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310778

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

Name: 3,4-Diethoxy-3-cyclobutene-1,2-dione
Brand: ALDRICH

98%

Synonym(s):

Diethyl squarate, Squaric acid diethyl ester

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About This Item

Linear Formula:

(C₂H₅O)₂C₄(=O)₂

CAS Number:

5231-87-8

Molecular Weight:

170.16

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24858814

MDL number:

MFCD00001333

Beilstein/REAXYS Number:

640626

Assay:

98%

Form:

liquid

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Properties

Quality Level

100

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, ketone

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

Description

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

GHS08,GHS07

signalword

Danger

hcodes

H315,H317,H319,H334,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Enzymatic glycosylation of reducing oligosaccharides linked to a solid phase or a lipid via a cleavable squarate linker.

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)

Journal of the Chemical Society. Perkin Transactions 1, 263-263 (1993)

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Global Trade Item Number

SKU	GTIN
310778-5G	04061826677797