3-Oxocyclobutanecarboxylic acid CAS 23761-23-1
Introduction：Basic information about 3-Oxocyclobutanecarboxylic acid CAS 23761-23-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
3-Oxocyclobutanecarboxylic acid Basic information
| Product Name: | 3-Oxocyclobutanecarboxylic acid |
| Synonyms: | 3-OXO-CYCLOBUTANECARBOXYLIC ACID;(3-oxocyclobutyl)carboxylic acid;3-Oxycyclobutanecarboxylic acid;3-Oxo-cyclobutanecarboxylic acid ,95%;3-Oxocyclobutanecarboxyli...;3-oxocyclobutanecarboxylic acid(SALTDATA: FREE);3-Oxocyclobutane-1-carboxylic acid 98%;IFLAB-BB F2124-0041 |
| CAS: | 23761-23-1 |
| MF: | C5H6O3 |
| MW: | 114.1 |
| EINECS: | 639-432-5 |
| Product Categories: | Building Blocks/Intermediates;API intermediates;Pharmaceutical intermediate;Miscellaneous Reagents |
| Mol File: | 23761-23-1.mol |
3-Oxocyclobutanecarboxylic acid Chemical Properties
| Melting point | 69-70℃ |
| Boiling point | 296°C |
| density | 1.431 |
| Fp | 147°C |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| pka | 4.35±0.20(Predicted) |
| form | Solid |
| color | Off-white |
| Water Solubility | Slightly soluble in water. |
| InChI | InChI=1S/C5H6O3/c6-4-1-3(2-4)5(7)8/h3H,1-2H2,(H,7,8) |
| InChIKey | IENOFRJPUPTEMI-UHFFFAOYSA-N |
| SMILES | C1(C(O)=O)CC(=O)C1 |
| CAS DataBase Reference | 23761-23-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22 |
| Safety Statements | 26-37-60 |
| WGK Germany | WGK 3 |
| TSCA | No |
| HS Code | 29189900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Description | 3-Oxocyclobutanecarboxylic acid is an organic common intermediate compound used in pharmaceuticals, organic synthesis and organic light-emitting diode (OLED) intermediates. Abrocitinib, prepared from 3-Oxocyclobutanecarboxylic acid, is approved for the treatment of adult patients with atopic dermatitis (AD), as well as patients with refractory moderate to severe AD who have had limited or minimal response to other systemic medications. |
| Chemical Properties | White solid |
| Uses | 3-Oxocyclobutanecarboxylic Acid (cas# 23761-23-1) is a compound useful in organic synthesis. |
| Application | 3-Oxocyclobutanecarboxylic acid is a very important medicine intermediate, it is widely applied in the synthetic of tens kinds of bulk drugs, such as ACK1 antibody, the MDM2 antagonist, the JAK inhibitor, CETP inhibitor, kinase inhibitor, the PDE10 inhibitor, thrombin inhibitors and in autoimmunization chronic inflammatory diseases and antitumor drug, all being used to. |
| Preparation | The target product 3-oxocyclobutanecarboxylic acid is obtained by adopting acetone, bromine, and malononitrile as raw materials, adopting ethanol, DMF (dimethyl formamide), and water as solvents, adopting sodium iodide as an activating agent and tetrabutylammonium bromide (TBAB) as a phase transfer catalyst through three-step reaction. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 53, p. 3841, 1988 DOI: 10.1021/jo00251a033 |
| Synthesis | 115118-68-8 23761-23-1 General procedure for the synthesis of 3-oxocyclobutanecarboxylic acid from 3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester: the product of step A (4.8 g, 17 mmol) was mixed with 20% HCl (20 mL) and the reaction was stirred under refluxing conditions for 60 hours. After completion of the reaction, the mixture was cooled to room temperature. Ether was added to the reaction mixture and stirred vigorously for 24 hours. The ether layer was separated and the aqueous layer was extracted with ether three times (3×). All organic layers were combined and dried with anhydrous MgSO4 and subsequently concentrated under vacuum to give Intermediate 1 (1.84 g, 96.8% yield). This crude product was used directly in the next step of the reaction. The NMR hydrogen spectrum (400 MHz, CDCl3) data of intermediate 1 were as follows: δ 3.52-3.26 (m, 5H). |
| References | [1] Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3841 - 3843 [2] Patent: WO2004/82682, 2004, A1. Location in patent: Page 35-36 [3] Synlett, 2009, # 11, p. 1827 - 1829 [4] Chemistry - A European Journal, 2011, vol. 17, # 2, p. 468 - 480 [5] Patent: US2009/233903, 2009, A1. Location in patent: Page/Page column 46 |
3-Oxocyclobutanecarboxylic acid Preparation Products And Raw materials
| Raw materials | Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate-->1,1-diethyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate |
| Preparation Products | 3,3-Difluorocyclobutanecarboxylic acid-->5,8-Dioxaspiro[3.4]octane-2-Methanol-->Methyl 3-broMocyclobutane-1-carboxylate-->3-BroMocyclobutanone-->3-Hydroxy-cyclobutanecarboxylic acid ethyl ester-->Methyl cis-3-hydroxycyclobutanecarboxylate-->Carbamic acid, (3-hydroxycyclobutyl)-, 1,1-dimethylethyl ester (9CI)-->3-METHYLENECYCLOBUTANECARBOXYLIC ACID-->3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester-->isopropyl3-oxocyclobutane-1-carboxylate-->Cyclobutanecarboxamide, N,N-dimethyl-3-oxo-, diethyl acetal (6CI)-->3,3-difluorocyclobutane-1-carbonyl chloride-->N-((3-chloropyrazin-2-yl)Methyl)-3-oxocyclobutanecarboxaMide |
