| Identification | More | [Name]
Dibutyl squarate | [CAS]
2892-62-8 | [Synonyms]
3,4-DIBUTOXY-3-CYCLOBUTENE-1,2-DIONE
3,4-DIBUTOXYCYCLOBUT-3-ENE-1,2-DIONE
3,4-DI-N-BUTOXY-3-CYCLOBUTEN-1,2-DIONE
3,4-DI-N-BUTOXY-3-CYCLOBUTENE-1,2-DIONE
DIBUTYL SQUARATE
SQUARIC ACID DIBUTYL ESTER
SQUARIC ACID DI-N-BUTYL ESTER
TIMTEC-BB SBB007902
Di-n-butyl squarate~Squaric acid di-n-butyl ester
3,4-DIBUTOXY-3-CYCLOBUTENE-1,2-DIONE, 98 %
di-n-butyl squarate
Squaric acid dibutyl ester, (Dibutyl squarate, 3,4-Dibutoxy-3-cyclobutene-1,2-dione)
SADBE | [EINECS(EC#)]
-0 | [Molecular Formula]
C12H18O4 | [MDL Number]
MFCD00037150 | [Molecular Weight]
226.27 | [MOL File]
2892-62-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to yellow liquid | [Boiling point ]
139 °C0.5 mm Hg(lit.)
| [density ]
1.047 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.494(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Liquid | [color ]
Clear colorless to yellow | [Water Solubility ]
INSOLUBLE | [BRN ]
1968189 | [InChI]
InChI=1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3 | [InChIKey]
XBRWELTXMQSEIN-UHFFFAOYSA-N | [SMILES]
C1(=O)C(OCCCC)=C(OCCCC)C1=O | [CAS DataBase Reference]
2892-62-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Dibutyl squarate(2892-62-8) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H317-H319-H335 | [Precautionary statements ]
P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
3
| [RTECS ]
GU1772066 | [HS Code ]
29145090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to yellow liquid | [Uses]
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. | [Uses]
Squaric acid and its derivatives (Dibutyl squarate) are used in synthesis of pharmaceutical intermediates, squarylium dyes, and photoconducting squaraines.
| [Definition]
ChEBI: A cyclic ketone and diether that is a dibutyl ether derivative of squaric acid. | [General Description]
3,4-Dibutoxy-3-cyclobutene-1,2-dione is the dialkyl ester of squaric acid. | [Synthesis]
General procedure for the synthesis of di-n-butyl squarate from squaric acid (1) (2.00 g, 17.54 mmol) and n-butanol: Squaric acid (1) was dissolved in n-butanol (50 mL) and the reaction was carried out under stirring conditions at reflux for 3 hours. After completion of the reaction, the mixture was cooled in an ice bath, followed by the addition of diethyl ether (Et2O, 50 mL). The mixture was washed sequentially with cold distilled water, cold saturated aqueous NaHCO3 solution and cold distilled water. The organic layer was separated and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give the brown oily product di-n-butyl squarate (2.92 g, 74% yield). The product was chromatographically pure and could be used in subsequent reactions without further purification. | [References]
[1] Canadian Journal of Chemistry, 1986, vol. 64, p. 2267 - 2273
[2] Bulletin de la Societe Chimique de France, 1990, # 3, p. 367 - 374
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3803 - 3814
[4] Journal of Molecular Structure, 2009, vol. 936, # 1-3, p. 239 - 249
[5] Comptes Rendus Chimie, 2012, vol. 15, # 5, p. 454 - 462 |
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J & K SCIENTIFIC LTD.
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Alfa Aesar
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Energy Chemical
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China Langchem Inc.
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