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Merck
CN

310778

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:
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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InChI

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

SMILES string

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

InChI key

DFSFLZCLKYZYRD-UHFFFAOYSA-N

assay

98%

form

liquid

Quality Level

100

bp

95 °C/0.1 mmHg (lit.)

density

1.15 g/mL at 25 °C (lit.)

functional group

ether, ketone

Related Categories

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
GHS08,GHS07

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3558
BCCL8393
BCCJ7595
BCCG4578
BCCD6924

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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)
W A Kinney et al.
Journal of medicinal chemistry, 35(25), 4720-4726 (1992-12-21)
In this report, a novel bioisostere of the alpha-amino acid, 3,4-diamino-3-cyclobutene-1,2-dione, has been incorporated into a series of compounds which are NMDA antagonists. These compounds, which are achiral and easily prepared, demonstrated good affinity at the NMDA receptor by their
Sinthuja Jegatheeswaran et al.
Vaccines, 8(3) (2020-09-23)
The carbohydrate antigen dimeric Lewis X (DimLex), which accumulates in colonic and liver adenocarcinomas, is a valuable target to develop anti-cancer therapeutics. Using the native DimLex antigen as a vaccine would elicit an autoimmune response against the Lex antigen found
Organic Syntheses, 69, 220-220 (1990)
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