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Merck
CN

339792

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

98%

Synonym(s):

Dibutyl squarate

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About This Item

Linear Formula:
[CH3(CH2)3O]2C4(=O)2
CAS Number:
2892-62-8
Molecular Weight:
226.27
NACRES:
NA.22
PubChem Substance ID:
24860681
UNSPSC Code:
12352100
MDL number:
MFCD00037150
Assay:
98%
Form:
liquid

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InChI

1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3

SMILES string

CCCCOC1=C(OCCCC)C(=O)C1=O

InChI key

XBRWELTXMQSEIN-UHFFFAOYSA-N

assay

98%

form

liquid

refractive index

n20/D 1.494 (lit.)

bp

139 °C/0.5 mmHg (lit.)

density

1.047 g/mL at 25 °C (lit.)

functional group

ether, ketone

Quality Level

200

Related Categories

General description

3,4-Dibutoxy-3-cyclobutene-1,2-dione is the dialkyl ester of squaric acid.

Application

3,4-Dibutoxy-3-cyclobutene-1,2-dione was used in the synthesis of novel semisquarylium dye, useful for highly selective Hg2+ sensing in aqueous media. It was also employed in the synthesis of 3-butoxy-4-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenemethyl)-3-cyclobutene-1,2-dione, intermediate for the synthesis of squaryl dyes.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ1016
MKCV9981
MKCT1801
MKCQ1096
MKCK8731

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Yayoi Shimaoka et al.
The Journal of dermatology, 35(3), 151-153 (2008-03-19)
A 57-year-old Japanese male patient with an 18-year history of discoid lupus erythematosus (DLE) presented with alopecia on his scalp, and was clinically diagnosed to have alopecia areata. He was started on topical immunotherapy with squaric acid dibutylester (SADBE) for
Treatment of alopecia areata in children.
Niyati Mukherjee et al.
Pediatric annals, 38(7), 388-395 (2009-08-19)
Shigeki Inui et al.
The Journal of dermatology, 36(6), 323-327 (2009-06-09)
To study the effect of fexofenadine on extensive alopecia areata (AA), we evaluated retrospectively 121 patients with AA having alopecia in more than 50% of the scalp and followed them for at least 6 months. Patients were treated by immunotherapy
Synthesis of novel squaraine dyes and their intermediates.
Tatarets AL, et al.
Dyes and Pigments, 64(2), 125-134 (2005)
Kazumasa Morita et al.
The Journal of dermatology, 29(10), 661-664 (2002-11-16)
Topical immunotherapy is effective for severe alopecia areata. However, there are patients with alopecia areata refractory to topical immunotherapy alone. We tried SADBE (squaric acid dibutylester) topical immunotherapy combined with topical dry ice cryotherapy, carpronium chloride (a parasympathetic nerve stimulant)
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