[ CAS No. 347-93-3 ] {[proInfo.proName]}

Name: 347-93-3|3-Chloro-1-(4-fluorophenyl)propan-1-one|97%
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Quality Control of [ 347-93-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 347-93-3 ]

CAS No. :	347-93-3	MDL No. :	MFCD00000991
Formula :	C₉H₈ClFO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AAHQPLJUSLMHHR-UHFFFAOYSA-N
M.W :	186.61	Pubchem ID :	67672
Synonyms :

Calculated chemistry of [ 347-93-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.2
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) :	-5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	2.23
Log Po/w (WLOGP) :	3.06
Log Po/w (MLOGP) :	2.82
Log Po/w (SILICOS-IT) :	3.42
Consensus Log Po/w :	2.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.57
Solubility :	0.498 mg/ml ; 0.00267 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	1.11 mg/ml ; 0.00597 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.05
Solubility :	0.0166 mg/ml ; 0.0000887 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.32

Safety of [ 347-93-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 347-93-3 ]

* 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 [ 347-93-3 ]
Downstream synthetic route of [ 347-93-3 ]

[ 347-93-3 ] Synthesis Path-Upstream 1~4

1
[ 347-93-3 ]
[ 1481-32-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2142 - 2148

2
[ 347-93-3 ]
[ 700-84-5 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1973, p. 3092 - 3095
[2] Patent: WO2011/14613, 2011, A2, . Location in patent: Page/Page column 11
[3] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760

3
[ 462-06-6 ]
[ 625-36-5 ]
[ 347-93-3 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, p. 1169 - 1172[2] Zhurnal Obshchei Khimii, 1967, vol. 37, p. 1233 - 1236
[3] Canadian Journal of Research, 1933, vol. 8, p. 440,444
[4] Bulletin de la Societe Chimique de France, 1973, p. 3092 - 3095
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 3924 - 3926
[6] Journal of Medicinal Chemistry, 2008, vol. 51, # 13, p. 3841 - 3855
[7] Patent: WO2011/14613, 2011, A2, . Location in patent: Page/Page column 11
[8] Patent: US2012/277423, 2012, A1, . Location in patent: Page/Page column 25
[9] Organic and Biomolecular Chemistry, 2016, vol. 14, # 16, p. 3883 - 3888
[10] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760

4
[ 625-36-5 ]
[ 460-00-4 ]
[ 347-93-3 ]

Reference： [1] Journal of Fluorine Chemistry, 2015, vol. 173, p. 63 - 68

[ 347-93-3 ] Synthesis Path-Downstream 1~74

1
[ 462-06-6 ]
[ 625-36-5 ]
[ 347-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; In dichloromethane; at 25 - 30℃; for 12h;Inert atmosphere;	AICI3 (9.02 g) and dichloromethane (DCM, 50 ml_) are charged into a round bottomed flask under a nitrogen atmosphere. Chloropropionyl chloride (7.93 g) is added over 20 minutes at 25-300C. Fluorobenzene (5 g) is added over about 15 minutes at 300C. The mixture is maintained at 25-30C for about 12 hours. After reaction completion, water (50 ml_) is added slowly and the mixture is stirred for 15 minutes. The aqueous layer is separated and extracted with DCM (50 ml_). The combined organic layers are dried with sodium sulphate and distilled under vacuum below 500C. n-Hexane (15 ml_) is added to the residue and stirred for 20 minutes. The solid is filtered and washed with 10 ml_ of n-hexane (10 ml_). The wet solid is dried, to obtain 6.9 g of 3-chloro-1 -(4-fluorophenyl)-propan-1 -one.
		Example 111-(3-chloropropionyl)-4-fluorobenzene 8178 2-chloroethylpropionyl chloride (0.63 g), fluorobenzene (0.48 g), and aluminium chloride (0.8 g) were reacted in nitrobenzene (2.3 mL) at 0 C., followed by treatment with hydrochloric acid to obtain the title compound (0.2 g).NMR (CDCl3) 3.5 (m, 2H), 4.3 (m, 2H), 7.2-8.1 (m, 4H)TG 49.6 (3 mumol) 22.4 (10 mumol) 5.6 (30 mumol)

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 9488 - 9520
[2]Journal of general chemistry of the USSR,1967,vol. 37,p. 1169 - 1172
Zhurnal Obshchei Khimii,1967,vol. 37,p. 1233 - 1236
[3]Bulletin de la Societe Chimique de France,1973,p. 3092 - 3095
[4]Journal of Medicinal Chemistry,2004,vol. 47,p. 3924 - 3926
[5]Journal of Medicinal Chemistry,2008,vol. 51,p. 3841 - 3855
[6]Patent: WO2011/14613,2011,A2 .Location in patent: Page/Page column 11
[7]Patent: US2012/277423,2012,A1 .Location in patent: Page/Page column 25
[8]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3883 - 3888
[9]Chemical Communications,2016,vol. 52,p. 8757 - 8760
[10]Chemistry and biodiversity,2019,vol. 16

2
[ 347-93-3 ]
[ 700-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 115 - 120℃; for 0.5h;Inert atmosphere;	3-Chloro-1 -(4-fluorophenyl)-propan-1 -one (10 g) and concentrated sulfuric acid (60 ml_) are charged into a 250 ml_ round bottom flask equipped with nitrogen gas flow and heated to 120C. The mixture is stirred for about 30 minutes at 1 15- 120C. Reaction completion is confirmed using thin layer chromatography (TLC). The reaction mixture is poured into ice water (30 mL) followed by stirring for about 15 minutes. The mass is extracted with chloroform (150 mL) and the organic layer is concentrated under reduced pressure below 500C. The obtained residue is purified by column chromatography using silica gel and n-hexane/ethyl acetate as a gradient eluent, to obtain 3.7 g of the title compound.

Reference： [1]Bulletin de la Societe Chimique de France,1973,p. 3092 - 3095
[2]Patent: WO2011/14613,2011,A2 .Location in patent: Page/Page column 11
[3]Chemical Communications,2016,vol. 52,p. 8757 - 8760

3
[ 4735-50-6 ]
[ 347-93-3 ]
1-(4-Fluoro-phenyl)-3-(2-naphthalen-1-yl-ethylamino)-propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran for 6h; Heating;

Reference： [1]Wilkerson; DeLucca; Galbraith; Kerr [European Journal of Medicinal Chemistry, 1992, vol. 27, # 6, p. 595 - 610]

4
[ 347-93-3 ]
[ 4159-04-0 ]
3-(p-fluorobenzoyl)-7H-benz<de>anthracene-7-one [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1982,vol. 20,p. 459 - 474

5
[ 347-93-3 ]
[ 2017-68-7 ]
1-(4-Fluoro-phenyl)-3-(2-naphthalen-2-yl-ethylamino)-propan-1-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 595 - 610

6
[ 347-93-3 ]
[ 37529-30-9 ]
3-(4-Decyl-phenylamino)-1-(4-fluoro-phenyl)-propan-1-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 595 - 610

7
[ 347-93-3 ]
[ 929-73-7 ]
[ 143667-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran for 6h; Heating;

Reference： [1]Wilkerson; DeLucca; Galbraith; Kerr [European Journal of Medicinal Chemistry, 1992, vol. 27, # 6, p. 595 - 610]

8
[ 347-93-3 ]
[ 1481-32-9 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2142 - 2148

9
[ 347-93-3 ]
[ 31736-75-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h;Inert atmosphere;	INTERMEDIATE 17 PREPARATION OF 3-CHLORO-1-(4-FLUOROPHENYL)PROPAN-1-OL NaBH4 (200 mg, 5.37 mmol) was added portionwise to a solution of 3-chloro-1-(4- fluorophenyl)propan-1-one (1g, 5.37 mmol) in MeOH (10 mL) at 0 C. The reaction mixture was allowed to reach room temperature and stirred at this temperature for 1 h. A sat. NH4Cl solution was added and the mixture was stirred at 0 C for 20 min, then extracted twice with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (cyclohexane-EtOAc, 100:0 to 50:50) to afford title compound (830 mg, 82% yield) as colorless oil.1H NMR (400 MHz, CDCl3) delta 7.40-7.31 (m, 2H), 7.13- 7.01 (m, 2H), 4.97 (dt, J=8.4, 4.1 Hz, 1H), 3.76 (ddd, J=10.9, 8.3, 5.5 Hz, 1H), 3.57 (dt, J=11.0, 5.9 Hz, 1H), 2.24 (ddt, J=14.4, 8.5, 5.7 Hz, 1H), 2.14- 2.02 (m, 2H). LC-MS (Method A): m/z = 171.0 [M- H2O]+, 0.97 min.
	With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at -10 - -5℃; for 0.166667h;	General procedure: Starting materials 7 or 8, respectively (1 mmol) was dissolved in THF (1 mL) and EtOH (1 mL) was added. The mixture was cooled to -10 C and NaBH4 (1.05 mmol) was slowly added at this temperature.The solution was stirred at -5 C for 10 min and thereafter, poured into a mixture of saturated aqueous ammonium chloride (3 mL) in ice (1.5 g). The product was extracted with diethyl ether, dried over Na2SO4 and evaporated to dryness. The crude product was employed directly in the subsequent reaction step without further purification.

Reference： [1]Patent: WO2017/96301,2017,A1 .Location in patent: Page/Page column 90
[2]Synthesis,2011,p. 2921 - 2928
[3]Journal of the Chemical Society. Chemical communications,1986,p. 1018 - 1019
[4]Journal of Medicinal Chemistry,2003,vol. 46,p. 5512 - 5532
[5]Journal of Medicinal Chemistry,2004,vol. 47,p. 3924 - 3926
[6]Journal of Medicinal Chemistry,2008,vol. 51,p. 3841 - 3855
[7]Molecules,2015,vol. 20,p. 1712 - 1730
[8]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3883 - 3888

10
[ 347-93-3 ]
[ 51594-59-3 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 4537 - 4541
[2]European Journal of Medicinal Chemistry,1991,vol. 26,p. 667 - 676
[3]Organic Letters,2018,vol. 20,p. 6564 - 6568
[4]Organic Letters,2020

11
[ 347-93-3 ]
[ 58088-57-6 ]
1-(4-Fluoro-phenyl)-3-[(phenyl-pyridin-4-yl-methyl)-amino]-propan-1-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 595 - 610

12
[ 347-93-3 ]
[ 126712-07-0 ]
3-(2-Bromo-6-methoxy-benzylamino)-1-(4-fluoro-phenyl)-propan-1-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 935 - 938

13
[ 347-93-3 ]
[ 200004-39-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dimethylsulfide borane complex; C27H26BNO3; In tetrahydrofuran; at 20℃; for 6.5h;	The cat-3 (0.03 mmol, 25 mg) prepared in Preparation Example 2.3 was dissolved in 1 ml of THF, and BH3-DMS (0.38 mmol, 0.04 ml) was added thereto. . To the reaction mixture was added dropwise a solution of <strong>[347-93-3]3-chloro-4'-fluoropropiophenone</strong> (0.54 mmol, 100 mg) in 0.45 mL of THF dropwise over 30 minutes. After 6 hours of reaction at room temperature, methanol was added to terminate the reaction. After removal of the solvent, ethyl acetate and water were added to separate the organic layer. Ethyl acetate was added to the separated aqueous layer to further extract it. The extracted organic layers were combined, dried over Na2SO4, and filtered. The resulting filtrate was concentrated and purified by column chromatography (hexane: ethyl acetate = 3: 1)And purified to obtain (R) -3-chloro-1- (4-fluorophenyl) -1-propanol (yield: 71%).

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 10281 - 10283
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 101 - 104
[3]Patent: KR2015/116956,2015,A .Location in patent: Paragraph 0181-0183
[4]Synthesis,2011,p. 2921 - 2928
[5]Synthesis,2011,p. 2921 - 2928

14
[ 37656-48-7 ]
[ 347-93-3 ]
1-(4-fluoro-phenyl)-3-[4-(4-fluoro-phenyl)-piperidin-1-yl]-propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 495 - 500

15
[ 347-93-3 ]
[ 104-94-9 ]
[ 37155-08-1 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

16
[ 936-44-7 ]
[ 347-93-3 ]
1-(4-fluoro-phenyl)-3-(3-phenyl-pyrrolidin-1-yl)-propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4667 - 4678

17
[ 3973-62-4 ]
[ 347-93-3 ]
1-(4-fluorophenyl)-3-(3-phenylpiperidin-1-yl)propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4667 - 4678

18
[ 31251-28-2 ]
[ 347-93-3 ]
1-(4-fluoro-phenyl)-3-(3,4,5,6-tetrahydro-2<i>H</i>-[3,3']bipyridinyl-1-yl)-propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4667 - 4678

19
[ 40864-10-6 ]
[ 347-93-3 ]
1-(4-fluorophenyl)-3-(3-pyridin-2-ylpiperidin-1-yl)propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4667 - 4678

20
[ 630121-84-5 ]
[ 347-93-3 ]
[ 861965-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 16h;	EXAMPLE 75E 1-(4-fluorophenyl)-3-[3-(1,3-thiazol-2-yl)piperidin-1-yl]propan-1-one 3-Chloro-4'fluoropropiophenone (0.465 g, 2.5 mmol), the product from Example 75D (0.42 g, 2.5 mmol), K2CO3 (0.348 g, 2.5 mmol), and NaI (0.37 g, 2.5 mmol) and were combined in DMF(5 mL) and stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate (30 mL) and washed with brine. The organic layer was dried with MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 1:9 ethanol:ethyl acetate) to provide the title compound.

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4667 - 4678
[2]Patent: US2005/176727,2005,A1 .Location in patent: Page/Page column 41

21
[ 862718-70-5 ]
[ 347-93-3 ]
1-(4-fluorophenyl)-3-[3-(pyridin-2-yloxy)piperidin-1-yl]propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; sodium iodide In N,N-dimethyl-formamide Heating;

Reference： [1]Wang, Xueqing; Bhatia, Pramila A.; Daanen, Jerome F.; Latsaw, Steve P.; Rohde, Jeffrey; Kolasa, Teodozyi; Hakeem, Ahmed A.; Matulenko, Mark A.; Nakane, Masaki; Uchic, Marie E.; Miller, Loan N.; Chang, Renjie; Moreland, Robert B.; Brioni, Jorge D.; Stewart, Andrew O. [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 15, p. 4667 - 4678]

22
[ 347-93-3 ]
[ 200004-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With (-)-diisopinocampheyl chloride; In hexane; at -25 - 20℃;	A solution of 3-Chloro-4'-fluoropropiophenone (5.4mmol) was slowly added to 1.6M solution of (-)-chlorodiisopinocampheylborane in Hexane (delta.lmmol) at - 250C. This reaction mixture was stirred at room temperature for 16h. After 16h stirring at -250C, MeOH was added to terminate the reaction, then it was washed with brine, and the resulting organic layer was dried and concentrated in vacuo. The crude product was dissolved in 2OmL of acetonitrile and was added 4-amino-5-chloro-2- methoxy-N-[(piperidin-4-yl)methyl]benzamide (3.6mmol), potassium carbonate (5.4mmol), and potassium iodide (5.4mmol) at 25 s C. The reaction mixture was refluxed for 12h. This solution was then concentrated on a rotary evaporator and diluted with ethylacetate, washed with brine, the resulting organic layer was dried and purified by column chromatography. The resulting (S)-4-amino-5-chloro-N-[[l-[3-(4- fluorophenyl)-3-hydroxypropyl]piperidin-4-yl]methyl]-2-methoxybenzamide was dissolved in MC and the solution treated with a solution of HCl in ether. The resulting precipitate was filtered to give the title compound.[0186] IH-NMR (CDC13, 200MHz) 58.1(s, IH), 7.8(m, IH), 7.4-7.3(m, 2H), 7.1-7.0(m, 2H), 6.35(s, IH), 4.9(m, IH), 4.4(s, 2H), 3.9(s, 3H), 3.4-3. l(m, 4H), 2.9- 2.7(m, 2H), 2.4-2.0(m, 2H), 1.9-1.7(m, 5H), 1.7-1.5(m, 2H)
	With (-)-B-chlorodiisopinocampheylborane;	Treatment of commercially available 3-chloro-4'- fluoropropiophenone (82) with diisopinocamphenylchloroborane, (Srebnik, M.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1988, 53, 2916-2920), gives [£]-(- )-3-chloro-l-(4-fluorophenyl)propanol (83a). Treatment of 83a with tert- butyldimethylsilyl chloride and imidazole gives 83b. Reaction of 83b with sodium mercaptoacetate in the presence of DBU gives 84. Compound 84 is converted to the corresponding mixed anhydride by treatment with pivaloyl chloride and DMAP in DMF and then coupled to (S)-4-phenyl-2-oxazolidinone to afford the imide (85). In the next step, 85 is treated with titanium tetrachloride and N-ethyldiisopropylamine followed by treatment with 6b to effect enantiospecific condensation providing 86. Treatment of 86 with excess N, O-bis(trimethylsilyl)acetamide followed by a catalytic amount of tetrabutylammonium fluoride hydrate results in ring closure to the desired beta-lactam (87) while maintaining the TBS protecting group on the benzylic alcohol. Suzuki coupling of 87 with 11 gives the expected biphenyl derivative that is deprotected by hydrogenolysis over palladium on carbon, treatment with bromotrimethylsilane, and treatment with aqueous HF to give the product 88. Using the methods described above compounds 89 and 90 can also be prepared from key intermediate 87.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 101 - 104
[2]Organic and Biomolecular Chemistry,2016,vol. 14,p. 4304 - 4311
[3]Patent: WO2010/44585,2010,A2 .Location in patent: Page/Page column 42-43
[4]Patent: WO2006/121861,2006,A2 .Location in patent: Page/Page column 198

23
[ 347-93-3 ]
[ 61869-08-7 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

24
[ 347-93-3 ]
[ 200572-33-4 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

25
[ 347-93-3 ]
[ 200572-35-6 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

26
[ 347-93-3 ]
[ 125224-43-3 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

27
[ 347-93-3 ]
[ 607375-33-7 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

28
[ 347-93-3 ]
(4S)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-piperidin-2-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

29
[ 347-93-3 ]
[ 607375-35-9 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

30
[ 347-93-3 ]
[ 607375-34-8 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11253 - 11258

31
[ 347-93-3 ]
[ 52085-92-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1973,p. 3092 - 3095

32
[ 861965-58-4 ]
[ 347-93-3 ]
[ 861965-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium chloride; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 24h;	EXAMPLE 67C 1-(4-fluorophenyl)-3-(3-pyrazin-2-ylpyrrolidin-1-yl)propan-1-one The product from Example 67B (0.40 g, 2.7 mmol), sodium iodide (0.4 g, 2.7 mmol), cesium chloride (0.97 g, 3.0 mmol), and <strong>[347-93-3]3-chloro-4'-fluoropropiophenone</strong> (0.5 g, 2.7 mmol) were combined in DMF (20 mL) and stirred at room temperature for 24 hours. The mixture was poured into ethyl acetate (100 mL) and washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, CH2CL2 to 5% MeOH/CH2Cl2) to afford the title compound. 1H NMR (300 MHz, CDCl3) delta 2.12 (m, 1H), 2.36 (m, 1H), 3.06 (m, 8H), 3.60 (m, 1H), 3.58 (m, 1H), 7.15 (t, J=12 Hz, 2H), 8.00 (m, 2H), 8.42 (d, J=3 Hz, 1H), 8.54 (m, 2H); MS (DCI/NH3) m/z 300 (M+H)+.

Reference： [1]Patent: US2005/176727,2005,A1 .Location in patent: Page/Page column 37

33
[ 21767-35-1 ]
[ 347-93-3 ]
[ 861965-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium chloride; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 16h;	EXAMPLE 70C 1-(4-fluorophenyl)-3-{3-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}propan-1-one The product from Example 70B (0.70 g, 3.30 mmol), sodium iodide (0.03 g, 2.0 mmol), cesium chloride (1.16 g, 3.6 mmol), and 3-Chloro-4'-fluoropropiophenone (0.61 g, 3.3 mmol) were combined in DMF (10 mL) and stirred at room temperature for 16 hours. The mixture was poured into ethyl acetate (100 mL) and washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, CH2CL2 to 10% MeOH/CH2Cl2) to afford the title compound. 1H NMR (300 MHz, CDCl3) delta 1.87 (m, 1H), 2.36 (m, 1H), 2.62 (t, J=9 Hz, 1H), 2.81 (t, J=9 Hz, 1H), 3.09 (m, 6H), 3.36 (m, 1H), 7.15 (t, J=12 Hz, 2H), 7.39 (m, 3H), 7.99 (m, 3H); MS (DCI/NH3) m/z 366 (M+H)+.

Reference： [1]Patent: US2005/176727,2005,A1 .Location in patent: Page/Page column 38-39

34
[ 91246-24-1 ]
[ 347-93-3 ]
[ 861965-64-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 17h;	EXAMPLE 72D 1-(4-fluorophenyl)-3-[3-(2-methoxyphenyl)pyrrolidin-1-yl]propan-1-one The product from Example 72C (210 mg, ~1.2 mmol), 3-chloro-4'-fluoro-propiophenone (330 mg, 1.7 mmol), potassium carbonate (220 mg, 1.6 mmol), and sodium iodide (240 mg 1.6 mmol) were combined in DMF (2 mL) and stirred at room temperature for 17 hours. The mixture was diluted with dichloromethane (5 mL), washed with water, brine, dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. MS (DCI/NH3) m/z 328 (M+H)+.

Reference： [1]Patent: US2005/176727,2005,A1 .Location in patent: Page/Page column 39

35
[ 347-93-3 ]
[ 54060-30-9 ]
[ 867216-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 65℃; for 14h;Heating / reflux;	Synthesis of N-[2-(4-Fluorobenzoyl)ethyl]-3-ethynylaniline (Compound 305a) [0332] 3-Ethynylaniline 301a (2.68 g, 22.8 mmol) was heated with 3-chloro-4'- fluoropropiophenone 303a (3.86 g, 20.7 mmol) and triethylamine (3.85 mL, 24.7 mmol) in tetrahydrofuran (40 mL) at 65 C for 14h. The reaction mixture was concentrated to a small volume, diluted with ethyl acetate and then washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated to a small volume. Upon cooling white crystals formed. These were filtered off to give N-[2-(4-fluorobenzoyl)ethyll-3- ethynylaniline 305a, (1.98 g). ¹H NMR (CDCl3) No. 7.94-7.99 (m, 2H), 7.08-7.15 (m, 3H), 6.83- 6.87 (m, 1 H), 6.76 (m,lH), 6.61-6.64 (m,lH), 3.61 (t, J=6.0,2H) , 3.25 (t, J=6.0,2H), 3.02 (s, 1H). MS (m/z): 268 (MH+) confirmed by LC-MS, tr= 14.36 min (Method Y)

Reference： [1]Patent: WO2005/97760,2005,A1 .Location in patent: Page/Page column 91; 7/24

36
[ 867215-91-6 ]
[ 347-93-3 ]
[ 867216-81-7 ]

Yield	Reaction Conditions	Operation in experiment
11%		3-Chloro-4'-fluoropropiophenone 303a (220 mg, 1.2 mmol) was added to a mixture of 3- (2,6-dichlorophenyl)-5-(5-amino-2-pyridyl)isoxazole 601a (400 mg, 1.2 mmol) and triethylamine (0.3 mL, 2.4 mmol) in acetonitrile (40 mL). The solution was heated at reflux. After two hours a second portion of 3-chloro-4' fluoropropiophenone (220 mg, 1.2 mmol) was added, along with a second portion of triethylamine (0.3 mL, 2.4 mmol). After stirring at reflux overnight, the reaction mixture was cooled to room temperature and then washed successively with water, 10% hydrochloric acid and saturated sodium bicarbonate solution. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by prep-scale reverse phase high performance liquid chromatography to give 603a as a white solid (60 mg, 11%). ¹H NMR (300 MHz, CDC13): 8.33 (m, 1H), 8.00 (m, 2H), 7.39 (m, 5H), 7.17 (m, 2H), 6.64 (m, 1H), 3.81 (m, 2H), 3.38 ppm (m, 2H).

Reference： [1]Patent: WO2005/97760,2005,A1 .Location in patent: Page/Page column 94; 10/24

37
[ 347-93-3 ]
[ 141-52-6 ]
[ 1068-90-2 ]
[ 5887-66-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol;	a Diethyl acetamido[2-(4-fluorobenzoyl)-ethyl]malonate To a stirred solution of diethyl acetaminomalonate (4.34 g, 0.02 mol) in EtOH (30 ml) was added at room temperature sodium ethanolate (1.46 g, 20.4 mmol) and subsequently 3-chloro-4'-fluoro-propiophenone (3.73 g, 0.02 mol). The reaction mixture was heated under reflux conditions for 5 h, poured onto ice-water (70 ml), acidified (25 ml 3N sulfuric acid) and extracted with ethyl acetate (2*100 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated to give a brown oil (7.95 g). Crystallization from ethyl acetate/hexane yielded diethyl acetamido[2-(4-fluorobenzoyl)-ethyl]malonate (5.72 g, yield 78%) as an off-white solid, m. p. 73 C.

Reference： [1]Patent: US2002/19424,2002,A1

38
[ 160419-40-9 ]
[ 347-93-3 ]
5-methoxy-3-[N-(3-(4-fluoro-phenyl)-3-oxo-propyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether; dichloromethane; ethyl acetate; acetone;	EXAMPLE 3 5-methoxy-3-[N-(3-(4-fluoro-phenyl)-3-oxo-propyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole (Compound 11) Triethylamine (0.9 ml; 0.0063 mol) was added to a solution of <strong>[347-93-3]3-chloro-4'-fluoropropiophenone</strong> (1.2 g; 0.0063 mol) in diethyl ether (10 ml). The resulting mixture was stirred for 3 hours at room temperature. Then the mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken up with a mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (0.79 g; 0.0028 mol), triethylamine (0.8 ml; 0.0057 mol) in methylene chloride (20 ml). The reaction mixture was refluxed for 4 hours. Then the reaction was concentrated under vacuum and the residue was triturated with 1N hydrochloric acid. The aqueous phase was decanted, and the guming solid was twice washed with water and triturated with diethyl ether. The title compound hydrochloride was collected by filtration, washed with diethyl ether and recrystallized with a mixture (1/2) of ethyl acetate/acetone. 0.86 g of the desired compound were obtained. Mp 186-188 C. 1 H NMR (DMSO+CDCl3) delta=10.79 (b, 1H), 10.45 (b, 1H), 8.08 (m, 2H), 7.40 (m, 2H), 7.23 (d, 1H), 7.18 (d, 1H), 6.98 (d, 1H), 6.72 (m, 1H), 5.80 (b, 1H); MS (C.I.): [M+H]+ 393 m/z Following the above described process and using the appropriate halide, the following compound was prepared:

Reference： [1]Patent: US5834493,1998,A

39
[ 347-93-3 ]
[ 104-42-7 ]
3-[(4-Dodecylphenyl)-amino]-1-(4-fluorophenyl)-1-propanone Hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether;	A. 3-[(4-Dodecylphenyl)-amino]-1-(4-fluorophenyl)-1-propanone Hydrochloride. A mixture of <strong>[104-42-7]4-dodecylaniline</strong> (26.2 g, 0.1 mole) and 3-chloro-4'-fluoropropiophenone (18.7 g, 0.1 mole) in diethyl ether (200 ml) was stirred for 16 hours at room temperature. The mixture was treated with triethylamine (10.1 g, 0.1 mole), stirred for an additional 72 hours, and concentrated in vacuo. The residue was partitioned between diethyl ether (200 ml) and hydrochloric acid (IN, 200 ml). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to an impure tacky solid (41.9 g). A small portion (5 g) was recrystallized from ethanol to give the title compound (4.0 g); mp 107-109 C.; IR(nujol) C=O a 1674 cm-1; NMR(DMSO-d6, TMS): delta0.5-1.7(m,23H,C11 H23), 2.50(t,2H,ArCH2), 3.30(m,4H, N--CH2 --CH2), 6.50,7.00(2d,4H,p-N-phenyl), [ 7.37(d of d,2H) and 8.07(m,2H) p-F-phenyl]; Anal. Calcd. for C27 H38 FNO.HCl, MW 448.05: C,73.37; H,8.77; N,3.19. Found: C,73.09; H,8.50; N,3.19. Mass spectrum m/e 411,284.

Reference： [1]Patent: US5039706,1991,A

40
[ 24050-16-6 ]
[ 347-93-3 ]
1-(4-fluorophenyl)-3-(2-methyl-3-thiazolidinyl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.00 g (29.9%)	With sodium bicarbonate; sodium acetate; In ethanol; acetone;	EXAMPLE 76 Preparation of 1-(4-fluorophenyl)-3-(2-methyl-3-thiazolidinyl)propan-1-one 3.73 g (0.02 mol) of beta-chloro-4-fluoropropiophenone are added in little portions at room temperature to a suspension containing 2.06 g (0.02 mol) of 2-methylthiazolidine and 1.64 g (0.02 mol) of anhydrous sodium acetate in 20 ml of ethanol over 30 minutes under stirring. After stirring for an additional 3 hours, the reaction mixture is evaporated, saturated sodium hydrogen carbonate solution is added to the oily yellow residue and it is extracted twice with 30 ml of ether each. After drying and evaporating the extract, the oily yellow residue is dissolved in acetone and acidified by 48% hydrobromic acid. Thus, 4.26 g of a white crystalline product are obtained and recrystallized twice from ethanol to give 2.00 g (29.9%) of hydrobromide of the title compound, m.p.: 151-152 C. The compounds of formula (I), wherein R1 means a carbonyl group, R2, R3, R4 and R5 are hydrogen and n as well as m are 1, which were prepared as described in Example 76, are summarized in Table VII.
	With sodium bicarbonate; sodium acetate; In ethanol; acetone;	Example 76 1-(4-fluorophenyl)-3-(2-methyl-3-thiazolidinyl)propan-1-one 3.73 g (0.02 mol) of beta-chloro-4-fluoropropiophenone are added in small amounts at room temperature to a suspension containing 2.06 g (0.02 mol) of 2-methylthiazolidine and 1.64 g (0.02 mol) of anhydrous sodium acetate in 20 ml of ethanol during 30 minutes under stirring. After stirring for an additional 3 hours, the reaction mixture is evaporated, saturated sodium hydrogen carbonate solution is added to the oily yellow residue and it is extracted twice with 30 ml of ether each time. After drying and evaporating the extract, the oily yellow residue is dissolved in acetone and acidified by 48% hydrobromic acid. Thus, 4.26 g of a white crystalline product are obtained and recrystallized twice from ethanol to give 2.00 g (29.9%) of the hydrobromide salt of the title compound, m.p.: 151-152C. The following analogous compounds of formula (I), wherein R is a carbonyl group, R2, R3, R3 and R5 are all hydrogen atoms and n and m are 1, were prepared using the process described in Example 76 above using the appropriate precursors, and they are summarized in Table VII.

Reference： [1]Patent: US5096902,1992,A
[2]Patent: EP411775,1991,A1

41
[ 347-93-3 ]
N-[3-(4-fluorophenyl)-3-oxopropyl]pipecolic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In methyl pipecolinate;	Step 1 N-[3-(4-Chlorophenyl)-3-(4-fluorophenyl)3-hydroxypropyl]pipecolic Acid Methyl Ester (Compound B30) N-[3-(4-Fluorophenyl)-3-oxopropyl]pipecolic acid methyl ester was prepared in 92% yield by alkylation of methyl pipecolinate with 3chloro-4'-fluoropropiophenone (Aldrich) as described in Example 20A (Step 1).

Reference： [1]Patent: US6191165,2001,B1

42
[ 915709-27-2 ]
[ 347-93-3 ]
C₃₁H₃₂F₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 250℃; for 0.333333h;Irradiation;	Preparation of intermediate compound 7. A mixture of intermediate compound 6 (0.00284 mol), <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)-1-propanone</strong> (0.00568 mol) and potassium carbonate (0.0057 mol) in acetonitrile (q.s.) was irradiated under microwave conditions at 250 C for 20 minutes. The solution was concentrated under reduced pressure and the residue was dissolved in DCM, washed with water and with brine, then dried. The solvent was evaporated and the residue was purified by short open column chromatography over silica gel (eluent: DCM/MeOH 98/2). The product fractions were collected and the solvent was evaporated. A part of this residue (1.2 g, 84 %) was converted into the ethanedioate salt (1 :1) by treatment with oxalic acid in diethylether. The resulting precipitate was filtered off, washed with cold diethylether and dried, yielding 0.032 g of intermediate compound 7.

Reference： [1]Patent: WO2006/122944,2006,A1 .Location in patent: Page/Page column 23

43
[ 926930-16-7 ]
[ 347-93-3 ]
[ 926930-17-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; at 20℃; for 18h;	2.2 218 mg (0.67 mmol) of caesium carbonate are added to a solution of 169 mg (0.50 mmol) of 2-benzo-1,2,5-thiadiazol-5-yl-N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)acetamide and 93.3 mg (0.5 mmol) of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> in 5 ml of acetonitrile, and the mixture is stirred at room temperature for 18 hours. The reaction mixture is filtered, and the filtrate is evaporated: 2-benzo-1,2,5-thiadiazol-5-yl-N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-N-[3-(4-fluorophenyl)-3-oxopropyl]acetamide as colourless solid; ESI 489. This material is employed for the next reaction step without further purification.

Reference： [1]Patent: US2008/249095,2008,A1 .Location in patent: Page/Page column 20-21

44
[ 347-93-3 ]
[ 1730-25-2 ]
[ 1110641-72-9 ]

Yield	Reaction Conditions	Operation in experiment
97%		A 250-mL flask was charged with anhydrous CeCI3 (5.58 g, 22.6 mmol) and THF (40 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to -78 0C and a solution of allylmagnesium bromide (1.0 M in THF, 21 <n="177"/>mL, 21.0 mmol) was added. After stirring for 2 h at -78 0C, a solution of 3-chloro-1- (4-fluorophenyl)propan-1-one (2.522 g, 13.5 mmol) in THF (30 mL) was added via cannula. The reaction mixture was allowed to slowly warm to 8 0C while stirring overnight (18 h). The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (3.0049 g, 97%) as an oil. LC-MS Method 1 tH = 1.79 min, m/z 213, 211 (M-OH)+; 1H NMR (400 MHz, CDCI3) delta 7.37-7.32 (m, 2H), 7.07-7.02 (m, 2H), 5.57-5.47 (m, 1H), 5.20-5.19 (m, 1H), 5.16 (m, 1H), 3.59-3.52 (m, 1 H), 3.24-3.18 (m, 1 H), 2.70 (dd, J = 13.8, 5.9 Hz, 1 H), 2.50 (dd, J = 13.8, 8.5 Hz, 1 H), 2.29 (t, J = 7.9 Hz, 2H), 2.22 (s, 1 H); 19F NMR (376 MHz, CDCI3) delta -116.52 (m).
97%		EXAMPLE 1; 6-allyl-6-(4-fluorophenyl)-3-(methyl(phenyl)amino)-1 ,3-oxazinan-2-oneStep 1 A 250-mL flask was charged with anhydrous CeCI3 (5.58 g, 22.6 mmol) andTHF (40 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to -78 0C and a solution of allylmagnesium bromide (1.0 M in THF, 21 mL, 21.0 mmol) was added. After stirring for 2 h at -78 0C1 a solution of 3-chloro-1- (4-fluorophenyl)propan-1-one (2.522 g, 13.5 mmol) in THF (30 mL) was added via <n="52"/>cannula. The reaction mixture was allowed to slowly warm to 8 0C while stirring overnight (18 h). The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 1- chloro-3-(4-fluorophenyl)hex-5-en-3-ol (3.0049 g, 97%) as an oil. LC-MS Method 1 tR = 1.79 min, m/z. 213, 21 1 (M-OH)+; 1H NMR (400 MHz, CDCI3) delta 7.37-7.32 (m, 2H), 7.07-7.02 (m, 2H), 5.57-5.47 (m, 1 H), 5.20-5.19 (m, 1 H), 5.16 (m, 1 H)1 3.59-3.52 (m, 1 H), 3.24-3.18 (m, 1 H), 2.70 (dd, J = 13.8, 5.9 Hz, 1 H), 2.50 (dd, J = 13.8, 8.5 Hz, 1 H), 2.29 (t, J = 7.9 Hz, 2H), 2.22 (s, 1 H); 19F NMR (376 MHz, CDCI3) delta -1 16.52 (m).
97%		Step 1. l-chloro-3-(4-fluorophenyl)hex-5-en-3-ol; A 250-mL flask was charged with anhydrous CeCl3 (5.58 g, 22.6 mmol) and THF (40 rnL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to -78 0C and a solution of allylmagnesium bromide (1.0 M in THF, 21 mL, 21.0 mmol) was added. After stirring for 2 h at -78 0C, a solution of 3- chloro-l-(4-fluorophenyl)propan-l-one (2.522 g, 13.5 mmol) in THF (30 mL) was added via cannula. The reaction mixture was allowed to slowly warm to 8 0C while stirring overnight (18 h). The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford of l-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (3.0049 g, 97%) as an oil. LC-MS Method 1 tR = 1.79 min, m/z 213, 211 (M-OH)+; 1H NMR (400 MHz, CDCl3) delta 7.37-7.32 (m, 2H), 7.07-7.02 (m, 2H), 5.57-5.47 (m, IH), 5.20-5.19 (m, IH), 5.16 (m, IH), 3.59-3.52 (m, IH), 3.24-3.18 (m, IH), 2.70 (dd, J = 13.8, 5.9 Hz, IH), 2.50 (dd, J = 13.8, 8.5 Hz, IH), 2.29 (t, J = 7.9 Hz, 2H), 2.22 (s, IH); 19F NMR (376 MHz, CDCl3) delta -116.52 (m).

97%		Step 1. l-chloro-3-(4-fluorophenyl)hex-5-en-3-olA 250-mL flask was charged with anhydrous CeCl3 (5.58 g, 22.6 mmol) and THF (40 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to -78 0C and a solution of allylmagnesium bromide (1.0 M in THF, 21 mL, 21.0 mmol) was added. After stirring for 2 h at -78 0C, a solution of 3-chloro-l-(4- fluorophenyl)propan-l-one (2.522 g, 13.5 mmol) in THF (30 mL) was added via cannula. The reaction mixture was allowed to slowly warm to 8 C while stirring overnight (18 h). The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 1 - chloro-3-(4-fluorophenyl)hex-5-en-3-ol (3.0049 g, 97%) as an oil. LC-MS Method 1 tR = 1.79 min, m/z 213, 211 (M-OH)+; 1H NMR (400 MHz, CDCl3) delta 7.37-7.32 (m, 2H), 7.07-7.02 (m, 2H), 5.57-5.47 (m, IH), 5.20-5.19 (m, IH), 5.16 (m, IH), 3.59-3.52 (m, IH), 3.24-3.18 (m, IH), 2.70 (dd, J = 13.8, 5.9 Hz, IH), 2.50 (dd, J = 13.8, 8.5 Hz, IH), 2.29 (t, J = 7.9 Hz, 2H), 2.22 (s, IH); 19F NMR (376 MHz, CDCl3) delta -116.52 (m).
97%		A 250-mL flask was charged with anhydrous CeCl3 (5.58 g, 22.6 mmol) and THF (40 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to -78 C. and a solution of allylmagnesium bromide (1.0 M in THF, 21 mL, 21.0 mmol) was added. After stirring for 2 h at -78 C., a solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (2.522 g, 13.5 mmol) in THF (30 mL) was added via cannula. The reaction mixture was allowed to slowly warm to 8 C. while stirring overnight (18 h). The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (3.0049 g, 97%) as an oil. LC-MS Method 1 tR=1.79 min, m/z 213, 211 (M-OH)+; 1H NMR (400 MHz, CDCl3) delta 7.37-7.32 (m, 2H), 7.07-7.02 (m, 2H), 5.57-5.47 (m, 1H), 5.20-5.19 (m, 1H), 5.16 (m, 1H), 3.59-3.52 (m, 1H), 3.24-3.18 (m, 1H), 2.70 (dd, J=13.8, 5.9 Hz, 1H), 2.50 (dd, J=13.8, 8.5 Hz, 1H), 2.29 (t, J=7.9 Hz, 2H), 2.22 (s, 1H); 19F NMR (376 MHz, CDCl3) delta-116.52 (m).
87%		Step 2A 1000-mL flask was charged with anhydrous CeCI3 (50 g, 0.2 mol) and THF (360 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to -78 0C, and a solution of allylmagnesium bromide (1.0 M in THF, 188.2 mL, 188 mmol) was added. After stirring for 2 h at -78 0C, a solution of 3-chloro-1-(4- fluorophenyl)propan-1-one (22.6 g, 120 mmol) in THF (269 mL) was added dropwise. The reaction mixture was allowed to slowly warm to rt while stirring overnight. The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 1-chloro-3-(4- fluorophenyl)hex-5-en- 3-ol (23.8 g, 87%) as an oil. 1H NMR (CDCI3): 2.27 (m, 1 H), 2.31 (m, 2H), 2.50 (m, 1 H), 2.69 (m, 1 H), 3.19 (m, 1 H), 3.52 (m, 1 H), 5.16 (m, 2H), 5.51 (m, 1 H), 7.04 (m, 2H), 7.35 (m, 2H).

Reference： [1]Patent: WO2009/17664,2009,A1 .Location in patent: Page/Page column 175-176
[2]Patent: WO2009/94169,2009,A1 .Location in patent: Page/Page column 50-51
[3]Patent: WO2010/10150,2010,A1 .Location in patent: Page/Page column 38
[4]Patent: WO2010/91067,2010,A2 .Location in patent: Page/Page column 65-66
[5]Patent: US2010/331320,2010,A1 .Location in patent: Page/Page column 28; 29
[6]Journal of Medicinal Chemistry,2011,vol. 54,p. 6050 - 6062
[7]Patent: WO2009/75835,2009,A1 .Location in patent: Page/Page column 46

45
[ 347-93-3 ]
[ 7393-43-3 ]
[ 1110641-72-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 1 ,1 '-bi-2-naphthol (0.2280 g, 0.80 mmol, 0.26 equiv), CH2CI2 (5 mL) and titanium(IV) isopropoxide (0.2243 g, 0.79 mmol, 0.26 equiv) were added 2-propanol (3.1620 g, 52.6 mmol, 17 equiv), tetraallylstannane (1.2538 g, 4.43 mmol, 1.43 equiv), and <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (0.5760 g, 3.09 mmol, 1.0 equiv) successively. The reaction mixture was stirred at rt under nitrogen for 22 h. The reaction was quenched with satd aq NH4CI and extracted with EtOAc. The organic layer was dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol as an oil.
		Step 1. l-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol.; To a solution of l,l '-bi-2-naphthol (0.2280 g, 0.80 mmol, 0.26 equiv), CH2Cl2 (5 mL) and titanium(IV) isopropoxide (0.2243 g, 0.79 mmol, 0.26 equiv) were added 2-propanol (3.1620 g, 52.6 mmol, 17 equiv), tetraallylstannane (1.2538 g, 4.43 mmol, 1.43 equiv), and 3-chloro-l-(4-fluorophenyl)propan-l-one (0.5760 g, 3.09 mmol, 1.0 equiv) successively. The reaction mixture was stirred at rt under nitrogen for 22 h. The reaction was quenched with satd aq NH4Cl and extracted with EtOAc. The organic layer was dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford l-chloro-3-(4-fluorophenyl)hex-5-en-3-ol as an oil.

Reference： [1]Patent: WO2009/17664,2009,A1 .Location in patent: Page/Page column 167
[2]Patent: WO2010/10150,2010,A1 .Location in patent: Page/Page column 36-37

46
[ 347-93-3 ]
[ 851011-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; for 2 - 3h;Heating / reflux;	In a flask, 3-chloro-4'-fluoropropriophenone, sodium iodide and acetone were charged. The solution was heated to reflux and aged for 2 to 3 hours. After the reaction is <n="54"/>complete, the batch is cooled to room temperature. Water (12 vol) is added slowly to quench reaction and to crystallize the product. The batch is aged two hours then filtered. The cake is washed with water (3 vol) and dried under vacuum at 450C to a final target of less than 0.2 wt % water.

Reference： [1]Organic Letters,2010,vol. 12,p. 512 - 515
[2]Patent: WO2009/54887,2009,A1 .Location in patent: Page/Page column 26-27; 52-53

47
[ 347-93-3 ]
[ 3850-30-4 ]
[ 1161353-52-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In acetonitrile; at 20℃;	Step iTo a solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (5.0 g, 0.027 mol) and K2CO3 (7.45 g, 0.054 mol) in acetonitrile (100 ml.) was added (S)-3,3-dimethylbutan-2- amine (3.24 g, 0.032 mol), and the reaction mixture was stirred at rt overnight. The <n="49"/>solution was filtered, and the filtrate was concentrated to give (S)-3-(3,3-dimethylbutan- 2-ylamino)-1-(4-fluorophenyl)propan-1-one (6.40 g, 94%). 1H NMR (CDCI3): 0.82 (s, 9H)1 0.91-0.96 (d, 3H), 2.14-2.22 (m, 1 H), 2.73-2.82 (m, 1H), 3.01-3.11 (m, 3H), 7.01- 7.09 (m, 2H), 7.88-7.96 (m, 2H).; Step iTo a solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (5.0 g, 0.027 mol) and K2CO3 (7.45 g, 0.054 mol) in acetonitrile (100 mL) was added (S)-3,3-dimethylbutan-2- amine (3.24 g, 0.032 mol), and the reaction mixture was stirred at rt overnight. The solution was filtered, and the filtrate was concentrated to give (S)-3-(3,3- dimethylbutan- <n="56"/>2-ylamino)-1-(4-fluorophenyl)propan-1-one (6.40 g, 94%), which was used for the next step without further purification. 1H NMR (CDCI3): 0.82 (s, 9H), 0.91-0.96 (d, 3H), 2.14- 2.22 (m, 1 H), 2.73-2.82 (m, 1 H), 3.01-3.11 (m, 3H), 7.01-7.09 (m, 2H), 7.88-7.96 (m, 2H).

Reference： [1]Patent: WO2009/75835,2009,A1 .Location in patent: Page/Page column 47-48; 54-55

48
[ 847728-89-6 ]
[ 347-93-3 ]
[ 1172022-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In acetonitrile;Reflux;	Step 1: To a solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (5.4 g, 29 mmol) in acetonitrile (100 mL) was added (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (8.67 g, 29 mmol), K2CO3 (12.4 g, 90 mmol) and Kl (14.9 g, 90 mmol). The mixture was refluxed overnight. The reaction mixture was filtered through a celite pad, and the filtrate was concentrated to give the crude (S)-tert-butyl 1-(4-bromophenyl)ethyl (3-(4-fluorophenyl)- 3-oxopropyl)carbamate (13 g), which was used to the next step without purification.

Reference： [1]Patent: WO2009/88997,2009,A1 .Location in patent: Page/Page column 88

49
[ 347-93-3 ]
[ 24424-99-5 ]
[ 27298-97-1 ]
[ 1172022-05-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		EXAMPLE 7 3-((1 S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1 ,3-oxazinan-2-one <n="74"/>Step 1To a stirred solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (789 mg, 4.23 mmol) and J-Pr2NEt (0.91 mL, 5.1 mmol) in THF (10 ml_) was added (S)-1 -(4- bromophenyl)ethanamine (0.68 mL, 4.65 mmol). The mixture was stirred overnight at rt and 10% aq K2CO3 (10 mL) and di-tert-butyl dicarbonate (1.38 g, 6.35 mmol) were added. The mixture was stirred overnight at rt and concentrated under reduced pressure. The aqueous residue was extracted with ether (100 mL). The ether extract was washed with 5% aq HCI (20 mL), satd aq NaHCO3 (20 mL) and brine (20 mL), and dried over Na2SO4. Removal of the solvent left an oil (3.77 g) which was purified by chromatography on a 40-g silica gel cartridge eluted with a 0-60% EtOAc in hexanes gradient to afford (S)-tert-butyl 1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)- 3-oxopropyl)carbamate (2.04 g, quant) as a waxy solid. LC-MS (3 min) tR = 2.35 min, m/2 = 474, 472, 452, 450, 352, 350.

Reference： [1]Patent: WO2009/102460,2009,A2 .Location in patent: Page/Page column 72-73

50
[ 347-93-3 ]
[ 27298-97-1 ]
[ 1151795-67-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; In acetonitrile;	To a solution of (S)-1-(4-bromophenyl)ethanamine (20 g, 0.1 mol) and K2CO3 (28 g, 0.2 mol) in MeCN (200 ml.) was added a solution of 3-chloro-1-(4- fluorophenyl)propan-1-one (18.6 g, 0.1 mol) in MeCN (20 ml_). The mixture was stirred overnight. The solid was filtered, and the filtrate was concentrated to give (S)- 3-(1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)propan-1-one (30 g, 86%), which was used for the next step without purification. 1H NMR (CDCI3): delta=1.29 (m, 3H), 2.56-2.91 (m, 2H), 3.11 (m, 2H), 3.68 (q, 1 H), 7.11 (m, 2H), 7.21 (m, 2H), 7.43 (m, 2H), 7.99 (m, 2H).

Reference： [1]Patent: WO2009/61498,2009,A1 .Location in patent: Page/Page column 78-79

51
[ 3756-30-7 ]
[ 347-93-3 ]
[ 1192838-38-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With water; ammonium chloride; zinc; In tetrahydrofuran; at 20℃;Reflux;	Method 2Step 1A solution of 3-chloro-l-(4-fluorophenyl)-propan-l-one (18.6 g, 0.1 mol) in THF (50 mL) was added to a well-stirred suspension of zinc power (13 g, 0.2 mol) in a mixture of aqueous saturated NH4Cl solution (260 mL) and THF (65 mL). A solution of 3-iodo-2-methylprop-l-ene (36.4 g, 0.2 mol) in THF (50 mL) was added dropwise. The reaction mixture was mildly exothermic, and began to reflux spontaneously. After the refluxing had ceased, the mixture was stirred for 1 h. TLC showed the 3-chloro-l- (4-fluorophenyl)propan-l-one not reacted completely. A solution of 3-iodo-2- methylprop-1-ene (18.2 g, 0.1 mol) in THF (30 mL) was added, and the mixture was stirred at rt overnight. The mixture was extracted with EtOAc (2 x 500 mL). The combined organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with petroleum ether/ EtOAc 50: l? 30: l? 5:1, to give l-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (17 g, yield 76 %) as an oil. Step 2A mixture of l-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (3.15 g, 13 mmol), (S)-(-)- l-(- bromophenyl)ethyl isocyanate (3.5 g, 16 mmol), and DBU (8 g, 33 mmol) in THF (80 mL) was heated to reflux for 25 h. The mixture was diluted with EtOAc and washed with INaq HCl. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column to give (i?)-3-((iotaS)-l-(4- bromophenyl)-ethyl)-6-(4-fluorophenyl)-6-(2-methylallyl)-l,3-oxazinan-2-one (2.13 g, yield: 38 %).
76%	With water; ammonium chloride; zinc; In tetrahydrofuran; at 20℃;Reflux;	A solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)-propan-1-one</strong> (18.6 g, 0.1 mol) in THF (50 mL) was added to a well-stirred suspension of zinc power (13 g, 0.2 mol) in a mixture of aqueous saturated NH4Cl solution (260 mL) and THF (65 mL). A solution of 3-iodo-2-methylprop-1-ene (36.4 g, 0.2 mol) in THF (50 mL) was added dropwise. The reaction mixture was mildly exothermic, and began to reflux spontaneously. After the refluxing had ceased, the mixture was stirred for 1 h. TLC showed the <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> not reacted completely. A solution of 3-iodo-2-methylprop-1-ene (18.2 g, 0.1 mol) in THF (30 mL) was added, and the mixture was stirred at rt overnight. The mixture was extracted with EtOAc (2×500 mL). The combined organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with petroleum ether/EtOAc 50:1?30:1?5:1, to give 1-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (17 g, yield 76%) as an oil.

Reference： [1]Patent: WO2010/91067,2010,A2 .Location in patent: Page/Page column 69
[2]Patent: US2010/331320,2010,A1 .Location in patent: Page/Page column 30; 31

52
[ 347-93-3 ]
[ 98-80-6 ]
[ 41938-64-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1874 - 1880

53
[ 347-93-3 ]
[ 1679-18-1 ]
3-(4-chlorophenyl)-1-(4-fluorophenyl) propan-1-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1874 - 1880

54
[ 347-93-3 ]
[ 1423-26-3 ]
1-(4-fluorophenyl)-3-(3-(trifluoromethyl)phenyl)propan-1-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1874 - 1880

55
[ 347-93-3 ]
[ 1826-67-1 ]
5-chloro-3-(4-fluorophenyl)pent-1-en-3-ol [ No CAS ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 10802 - 10804

56
[ 347-93-3 ]
[ 127-09-3 ]
[ 66267-03-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With acetic acid; potassium iodide; at 130℃; for 16h;Sealed tube;	a) Synthesis of acetic acid [3-(4-fluorophenyl)-3-oxo-propyl] ester To a solution of 3-chloro-1-(4-fluorophenyl)-propan-1 -one (4.0 g, 21.5 mmoi) in AcOH (30 ml) in a sealed tube are added sodium acetate (8.64 g, 105.4 mmoi) and potassium iodide (0.36 g, 2.15 mmoi) at RT. The reaction mixture is stirred at 130 C for 16 h. After completion of reaction, the mixture is diluted with water (60 ml) and neutralized with aqueous sodium carbonate at 0 C. The aqueous layer is extracted with DCM (3 x 100 ml). The combined organic layers are washed with water (200 ml), brine (200ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield acetic acid [3-(4-fluorophenyl)-3-oxo- propyl] ester (3.00 g, 14.3 mmoi, 66%).

Reference： [1]Patent: WO2014/82737,2014,A1 .Location in patent: Page/Page column 35-36

57
[ 347-93-3 ]
[ 64-19-7 ]
[ 66267-03-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium acetate; potassium iodide; at 130℃; for 16h;Sealed tube;	To a solution of <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)-propan-1-one</strong> (4.0 g, 21.5 mmol) in AcOH (30 ml) in a sealed tube are added sodium acetate (8.64 g, 105.4 mmol) and potassium iodide (0.36 g, 2.15 mmol) at RT. The reaction mixture is stirred at 130C for 16 h. After completion of reaction, the mixture is diluted with water (60 ml) and neutralized with aqueous sodium carbonate at 0C. The aqueous layer is extracted with DCM (3×100 ml). The combined organic layers are washed with water (200 ml), brine (200 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield acetic acid [3-(4-fluorophenyl)-3-oxo-propyl]ester (3.00 g, 14.3 mmol, 66%).

Reference： [1]Patent: US2014/148468,2014,A1 .Location in patent: Paragraph 0273

58
[ 347-93-3 ]
[ 73183-34-3 ]
C₁₅H₂₀BFO₃ [ No CAS ]

Reference： [1]ChemCatChem,2015,vol. 7,p. 660 - 665

59
[ 625-36-5 ]
[ 460-00-4 ]
[ 347-93-3 ]

Yield	Reaction Conditions	Operation in experiment
		4,7-Bis-(4-fluorophenyl)-1,10-phenanthroline(1): (1) To an oven dried 500 mL three neck flask equipped with stir bar, condenser, and argon inlet was added 20,000 g of 4-fluorobromobenzene (0.115 mol) and 200 mL of freshly distilled tetrahydrofuran. 5.555 g (0.230 mol) of freshly cleaned magnesium turnings was added while under argon flow. The solution was gently heated until the color changed to brown and visually half of the magnesium was consumed. The resulting Grignard was then canulated to a flask equipped with stir bar and argon inlet, containing 14.982 g (0.118 mol) 3-chloropropionic acid chloride at in 100 mL of freshly distilled tetrahydrofuran maintained at a temperature of 0 C on an ice bath. The Grignard was added over a period of 90 min and stirred for 90 min after addition. The solvents were then removed by rotary evaporation and the remaining solids were flash chromatographed using methylene chloride and silica. The resulting 3-chloro-1-(4-fluoro-phenyl)-propan-1-one was used without further purification.

Reference： [1]Journal of Fluorine Chemistry,2015,vol. 173,p. 63 - 68

60
[ 347-93-3 ]
[ 88-74-4 ]
4-(4-fluorophenyl)-8-nitroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.890 g	With phosphoric acid; orthoarsenic acid; at 100 - 150℃; for 1.5h;Inert atmosphere;	o-Nitroaminobenzene (5.00 g, 36.200 mmol), arsenic acid (20.00 g, 52.000 mmol) and o-phosphoric acid (60 mL) were added to a round bottom flask with stir bar and purged with nitrogen. The solution was heated to 100 C and a melt of 3-chloro-1-(4-fluoro-phenyl)-propan-1-one (12.376 g, 66.320 mmol), was added drop wise while maintaining the solution at 100 C. The solution was heated to 140-150 C for 1.5 h and then cooled to 80 C and poured onto ice. The solution was then brought to a pH of 12 using K2CO3 and the organics were extracted from the aqueous phase using methylene chloride. The contents were purified on basic alumina (methylene chloride) to yield 9.890 g (36.870 mmol) of 4-(4-fluorophenyl)-8-nitro-quinoline which was used without further purification.

Reference： [1]Journal of Fluorine Chemistry,2015,vol. 173,p. 63 - 68

61
[ 347-93-3 ]
4-(4-fluorophenyl)quinolin-8-ylamine [ No CAS ]
[ 1215007-79-6 ]

Yield	Reaction Conditions	Operation in experiment
7.343 g	With phosphoric acid; orthoarsenic acid; at 100 - 150℃; for 1.5h;Inert atmosphere;	4-(4-Fluoro-phenyl)-quinolin-8-ylamine (7.067 g, 29.661 mmol), arsenic acid (8.960 g, 23.333 mmol) and o-phosphoric acid (27 mL) were heated to 100 C under nitrogen. To this a melt of 8.333 g of p-fluoro-3-chloropropriophenone (44.655 mmol) was added drop wise. The solution was then heated to 140-150 C and the solution solidified. The solid was placed onto ice and brought to a pH of 12 followed by extraction with chloroform. The solid was recrystallized from methanol-water to yield 7.343 g of 4,7-bis(4-fluorophenyl)-1,10-phenanthroline as a colorless crystalline solid. 1H NMR (300 MHz, DOCD3, shown in the supplementary materials): delta 9.3223 (d, 2H, J=4 Hz), 8.0996 (s, 2H), 7.9528 (d, 2H, J=5 Hz), 7.7775 (m, 4H, J=5 Hz), 7.4951 (t, 4H, J=9 Hz). Mass spectrometry (ESI, shown in the supplementary materials) calculated for C24H14F2N2: 368.11; found 369.1223 for M+H. Anal. calcd for C24H14F2N2: C, 78.25; H, 3.83; F, 10.31; N, 7.60; found C, 77.78; H, 3.87; N, 7.55.

Reference： [1]Journal of Fluorine Chemistry,2015,vol. 173,p. 63 - 68

62
[ 90-15-3 ]
[ 347-93-3 ]
1-(4-fluorophenyl)-3-(4-hydroxynaphthalen-1-yl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: A solution of 2-Naphthol (865mg, 6 mmol) in THF (3 ml) was added dropwise to the solution of sodium hydroxide (0.3g, 7.5mmol) in H2O(1.5 ml) at room tempera-ture. The mixture was stirred for 15 min. Thensolution of 3-chloro-1-phenylacetone (843.1 mg, 5 mmol) in THF (3 ml) was added slowly. Afteraddition, the mixture was stirred for another 2 h. TLC indicated the3-chloro-1-phenyl acetone was consumed up. Thenethyl acetate and water were added, after separation, the organic phasewas washed with brine, dried over Na2SO4 ,thenconcentrated. The residue was purified via flash column chromatography on silica gel

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5039 - 5042

63
[ 591-50-4 ]
[ 347-93-3 ]
[ 22966-25-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 - 90℃; under 750.075 Torr; for 16h;Inert atmosphere;	General procedure: A mixture of Pd(OAc)2 (4.5 mg, 0.02 mmol), PPh3 (11.2 mg, 0.04 mmol), iodobenzene (1a) (82 mg, 0.4mmol), 3-chloropropiophenone (2a) (87 mg, 0.5 mmol), and K2CO3 (166 mg, 1.2 mmol) in DMF (2.5 mL) was stirred under a N2 atmosphere at room temperature for 10 min, and then heated at 90 C for 16 h. The reaction was then cooled to ambient temperature and diluted with CH2Cl2 (10 mL) before being filtered through a short pad of silica gel. The silica pad was rinsed with DCM (5 mL), and the combined filtrates were washed with brine (15 mL), dried over anhydrous Na2SO4. The solvent was then removed under reduced pressure to give the crude product as a residue, which was purified by silica gel column chromatography eluting with a mixture of petroleum ether (60-90 C)/EtOAc (v/v = 30:1).

Reference： [1]Chinese Journal of Catalysis,2015,vol. 36,p. 78 - 85

64
[ 347-93-3 ]
[ 105-56-6 ]
ethyl 2-cyano-5-(4-fluorophenyl)-5-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		To a stirring solution of ethyl 2-cyanoacetate (18.23 g, 161.2 mmol, 6.0 equiv) in THF (100 mL) at 0 C. was added K2CO3 (7.4 g, 54. mmol, 2.0 equiv). After stirring for 10 min at 0 C., <strong>[347-93-3]3-chloro-1-(4-fluorophenyl)propan-1-one</strong> (5.0 g, 27. mmol, 1.0 equiv) was added portionwise. The resulting mixture was warmed to room temperature, stirred for 3 h and concentrated in vacuo. The residue was diluted with EtOAc (200 mL) and washed with H2O (2×100 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by preparative HPLC (IntelFlash): Column, C18; mobile phase, H2O/CH3CN=100/0 (v/v) increasing to H2O/CH3CN=0/100 (v/v) over 45 min). The fractions containing pure compound were combined and concentrated in vacuo to yield 4.0 g (57%) of the title compound as yellow oil. LC-MS (ES, m/z): [M+H]=264. 1H-NMR (300 MHz, DMSO-d6): delta 8.05 (m, 2H), 7.37 (m, 2H), 4.22 (m, 3H), 3.23 (m, 2H), 2.20 (m, 2H), 1.24 (m, 3H) ppm.

Reference： [1]Patent: US2016/176868,2016,A1 .Location in patent: Paragraph 0165; 0166

65
[ 347-93-3 ]
[ 62-53-3 ]
[ 37155-05-8 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 904 - 907

66
[ 272769-47-8 ]
[ 347-93-3 ]
2-(1-(3-(4-fluorophenyl)-3-oxopropyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
180 mg	With potassium carbonate; In N,N-dimethyl-formamide; for 3h;	111 mg 6 (0.45 mmol, 1.0 eq.), 102 mg 7i (0.55 mmol, 1.2 eq.), 126 mg K2CO3 (0.91 mmol, 2.0 eq.) were added into 10 mL DMF and stirred for 3 hours. The reactant was poured into about 100 mL ice water and stirred continuously. White solid was precipitated, separated by filtration and dried to get 180 mg 8i with yield of 100.4%.1H NMR (400 MHz, DMSO) delta 12.69 (s, 1H), 9.35 (d, J = 3.2 Hz, 1H), 8.14 - 8.04 (m, 2H), 7.80 (dd, J = 7.6, 0.8 Hz, 1H), 7.76 - 7.59 (m, 2H), 7.31 (dt, J = 15.5, 8.3 Hz, 3H), 3.23 (dd, J = 8.5, 5.7 Hz, 2H), 3.12 - 2.83 (m, 3H), 2.73 (t, J = 7.0 Hz, 2H), 2.27 - 1.91 (m, 4H), 1.84 (qd, J = 12.4, 3.2 Hz, 2H).13C NMR (101 MHz, DMSO) delta 198.00, 166.33, 166.25, 159.04, 140.75, 134.50, 133.56, 131.04, 130.95, 122.10, 121.95, 121.42, 115.80, 115.59, 114.58, 53.14, 52.83, 35.98, 35.75, 30.37.HRMS m/z 395.1878 (calcd for C22H24FN4O2 (M+H)+, 395.1878).

Reference： [1]Chinese Chemical Letters,2019

67
[ 887144-94-7 ]
[ 347-93-3 ]
2-chloro-4,4,4-trifluoro-1-(4-fluorophenyl)butan-1-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2019,vol. 37,p. 1025 - 1030

68
[ 347-93-3 ]
4-bromo-2-chloro-5-fluoropyridine [ No CAS ]
C₁₄H₁₁ClFNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: Under N2 protection, at -70 C, n-BuLi (2.5 M, 1.29 mL, 1.20 eq) was added dropwise into 4-bromo-2-chloropyridine (515.62 mg, 2.68 mmol, 1.00 eq) in toluene (3.00 mL) solution, after completion of adding, the mixturewas stirred at the temperature for 20mins, then the compound 12-1(500.00 mg, 2.68 mmol, 1.00 eq) was addedinto the suspension above. The temperature of the reaction system was raised slowly to 25 C and stirred for 6hours. Toluene was eliminated by concentration under reduced pressure, the remaining solid was dissoloved inDMF (3.00 mL), at 25 C, NaH (160.76 mg, 4.02 mmol, purity60%, 1.50 eq) was added, then the system was heatedto 60 C and stirred for 2 hours. Then the reaction mixture was poured into H2O (80 mL), then EtOAc (30 mL x3)was used for extraction, the combined extracts was washed by brine (50 mL), then dried over anhydrous Na2SO4,followed by filtration and concentration under reduced pressure. The solid obtained was passed through silica gelcolumn chromatography (PE/EtOAc = 10/1) to give the compound 12-2. MS ESI calculated value C14H11ClFNO [M+ H]+ 264, measured value 264.

Reference： [1]Patent: EP3569592,2019,A1 .Location in patent: Paragraph 0104

69
[ 347-93-3 ]
4-bromo-2-chloro-3-fluoropyridine [ No CAS ]
C₁₄H₁₀ClF₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1:Under N2 protection, at -70 C, n-BuLi (2.5 M, 1.03 mL, 1.20 eq) was added dropwise into 4-bromo-2-chloro-3-fluoropyridine (450.32 mg, 2.14 mmol, 1.00 eq) in toluene (8.00 mL) solution, after completion of adding, themixture was stirred at the temperature for 20mins, then compound 13-1(400.00 mg, 2.14 mmol, 1.00 eq) was addedinto the suspension above. The temperature of the system was raised slowly to 25 C and stirred for 6 hours. Toluenewas eliminated by concentraion under reduced temperature, the remaining solid was dissolved in DMF(8.00 mL),at 25 C, NaH (128.40 mg, 3.21 mmol, purity60%, 1.50 eq) was added and then the system was heated to 60 Cand stirred for 2 hours.The reaction mixture was poured into water(80 mL), then extratec by EtOAc (30 mL x3), thecombined extracts was washed by brine(50 mL), then dried over anhydrous Na2SO4, followed by filtration andconcentration under reduced pressure. The solid obtained was passed through column chromatography (PE/EtOAc= 10/1) to give the compound 13-2. MS ESI calculated value C14H10ClF2NO [M + H]+ 282, measured value 282.

Reference： [1]Patent: EP3569592,2019,A1 .Location in patent: Paragraph 0105

70
[ 347-93-3 ]
[ 3575-80-2 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 15315 - 15322

71
[ 347-93-3 ]
[ 1649-18-9 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 15315 - 15322

72
[ 347-93-3 ]
6-O-methyl-9-hydrazono erythromycin A [ No CAS ]
C₃₉H₆₃ClFN₃O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		9- hydrazone clarithromycin 0.5g (0.66mmol) was dissolved in 5mL of methanol,Add 0.18 g (0.98 mmol) of 4-fluorophenyl-3-chloropropanone and 0.06 g (0.98 mmol) of glacial acetic acid, and heat to reflux for 3 h. Cool to room temperature, add 1.5 mL of a 1N methanolic hydrochloric acid solution, and stir at room temperature for 4 h. Add 5 mL of water and 5 mL of dichloromethane, adjust the pH to 9-10 with 3N NaOH aqueous solution, and separate the liquid.The aqueous layer was extracted with dichloromethane (5 mL), and the dichloromethane layers were combined, washed with water (5 mL 2), washed with saturated brine, and distilled under reduced pressure to constant weight. 0.23 g of yellow solid was separated by FLASH column chromatography after mixing samples with 200-300 mesh silica gel. The yield was 46%. TLC: [ethyl acetate-petroleum ether-diethylamine (5: 30: 1)] Rf = 0.26. HPLC purity 90.1%.

Reference： [1]Patent: CN110615822,2019,A .Location in patent: Paragraph 0236-0239

73
[ 347-93-3 ]
C₃₀H₅₅N₃O₉ [ No CAS ]
C₃₉H₆₁ClFN₃O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol; for 3h;Reflux;	3-O- descladinosyl-3-oxo-9-hydrazone clarithromycin 0.5g (0.83mmol) was dissolved in 5mL of methanol,Add 0.2 g (1.25 mmol) of 4-fluorophenyl-3-chloropropanone and 0.08 g (1.25 mmol) of glacial acetic acid, and heat to reflux for 3 h.Add 5 mL of water and 5 mL of dichloromethane, adjust the pH to 9-10 with 3N NaOH aqueous solution, and separate the liquid.The aqueous layer was extracted with dichloromethane (10 mL), and the dichloromethane layers were combined, washed with water (5 mL 2), washed with saturated brine, and distilled under reduced pressure to constant weight. After stirring the sample with 200-300 mesh silica gel, FLASH column chromatography separated 0.3 g of white solid with a yield of 43%. TLC: [ethyl acetate-petroleum ether-diethylamine (5: 30: 1)] Rf = 0.24, HPLC purity 90.2%.

Reference： [1]Patent: CN110615822,2019,A .Location in patent: Paragraph 0184-0187

74
[ 347-93-3 ]
[ 51-05-8 ]
[ 2918773-16-5 ]
[ 2918773-17-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 35 % 2: 25 %	Stage #1: procaine hydrochloride With sodium hydroxide Stage #2: 3-chloro-4'-fluoropropiophenone With triethylamine In tetrahydrofuran Reflux;	General Procedure A (GP-A) for the synthesis of derivatives 2c-f and 3c General procedure: Procainehydrochloride (0.02 mol, 5.45 g) (for the synthesis of compounds 2c-f) or procainamidehydrochloride (0.02 mol, 5.43 g) (for the synthesis of compound 3c) was solubilized inNaOH 1 N (200 mL) and extracted with ethyl acetate (3 100 mL). The organic layerwas dried over Na2SO4 and concentrated under reduced pressure to give a pale yellowoil that was subsequently dissolved in anhydrous THF (90 mL). Triethyl amine (15.7 mL,0.024 mol) and the proper arylpropan-1-one (0.017 mol) were then added, and the reactionwas stirred at reflux for 15 h [21]. The mixture was cooled to ambient temperature and thesolvent was reduced under vacuum. Water (300 mL) was added, and the crude product was extracted with ethyl acetate (3 200 mL). The organic layers were combined, washedwith brine, dried over Na2SO4, filtered, and concentrated to dryness. The raw materialwas purified by column chromatography on silica gel (chloroform/methanol 5:1 as eluent)or directly recrystallized (isopropanol) to give pure compound 3c as a pale yellow solid.For each derivative, the amount of the proper arylpropan-1-one, yield (%), melting point,recrystallization solvent, IR, 1H NMR, and elemental analysis are reported.

Reference： [1]Madia, Valentina Noemi; Ialongo, Davide; Patacchini, Elisa; Exertier, Cécile; Antonelli, Lorenzo; Colotti, Gianni; Messore, Antonella; Tudino, Valeria; Saccoliti, Francesco; Scipione, Luigi; Ilari, Andrea; Costi, Roberta; Di Santo, Roberto [Molecules, 2023, vol. 28, # 1]

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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 347-93-3 ] {[proInfo.proName]}

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[ 347-93-3 ] Synthesis Path-Upstream 1~4

[ 347-93-3 ] Synthesis Path-Downstream 1~74

Related Functional Groups of [ 347-93-3 ]

Fluorinated Building Blocks

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Chlorides

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[ 347-93-3 ]