[ CAS No. 185739-14-4 ]

Name: 185739-14-4|2,2-Difluoroethenyl 4-methylbenzene-1-sulfonate|95%
Brand: Ambeed
SKU: A1079670
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 185739-14-4 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 185739-14-4 ]

Product Details of [ 185739-14-4 ]

CAS No. :	185739-14-4	MDL No. :	MFCD27946567
Formula :	C₉H₈F₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZQLLPWMNXQYESO-UHFFFAOYSA-N
M.W :	234.22	Pubchem ID :	10977366
Synonyms :

Safety of [ 185739-14-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501	UN#:	1760
Hazard Statements:	H302-H315-H318-H332-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 185739-14-4 ]

* 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.

Downstream synthetic route of [ 185739-14-4 ]

[ 185739-14-4 ] Synthesis Path-Downstream 1~63

1
[ 433-06-7 ]
[ 185739-14-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -65℃; for 0.5h;	To a 3-necked flask with a stir bar (oven dried), water-cooled condenser, and internal thermometer was added 2,2,2-trifluoroethyl-4-methylbenzenesulfonate (25.4 g, 100 mmol) followed by THF (333 mL, 0.3 M). The mixture was stirred and cooled in an acetone/dry-ice bath (internal temperature at -78 C.). nBuLi (10 M in hexanes, 20 mL, 200 mmol) was added via a syringe over 10 min with internal temperature at about -65 C. The reaction mixture turned to a dark color and was stirred at -78 C. for 20 min. A mixture of water (50 mL) and THF (50 mL) was added dropwise via an addition funnel to quench the reaction (maintained internal temperature at about -70 C.). The mixture was warmed to ambient temperature and ethyl acetate (400 mL) was added. The organic layer was separated and the aqueous layer extracted with ethyl acetate (2×80 mL). The combined organics were washed with brine (50 mL), dried over Na2SO4 and evaporated to give a dark oil (29.3 g) that was purified on silica (220 g column, 60 mL/min) with gradients from 100% heptane to 40% ethyl acetate-60% heptane to give the title product as a colorless oil (22.73 g, 97% yield). 1H NMR (400 MHz, chloroform-d) 6 ppm 7.83 (d, J=8.31 Hz, 2H) 7.39 (d, J=8.19 Hz, 2H) 6.09 (dd, J=14.31, 3.91 Hz, 1H) 2.48 (s, 3H). 19F NMR (376 MHz, chloroform-d) δ ppm -92.88--88.40 (m, 1F) -110.58--107.12 (m, 1F). The title product did not ionize in LCMS
	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 2h;	1.4. Interm F Toluene-4-sulfonic acid 2,2,2-trifluoroethyl ester (1 eq, 6.0 g) is dissolved in anhydrous THF (120 mL). The reaction is cooled down to -78C, after which n-butyllithium (2.5M in hexane, 2.3 eq, 22 mL) is carefully added. The reaction is left stirring at this temperature for 2 h, after which the mixture is diluted with water and EtOAc. Extraction with EtOAc (3 x 100 mL) is performed. The combined organics are washed with sat. brine and dried over anhydrous Na2S04. Purification of the crude through column chromatography (silica, petroleum ether/EtOAc; 95:5 to 80:20) yields the desired product.
26.9 mmol	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 0.333333h;	A solution of 2,2,2-trifluoroethyl tosylate (33.4 mmol) inanhydrous THF (111 mL), at -78 C, and n-butyllithiumsolution (11 M in hexane, 66.9 mmol) was stirred at -78 Cfor 20 mm, then quenched with a mixture of water (20 mL)and THF (20 mL) whilst maintaining internal temperature at -60 C, then warmed to RT and extracted with EtOAc. The combined organic extracts were washed with a saturated solution of brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification gave the titled compound (26.9 mmol) as a colourless oil. 1H NMR (400MHz, DMSO-d6, ): 7.86 (d, J = 8.4 Hz, 2H), 7.54 (d, J = 8.6 Hz, 2H), 6.85 (dd, J = 15.6, 3.9 Hz, 1 H), 2.45 (5, 3H).

2.4 g	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 0.666667h;Inert atmosphere;	2,2,2-trifluoroethyl p-methylbenzenesulfonate (11-1) (2.57 g, 10.0 mmol) was dissolved in tetrahydrofuran (15 mL), the reaction solution was cooled to -78C under protection of nitrogen, and n-butyllithium (2.5 M in hexane, 8 mL, 20 mmol) was slowly dropwise added. The reaction solution was stirred at -78C for 40 minutes, and water (4.5 g, 25 mmol) and tetrahydrofuran (10 mL) were slowly dropwise added. The reaction solution was slowly warmed to room temperature. The reaction was added with water (60 mL), and extracted with ethyl acetate (30 mL2). The organic phase was collected, washed with saturated sodium chloride solution (50 mL2), dried over anhydrous sodium sulfate, filtered to remove anhydrous sodium sulfate, concentrated under reduced pressure, followed by purification through column chromatography, and the target compound 2.4 g was obtained. ESI-MS (m/z): 235.1 [M + H]+.
	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 1h;	To a solution of 172.1 (25 g, 98.34 mmol, 1.0 equiv) in THF (250 mL), was added n-butyl lithium (2.5M in Hexane) (78.6 mL, 196.68 mmol, 2.0 equiv) at -78 C and stirred for 1 h. A saturated solution of ammonium chloride was added slowly to quench the reaction. The mixture was allowed to warmed to room temperature and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (CombiFlash, 3% ethyl acetate in hexane) to afford 172.2. 1H NMR (CDCl3, 400 MHz): δ 7.84-7.82 (d, J= 8 Hz, 2H), 7.41-7.39 (d, J = 8 Hz, 2H), 6.11-6.07 (m, 1H), 2.49 (s, 3H).

Reference： [1]Patent: US2015/141402,2015,A1 .Location in patent: Paragraph 0730; 0731
[2]Journal of Organic Chemistry,2015,vol. 80,p. 7266 - 7274
[3]Journal of Organic Chemistry,2008,vol. 73,p. 3404 - 3410
[4]Journal of labelled compounds and radiopharmaceuticals,2013,vol. 56,p. 447 - 450
[5]Synthesis,2002,p. 1917 - 1936
[6]Journal of the American Chemical Society,2017,vol. 139,p. 3537 - 3545
[7]Chemical Communications,2017,vol. 53,p. 5665 - 5668
[8]Tetrahedron Letters,1996,vol. 37,p. 8799 - 8802
[9]Chemical Communications,2016,vol. 52,p. 1238 - 1241
[10]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3367 - 3371
[11]Organic Letters,2011,vol. 13,p. 560 - 563
[12]Chemical Communications,2011,vol. 47,p. 11873 - 11875
[13]Organic and biomolecular chemistry,2012,vol. 10,p. 6980 - 6986,7
[14]Patent: WO2017/12647,2017,A1 .Location in patent: Paragraph 0236
[15]Patent: WO2017/103611,2017,A1 .Location in patent: Paragraph 00405
[16]Patent: EP3508483,2019,A1 .Location in patent: Paragraph 0139; 0140
[17]Chinese Journal of Chemistry,2019,vol. 37,p. 1036 - 1040
[18]Organic Letters,2020,vol. 22,p. 5229 - 5234
[19]Patent: WO2021/226261,2021,A1 .Location in patent: Paragraph 0922; 0923

2
[ 185739-14-4 ]
sodium 1,1-difluoro-2-tosyloxyethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium hydrogensulfite; dibenzoyl peroxide In methanol; water at 80℃; for 40h;	9 9.3 g of 2,2-difluoroethenyl tosylate, which had been synthesised by a conventional technique, was dispersed in 17 g of water and 37 g of methanol, after which 4.7 g of sodium hydrogen sulfite and 0.5 g of benzoyl peroxide were added. The reaction mixture was stirred at 80°C for 40 hours. The reaction solution was allowed to cool, after which methanol was distilled off in vacuum. Toluene was added, followed by separatory operation to separate a water layer. A saturated sodium chloride aqueous solution was added to the water layer whereupon white crystals settled out. The crystals were collected by filtration, washed with a small volume of saturated sodium chloride aqueous solution and then dried in vacuum, obtaining the target compound, sodium 1,1-difluoro-2-tosyloxyethanesulfonate. White crystals, 2.5 g (yield 16%). The target compound was analyzed by spectroscopy. The NMR spectra, 1H-NMR (300 MHz in D2O) and 19F-NMR (282 MHz in D2O (shift standard CF3CO2D)) are shown in FIGS. 1 and 2. Infrared absorption spectra (IR, KBr, cm-1) 3041, 2994, 1598, 1452, 1363, 1307, 1292, 1280, 1238, 1213, 1197, 1182, 1130, 1112, 1105, 1022, 973, 939, 842, 809, 759, 649

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - EP1780198, 2007, A1 Location in patent: Page 33

3
[ 905966-40-7 ]
[ 185739-14-4 ]
[ 1022094-52-5 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 3404 - 3410

4
[ 1022094-44-5 ]
[ 185739-14-4 ]
[ 1022094-53-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 19h;

Reference： [1]Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410]

5
[ 5122-94-1 ]
[ 185739-14-4 ]
[ 1022094-45-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 70℃; for 22h;

Reference： [1]Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410]

6
[ 126747-14-6 ]
[ 185739-14-4 ]
[ 38936-00-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 18h;

Reference： [1]Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410]

7
[ 185739-14-4 ]
[ 149104-90-5 ]
1-(4-(2,2-difluorovinyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 18h;

Reference： [1]Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410]

8
[ 185739-14-4 ]
[ 171364-85-5 ]
[ 1022094-54-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 18h; Inert atmosphere; Sealed tube;
69%	With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 19h;

Reference： [1]McAlpine, Indrawan; Tran-Dubé, Michelle; Wang, Fen; Scales, Stephanie; Matthews, Jean; Collins, Michael R.; Nair, Sajiv K.; Nguyen, Mary; Bian, Jianwei; Alsina, Luis Martinez; Sun, Jianmin; Zhong, Jiaying; Warmus, Joseph S.; O'Neill, Brian T. [Journal of Organic Chemistry, 2015, vol. 80, # 14, p. 7266 - 7274]
[2]Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410]

9
[ 185739-14-4 ]
[ 627906-96-1 ]
[ 131581-40-3 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 3404 - 3410

10
[ 185739-14-4 ]
5,5-dimethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborinane [ No CAS ]
[ 220676-10-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 70℃; for 22h;

Reference： [1]Gogsig, Thomas M.; Sobjerg, Lina S.; Lindhardt, Anders T.; Jensen, Kim L.; Skrydstrup, Troels [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3404 - 3410]

11
[ 445264-61-9 ]
[ 185739-14-4 ]
[ 1022094-53-6 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 7266 - 7274

12
[ 1052686-60-8 ]
[ 185739-14-4 ]
5-(2,2-difluorovinyl)-2-methoxypyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 7266 - 7274

13
[ 185739-14-4 ]
[ 166330-03-6 ]
C₁₆H₂₁BF₂O₅S [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2016,vol. 34,p. 477 - 480
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3367 - 3371

14
[ 871-91-0 ]
[ 185739-14-4 ]
10,10-difluorodec-9-en-7-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

Reference： [1]Fujino, Takumi; Hinoue, Tomoaki; Usuki, Yoshinosuke; Satoh, Tetsuya [Organic Letters, 2016, vol. 18, # 21, p. 5688 - 5691]

15
[ 32870-98-7 ]
[ 185739-14-4 ]
9-(4,4-difluorobut-3-en-1-yn-1-yl)phenanthrene [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5688 - 5691

16
[ 1315350-04-9 ]
[ 185739-14-4 ]
4-amino-3-(2,2-difluorovinyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 60℃; for 1h; Inert atmosphere;	1.5.2.ii Step ii): 4-Amino-3-(2,2-difluorovinyl)benzonitrile Step ii): 4-Amino-3-(2,2-difluorovinyl)benzonitrile 4-Amino-3-(4,4,5,5-tetramethyl[l,3,2]dioxaborolan-2-yl)benzonitrile (1 eq, 30.7 mmol) and toluene-4-sulfonic acid 2,2-difluorovinyl ester (1 eq, 7.2 g) are dissolved in a 4: 1 solution of dioxane and water (175 mL). Pd(dba)3 (0.05 eq, 1.4 g), HBF4PCy3 (0.1 eq, 1.1 g) and potassium phosphate (3 eq, 19.6 g) are added, after which the suspension is degassed under nitrogen atmosphere for 10 min and the reaction is brought to 60°C for 1 h. The suspension is then filtered over a Celite pad and concentrated in vacuo. The residue is dissolved in EtOAc and an aq. extraction with sat. NaHCOs and EtOAc (3 x 150 mL) is performed. The combined organics are washed with sat. brine, dried over Na2S04 and concentrated. Purification of the crude through column chromatography (silica, petroleum ether/EtOAc; 95:5 to 90: 10) yields the desired product.

Reference： [1]Current Patent Assignee: GALAPAGOS - WO2017/12647, 2017, A1 Location in patent: Paragraph 0238

17
(2R)-8-fluoro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one [ No CAS ]
[ 185739-14-4 ]
(2R)-6-(2,2-difluoroethenyl)-8-fluoro-2-methyl-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: (2R)-8-fluoro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one; toluene-4-sulfonic acid 2,2-difluorovinyl ester With potassium phosphate In 1,4-dioxane for 0.166667h; Inert atmosphere; Sonication; Stage #2: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 105℃; for 4h; Inert atmosphere; Sealed tube;	179 (2i? -6-(2,2-Difluoroethenvn-8-fluoro-2-methyl-4 (l,3.5-trimethyl-lH-pyrazol-4-yl - methyl]-3,4-dihydro-2H-l,4-benzoxazin-3-one An aqueous solution of tripotassium phosphate (1.27M, 1.43 mL) was added to a solution of 2,2-difluoroethenyl 4-methylbenzene-l -sulfonate (prepared according to the procedure described in J. Org. Chem., 2008, 73, 3404) (250 mg, 1.07 mmol) and Intermediate 150 (76%, 603 mg, 1.07 mmol) in 1,4-dioxane (7 mL). The mixture was degassed with a stream of bubbling nitrogen whilst being sonicated for 10 minutes. Tris(dibenzylidineacetone)dipalladium(0) (24.44 mg, 0.03 mmol) and tricyclohexyl- phosphonium tetrafluoroborate (19.65 mg, 0.05 mmol) were added under nitrogen and the mixture was heated, whilst stirring, at 105°C in a sealed tube for 4 h. The mixture was allowed to cool to r. , then partitioned between saturated aqueous Na2C03 solution (30 mL) and EtOAc (30 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with brine (20 mL), dried over MgS04, filtered and concentrated in vacuo. Purification of the crude residue by column chromatography, using 0-100% EtOAc in heptane, gave the title compound (322 mg, 55%). δΗ (500 MHz, DMSO-d6) 6.98 (dd, J 11.4, 1.7 Hz, IH), 6.87 (s, IH), 5.72 (dd, J27.3, 3.9 Hz, IH), 5.08 (d, J 15.9 Hz, IH), 4.90 (q, J6.7 Hz, IH), 4.84 (d, J 15.8 Hz, IH), 3.57 (s, 3H), 2.17 (s, 3H), 1.96 (s, 3H), 1.50 (d, J 6.7 Hz, 3H).Method B HPLC-MS: MH+ mlz 366.1, RT 2.01 minutes (100%).

Reference： [1]Current Patent Assignee: UCB - WO2016/198400, 2016, A1 Location in patent: Page/Page column 104; 105

18
[ 6971-74-0 ]
[ 185739-14-4 ]
(E)-(3-oxo-2-tosylisoindolin-1-ylidene)methyl 4-methylbenzenesulfonate [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5665 - 5668

19
[ 6971-74-0 ]
[ 185739-14-4 ]
C₂₃H₂₀FNO₆S₂ [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5665 - 5668

20
[ 101251-09-6 ]
[ 185739-14-4 ]
N-(4-(2,2-difluorovinyl)phenyl)acteamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 12855 - 12862

21
[ 6999-03-7 ]
[ 185739-14-4 ]
C₁₁H₁₄F₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

22
1-bromo-4-(trans-4-n-propylcycohexyl)benzene [ No CAS ]
[ 185739-14-4 ]
C₁₇H₂₂F₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

23
[ 51554-95-1 ]
[ 185739-14-4 ]
C₁₃H₁₆F₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

24
[ 6343-72-2 ]
[ 185739-14-4 ]
C₁₄H₁₀F₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

25
[ 66107-30-0 ]
[ 185739-14-4 ]
4-(2,2-difluorovinyl)phenyl trifluoromethanesulfonate [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 13616 - 13623

26
[ 6324-15-8 ]
[ 185739-14-4 ]
4-(2,2-difluorovinyl)phenyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

27
[ 619-42-1 ]
[ 185739-14-4 ]
[ 1022094-52-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

28
[ 148547-19-7 ]
[ 185739-14-4 ]
C₁₁H₁₀F₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 100℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

29
[ 33626-98-1 ]
[ 185739-14-4 ]
C₁₄H₁₀F₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

30
[ 580-13-2 ]
[ 185739-14-4 ]
[ 131581-40-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

31
[ 90-90-4 ]
[ 185739-14-4 ]
C₁₅H₁₀F₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

32
[ 3466-32-8 ]
[ 185739-14-4 ]
1-(2,2-difluorovinyl)-4-(methylsulfonyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

33
[ 1127562-54-2 ]
[ 185739-14-4 ]
C₁₇H₁₁F₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

34
[ 4923-87-9 ]
[ 185739-14-4 ]
C₁₀H₆F₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

35
[ 92-66-0 ]
[ 185739-14-4 ]
[ 1022094-45-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

36
[ 86-76-0 ]
[ 185739-14-4 ]
2-(2,2-difluorovinyl)dibenzo[b,d]furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

37
[ 63996-36-1 ]
[ 185739-14-4 ]
2-(4-(2,2-difluorovinyl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

38
[ 92-86-4 ]
[ 185739-14-4 ]
4,4'-bis-(2,2-difluorovinyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

39
[ 179866-74-1 ]
[ 185739-14-4 ]
C₂₈H₂₂F₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

40
[ 866769-99-5 ]
[ 185739-14-4 ]
C₃₄H₂₆F₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

41
C₃₄H₅₁BrO₂ [ No CAS ]
[ 185739-14-4 ]
C₃₆H₅₂F₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

42
[ 2113-57-7 ]
[ 185739-14-4 ]
3-(2,2-difluorovinyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

43
C₁₉H₂₃BrO₇ [ No CAS ]
[ 185739-14-4 ]
C₂₁H₂₄F₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

44
[ 185739-14-4 ]
[ 2925-16-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: (2,2-difluoroethenyl) 4-methylbenzenesulfonate With [2,2]bipyridinyl; nickel (II) chloride; zinc In N,N-dimethyl acetamide at 60℃; for 8h; Stage #2: With iodine for 0.333333h;
51%	Stage #1: (2,2-difluoroethenyl) 4-methylbenzenesulfonate With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; nickel(II) bromide; zinc In N,N-dimethyl acetamide at 60℃; for 4h; Sealed tube; Stage #2: With iodine; lithium chloride In tetrahydrofuran at 20℃; for 0.333333h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]
[2]Chen, Gang; Chen, Lei; Dong, Lin; He, Xiaochun; Lian, Zhong; Liu, Jiangjun; Ma, Xuelei; Xiao, Xue; Xiong, Baojian; Zhang, Xuemei [Organic Letters, 2022]

45
[ 4333-76-0 ]
[ 185739-14-4 ]
C₁₆H₁₂F₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

46
[ 185739-14-4 ]
[ 4714-24-3 ]
C₁₆H₁₂F₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

47
[ 5111-65-9 ]
[ 185739-14-4 ]
[ 1022094-48-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

48
[ 101-55-3 ]
[ 185739-14-4 ]
[ 220676-10-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

49
[ 36809-26-4 ]
[ 185739-14-4 ]
[ 1501969-17-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;

Reference： [1]Xiong, Baojian; Wang, Ting; Sun, Haotian; Li, Yue; Kramer, Søren; Cheng, Gui-Juan; Lian, Zhong [ACS Catalysis, 2020, vol. 10, # 22, p. 13616 - 13623]

50
[ 17870-62-1 ]
[ 185739-14-4 ]
2-fluoro-indolizine-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 12h;	1.b.2 b) Step-2: Ethyl 2-fluoroindolizine-3-carboxylate: To a stirred solution of 1-(2-ethoxy-2-oxoethyl)pyridin-1-ium (8 g, 48.1 mmol)in N,N-dimethyl formamide (80 mL), 2,2-difluorovinyl 4-methylbenzenesulfonate (7.9 g, 33.7 mmol), potassium carbonate (6.7 g, 48.1 mmol) and triethyl amine (6.7 mL, 48.1 mmol) were added. The reaction mixture was heated at 70 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (150 mL) was added to the above reaction mixture and extracted twice with ethyl acetate (300 mL). The combined ethyl acetate layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash column chromatography on silica gel using ethyl acetate in hexane as an eluent to obtain ethyl 2- fluoroindolizine-3-carboxylate (4.2 g, 20.3 mmol, 42 % yield). 1H-NMR (400 MHz, DMSO-d6) d 9.29 (dq, J = 7.2, 1.0 Hz, 1H), 7.51-7.65 (m, 1H), 7.23-7.27 (m, 1H), 6.72-7.08 (m, 1H), 6.27-6.50 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H); ESI MS (m/z) 208.20 (MH)+

Reference： [1]Current Patent Assignee: PI INDUSTRIES LTD - WO2020/250183, 2020, A1 Location in patent: Page/Page column 88

51
methyl 4-(2,2-difluorocyclopropyl)benzoate [ No CAS ]
[ 185739-14-4 ]
C₁₃H₁₁F₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

52
methyl 3-(2,2-difluorocyclopropyl)benzoate [ No CAS ]
[ 185739-14-4 ]
C₁₃H₁₁F₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

53
C₁₅H₁₇F₂NO [ No CAS ]
[ 185739-14-4 ]
C₁₇H₁₈F₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

54
C₁₀H₁₀F₂O₂S [ No CAS ]
[ 185739-14-4 ]
C₁₂H₁₁F₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

55
2-(2,2-difluorocyclopropyl)naphthalene [ No CAS ]
[ 185739-14-4 ]
C₁₅H₁₁F₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

56
2-(4-(2,2-difluorocyclopropyl)phenyl)pyridine [ No CAS ]
[ 185739-14-4 ]
C₁₆H₁₂F₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

57
(8R,9S,13S,14S)-3-(2,2-difluorocyclopropyl)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one [ No CAS ]
[ 185739-14-4 ]
C₂₃H₂₅F₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

58
C₂₀H₂₆F₂O₂ [ No CAS ]
[ 185739-14-4 ]
C₂₂H₂₇F₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

59
C₂₂H₂₈F₂O₆ [ No CAS ]
[ 185739-14-4 ]
C₂₄H₂₉F₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

60
C₁₄H₁₆F₂O₂ [ No CAS ]
[ 185739-14-4 ]
C₁₆H₁₇F₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

61
[ 1323437-13-3 ]
[ 185739-14-4 ]
C₁₇H₁₃F₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

62
C₁₆H₁₄F₂O₃S [ No CAS ]
[ 185739-14-4 ]
C₁₈H₁₅F₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

63
[ 1241957-35-6 ]
[ 185739-14-4 ]
C₁₅H₁₇F₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With nickel(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate); 2,2'-biquinoline; palladium diacetate; zinc; XPhos In N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; stereoselective reaction;

Reference： [1]Xiong, Baojian; Chen, Xuemeng; Liu, Jiangjun; Zhang, Xuemei; Xia, Ying; Lian, Zhong [ACS Catalysis, 2021, vol. 11, # 19, p. 11960 - 11965]

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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

[ CAS No. 185739-14-4 ]

Quality Control of [ 185739-14-4 ]

Related Doc. of [ 185739-14-4 ]

Product Details of [ 185739-14-4 ]

Safety of [ 185739-14-4 ]

Application In Synthesis of [ 185739-14-4 ]

[ 185739-14-4 ] Synthesis Path-Downstream 1~63

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry