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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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5 G
$136.00

About This Item

Linear Formula:
(C2H5O)2C4(=O)2
CAS Number:
5231-87-8
Molecular Weight:
170.16
Beilstein/REAXYS Number:
640626
MDL number:
MFCD00001333
UNSPSC Code:
12352100
PubChem Substance ID:
24858814
NACRES:
NA.22

$136.00

In StockDetails

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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

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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.[1]

Application

3,4-Dethoxy-3-cyclobutene-1,2-dione is used as a starting material for synthesis of furanones[2] and quinones.[3] It undergoes ethoxy substitution with amines[4] and unsaturated organosilanes.[5]

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_germany

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
BCCL8393
BCCJ7595
BCCG4578
BCCD6924
BCBZ8850

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Organic Syntheses, 69, 220-220 (1990)
Journal of the Chemical Society. Perkin Transactions 1, 263-263 (1993)
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)
Sinthuja Jegatheeswaran et al.
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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
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Questions

  1. Hello, What is the MW for 3,4 Diethoxy-3-cyclobutene 1,2 Dione in Kilo Dalton's?

    1 answer

    1. The molecular weight of item 310778 is 170.16 g/mole. A dalton is a g/mole. The weight in kDa would be 0.17016.

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