Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 122665-97-8 | MDL No. : | MFCD03788493 |
Formula : | C7H10F2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HYIUDFLDFSIXTR-UHFFFAOYSA-N |
M.W : | 164.15 | Pubchem ID : | 2779136 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.56 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 1.29 |
Log Po/w (XLOGP3) : | 1.63 |
Log Po/w (WLOGP) : | 2.74 |
Log Po/w (MLOGP) : | 1.57 |
Log Po/w (SILICOS-IT) : | 1.73 |
Consensus Log Po/w : | 1.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.82 |
Solubility : | 2.49 mg/ml ; 0.0152 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.03 |
Solubility : | 1.55 mg/ml ; 0.00942 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.23 |
Solubility : | 9.71 mg/ml ; 0.0592 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With 4-(tert-butyl)-2,6-dimethylphenyl sulfur trifluoride; pyridine hydrogenfluoride In dichloromethane at 0 - 20℃; for 5 h; Inert atmosphere | Ethyl 4-oxycyclohexanecarboxylate (1.13g, 6.67mmol) was dissolved in anhydrous dichloromethane (10mL) in a high density polyethylene (HDPE) container. To it, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (2.5g, 9.99mol) was added and stirred under N2 at 0°C. HF-pyridine (0.64mL, 2.64mmol) was added to the vessel and the reaction was allowed to reach ambient temperature. After 5h, the reaction mixture was quenched with saturated aqueous NaHCO3. The organic layer was allowed to stir at ambient temperature in 2N NaOH for 1h. The aqueous layer was washed with dichloromethane and then acidified to pH 1 and extracted with dichloromethane. A total of 0.435g title compound was obtained at 27percent yield. 1H NMR (400MHz, CDCl3) δ 2.498–2.278 (m, 1H), 1.984–1.881 (m, 4H), 1.872–1.753 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With water; lithium hydroxide In tetrahydrofuran at 20℃; | A solution of ethyl 4,4-difluorocyclohexanecarboxylate (0.385 g, 2.003 mmol) in THF (12 mL) was treated with H2O (6 mL) followed by lithium hydroxide monohydrate (0.420 g, 10.02 mmol) and the mixture stirred vigorously at RT overnight. The mixture was treated with EtOAc, acidified with 1M HCl until pH 4, the layers separated and the aqueous layer extracted with additional EtOAc (1*). The combined organics were washed with brine, dried over MgSO4 and concentrated to dryness to afford 4,4-difluorocyclohexanecarboxylic acid (318 mg, 97percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.28 (s, 1H), 2.40 (m, 1H), 2.02-1.75 (m, 6H), 1.59 (m, 2H). |
94% | With sodium hydroxide In ethanol at 0 - 20℃; for 18 h; | To a solution of compound ethyl 4,4-difluorocyclohexanecarboxylate (4.2 g, 21.8 mmol) in 40 mL EtOH was treated with 2N NaOH (1.34 g, 32.8 mmol) at 0° C., and the mixture was allowed to warm to r.t. and stirred for 18 h. The mixture was diluted with water and the pH was adjusted to 3-4 with 6N HCl. The mixture was extracted with toluene, dried and concentrated to give the title compound 4,4-difluorocyclohexanecarboxylic acid (3.4 g, 94percent) as a white solid. (0474) 1H-NMR (CDCl3/400 MHz): δ 2.28-2.27 (m, 1H), 2.22-2.20 (m, 1H), 2.08-2.02 (m, 3H), 1.99-1.94 (m, 3H), 1.19 (s, 1H). |
92% | Stage #1: With sodium hydroxide In ethanol at 0 - 20℃; for 18 h; Stage #2: With hydrogenchloride In ethanol; water |
Step 5 4,4-Difluoro-cyclohexanecarboxylic acid: A solution of 4,4-difluoro-cyclohexanecarboxylic acid ethyl ester (970 mg, 5.0 mmol) in ethanol (5 mL) was treated with 2N sodium hydroxide (3.8 mL, 7.6 mmol) at 0° C., and the mixture was allowed to warm to ambient temperature and stirred for an additional 18 hours. The mixture was diluted with water (15 mL), and the pH was adjusted to 3-4 with 6 N hydrochloric acid. The mixture was extracted with toluene, dried and concentrated to give the title compound as a white solid. Yield: 758 mg (92percent). 1H-NMR (CDCl3.) δ: 1.60-2.23 (m, 8H), 2.45 (m, 1H). |
74.5% | Stage #1: at 25℃; for 2.5 h; Stage #2: With hydrogenchloride In water |
A suspension of 15.7 g ethyl 4,4-difluorocyclohexanoate (6.3 mmol), 2.1 g Candida antarctica lipase B from Novozyme (NOVO SP 435) and 375 g of buffer (Na2HPO4/NaH2PO4 pH=7.5, concentration: 50 mM) were placed in a flask. The mixture was stirred at 25°C for 2:30 h. The lipase was filtered off and the solution was acidified until pH=2 by addition of 35g of HCl 6M. A solid was formed and directly filterted. The aqueous phase was 3 times extracted with CH2Cl2. The solvent was removed using a rotavapor and 3.5 g of additional solid were obtained. The combined solids were dried. Yield: 74.5percent. The purity determined by NMR was 100percent. |
55% | at 40℃; for 6 h; | A suspension of ethyl 4,4-difluorocyclohexanoate (41.7 g; 0.22mol) and concentrated aqueous HCl solution (107.5 g; 1.9 mol; 8.8 eq.) was placed into a round bottom flask equipped with a cooler (2°C). The mixture was heated under stirring to 40 °C for 6 h. Afterwards the solution was extracted 5 times with ethyl ether and the combined fractions were washed once with saturated aqueous NaCl solution. The solvent was removed and a solid was obtained which was recrystallised two times from hot chloroform. 19.2 g were isolated with a purity determined by NMR of 99.5percent and no olefinic compound was detectable via NMR. The yield was 55percent. |
[ 107496-54-8 ]
3,3-Difluorocyclobutanecarboxylic acid
Similarity: 0.94
[ 915030-40-9 ]
2-(4,4-Difluorocyclohexyl)acetic acid
Similarity: 0.94
[ 133261-33-3 ]
trans-4-(Trifluoromethyl)cyclohexane-carboxylicacid
Similarity: 0.85
[ 214557-89-8 ]
3,5,7-Trifluoroadamantane-1-carboxylic acid
Similarity: 0.82
[ 178312-47-5 ]
Ethyl 4,4-difluorocyclohexanecarboxylate
Similarity: 0.82
[ 107496-54-8 ]
3,3-Difluorocyclobutanecarboxylic acid
Similarity: 0.94
[ 915030-40-9 ]
2-(4,4-Difluorocyclohexyl)acetic acid
Similarity: 0.94
[ 133261-33-3 ]
trans-4-(Trifluoromethyl)cyclohexane-carboxylicacid
Similarity: 0.85
[ 214557-89-8 ]
3,5,7-Trifluoroadamantane-1-carboxylic acid
Similarity: 0.82
[ 178312-47-5 ]
Ethyl 4,4-difluorocyclohexanecarboxylate
Similarity: 0.82
[ 107496-54-8 ]
3,3-Difluorocyclobutanecarboxylic acid
Similarity: 0.94
[ 915030-40-9 ]
2-(4,4-Difluorocyclohexyl)acetic acid
Similarity: 0.94
[ 133261-33-3 ]
trans-4-(Trifluoromethyl)cyclohexane-carboxylicacid
Similarity: 0.85
[ 214557-89-8 ]
3,5,7-Trifluoroadamantane-1-carboxylic acid
Similarity: 0.82
[ 107873-03-0 ]
2,2-Difluorocyclopropanecarboxylic acid
Similarity: 0.80