3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Product Name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- CAS No.
- 5222-73-1
- Chemical Name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Synonyms
- 3,4-DIMETHOXYCYCLOBUT-3-ENE-1,2-DIONE;DIMETHYL SQUARATE;diMethoxycyclobut-3-ene-1,2-dione;3,4-Dimethoxy-3-cycl;Squaric acid dimethyl e;SQUARIC ACID DIMETHYL ESTER;3,4-DIMETHOXYCYCLOBUTANE-1,2-DIONE;1,2-Dimethoxycyclobutene-3,4-dione;3,4-DIMETHOXY-3-CYCLOBUTENE-1,2-DIONE;1,2-Dimethoxy-1-cyclobutene-3,4-dione
- CBNumber
- CB3165164
- Molecular Formula
- C6H6O4
- Formula Weight
- 142.11
- MOL File
- 5222-73-1.mol
3,4-Dimethoxy-3-cyclobutene-1,2-dione Property
- 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.
- InChIKey
- SZBNZTGCAMLMJY-UHFFFAOYSA-N
- CAS DataBase Reference
- 5222-73-1(CAS DataBase Reference)
- NIST Chemistry Reference
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione(5222-73-1)
Safety
- Risk Statements
- 42/43
- Safety Statements
- 22-24/25-26-36/37/39
- WGK Germany
- 3
- HS Code
- 29145090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H317May cause an allergic skin reaction
H334May cause allergy or asthma symptoms or breathing difficulties if inhaled
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- 377406
- Product name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Purity
- 99%
- Packaging
- 1g
- Price
- $28.3
- Updated
- 2025/07/31
- Product number
- 377406
- Product name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Purity
- 99%
- Packaging
- 5g
- Price
- $107
- Updated
- 2025/07/31
- Product number
- D2099
- Product name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $44
- Updated
- 2025/07/31
- Product number
- D2099
- Product name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $134
- Updated
- 2025/07/31
- Product number
- D2099
- Product name
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $459
- Updated
- 2025/07/31
3,4-Dimethoxy-3-cyclobutene-1,2-dione Chemical Properties,Usage,Production
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
2892-51-5
149-73-5
5222-73-1
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
Raw materials
Preparation Products
3,4-Dimethoxy-3-cyclobutene-1,2-dione Suppliers
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- Country
- Belgium
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View Lastest Price from 3,4-Dimethoxy-3-cyclobutene-1,2-dione manufacturers
- Product
- Dimethyl squarate 5222-73-1
- Price
- US $2.00-5.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons
- Release date
- 2025-07-10
- Product
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione 5222-73-1
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-19
- Product
- 3,4-Dimethoxy-3-cyclobutene-1,2-dione 5222-73-1
- Price
- US $7.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2018-12-14