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339792

Sigma-Aldrich

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

98%

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Synonym(s):
Dibutyl squarate
Linear Formula:
[CH3(CH2)3O]2C4(=O)2
CAS Number:
Molecular Weight:
226.27
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

SMILES string

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

InChI

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

InChI key

XBRWELTXMQSEIN-UHFFFAOYSA-N

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Treatment of alopecia areata in children.
Niyati Mukherjee et al.
Pediatric annals, 38(7), 388-395 (2009-08-19)
Alopecia areata triggered or exacerbated by swine flu virus infection.
Taisuke Ito et al.
The Journal of dermatology, 39(10), 863-864 (2011-12-07)
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)
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

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