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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

Quality Level

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.)

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

Certificates of Analysis (COA)

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O Blixt et al.
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
The Journal of Organic Chemistry, 59, 4707-4707 (1994)
Organic Syntheses, 69, 220-220 (1990)
Journal of the Chemical Society. Perkin Transactions 1, 263-263 (1993)
E F Sherertz et al.
Archives of dermatological research, 280(1), 57-60 (1988-01-01)
Squaric acid diethylester and squaric acid dibutylester have been used in contact sensitization therapy of alopecia areata. This study investigated the application of these esters or squaric acid alone to hairless mouse and human skin in vitro to determine squaric

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