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[ CAS No. 456-14-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Chemical Structure| 456-14-4

Chemical Structure| 456-14-4

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Quality Control of [ 456-14-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 456-14-4 ]

Product Details of [ 456-14-4 ]

CAS No. :	456-14-4	MDL No. :	MFCD04114421
Formula :	C₇H₈ClFN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JQDATBKJKUWNGA-UHFFFAOYSA-N
M.W :	174.60	Pubchem ID :	12456160
Synonyms :

Calculated chemistry of [ 456-14-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	44.63
TPSA :	49.87 Å²

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) :	-6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.09
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	2.36
Log Po/w (SILICOS-IT) :	1.53
Consensus Log Po/w :	1.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.95
Solubility :	1.97 mg/ml ; 0.0113 mol/l
Class :	Very soluble
Log S (Ali) :	-1.73
Solubility :	3.25 mg/ml ; 0.0186 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.38
Solubility :	0.726 mg/ml ; 0.00416 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 456-14-4 ]

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 [ 456-14-4 ]

* 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 [ 456-14-4 ]
Downstream synthetic route of [ 456-14-4 ]

[ 456-14-4 ] Synthesis Path-Upstream 1~4

1
[ 4278-01-7 ]
[ 456-14-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With ammonia In methanol; ethanol at 20℃; for 24 h; Sealed tube	General procedure: The ethyl imidate hydrochloride 4 (10 mmol) was dissolved inethanol (10 mL) and placed in a round-bottomed flask equippedwith a magnetic stir bar. After sealing the flask with a rubberseptum ammonia in methanol (10 mL) was added to the reactionmixture using a syringe. The reaction mixture was stirred at roomtemperature for 24 h. After evaporation in vacuo, the crude productwas purified by flash column chromatography over silica gel(EtOAc/methanol4:1) to afford the amidine hydrochloride 1.4.3.6 4-Fluorobenzenecarboximidamide hydrochloride (1j)<ce-sup primary_key="ce-sup-35858230-none">29c,31 Compound 4j (2.04 g, 10 mmol) was reacted under the conditions of general procedure II to deliver 4-fluorobenzenecarboximidamide hydrochloride (1j) as a white solid in 87percent yield (1.52 g, 8.7 mmol).

Reference： [1] Tetrahedron, 2014, vol. 70, # 8, p. 1635 - 1645

2
[ 1194-02-1 ]
[ 456-14-4 ]

Yield	Reaction Conditions	Operation in experiment
35.5%	With ammonia In diethyl ether; ethanol	EXAMPLE 40 4-Fluorobenzamidine Hydrochloride 4-Fluorobenzonitrile (10 g, 83 mmol) is dissolved in a mixture of anhydrous ethanol (5 mL) and diethyl ether (70 mL). The reaction mixture is cooled to ice-bath temperature and saturated with gaseous hydrogen chloride for 90 minutes. The mixture is allowed to warm to ambient temperature and stirred overnight. The colorless precipitates are filtered off, washed with diethyl ether and dissolved in anhydrous ethanol (20 mL). Diethyl ether (100 mL) saturated with gaseous ammonia is added and the solution is stirred for 3 hours. The resulting suspension is filtered and the solvent of the filtrate is removed in vacuo. The residue is washed with diisopropyl ether. After drying colourless crystals (5.15 g, 35.5percent) of melting point 210° C. are obtained.

Reference： [1] Magnetic Resonance in Chemistry, 1987, vol. 25, p. 923 - 927
[2] Patent: US5849758, 1998, A,
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1230 - 1241
[4] Patent: US2003/139415, 2003, A1,
[5] Tetrahedron, 2014, vol. 70, # 8, p. 1635 - 1645

3
[ 22179-78-8 ]
[ 456-14-4 ]

Reference： [1] Synthetic Communications, 2011, vol. 41, # 15, p. 2195 - 2199

4
[ 56108-05-5 ]
[ 456-14-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1230 - 1241

[ 456-14-4 ] Synthesis Path-Downstream 1~88

1
[ 1194-02-1 ]
[ 456-14-4 ]

Yield	Reaction Conditions	Operation in experiment
35.5%	With ammonia; In diethyl ether; ethanol;	EXAMPLE 40 4-Fluorobenzamidine Hydrochloride 4-Fluorobenzonitrile (10 g, 83 mmol) is dissolved in a mixture of anhydrous ethanol (5 mL) and diethyl ether (70 mL). The reaction mixture is cooled to ice-bath temperature and saturated with gaseous hydrogen chloride for 90 minutes. The mixture is allowed to warm to ambient temperature and stirred overnight. The colorless precipitates are filtered off, washed with diethyl ether and dissolved in anhydrous ethanol (20 mL). Diethyl ether (100 mL) saturated with gaseous ammonia is added and the solution is stirred for 3 hours. The resulting suspension is filtered and the solvent of the filtrate is removed in vacuo. The residue is washed with diisopropyl ether. After drying colourless crystals (5.15 g, 35.5percent) of melting point 210° C. are obtained.
2.9 g (100%)		EXAMPLE 4A 4-Fluorobenzenecarboximidamide Hydrochloride In analogy to the procedure for Example 3A, 2,0 g (16,5 mmol) 4-fluorobenzonitrile and proportionate amounts of the other reagents are used. Yield: 2.9 g (100percent) 1H-NMR (DMSO-d6, 200 MHz): delta=7,5 (m, 2H), 8,0 (m, 2H) ppm.

Reference： [1]Magnetic Resonance in Chemistry,1987,vol. 25,p. 923 - 927
[2]Patent: US5849758,1998,A
[3]Journal of Medicinal Chemistry,1990,vol. 33,p. 1230 - 1241
[4]Patent: US2003/139415,2003,A1
[5]Tetrahedron,2014,vol. 70,p. 1635 - 1645

2
[ 56108-05-5 ]
[ 456-14-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1230 - 1241

3
[ 456-14-4 ]
[ 146379-79-5 ]
[ 1026696-94-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2423 - 2431

4
[ 456-14-4 ]
[ 459-57-4 ]
[ 7152-15-0 ]
[ 123837-56-9 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

5
[ 456-14-4 ]
[ 7119-27-9 ]
[ 76128-67-1 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 1263 - 1267
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 1781 - 1785

6
[ 456-14-4 ]
[ 3306-07-8 ]
[ 76128-69-3 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 1263 - 1267
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 1781 - 1785

7
[ 50897-91-1 ]
[ 456-14-4 ]
6-(p-anisyl)-2-(p-fluorophenyl)-4-oxo-3,4-dihydropyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Heterocyclic Communications,2005,vol. 11,p. 479 - 484

8
[ 456-14-4 ]
[ 947739-65-3 ]
2,6-bis-(p-fluorophenyl)-4-oxo-3,4-dihydropyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Heterocyclic Communications,2005,vol. 11,p. 479 - 484

9
[ 4360-68-3 ]
[ 5815-08-7 ]
[ 456-14-4 ]
[ 76128-69-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1638 - 1640

10
[ 456-14-4 ]
[2-(4-Fluoro-phenyl)-quinazolin-8-yl]-acetic acid methyl ester [ No CAS ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 475 - 483

11
[ 456-14-4 ]
[ 203914-84-5 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 475 - 483

12
[ 456-14-4 ]
Bromo-[8-bromo-2-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-quinazolin-8-yl]-acetic acid methyl ester [ No CAS ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 475 - 483

13
[ 456-14-4 ]
[2-(4-Fluoro-phenyl)-4-methyl-6-(3-nitro-phenyl)-pyrimidin-5-yl]-(4-methyl-piperazin-1-yl)-methanone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2423 - 2431

14
[ 456-14-4 ]
[ 122253-41-2 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

15
[ 456-14-4 ]
[ 122253-18-3 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

16
[ 456-14-4 ]
[ 122252-95-3 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

17
[ 456-14-4 ]
[ 122254-31-3 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

18
[ 456-14-4 ]
[ 122254-02-8 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

19
[ 456-14-4 ]
[ 122253-62-7 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

20
[ 456-14-4 ]
[ 122253-83-2 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

21
[ 456-14-4 ]
[ 123930-31-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 52 - 60

22
[ 456-14-4 ]
[ 477879-42-8 ]

Yield	Reaction Conditions	Operation in experiment
1.47 g (44%)		EXAMPLE 11A N-{1-[3-(4-Fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl} acetamide In analogy to the procedure for Example 10A, 2,0 g (11,4 mmol) <strong>[456-14-4]4-fluorobenzenecarboximidamide hydrochloride</strong> and proportionate amounts of the other reagents are used. Yield: 1.47 g (44percent) 1H-NMR (DMSO-d6, 300 MHz): delta=0,9 (t, 3H), 1,6 (m, 1H), 1,8 (m, 1H), 1,9 (s, 3H), 4,9 (m, 1H), 7,5 (m, 2H), 8,1 (m, 3H), 14,1 (br. s, 1H) ppm.

Reference： [1]Patent: US2003/139415,2003,A1

23
[ 51673-64-4 ]
[ 456-14-4 ]
2-(4-'-Fluorophenyl)-5-methyl-4-pyrimidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.3%	In sodium hydroxide; ethanol;	Example 38 2-(4-'-Fluorophenyl)-5-methyl-4-pyrimidinone Sodium hydride (0.52 g, 13 mmol) is added to 20 ml of anhydrous ethanol and stirred for 30 minutes at ambient temperature. To this, <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> (1.47 g, 8.5 mmol) (from example 1) is added and the mixture is stirred for further 30 minutes. Methyl 2-formylpropionate (1 g, 10.6 mmol) is added dropwise and the reaction mixture is left for 4 days under stirring at ambient temperature. After cooling, the solvent is removed in vacuo and the residue is dissolved in aqueous sodium hydroxide (10 ml, 1M). Then the mixture is brought to pH 5 with 2 molar hydrochloric acid. The precipitate is filtered off and washed with diisopropyl ether. After drying, colorless crystals (0.44 g, 10.3percent) of melting point >250° C. are obtained.

Reference： [1]Patent: US5824624,1998,A

24
[ 51673-64-4 ]
[ 456-14-4 ]
[ 180606-36-4 ]

Yield	Reaction Conditions	Operation in experiment
10.3%	In sodium hydroxide; ethanol;	EXAMPLE 51 2-(4'Fluorophenyl)-5-methyl-4-pyrimidinone Sodium hydride (0.52 g, 13 mmol) is added to 20 mL of anhydrous ethanol and stirred for 30 minutes at ambient temperature. To this, <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> (1.47 g, 8.5 mmol) (from example 40) is added and the mixture is stirred for further 30 minutes. Methyl 2-formylpropionate (1 g, 10.6 mmol) is added dropwise and the reaction mixture is left for 4 days under stirring at ambient temperature. After cooling, the solvent is removed in vacuo and the residue is dissolved in aqueous sodium hydroxide (10 mL, 1M). Then the mixture is brought to pH 5 with 2 molar hydrochloric acid. The precipitate is filtered off and washed with diisopropyl ether. After drying, colorless crystals (0.44 g, 10.3percent) of melting point >250° C. are obtained.

Reference： [1]Patent: US5849758,1998,A

25
[ 456-14-4 ]
[ 87234-37-5 ]
5-propyl-2-(4-fluorophenyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium methylate; In methanol; ethanol; toluene;	EXAMPLE 1 Preparation of 5-propyl-2-(4-fluorophenyl)pyrimidine To a sodium methylate solution under agitation obtained by dissolving Na (2.8 g, 0.12 mol) in anhydrous methanol (20 c.c.) was added <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> (10.5 g, 0.06 mol), followed by adding alpha-propyl-beta-dimethylaminoacrolein (9.2 g, 0.06 mol), thereafter refluxing on heating for 3 hours with stirring, distilling off methanol under the atmospheric pressure after completion of the reaction, adding toluene (20cc) to the reaction residue to extract the resulting product, washing the extraction liquid with water, drying with anhydrous sodium sulfate, distilling off toluene and recrystallizing the remaining oily substance from ethanol (20 c.c.) to obtain the objective 5-propyl-2-(4-fluorophenyl)pyrimidine (7.0 g). Yield: 55%. M.P. 52.7 C.

Reference： [1]Patent: US4581155,1986,A

26
[ 75-70-7 ]
[ 456-14-4 ]
[ 138426-27-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide; In dichloromethane; water; at 0 - 20℃; for 2h;	General procedure: To a stirred solution of 2-fluorobenzenecarboximidamide (1.38 g, 10.0 mmol) and perchloromethyl mercaptan (1.07 mL, 10.0 mmol) in CH2Cl2 (10 mL) was added a solution of NaOH (1.60 g, 40.0 mmol) in H2O (4.0 mL) dropwise at 0 C. The mixture was stirred at 0 C for 1.0 h and at room temperature for 1.0 h. The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane?EtOAc) to give 9
	With sodium hydroxide; In dichloromethane; water; at 0℃; for 0.5h;	Intermediate 13; 5-Chloro-3-(4-fluoro-phenyl)-[1,2,4]thiadiazole; To a suspension of <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> (0.385 g) in DCM (5 mL) was added perchloromethyl mercaptan (0.219 mL). The resulting mixture was cooled to 0° C., treated with 6 N NaOH (2 mL) and stirred for 30 min. The resulting mixture was diluted with water (10 mL) and extracted with DCM (20 mL). The organic layer was dried (MgSO4) and concentrated. Chromatography of the residue (0-20percent EtOAc-hexanes) gave the title compound as a yellow-orange solid (0.43 g).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 28 - 41
[2]Patent: US2007/4741,2007,A1 .Location in patent: Page/Page column 14

27
[ 456-14-4 ]
2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bistetrafluoroborate [ No CAS ]
[ 944904-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; potassium tert-butylate; for 8h;Heating / reflux;	Example 132 3-[2-(4-Fluoro-phenyl)-pyrimidin-5-yl]-N-(thiazol-2-yl)-acrylamide [Show Image] (a) 2-(4-Fluoro-phenyl)-pyrimidine-5-carbaldehyde; 2 g (11.45 mmol) of <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong>, 4.09 g (11.45 mmol) of 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane-bis(tetrafluoroborate) and 3.86 g (34.36 mmol) of potassium tert-butylate in 70 ml of ethanol were heated under reflux for 8 h. After concentration, water and ethyl acetate were added. The organic phase was washed with a potassium hydrogensulfate solution and water, dried and evaporated. Yield: 1.87 g.

Reference： [1]Patent: EP1939180,2008,A1 .Location in patent: Page/Page column 62

28
[ 110-85-0 ]
[ 456-14-4 ]
[ 594-42-3 ]
[ 1062512-45-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4838 - 4843

29
[ 26260-02-6 ]
[ 456-14-4 ]
[ 1208259-07-7 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 758 - 760
[2]Chemistry of Heterocyclic Compounds,2011,vol. 46,p. 1481 - 1485

30
[ 134653-70-6 ]
[ 456-14-4 ]
ethyl 2-(4-fluorophenyl)-4-methyl-pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Example 42; 2-f4-Difluorophenyl)-4-methylpyrimidine-5-carboxylic acid-3-methylsulfamoyl-benzylamide; Step 1; <strong>[456-14-4]4-Fluorobenzamidine hydrochlorid</strong>e (1.25 g, 7.16 mmol) is added to a solution of sodium metal (0.17 g, 7.39 mmol) in dry ethanol (25 mL) and stirred at room temperature for 20 min. Ethyl-2- acetyl-3-(dimethylamino)acrylate (1.35 g, 7.16 mmol) is added. The mixture is heated to reflux for 3 hours. The solvent is removed in vacuo. The residue is dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford ethyl-2-(4-fluorophenyl)-4-methyl- pyrirnidine-5-carboxylate (1.65 g, 87percent) as a solid. MS: 261 (M+H)

Reference： [1]Patent: WO2007/41634,2007,A1 .Location in patent: Page/Page column 49

31
[ 22179-78-8 ]
[ 456-14-4 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 2195 - 2199

32
[ 456-14-4 ]
[ 289-96-3 ]
[ 68049-17-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 2492 - 2494

33
[ 899694-59-8 ]
[ 456-14-4 ]
[ 1430808-99-3 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 6798 - 6803

34
[ 456-14-4 ]
2-(2-halophenyl)-1H-indole [ No CAS ]
[ 1430808-93-7 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 6798 - 6803

35
[ 456-14-4 ]
N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(4-fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 28 - 41

36
[ 1416985-31-3 ]
[ 456-14-4 ]
[ 1411990-92-5 ]

Reference： [1]Russian Journal of General Chemistry,2013,vol. 83,p. 1402 - 1405
Zh. Obshch. Khim.,2013,vol. 83,p. 1151 - 1155,5

37
[ 1416985-32-4 ]
[ 456-14-4 ]
[ 1432172-87-6 ]

Reference： [1]Russian Journal of General Chemistry,2013,vol. 83,p. 1402 - 1405
Zh. Obshch. Khim.,2013,vol. 83,p. 1151 - 1155,5

38
[ 456-14-4 ]
[ 122775-34-2 ]
[ 1449754-21-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4508 - 4511

39
[ 923745-45-3 ]
[ 456-14-4 ]
C₂₁H₁₇FN₄O [ No CAS ]

Reference： [1]RSC Advances,2013,vol. 3,p. 24001 - 24004

40
[ 4278-01-7 ]
[ 456-14-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With ammonia; In methanol; ethanol; at 20℃; for 24h;Sealed tube;	General procedure: The ethyl imidate hydrochloride 4 (10 mmol) was dissolved inethanol (10 mL) and placed in a round-bottomed flask equippedwith a magnetic stir bar. After sealing the flask with a rubberseptum ammonia in methanol (10 mL) was added to the reactionmixture using a syringe. The reaction mixture was stirred at roomtemperature for 24 h. After evaporation in vacuo, the crude productwas purified by flash column chromatography over silica gel(EtOAc/methanol4:1) to afford the amidine hydrochloride 1.4.3.6 4-Fluorobenzenecarboximidamide hydrochloride (1j)<ce-sup primary_key="ce-sup-35858230-none">29c,31 Compound 4j (2.04 g, 10 mmol) was reacted under the conditions of general procedure II to deliver 4-fluorobenzenecarboximidamide hydrochloride (1j) as a white solid in 87percent yield (1.52 g, 8.7 mmol).

Reference： [1]Tetrahedron,2014,vol. 70,p. 1635 - 1645

41
[ 456-14-4 ]
[ 1038410-94-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iodine; caesium carbonate; In 1,2-dichloro-benzene; at 130℃; for 16h;	General procedure: To a stirred solution of amidine hydrochloride 1 (1.0 mmol) in o-dichlorobenzene (3.0 mL) was added Cs2CO3 (651 mg, 2.0 mmol) followed by iodine (508 mg, 2.0 mmol) at room temperature. The reaction mixture was stirred at 130 °C for 16 h. After cooling to room temperature the reaction mixture was diluted with 10percent aqueous Na2S2O3 (4.0 mL) and the product was extracted with EtOAc (2 × 15 mL). The combined organic layers were dried over anhydrous Na2SO4, filteredand evaporated in vacuum. The crude product was purified by flash column chromatography over silica gel using EtOAc/n-Hexane as the eluent to afford the desired product
55%	With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate); sodium hydrogencarbonate; potassium hexacyanoferrate(III); In 1,2-dichloro-benzene; at 130℃; for 24h;Sealed tube;	General procedure: A dry 10 mL vial was equipped with a magnetic stir bar andcharged with amidine hydrochloride 1 (1.0 mmol), Cu(OTf)2 (18 mg,0.05 mmol), NaHCO3 (252 mg, 3.0 mmol), 1,10-phenanthroline(36 mg, 0.20 mmol), K3[Fe(CN)6] (99 mg, 0.30 mmol) and sealedunder air. Then, freshly distilled o-dichlorobenzene (3 mL) wasadded using a syringe and the reaction mixture was stirred at130 C for 24 h. After cooling to room temperature the reactionmixture was diluted with water (5 mL) and extracted with EtOAc(320 mL). The combined organic layers were dried over anhydrousMgSO4, filtered and evaporated in vacuo. The crude productwas subjected to flash column chromatography over silica gel toyield the product 2. 4.4.10 3,5-Bis(4-flouorophenyl)-1H-1,2,4-triazole (2j) Compound 1j (175 mg, 1.0 mmol) was reacted under the conditions of general procedure III. Column chromatography over silica gel (petroleum ether/EtOAc=3:1) afforded 3,5-bis(4-flouorophenyl)-1H-1,2,4-triazole (2j) as a white solid in 55percent yield (71 mg, 0.28 mmol): mp 257-259 °C; Rf 0.50 (petroleum ether/EtOAc=1:1); IR (ATR) 1606, 1500, 1421, 1220, 1158, 1000, 842, 814, 757 cm-1; UV (CH3CN) lambdamax (log epsilon) 235 (4.31), 253 nm (4.30); 1H NMR (300 MHz, DMSO-d6) delta 7.36 (t, 3J (2'-H, 3'-H) and 3J (5'-H, 6'-H)=8.7 Hz, 4H, 3'-H and 5'-H), 8.09-8.13 (m, 4H, 2'-H and 6'-H), 14.55 (br s, 1H, NH); 13C NMR (75 MHz, DMSO-d6) delta 115.9 (d, 2J (C-F)=21.8 Hz, C-3' and C-5'), 125.8 (C-1'), 128.3 (d, 3J (C-F)=8.5 Hz, C-2' and C-6'), 157.8 (C-3 and C-5), 162.9 (d, 1J (C-F)=245.5 Hz, C-4'); MS (EI, 70 eV) m/z (percent) 257 (63) [M]+, 136 (29), 109 (8); HRMS (EI, M+) calcd for C14H9N3F2 257.0765, found 257.0748.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2227 - 2230
[2]Tetrahedron,2014,vol. 70,p. 1635 - 1645

42
[ 456-14-4 ]
[ 1038410-94-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,10-Phenanthroline; copper diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 24h;Inert atmosphere; Schlenk technique;	General procedure: To a round-bottom flask (25 mL) equipped with a spherical condenser (40 cm length) were added amidine hydrochloride 1 (1.0 mmol), Cu(OAc)2 (0.2 equiv), K2CO3 (2.0 equiv), 1,10-phenanthroline (0.1 equiv) and anhyd DMF (2.0 mL). Then the mixture was well stirred at 130°C under an inert atmosphere. After cooling off, the mixture was filtered through a pad of celite eluting with CH2Cl2 (3×6 mL). The volatiles were removed under reduced pressure and the residue was purified by a short flash silica gel column chromatography to give compound 2.

Reference： [1]Synlett,2013,vol. 24,p. 2735 - 2739

43
[ 456-14-4 ]
[ 68-12-2 ]
[ 1613637-81-2 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3540 - 3543

44
[ 1616763-12-2 ]
[ 456-14-4 ]
[ 1616763-45-1 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6579 - 6589

45
[ 1446357-42-1 ]
[ 456-14-4 ]
[ 1616763-23-5 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6579 - 6589

46
[ 1446357-39-6 ]
[ 456-14-4 ]
[ 1616763-24-6 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6579 - 6589

47
[ 1446357-49-8 ]
[ 456-14-4 ]
[ 1616763-32-6 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6579 - 6589

48
C₁₂H₁₀ClNO₅S [ No CAS ]
[ 456-14-4 ]
C₁₈H₁₂FN₃O₂ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2014,vol. 84,p. 1555 - 1560
Zh. Obshch. Khim.,2014,vol. 84,p. 1333 - 1338,6
Zhurnal Obshchei Khimii,2014,vol. 84,p. 1333 - 1338,6

49
methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate [ No CAS ]
[ 456-14-4 ]
C₁₇H₁₀FN₃O₂ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2014,vol. 84,p. 1555 - 1560
Zh. Obshch. Khim.,2014,vol. 84,p. 1333 - 1338,6
Zhurnal Obshchei Khimii,2014,vol. 84,p. 1333 - 1338,6

50
[ 85302-07-4 ]
[ 456-14-4 ]
C₁₄H₁₁FN₂O [ No CAS ]

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 6441 - 6446

51
[ 941-55-9 ]
[ 31067-48-8 ]
[ 456-14-4 ]
(E)-N-(2-(4-fluorophenyl)-6-(naphthalen-1-ylmethyl)pyrimidin-4(3H)-ylidene)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4814 - 4817

52
[ 456-14-4 ]
[ 108-88-3 ]
3-(4-fluorophenyl)-5-phenyl-1,2,4-oxadiazole [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 8857 - 8860

53
[ 456-14-4 ]
[ 67-68-5 ]
[ 1613637-81-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2894 - 2897

54
[ 456-14-4 ]
[ 68-12-2 ]
3-(4-fluorophenyl)-1-methyl-1H-1,2,4-triazole [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2894 - 2897

55
[ 456-14-4 ]
[ 101476-79-3 ]
C₁₈H₁₅FN₆ [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1629 - 1634

56
[ 2579-22-8 ]
[ 456-14-4 ]
[ 76128-69-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In dichloromethane; at 20℃; for 3h;	General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.

Reference： [1]Catalysis Communications,2016,vol. 73,p. 109 - 112
[2]Synthetic Communications,2019,vol. 49,p. 2488 - 2500

57
[ 1846-68-0 ]
[ 456-14-4 ]
C₁₅H₁₇FN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In dichloromethane; at 20℃; for 3h;	General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.

Reference： [1]Synthetic Communications,2019,vol. 49,p. 2488 - 2500
[2]Catalysis Communications,2016,vol. 73,p. 109 - 112

58
[ 456-14-4 ]
[ 104-55-2 ]
[ 76128-69-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With oxygen; potassium hydroxide; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 12h;Green chemistry;	General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120°C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents).

Reference： [1]Chinese Chemical Letters,2016,vol. 27,p. 47 - 50

59
[ 456-14-4 ]
[ 63190-44-3 ]
[ 1038410-94-4 ]
5-cyclopropyl-3-(4-fluorophenyl)-1H-1,2,4-triazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2227 - 2230

60
[ 300-57-2 ]
[ 456-14-4 ]
[ 76128-69-3 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5538 - 5546

61
[ 533-58-4 ]
[ 456-14-4 ]
[ 397-54-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 7920 - 7926

62
[ 95-56-7 ]
[ 456-14-4 ]
[ 397-54-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 7920 - 7926

63
[ 6627-55-0 ]
[ 456-14-4 ]
[ 132292-78-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 7920 - 7926

64
[ 615-58-7 ]
[ 456-14-4 ]
C₁₃H₇BrFNO [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 7920 - 7926

65
[ 292638-84-7 ]
[ 456-14-4 ]
[ 68-12-2 ]
2-(4-fluorophenyl)-N,N-dimethyl-4-phenylpyrimidine-5-carboxamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1289 - 1293
Angew. Chem.,2017,vol. 129,p. 1309 - 1313,5

66
C₂₂H₁₈Cl₃N₃O₂S [ No CAS ]
[ 456-14-4 ]
N-(amino(4-fluorophenyl)methylene)-3-(4-chlorophenyl)-N'-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1126 - 1141

67
[ 456-14-4 ]
[ 545-06-2 ]
C₉H₇Cl₃FN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.2 g		To a solution of 10 g of <strong>[456-14-4]p-fluorobenzamidine hydrochloride</strong> and 100 mL of Methanol, 10.3 g of 30percent solution of NaOMe were added drop wise with stirring at zero degree. After addition,the mixture was stirred for 30mm, then 8.23 g of trichloroacetonitrile were added at zero degree during 30 mm. After the addition, the cooling bath was removed and the reaction mixture was continued to stir overnight. 100 mL of ethyl acetate was added to the reaction mixture and the solid that precipitated in the flask was removed by filtration. The filtered solution was evaporated to yield N-(p-fluorobenzamidyl) trichloroacetamidine as oil. Yields11.2g.

Reference： [1]Patent: WO2016/207161,2016,A1 .Location in patent: Page/Page column 25

68
methyl 3-(dimethylamino)-2-(trifluoromethylsulfinyl)acrylate [ No CAS ]
[ 456-14-4 ]
2-(4-fluorophenyl)-5-(trifluoromethylsulfinyl)pyrimidin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With sodium methylate; In methanol; for 25h;Reflux;	General procedure: To the solution of enaminone 4a-c (2.17 mmol) in methanol (20 mL) amidine hydrohloride (2.17 mmol) followed by solution of sodium methoxide in methanol (5 mL, c = 0.43 M) was added in one portion. Reaction mixture was heated at reflux during the time necessary for the reaction completion (see Table 1 in main text). Solvent was removed in vacuum (0.5 Torr) and product 5 was isolated by column chromatography, HPLC, or crystallization.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1308 - 1311

69
methyl 3-(dimethylamino)-2-(trifluoromethylsulfonyl)acrylate [ No CAS ]
[ 456-14-4 ]
2-(4-fluorophenyl)-5-(trifluoromethylsulfonyl)pyrimidin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium methylate; In methanol; for 15h;Reflux;	General procedure: To the solution of enaminone 4a-c (2.17 mmol) in methanol (20 mL) amidine hydrohloride (2.17 mmol) followed by solution of sodium methoxide in methanol (5 mL, c = 0.43 M) was added in one portion. Reaction mixture was heated at reflux during the time necessary for the reaction completion (see Table 1 in main text). Solvent was removed in vacuum (0.5 Torr) and product 5 was isolated by column chromatography, HPLC, or crystallization.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1308 - 1311

70
[ 456-14-4 ]
[ 15930-53-7 ]
[ 1255516-37-0 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 1292 - 1297

71
[ 456-14-4 ]
[ 6630-33-7 ]
[ 1208259-07-7 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 1292 - 1297

72
[ 456-14-4 ]
[ 501-65-5 ]
6-fluoro-3,4-diphenylisoquinolin-1-amine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3491 - 3498

73
[ 456-14-4 ]
[ 762-21-0 ]
tetraethyl 8-fluoroimidazo[2,1-a]isoquinoline-2,3,5,6-tetracarboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3491 - 3498

74
3-ethoxy-2-(methylsulfonyl)acrylonitrile [ No CAS ]
[ 456-14-4 ]
C₁₁H₁₀FN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine; In ethanol; for 6h;Reflux;	General procedure: A mixture of 0.52 g (3 mmol) of 2-methylsulfonyl-3-ethoxyacrylonitrile 1, 3 mmol of thecorresponding amidine hydrochloride, and 0.84 mL(6 mmol) of triethylamine were refluxed during 6 h in10 mL of ethanol and then kept at room temperatureduring 12 h. The solvent was removed in vacuum, theresidue was treated with water, the precipitate wasfiltered off, dried, and recrystallized.

Reference： [1]Russian Journal of General Chemistry,2017,vol. 87,p. 407 - 413
Zh. Obshch. Khim.,2017,vol. 87,p. 398 - 404,7

75
[ 423-39-2 ]
[ 456-14-4 ]
[ 94-02-0 ]
ethyl 2-(4-fluorophenyl)-4-(perfluoropropyl)-6-phenylpyrimidine-5-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2358 - 2361

76
[ 456-14-4 ]
[ 104-81-4 ]
3-(4-fluorophenyl)-5-(p-tolyl)-1,2,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sulfur; lithium tert-butoxide; In toluene; at 140℃; for 12h;Schlenk technique; Inert atmosphere;	General procedure: A 20 mL of Schlenk tube equipped with a stir bar was charged with benzyl bromides (0.12 mmol), aryl amidines (0.1 mmol), S8 (0.1 mmol), LiOtBu (0.4 mmol). The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 140 °C for 12 h in oil bath. Then the solvent was concentrated in vacuum and the residue was purified by flash column chromatography on silica gel with petroleum ether-EtOAc as the eluent to give the desired product.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2571 - 2573

77
[ 456-14-4 ]
[ 1984-23-2 ]
3-(4-fluorophenyl)-N-(4-nitrophenyl)-1,2,4-selenadiazol-5-amine [ No CAS ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 1613 - 1618

78
[ 948-65-2 ]
[ 456-14-4 ]
(1Z,3Z)-4-(4-fluorophenyl)-2-phenylbenzo[f][1,3,5]triazocin-6(5H)-one [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 6601 - 6604

79
[ 456-14-4 ]
[ 93-55-0 ]
[ 76128-69-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In N,N-dimethyl-formamide; at 120℃; for 12h;Sealed tube;	0.3 mmol of <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> (0.0578 g), 0.75 mmol of phenylacetone (0.1006 g)0.03 mmol of ferrous sulfate heptahydrate (0.0083 g), 0.03 mmol of 1,10-phenanthroline (0.0054 g), tetramethylpiperidine nitrogenOxides (TEMPO) (0.0563 g) was added to a 10 mL tube reaction tube, and 2 mL of N, N-dimethylformamide (DMF) was added as a solvent,Sealed at 120 ° C for 12 hours. After the reaction, the reaction solution was passed through water, ethyl acetate, anhydrous sulfuric acidSodium drying and column chromatography (column chromatography separation conditions: the stationary phase of 300 ~ 400 mesh silica gel powder, the mobile phase ethyl acetate(A) and petroleum ether (B), the mobile phase change program (A: B) is 1: 50 ? 1: 20, 0.0616 g of the reaction product (white solidbody). According to the characterization data, the obtained reaction product 2- (4-fluorophenyl) -4-phenylpyrimidine pure (purity>95percent), the structure is as follows:The product yield was calculated and the result was 82percent.

Reference： [1]Patent: CN106496127,2017,A .Location in patent: Paragraph 0085; 0086; 0087; 0088; 0089; 0090; 0091
[2]Journal of Organic Chemistry,2017,vol. 82,p. 1145 - 1154

80
[ 354-64-3 ]
[ 456-14-4 ]
[ 120-46-7 ]
2-(4-fluorophenyl)-4-phenyl-5-benzoyl 6-trifluoromethylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 4h;	Put <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> and sodium hydroxide into a 25 mL round bottom flask and inject 3 mL of N, N dimethyl Amide solvent, pretreatment and in addition to acid to give free amidine. then, Dibenzoylmethane is added at room temperature Pentafluoride iodine Ethane. Indoor lighting and room temperature reaction 4h, TLC to monitor the reaction end, stop the reaction, the mixture. [0159] molar ratio, dibenzoylmethane: pentafluoroiodoethane: 4-Fluorobenzamidine Hydrochloride: Sodium Hydroxide = 1.0: 1.1: 1.1: 4.1; [0160] 2. The mixture was extracted three times with water, the organic phases were combined, The organic solvent was removed by distillation under reduced pressure to give crude product; [0161] 3. The crude product was chromatographed on silica gel eluting with eluent (petroleum ether: ethyl acetate = 250: 1) to give A white solid was the product of 2- (4-fluorophenyl) -4-phenyl-5-benzoyl 6-trifluoromethylpyrimidine in a yield of 78percent

Reference： [1]Patent: CN106831603,2017,A .Location in patent: Paragraph 0157-0162

81
[ 948-65-2 ]
[ 456-14-4 ]
C₂₁H₁₄FN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(I) oxide; oxygen; In 1-methyl-pyrrolidin-2-one; at 80℃; for 4h;Sealed tube; Green chemistry;	0.3 mmol of <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> (No. 3 corresponding compound, 0.0579 g) was weighed out, 0.4 mmol of 2-phenyl-1-hydrogenindole (corresponding to (30) the corresponding compound, 0.0770 g) And 0.06 mmol cuprous oxide (0.0086 g) in 20 mL of the test tube reaction tube, Plus 3mL N-methyl pyrrolidone as solvent, tube mouth closed with oxygen balloon, Stirring at 80 ° C for 4 hours; after completion of the reaction, The reaction solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate and separated by column chromatography (column chromatography separation conditions: the stationary phase was 300-400 mesh silica powder, the mobile phase was ethyl acetate (A) and petroleum ether (3) The mobile phase change procedure (A: B) was 1: 6) to give 0.0787 g of the reaction product. According to the characterization data, the reaction product was 2-phenyl-4- (4-fluorophenyl) -benzo [1,3,5] triazolidin-5-hydrogen-6-one (purity> 95percent); the product yield was calculated and the result was 78percent.

Reference： [1]Patent: CN106946808,2017,A .Location in patent: Paragraph 0075; 0076; 0077; 0080

82
[ 456-14-4 ]
[ 4197-99-3 ]
2-(4-fluorophenyl)-5-phenyl-5H-chromeno[4,3-d]pyrimidin-5-ol [ No CAS ]
(2-(4-fluorophenyl)-4-phenylpyrimidin-5-yl)(2-hydroxyphenyl)methanone [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 10020 - 10026

83
[ 1634-04-4 ]
[ 456-14-4 ]
[ 1613637-81-2 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6228 - 6231

84
[ 456-14-4 ]
[ 15764-16-6 ]
[ 536-74-3 ]
4-(2,4-dimethylphenyl)-2-(4-fluorophenyl)-6-phenylpyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

85
[ 456-14-4 ]
[ 98-86-2 ]
[ 157141-82-7 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 13239 - 13249

86
[ 292638-84-7 ]
[ 423-39-2 ]
[ 456-14-4 ]
2-(4-fluorophenyl)-4-(perfluoropropyl)-6-phenylpyrimidine [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 2615 - 2618

87
[ 110-18-9 ]
[ 456-14-4 ]
[ 1613637-81-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 2629 - 2633

88
[ 423-39-2 ]
[ 456-14-4 ]
triisopropyl((1-phenylvinyl)oxy)silane [ No CAS ]
2-(4-fluorophenyl)-4-(perfluoropropyl)-6-phenylpyrimidine [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2749 - 2752

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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