[ CAS No. 92-30-8 ] {[proInfo.proName]}

Name: 92-30-8|2-(Trifluoromethyl)-10H-phenothiazine|98%
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2D 3D

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Quality Control of [ 92-30-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 92-30-8 ]

SDS Specification

Alternatived Products of [ 92-30-8 ]

Product Details of [ 92-30-8 ]

CAS No. :	92-30-8	MDL No. :	MFCD00005018
Formula :	C₁₃H₈F₃NS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RKGYJVASTMCSHZ-UHFFFAOYSA-N
M.W :	267.27	Pubchem ID :	7082
Synonyms :

Calculated chemistry of [ 92-30-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.05
TPSA :	37.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	5.03
Log Po/w (WLOGP) :	5.69
Log Po/w (MLOGP) :	4.42
Log Po/w (SILICOS-IT) :	4.17
Consensus Log Po/w :	4.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.09
Solubility :	0.00216 mg/ml ; 0.00000807 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.55
Solubility :	0.000745 mg/ml ; 0.00000279 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.96
Solubility :	0.000295 mg/ml ; 0.0000011 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.63

Safety of [ 92-30-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 92-30-8 ]

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

Upstream synthesis route of [ 92-30-8 ]
Downstream synthetic route of [ 92-30-8 ]

[ 92-30-8 ] Synthesis Path-Upstream 1~18

1
[ 672-57-1 ]
[ 1204-55-3 ]
[ 92-30-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10 h; Inert atmosphere	General procedure: To an oven-dried 25 mL ground mouth test tube equipped with a stir bar was added S-2-acetamidophenyl ethanethioate (0.5 mmol), 1-bromo-2-iodobenzene (0.6 mmol), Cs₂CO₃(2.0 mmol), DMF (3 mL). The test tube was sealed with a sleeve rubber stopper and evacuated and refilled with argon for three cycles. The mixture was stirred 130 ^oC for 10 hours. After cooling to room temperature, the reaction mixture was quenched with water (20 mL), and extracted with ethyl acetate (20 mL) for three times. The combined organic layer was dried with anhydrous MgSO₄, and condensed in vacuum on a rotary evaporator. The residual was purified on a silica gel chromatograph column by means of gradient elution (eluent: petroleum ether / ethyl acetate) to give the desired product.

Reference： [1] Synthetic Communications, 2017, vol. 47, # 7, p. 710 - 715

2
[ 583-55-1 ]
[ 19406-49-6 ]
[ 92-30-8 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 43, p. 5367 - 5369

3
[ 694-80-4 ]
[ 19406-49-6 ]
[ 92-30-8 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 43, p. 5367 - 5369

4
[ 19406-49-6 ]
[ 108-94-1 ]
[ 92-30-8 ]

Reference： [1] RSC Advances, 2013, vol. 3, # 40, p. 18605 - 18608

5
[ 89507-40-4 ]
[ 92-30-8 ]
[ 89507-41-5 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 1, p. 87 - 90

6
[ 1444-47-9 ]
[ 481075-58-5 ]
[ 92-30-8 ]

Reference： [1] Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6128 - 6132

7
[ 101-23-5 ]
[ 92-30-8 ]

Reference： [1] Journal of Organic Chemistry, 1950, vol. 15, p. 1125,1128
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 4375,4377
[3] Pharmaceutical Chemistry Journal, 1971, vol. 5, p. 330 - 333[4] Khimiko-Farmatsevticheskii Zhurnal, 1971, vol. 5, # 6, p. 18 - 20

8
[ 328-14-3 ]
[ 92-30-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 7, p. 1291 - 1294

9
[ 101-23-5 ]
[ 92-30-8 ]
[ 343-21-5 ]

Reference： [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4375,4377

10
[ 81586-77-8 ]
[ 92-30-8 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 1, p. 87 - 90
[2] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 1, p. 87 - 90

11
[ 89507-39-1 ]
[ 92-30-8 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 1, p. 87 - 90
[2] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 1, p. 87 - 90

12
[ 89507-40-4 ]
[ 92-30-8 ]
[ 4921-08-8 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 1, p. 87 - 90

13
[ 530-78-9 ]
[ 92-30-8 ]

Reference： [1] Journal of the American Chemical Society, 1960, vol. 82, p. 1600 - 1607

14
[ 98-16-8 ]
[ 92-30-8 ]

Reference： [1] Journal of the American Chemical Society, 1960, vol. 82, p. 1600 - 1607

15
[ 7639-63-6 ]
[ 92-30-8 ]

Reference： [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1577,1589

16
[ 108-86-1 ]
[ 92-30-8 ]

Reference： [1] Journal of Organic Chemistry, 1950, vol. 15, p. 1125,1128

17
[ 351-36-0 ]
[ 92-30-8 ]

Reference： [1] Journal of Organic Chemistry, 1950, vol. 15, p. 1125,1128

18
[ 346-44-1 ]
[ 92-30-8 ]

Reference： [1] Journal of the Chemical Society [Section] C: Organic, 1970, p. 2437 - 2441

[ 92-30-8 ] Synthesis Path-Downstream 1~19

2
[ 530-78-9 ]
[ 92-30-8 ]

Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 1600 - 1607

3
[ 92-30-8 ]
[ 109-70-6 ]
[ 1675-46-3 ]

Yield	Reaction Conditions	Operation in experiment
69.8%	With sodium hydride; potassium carbonate In tetrahydrofuran; mineral oil at 65℃; Inert atmosphere;	1 2-10: 2-Trifluoromethylphenothiazine (2.00 g, 7.4831 mmol) was placed in a 500 mL flask, THF (100 mL) dried overanhydrous K2CO3 was added, and then 60% NaH was added sequentially under N2 protection. Mineral oil(1.1973 g, 29.9323 mmol) and 1-bromo-3-chloropropane (2.9601 mL, 29.9323 mmol) were refluxed overnightat a bath temperature of 65 °C. After cooling to room temperature, the reaction mixture was poured into EtOAc EtOAc (EtOAc)EtOAc. Ethylacetate (50 mL) was added to dissolve, and silica gel powder (20 g) was added to the solution to dryness, and theresidue was applied to a silica gel column, eluted with ethyl acetate and petroleum ether, and the product wascollected, dried, and dried in vacuo. Product 2-10 (4.9444 g, yield 69.8%).
66.7%	With sodium hydride In N,N-dimethyl-formamide
58%	With sodium hydride In toluene at 110℃; for 18h;	2 Compound 2; 10-(3-Chloropropyl)-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethyl phenothiazine (compound 1) (2g, 7.49 mmol) and sodium hydride (0.5 g, 10.42 mmol) in dry toluene (30 mL) was added l-bromo-3-chloropropane (1.57g, 10 mmol). The reaction mixture was stirred for 18 hours at 110 C under an atmosphere of argon. The solution was cooled to room temperature and poured into an ice- water mixture, the crude product was extracted with ethyl acetate (3x50 mL) and the combined organic phase dried over anhydrous sodium sulphate. Final purification was performed by column chromatography (9:1 hexane: ethyl acetate) on silica gel to give 10-(3- chloropropyl)- 2-trifluoromethylphenothiazine (1.5 g, 58% ) as a solid.

	With sodium peroxide; sodium amide In ammonia
	With sodium hydride Yield given;
	With caesium carbonate In N,N-dimethyl-formamide at 65℃; for 12h;	4.1 Step 1 : Synthesis of 10-(3-chloropropyl)-2-(trifluoromethyl)-10H-phenothiazine. A solution of2- (trifluoromethyl)-lOH-phenothiazine (2.04g, 7.6mmol) and DMF (16mL) was mixed with CS2C03 (7.5g, 22.9mmol) and l-bromo-3-chloropropane (1.1 mL, 11.5mmol). The reaction mixture was heated at 65 °C for 12h. Once no starting material was observed by analytical LCMS, EtOAC (250mL) and brine (250mL) were added. The organic layer was separated, and the aqueous layer was washed with EtOAC (3 χ l00mL). The combined organic extracts were washed with brine (2 χ lOOmL), dried over MgSO ι, and concentrated to afford the title compound.
	With caesium carbonate In N,N-dimethyl-formamide at 30 - 80℃; for 50h;	1; 19 Intermediate synthesis of 1-1 ( 10-(3-chloropropyl)-2-(trifluoromethyl)- 10//-phenothiazine) 1 -Bromo-3-chloropropane (37.68 g, 200 mmol) was added to 2-(trifluoromethyl)- l0i7-phenothiazine (26.7 g, 100 mmol) and Cs2CC>3 (65.6 g, 200 mmol) in DMF (130 mL). The mixture was stirred at 30 °C for 48 h and then heated to 80 °C for 2 h. The mixture was cooled to rt then H20 was added. The mixture was extracted with PE three times (200 mL x 3). The combined organic phase was washed with brine, dried over Na2S04, and concentrated in vacuo. The residue was purified by column chromatography (PE 100%, PE:EtOAc = 60: 1) to get 10.8 g pure and 19 g crude. LC-MS: Rt = 2.29 min; ESI, m/z 344 [M+l]+.
	With sodium hydride In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN104829554, 2018, B Location in patent: Paragraph 0028-0031
[2]Dunn, Elyse A.; Roxburgh, Marina; Larsen, Lesley; Smith, Robin A.J.; McLellan, Alexander D.; Heikal, Adam; Murphy, Michael P.; Cook, Gregory M. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5320 - 5328]
[3]Current Patent Assignee: ASTRAZENECA PLC - WO2008/27521, 2008, A1 Location in patent: Page/Page column 55
[4]Ratouis,R.; Boissier,J.R. [Bulletin de la Societe Chimique de France, 1966, p. 2963 - 2965]
[5]Schepartz, Alarma; Cuenoud, Bernard [Journal of the American Chemical Society, 1990, vol. 112, # 8, p. 3247 - 3249]
[6]Current Patent Assignee: INCEPTION ORION - WO2013/43744, 2013, A2 Location in patent: Paragraph 00113
[7]Current Patent Assignee: CAMP4 THERAPEUTICS CORPORATION INC - WO2019/195789, 2019, A1 Location in patent: Paragraph 00356; 00410; 00413
[8]Wang, Yuanjiang; Lv, Zhaodan; Chen, Feihong; Wang, Xing; Gou, Shaohua [Journal of Medicinal Chemistry, 2021, vol. 64, # 17, p. 12877 - 12892]

4
[ 92-30-8 ]
[ 164149-27-3 ]
[ 1009797-52-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydride In tetrahydrofuran for 12h; Heating / reflux;	13 Compound 13; 10-[3-(N-Boc-4-piperidyl)propyl]-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethylphenothizine 1 (400 mg, 1.5 mmol), sodium hydride (100 mg, 2 mmol) in DME (10 mL) at 90 C was added N- Boc-4-(3-bromopropyl)piperidine 12 (380 mg, 1.24 mmol) dropwise under an atmosphere of argon. The reaction mixture was stirred for 12h at reflux. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was partitioned between ethyl acetate (25 mL) and brine (1OmL). The organic layer was dried over anhydrous sodium sulphate, filtered, and evaporated. The resulting residue was purified by silica gel column chromatography (8:2 hexane : ethyl acetate) on silica gel to give phenothiazine derivative 13 (425 mg, 70%) as a solid. MS(ESI): m/z493 (M+H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2008/27521, 2008, A1 Location in patent: Page/Page column 59

5
[ 6940-78-9 ]
[ 92-30-8 ]
[ 3870-95-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride; In toluene; at 110℃; for 18h;	Compound 21; 10-(4-chlorobutyl)-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethylphenothiazine 1 (4.Og, 15 mmol), sodium hydride (1.2g, 24 mmol) in dry toluene (40 mL), 1-bromo 4- chlorobutane (3.0 g, 17.6 mmol) was added. The reaction mixture was stirred for 18 hours at 110 C under an atmosphere of argon. The solution was cooled to room temperature and poured into an ice-water mixture. The crude product was extracted <n="63"/>with ethyl acetate (3chi50mL) and the organic phase was dried over sodium sulphate. Final purification was performed by column chromatography (9: 1 hexane: ethyl acetate) on silica gel to give 21 (3.5 g, 65% ) as an oil.
60%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	A mixture of 1-1 [2-(trifluoromethyl)-l0i7-phenothiazine] (300 mg, 1.12 mmol), 1- bromo-4-chlorobutane (391 mg, 2.28 mmol) and CS2CO3 (1.04 g, 3.19 mmol) in DMF (15 mL) was stirred at rt overnight. The mixture was poured into cool water (20 mL) and extracted with EtOAc (15 mL x 3). The combined organic extracts were washed with brine, dried over NaiSCE. fdtered and concentrated under reduced pressure. The residue was purified by column chromatography (petrol ether: EtOAc =10: 1) to provide a yellow solid (240 mg, 60% yield). LC-MS: Rt = 2.30 min; ESI, m/r 358 [M + 1] +
56.72%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 100℃; for 12h;	After dissolving 2-(trifluoromethyl)-10H-phenothiazine (2.0 g, 7.48 mmol) in N,N-dimethylformamide (2 mL), 60% sodium hydride (149.70 mg, 3.74 mmol) and <strong>[6940-78-9]1-bromo-4-chlorobutane</strong> (1.16 mL, 10.10 mmol) were added at 0 C. The reactants were heated at 100 C. for 12 hours under reflux. After the reaction was completed, the reaction solution was extracted with ethyl acetate and the organic layer was dried with magnesium sulfate, filtered under reduced pressure and then concentrated under reduced pressure. The target compound (1.52 g) was obtained with a yield of 56.72% by separating the residue by chromatography (ethyl acetate/n-hexane=1/20). 1H NMR (400 MHz, CDCl3): delta 1.89-2.00 (4H, m, 2CH2), 3.40 (1H, t, J=6.02 Hz, CH), 3.54 (1H, t, 6.18 Hz, CH), 3.94 (2H, t, 6.02 Hz, CH2), 6.89 (1H, d, J=8.12 Hz, CH), 6.96 (1H, t, 7.44 Hz, CH) 7.03 (1H, s, CH), 7.13-7.17 (2H, m, 2CH), 7.21 (2H, t, 8.16 Hz, 2CH).

Reference： [1]Patent: WO2008/27521,2008,A1 .Location in patent: Page/Page column 61-62
[2]Patent: WO2019/195789,2019,A1 .Location in patent: Paragraph 00379-00380
[3]Patent: US10035795,2018,B1 .Location in patent: Paragraph 14; 15
[4]Chemistry - An Asian Journal,2019,vol. 14,p. 4035 - 4041

6
[ 92-30-8 ]
[ 169457-73-2 ]
[ 1009797-58-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride; In 1,2-dimethoxyethane; for 12h;Heating / reflux;	Compound 27; 10-[2-(N-Boc-4-piperidyl)ethyl]-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethylphenothizine 1 (0.9 Ig, 3.42 mmol), sodium hydride (0.2g, 4.0 mmol) in DME (20 mL) at 90C was added N-Boc- 4-(2-bromoethyl)piperidine 26 (1.Og, 3.42 mmol) dropwise under an atmosphere of argon. The reaction mixture was stirred for 12h at reflux temperature. The reaction mixture was filtered, and filtrate was concentrated under vacuum. The residue was partitioned between ethyl acetate (25 mL) and brine (1OmL). The organic layer was dried over anhydrous sodium sulphate, filtered, and evaporated. The resulting residue was purified by column chromatography (8:2 n-hexane : ethyl acetate) on silica gel to give phenothiazine derivative 27 (0.3 g, 18%) as a foam. MS(ESI): m/z 479(M+H).

Reference： [1]Patent: WO2008/27521,2008,A1 .Location in patent: Page/Page column 61-62

7
[ 92-30-8 ]
[ 69-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) nBuLi, (ii) /BRN= 1114944/ 2: NaI / butan-2-one / 20 h / Heating
	Multi-step reaction with 2 steps 1: (i) NaNH₂, toluene, (ii) aq. KOH, EtOH 2: methanol / 1 h / 55 °C

Reference： [1]Hirata; Peng; Driscoll [Journal of Pharmaceutical Sciences, 1978, vol. 67, # 2, p. 157 - 162]
[2]ANDERSON [Arzneimittel-Forschung/Drug Research, 1962, vol. 12, p. 937 - 942]

8
[ 948-65-2 ]
[ 92-30-8 ]
C₂₇H₁₇F₃N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(I) bromide In N,N-dimethyl-formamide at 60℃; for 24h; Schlenk technique;	8 Example 1 General procedure: In an air atmosphere, 2-phenylindole 1a (0.60 mmol), phenothiazine 2a (0.30 mmol),10mol% cuprous bromide and DMF (2mL) were added to the Schlenk reaction tube in sequence.In a constant temperature heating magnetic stirrer, the reaction was stirred at room temperature for 24 hours.After the reaction was completed, it was quenched with distilled water, extracted with ethyl acetate (3 × 20 mL), and the organic layers were combined.After drying over anhydrous sodium sulfate and spinning the organic phase, The crude product by column chromatography to give the pure product 3a (103.1 mg, 88%).
86%	With copper(I) bromide In N,N-dimethyl-formamide at 60℃; for 24h;
75%	With oxygen In acetic acid at 150℃; for 24h; Sealed tube;

74%

With oxygen; potassium carbonate In 1,2-dichloro-benzene at 150℃; for 12h;

1. Typical procedure for the synthesis of 3a General procedure: A stirred mixture of phenothiazine (100 mg, 0.5 mmol),3,5-dimethylphenol (183 mg, 1.5 mmol), and K2CO3 (69 mg,0.5 mmol) in ODCB (1.5 mL) was heated to 130 oC for 6 h under O2 balloon atmosphere. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/EtOAc, 20:1) para-3a (103 mg, 64%) and ortho-3a (34 mg, 21%) were obtained as white solids. Other compounds were synthesized similarly, and the spectroscopic data of 3a-3m and the sulfoxide of 3g are as follows.

Reference： [1]Current Patent Assignee: HENAN NORMAL UNIVERSITY - CN110407830, 2019, A Location in patent: Paragraph 0025-0027; 0047-0049
[2]Zhao, Peizheng; Wang, Ke; Yue, Yuanyuan; Chao, Junli; Ye, Yaqing; Tang, Qinghu; Liu, Jianming [ChemCatChem, 2020, vol. 12, # 12, p. 3207 - 3211]
[3]Louillat-Habermeyer, Marie-Laure; Jin, Rongwei; Patureau, Frederic W. [Angewandte Chemie - International Edition, 2015, vol. 54, # 13, p. 4102 - 4104][Angew. Chem., 2015, vol. 127, # 13, p. 2]
[4]Yu, Jin; Moon, Hye Ran; Kim, Su Yeon; Kim, Jae Nyoung [Bulletin of the Korean Chemical Society, 2015, vol. 36, # 11, p. 2765 - 2768]

9
[ 1444-47-9 ]
[ 481075-58-5 ]
[ 92-30-8 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6128 - 6132

10
[ 13979-81-2 ]
[ 92-30-8 ]
C₂₀H₁₂Br₂F₃NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium periodate; acetic acid In dichloromethane at 40℃; for 24h; Inert atmosphere;

Reference： [1]Jin, Rongwei; Patureau, Frederic W. [Organic Letters, 2016, vol. 18, # 18, p. 4491 - 4493]

11
[ 92-30-8 ]
[ 782-17-2 ]
C₂₇H₁₆F₄N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium periodate; acetic acid In dichloromethane at 50℃; for 24h; Inert atmosphere;

Reference： [1]Jin, Rongwei; Patureau, Frederic W. [Organic Letters, 2016, vol. 18, # 18, p. 4491 - 4493]

12
[ 672-57-1 ]
[ 1204-55-3 ]
[ 92-30-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 10h;Inert atmosphere;	General procedure: To an oven-dried 25 mL ground mouth test tube equipped with a stir bar was added S-2-acetamidophenyl ethanethioate (0.5 mmol), 1-bromo-2-iodobenzene (0.6 mmol), Cs2CO3 (2.0 mmol), DMF (3 mL). The test tube was sealed with a sleeve rubber stopper and evacuated and refilled with argon for three cycles. The mixture was stirred 130 oC for 10 hours. After cooling to room temperature, the reaction mixture was quenched with water (20 mL), and extracted with ethyl acetate (20 mL) for three times. The combined organic layer was dried with anhydrous MgSO4, and condensed in vacuum on a rotary evaporator. The residual was purified on a silica gel chromatograph column by means of gradient elution (eluent: petroleum ether / ethyl acetate) to give the desired product.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 710 - 715

13
[ 92-30-8 ]
[ 1675-46-3 ]

Yield	Reaction Conditions	Operation in experiment
46.9%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 100℃; for 24h; Sealed tube; Schlenk technique; Inert atmosphere;	2 General methods of intermediates 5a-g General procedure: In a sealed tube, to a solution of the appropriate phenothiazine derivative (4a-d, 3.7mmol) in DMF (10mL) were added NaH (224.5mg, 5.6mmol) and 1,3- or 1,4-dihaloalkane (5.0mmol) at 0°C and stirred at 100°C for 24h. After the reaction was complete, the reaction mixture was extracted using ethyl acetate and water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate: n-hexane=1: 40) to yield intermediates 5a-g.

Reference： [1]Kang, Seokmin; Lee, Jung Moo; Jeon, Borami; Elkamhawy, Ahmed; Paik, Sora; Hong, Jinpyo; Oh, Soo-Jin; Paek, Sun Ha; Lee, C. Justin; Hassan, Ahmed H.E.; Kang, Sang Soo; Roh, Eun Joo [European Journal of Medicinal Chemistry, 2018, vol. 151, p. 186 - 198]

14
[ 92-30-8 ]
[ 16400-13-8 ]
7-methyl-5-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)-2,3-dihydro-1H-inden-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With oxygen; sodium nitrite In toluene at 0 - 20℃; Sealed tube;

Reference： [1]Bering, Luis; D'Ottavio, Laura; Sirvinskaite, Giedre; Antonchick, Andrey P. [Chemical Communications, 2018, vol. 54, # 92, p. 13022 - 13025]

15
[ 6940-76-7 ]
[ 92-30-8 ]
[ 1675-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(trifluoromethyl)-10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide at 0℃; for 1h;

Reference： [1]Park, Seong-Hyun; Shin, Insu; Park, Sang-Hyun; Kim, Nam Doo; Shin, Injae [Chemistry - An Asian Journal, 2019, vol. 14, # 22, p. 4035 - 4041]

16
[ 6320-02-1 ]
[ 105202-02-6 ]
[ 92-30-8 ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: 2-aminobenzenethiol (10 g, 80mmol), 3, 4-difluorobenzonitrile (11.12, 80mmol) and ferric citrate (19.59g, 80mmol) were added in DMF (50.00 mL) at 25-30 0C. The reaction mixture was heated to 110C. Reaction mixture was monitored for the synthesis of compound 3 by TLC. (2ml of reaction mixture was withdrawn and separated in ethylacetate and water. Ethyl acetate solution concentrated and crystallised in isopropyl ether to give compound 3 for characterization). After completion of reaction by TLC, powdered potassium carbonate (16.58 g, 120mmol) was added to the solution and stirred for 1 hr. The mixture was heated to 110C till completion by TLC. After completion of reaction, the mass was cooled to 25-30 C. Ethyl acetate (150 mL) and DM water (150 mL) were added. Layers separated. Organic layer washed with water (150 mL), dried over sodium sulfate and concentrated. Isopropyl ether (IPE; 150 mL) was added to the slurry, filtered, washed with IPE. Dried under vacuum at 50 C (16.84g, 94%).

Reference： [1]Letters in Organic Chemistry,2019,vol. 16,p. 16 - 24

17
[ 383-29-9 ]
[ 92-30-8 ]
bis(4-(2-(trifluoromethyl)-phenothiazine-10-yl)phenyl)sulflone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 170℃; for 12h;	2-(Trifluoromethyl)-10H-phenothiazine (2.31 g, 8.65 mmol) was dissolvedin N-methyl-2-pyrrolidone (15 mL). Bis(4-fluorophenyl)sulfone(1 g, 3.93 mmol), cesium carbonate (2.58 g, 7.93 mmol) were addedinto the mixture, and stirred under 170 C using oil bath for 12 h. Themixture was cooled to room temperature and the product was extractedusing methylene chloride. The organic layer was collected, filtered andevaporated to remove the solvent. The residue was purified by columnchromatography using n-ethylacetate/n-hexane (8:1) as an eluent,crystallized from the mixture of ethylacetate and hexane to get 1 as lightyellow crystals. FW 748.78 g/mol, yield: 1.26 g, 43%; m.p. 283-284C. 1H NMR (300 MHz, CDCl3, , ppm): 7.88 (d, J 8.1 Hz, 4H), 7.44 (d,J 8.1 Hz, 2H), 7.39-7.30 (m, 4H), 7.24-7.20 (m, 4H), 7.19-7.12 (m,6H), 7.01 (dd, J 8.1, 1.0 Hz, 2H). 13C NMR (75 MHz, CDCl3, , ppm):147.8, 141.9, 140.9, 136.1, 135.4, 129.7, 129.3, 128.7, 128.5, 127.7,126.0, 124.0, 122.2, 120.3, 119.9. MS (APCI, 20 V), m/z: 750([MH]). Elemental analysis calcd (%) for C38H22F6N2O2S3: C, 60.95;H, 2.96; F, 15.22; N, 3.74; O, 4.27; S, 12.85; Found: C, 60.99; H, 2.92; F,15.18; N, 3.79.

Reference： [1]Dyes and Pigments,2020,vol. 175

18
[ 434-64-0 ]
[ 92-30-8 ]
10-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-2-(trifluoromethyl)-10H-phenothiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 2-(trifluoromethyl)-10H-phenothiazine With potassium carbonate for 1h; Sealed tube; Stage #2: perfluorotoluene In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere;	3.2.1. General Procedure A for the Reaction of Phenothiazines with Polyfluoroarenes General procedure: Phenothiazine derivatives (1.0 mmol) and base (4.0 mmol, 4.0 eq) were placed in ascrew-capped test tube and dried under vacuum for 1 h. After backfilling with N2, solvent(10 mL) and polyfluoroarenes (2.1 mmol, 2.1 eq) were added in this order. The reactionmixture was stirred at 60 C for 24 h. The reaction was quenched with water (50 mL),and the mixture was transferred to a separatory funnel containing diethyl ether (50 mL).The organic layer was separated, and the aqueous layer was extracted with diethyl ether(2 20 mL). The combined organic fractions were washed with brine (50 mL), dried overNa2SO4, and all volatiles were removed under vacuum. The residue was purified by flashcolumn chromatography (SiO2) to yield the corresponding 10-phenylphenothiazine (PTH)derivatives.

Reference： [1]Dohi, Toshifumi; Kikushima, Kotaro; Kodama, Kazuki; Koyama, Haruka [Molecules, 2021, vol. 26, # 5]

19
[ 92-30-8 ]
[ 20440-95-3 ]
4-methyl-N-(p-tolyl)-N-(4-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)phenyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With dipotassium peroxodisulfate In acetic acid; acetonitrile at 20℃; for 24h; regioselective reaction;

Reference： [1]Lei, Aiwen; Wang, Pengjie; Wang, Shengchun; Wang, Xiaoyu; Yi, Hong; Zhang, He; Zhang, Heng [Green Chemistry, 2022, vol. 24, # 1, p. 147 - 151]

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[ CAS No. 92-30-8 ] {[proInfo.proName]}

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[ 92-30-8 ] Synthesis Path-Upstream 1~18

[ 92-30-8 ] Synthesis Path-Downstream 1~19

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Fluorinated Building Blocks

Trifluoromethyls

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Other Aromatic Heterocycles

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