[ CAS No. 26393-91-9 ] {[proInfo.proName]}

Name: 26393-91-9|1-(4-Fluorophenyl)-2-methylpropan-1-one|95%
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SKU: A254410
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Quality Control of [ 26393-91-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 26393-91-9 ]

Product Details of [ 26393-91-9 ]

CAS No. :	26393-91-9	MDL No. :	MFCD04038305
Formula :	C₁₀H₁₁FO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MHUVRVXSYXJUPK-UHFFFAOYSA-N
M.W :	166.19	Pubchem ID :	2782829
Synonyms :

Calculated chemistry of [ 26393-91-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.21
TPSA :	17.07 Å²

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) :	-5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	2.83
Log Po/w (WLOGP) :	3.08
Log Po/w (MLOGP) :	2.82
Log Po/w (SILICOS-IT) :	3.09
Consensus Log Po/w :	2.81

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.89
Solubility :	0.213 mg/ml ; 0.00128 mol/l
Class :	Soluble
Log S (Ali) :	-2.85
Solubility :	0.237 mg/ml ; 0.00142 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0603 mg/ml ; 0.000363 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 26393-91-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 26393-91-9 ]

* 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.

Downstream synthetic route of [ 26393-91-9 ]

[ 26393-91-9 ] Synthesis Path-Downstream 1~63

1
[ 26393-91-9 ]
[ 58472-44-9 ]

Yield	Reaction Conditions	Operation in experiment
		100.32 g (0.41 mol) of 2-bromo-1-(fluorophenyl)-2-methylpropan-1-one, prepared by brominating 1-(4-fluorophenyl)-2-methylpropane-1-one analogously to EP 3002, are dissolved in 80 ml of dry methanol. 24.3 g (0.45 mol) of sodium methoxide in a solvent mixture of 60 ml of dry methanol and 120 ml of chlorobenzene are added dropwise at 20C. The methanol is then distilled off and the residue is taken up with chlorobenzene. The salt is filtered off, and the chlorobenzene solution is concentrated. The liquid crude product, 90.8 g, is further purified by distillation, 60 C at 0.2 mmHg.

Reference： [1]Chemische Berichte,1983,vol. 116,p. 3631 - 3636
[2]Patent: EP1177182,2006,B1 .Location in patent: Page/Page column 18-19
[3]Journal of the American Chemical Society,2016,vol. 138,p. 12312 - 12315

2
[ 456-03-1 ]
[ 77-78-1 ]
[ 26393-91-9 ]
[ 79341-99-4 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 2866 - 2883

3
1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-(4-fluorophenyl)-1-ethanol [ No CAS ]
[ 26393-91-9 ]
[ 79341-86-9 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 11839 - 11852

4
[ 456-03-1 ]
[ 74-88-4 ]
[ 26393-91-9 ]
[ 79341-99-4 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 2866 - 2883

5
[ 50-00-0 ]
[ 26393-91-9 ]
[ 506-59-2 ]
[ 53207-35-5 ]

Reference： [1]Journal of Medicinal Chemistry,1974,vol. 17,p. 819 - 824

6
[ 26393-91-9 ]
[ 57-14-7 ]
[ 74-88-4 ]
[ 26393-89-5 ]

Reference： [1]Helvetica Chimica Acta,1977,vol. 60,p. 687 - 696

7
[ 462-06-6 ]
[ 79-31-2 ]
[ 26393-91-9 ]

Reference： [1]Helvetica Chimica Acta,1977,vol. 60,p. 687 - 696

8
[ 26393-91-9 ]
[ 103323-59-7 ]
[ 142874-48-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 559 - 573

Yield	Reaction Conditions	Operation in experiment
95%		EXAMPLE 7 1-(4-fluorophenyl)-2-methyl-1-propanone, O-(3-phenoxyphenylmethyl)oxime (7) This compound was prepared as an oil, 95% Z isomer, 5% E isomer, n22D = 1.5688, from the Z isomer of 1-(4-fluorophenyl)-2-methyl-1-propanone oxime and 3-phenoxybenzyl bromide, by the general procedure described in Example 1.

11
[ 26393-91-9 ]
[ 618-40-6 ]
2-(4-fluorophenyl)-1,3,3-trimethyl-3H-indolium perchlorate [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 1571 - 1574

12
[ 26393-91-9 ]
[ 142874-61-1 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 559 - 573

13
[ 26393-91-9 ]
[ 142873-26-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 559 - 573

14
[ 26393-91-9 ]
[ 142874-70-2 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 559 - 573

15
[ 403-42-9 ]
[ 26393-91-9 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 11839 - 11852

16
[ 26393-91-9 ]
[ 88539-00-8 ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 3631 - 3636

17
[ 26393-91-9 ]
[ 88539-02-0 ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 3631 - 3636

18
[ 1766-28-5 ]
[ 26393-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With Jones reagent; In acetone; at 0℃; for 0.166667h;	To a solution of 1-(4-Fluoro-phenyl)-2-methyl-propan-1-ol (1.6 g) in acetone (10 mL) at O C is added Jones reagent (20 mL) with stirring. After 10 minutes excess Jones reagent is destroyed by addition of isopropyl alcohol. Diethyl ether is added followed by anhydrous magnesium and the mixture is filtered and evaporated to give the product, a yellow oil (1.2 g).

Reference： [1]Patent: US6335350,2002,B1 .Location in patent: Example 972
[2]Patent: EP1137645,2004,B1 .Location in patent: Page 72
[3]Organic Letters,2018,vol. 20,p. 2906 - 2910

19
jones reagent [ No CAS ]
[ 1766-28-5 ]
[ 26393-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; acetone;	1 -(4-Fluoro-phenyl)-2-methyl-propan-1-one To a solution of 1-(4-Fluoro-phenyl)-2-methyl-propan-1-ol (1.6 g) in acetone (10 mL) at 0 C. is added Jones reagent (20 mL) with stirring. After 10 minutes excess Jones reagent is destroyed by addition of isopropyl alcohol. Diethyl ether is added followed by anhydrous magnesium and the mixture is filtered and evaporated to give the product, a yellow oil (1.2 g).

Reference： [1]Patent: US6166028,2000,A

20
O-(3-phenoxyphenylmethyl)oxime [ No CAS ]
1-(4-fluorophenyl)-2-methylpropan-1-one oxime [ No CAS ]
[ 51632-16-7 ]
[ 26393-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; methanol; dimethylformanide; toluene;	EXAMPLE 6 1-(4-fluorophenyl)-2-methyl-1-propanone, O-(3-phenoxyphenylmethyl)oxime (6) 1.8 g of 1-(4-fluorophenyl)-2-methyl-1-propanone oxime in 10 ml of 20% dimethylformanide in toluene was added to 0.5 g of sodium hydride (1.0 of a 50% dispersion in oil) in 20 ml of 20% dimethylformamide in toluene at 70-80 over a 10-minute period. A solution of 2.9 g of <strong>[51632-16-7]3-phenoxybenzyl bromide</strong> in 15 ml of 20% dimethylformamide in toluene was added over a 5-minute period. The mixture was stirred at 100-110 for 3 hours, and then was cooled to room temperature. 5 ml of methanol was added and the mixture was poured onto a mixture of ice and hydrochloric acid. The resulting mixture was extracted with diethyl ether. The extract was washed with 10% sodium bicarbonate solution, and dried (Na2 SO4). The solvent was evaporated and the residue was chromatographed on silica gel using toluene as eluent. Two fractions were obtained. After removal of the solvent, the first fraction was an oil, (6A), identified as a 3:1 mixture of the E and Z isomers of 6, n22D (refractive index) = 1.5740. On removal of solvent from the second fraction, an oil (6B) was obtained and identified as a 1:1 mixture of the E and Z isomers of 6, n22D = 1.5712.

Reference： [1]Patent: US4079149,1978,A

21
[ 16029-98-4 ]
[ 26393-91-9 ]
[1-(4-fluoro-phenyl)-2-methyl-propenyloxy]-trimethyl-silane [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 1922 - 1924

22
[ 26393-91-9 ]
[ 1355254-03-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 1922 - 1924

23
[ 26393-91-9 ]
2,2-dimethyl-5-fluoro-1-indanone [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 1922 - 1924

24
[ 26393-91-9 ]
[ 1001319-04-5 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 4561 - 4564

25
[ 26393-91-9 ]
[ 1364975-40-5 ]
1-((S)-1,2-Dimethyl-propyl)-4-fluoro-benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 4561 - 4564

26
[ 26393-91-9 ]
[ 2065-66-9 ]
[ 28115-05-1 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 4561 - 4564

27
[ 1194-02-1 ]
[ 920-39-8 ]
[ 26393-91-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 4561 - 4564
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 2729 - 2733
Angew. Chem.,2015

28
[ 78-82-0 ]
potassim 4-fluorophenyltrifluoroborate [ No CAS ]
[ 26393-91-9 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5273 - 5281

29
[ 1283075-99-9 ]
[ 920-39-8 ]
[ 26393-91-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 743 - 746

30
[ 459-57-4 ]
[ 26393-91-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 743 - 746
[2]Organic Letters,2018,vol. 20,p. 2906 - 2910

31
[ 67-56-1 ]
[ 456-03-1 ]
[ 26393-91-9 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 3576 - 3579
[2]Angewandte Chemie - International Edition,2014,vol. 53,p. 761 - 765
Angew. Chem.,2014,vol. 126,p. 908

32
[ 26393-91-9 ]
[ 335287-91-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-Bromosuccinimide; dimethyl sulfoxide; at 60℃; for 24h;Schlenk technique;	Taking a 25 ml Schlenk reaction tube, adding N - bromo succimide (NBS) 18 mg (0.1mmol) as catalyst, 2 - methyl -1 - chloro phenyl acetone 84 mg (0.5mmol), dimethyl sulfoxide (DMSO) 1 ml as the oxidizing agent, carbonylating and solvent, for 100 C stirring for 24 hours. After the reaction by adding ethyl acetate 15 ml, salt water 3 ml, ethyl acetate 3 times, the combined organic phase, column chromatography separation to obtain 2 - hydroxy -2 - methyl -1 - chloro phenyl acetone pure product 68 mg, yield 75%.

Reference： [1]Organic Letters,2015,vol. 17,p. 876 - 879
[2]Patent: CN104710256,2017,B .Location in patent: Paragraph 0178-0181

33
[ 26393-91-9 ]
2-(4-fluorophenyl)-2-isopropyloxirane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2729 - 2733
Angew. Chem.,2015

34
[ 26393-91-9 ]
[ 1779-49-3 ]
[ 28115-05-1 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2729 - 2733
Angew. Chem.,2015

35
[ 26393-91-9 ]
1-(4-fluorophenyl)-2,2-dimethyl-3-phenylpropan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12312 - 12315

36
[ 26393-91-9 ]
1-(4-fluorophenyl)-3-(4-methoxyphenyl)-2,2-dimethylpropan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12312 - 12315

37
[ 403-42-9 ]
[ 74-88-4 ]
[ 26393-91-9 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5940 - 5943

38
[ 26393-91-9 ]
[ 171364-80-0 ]
methyl 5'-fluoro-2'-isobutyrylbiphenyl-4-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5940 - 5943

39
[ 26393-91-9 ]
4-chloro-1-(4-fluorophenyl)-2,2-dimethylpent-4-en-1-one oxime [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2906 - 2910

40
[ 26393-91-9 ]
2-(chloromethyl)-5-(4-fluorophenyl)-4,4-dimethyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-3,4-dihydro-2H-pyrrole 1-oxide [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2906 - 2910

41
[ 39557-31-8 ]
[ 26393-91-9 ]
C₁₃H₁₄ClFO [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2906 - 2910

42
[ 26393-91-9 ]
5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)-N-(1-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: WO2018/165520,2018,A1

43
[ 26393-91-9 ]
1-(4-fluorophenyl)-2-methylpropan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		To a stirred solution of compound DE (3.0 g, 18.0 mmol) in MeOH (30 mL), ammonium acetate (14.0 g, 180 mmol) was added and the reaction mixture was stirred at RT for 30 min. Sodium cyano borohydride (2.26 g, 36.1 mmol) was added and the reaction mixture was stirred at RT for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with IN HC1 solution and extracted with EtOAc. The aqueous layer basified with 10% NaOH solution and extracted with 10% MeOH/DCM. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford compound DF (1.0 g, 33%) as a thick oil. LC-MS: m/z 168.05 [M+H]+.

Reference： [1]Patent: WO2018/165520,2018,A1 .Location in patent: Page/Page column 161-162

44
[ 26393-91-9 ]
2-((1-(4-fluorophenyl)-2-methylpropyl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/165520,2018,A1

45
[ 26393-91-9 ]
N-(1-(4-fluorophenyl)-2-methylpropyl)-5-(1H-tetrazol-5-yl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: WO2018/165520,2018,A1

46
[ 462-06-6 ]
[ 79-30-1 ]
[ 26393-91-9 ]

Yield	Reaction Conditions	Operation in experiment
40%		To the solution of anhydrous A1C13 (13.8 g, 104 mmol) in DCM (10 mL) at 0C, was added drop wise a solution of isobutyryl chloride (8.5 mL, 78.1 mmol) in DCM (25 mL) and the reaction mixture was stirred at RT for 1H. To this a reaction mixture, a solution of fluorobenzene (CV, 5.0 g, 52.0 mmol) in DCM (15 mL) was added drop wise and stirred at RT for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by column chromatography using 5% EtOAc/hexane to afford compound DE (3.5 g, 40%) as an off white solid. LC-MS: m/z 166.96 [M+H]+.

Reference： [1]Patent: WO2018/165520,2018,A1 .Location in patent: Page/Page column 161

47
[ 26393-91-9 ]
[ 127-09-3 ]
1-(4-fluorophenyl)-2-methylpropan-1-one O-acetyl oxime [ No CAS ]
1-(4-fluorophenyl)-2-methylpropan-1-one O-acetyl oxime [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 14713 - 14722

48
[ 2403-57-8 ]
[ 70001-45-5 ]
[ 26393-91-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 971 - 975

49
[ 26393-91-9 ]
5-(4-fluorophenyl)-2,4,4-trimethyl-3,4-dihydro-2H-pyrrole 1-oxide [ No CAS ]
5-(4-fluorophenyl)-2,4,4-trimethyl-3,4-dihydro-2H-pyrrole 1-oxide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 12620 - 12627

50
[ 26393-91-9 ]
5-(4-fluorophenyl)-2,4,4-trimethyl-3,4-dihydro-2H-pyrrole 1-oxide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 12620 - 12627

51
[ 26393-91-9 ]
(Z)-1-(4-fluorophenyl)-2,2-dimethylpent-4-en-1-one oxime [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 12620 - 12627

52
[ 26393-91-9 ]
[ 106-95-6 ]
1-(4-fluorophenyl)-2,2-dimethylpent-4-en-1-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 12620 - 12627

53
[ 75-75-2 ]
[ 26393-91-9 ]
[ 6091-44-7 ]
1-(4-fluorophenyl)-2,2-dimethyl-3-(piperidin-1-yl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With 1,3-DIOXOLANE; at 90℃; for 24h;Sealed tube;	A mixture of l-(4-fluorophenyl)-2-methylpropan-l-one (150 mg, 0.90 mmol), <strong>[6091-44-7]<strong>[6091-44-7]piperidine</strong> hydrochloride</strong> (131 mg, 1.08 mmol) and methanesulfonic acid (9 mg, 0.09 mmol) in 1,3- dioxolane (2 mL) was stirred at 90C in sealed tube for 24 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was diluted with hydrochloric acid (0.3 M 50 mL) and washed with ethyl acetate (4 X 50 mL) to remove most of impurities. The aqueous layer was adjusted to pH 9 with saturated sodium carbonate and extracted with ethyl acetate (50 mL). The organic layer was washed with water, brine (60 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a residue which was purified through silica gel flash column chromatography (eluted with 30% ethyl acetate in hexane) to affordl-(4-fluorophenyl)-2,2-dimethyl-3-(piperidin-l-yl)- propan-l-one (30 mg, 13%) as a colorless oil. LCMS: (ES+): m/z 264.2 [M+H] +. tR = 1.94 min; JH NMR (400 MHz, CDCl3): d 1.27 (s, 6H), 1.33-1.37 (m, 2H), 1.44-1.49 (m, 4H), 2.37 (m, d, J = 5.2 Hz, 4H), 2.60 (s, 2H), 7.04-7.09 (m, 2H), 7.80-7.84 (m, 2H).

Reference： [1]Patent: WO2019/195775,2019,A1 .Location in patent: Page/Page column 39; 41

54
[ 456-22-4 ]
[ 26393-91-9 ]

Reference： [1]Patent: WO2019/195775,2019,A1

55
[ 403-43-0 ]
[ 26393-91-9 ]

Reference： [1]Patent: WO2019/195775,2019,A1

56
[ 920-39-8 ]
[ 116332-54-8 ]
[ 26393-91-9 ]