[ CAS No. 1647073-46-8 ] {[proInfo.proName]}

Name: 1647073-46-8|N-(Trifluoromethylthio)saccharin|98%
Brand: Ambeed
SKU: A965098
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CAS No. :	1647073-46-8	MDL No. :	MFCD28127153
Formula :	C₈H₄F₃NO₃S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNDYXRJLEZMPBC-UHFFFAOYSA-N
M.W :	283.25	Pubchem ID :	99771197
Synonyms :

Safety of [ 1647073-46-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	1759
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1647073-46-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1647073-46-8 ]

[ 1647073-46-8 ] Synthesis Path-Downstream 1~15

1
[ 120-72-9 ]
[ 1647073-46-8 ]
[ 62665-49-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With chloro-trimethyl-silane In dichloromethane at 20℃; for 0.5h; Schlenk technique;
93%	With iron(III) chloride In 1,2-dichloro-ethane at 50℃; for 12h; Inert atmosphere; Sealed tube;
88%	In 2,2,2-trifluoroethanol at 40℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;	General procedure for reaction of N-trifluoroemthylthiosaccharin with arene inTFE General procedure: Arene (0.500 mmol), N-trifluoroemthylthiosaccharin (215 mg, 0.750 mmol), CF3CH2OH (1.5 mL) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an atmosphere of argon. The tube was quickly sealed with a rubber stopper. The reaction was stirred at 40 °C for 12 h. The mixture was concentrated under vacuum. The residue was purified by flash column chromatography to give the desired product.

	With sodium chloride In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere; Sealed tube;
100 %Spectr.	In acetonitrile at 20℃; for 3h;

Reference： [1]Xu, Chunfa; Ma, Bingqing; Shen, Qilong [Angewandte Chemie - International Edition, 2014, vol. 53, # 35, p. 9316 - 9320,5][Angew. Chem., 2014, vol. 126, # 35, p. 9470 - 9474,5][Angewandte Chemie, 2014, vol. 126, # 35, p. 9470 - 9474,5]
[2]Wang, Qiang; Qi, Zisong; Xie, Fang; Li, Xingwei [Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 355 - 360]
[3]Lu, Shiyao; Chen, Wenbo; Shen, Qilong [Chinese Chemical Letters, 2019, vol. 30, # 12, p. 2279 - 2281]
[4]Kovács, Szabolcs; Bayarmagnai, Bilguun; Goossen, Lukas J. [Advanced Synthesis and Catalysis, 2017, vol. 359, # 2, p. 250 - 254]
[5]Zhang, Jingjing; Yang, Jin-Dong; Zheng, Hanliang; Xue, Xiao-Song; Mayr, Herbert; Cheng, Jin-Pei [Angewandte Chemie - International Edition, 2018, vol. 57, # 39, p. 12690 - 12695][Angew. Chem., 2018, vol. 130, # 39, p. 12872 - 12877,6]

2
2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
[ 151-10-0 ]
[ 66476-29-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With methanesulfonic acid In acetonitrile at 60℃; for 8h; Green chemistry;	8 Example 8: Preparation of 1,3-dimethoxy-4-trifluoromethylthiobenzene General procedure: The present invention screens the preparation of 1,3-dimethoxy-4-trifluoromethylthiobenzene as shown in Table 1.Among them, the data results show that in the preparation method of 1,3-dimethoxy-4-trifluoromethylthiobenzene, when the temperature is high, the yield of the reaction is high. _: 1,3-Dimethoxybenzene (42 mg, 0.3 mmol), nitrogen-trifluoromethylthiosaccharide (94 mg, 0.33 mmol) was added to a 25 mL reaction flask.Trifluoromethanesulfonic acid (24 μL, 0.3 mmol) and dichloromethane (6 mL) were reacted at room temperature for 4 hr.After the reaction was completed, the solvent was removed by rotary evaporation under reduced pressure.The residue was purified by flash silica gel to give the product62 mg, yield 86%.
92%	With iron(III) chloride; silver hexafluoroantimonate In 1,2-dichloro-ethane at 100℃; for 16h; Inert atmosphere; Sealed tube;
87%	In 2,2,2-trifluoroethanol at 40℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;	General procedure for reaction of N-trifluoroemthylthiosaccharin with arene inTFE General procedure: Arene (0.500 mmol), N-trifluoroemthylthiosaccharin (215 mg, 0.750 mmol), CF3CH2OH (1.5 mL) were placed into an oven-dried Schlenk tube that was equipped with a stirring bar under an atmosphere of argon. The tube was quickly sealed with a rubber stopper. The reaction was stirred at 40 °C for 12 h. The mixture was concentrated under vacuum. The residue was purified by flash column chromatography to give the desired product.

86%	With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 4h; Schlenk technique;
97.7 mg	With trifluorormethanesulfonic acid In dichloromethane

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104945304, 2018, B Location in patent: Paragraph 0081; 0082; 0083; 0084; 0085; 0086; 0087
[2]Wang, Qiang; Qi, Zisong; Xie, Fang; Li, Xingwei [Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 355 - 360]
[3]Lu, Shiyao; Chen, Wenbo; Shen, Qilong [Chinese Chemical Letters, 2019, vol. 30, # 12, p. 2279 - 2281]
[4]Xu, Chunfa; Ma, Bingqing; Shen, Qilong [Angewandte Chemie - International Edition, 2014, vol. 53, # 35, p. 9316 - 9320,5][Angew. Chem., 2014, vol. 126, # 35, p. 9470 - 9474,5][Angewandte Chemie, 2014, vol. 126, # 35, p. 9470 - 9474,5]
[5]Kovács, Szabolcs; Bayarmagnai, Bilguun; Goossen, Lukas J. [Advanced Synthesis and Catalysis, 2017, vol. 359, # 2, p. 250 - 254]

3
[ 14070-51-0 ]
[ 811-68-7 ]
2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In acetonitrile; at 20℃; for 0.166667h;	Saccharin (6.0 g) was reacted in methanol (120 ml) at room temperature for 5 minutes with tert-butyl hypochlorite (5 ml) to give the compoundChloro-saccharin 1a (6.0 g, 84%); Chloro-saccharin 1a (3.0 g) was reacted with trifluoromethylthio-silver (3.6 g) in acetonitrile (40 ml) at room temperature for 10 min to give Compound 1 (3.3 g, 86%). Reagent 1 is a white solid at room temperature, soluble in organic solvents such as dichloromethane, chloroform, acetone and acetonitrile.
86%	In acetonitrile; at 20℃; for 0.166667h;	Saccharin (6.0 g of) in methanol (120ml) at room temperature and tert-butyl hypochlorite (5ml) for 5 minutes to give saccharin chloro compound 1a (6.0g, 84%); chloro saccharin 1a (3.0g) and three difluoromethylthio-silver (3.6 g of) in acetonitrile (40ml) and reacted at room temperature for 10 minutes to give compound 1 (3.3g, 86%).Reagent 1 at room temperature a white solid was soluble in methylene chloride, chloroform, acetone, and acetonitrile.N - trifluoromethylthio-saccharin (2 - ((Trifluoromethyl) Thio) of benzo [D] isothiazol-3 (2H) -one1,1-dioxide)
86%	In acetonitrile; at 20℃; for 0.166667h;	Saccharin (6.0 g of) in methanol (120ml) and tert-butyl hypochlorite (5ml) for 5 minutes to give saccharin chloro compound 1a (6.0g, 84%) at room temperature; chloro saccharin 1a (3.0g) and three difluoromethylthio-silver (3.6 g of) the reaction at room temperature in acetonitrile (40ml) 10 minutes to give compound 1 (3.3g, 86%).

86%	In acetonitrile; at 20℃; for 0.166667h;Green chemistry;	Saccharin (6.0 g) was reacted with t-butyl hypochlorite (5 ml) in methanol (120 ml) for 5 minutes at room temperature to give the compound chlorosaccharide 1a (6.0 g, 84%);The chloro saccharin 1a (3.0 g) was reacted with trifluoromethylthio silver (3.6 g) in acetonitrile (40 ml) at room temperature for 10 minutes to give compound II (3.3 g, 86%).The compound II is a white solid at room temperature and is soluble in an organic solvent such as dichloromethane, chloroform, acetone or acetonitrile.
77%	In acetonitrile; at 20℃; for 0.166667h;Inert atmosphere;	<strong>[14070-51-0]N-chlorosaccharin</strong> (1 eq, 1.15 mmol, 250 mg) and AgSCF3 (1.2 eq,1.38 mmol, 288 mg) were dissolved in CH3CN (4 mL) under N2 atmosphere.The mixture was stirred vigorously at room temperature for 10 min. The CH3CN was then drained under reduced pressure. And the residue was extracted with CH2Cl2 (3 mL× 3). The solution wa scombined and the solvent was evaporated under vacuum. The residue was further dried under high vacuum to give compound 2b as a white solid. Yield 251 mg, 77%. 1H NMR (300 MHz, CDCl3): 8.20 (d, 1HJ = 7.5 Hz), 8.08-7.99 (m, 2H), 7.98-7.91 (m, 1H). 19F-NMR (CDCl3): delta -47.73 (s, 3F) ppm. 13C NMR (CDCl3): 158.4,137.9, 136.4, 135.0, 127.8 (q, J = 315 Hz), 126.5, 126.1, 122.0 ppm.

Reference： [1]Patent: CN104945294,2016,B .Location in patent: Paragraph 0135; 0136; 0137; 0138
[2]Patent: CN104945298,2016,B .Location in patent: Paragraph 0187; 0188; 0189; 0190
[3]Patent: CN104945348,2017,B .Location in patent: Paragraph 0085-0087
[4]Patent: CN104945304,2018,B .Location in patent: Paragraph 0109; 0110; 0111
[5]Angewandte Chemie - International Edition,2014,vol. 53,p. 9316 - 9320,5
    Angew. Chem.,2014,vol. 126,p. 9470 - 9474,5
    Angewandte Chemie,2014,vol. 126,p. 9470 - 9474,5
[6]Angewandte Chemie - International Edition,2018,vol. 57,p. 12690 - 12695
    Angew. Chem.,2018,vol. 130,p. 12872 - 12877,6
[7]Catalysis Today,2018,vol. 308,p. 94 - 101

4
[ 617-94-7 ]
[ 1647073-46-8 ]
[ 1640084-14-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In dichloromethane at 20℃; for 0.0833333h;
87%	With triethylamine In dichloromethane at 20℃; for 0.0833333h;	18 Example 18 50mL egg-shaped flask was added N - saccharin trifluoromethylthio group 1 (184mg, 0.65mmol), 2- methyl-2-phenylethanol (69.0mg, 0.5mmol), 160μL (1.15mmol) of triethylamine, dichlorobis methane (10 mL), at room temperature for 5min.After completion of the reaction, the reaction solution rapidly by about 6 millimeters silica gel column, the column with the amount of methylene chloride and washed twice, and the combined organic liquid, spin dry to give trifluoromethyl - (2-phenyl) isopropyl thio peroxide (103mg, 87% isolated yield).Purity by NMR identified more than 95%.Trifluoromethyl - (2-phenyl) peroxy isopropyl-thio (((2-phenylpropan-2-YL) Oxy) (trifluoromethyl) sulfane):
80%	With triethylamine In dichloromethane at 20℃; for 0.0833333h;

Reference： [1]Xu, Chunfa; Ma, Bingqing; Shen, Qilong [Angewandte Chemie - International Edition, 2014, vol. 53, # 35, p. 9316 - 9320,5][Angew. Chem., 2014, vol. 126, # 35, p. 9470 - 9474,5][Angewandte Chemie, 2014, vol. 126, # 35, p. 9470 - 9474,5]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104945298, 2016, B Location in patent: Paragraph 0132; 0133; 0134; 0135
[3]Shao, Xinxin; Xu, Chunfa; Lu, Long; Shen, Qilong [Journal of Organic Chemistry, 2015, vol. 80, # 6, p. 3012 - 3021]

5
2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
[ 26171-23-3 ]
3-trifluoromethylthiotolemtin [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3211 - 3214

6
[ 1647073-46-8 ]
[ 100-52-7 ]
[ 175400-81-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium decatungstate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;	7 Synthesis of S-(trifluoromethyl) thiobenzoate (3a) In a dry 10 mL screw cap tube equipped with a magnetic stir bar, add 2b (0.2 mmol), NaDT (2 mol %),Aldehyde (0.30 mmol) followed by dry acetonitrile (2 mL) under nitrogen. The reaction mixture was allowed to stir at room temperature for 12 hours under illumination from a 40W LED.Et2O (30 mL) was then added, the resulting mixture was washed with water (3 x 30 mL), and the organic layer was dried over MgSO4.The solvent was removed by rotary evaporation in an ice bath and the resulting product was purified by flash chromatography on silica gel.The synthesis was carried out according to the general synthetic method using formaldehyde (0.3 mmol) and the crude product was purified by flash chromatography,Using petroleum ether (Rf=0.6) as eluent, the title compound 3a (42 mg) was obtained in 99%.
99%	With sodium decatungstate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;	7 Synthesis of S-(trifluoromethyl) thiobenzoate (3a) In a dry 10 mL screw cap tube equipped with a magnetic stir bar, add 2b (0.2 mmol), NaDT (2 mol %),Aldehyde (0.30 mmol) followed by dry acetonitrile (2 mL) under nitrogen. The reaction mixture was allowed to stir at room temperature for 12 hours under illumination from a 40W LED.Et2O (30 mL) was then added, the resulting mixture was washed with water (3 x 30 mL), and the organic layer was dried over MgSO4.The solvent was removed by rotary evaporation in an ice bath and the resulting product was purified by flash chromatography on silica gel.The synthesis was carried out according to the general synthetic method using formaldehyde (0.3 mmol) and the crude product was purified by flash chromatography,Using petroleum ether (Rf=0.6) as eluent, the title compound 3a (42 mg) was obtained in 99%.
80%	With sodium decatungstate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

65 %Spectr.

With benzoic acid sodium salt; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In acetonitrile at 20℃; Inert atmosphere; Irradiation;

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN113860981, 2021, A Location in patent: Paragraph 0065-0069
[2]Current Patent Assignee: SHANDONG UNIVERSITY - CN113860981, 2021, A Location in patent: Paragraph 0065-0069
[3]Ye, Zhegao; Lei, Ziran; Ye, Xiaodong; Zhou, Liejin; Wang, Yanan; Yuan, Zheliang; Gao, Feng; Britton, Robert [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 765 - 775]
[4]Mukherjee, Satobhisha; Patra, Tuhin; Glorius, Frank [ACS Catalysis, 2018, vol. 8, # 7, p. 5842 - 5846]

7
[ 1647073-46-8 ]
[ CAS Unavailable ]
[ 1927969-10-5 ]

Yield	Reaction Conditions	Operation in experiment
51 %Spectr.	With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Mao, Runze; Bera, Srikrishna; Cheseaux, Alexis; Hu, Xile [Chemical Science, 2019, vol. 10, # 41, p. 9555 - 9559]

8
[ 1647073-46-8 ]
[ CAS Unavailable ]
[ 1927969-10-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium decatungstate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Ye, Zhegao; Lei, Ziran; Ye, Xiaodong; Zhou, Liejin; Wang, Yanan; Yuan, Zheliang; Gao, Feng; Britton, Robert [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 765 - 775]

9
[ CAS Unavailable ]
[ 1647073-46-8 ]
[ CAS Unavailable ]
[ 1927969-10-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium decatungstate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Ye, Zhegao; Lei, Ziran; Ye, Xiaodong; Zhou, Liejin; Wang, Yanan; Yuan, Zheliang; Gao, Feng; Britton, Robert [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 765 - 775]

10
[ 530-48-3 ]
[ 1647073-46-8 ]
[ CAS Unavailable ]
[ 1927969-10-5 ]
[ 117252-14-9 ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium decatungstate In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Ye, Zhegao; Lei, Ziran; Ye, Xiaodong; Zhou, Liejin; Wang, Yanan; Yuan, Zheliang; Gao, Feng; Britton, Robert [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 765 - 775]

11
[ 1647073-46-8 ]
[ 202409-33-4 ]
[ 2815251-85-3 ]