Name: 2740-88-7|4-Fluorobenzylisothiocyanate|97%
Brand: Ambeed
SKU: A761319
Price: 22.0 USD
Availability: InStock
Rating: 98 (28 reviews)

1
[ 109-83-1 ]
[ 2740-88-7 ]
[ 61290-74-2 ]

Reference： [1]Current Patent Assignee: SERVIER MONDE; GYOGYSZERKUTATO INTEZET KFT - FR2303532, 1976, B1 [Chem.Abstr., 1977, vol. 86, # 16440][Chem.Abstr., 1977, vol. 86, # 16440]

2
[ 108-02-1 ]
[ 2740-88-7 ]
N-(4-Fluor-benzyl)-dithiocarbaminsaeure-(2-dimethylamino-ethylester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol

Reference： [1]Tweit,R.C. et al. [Journal of Medicinal Chemistry, 1969, vol. 12, # 2, p. 343 - 346]

3
[ 926-39-6 ]
[ 2740-88-7 ]
[ 5777-56-0 ]

Reference： [1]Helvetica Chimica Acta,1966,vol. 49,p. 807 - 831

4
[ 2740-88-7 ]
[ 768-94-5 ]
1-Adamantan-1-yl-3-(4-fluoro-benzyl)-thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran

Reference： [1]Arya,V.P. et al. [Indian Journal of Chemistry, 1972, vol. 10, p. 686 - 690]

5
[ 2740-88-7 ]
[ 141-43-5 ]
[ 61290-32-2 ]

Yield	Reaction Conditions	Operation in experiment
24.6%	In chloroform for 1h; Heating;
	In chloroform

Reference： [1]Reiter; Toldy; Schafer; et al. [European Journal of Medicinal Chemistry, 1980, vol. 15, # 1, p. 41 - 53]
[2]Current Patent Assignee: SERVIER MONDE; GYOGYSZERKUTATO INTEZET KFT - DE2610865, 1976, A1 [Chem.Abstr., 1977, vol. 86, # 16440][Chem.Abstr., 1977, vol. 86, # 16440]
[3]Current Patent Assignee: SERVIER MONDE; GYOGYSZERKUTATO INTEZET KFT - FR2303532, 1976, B1 [Chem.Abstr., 1977, vol. 86, # 16440][Chem.Abstr., 1977, vol. 86, # 16440]

6
[ 2740-88-7 ]
[ 141-43-5 ]
[ 13846-58-7 ]

Yield	Reaction Conditions	Operation in experiment
	(i) Et₂O, (ii) aq. HCl; Multistep reaction;
	With hydrogenchloride 1) CHCl₃, reflux, 2) 90 deg C; Yield given. Multistep reaction;

Reference： [1]Cherbuliez,E. et al. [Helvetica Chimica Acta, 1966, vol. 49, p. 2408 - 2415]
[2]Hirashima, Akinori; Yoshii, Yutaka; Eto, Morifusa [Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 7, p. 1062 - 1065]

7
[ 2740-88-7 ]
[ 156-87-6 ]
[ 13677-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether

Reference： [1]Cherbuliez,E. et al. [Helvetica Chimica Acta, 1967, vol. 50, p. 331 - 346]
[2]Current Patent Assignee: SERVIER MONDE; GYOGYSZERKUTATO INTEZET KFT - FR2303532, 1976, B1 [Chem.Abstr., 1977, vol. 86, # 16440][Chem.Abstr., 1977, vol. 86, # 16440]

8
[ 463-71-8 ]
[ 140-75-0 ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform Heating;

Reference： [1]Hirashima, Akinori; Yoshii, Yutaka; Eto, Morifusa [Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 7, p. 1062 - 1065]

9
[ 1071-23-4 ]
[ 2740-88-7 ]
Phosphorsaeure-<2-(4-fluor-benzyl-thiocarbamoyl-amino)-ethylester> [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol

Reference： [1]Cherbuliez,E. et al. [Helvetica Chimica Acta, 1965, vol. 48, p. 1069 - 1076]

10
[ 2740-88-7 ]
C₈H₈FNO₃S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite

Reference： [1]Sankaran,L.; Rao,P.L.N. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15, p. 386 - 387]

11
[ 2740-87-6 ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 9,10-diphenylanthracene In benzene for 2h; Irradiation;
	With 9,10-diphenylanthracene In benzene Irradiation;

Reference： [1]Wakamatsu, Kan; Dairiki, Jun; Etoh, Tetsuo; Yamamoto, Hiroshi; Yamamoto, Satoshi; Shigetomi, Yasumasa [Tetrahedron Letters, 2000, vol. 41, # 3, p. 365 - 369]
[2]Wakamatsu, Kan; Dairiki, Jun; Etoh, Tetsuo; Yamamoto, Hiroshi; Yamamoto, Satoshi; Shigetomi, Yasumasa [Tetrahedron Letters, 2000, vol. 41, # 3, p. 365 - 369]

Yield	Reaction Conditions	Operation in experiment
	Rk. mit N,N-Dimethyl-2-(mercapto-ethyl)-amin --> N-(4-Fluor-benzyl)-dithiocarbaminsaeure-(2-dimethylamino-ethylester);
	Rk. mit 3-Amino-propanol --> 3-(3-(p-Fluor-benzyl)-thioureido)-propanol;

Yield	Reaction Conditions	Operation in experiment
	(4-Fluor-benzyl)-thiocyanat, 200grad;
	K-thiocyanat, p-Fluorbenzylchlorid;
	Kaliumthiocyanat, p-Fluorbenzylchlorid;

Stage #1: With triethylamine In tetrahydrofuran for 1h; Cooling with ice; Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran for 1h; Cooling with ice;

1 Preparation of benzyl isothiocyanate General procedure: Dissolve 8 mmol of benzylamine in 15 ml of anhydrous tetrahydrofuran solvent, add 5 ml (36 mmol) of triethylamine, place in an ice bath, add 2 ml (33 mmol) of carbon disulfide for 1 hour, and then add 2 g (10.5 mmol) of p-toluenesulfonyl chloride (PTSC) In the flask, withdraw the ice bath again, stop the reaction after one hour of reaction, add 20ml of 0.5mol/L dilute hydrochloric acid to acidify, extract three times with 60ml of anhydrous ether, and separate the organic phase and add anhydrous sulfuric acid after liquid separation After the sodium is dried, add the sample silica gel and spin dry to the column, use petroleum ether flash column chromatography (developing agent: petroleum ether Rf value 0.4-0.6. pyridine ring thioisocyanate, developing agent: ethyl acetate; petroleum ether = 1; 5, Rf value is 0.4-0.5) to obtain a transparent oily liquid (yield 75-80%).

14
[ 2740-88-7 ]
4-[1(H)-imidazol-4-yl]piperidine dihydrobromic acid salt [ No CAS ]
4-(1<i>H</i>-imidazol-4-yl)-piperidine-1-carbothioic acid 4-fluoro-benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 18h;

Reference： [1]Windhorst, Albert D.; Timmerman, Henk; Worthington, Edward A.; Bijloo, Greetje J.; Nederkoorn, Paul H. J.; Menge, Wiro M. P. B.; Leurs, Rob; Herscheid, Jacobus D. M. [Journal of Medicinal Chemistry, 2000, vol. 43, # 9, p. 1754 - 1761]

15
[ 882428-92-4 ]
[ 2740-88-7 ]
C₂₆H₁₅FN₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1-(2-aminophenyl)-9H-β-carboline-3-carboxylic acid amide; 4-fluorobenzylisothiocyanate In dimethyl sulfoxide at 20℃; for 2h; Stage #2: With triethylamine; mercury dichloride In dimethyl sulfoxide at 20℃; for 1h;

Reference： [1]Saha, Biswajit; Kumar, Rishi; Maulik, Prakash R.; Kundu, Bijoy [Tetrahedron Letters, 2006, vol. 47, # 16, p. 2765 - 2769]

16
[ 882428-93-5 ]
[ 2740-88-7 ]
C₂₆H₁₄ClFN₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 1-(2-amino-5-chlorophenyl)-9H-β-carboline-3-carboxylic acid amide; 4-fluorobenzylisothiocyanate In dimethyl sulfoxide at 20℃; for 2h; Stage #2: With triethylamine; mercury dichloride In dimethyl sulfoxide at 20℃; for 1h;

Reference： [1]Saha, Biswajit; Kumar, Rishi; Maulik, Prakash R.; Kundu, Bijoy [Tetrahedron Letters, 2006, vol. 47, # 16, p. 2765 - 2769]

17
C₁₂H₂₀N₂S [ No CAS ]
[ 2740-88-7 ]
4-fluorophenyl-N-(3,4,5-trimethylthiazol-2(3H)-ylidene)methanamine [ No CAS ]
[ 1122-82-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	In toluene at 105℃; for 16h;

Reference： [1]Shin, Dongyun; Lee, Jihoon; Nam, Kee Dal; Hahn, Hoh-Gyu [Tetrahedron Letters, 2007, vol. 48, # 17, p. 3089 - 3092]

18
C₁₇H₂₈N₂S [ No CAS ]
[ 2740-88-7 ]
N-(3-cyclohexyl-4,5-dimethylthiazol-2(3H)-ylidene)(4-fluorophenyl)methanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene at 105℃; for 32h;

Reference： [1]Shin, Dongyun; Lee, Jihoon; Nam, Kee Dal; Hahn, Hoh-Gyu [Tetrahedron Letters, 2007, vol. 48, # 17, p. 3089 - 3092]

19
[ 959909-03-6 ]
[ 2740-88-7 ]
C₂₅H₂₅FN₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 20℃; for 2h;

Reference： [1]Saha, Biswajit; Sharma, Sunil; Kundu, Bijoy [Synthetic Communications, 2007, vol. 37, # 19, p. 3455 - 3470]

20
[ 2740-88-7 ]
[ 13846-58-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 24.6 percent / CHCl₃ / 1 h / Heating 2: 37 percent / aq. HCl / 1 h / Heating

Reference： [1]Reiter; Toldy; Schafer; et al. [European Journal of Medicinal Chemistry, 1980, vol. 15, # 1, p. 41 - 53]

21
[ 2740-88-7 ]
[ 13677-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethyl ether 2: aq. HCl / Heating

Reference： [1]Cherbuliez,E. et al. [Helvetica Chimica Acta, 1967, vol. 50, p. 331 - 346]

22
C₁₃H₁₉N [ No CAS ]
[ 2740-88-7 ]
C₂₂H₂₉FN₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol for 8h;	3 1.79 g (0.01M) of 4-fluorobenzylisothiocyanate are added to 2.09 g (0.01 mole) of N-[1-S(-)-phenylpropyl]-N-isobutylamine in 50 ml of methanol, boiled for 8 hours,

Reference： [1]Current Patent Assignee: PFIZER INC - EP1577294, 2005, A1 Location in patent: Page/Page column 11

23
[ 2740-88-7 ]
[ 345296-38-0 ]
[ 743411-82-7 ]

Yield	Reaction Conditions	Operation in experiment
		21 3-((1-{3-(({((4-fluorophenyl)methyl)amino}thioxo methyl)amino)phenyl}-5-oxopyrrolidin-3-yl)carbonyl amino)-3-(3-pyridyl)propanoic acid, sodium salt EXAMPLE 21 3-((1-{3-(({((4-fluorophenyl)methyl)amino}thioxo methyl)amino)phenyl}-5-oxopyrrolidin-3-yl)carbonyl amino)-3-(3-pyridyl)propanoic acid, sodium salt The title compound was analogously synthesised by the method described in Example 20 from ethyl 3-{(1-(3-aminophenyl)-5-oxopyrrolidin-3-yl)carbonylamino}-3-(3-pyridyl)propanoate (100 mg, 0.25 mmol, 1.0 eq) and 4-fluorobenzyl isothiocyanate (Transworld, 1.26 mmol, 5.0 eq). The title compound was obtained as white solid. Mp: 230° C. (dec.). MS (ES+): 558 (M+H)+.

Reference： [1]Current Patent Assignee: AMGEN INC - US2002/19402, 2002, A1

24
[ 627-01-0 ]
[ 2740-88-7 ]
1-ethyl-3-(4-fluorobenzyl)-2-thioxo-imidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane	22 1-Ethyl-3-(4-fluorobenzyl)-2-thioxo-imidazolidin-4-one EXAMPLE 22 1-Ethyl-3-(4-fluorobenzyl)-2-thioxo-imidazolidin-4-one The title compound was prepared by the procedure described in Example 19 using 9.2 g of N-ethyl glycine, 8.4 g of 4-fluorobenzyl-isothiocyanate, 10.1 g of triethylamine, and 150 mL of methylene chloride. Purification was achieved through crystallization from ethyl acetate/hexane mixture. Title compound (4.85 g) was obtained as a white solid, m.p. 73°-76° C. Anal. Calcd. for. C12 H13 F N2 O S: C, 57.12; H, 5.19; N, 11.10 Found: C, 56.97; H,5.15; N, 11.06. Mass spectrum (EI, M.+) m/z 252.
	With triethylamine In dichloromethane	6 1-Ethyl-3-(4-fluorobenzyl)-2-thioxo-imidazolidin-4-one EXAMPLE 6 1-Ethyl-3-(4-fluorobenzyl)-2-thioxo-imidazolidin-4-one The title compound was prepared by the procedure described in Example 4 using 9.2 g of N-ethyl glycine, 8.4 g of 4-fluorobenzyl-isothiocyanate, 10.1 g of triethylamine, and 150 mL of methylene chloride. Purification was achieved through crystallization from ethyl acetate/hexane mixture. Title compound (4.85 g) was obtained as a white solid, m.p. 73°-76° C. Anal. Calcd. for. C12 H13 F N2 O S: C, 57.12; H, 5.19; N, 11.10 Found: C, 56.97; H,5.15; N, 11.06. Mass spectrum (EI, M.+) m/z 252.

Reference： [1]Current Patent Assignee: PFIZER INC - US5554607, 1996, A
[2]Current Patent Assignee: PFIZER INC - US5783707, 1998, A

25
[ 108038-52-4 ]
[ 2740-88-7 ]
C₁₆H₁₄FN₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol for 2h; Heating / reflux;	23 N-(4-fluorobenzyl)-5-(1 H-benzo[d]imidazol-5-yl)-1 ,3,4-oxadiazol-2-amineIII (0.352g, 2 mmol)) and 4-fluorobenzylisothiocyanate (0.274mL, 2mmol) were dissolved in 20 mL of EtOH and kept under reflux for 2h. After that the solvent was removed and the remaining oil was re-dissolved in 30 mL of THF. After the addition of DCC (1.5 eq) the solution was refluxed for 1 h. The solvent was removed and the remaining oil was purified by means of flash chromatography on AI2O3 utilizing a CHCI3/MeOH gradient.Yield: 0.162 g (26%), MS: m/z 310.1 [M+H]+, HPLC Method [B], (214 nm): rt 9.83 min (95.7%)

Reference： [1]Current Patent Assignee: VIVORYON THERAPEUTICS AG - WO2008/65141, 2008, A1 Location in patent: Page/Page column 66

26
[ 2740-88-7 ]
[ 1244403-35-7 ]
[ 938042-51-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	In toluene at 105℃; for 20h;

Reference： [1]Location in patent: experimental part Shin, Dongyun; Lee, Jihoon; Hahn, Hoh-Gyu [Tetrahedron, 2010, vol. 66, # 30, p. 5707 - 5713]

27
[ 2740-88-7 ]
C₉H₉ClFNS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine In hexane at -15℃;

Reference： [1]Location in patent: scheme or table Kang, Nam Sook; Lee, Gil Nam; Kim, Chi Hyun; Bae, Myung Ae; Kim, Ikyon; Cho, Young Sik [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 533 - 537]

28
[ 2740-88-7 ]
[ 1055193-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: chlorine / hexane / -15 °C 2: hexane / 20 °C

Reference： [1]Kang, Nam Sook; Lee, Gil Nam; Kim, Chi Hyun; Bae, Myung Ae; Kim, Ikyon; Cho, Young Sik [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 533 - 537]

29
[ 32315-10-9 ]
[ 140-75-0 ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: para-fluorobenzylamine With 1,4-diaza-bicyclo[2.2.2]octane; carbon disulfide at 20℃; for 12h; Stage #2: bis(trichloromethyl) carbonate Reflux;

Reference： [1]Location in patent: scheme or table Chen, Kan; Tan, Zhiwu; He, Meizi; Li, Jiebo; Tang, Shixing; Hewlett, Indira; Yu, Fei; Jin, Yinxue; Yang, Ming [Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33]

30
[ 2740-88-7 ]
[ 723-46-6 ]
[ 897514-14-6 ]

Yield	Reaction Conditions	Operation in experiment
77.7%	In ethanol at 20℃; for 24h;

Reference： [1]Location in patent: scheme or table Chen, Kan; Tan, Zhiwu; He, Meizi; Li, Jiebo; Tang, Shixing; Hewlett, Indira; Yu, Fei; Jin, Yinxue; Yang, Ming [Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33]

31
[ 2740-88-7 ]
[ 16315-59-6 ]
[ 1352552-23-8 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: 4-fluorobenzylisothiocyanate; N,N-dimethylaminophenyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

32
[ 2740-88-7 ]
[ 1943-67-5 ]
[ 1352552-22-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 4-fluorobenzylisothiocyanate; 4-(t-butyl)phenyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

33
[ 2740-88-7 ]
[ 621-29-4 ]
[ 1055193-18-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 4-fluorobenzylisothiocyanate; 3-tolyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

34
[ 2740-88-7 ]
[ 104-12-1 ]
[ 1055193-25-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 4-fluorobenzylisothiocyanate; p-chlorphenylisocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

35
[ 2740-88-7 ]
[ 103-71-9 ]
[ 1055193-29-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 4-fluorobenzylisothiocyanate; phenyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

36
[ 2740-88-7 ]
[ 622-58-2 ]
[ 883050-24-6 ]

Yield	Reaction Conditions	Operation in experiment
41%		General Procedure for synthesis of 1,2,4-thiadiazolidine-3,5-dionesA stirred solution of isocyanate (1 mmol) and isothiocyanate (1 mmol) in THF (5 mL) was cooled to 0 C. Sulfuryl chloride (1 mmol) was added slowly (either as straight or as a 1 M solution in CH2C2) and the mixture was allowed to warm to room temperature and stirred overnight. The reaction was then opened to the air and stirred for 30 minutes before the solvent was removed under reduced pressure. Flash chromatography (0-20% ethyl acetate in pet ether) was used to purify the crude reaction mixture.2-p-tolyl-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione (1a) Yield=41%. 1H NMR (400 MHz, CDCl3) delta 2.35 (s, 3H), 4.87 (s, 2H), 7.01-7.05 (m, 2H), 7.20-7.22 (m, 2H), 7.35-7.38 (m, 2H), 7.48-7.51 (m, 2H). 13C NMR (100 MHz, CDCl3) delta 20.9, 45.3, 115.6 (d, JCF=21.6 Hz), 123.7, 130.0, 130.9 (d, JCF=3.3 Hz), 131.1, (d, JCF=8.3 Hz), 133.0, 137.3, 151.0, 162.7 (d, JCF=247.4 Hz), 165.1; anal. (C16H13FN2O2S); CHN

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 146 - 150
[2]Patent: US2012/277273,2012,A1 .Location in patent: Page/Page column 22-23

37
[ 2740-88-7 ]
[ 5416-93-3 ]
[ 1055193-27-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 4-fluorobenzylisothiocyanate; 4-Methoxyphenyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

38
[ 2740-88-7 ]
[ 102-36-3 ]
[ 1352551-94-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: 4-fluorobenzylisothiocyanate; 3,4-dichlorophenylisocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

39
[ 2740-88-7 ]
[ 2909-38-8 ]
[ 1055193-20-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 4-fluorobenzylisothiocyanate; m-chlorophenyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

40
[ 2740-88-7 ]
[ 329-01-1 ]
[ 1352551-95-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 4-fluorobenzylisothiocyanate; 1-isocyanato-3-trifluoromethyl-benzene With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

41
[ 2740-88-7 ]
[ 109-90-0 ]
[ 1352552-10-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 4-fluorobenzylisothiocyanate; ethyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

42
[ 2740-88-7 ]
[ 111-36-4 ]
[ 1055193-39-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 4-fluorobenzylisothiocyanate; n-butyl isocyanide With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

43
[ 2740-88-7 ]
[ 56651-57-1 ]
[ 1352551-96-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 4-fluorobenzylisothiocyanate; 4-tolylmethyl isocyanate With sulfuryl dichloride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran for 0.5h;

Reference： [1]Turner, Emma M.; Blazer, Levi L.; Neubig, Richard R.; Husbands, Stephen M. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 146 - 150]

44
[ 75-15-0 ]
[ 140-75-0 ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: carbon disulfide; para-fluorobenzylamine In diethyl ether for 0.25h; Cooling with ice; Stage #2: With dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 24h;
96%	Stage #1: carbon disulfide; para-fluorobenzylamine With triethylamine In ethanol at 20℃; for 1h; Stage #2: With dmap; di-<i>tert</i>-butyl dicarbonate at 0 - 20℃; for 4h;	The synthesis of 1-fluoro-4-(isothiocyanatomethyl)benzene (SF14) General procedure: The solution of 3-(2-aminoethyl)indole (80.1 mg, 0.5 mmol) in EtOH (1 mL, 0.5 M) was treated with carbon disulfide (114.2 mg, 1.5 mmol) followed by triethylamine (50.6 mg, 0.5 mmol). After stirring at room temperature for 1 hour, Boc2O (109.1 mg, 0.5 mmol) and DMAP (1.8 mg, 0.015 mmol) was added to the reaction mixture at 0 °C. The reaction was stirred at room temperature for 2 hours and leave it additionally 2 hour to remove SCO gas. After the reaction completes, the crude product was extracted with ethyl acetate (50 mL) and purified by silica gel chromatography to afford 3-(2-isothiocyanatoethyl)-1H-indole (89.9 mg, 89%).
76.2%	Stage #1: carbon disulfide; para-fluorobenzylamine With triethylamine In tetrahydrofuran at 0℃; Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran at 20℃;	8 Synthesis of 1-fluoro-4-(isothiocyanatomethyl)benzene (8.2). To a solution of (4-fluorophenyl)methanamine (8.3, 5.0 g, 39.96 mmol) in tetrahydrofuran (40 mL) was added carbon disulfide (3.65 g, 47.96 mmol) and triethylamine (4.85 g, 47.96 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 30 minutes (white precipitate formation was observed) and a 1.0 M solution of p-toluene sulfonyl chloride in tetrahydrofuran (40 mL) was added. The reaction mixture was stirred at room temperature for 1 h and 50% HC1 in water (100 mL) was added. The mixture was extracted with diethyl ether (250 mL) and the layers were separated. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product. The crude product was purified by silica gel (100-200 mesh) column chromatography eluting with hexanes to afford 1-fluoro-4- (isothiocyanatomethyl) benzene (8.2). Yield; 5.12 g, 76.2%.

75%	With tert.-butylhydroperoxide; dmap In methanol; water at 0℃;	4 Preparation of 4-fluorobenzyl isothiocyanate Dissolve 4-fluorobenzylamine (63mg, 0.5mmol) in 5mL methanol at 0°C,After that, 4-dimethylaminopyridine (6mg, 0.05mmol),Carbon disulfide (133 mg, 1.75 mmol) and tert-butyl hydroperoxide (96 mg, 0.75 mol, 70% in H2O).The reaction continued to stir at 0°C. When TLC indicated that the conversion of the starting material was completed, the solvent was distilled off under reduced pressure.Water was added to the crude reaction system and extracted with petroleum ether.The obtained crude product was purified by column chromatography with 1:20 ethyl acetate/petroleum ether to obtain the target molecule (63 mg, 75% yield).The molar ratio of the primary amine, base catalyst, carbon disulfide and oxidant is 1:0.1:3.5:1.5.
53%	With tert.-butylhydroperoxide; dmap; tetra-(n-butyl)ammonium iodide In methanol; water at 0℃;	General procedure for the synthesis of isothiocyanates General procedure: To a solution of amine (0.5 mmol) in MeOH (2.5 mL) at 0 °C was added Bu4NI (18 mg, 0.05 mmol), DMAP (6 mg, 0.05 mmol) sequentially. The solution was stirred at 0 °C for 10 min. After that, 70% aq. TBHP (96 mg, 0.75 mmol), CS2 (133 mg, 1.75 mmol) was added. The solution was stirred at 0 °C for 6-18 h. Upon consumption of the amine, 50 mL EtOAc was added, the organic phase was washed with H2O (10 mL) and dried with Na2SO4. After concentration of the organic phase under reduced pressure, the residue was purified by column chromatography on silica gel using EtOAc/ PE = 1:20 to give the desired product.
	Stage #1: carbon disulfide; aniline With triethylamine In tetrahydrofuran at 0 - 20℃; for 1.75h; Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran at 0 - 20℃;	4 Example 4: Synthesis of Thiorurea Derivatives of Emetine[0055] The general reaction scheme for synthesis of thiourea analogs of emetine is shown in Scheme 12 below.SCHEME 1211 a-n[0056] Isothiocyanates were first synthesized according to JOC: 72, 3969-3971 (2007), which is incorporated herein by reference, with slight modification. To a solution of appropriate amine (16.0 mmol, 1 molar equiv.) in THF (15 mL) at 0°C was added triethylamine (10.0 mL). The resultant mixture was kept stirring while CS2 (34.0 mmol, 2 molar equiv.) was added dropwise over about thirty minutes at 0°C. The mixture was allowed to stir at this temperature for fifteen minutes after which it was stirred at room temperature for one hour. The reaction mixture was then cooled to 0°C again while stirring continued, and a solution of tosyl chloride (20.8 mmol, 1.3 molar equiv) in THF was added gently. The reaction mixture was allowed to warm up to room temperature, stirred for an additional hour at room temperature and then 20 mL IN HC1 was added while stirring continued. This was followed by 25 mL diethyl ether and the reaction was stirred for another five minutes. The aqueous layer was separated and then back extracted with diethyl ether (2 X 20 mL). The combined organic layers were dried over Na2SC>4, solvent evaporated in vacuo, and the crude product was purified by column chromatography eluting with hexanes over silica gel to give pure isothiocyanate which was used in the next synthesis step.

Reference： [1]Location in patent: experimental part Cao, Sheng-Li; Xu, Hong; Wang, Yao; Liao, Ji; Zhang, Jing-Jing; Li, Zhong-Feng; Guo, Yan-Wen; Li, Xiao-Rong; Cui, Xue-Mei; Xu, Xingzhi [Medicinal Chemistry, 2012, vol. 8, # 2, p. 163 - 173]
[2]Kim, Taejung; Kim, Young-Joo; Han, Im-Ho; Lee, Dahae; Ham, Jungyeob; Kang, Ki Sung; Lee, Jae Wook [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 1, p. 62 - 66]
[3]Current Patent Assignee: GOSSAMER BIO INC - WO2018/126072, 2018, A1 Location in patent: Paragraph 0231
[4]Current Patent Assignee: CHINA NORTH INDUSTRIES GROUP CORPORATION - CN111875524, 2020, A Location in patent: Paragraph 0062-0066
[5]Rong, Hao-Jie; Chen, Tao; Xu, Ze-Gang; Su, Tian-Duo; Shang, Yu; Wang, Yong-Qiang; Yang, Cui-Feng [Tetrahedron Letters, 2021, vol. 68]
[6]Current Patent Assignee: HOWARD UNIVERSITY - WO2012/162175, 2012, A1 Location in patent: Page/Page column 27

45
6-(aminomethyl)-2-methylquinazolin-4-(3H)-one dihydrochloride [ No CAS ]
[ 2740-88-7 ]
[ 1384521-72-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 6-(aminomethyl)-2-methylquinazolin-4-(3H)-one dihydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-fluorobenzylisothiocyanate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Location in patent: experimental part Cao, Sheng-Li; Xu, Hong; Wang, Yao; Liao, Ji; Zhang, Jing-Jing; Li, Zhong-Feng; Guo, Yan-Wen; Li, Xiao-Rong; Cui, Xue-Mei; Xu, Xingzhi [Medicinal Chemistry, 2012, vol. 8, # 2, p. 163 - 173]

46
[ 2740-88-7 ]
[ 1378372-01-0 ]
[ 1384521-63-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 6-(hydroxymethyl)-2-methyl-1,4-dihydroquinazolin-4-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: 4-fluorobenzylisothiocyanate In N,N-dimethyl-formamide at 20℃; for 48h;

Reference： [1]Location in patent: experimental part Cao, Sheng-Li; Xu, Hong; Wang, Yao; Liao, Ji; Zhang, Jing-Jing; Li, Zhong-Feng; Guo, Yan-Wen; Li, Xiao-Rong; Cui, Xue-Mei; Xu, Xingzhi [Medicinal Chemistry, 2012, vol. 8, # 2, p. 163 - 173]

47
[ 2740-88-7 ]
[ 1378372-01-0 ]
[ 1384521-64-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 6-(hydroxymethyl)-2-methyl-1,4-dihydroquinazolin-4-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: 4-fluorobenzylisothiocyanate In N,N-dimethyl-formamide at 20℃; for 48h;

Reference： [1]Location in patent: experimental part Cao, Sheng-Li; Xu, Hong; Wang, Yao; Liao, Ji; Zhang, Jing-Jing; Li, Zhong-Feng; Guo, Yan-Wen; Li, Xiao-Rong; Cui, Xue-Mei; Xu, Xingzhi [Medicinal Chemistry, 2012, vol. 8, # 2, p. 163 - 173]

48
[ 2740-88-7 ]
[ 622-58-2 ]
C₁₉H₂₁FN₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sulfuryl dichloride / dichloromethane; tetrahydrofuran / 0 - 20 °C 1.2: air / 0.5 h 2.1: chloroform / 120 h

Reference： [1]Current Patent Assignee: UNIVERSITY OF BATH - US2012/277273, 2012, A1

49
[ 2740-88-7 ]
diethyl cis-2-benzoyl-3-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate [ No CAS ]
(4,5-trans, 2Z)-diethyl 4-benzoyl-2-((4-fluorobenzyl)imino)-5-(4-nitrophenyl)dihydrothiophene-3,3(2H)-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With aluminum (III) chloride In nitromethane at 30℃; for 0.0833333h; Schlenk technique;

Reference： [1]Sun, Yongxian; Yang, Gaosheng; Chai, Zhuo; Mu, Xiaolong; Chai, Jun [Organic and Biomolecular Chemistry, 2013, vol. 11, # 45, p. 7859 - 7868]

50
[ 2740-88-7 ]
[ 140-75-0 ]
(5Z)-3-(4-fluorobenzyl)-2-(4-fluorobenzylimino)-5-(4-methoxybenzylidene)thiazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol / 0.5 h / 20 °C 2: sodium acetate / ethanol / 0.33 h / 120 °C / Microwave irradiation

Reference： [1]Sarkis, Manal; Tran, Diem-Ngan; Dasso Lang, Maria Chiara; Garbay, Christiane; Braud, Emmanuelle [Synlett, 2014, vol. 25, # 9, p. 1257 - 1262]

51
[ 2740-88-7 ]
[ 140-75-0 ]
[ 883017-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; for 0.5h;	Optimized Procedure for the Synthesis of 5-Arylidene-2-aryliminothiazolidin-4-ones General procedure: In a 10 mL reaction vial, the amine (0.5 mmol) was added to a solution of isothiocyanate (0.5 mmol) in absolute EtOH (1 mL). The formation of the thiourea was achieved either at r.t. or by irradiating the reaction mixture for the duration indicated for each compound at a maximum power of 90 W and 120 °C. Anhydrous NaOAc (61.5 mg, 1.5 equiv), chloroacetyl chloride (59.7 μL, 1.5 equiv), and aldehyde (1 equiv) were added successively. The reaction mixture was then irradiated for 20 min at a maximum power of 30 W and 120 °C. The precipitate was filtered and dissolved in CH2Cl2. The organic phase was washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. Either crystallization from EtOH or purification by flash chromatography afforded the corresponding 5-arylidene-2-aryliminothiazolidin-4-ones.

Reference： [1]Sarkis, Manal; Tran, Diem-Ngan; Dasso Lang, Maria Chiara; Garbay, Christiane; Braud, Emmanuelle [Synlett, 2014, vol. 25, # 9, p. 1257 - 1262]

52
[ 2740-88-7 ]
[ 1601751-76-1 ]
1-(4-Fluorobenzyl)-3-(1-(5-nitrothiazol-2-yl)piperidin-4-yl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.66%	With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h;	20 General procedure for the synthesis of urea/thiourea derivatives (4-25) To a solution of 1-(5-nitrothiazol-2-yl)piperidin-4-amine (1mmol) in dry dimethylformamide (3mL) was added triethylamine (2mmol) and corresponding isocyanate/isothiocyanate (1.1mmol) at 0°C. The reaction mixture was slowly warmed to rt and stirred at rt for 6h (monitored by TLC & LCMS for completion). The reaction mixture was washed with water (2mL), brine (2mL), dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was then either recrystallised from diethylether or purified by column chromatography. 4.2.4.20 1-(4-Fluorobenzyl)-3-(1-(5-nitrothiazol-2-yl)piperidin-4-yl)thiourea (23) The compound was synthesized according to the general procedure using 1-(5-nitrothiazol-2-yl)piperidin-4-amine (0.1 g, 0.438 mmol), triethylamine (0.089 g, 0.88 mmol), and 4-fluorobenzyl isothiocyanate (0.073 g, 0.482 mmol) to afford 23 (0.143 g, 82.66%) as pale yellow solid. Mp: 177-179 °C. 1H NMR (CDCl3): δH 1.38-3.16 (m, 9H), 4.21 (s, 2H), 7.16-7.38 (m, 4H), 8.42 (s, 1H). 13C NMR (CDCl3): δc 181, 172, 160.7, 147.6, 135.7, 133.5, 128.7, 115.4, 51.6, 50.7, 47, 32. ESI-MS m/z 396.1 (M+H)+. Anal. Calcd for C16H18FN5O2S2: C, 48.59; H, 4.59; N, 17.71. Found: C, 48.62; H, 4.56; N, 17.74.

Reference： [1]Jeankumar, Variam Ullas; Kotagiri, Sonali; Janupally, Renuka; Suryadevara, Priyanka; Sridevi, Jonnalagadda Padma; Medishetti, Raghavender; Kulkarni, Pushkar; Yogeeswari, Perumal; Sriram, Dharmarajan [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 3, p. 588 - 601]

53
[ 2740-88-7 ]
[ 936-02-7 ]
4-(4-fluorobenzyl)-1-(2-hydroxybenzoyl)thiosemicarbazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol for 0.25h; Reflux;

Reference： [1]Plech, Tomasz; Paneth, Agata; Kapro, Barbara; Kosikowska, Urszula; Malm, Anna; Strzelczyk, Aleksandra; Staczek, Pawel [Chemical Biology and Drug Design, 2015, vol. 85, # 3, p. 315 - 325]

54
[ 2740-88-7 ]
[ 5818-06-4 ]
4-(4-fluorobenzyl)-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol for 0.25h; Reflux;

Reference： [1]Plech, Tomasz; Paneth, Agata; Kapro, Barbara; Kosikowska, Urszula; Malm, Anna; Strzelczyk, Aleksandra; Staczek, Pawel [Chemical Biology and Drug Design, 2015, vol. 85, # 3, p. 315 - 325]

55
[ 10065-72-2 ]
[ 2740-88-7 ]
C₁₂H₁₅FN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at -20℃; enantioselective reaction;	4.3 4.2.1 General procedure for the preparation of α-amino acid thioureas (1a-1l). General procedure: To a mixture of amine (1mmol) and K2CO3 (0.28 g, 2 mmol) in 2 mL of water, 0.09 g of CS2 (1.2 mmol) in 1 ml of DMF was added dropwise in a period of 20-30 min at room temperature. After the addition was complete, the mixture was stirred for several hours until complete conversion was determined by TLC. Then, the reaction mixture was cooled to 0 °C and a solution of 0.09 g of Cyanuric chloride (TCT) (0.5 mmol) in 2 mL of CH2Cl2 was added dropwise. After the addition was complete, the mixture was stirred for another 0.5 h to finish the reaction. The reaction mixture was then basified to pH >11 with 6N NaOH to obtain a clear solution. The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and the solvent was removed in vacuo. The residual was purified by flash chromatography through a short silica column using petroleum ether as eluent to give corresponding isothiocyanates (5a-5g). Then the isothiocyanate was added to a solution of the α-amino acid methyl ester (1.2mmol) in CH2Cl2 dropwise at -20°C. After the addition was completed, the reaction solution was stirred for 30 min. Then the reaction mixture was taken up with CH2Cl2, after being dried with MgSO4 and condensed, α-amino acid thioureas (1a-1l) were obtained without further purification.

Reference： [1]Chen, Yu; Su, Li; Yang, Xinying; Pan, Wenyan; Fang, Hao [Tetrahedron, 2015, vol. 71, # 49, p. 9234 - 9239]

56
[ 140-75-0 ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / water; N,N-dimethyl-formamide / 20 °C 2: 1,3,5-trichloro-2,4,6-triazine / water; N,N-dimethyl-formamide; dichloromethane / 0 °C

Reference： [1]Chen, Yu; Su, Li; Yang, Xinying; Pan, Wenyan; Fang, Hao [Tetrahedron, 2015, vol. 71, # 49, p. 9234 - 9239]

57
C₈H₇FNS₂^(1-)*K⁽¹⁺⁾ [ No CAS ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water; N,N-dimethyl-formamide at 0℃;	4.2 4.2.1 General procedure for the preparation of α-amino acid thioureas (1a-1l). General procedure: To a mixture of amine (1mmol) and K2CO3 (0.28 g, 2 mmol) in 2 mL of water, 0.09 g of CS2 (1.2 mmol) in 1 ml of DMF was added dropwise in a period of 20-30 min at room temperature. After the addition was complete, the mixture was stirred for several hours until complete conversion was determined by TLC. Then, the reaction mixture was cooled to 0 °C and a solution of 0.09 g of Cyanuric chloride (TCT) (0.5 mmol) in 2 mL of CH2Cl2 was added dropwise. After the addition was complete, the mixture was stirred for another 0.5 h to finish the reaction. The reaction mixture was then basified to pH >11 with 6N NaOH to obtain a clear solution. The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and the solvent was removed in vacuo. The residual was purified by flash chromatography through a short silica column using petroleum ether as eluent to give corresponding isothiocyanates (5a-5g). Then the isothiocyanate was added to a solution of the α-amino acid methyl ester (1.2mmol) in CH2Cl2 dropwise at -20°C. After the addition was completed, the reaction solution was stirred for 30 min. Then the reaction mixture was taken up with CH2Cl2, after being dried with MgSO4 and condensed, α-amino acid thioureas (1a-1l) were obtained without further purification.

Reference： [1]Chen, Yu; Su, Li; Yang, Xinying; Pan, Wenyan; Fang, Hao [Tetrahedron, 2015, vol. 71, # 49, p. 9234 - 9239]

58
[ 2740-88-7 ]
(S)-3-(4-fluorobenzyl)-5-methyl-2-thioxoimidazolidin-4-one [ No CAS ]
(R)-3-(4-fluorobenzyl)-5-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane / -20 °C 2: sodium hydride / tetrahydrofuran / -60 °C / Inert atmosphere

Reference： [1]Chen, Yu; Su, Li; Yang, Xinying; Pan, Wenyan; Fang, Hao [Tetrahedron, 2015, vol. 71, # 49, p. 9234 - 9239]

59
[ 219562-44-4 ]
[ 2740-88-7 ]
(2S,3S,4S,5S)-N-(4-fluorobenzyl)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine-1-carbothioamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In pyridine at 20℃; for 21h;	2 4.1.1.1 General procedure for the synthesis of thiourea derivatives (2a-t) General procedure: To a stirred solution of L-DMDP (0.3 mmol) in pyridine (4.4 ml), NEt3 (0.36 mmol) was added corresponding isothiocyanate (0.33 mmol) at room temperature, and the reaction mixture was stirred for 21 h. The solvent was evaporated and the residue was co-evaporated several times with toluene. The crude product was chromatographed on silica gel (2 g, CH2Cl2/MeOH = 20:1) to give 2a-t.

Reference： [1]Miyawaki, Shota; Hirokami, Yuki; Kinami, Kyoko; Hoshino, Masako; Minehira, Daisuke; Miyamoto, Daiki; Nash, Robert J.; Fleet, George W.J.; Adachi, Isao; Toyooka, Naoki; Kato, Atsushi [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 107 - 115]

60
[ 219562-44-4 ]
[ 2740-88-7 ]
(5S,6S,7S,7aR)-3-[(4-fluorobenzyl)imino]-5-(hydroxymethyl)tetrahydro-pyrrolo[1,2-c]-thiazole-6,7-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / pyridine / 21 h / 20 °C 2: hydrogenchloride / methanol; water / 24 h / 50 °C

Reference： [1]Miyawaki, Shota; Hirokami, Yuki; Kinami, Kyoko; Hoshino, Masako; Minehira, Daisuke; Miyamoto, Daiki; Nash, Robert J.; Fleet, George W.J.; Adachi, Isao; Toyooka, Naoki; Kato, Atsushi [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 107 - 115]

61
[ 2740-88-7 ]
ethyl r-1,2-oxo-cis-4,cis-6-Diphenyl-3-oxabicyclo[3.1.0]hexane-1-carboxylate [ No CAS ]
ethyl 4-((4-fluorobenzyl)imino)-3-oxo-1,6-diphenylhexahydrothieno[3,4-c]furan-3a-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With iron(III) chloride In 1,2-dichloro-ethane at 30℃; for 1.2h; Schlenk technique;

Reference： [1]Feng, Manli; Yang, Pengfei; Yang, Gaosheng; Chen, Wenlong; Chai, Zhuo [Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 174 - 184]

62
[ 2740-88-7 ]
(Z)-4-(5-((3-(4-fluorobenzyl)-4-oxo-2-thioxooxazolidin-5-ylidene)methyl)furan-2-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0 - 20 °C 2: acetic acid; sodium acetate / 16 h / 120 °C

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2018/126072, 2018, A1

63
[ 2740-88-7 ]
(Z)-3’-((3-(4-fluorobenzyl)-4-oxo-2-thioxooxazolidin-5-ylidene)methyl)-[1,1’-biphenyl]-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0 - 20 °C 2: acetic acid; sodium acetate / 96 h / 120 °C

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2018/126072, 2018, A1

64
[ 2740-88-7 ]
methyl (Z)-5-(5-((3-(4-fluorobenzyl)-4-oxo-2-thioxooxazolidin-5-ylidene)methyl)furan-2-yl)picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0 - 20 °C 2: acetic acid; sodium acetate / 96 h / 120 °C

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2018/126072, 2018, A1

65
[ 96-35-5 ]
[ 2740-88-7 ]
3-(4-fluorobenzyl)-2-thioxooxazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	at 0 - 20℃;	8 Synthesis of 3-(4-fluorobenzyl)-2-thioxooxazolidin-4-one (8.1). To a solution of 1-fluoro-4-isothiocyanatomethyl benzene (8.2, 1.2 g, 7.18 mmol) in acetonitrile (30 mL) was added potassium carbonate (2.47 g, 17.90 mmol) in one portion followed by addition of methyl glycolate (0.646 g, 7.18 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 16 h. After completion, water (50 mL) was added to the reaction and the mixture was extracted with diethyl ether (200 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to get the crude product. The crude product was purified by silica gel (100-200 mesh) column chromatography eluting with 5-10% ethyl acetate in hexanes to afford 3-(4-fluorobenzyl)-2-thioxooxazolidin-4-one (8.1). Yield; 0.160 g, 10%.

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2018/126072, 2018, A1 Location in patent: Paragraph 0231; 0232

66
[ 2740-88-7 ]
[ 86-84-0 ]
4-(4-fluorobenzyl)-2-(naphthalen-1-yl)-1,2,4-thiadiazolidine-3,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / tetrahydrofuran / 0 - 20 °C 2: air / tetrahydrofuran / 0.5 h

Reference： [1]Yang, Teng; Zhang, Tao; Guan, Xiang-Na; Dong, Ze; Lan, Lefu; Yang, Song; Yang, Cai-Guang [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8442 - 8457]

67
[ 2740-88-7 ]
[ 86-84-0 ]
C₁₉H₁₃Cl₂FN₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In tetrahydrofuran at 0 - 20℃;

Reference： [1]Yang, Teng; Zhang, Tao; Guan, Xiang-Na; Dong, Ze; Lan, Lefu; Yang, Song; Yang, Cai-Guang [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8442 - 8457]

68
[ 2740-88-7 ]
[ 130609-21-1 ]
2-acetamido-5-N-(N'-p-fluorobenzylthiocarbamoyl)-1,2-dideoxynojirimycin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h; chemoselective reaction;

Reference： [1]Ashmus, Roger A.; Busmann, Jil A.; Davies, Gideon J.; Foster, Leonard J.; García Fernández, José M.; González-Cuesta, Manuel; Madden, Zarina; Males, Alexandra; Ortiz Mellet, Carmen; Proceviat, Cameron; Rogalski, Jason C.; Sidhu, Peter; Vocadlo, David J. [Journal of the American Chemical Society, 2022, vol. 144, # 2, p. 832 - 844]

69
[ 2740-88-7 ]
[ 130609-21-1 ]
(Z)-2-acetamido-5-N,6-S-(N'-p-fluorobenzyliminomethylidene)-1,2-dideoxy-6-thionojirimycin hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C 2: hydrogenchloride / methanol; water / 20 °C / pH 1

Reference： [1]Ashmus, Roger A.; Busmann, Jil A.; Davies, Gideon J.; Foster, Leonard J.; García Fernández, José M.; González-Cuesta, Manuel; Madden, Zarina; Males, Alexandra; Ortiz Mellet, Carmen; Proceviat, Cameron; Rogalski, Jason C.; Sidhu, Peter; Vocadlo, David J. [Journal of the American Chemical Society, 2022, vol. 144, # 2, p. 832 - 844]

70
[ 96989-50-3 ]
[ 140-75-0 ]
[ 2740-88-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane at 20℃; for 40h; Inert atmosphere;

Reference： [1]Fanta, Claire C.; Tlusty, Kaitlyn J.; Pauley, Sarah E.; Johnson, Amanda L.; Benjamin, Genevieve A.; Yseth, Taylor K.; Bunde, Michaela M.; Pierce, Paul T.; Wang, Shirley; Vitiello, Peter F.; Mays, Jared R. [ChemMedChem, 2022, vol. 17, # 14]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	2740-88-7	MDL No. :	MFCD00041115
Formula :	C₈H₆FNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LPVNPJMEWWUFHD-UHFFFAOYSA-N
M.W :	167.20	Pubchem ID :	75963
Synonyms :

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.34
TPSA :	44.45 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.01 cm/s

[ CAS No. 2740-88-7 ] {[proInfo.proName]}

Quality Control of [ 2740-88-7 ]

Related Doc. of [ 2740-88-7 ]

Product Details of [ 2740-88-7 ]

Calculated chemistry of [ 2740-88-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2740-88-7 ]

Application In Synthesis of [ 2740-88-7 ]

[ 2740-88-7 ] Synthesis Path-Downstream 1~70

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.33
Log Po/w (XLOGP3) :	3.26
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	3.7
Log Po/w (SILICOS-IT) :	4.2
Consensus Log Po/w :	3.24

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

Log S (ESOL) :	-3.2
Solubility :	0.105 mg/ml ; 0.000628 mol/l
Class :	Soluble
Log S (Ali) :	-3.87
Solubility :	0.0227 mg/ml ; 0.000136 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.27
Solubility :	0.0898 mg/ml ; 0.000537 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P332+P313-P337+P313-P340-P362-P363-P403-P403+P233-P405-P501	UN#:	2922
Hazard Statements:	H301-H312-H314-H315-H319-H332-H335	Packing Group:	Ⅲ
GHS Pictogram:

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