| Identification | More | [Name]
Diethyl squarate | [CAS]
5231-87-8 | [Synonyms]
1,2-DIETHOXYCYCLOBUTENEDIONE
3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE
3,4-DIETHOXYCYCLOBUT-3-ENE-1,2-DIONE
DIETHYL SQUARATE
DIETHYL SUQUARATE
SQUARIC ACID DIETHYL ESTER
SUQUARIC ACID DIETHYL ESTER
TIMTEC-BB SBB008498
3-Cyclobutene-1,2-dione, 3,4-diethoxy-
3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE, 98 %
DiethylSquarate98%
3,4-DIETHOXYCYCLOBUTANE-1,2-DIONE
Diethyl squarate, Squaric acid diethyl ester
SQUARIC ACID DIETHYL ESTER,(DIETHYL SQUARATE, 3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE)
DIETHOXYCYCLOBUTENEDIONE
3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE 98%
SQUARICACIDDIETHYLESTER/3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE
3,4-Diethoxy-3-cyclobuten-1,2-dion
Diethyl quadratate | [Molecular Formula]
C8H10O4 | [MDL Number]
MFCD00001333 | [Molecular Weight]
170.16 | [MOL File]
5231-87-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to light brownish liquid | [Melting point ]
13-18 °C | [Boiling point ]
95 °C0.1 mm Hg(lit.) | [density ]
1.15 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.509(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [color ]
Clear yellow to light brownish | [Water Solubility ]
insoluble | [Usage]
Intermediate for pharma products, for photochemicals used in the dry-view process, in synthesis of photosensitive squaraine dyes (eg. laser dyes used in CD-Rom) and as intermediate for functional polymers. | [BRN ]
640626 | [InChIKey]
DFSFLZCLKYZYRD-UHFFFAOYSA-N | [CAS DataBase Reference]
5231-87-8(CAS DataBase Reference) | [NIST Chemistry Reference]
3,4-Diethoxy-3-cyclobutene-1,2-dione(5231-87-8) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S7:Keep container tightly closed .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S24:Avoid contact with skin .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [WGK Germany ]
3
| [RTECS ]
GU1772466 | [F ]
10 | [Hazard Note ]
Irritant | [HS Code ]
29145090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear yellow to light brownish liquid | [Uses]
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. | [Uses]
Diethyl squarate is an intermediate for pharma products, for photochemicals used in the dry-view process, in synthesis of photosensitive squaraine dyes (eg. laser dyes used in CD-Rom) and as intermediate for functional polymers.
| [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. | [Synthesis]
1. Squaric acid (1.0023 g) was dissolved in 30 mL of anhydrous ethanol and heated to reflux overnight. After the reaction was completed, the reaction solution was concentrated and purified by fast column chromatography to give 0.7430 g of diethyl ester of squaric acid in 50% yield.
2. The resulting diethyl (ethyl) squarate, 2-aminopyridine (100 mg, 0.588 mmol) and triethylamine (10 drops) were dissolved in dichloromethane (10 mL) and stirred at room temperature overnight. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified by fast column chromatography (petroleum ether/ethyl acetate, 2:1) to afford compound 6 as a white solid in 73% yield.
3. The NMR data of compound 6 were as follows: 1H NMR (400 MHz, acetone-d6) δ 10.26 (s, 1H), 8.50-8.29 (m, 1H), 7.98-7.78 (m, 1H), 7.68 (d, J = 8.3 Hz, 1H), 7.14 (dd, J = 6.9, 5.3 Hz, 1H), 4.85 (q, J = 7.1 Hz, 2H), 1.48 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, acetone-d6) δ 186.42, 180.83, 170.33, 166.86, 152.22, 149.33, 139.43, 120.17, 113.63, 70.65, 16.06. | [References]
[1] Journal of Materials Chemistry A, 2015, vol. 3, # 6, p. 2883 - 2894
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 22, p. 6181 - 6186
[3] Angew. Chem., 2017, vol. 129, # 22, p. 6277 - 6282,6
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 2, p. 263 - 272
[5] Chemical Communications, 2013, vol. 49, # 89, p. 10465 - 10467 |
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