Beilstein:
640626
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.509 (lit.)

bp

95 °C/0.1 mmHg (lit.)

density

1.15 g/mL at 25 °C (lit.)

functional group

ether

SMILES string

CCOC1=C(OCC)C(=O)C1=O

InChI

1S/C8H10O4/c1-3-11-7-5(9)6(10)8(7)12-4-2/h3-4H2,1-2H3

InChI key

DFSFLZCLKYZYRD-UHFFFAOYSA-N

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General description

The reaction of 3,4-diethoxy-3-cyclobutene-1,2-dione (squaric acid diethyl ester) with glycosylamines (formed by reducing oligosaccharides) was studied. The derivatives formed were linked to amino-functionalized lipids, solids or proteins.

Application

3,4-Dethoxy-3-cyclobutene-1,2-dione is used as a starting material for synthesis of furanones and quinones. It undergoes ethoxy substitution with amines and unsaturated organosilanes.

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Carbohydrate research, 319(1-4), 80-91 (1999-10-16)
Reducing oligosaccharides were converted into their corresponding glycosylamines, and these were reacted with 3,4-diethoxy-3-cyclobuten-1,2-dione (squaric acid diethyl ester). The resulting derivatives could be linked to amino-functionalized lipids, solids, or proteins. Treatment of the obtained lipid or solid conjugates with aqueous
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