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[ CAS No. 330-17-6 ]

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Chemical Structure| 330-17-6

Chemical Structure| 330-17-6

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Quality Control of [ 330-17-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 330-17-6 ]

Product Details of [ 330-17-6 ]

CAS No. :	330-17-6	MDL No. :	MFCD00040906
Formula :	C₈H₅F₃O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UMOGQQWVQUQTQA-UHFFFAOYSA-N
M.W :	222.18	Pubchem ID :	2777858
Synonyms :

Calculated chemistry of [ 330-17-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.31
TPSA :	62.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	3.95
Log Po/w (WLOGP) :	4.26
Log Po/w (MLOGP) :	2.67
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	2.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-3.83
Solubility :	0.0332 mg/ml ; 0.00015 mol/l
Class :	Soluble
Log S (Ali) :	-4.96
Solubility :	0.00241 mg/ml ; 0.0000108 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.78
Solubility :	0.372 mg/ml ; 0.00167 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.42

Safety of [ 330-17-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 330-17-6 ]

* 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 [ 330-17-6 ]

[ 330-17-6 ] Synthesis Path-Downstream 1~68

1
[ 332-26-3 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride at 140℃;

Reference： [1]Jagupolssky; Marenez [Zhurnal Obshchei Khimii, 1954, vol. 24, p. 887][J. Gen. Chem. USSR (Engl. Transl.), 1954, vol. 24, p. 885,886]

2
[ 352-68-1 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	(i) Br₂, (irradiation), CCl₄, (ii) aq. HNO₃; Multistep reaction;

Reference： [1]Sheppard,W.A. [Journal of Organic Chemistry, 1964, vol. 29, p. 895 - 898]

3
[ 330-17-6 ]
[ 74483-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	(i) LiAlH₄, (ii) SOCl₂; Multistep reaction;

Reference： [1]Kaiser; Leonard; Heil; Lester; Tedeschi; Zirkle [Journal of medicinal chemistry, 1970, vol. 13, # 5, p. 820 - 826]

4
[ 330-17-6 ]
[ 79865-54-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With dihydrogen peroxide; dicyclohexyl-carbodiimide In diethyl ether; dichloromethane at 0 - 2℃;

Reference： [1]Rakhimov, A. I.; Androsyuk, E. R.; Shelyazhenko, S. V.; Yagupol'skii, L. M. [Journal of Organic Chemistry USSR (English Translation), 1981, p. 1470 - 1475][Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 8, p. 1652 - 1657]

5
[ 88489-60-5 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogenchloride In acetic acid at 110℃; for 6h;

Reference： [1]Kondratenko, N. V.; Kolomeitsev, A. A.; Popov, V. I.; Il'chenko, A. Ya.; Korzhenevskaya, N. G.; et al. [Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2254 - 2258][Zhurnal Obshchei Khimii, 1983, vol. 53, # 11, p. 2500 - 2505]

6
[ 330-17-6 ]
[ 17128-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

Yield	Reaction Conditions	Operation in experiment
	4-Fluormercaptocarbonyl-benzoesaeure, SF4, Autoklav, 150grad-175grad;
	p-Trichlormethylmercaptobenzoesaeurechlorid, 1) SbF3, Δ, 2) W., Acn., Δ;

8
[ 6302-65-4 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / liquid ammonia / 0.5 h / Irradiation; PRK-4 mercury lamp 2: 94 percent / HCl / acetic acid / 6 h / 110 °C

Reference： [1]Kondratenko, N. V.; Kolomeitsev, A. A.; Popov, V. I.; Il'chenko, A. Ya.; Korzhenevskaya, N. G.; et al. [Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2254 - 2258][Zhurnal Obshchei Khimii, 1983, vol. 53, # 11, p. 2500 - 2505]

9
[ 330-17-6 ]
[ 384-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH 3: SO₃/H₂SO₄, NaN₃ 4: (i) H₂SO₄, NaNO₂, (ii) aq. Na₂S₂O₄, H₂SO₄

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

10
[ 330-17-6 ]
[ 1948-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

11
[ 330-17-6 ]
[ 17095-16-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH 3: SO₃/H₂SO₄, NaN₃

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

12
[ 330-17-6 ]
[ 17095-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH 3: SO₃/H₂SO₄, NaN₃ 4: (i) H₂SO₄, NaNO₂, (ii) aq. Na₂S₂O₄, H₂SO₄ 5: aq. HCl, SnCl₂

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

13
[ 330-17-6 ]
[ 17128-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH 3: SO₃/H₂SO₄, NaN₃ 4: (i) H₂SO₄, NaNO₂, (ii) aq. Na₂S₂O₄, H₂SO₄ 5: aq. HCl, SnCl₂ 6: (i) NaNO₂, H₂SO₄, AcOH, (ii) /BRN= 507140/

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

14
[ 330-17-6 ]
[ 3771-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH 3: SO₃/H₂SO₄, NaN₃ 4: (i) H₂SO₄, NaNO₂, (ii) aq. Na₂S₂O₄, H₂SO₄ 5: aq. HCl, SnCl₂ 6: (i) aq. HCl, NaNO₂, (ii) /BRN= 507140/

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

15
[ 330-17-6 ]
[ 17128-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aq. HNO₃, H₂SO₄ 2: CrO₃, AcOH 3: SO₃/H₂SO₄, NaN₃ 4: (i) AcOH, H₂SO₄, NaNO₂, (ii) /BRN= 507140/

Reference： [1]Yagupol'skii,L.M.; Gandel'sman,L.Z. [Journal of general chemistry of the USSR, 1967, vol. 37, p. 1992 - 1997][Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 2101 - 2108]

16
[ 696-61-7 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran 2: (i) Br₂, (irradiation), CCl₄, (ii) aq. HNO₃

Reference： [1]Sheppard,W.A. [Journal of Organic Chemistry, 1964, vol. 29, p. 895 - 898]

17
[ 330-17-6 ]
[ 29805-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) LiAlH₄, (ii) SOCl₂ 2: (i) NaH, DMSO, (ii) /BRN= 2364099/

Reference： [1]Kaiser; Leonard; Heil; Lester; Tedeschi; Zirkle [Journal of medicinal chemistry, 1970, vol. 13, # 5, p. 820 - 826]

18
[ 330-17-6 ]
2-(2-Dimethylamino-ethyl)-2-(4-trifluoromethylsulfanyl-benzyl)-malonic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (i) LiAlH₄, (ii) SOCl₂ 2: (i) NaH, DMSO, (ii) /BRN= 2364099/ 3: (i) NaH, DMSO, (ii) /BRN= 605280/

Reference： [1]Kaiser; Leonard; Heil; Lester; Tedeschi; Zirkle [Journal of medicinal chemistry, 1970, vol. 13, # 5, p. 820 - 826]

19
[ 330-17-6 ]
[ 312-22-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium permanganate; acetic acid In water at 20℃; for 16h;	17 Example 17 (S)-N-(1-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-cyanopropan-2-yl)-4-(trifluoromethylsulfonyl)benzamide Example 17 (S')-N-('l-('7-chloro-l-hvdroxy-l,3-dihvdrobenzo[cl[l.,21oxaborol-6-yloxy')-2-cvanopropan -2-vl)-4-ftrifluoromethvlsulfonvl)benzamide To the solution of 4-(trifluoromethylthio)benzoic acid (5g, 22.5 mmol) is dissolved in water (50 mL) and acetic acid (150 mL) is added potassium permanganate (20g, 126.5 mmol) at rt. The reaction is stirred for 16 h, diluted with ethyl acetate and washed with water. The organic layer is dried over MgS04 and concentrated to give 4-(trifluoromethylsulfonyl)benzoic acid (5g, 87% yield).
86%	With oxone In methanol; water at 20 - 50℃; for 102h;	83.A To a solution of 4-trifluoromethylsulfanyl-benzoic acid (250 mg, 1.13 mmol) in methanol (10 mL) and water (8 mL) is added oxone (5.59 g, 6.75 mmol) and the reaction is stirred first at 50 °C for 6 hours, then at room temperature for 4 days. The mixture is diluted with ethyl acetate and water and the layers are separated. The aqueous layer is extracted with ethyl acetate and the combined organic phase washed with brine, dried over Na2SO4, filtered, and the solvent is removed in vacuo to afford the desired product (245 mg, 86%). LCMS: 253.00 (M-H+).
	With potassium permanganate; acetic acid In water at 20℃; for 16h;	19 Example 19 N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(trifluoromethylsulfonyl)benzamide 4-(trifluoromethylthio)benzoic acid (200 mg, 0.9 mmol) was dissolved in water (2 mL) and acetic acid (4 mL) and treated with potassium permanganate (711 mg, 4.5 mmol) at room temperature. The reaction was allowed to stir for 16 h, diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO/i) and concentrated to yield 4-(trifluoromethylsulfone)benzoic acid.

	With potassium permanganate; acetic acid In water at 20℃; for 16h;	19 4-(trifluoromethylthio)benzoic acid (200 mg, 0.9 mmol) was dissolved in water (2 mL) and acetic acid (4 mL) and treated with potassium permanganate (711 mg, 4.5 mmol) at room temperature. The reaction was allowed to stir for 16 h, diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4) and concentrated to yield 4-(trifluoromethylsulfone)benzoic acid.
500 mg	With potassium permanganate; acetic acid In water at 20℃; for 12h;	76 Synthesis of II-A-24b A mixture of KMnCL (2000 mg, 12.66 mmol) and 4- (trifluoromethylsulfanyl)benzoic acid (500 mg, 2.25 mmol) in acetic acid (15 mL) and water (5 mL) was stirred at 20 °C for 12 hours. The mixture was diluted with water (20 mL) and the aqueous layer was extracted with EtOAc (20 mL x 2). The combined organic phase was washed with water (20 mL x 2) and brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated to give the product (500 mg, 1.97 mmol) as a solid. NMR (400MHz, CD3OD) dH = 8.37 (d, 2H), 8.20 (d, 2H).

Reference： [1]Current Patent Assignee: PFIZER INC; ELI LILLY & CO - WO2014/149793, 2014, A1 Location in patent: Page/Page column 72
[2]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2010/5783, 2010, A1 Location in patent: Page/Page column 140-141
[3]Current Patent Assignee: ROCHE HOLDING AG; CURIS INC - WO2009/126863, 2009, A2 Location in patent: Page/Page column 89
[4]Current Patent Assignee: CURIS INC; ROCHE HOLDING AG - US2006/63779, 2006, A1 Location in patent: Page/Page column 75
[5]Current Patent Assignee: PRAXIS PRECISION MEDICINES INC; PRAKISS PREC DRUG - WO2020/227097, 2020, A1 Location in patent: Paragraph 000348

20
[ 330-17-6 ]
[ 128273-56-3 ]
[ 56602-33-6 ]
[ 329317-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In N,N-dimethyl-formamide	5 Example 5 Example 5 N-(4-Trifluoromethylsulfonylbenzyl)-4-trifluoromethylsulfonylbenzamide (5). A mixture of 4-(trifluoromethylthio)benzoic acid (300 mg, 1.35 mmol), 4-(trifluoromethylthio)benzylamine (308 mg, 1.49 mmol), benzotriazol-1-yl-oxytris-(dimethylamino)-phosphonium hexafluorophosphate (1.8 g, 4.05 mmol) and DMAP (198 mg, 1.62 mmol) in DMF (15 mL) was stirred at rt overnight. The reaction was diluted with ether, washed with water, dried and concentrated to give 520 mg (94%) of N-(4-trifluoromethylthiobenzyl)-4-trifluoromethylthiobenzamide as a white solid. 1H-NMR (360 MHz, DMSO-d6) δ 9.27 (m, 1H, NH), 8.01 (d, J=8.0 Hz, 2H), 7.82 (d, J=8.0 Hz, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 4.54 (d, J=5.8 Hz, 2H, NCH2). MS-EI m/z 411 [M+]. N-(4-trifloromethylthiolbenzyl)-4-trifloromethylthiobenzamide (300 mg, 0.73 mmol) was oxidized using 3-chloroperbenzoic acid (879 mg, excess) to give 310 mg (90%) of N-(4-trifluoromethylsulfonylbenzyl)-4-trifluoromethylsulfonylbenzamide. 1H-NMR (360 MHz, DMSO-d6) δ 9.61 (m, 1H, NH), 8.28 (s, 4H), 8.10 (d, J=8.5 Hz, 2H), 7.79 (d, J=8.5 Hz, 2H), 4.69 (d, J=6.1 Hz, 2H, NCH2).

Reference： [1]Current Patent Assignee: PFIZER INC - US6596772, 2003, B1

21
[ 330-17-6 ]
[ 3468-17-5 ]
[ 1178608-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With PS-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20.0℃; for 60.0h;	A suspension of 4-(trifluoromethylthio)benzoic acid (0.333 g, 1.499 mmol; Aldrich) and 1 H-indole-6-methanamine (0.146 g, 0.999 mmol; Chemgenix) in 10: 1 dichloromethane- MN-dimethylformamide (16.5 mL) was treated with PS-carbodiimide (1.5 g, 1.875 mmol; Biotage) and stirred at room temperature for 60 hours. The suspension was filtered through diatomaceous earth, rinsing with dichloromethane. The resulting material was purified by flash chromatography (40 g silica gel column, 5-95% gradient of ethyl acetate in hexanes), then purified further by preparative HPLC [Waters 30x100 mm XBridge Cl 8 OBD 5 mu column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, CDCl3) delta ppm 4.74 (d, J=5.4 Hz, 2 H), 6.40 (s, 1 H), 6.55 (ddd, J=3.1, 2.0, 1.0 Hz, 1 H), 7.10 (dd, J=8.1 , 1.7 Hz, 1 H), 7.20 - 7.25 (m, 1 H), 7.41 (s, 1 <n="59"/>H), 7.63 (d, J=8.1 Hz, 1 H), 7.66 - 7.73 (m, 2 H), 7.81 (dt, J=8.5, 2.0 Hz, 2 H), 8.13 - 8.29 (m,1 H); MS (+DCI) m/z 351 (M+H)+, 368 (M+NH4)+.

Reference： [1]Patent: WO2009/100294,2009,A2 .Location in patent: Page/Page column 57-58

22
[ 864264-03-9 ]
[ 330-17-6 ]
[ 1178607-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU In ISOPROPYLAMIDE at 20℃;	12 In a 96 deep well plate, 4-(trifluoromethylthio)benzoic acid (23 mg, 0.10 mmol) was added dissolved in dimethylacetamide (0.4 mL), followed by O-(7-azabenzotriazol-l-yl)- N,N5N'5N'-tetramethyluronium hexafluorophosphate (HATU, 48 mg, 0.12 mmol, 1.2 equivalents) dissolved in dimethylacetamide (0.3 mL), triethylamine (26 mg, 0.25 mmol, 2.4 equivalents) dissolved in dimethylacetamide (0.3 mL), and finally the N-(I -methyl- lH-indol- 6-yl)methanamine (0.7 mL of a 0.2 M solution in dimethylacetamide, 1.4 equivalents). This was shaken at room temperature overnight. The reaction solution was concentrated to dryness in vacuo, dissolved in 1 : 1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC (Phenomenex Luna C8(2) 5 urn IOOA AXI A column (30mm x 75mm), a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 40mL/min (0-0.5 min 10% A, 0.5-6.0 min linear gradient 10-100% A, 6.0-7.0 min 100% A, 7.0-8.0 min linear gradient 100-10% A)) to give the titled product: 1H NMR (500 MHz, OMSO-Ci(SD2O) δ ppm 3.76 (s, 3 H) 4.61 (s, 2 H) 6.40 (dd, J=3.1, 0.6 Hz, 1 H) 7.05 (dd, J=8.1, 1.4 Hz5 1 H) 7.28 (d, J=3.1 Hz, 1 H) 7.39 (s, 1 H) 7.51 (d, J=7.9 Hz, 1 H) 7.81 - 7.85 (m, 2 H) 7.97 - 8.01 (m, 2 H), 9.22 (s, 1 H); MS (ESI+) m/z 365.0 (M+H)+.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2009/100294, 2009, A2 Location in patent: Page/Page column 46

23
[ 330-17-6 ]
4-(dimethylamino)benzylamine dihydrochloride salt [ No CAS ]
[ 1190069-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	B; 17 N-[4-(dimethylamino)benzyl]-4-[(trifluoromethyl)thio]benzamide A suspension of an amine (0.5 mmol) and a benzoic acid (0.5 mmol) in anhydrous N,N-dimethylformamide (2 mL) was treated with N,N-diisopropylethylamine (iPr2NEt; 245 μL. 1.5 mmol, 3.0 equivalents: Acros) and O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoro-phosphate (HATU; 285 mg, 0.75 mmol, 1.5 equivalents; Aldrich). The mixture was stirred overnight at room temperature, and diluted with dichloromethane (20 mL). The solution was washed with dilute aqueous ammonium chloride (2×7 mL). dilute aqueous sodium bicarbonate (2×7 mL). and brine (2×7 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by either flash chromatography [Analogix pre-packed silica gel cartridges, 5-50% gradient of ethyl acetate/hexanes], or by preparative HPLC [Waters Xterra RP18 30×100 mm column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with sodium hydroxide)] to afford the desired amide product as its free base. Alternatively, the compound was purified on a Waters Symmetry C8 30×100 mm column (flow rate 40 mL/minute, 5-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid) to afford the amide product after evaporation of solvent. The product was prepared from 4-trifluoromethylthiobenzoic acid (133 mg) and 4-(dimethylamino)benzylamine dihydrochloride (134 mg) according to Method B: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.85 (s, 6H), 4.36 (d, J=5.8 Hz, 2H), 6.57-6.75 (m, J=8.8 Hz, 2H), 7.08-7.23 (m, J=8.8 Hz, 2H), 7.76-7.86 (m, J=8.5 Hz, 2H), 7.92-8.06 (m, J=8.5 Hz, 2H), 9.08 (t, J=5.8 Hz, 1H); MS (DCI/NH3) m/z 355.1 (M+H)+; Anal. C17H17F3N2OS: C, H, N.
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	17 A suspension of an amine (0.5 mmol) and a benzoic acid (0.5 mmol) in anhydrous N,N-dimethylformamide (2 mL) was treated with N,N-diisopropylethylamine (iPr2NEt; 245 µL, 1.5 mmol, 3.0 equivalents; Acros) and O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluoro-phosphate (HATU; 285 mg, 0.75 mmol, 1.5 equivalents; Aldrich). The mixture was stirred overnight at room temperature, and diluted with dichloromethane (20 mL). The solution was washed with dilute aqueous ammonium chloride (2 x 7 mL), dilute aqueous sodium bicarbonate (2 x 7 mL), and brine (2 x 7 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by either flash chromatography [Analogix pre-packed silica gel cartridges, 5-50% gradient of ethyl acetate/hexanes], or by preparative HPLC [Waters Xterra RP18 30×100 mm column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with sodium hydroxide)] to afford the desired amide product as its free base. Alternatively, the compound was purified on a Waters Symmetry C8 30×100 mm column (flow rate 40 mL/minute, 5-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid) to afford the amide product after evaporation of solvent. The product was prepared from 4-trifluoromethylthiobenzoic acid (133 mg) and 4-(dimethylamino)benzylamine dihydrochloride (134 mg) according to Method B: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.85 (s, 6 H), 4.36 (d, J=5.8 Hz, 2 H), 6.57 - 6.75 (m, J=8.8 Hz, 2 H), 7.08 - 7.23 (m, J=8.8 Hz, 2 H), 7.76 - 7.86 (m, J=8.5 Hz, 2 H), 7.92 - 8.06 (m, J=8.5 Hz, 2 H), 9.08 (t, J=5.8 Hz, 1 H); MS (DCI/NH3) m/z 355.1 (M+H)+; Anal. C17H17F3N2OS: C, H, N.

Reference： [1]Current Patent Assignee: ABBVIE INC - US2009/253670, 2009, A1 Location in patent: Page/Page column 16; 18
[2]Current Patent Assignee: ABBVIE INC - EP2119476, 2009, A2 Location in patent: Paragraph 0200

24
[ 368869-95-8 ]
[ 330-17-6 ]
[ 1190069-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU In ISOPROPYLAMIDE at 20℃;	A; 1 N-[3-(1H-pyrrol-1-yl)benzyl]-4-[(trifluoromethyl)thio]benzamide In a 96 deep well plate, 4-(trifluoromethylthio)benzoic acid (23 mg, 0.10 mmol) was added dissolved in N,N-dimethylacetamide (0.4 mL), followed by O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) (48 mg. 0.12 mmol, 1.2 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), triethylamine (26 mg, 0.25 mmol, 2.4 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), and finally the amine (0.7 mL of a 0.2 M solution in N,N-dimethylacetamide, 1.4 equivalents). This was shaken at room temperature overnight. The reaction solution was concentrated to dryness in vacuo, dissolved in 1:1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC on a Phenomenex Lunar Combi-HTS C8(2) 5 μm 100 (2.1 mm×30 mm) using a gradient of 10-100% acetonitrile (A) and 0.1% trifluoroacetic acid (B) in water at a flow rate of 2.0 mL/minute (0-0.1 minutes 10% A, 0.1-2.6 minutes 10-100% A, 2.6-2.9 minutes 100% A, 2.9-3.0 minutes 100-10% A.) to give the product. The product was prepared from (3-(1H-pyrrol-1-yl)phenyl)methanamine according to Method A: 1H NMR (500 MHz, DMSO-d6) δ ppm 4.54-4.58 (m, 2H), 6.28 (t, J=2.1 Hz, 2H), 7.22 (d, J=6.4 Hz, 1H), 7.32 (t, J=2.1 Hz, 2H), 7.38-7.47 (m, 2H), 7.51 (s, 1H), 7.81-7.87 (m, J=8.2 Hz, 2H), 7.96-8.03 (m, J=8.2 Hz, 2H), 9.32 (t, J=6.0 Hz, 1H); MS (ESI+) m/z 377.0 (M+H)+.
	With triethylamine; HATU In N,N-dimethyl acetamide at 20℃;	1 In a 96 deep well plate, 4-(trifluoromethylthio)benzoic acid (23 mg, 0.10 mmol) was added dissolved in N,N-dimethylacetamide (0.4 mL), followed by O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATS) (48 mg, 0.12 mmol, 1.2 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), triethylamine (26 mg, 0.25 mmol, 2.4 equivalents) dissolved in N,N-dimethylacetamide (0.3 mL), and finally the amine (0.7 mL of a 0.2 M solution in N,N-dimethylacetamide, 1.4 equivalents). This was shaken at room temperature overnight. The reaction solution was concentrated to dryness in vacuo, dissolved in 1:1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC on a Phenomenex Luna Combi-HTS C8(2) 5µm 100Å (2.1mm × 30mm) using a gradient of 10-100% acetonitrile (A) and 0.1% trifluoroacetic acid (B) in water at a flow rate of 2.0 mL/minute (0-0.1 minutes 10% A, 0.1-2.6 minutes 10-100% A, 2.6-2.9 minutes 100% A, 2.9-3.0 minutes 100-10% A.) to give the product. The product was prepared from (3-(1H-pyrrol-1-yl)phenyl)methanamine according to Method A: 1H NMR (500 MHz, DMSO-d6) δ ppm 4.54 - 4.58 (m, 2 H), 6.28 (t, J=2.1 Hz, 2 H), 7.22 (d, J=6.4 Hz, 1 H), 7.32 (t, J=2.1 Hz, 2 H), 7.38 - 7.47 (m, 2 H), 7.51 (s, 1 H), 7.81 - 7.87 (m, J=8.2 Hz, 2 H), 7.96 - 8.03 (m, J=8.2 Hz, 2 H), 9.32 (t, J=6.0 Hz, 1 H); MS (ESI+) m/z 377.0 (M+H)+

Reference： [1]Current Patent Assignee: ABBVIE INC - US2009/253670, 2009, A1 Location in patent: Page/Page column 16-17
[2]Current Patent Assignee: ABBVIE INC - EP2119476, 2009, A2 Location in patent: Paragraph 0179; 0184

25
[ 1143624-67-2 ]
[ 330-17-6 ]
[ 1143624-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 3h;	2.A Example 2; Compound 1 of Table I; N-[6-(4-bromophenyl)-2-[(butyrylamino)methyl]-5-(2,4-dichlorophenyl)pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide; A) N-[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-(methoxymethyl)pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide; 18.0 g of the 1-[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-(methoxymethyl)pyrid-3-yl]methanamine obtained in step B) of Example 1 are dissolved in 200 ml of DCM, followed by addition of 8.38 g of 4-(trifluoromethylthio)benzoic acid, 19.1 ml of triethylamine and 19.63 g of PyBOP.The medium is stirred for 3 hours at room temperature and is then washed successively with 200 ml of 10% HCl, with 200 ml of aqueous 10% NaHCO3 solution, and then with 200 ml of distilled water.The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product. This product is purified by chromatography on silica, eluting with a DCM/MeOH gradient of from 0 to 1% MeOH over 1 hour.The fractions containing the purified product are combined and brought to dryness to give 18.0 g of expected product.LC/MS (Conditions C): MH+=654.8; rt=12.12 min

Reference： [1]Current Patent Assignee: SANOFI - US2010/256202, 2010, A1 Location in patent: Page/Page column 18

26
[ 727385-55-9 ]
[ 330-17-6 ]
[ 1222868-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Rai, Ganesha; Kenyon, Victor; Jadhav, Ajit; Schultz, Lena; Armstrong, Michelle; Jameson, J. Brian; Hoobler, Eric; Leister, William; Simeonov, Anton; Holman, Theodore R.; Maloney, David J. [Journal of Medicinal Chemistry, 2010, vol. 53, # 20, p. 7392 - 7404]

27
[ 333-47-1 ]
[ 590-29-4 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With [PhCOPd(PtBu₃)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;

Reference： [1]Korsager, Signe; Taaning, Rolf H.; Skrydstrup, Troels [Journal of the American Chemical Society, 2013, vol. 135, # 8, p. 2891 - 2894]

28
[ 330-17-6 ]
N-(1-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-yloxy)-2-cyanopropan-2-yl)-4-(trifluoromethylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetic acid; potassium permanganate / water / 16 h / 20 °C 2.1: thionyl chloride / dichloromethane / 1 h / 60 °C 2.2: 20 °C

Reference： [1]Current Patent Assignee: PFIZER INC; ELI LILLY & CO - WO2014/149793, 2014, A1

29
[ 330-17-6 ]
2-amino-3-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-methylpropanenitrile [ No CAS ]
N-(1-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-cyanopropan-2-yl)-4-(trifluoromethylthio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: 4-(trifluoromethylthio)benzoic acid With thionyl chloride In dichloromethane at 60℃; for 1h; Stage #2: 2-amino-3-(7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)-2-methylpropanenitrile With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	18 Example 18 (S)-N-(1-((7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)-2-cyanopropan-2-yl)-4-((trifluoromethyl)thio)benzamide Example 18 (S )-N-( 1 -((7-chloro- 1 -hydroxy- 1.3 -dihydrobenzo [c] [ 1.2]oxaborol-6-yl)oxy )-2-cyanoprop an-2-ylV4-((trifluoromethyl)thio)benzamide A mixture of 4-((trifluoromethyl)thio)benzoic acid (1.84 g, 8.27 mmol) in DCM (20 mL) and SOCl2 (20 mL) is stirred at 60°C for lh. The solution is concentrated in vacuo to got the acyl chloride, which is added to a mixture of 2-amino-3-(7-chloro-l- hydroxy-l,3-dihydrobenzo[c][l,2]oxaborol-6-yloxy)-2-methylpropanenitrile (2.2 g, 8.27 mmol) and DIPEA (3.2 g, 24.8 mmol) in THF (50 mL). The mixture is stirred at rt overnight and concentrated. The residue is dissolved in EA (200mL), washed with brine (3 x 30mL), dried over Na2S04, concentrated under reduced pressure and purified by column chromatography to give the desired (N-(l-((7-chloro-l-hydroxy-l,3-dihydrobenzo [c] [ 1 ,2]oxaborole-6-yl)oxy) -2-cyanopropan-2-yl)-4-((trifluoromethyl)thio)benzamide as pale white solid (1.8g, yield 47%). :H NMR (400 MHz, DMSO-de): δ 9.18 (m, 2H), 7.96 (d, 2H), 7.86 (d, 2H), 7.33-7.32 (m, 2H), 4.92 (s, 2H), 4.57 (d, 1H), 4.40 (d, 1H), 1.86 (s, 3H) ppm; HPLC purity: 97.4% at 220 nm and 97.1% at 254 nm. MS: m/z = 471.1 (M+l, ESI+).

Reference： [1]Current Patent Assignee: PFIZER INC; ELI LILLY & CO - WO2014/149793, 2014, A1 Location in patent: Page/Page column 73

30
[ 2314-97-8 ]
[ 1074-36-8 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2,2'-bipyridyl)ruthenium dichloride; triethylamine In acetonitrile at 20℃; for 1h; Irradiation;

Reference： [1]Straathof, Natan J. W.; Tegelbeckers, Bart J. P.; Hessel, Volker; Wang, Xiao; Nol, Timothy [Chemical Science, 2014, vol. 5, # 12, p. 4768 - 4773]

31
[ 696-62-8 ]
[ 330-17-6 ]
4'-methoxy-5-((trifluoromethyl)thio)-[1,1'-biphenyl]-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; caesium carbonate; N-acetyl-L-isoleucine; silver carbonate at 30℃; for 36h; Schlenk technique; Inert atmosphere;

Reference： [1]Zhu, Changlei; Zhang, Yuanfei; Kan, Jian; Zhao, Huaiqing; Su, Weiping [Organic Letters, 2015, vol. 17, # 14, p. 3418 - 3421]

32
[ 150-13-0 ]
tetramethylammonium trifluoromethanethiolate [ No CAS ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
198 mg	Stage #1: 4-amino-benzoic acid With tetrafluoroboric acid; tert.-butylnitrite In ethanol; water at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: tetramethylammonium trifluoromethanethiolate With copper(I) thiocyanate In acetonitrile at 20℃; for 1h; Inert atmosphere;

Reference： [1]Matheis, Christian; Wagner, Victoria; Goossen, Lukas J. [Chemistry - A European Journal, 2016, vol. 22, # 1, p. 79 - 82]

33
[ 330-17-6 ]
4-methoxy-N-(2-methoxyethyl)-2-(4-piperidylmethyl)-2H-indazol-5-carboxamide [ No CAS ]
[ 1442120-11-7 ]

Yield	Reaction Conditions	Operation in experiment
25 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	269 4-methoxy-N-(2-methoxyethyl)-2-[(1-{4-[(trifluoromethyl)sulphanyl]benzoyl}-piperidin-4-yl)methyl]-2H-indazole-5-carboxamide General procedure: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 25 mg of the title compound was obtained from 100 mg of the compound prepared in Example 266b and 96 mg of 4-[(trifluoromethyl)sulphanyl]benzoic acid in DMF. 1H-NMR (400 MHz, DMSO-d6): δ [ppm], 1.09-1.37 (2H), 1.38-1.72 (2H), 2.23-2.39 (1H), 2.70-2.93 (1H), 2.95-3.16 (1H), 3.30 (3H), 3.40-3.55 (5H), 4.20 (3H), 4.35 (d, 3H), 7.25 (1H), 7.46-7.58 (2H), 7.66 (1H), 7.78 (2H), 8.20 (1H), 8.82 (1H).

Reference： [1]Current Patent Assignee: BAYER AG - US2016/89364, 2016, A1 Location in patent: Page/Page column 24; 139

34
[ 330-17-6 ]
[ 292638-85-8 ]
methyl 2-(3-oxo-6-((trifluoromethyl)thio)-1,3-dihydroisobenzofuran-1-yl)acetate [ No CAS ]
(E)-methyl 3-(1-(2-methoxy-2-oxoethyl)-3-oxo-6-((trifluoromethyl)thio)-1,3-dihydroisobenzofuran-4-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 42% 2: 46%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; potassium hydrogencarbonate; acetic acid In 1,2-dichloro-ethane at 60℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Jiang, Quandi; Zhu, Changlei; Zhao, Huaiqing; Su, Weiping [Chemistry - An Asian Journal, 2016, vol. 11, # 3, p. 356 - 359]

35
[ 1442116-78-0 ]
[ 330-17-6 ]
[ 1442120-38-8 ]

Yield	Reaction Conditions	Operation in experiment
67 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	288 4-methyl-N-(2,2,2-trifluoroethyl)-2-[(1-{4-[(trifluoromethyl)sulphanyl]benzoyl}-piperidin-4-yl)methyl]-2H-indazole-5-carboxamide General procedure: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 67 mg of the title compound was obtained from 100 mg of 71a and 94 mg of 4-[(trifluoromethyl)sulphanyl]benzoic acid in DMF. 1H-NMR (400 MHz, DMSO-d6): δ [ppm], 1.12-1.35 (2H), 1.35-1.70 (2H), 2.21-2.40 (1H), 2.54 (3H), 2.70-2.88 (1H), 2.94-3.12 (1H), 3.38-3.61 (1H), 4.07 (2H), 4.36 (3H), 7.21 (1H), 7.37-7.60 (3H), 7.78 (2H), 8.55 (1H), 8.81 (1H).

Reference： [1]Current Patent Assignee: BAYER AG - US2016/89364, 2016, A1 Location in patent: Page/Page column 24; 145

36
[ 524-38-9 ]
[ 330-17-6 ]
1,3-dioxoisoindolin-2-yl 4-((trifluoromethyl)thio)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere;

Reference： [1]Cheng, Wan-Min; Shang, Rui; Zhao, Bin; Xing, Wei-Long; Fu, Yao [Organic Letters, 2017, vol. 19, # 16, p. 4291 - 4294]

37
[ 330-17-6 ]
[ 1005206-25-6 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4291 - 4294

38
(4-((trifluoromethyl)thio)phenyl)methanol [ No CAS ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With diethylene glycol dimethyl ether at 70℃; for 0.666667h; Sonication;	22 Example 22: Preparation of 4-trifluoromethylthiobenzoic acid: In a 10 mL round bottom flask, 1.04 g of 4-trifluoromethylthiobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added, and the resulting mixture was placed in an ultrasonic reaction apparatus.40KHz/30W/70°C ultrasonic irradiation was allowed to open for 40 minutes.Diethylene glycol dimethyl ether was removed under reduced pressure and recrystallized to give 1.0 g of 4-trifluoromethylthiobenzoic acid (yield: 91%).

Reference： [1]Current Patent Assignee: CENTRAL SOUTH UNIVERSITY - CN108467342, 2018, A Location in patent: Paragraph 0140; 0141

39
[ 330-17-6 ]
[ 1204331-60-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: oxone / methanol; water / 102 h / 20 - 50 °C 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1.5 h 2.2: 20 °C

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2010/5783, 2010, A1

40
[ 330-17-6 ]
N-{4-[1-(4-trifluoromethanesulfonyl-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzoyl}-guanidine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: oxone / methanol; water / 102 h / 20 - 50 °C 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1.5 h 2.2: 20 °C 3.1: hydrogen / palladium hydroxide, 20 wt% on carbon / ethanol / 16 h / Inert atmosphere

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2010/5783, 2010, A1

41
[ 330-17-6 ]
1-(4-(aminomethyl)phenyl)propan-1-one [ No CAS ]
N-(4-propionylbenzyl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 10h;

Reference： [1]Yang, Yiqing; Cao, Lin; Gao, Hongying; Wu, Yue; Wang, Yaxin; Fang, Fang; Lan, Tianlong; Lou, Zhiyong; Rao, Yu [Journal of Medicinal Chemistry, 2019, vol. 62, # 8, p. 4056 - 4073]

42
[ 330-17-6 ]
methyl 4-(difluoro(trifluoromethyl)-λ⁴-sulfaneyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / 16 h / 80 °C / Inert atmosphere 2: potassium fluoride; trichloroisocyanuric acid; trifluoroacetic acid / acetonitrile / 18 h / 40 °C / Inert atmosphere; Sealed tube

Reference： [1]Brüning, Fabian; Pitts, Cody Ross; Kalim, Jorna; Bornemann, Dustin; Ghiazza, Clément; de Montmollin, Jean; Trapp, Nils; Billard, Thierry; Togni, Antonio [Angewandte Chemie - International Edition, 2019, vol. 58, # 52, p. 18937 - 18941][Angew. Chem., 2019, vol. 131, # 52, p. 19113 - 19117,5]

43
[ 330-17-6 ]
[ 98-80-6 ]
[ 41830-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(trifluoromethylthio)benzoic acid With potassium phosphate In 1,4-dioxane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With 2-chloro-1,3-dimethylimidazolinium chloride In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #3: phenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane at 90℃; for 16h; Inert atmosphere;

Reference： [1]Brüning, Fabian; Pitts, Cody Ross; Kalim, Jorna; Bornemann, Dustin; Ghiazza, Clément; de Montmollin, Jean; Trapp, Nils; Billard, Thierry; Togni, Antonio [Angewandte Chemie - International Edition, 2019, vol. 58, # 52, p. 18937 - 18941][Angew. Chem., 2019, vol. 131, # 52, p. 19113 - 19117,5]

44
[ 330-17-6 ]
[ 98-80-6 ]
(4-(difluoro(trifluoromethyl)-λ⁴-sulfaneyl)phenyl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium phosphate / 1,4-dioxane / 0.08 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 1.3: 16 h / 90 °C / Inert atmosphere 2.1: potassium fluoride; trichloroisocyanuric acid; trifluoroacetic acid / acetonitrile / 18 h / 40 °C / Inert atmosphere; Sealed tube

Reference： [1]Brüning, Fabian; Pitts, Cody Ross; Kalim, Jorna; Bornemann, Dustin; Ghiazza, Clément; de Montmollin, Jean; Trapp, Nils; Billard, Thierry; Togni, Antonio [Angewandte Chemie - International Edition, 2019, vol. 58, # 52, p. 18937 - 18941][Angew. Chem., 2019, vol. 131, # 52, p. 19113 - 19117,5]

45
[ 67-56-1 ]
[ 330-17-6 ]
[ 88489-60-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sulfuric acid at 80℃; for 16h; Inert atmosphere;

Reference： [1]Brüning, Fabian; Pitts, Cody Ross; Kalim, Jorna; Bornemann, Dustin; Ghiazza, Clément; de Montmollin, Jean; Trapp, Nils; Billard, Thierry; Togni, Antonio [Angewandte Chemie - International Edition, 2019, vol. 58, # 52, p. 18937 - 18941][Angew. Chem., 2019, vol. 131, # 52, p. 19113 - 19117,5]

46
[ 330-17-6 ]
[ 1612-76-6 ]
N-(5-phenyl-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	Amide coupling of compounds: General procedure: A 20 mL screw caped vial, charged with the corresponding acid (0.5 mmol), amine (0.5 mmol), BOP reagent (1.4 mmol) and diisopropylethylamine (13 mmol) in anhydrous DMF solvent (3 mL) was stirred at room temperature for 16 h. After completion, the reaction mixture was concentrated under reduced pressure, followed by flash column chromatography (hexanes:ethyl acetate 80:20 to 60:40) give the desired product.

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]
[2]Current Patent Assignee: PURDUE UNIVERSITY SYSTEM - WO2020/219792, 2020, A1 Location in patent: Paragraph 0098; 00102; 00230-00232

47
[ 330-17-6 ]
2-amino-5-(2-fluorophenyl)-1,3,4-oxadiazole [ No CAS ]
N-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

48
[ 330-17-6 ]
[ 2138-98-9 ]
N-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

49
[ 330-17-6 ]
2-amino-5-(3'-fluorophenyl)-1,3,4-oxadiazole [ No CAS ]
N-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

50
[ 330-17-6 ]
[ 1673-45-6 ]
N-(5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

51
[ 330-17-6 ]
[ 1673-44-5 ]
N-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

52
[ 330-17-6 ]
[ 5711-64-8 ]
N-(5-(3-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

53
[ 330-17-6 ]
[ 7659-07-6 ]
N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 11934 - 11944

54
[ 33621-61-3 ]
[ 330-17-6 ]
N-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

55
2-amino-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole [ No CAS ]
[ 330-17-6 ]
N-(5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

56
[ 5711-61-5 ]
[ 330-17-6 ]
N-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

57
[ 330-17-6 ]
[ 33621-60-2 ]
N-(5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

58
[ 330-17-6 ]
[ 49579-79-5 ]
N-(5-(4-isopropylphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

59
[ 60160-13-6 ]
[ 330-17-6 ]
N-(5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

60
[ 1016495-77-4 ]
[ 330-17-6 ]
N-(5-(3,5-dichlorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

61
[ 330-17-6 ]
C₉H₈ClN₃O₂ [ No CAS ]
N-(5-(5-chloro-2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Naclerio, George A.; Abutaleb, Nader S.; Li, Daoyi; Seleem, Mohamed N.; Sintim, Herman O. [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11934 - 11944]

62
[ 330-17-6 ]
[ 5711-72-8 ]
N-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 11934 - 11944

63
[ 330-17-6 ]
C₁₇H₁₃ClF₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium permanganate; acetic acid / water / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C

Reference： [1]Current Patent Assignee: PRAXIS PRECISION MEDICINES INC; PRAKISS PREC DRUG - WO2020/227097, 2020, A1

64
[ 1074-36-8 ]
[ 2926-29-6 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrabutylammonium tetrafluoroborate; sodium bromide In acetonitrile at 20℃; for 10h; Electrolysis; Inert atmosphere;

Reference： [1]Zhu, Xing-Xing; Wang, Huai-Qin; Li, Chen-Guang; Xu, Xiao-Lan; Xu, Jun; Dai, Jian-Jun; Xu, Hua-Jian [Journal of Organic Chemistry, 2021, vol. 86, # 22, p. 16114 - 16120]

65
[ 330-17-6 ]
[ 330-14-3 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;	Acyl chlorides General procedure: The acid (5 mmol) was dissolved in anhydrous CH2Cl2 (10 mL) and DMF (a few drops) added.Oxalyl chloride (6 mmol, 1.2 equiv.) was added dropwise to the solution, that was cooled in an icewater bath. The resulting mixture was allowed to stir at room temperature for an additional 4 h andthe solvent was evaporated to afford the crude acyl chloride, which was used directly in the nextstep.

Reference： [1]Flavell, Robert R.; Liu, Jianbo; Parker, Matthew F. L.; Toste, F. Dean; Wang, Sinan; Wilson, David M. [Chem, 2021, vol. 7, # 8, p. 2245 - 2255]

66
[ 330-17-6 ]
N-phenethyl-N-(trifluoromethyl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0 - 20 °C 2: silver fluoride; pyridine / dichloromethane / 24 h / 20 °C / Sealed tube

Reference： [1]Flavell, Robert R.; Liu, Jianbo; Parker, Matthew F. L.; Toste, F. Dean; Wang, Sinan; Wilson, David M. [Chem, 2021, vol. 7, # 8, p. 2245 - 2255]

67
[ 128273-56-3 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 4-phenylnaphthalene-1,2-dione; tetra-(n-butyl)ammonium iodide / acetonitrile; water / 24 h / 80 °C 2: tert.-butylhydroperoxide / water / 24 h / 80 °C

Reference： [1]Kim, Hun Young; Oh, Kyungsoo; Si, Tengda [Chemistry - A European Journal, 2021, vol. 27, # 72, p. 18150 - 18155]

68
[ 4021-50-5 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylhydroperoxide In water at 80℃; for 24h;

Reference： [1]Kim, Hun Young; Oh, Kyungsoo; Si, Tengda [Chemistry - A European Journal, 2021, vol. 27, # 72, p. 18150 - 18155]

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Ghs Precautionary Statements

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

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere