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

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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)

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Safety

Risk Statements: 42/43
Safety Statements: 22-24/25-26-36/37/39
WGK Germany: 3
HS Code: 29145090

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 377406
Product name: 3,4-Dimethoxy-3-cyclobutene-1,2-dione
Purity: 99%
Packaging: 1g
Price: $28.3
Updated: 2025/07/31

Sigma-Aldrich

Product number: 377406
Product name: 3,4-Dimethoxy-3-cyclobutene-1,2-dione
Purity: 99%
Packaging: 5g
Price: $107
Updated: 2025/07/31

TCI Chemical

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

TCI Chemical

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

TCI Chemical

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

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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

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3,4-Dimethoxy-3-cyclobutene-1,2-dione Suppliers

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View Lastest Price from 3,4-Dimethoxy-3-cyclobutene-1,2-dione manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

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

Henan Aochuang Chemical Co.,Ltd.

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

Career Henan Chemical Co

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

5222-73-1, 3,4-Dimethoxy-3-cyclobutene-1,2-dioneRelated Search:

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DIMETHYL SQUARATE

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3,4-Dimethoxy-3-cyclobutene-1,2-dione&gt

5222-73-1

CH3O2C4O2

C6H6O4

Ketones

Organic Building Blocks

C3 to C6

Simple 4-Membered Ring Compounds

Cyclobutanes & Cyclobutenes

Carbonyl Compounds

Building Blocks

Cyclobutanes & Cyclobutenes

Simple 4-Membered Ring Compounds

Ring Systems

Aluminium foil bag/Fluoride bottle or on your request

Pyrimidines