3-Oxocyclobutanecarboxylic acid

Iupac Name：3-oxocyclobutane-1-carboxylic acid

Molecular Weight：114.1

Modify Date.: 2022-11-22 17:10

Introduction:

3-oxocyclobutanyl carboxylic acid is a colorless liquid, which can be used in scientific research reagent products, as well as pharmaceutical intermediates and organic synthesis intermediates.

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1. Names and Identifiers

1.1 Name: 3-Oxocyclobutanecarboxylic acid
1.2 Synonyms: (3-oxocyclobutyl)carboxylic acid 3-Oxocyclobutanecarboxyli... 3-OXO-CYCLOBUTANECARBOXYLIC ACID 3-oxocyclobutanecarboxylic acid(SALTDATA: FREE) 3-Oxycyclobutanecarboxylic acid IFLAB-BB F2124-0041

1.3 CAS No.: 23761-23-1

1.4 CID: 4913358

1.5 EINECS(EC#): 639-432-5

1.6 Molecular Formula: C5H6O3 (isomer)

1.7 Inchi: InChI=1S/C5H6O3/c6-4-1-3(2-4)5(7)8/h3H,1-2H2,(H,7,8)

1.8 InChkey: IENOFRJPUPTEMI-UHFFFAOYSA-N

1.9 Canonical Smiles: C1C(CC1=O)C(=O)O

1.10 Isomers Smiles: C1C(CC1=O)C(=O)O

2. Properties

2.1 Density: 1.431

2.1 Melting point: 147°C

2.1 Boiling point: 296℃

2.1 Refractive index: 1.531

2.1 Flash Point: 147℃

2.1 Precise Quality: 114.03200

2.1 PSA: 54.37000

2.1 logP: 0.05010

2.1 Appearance: Off-white Solid

2.2 Storage: Room temperature.

2.3 Chemical Properties: White solid

2.4 Color/Form: White to Yellow Solid

2.5 pKa: 4.35±0.20(Predicted)

2.6 Water Solubility: Slightly soluble in water.

2.7 StorageTemp: Room temperature.

3. Use and Manufacturing

3.1 Methods of Manufacturing: Product from Step A (4. 8G, 17 mmol) was stirred with 20percent HC1 (20 ML) at reflux for 60 h before being cooled to room temperature. Ether was added and the solution was vigorously stirred for 24 hours. The ether layer was removed and the aqueous layer was extracted with ether (3x). The combined organic layers were dried over anhydrous MGS04 and concentrated in vacuo to yield Intermediate 1 (1.84g, 96.8percent). The crude product was used on next step. NMR (400 MHz, CDC13) 8 3.52-3. 26 (m, 5H).Diisopropyl 3, 3-dimethoxycyclobutane-1, 1-dicarboxylate (31 g, 0.11 mol) was heated with 78 mL of 20percent HCl at reflux for 60 h. (2.5 g) of 3, 3-dimethoxycyclobutane-1, 1-dicarboxylic acid diisopropyl ester was added to a solution of 2.5 equivalents of KOH (3.0 g) in (15 mL) and stirred at room temperature for 4 hours Rear, 20 mL of concentrated hydrochloric acid was slowly added (the concentration of hydrochloric acid in the reaction solution was about 25percent), heated to reflux, reacted for 24 hours, and the reaction was completed.Cooled to room temperature and extracted with ethyl acetate three times. The organic phase was dried over anhydrous sodium sulfate and the organic solvent was distilled off under reduced pressure. The crude product was recrystallized to obtain 0.79 g of white crystals in 80percent yield.Compound 29.3 (150 g, 0.52 mol) was added to a solutionof 10 M HCI (400 ml), andthe reaction mixture was heated to reflux for 60 hr.The reactionmixture was cooledto rt, extracted with Et20 (10 x 1 L) and the combinedorganic layers were dried, filteredand concentrated under reduced pressureto give compound 29.4 (65 g) as a yellow oil, which was5 carriedthrough to the next step withoutfurther purification..3, 3-Dimethoxy-cyclobutane-1, 1-dicarboxylic acid diethyl ester (4.72 g, 18.15 mmol) was stirred with 20percent hydrochloric acid (50 ml) at reflux for 50 h. After cooling, the solution was continuously extracted with ether for 20 h. The ether was removed at reduced pressure and the residue was treated with hexanes and cooled. Filtration and wash with hexanes afforded 3-oxo-cyclobutanecarboxylic acid (1.4 g, 70percent) as a brown solid.

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: 22

4.1 Safety Statements: 26-37-60

4.1 Hazard Declaration: H302

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501

4.1 Specification: ?3-Oxocyclobutanecarboxylic acid , its cas register number is 23761-23-1. It also can be called?(3-Oxocyclobutyl)carboxylic acid ; 3-Oxo-cyclobutanecarboxylic acid .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

23761-23-1Total: 4 Synthesis Route

15760-35-7 50 Suppliers

23761-23-1 239 Suppliers

Literatures:
WO2012/58187 A1, ; WO 2012/058187 A1
Yield: null

15760-36-8 27 Suppliers

23761-23-1 239 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 80, p. 5837,5839
Yield: null

115118-68-8 31 Suppliers

23761-23-1 239 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 53, # 16 p. 3841 - 3843
Yield: ~97%

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7. Precursor and Product

precursor:

115118-67-7

15760-35-7

115118-68-8

15760-36-8

product :

154748-63-7

545882-60-8

1234616-26-2

107496-54-8

175021-11-1

183616-18-4

130369-36-7

87121-89-9

98231-07-3

1186202-25-4

4934-99-0

695-95-4

935273-86-2

23761-24-2

145549-76-4

480449-99-8

View all

8. Other Information

8.0 Storage Conditions: Product from Step A (4. 8G, 17 mmol) was stirred with 20percent HC1 (20 ML) at reflux for 60 h before being cooled to room temperature. Ether was added and the solution was vigorously stirred for 24 hours. The ether layer was removed and the aqueous layer was extracted with ether (3x). The combined organic layers were dried over anhydrous MGS04 and concentrated in vacuo to yield Intermediate 1 (1.84g, 96.8percent). The crude product was used on next step. NMR (400 MHz, CDC13) 8 3.52-3. 26 (m, 5H).Diisopropyl 3, 3-dimethoxycyclobutane-1, 1-dicarboxylate (31 g, 0.11 mol) was heated with 78 mL of 20percent HCl at reflux for 60 h. (2.5 g) of 3, 3-dimethoxycyclobutane-1, 1-dicarboxylic acid diisopropyl ester was added to a solution of 2.5 equivalents of KOH (3.0 g) in (15 mL) and stirred at room temperature for 4 hours Rear, 20 mL of concentrated hydrochloric acid was slowly added (the concentration of hydrochloric acid in the reaction solution was about 25percent), heated to reflux, reacted for 24 hours, and the reaction was completed.Cooled to room temperature and extracted with ethyl acetate three times. The organic phase was dried over anhydrous sodium sulfate and the organic solvent was distilled off under reduced pressure. The crude product was recrystallized to obtain 0.79 g of white crystals in 80percent yield.Compound 29.3 (150 g, 0.52 mol) was added to a solutionof 10 M HCI (400 ml), andthe reaction mixture was heated to reflux for 60 hr.The reactionmixture was cooledto rt, extracted with Et20 (10 x 1 L) and the combinedorganic layers were dried, filteredand concentrated under reduced pressureto give compound 29.4 (65 g) as a yellow oil, which was5 carriedthrough to the next step withoutfurther purification..3, 3-Dimethoxy-cyclobutane-1, 1-dicarboxylic acid diethyl ester (4.72 g, 18.15 mmol) was stirred with 20percent hydrochloric acid (50 ml) at reflux for 50 h. After cooling, the solution was continuously extracted with ether for 20 h. The ether was removed at reduced pressure and the residue was treated with hexanes and cooled. Filtration and wash with hexanes afforded 3-oxo-cyclobutanecarboxylic acid (1.4 g, 70percent) as a brown solid.

8.1 Usage: Useful intermediate for pharmaceutical, organic synthesis and organic light-emitting diode(OLED).

9. Computational chemical data

Molecular Weight: 114.1g/mol
Molecular Formula: C₅H₆O₃
Compound Is Canonicalized: True
XLogP3-AA: -0.8
Exact Mass: 114.031694049
Monoisotopic Mass: 114.031694049
Complexity: 131
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 54.4
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBgMAAAAAAAAAAAAAAAAABgAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAADQSAgAAACAAAAgAIAICQCAAAAAAAAAAAAAEAAAAAABIAAAAAQAAEAAAAAACLAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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3-oxocyclobutane-1-carboxylic acid Cas 23761-23-1 from China

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