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| | 4,4-DIFLUOROCYCLOHEXANONE Basic information |
| Product Name: | 4,4-DIFLUOROCYCLOHEXANONE | | Synonyms: | 4,4-DIFLUOROCYCLOHEXANONE;1,1,-Difluoro-4-oxocyclohexane;4,4-difluro-cyclohexanone;4,4-Difluorocyclohexanone;Cyclohexanone, 4,4-difluoro-;4,4-Difluorocyclohexanone(WX900093);uorocycL;TIANFU CHEM --4,4-DIFLUOROCYCLOHEXANONE | | CAS: | 22515-18-0 | | MF: | C6H8F2O | | MW: | 134.12 | | EINECS: | | | Product Categories: | Alkyl Fluorinated Building Blocks;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Fluorinated Building Blocks;Ketones;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks | | Mol File: | 22515-18-0.mol |  |
| | 4,4-DIFLUOROCYCLOHEXANONE Chemical Properties |
| Melting point | 35-36°C | | Boiling point | 157.4±40.0 °C(Predicted) | | density | 1.14g/ml | | Fp | 65°C | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | form | low melting solid | | Appearance | white solid | | Water Solubility | Insoluble in water. | | InChI | InChI=1S/C6H8F2O/c7-6(8)3-1-5(9)2-4-6/h1-4H2 | | InChIKey | NYYSPVRERVXMLJ-UHFFFAOYSA-N | | SMILES | C1(=O)CCC(F)(F)CC1 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29147000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4,4-DIFLUOROCYCLOHEXANONE Usage And Synthesis |
| Chemical Properties | White to brown solid | | Uses | 4,4-Difluorocyclohexanone is used as a pharmaceutical intermediate. | | Synthesis | 4.3. Synthesis of 4,4-difluorocyclohexanone (8): the acetonide 7 (20.0 g, 112.2 mmol) was suspended in 20% HCl aqueous solution (16 mL) and stirred vigorously for 3 hours at 100 °C. After the reaction was completed, it was cooled to room temperature and NaCl (~3 g) was added to the aqueous phase to dissolve it. Subsequently, the aqueous phase was extracted with CH2Cl2 (3 x 50 mL). The organic phases were combined, washed with 50 mL of water, dried over Na2SO4, and the solvent was slowly evaporated under reduced pressure at 20 °C. Due to the extreme instability of the product, the material initially obtained was a 1:1 mixture of product 8 and raw material 5. After repeating the above operation, the ratio of 8 to 5 in the mixture was increased to 7:3. After a number of repetitions, the final product 8 was obtained with 95% purity as white crystals (11.0 g, 71% yield) with a melting point of 31-32°C. The product was then dried over 50 mL of water and evaporated slowly at 20°C under reduced pressure. | | References | [1] Organic Letters, 2013, vol. 15, # 5, p. 1088 - 1091
[2] Tetrahedron, 2013, vol. 69, # 20, p. 4066 - 4075
[3] Patent: US2006/293392, 2006, A1. Location in patent: Page/Page column 51
[4] Patent: WO2008/7930, 2008, A1. Location in patent: Page/Page column 28
[5] Patent: WO2009/48547, 2009, A1. Location in patent: Page/Page column 40 |
| | 4,4-DIFLUOROCYCLOHEXANONE Preparation Products And Raw materials |
| Raw materials | 8,8-difluoro-1,4-dioxaspiro[4.5]decane-->4,4-difluoroheptanedioic acid diethyl ester-->DIETHYL 4-OXOPIMELATE-->Hydrochloric acid-->3-(2-Furyl)acrylic acid-->1,4-Dioxaspiro[4.5]decan-8-one | | Preparation Products | (4,4-difluorocyclohexyl)methanamine-->2-(4,4-Difluorocyclohex-1-en-1-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane-->AC 186-->Acetic acid, 2-(4,4-difluorocyclohexylidene)-, ethyl ester-->Ethyl 5,5-difluoro-2-oxo-cyclohexanecarboxylate |
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