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[ CAS No. 122-99-6 ] {[proInfo.proName]}

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Chemical Structure| 122-99-6
Chemical Structure| 122-99-6
Structure of 122-99-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 122-99-6 ]

CAS No. :122-99-6 MDL No. :MFCD00002857
Formula : C8H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCDWFXQBSFUVSP-UHFFFAOYSA-N
M.W : 138.16 Pubchem ID :31236
Synonyms :

Calculated chemistry of [ 122-99-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.9
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.16
Log Po/w (WLOGP) : 1.06
Log Po/w (MLOGP) : 1.21
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.67
Solubility : 2.93 mg/ml ; 0.0212 mol/l
Class : Very soluble
Log S (Ali) : -1.37
Solubility : 5.85 mg/ml ; 0.0423 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.627 mg/ml ; 0.00454 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 122-99-6 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P501-P261-P270-P271-P264-P280-P301+P312+P330-P304+P340+P312-P305+P351+P338+P310-P403+P233-P405 UN#:N/A
Hazard Statements:H302-H318-H335-H336 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 122-99-6 ]

* 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.

  • Upstream synthesis route of [ 122-99-6 ]
  • Downstream synthetic route of [ 122-99-6 ]

[ 122-99-6 ] Synthesis Path-Upstream   1~10

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  • [ 253-82-7 ]
Reference: [1] Patent: US4766211, 1988, A,
  • 2
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  • [ 589-10-6 ]
Reference: [1] Letters in Organic Chemistry, 2012, vol. 9, # 8, p. 598 - 603,6
[2] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 9, p. 1471 - 1480
[3] Journal of Organic Chemistry, 1968, vol. 33, # 6, p. 2271 - 2284
[4] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698,7
[5] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698
[6] Polyhedron, 2014, vol. 67, p. 205 - 212
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  • [ 622-86-6 ]
YieldReaction ConditionsOperation in experiment
96.8% With benzenesulfonyl chloride In 1-methyl-pyrrolidin-2-one at 20 - 100℃; for 0.5 h; At room temperature, 2.5 mL of N-methylpyrrolidone (NMP), 1.38 g (10 mmol) of 2-benzeneOxyethanol and 1.5 mL (11 mmol) of benzenesulfonyl chloride. Mixed uniformly, and reacted at 100 ° C for 30 min under stirring. stopAfter the reaction mixture was cooled to room temperature, 30 mL of dichloromethane and 30 mL of water were added, and the mixture was thoroughly mixed,The organic layer was washed with saturated brine, driedThe crude product was obtained by evaporation of methylene chloride. Further chromatography afforded 1.52 g of colorless liquid, and the yield was 96.8percent.
94% With pyridine; thionyl chloride In toluene at 10 - 80℃; Large scale 10233] In to clean, dry, nitrogen flushed 750 1 GER, charged toluene (150 E), 2-phenoxyethanol (15 kg, 0.108 mol) and pyridine (1.2 kg, 0.162 mol, 0.15 equiv). reaction mass was cooled to 10-15° C., added thionyl chloride (19.3 kg, 0.162 mol, 1.5 equiv) over 90 mm. The reaction mixture was then heated to reflux and maintained for 10-12 h. After the reaction completion, it was cooled to 10-15° C. andquenched with water (500 L). The aqueous phase was separated and discarded. The washing procedure was repeated one more time before the vessel was set for vacuum distillation and heated at less than 60° C. until toluene (500L) had been removed. The residue was then cooled to 30-35° C. before being transferred to a smaller vessel (16 kg, 94percent, 95.89percent HPLC purity).10234] ‘H NMR (400 MHz, DMSO-d6): ö 7.27-7.31 (t, 2H), 6.94-6.96 (t, 3H), 4.22-4.25 (t, 2H), 3.95-4.0 (t, 2H); HPLC: 95.89percent at 210 nm.
83% With pyridine; thionyl chloride; sodium sulfate In toluene a.
Preparation of 1-Chloro-2-phenoxyethane
To a flask was added 41.5 grams (g.) (0.3 mole) of 2-phenoxyethanol, 50 ml of toluene and 3.93 g. of pyridine, then 39.3 g. (0.33 mole) of thionyl chloride dropwise while stirring at room temperature.
The exothermic reaction was heated at 50°-60° C. for two hours.
After cooling to room temperature, the resulting salt was filtered and washed with methylene chloride.
The filtrate was washed several times with aqueous sodium bicarbonate, dried using sodium sulfate, and then concentrated to obtain 39 g. of the 1-chloro-2-phenoxyethane as a yellow oil (83percent yield).
66.8% With thionyl chloride In N,N-dimethyl-formamide at 50℃; for 5 h; Plus phenoxyethanol(7a, 4.5 mmol), THF (5 mL), SOCl2 (1 mL), DMF (2 drops), and the reaction was carried out at 50C for 5 h. reaction The reaction solution was concentrated under reduced pressure to dryness to give crude product. Column chromatography (petroleum ether / ethyl acetate 20/1, V / V) gave a colorless liquid, yield 66.8percent

Reference: [1] Patent: CN106187674, 2016, A, . Location in patent: Paragraph 0017; 0018
[2] Patent: US2016/347717, 2016, A1, . Location in patent: Paragraph 0232; 0233
[3] Patent: US5527816, 1996, A,
[4] Chemical Research in Toxicology, 2000, vol. 13, # 1, p. 53 - 62
[5] Patent: CN106146450, 2016, A, . Location in patent: Paragraph 0132; 0133; 0134
[6] Journal of the American Chemical Society, 1933, vol. 55, p. 1572,1573
[7] Journal of the American Chemical Society, 1926, vol. 48, p. 2748
[8] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 3, p. 774 - 777
[9] Organic Preparations and Procedures International, 1994, vol. 26, # 3, p. 343 - 346
[10] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698,7
[11] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698
[12] Organic Process Research and Development, 2001, vol. 5, # 5, p. 479 - 490
[13] Russian Journal of General Chemistry, 2016, vol. 86, # 6, p. 1274 - 1281[14] Zh. Obshch. Khim., 2016, vol. 86, # 6, p. 944 - 951,8
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  • [ 56-93-9 ]
  • [ 622-86-6 ]
Reference: [1] Patent: US5091577, 1992, A,
[2] Patent: US5093526, 1992, A,
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  • [ 122-99-6 ]
  • [ 67-68-5 ]
  • [ 13879-32-8 ]
  • [ 622-86-6 ]
Reference: [1] Synthesis, 2009, # 22, p. 3828 - 3832
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  • [ 6161-87-1 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide; chlorine; sodium hydrogensulfite In hydrogenchloride; methanol; water EXAMPLE 1
Preparation of 2-(2,4,6-trichlorophenoxy)-ethanol:
in the presence of hydrogen chloride (Stage I (a)
Into a three-necked, round-bottomed 1-liter flask fitted with a stirrer, thermometer, reflux condenser, and a gas sparger are added 70 g of 2-phenoxyethanol dissolved in 125 ml of HCl (32percent).
The reaction mixture is cooled with stirring to 0°-25° C. and chlorine gas is added at a rate sufficient to keep the temperature at 0° C. 5° C. cooling when necessary.
During the reaction a second liquid phase appears.
After adding two thirds of the chlorine (about 7 hours) the temperature is raised to 25° C. and the remaining chlorine is added at a slower rate (additional 8 hours) where a total of 125 g of chlorine are added.
The stirring is stopped and the lower organic layer is poured into 100 ml of 20percent stirred solution of sodium bisulfite kept at a temperature of 70° C.
A 10percent sodium hydroxide solution is added until a pH of 7.5 is reached, the stirring is stopped, the lower organic layer is separated, dissolved in 150 ml methanol and 50 ml water kept at 45° C.
The resulting solution is cooled to 0°-5° C. to precipitate the crystalline product.
The crystals are filtered, washed with water, and dried to yield 2-(2,4,6-trichlorophenoxy)-ethanol in a yield of 88percent having a purity of 98-99percent.
Reference: [1] Patent: US5091578, 1992, A,
[2] Patent: US5091578, 1992, A,
  • 7
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  • [ 3598-16-1 ]
Reference: [1] Angewandte Chemie, 1981, vol. 93, # 9, p. 812 - 813
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  • [ 139-02-6 ]
  • [ 3598-16-1 ]
Reference: [1] Angewandte Chemie, 1981, vol. 93, # 9, p. 812 - 813
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  • [ 486-25-9 ]
  • [ 117344-32-8 ]
YieldReaction ConditionsOperation in experiment
90.2% at 130℃; for 4 h; Inert atmosphere Example 12 A reaction was carried out by (a) adding 80.0 g (0.444 mol) of fluorenone, 613.5 g (4.44 mol) of 2-phenoxyethanol, and 2.0 g of tungstophosphoric acid [(H3PW12O40).nH2O] serving as a catalyst to a glass reactor vessel equipped with a stirrer, a nitrogen-blowing tube, a thermometer and a T-tube and (b) allowing a mixture to react for 4 hours under a reduced pressure of 2.0.x.103 Pa at 130° C. The content of multimers in a reaction mixture obtained after completion of the reaction was 3.9percent. To the reaction mixture thus obtained, 800.0 g of toluene was added. The reaction mixture was neutralized with a sodium hydroxide aqueous solution and washed with water. Thereafter an organic phase was separated. Toluene and excess 2-phenoxyethanol were removed from an obtained organic phase by concentration under reduced pressure. To an obtained concentrate, 560.0 g of toluene was added, and the mixture was heated and stirred at 80° C. for 1 hour and thereafter directly cooled to 70° C. Thereafter, 0.4 g of crystals of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene serving as seed crystals were added, and a mixture was incubated at 70° C. for 2 hours and thereafter directly cooled to 20° C. Then, precipitated crystals were subjected to filtration and drying to obtain 78.0 g of white crystals of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (yield: 90.2percent, purity: 99.2percent). The 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene thus obtained had a melting point of 163° C.
85.4% at 50℃; for 18 h; Inert atmosphere A thermometer, a stirrer, 2 - neck flask equipped with condenser 4 544.7 g phenoxyethanol (3.94mol) as raw materials, the reaction vessel was replaced with nitrogen after, at 40 °C 840.7 g was added methanesulfonic acid (8.75mol). Then, 3.8 g of β - mercaptopropionic acid were added at 50 °C, 2 - phenoxyethanol is 9 - fluorenone (1.93mol) dissolved therein (3.78mol) 521.9 g 347.9 g was added dropwise over 1 hour at 50 °C solution after the reaction. After the completion of the dropping, stirring was carried out at 50 °C 17 hours. By using high-performance liquid chromatography analysis of the reaction solution as a result of calibration curve, 9, 9 - bis (4 - (2 - hydroxyethoxy) phenyl) fluorene in the reaction liquid is present in the yield of 85.4percent. After completion of the reaction, stirring 1287.2 g toluene, 50 °C 890.9 g water was added followed by order, standing water layer 1664 g being pulled. In 48percent aqueous methanesulfonic acid concentrations, the recovery rate was 95percent. Thereafter heated to 80 °C, 16percent sodium hydroxide aqueous solution was added 3 hours 1042.4 g. After stirring, the aqueous layer was extracted after standing, 75percent phosphoric acid aqueous solution was added to the neutralizing aqueous 347.9 g and 14.3 g. After that, the water layer to settle out, water is added after stirring at 80 °C 347.9 g oil, water washing operation was performed twice to remove isolation layer 2. Oil obtained from toluene, 2 - phenoxyethanol was removed by vacuum distillation of the excess. After distillation of the residual liquid is added to the homogeneous solution after toluene 2435.3 g, 2 hours to precipitate out at 65 °C, 25 °C gradually cooled filtrate the deposited crystal, drying the crude crystal 630.4 g was obtained. The 97.6percent purity by analytical high-performance liquid chromatography was. 60.0 g of crude crystals were obtained with a thermometer, a stirrer, a cooling pipe 4 neck flask equipped with a charge and, after nitrogen substitution, addition of 1 - butanol 120.0 g, 78 °C temperature raised to dissolve. Thereafter, 9, 9 - bis [4 - (2 - hydroxyethoxy) phenyl] fluorene is 75 °C at high melting point crystalline seed crystal was added, 1 hour at 55 °C crystalline precipitate. After heated up to 65 °C, gradually cooling the precipitated crystal was filtered off 25 °C. The resulting crystals under vacuum, dried and heated to 80 °C, 9, 9 - bis [4 - (2 - hydroxyethoxy) phenyl] fluorene 52.8 g was obtained. 88percent yield for crude crystals which, 98.7percent purity by analytical high-performance liquid chromatography was. Fig. 1 shows the data obtained from DSC crystal. An endothermic maximum temperature: (differential scanning calorimetry) 121.1 °C
75.1% for 12 h; Inert atmosphere; Reflux Example 3: Production of crude product Into a glass reactor equipped with a stirrer, a nitrogen blowing tube, a thermometer and a water separator with cooling tube was added 86.4 g (0.48 mol) of fluorenone, 397.9 g (2.88 mol) of phenoxyethanol, 350 g of toluene and 4.3 g of phosphotungstic acid [(H3PW12O40)] which had been dried under reduced pressure at 100°C to remove crystal water, and the mixture was stirred for 12 hours while removing generated water out of the system, under toluene reflux. The resultant reaction liquid was analyzed by high performance liquid chromatography to find generation of 197.3 g (0.45 mol) of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene. To this reaction liquid was added 300 g of toluene, and water-washed at 80°C using 100 g of water. The resultant organic layer was cooled gradually, to find initiation of deposition of a crystal at 12°C, and the organic layer was cooled down to 10°C without any other procedure, and stirred for 12 hours. The deposited crystal was taken out by filtration, and the crystal was dried to obtain 158.0 g (yield: 75.1percent, LC purity: 99.9percent) of a white crystal of a crude product of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene. The resultant crystal had a melting point (melt endotherm maximum by differential scanning calorimetry) of 109°C, and a bulk density of 0.24 g/cm3.
104.5 g at -40 - 80℃; for 17 h; Autoclave; Inert atmosphere 500 ml stainless steel reactor was added fluorenone 50 g (0.277), ethylene glycol monophenyl ether, 172.5 g, 0.6 g 3-mercaptopropionic acid, sealed reactor, pressure tested with nitrogen, the reactor sealed after confirmation, system was purged twice with nitrogen, the autoclave was cooled to -40 ~ -50 ° C , slow flow of anhydrous hydrogen fluoride gas is condensed to a liquid hydrogen fluoride in a reactor, to the reactor 150 g weight gain, hydrogen fluoride was stopped.The reaction vessel was heated to 70 ~ 80 ° Creaction for 17 hours.The reaction system was cooled to 40 ~ 50 ° C, slowly open the exhaust valve, exhaust gas is hydrogen fluoride, hydrogen fluoride gas recovery after a condenser to condense the hydrogen fluoride until the basic system is discharged to the reaction vessel purged with nitrogen, the remaining hydrogen fluoride rush out, stop nitrogen.Was slowly added to the kettle 6percent potassium bicarbonate 150 g, was heated to 70 ~ 80 ° C, stirred for 15 minutes, 150 g of toluene was added, stirred for 20 minutes, allowed to stand, the organic phase was separated, the aqueous phase with 60 g of toluene extracted once, and the combined organic phase was washed with pure water twice the amount of 60 grams.The organic phase cooling crystallization, filtration, washing, drying dryness to give 9,9-bis [(4-hydroxy) phenyl]fluorene 104.5 g, 99.2percent purity.

Reference: [1] Patent: US2012/29244, 2012, A1, . Location in patent: Page/Page column 15
[2] Patent: JP6139508, 2017, B2, . Location in patent: Paragraph 0024
[3] Patent: EP2123625, 2009, A1, . Location in patent: Page/Page column 6
[4] Chemistry Letters, 1998, # 10, p. 1055 - 1056
[5] Chemistry Letters, 1998, # 10, p. 1055 - 1056
[6] Synthetic Communications, 2007, vol. 37, # 24, p. 4407 - 4413
[7] Patent: CN104030899, 2016, B, . Location in patent: Paragraph 0035; 0036
[8] Patent: JP6156858, 2017, B1, . Location in patent: Paragraph 0056
[9] Patent: JP2018/24630, 2018, A, . Location in patent: Paragraph 0056; 0077; 0084
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  • [ 25023-01-2 ]
  • [ 117344-32-8 ]
YieldReaction ConditionsOperation in experiment
13.5 g
Stage #1: at 70℃; for 3 h; Inert atmosphere
Stage #2: at 110℃; for 9 h; Inert atmosphere
mixer,Nitrogen blowing tube,23.5 g (0.17 mol) of 2-phenoxyethanol was charged in a glass reactor equipped with a thermometer and a cooling tube,After replacing the reaction vessel with nitrogen,A mixed solution of 10.0 g (0.0425 mol) of 9,9-dichloro-9H-fluorene and 11.7 g (0.08 mol) of 2-phenoxyethanol was added dropwise at 70 ° C. over 1 hour with stirring.After completion of the dropwise addition,After stirring at 70 ° C. for 2 hours,4.1 g (0.04 mol) of methanesulfonic acid was added and stirred at 110 ° C. for 9 hours. As a result of analyzing the obtained reaction solution by high performance liquid chromatography,The composition value of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene was 72.5percent (area percentage / 2-phenoxyethanol excluded). From the composition value, formation of 13.5 g of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene was confirmed.
Reference: [1] Patent: JP6234367, 2017, B2, . Location in patent: Paragraph 0029
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