- Dimethyl squarate
-
- $2.00 / 100KG
-
2025-10-13
- CAS:5222-73-1
- Min. Order: 0.1KG
- Purity: 99%
- Supply Ability: g-kg-tons
|
| | 3,4-Dimethoxy-3-cyclobutene-1,2-dione Basic information |
| Product Name: | 3,4-Dimethoxy-3-cyclobutene-1,2-dione | | Synonyms: | DIMETHYL SQUARATE;3-Cyclobutene-1,2-dione,3,4-dimethoxy-;Squaric acid dimethyl e;diMethoxycyclobut-3-ene-1,2-dione;3,4-Dimethoxycyclobut-3-ene-1,2-dione 98%;Dimethyl squarate, 1,2-Dimethoxy-3,4-dioxocyclobut-1-ene;Dimethyl squarate 3,4-Dimethoxy-3-cyclobutene-1,2-dione;SQUARIC ACID DIMETHYL ESTER | | CAS: | 5222-73-1 | | MF: | C6H6O4 | | MW: | 142.11 | | EINECS: | 627-380-6 | | Product Categories: | Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;Ring Systems;Aluminium foil bag/Fluoride bottle or on your request;Pyrimidines | | Mol File: | 5222-73-1.mol |  |
| | 3,4-Dimethoxy-3-cyclobutene-1,2-dione Chemical Properties |
| Melting point | 55-57 °C (lit.) | | Boiling point | 219.65°C (rough estimate) | | density | 1.3863 (rough estimate) | | refractive index | 1.5800 (estimate) | | storage temp. | 2-8°C | | solubility | DMSO, Methanol (Slightly) | | form | Solid | | color | Off-White to Pale Brown | | Water Solubility | Very soluble in water. | | InChI | 1S/C6H6O4/c1-9-5-3(7)4(8)6(5)10-2/h1-2H3 | | InChIKey | SZBNZTGCAMLMJY-UHFFFAOYSA-N | | SMILES | COC1=C(OC)C(=O)C1=O | | CAS DataBase Reference | 5222-73-1(CAS DataBase Reference) | | NIST Chemistry Reference | 3,4-Dimethoxy-3-cyclobutene-1,2-dione(5222-73-1) |
| Risk Statements | 42/43 | | Safety Statements | 22-24/25-26-36/37/39 | | WGK Germany | 3 | | HS Code | 29145090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Resp. Sens. 1
Skin Sens. 1 |
| | 3,4-Dimethoxy-3-cyclobutene-1,2-dione Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | 3,4-Dimethoxy-3-cyclobutene-1,2-dione (Dimethyl squarate) finds it uses in the synthesis of chiral squaramides, highly enantioselective catalyst for the Friedel-Crafts reactions of indoles, 3-(hydroxyamino)-4-methoxy-3-cyclobutene-1,2-dione, squarate derivatives of the O-SP-core antigens, methyl squarate derivative of the Ogawa O-SP-core antigen, o-quinodimethanes, benzocyclobutenes, quinones. It is employed as a starting material in the preparation of o-quinodimethanes, benzocyclobutenes, and quinones. | | General Description | 3,4-Dimethoxy-3-cyclobutene-1,2-dione (Dimethyl squarate) is a cyclobutene derivative. It reacts with hydroxylamine derivatives to afford 3-hydroxyamino-4-methoxy-3-cyclobutene-1,2-diones. | | Synthesis | 3,4-Dimethoxy-3-cyclobutene-1,2-dione (compound 30) was synthesized using a modified Liu et al. method [7]. The procedure was as follows: 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid, 2.053 g, 18 mmol) was dissolved in anhydrous methanol (18 mL), followed by addition of trimethyl orthoformate (4 mL, 36.5 mmol) to the solution. The reaction mixture was refluxed at 56 °C for 24 hours. Upon completion of the reaction, the crude product was concentrated under reduced pressure. The resulting light yellow solid was dissolved in dichloromethane and purified by silica gel column chromatography (eluent ratio of ethyl acetate: hexane = 1:2) to afford 3,4-dimethoxycyclobut-3-ene-1,2-dione (2.29 g, 89.4% yield) as a final white solid. The melting point of the compound is 55-57 °C (literature value 56-58 °C) [7,8]. NMR hydrogen spectrum (300 MHz, CD2Cl2) δ 4.34 (6H, s, OCH3); NMR carbon spectrum (75 MHz, CD3OD) δ 189.35 (C2, C=O), 189.35 (C1, C=O), 184.35 (C3), 184.35 (C4), 60.29 (OCH3), 60.29 ( OCH3). Low resolution mass spectra (EI): m/z 142.03 (100%), 114.03 (18%), 99.01 (16%), 86.01 (54%), 67.99 (8%), 56.25 (7%). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 282 - 287
[2] Organic Syntheses, 1999, vol. 76, p. 189 - 189
[3] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13698 - 13705
[4] Chemistry - A European Journal, 2017, vol. 23, # 47, p. 11234 - 11238
[5] Chemical Communications, 2018, vol. 54, # 26, p. 3231 - 3234 |
| | 3,4-Dimethoxy-3-cyclobutene-1,2-dione Preparation Products And Raw materials |
|