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[ CAS No. 711-33-1 ] {[proInfo.proName]}

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Chemical Structure| 711-33-1
Chemical Structure| 711-33-1
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Product Details of [ 711-33-1 ]

CAS No. :711-33-1 MDL No. :MFCD00039231
Formula : C10H9F3O Boiling Point : -
Linear Structure Formula :- InChI Key :QFKOWENRSZZLPK-UHFFFAOYSA-N
M.W : 202.17 Pubchem ID :136554
Synonyms :

Calculated chemistry of [ 711-33-1 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.45
TPSA : 17.07 Ų

Pharmacokinetics

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) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 3.07
Log Po/w (WLOGP) : 4.45
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 3.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.15
Solubility : 0.144 mg/ml ; 0.000713 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.162 mg/ml ; 0.000803 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.03
Solubility : 0.0189 mg/ml ; 0.0000933 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 711-33-1 ]

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:

Application In Synthesis of [ 711-33-1 ]

* 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 [ 711-33-1 ]
  • Downstream synthetic route of [ 711-33-1 ]

[ 711-33-1 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 67081-98-5 ]
  • [ 711-33-1 ]
YieldReaction ConditionsOperation in experiment
97.2%
Stage #1: With sodium dihydrogenphosphate; tetra(n-butyl)ammonium hydrogensulfate In water
Stage #2: With sodium hypochlorite In water for 0.5 h;
The 1- (p-trifluoromethylphenyl) -1-propanol solution prepared in step 1 was mixed with 3.9 kg of tetrabutylammonium hydrogen sulfate and 12.3 kg of sodium phosphate dihydrate monobasic, which were dissolved in 32 liters of purified water. After the mixture was washed by the addition of 10 liters of purified water, 318 kg of 12percent sodium hyperchlorite was added to the mixture, followed by EPO <DP n="19"/>washing by adding 35 liters of purified water. After the resulting solution was allowed to stand for 30 min, the formed organic layer was mixed with 358 liters of purified water and 18 kg of 38percent hydrochloric acid, and stirred for 5 min. The separated organic layer was washed with purified water, and 378 kg of p-trifluoromethyl propiophenone was obtained from the organic layer (yield: 97.2percent).
Reference: [1] Synthetic Communications, 1989, vol. 19, # 9-10, p. 1735 - 1744
[2] Patent: WO2006/112565, 2006, A1, . Location in patent: Page/Page column 16-17
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3918 - 3932
[4] European Journal of Medicinal Chemistry, 1995, vol. 30, # 1, p. 85 - 94
[5] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1594 - 1596
[6] Patent: US5478826, 1995, A,
[7] Catalysis Science and Technology, 2016, vol. 6, # 9, p. 3208 - 3213
[8] Helvetica Chimica Acta, 2017, vol. 100, # 3,
[9] Green Chemistry, 2017, vol. 19, # 2, p. 474 - 480
  • 2
  • [ 149946-79-2 ]
  • [ 711-33-1 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 24, p. 6102 - 6105
[2] Green Chemistry, 2010, vol. 12, # 9, p. 1628 - 1633
  • 3
  • [ 402-43-7 ]
  • [ 104863-65-2 ]
  • [ 711-33-1 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 4543 - 4545[2] Angewandte Chemie, 2009, vol. 121, p. 4613 - 4615
  • 4
  • [ 392-83-6 ]
  • [ 123-62-6 ]
  • [ 711-33-1 ]
YieldReaction ConditionsOperation in experiment
34.5 %Chromat.
Stage #1: With ethylmagnesium bromide; magnesium; lithium chloride In tetrahydrofuran; ethyl bromide at 45 - 50℃; for 5 h; Inert atmosphere
Stage #2: at 20 - 30℃; for 2 h; Inert atmosphere
General procedure: To a 200 ml-four-necked flask with a thermometer,75.0 g of tetrahydroffiran (1.04 mol; manufactured by Nacalai Tesque, Inc.), 5.1 g of magnesium powder (0.208 mol; manufactured by Chuo-kosan), 1.7 g of LiC1 (0.04 mol; manufactured by Nacalai Tesque, Inc.) were placed and the mixture was stirred while the inside of the system was substituted with a nitrogen gas. To this, 0.5 g of 1 mol/L ethylmagnesium bromide THF solution (manufactured by Tokyo Chemical Industry Co., Ltd.) was added and water in the system was removed. Subsequently, 0.44 g of ethyl bromide (0.004 mol; manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto. The mixture was stirred for a while; and the generation of heat was confirmed. Subsequently, 36.1 g of o-chlorobenzotrifluoride (0.2 mol; manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added dropwise, while the temperature of the reaction solution was kept at 45 to 50° C. After the completion of the dropwise addition, the mixture was allowed to mature while stirred at 45° C. for five hours, thereby obtaining a Grignard reagent solution.10043] Next, to a 200 ml-four-necked flask with a thermometer, 30.6 g of acetic anhydride (0.3 mol; manufactured by Wako Pure Chemical Industries, Ltd.), 10.8 g of toluene (0.3 fold by weight/o-chlorobenzotrifluoride: manufactured by Wako Pure Chemical Industries, Ltd.) were placed and the mixture was stirred in a water bath while the inside of the system was substituted with a nitrogen gas. To this, the above Grignard reagent solution was added dropwise while the temperature of the reaction solution was controlled so as to be 20 to 30° C. The entire volume of the Grignard reagent solution was added dropwise and then the mixture was stirred at 25° C. for two hours. After the completion of the stirring, the temperature of the reaction solution was decreased to room temperature; and 39.2 g of 3percent hydrogen chloride aqueous solution was gradually added dropwise thereto in a water bath. Afier the dropwise addition, the hydrolysis was completed by stirring for one hour. After the hydrolysis, the stirring was stopped; and the resultant was lefi to stand for separation, thereby obtaining an oil phase containing o-trifluoromethyl acetophenone. The obtained oil phase was analyzed by a gas chromatography method (GC) and as a result, the yield of 2’-trifluoromethyl acetophenone reaction was 82.7percent (based on the raw material, o-chlorobenzotrifluoride). A reaction was carried out in the same manner as described in Example 1 except that 36.1 g (0.2 mol) of o-chlorobenzotrifluoride was altered to 45.0 g (0.2 mol) of o-bromobenzotrifluoride in Example 1. The obtained oil phase was analyzed by a gas chromatography method; and as a result, the yield of 2’-tri- fluoromethyl acetophenone reaction was 85.5percent (based on the raw material, o-bromobenzotrifluoride). [0054] A reaction was carried out in the same manner as described in Comparative Example 1 except that 45.0 g (0.2 mol) of m-bromobenzotrifluoride was altered to 45.0 g (0.2 mol) of p-bromobenzotrifluoride in Comparative Example 1. The obtained oil phase was analyzed by a gas chromatography method; and as a result, the yield of 4’-trifluoromethyl acetophenone reaction was 40.0percent (based on the raw material, p-bromobenzotrifluoride). [0055] A reaction was carried out in the same manner as described in Comparative Example 2 except that 30.6 g (0.3 mol) of acetic anhydride was altered to 39.0 g (0.3 mol) of propionic anhydride in Comparative Example 2. The obtained oil phase was analyzed by a gas chromatography method; and as a result, the yield of 4’-trifluoromethyl propiophenone was 34.5percent (based on the raw material,p-bromobenzotrifluoride).
Reference: [1] Patent: US2017/88499, 2017, A1, . Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047; 0055
  • 5
  • [ 709-63-7 ]
  • [ 68-12-2 ]
  • [ 711-33-1 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 1, p. 66 - 69
  • 6
  • [ 42006-43-9 ]
  • [ 711-33-1 ]
  • [ 713-45-1 ]
Reference: [1] Chemical Communications, 2001, # 18, p. 1844 - 1845
  • 7
  • [ 79756-87-9 ]
  • [ 711-33-1 ]
  • [ 713-45-1 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 16, p. 5766 - 5767
  • 8
  • [ 455-19-6 ]
  • [ 711-33-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1594 - 1596
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3918 - 3932
[3] Synthetic Communications, 1989, vol. 19, # 9-10, p. 1735 - 1744
[4] Organic Letters, 2015, vol. 17, # 24, p. 6102 - 6105
[5] Patent: WO2006/112565, 2006, A1,
  • 9
  • [ 74-96-4 ]
  • [ 455-24-3 ]
  • [ 329-15-7 ]
  • [ 711-33-1 ]
Reference: [1] Patent: US4690931, 1987, A,
  • 10
  • [ 97-94-9 ]
  • [ 106376-16-3 ]
  • [ 711-33-1 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3724 - 3735
  • 11
  • [ 67081-98-5 ]
  • [ 711-33-1 ]
Reference: [1] Patent: EP612734, 1994, A1,
  • 12
  • [ 709-63-7 ]
  • [ 74-88-4 ]
  • [ 64436-58-4 ]
  • [ 711-33-1 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 6, p. 2036 - 2040
  • 13
  • [ 402-43-7 ]
  • [ 711-33-1 ]
Reference: [1] Journal of Organometallic Chemistry, 1997, vol. 533, # 1-2, p. 13 - 23
  • 14
  • [ 592-02-9 ]
  • [ 329-15-7 ]
  • [ 711-33-1 ]
Reference: [1] Arzneimittel Forschung, 1964, vol. 14, p. 1324 - 1326
  • 15
  • [ 402-43-7 ]
  • [ 79-03-8 ]
  • [ 711-33-1 ]
Reference: [1] Canadian Journal of Chemistry, 1963, vol. 41, p. 1260 - 1264
  • 16
  • [ 42006-43-9 ]
  • [ 711-33-1 ]
  • [ 713-45-1 ]
Reference: [1] Chemical Communications, 2001, # 18, p. 1844 - 1845
  • 17
  • [ 79756-87-9 ]
  • [ 711-33-1 ]
  • [ 713-45-1 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 16, p. 5766 - 5767
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