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[ CAS No. 402-49-3 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Chemical Structure| 402-49-3

Chemical Structure| 402-49-3

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Quality Control of [ 402-49-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 402-49-3 ]

Product Details of [ 402-49-3 ]

CAS No. :	402-49-3	MDL No. :	MFCD00000403
Formula :	C₈H₆BrF₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IKSNDOVDVVPSMA-UHFFFAOYSA-N
M.W :	239.03	Pubchem ID :	123062
Synonyms :

Calculated chemistry of [ 402-49-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.28
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.32
Log Po/w (XLOGP3) :	3.55
Log Po/w (WLOGP) :	4.6
Log Po/w (MLOGP) :	4.12
Log Po/w (SILICOS-IT) :	3.83
Consensus Log Po/w :	3.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.8
Solubility :	0.0382 mg/ml ; 0.00016 mol/l
Class :	Soluble
Log S (Ali) :	-3.24
Solubility :	0.139 mg/ml ; 0.000582 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.55
Solubility :	0.00678 mg/ml ; 0.0000284 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.74

Safety of [ 402-49-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 402-49-3 ]

* 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 [ 402-49-3 ]
Downstream synthetic route of [ 402-49-3 ]

[ 402-49-3 ] Synthesis Path-Upstream 1~13

1
[ 349-95-1 ]
[ 402-49-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3389 - 3395
[2] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[3] Journal of the American Chemical Society, 1983, vol. 105, # 5, p. 1221 - 1227
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 1767,1768, 3482, 3485
[5] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[6] Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 2091 - 2095[7] Zhurnal Organicheskoi Khimii, 1970, vol. 6, p. 2085 - 2090
[8] Journal of Medicinal Chemistry, 1971, vol. 14, p. 862 - 866
[9] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253
[10] Tetrahedron, 1984, vol. 40, # 10, p. 1863 - 1868
[11] Journal of Organic Chemistry, 1981, vol. 46, # 21, p. 4247 - 4252
[12] Tetrahedron, 1997, vol. 53, # 24, p. 8211 - 8224
[13] Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 556 - 568
[14] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6842 - 6846
[15] Patent: US5554620, 1996, A,
[16] Organic and Biomolecular Chemistry, 2015, vol. 13, # 40, p. 10136 - 10149
[17] Chemical Biology and Drug Design, 2016, p. 97 - 109
[18] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 100 - 114

2
[ 455-24-3 ]
[ 402-49-3 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 18, p. 4842 - 4845,4
[2] Journal of the American Chemical Society, 1983, vol. 105, # 5, p. 1221 - 1227
[3] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[4] Synthesis (Germany), 2013, vol. 45, # 23, p. 3233 - 3238

3
[ 583-02-8 ]
[ 402-49-3 ]

Reference： [1] Journal of the American Chemical Society, 1983, vol. 105, # 5, p. 1221 - 1227
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 1767,1768, 3482, 3485
[3] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132

4
[ 6140-17-6 ]
[ 402-49-3 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 49, p. 6530 - 6533
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 15, p. 6622 - 6637
[3] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 711 - 719[4] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 4, p. 788 - 797
[5] European Journal of Organic Chemistry, 2009, # 36, p. 6328 - 6335

5
[ 329-15-7 ]
[ 402-49-3 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1767,1768, 3482, 3485
[2] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[3] Patent: US5554620, 1996, A,

6
[ 455-19-6 ]
[ 402-49-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6842 - 6846
[2] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 100 - 114

7
[ 774197-61-4 ]
[ 6140-17-6 ]
[ 402-49-3 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 19, p. 3353 - 3356

8
[ 402-51-7 ]
[ 402-49-3 ]

Reference： [1] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253

9
[ 402-49-3 ]
[ 2338-75-2 ]

Reference： [1] Patent: US5502054, 1996, A,
[2] Patent: US5622954, 1997, A,

10
[ 143-33-9 ]
[ 402-49-3 ]
[ 2338-75-2 ]

Reference： [1] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[2] Journal of Organic Chemistry, 1981, vol. 46, # 21, p. 4247 - 4252

11
[ 151-50-8 ]
[ 402-49-3 ]
[ 2338-75-2 ]

Reference： [1] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253

12
[ 402-49-3 ]
[ 775-00-8 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 21, p. 4247 - 4252
[2] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132

13
[ 402-49-3 ]
[ 74-89-5 ]
[ 90390-11-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2882 - 2891

[ 402-49-3 ] Synthesis Path-Downstream 1~68

1
[ 6140-17-6 ]
[ 402-49-3 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 6530 - 6533
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 6622 - 6637
[3]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 711 - 719
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 788 - 797
[4]European Journal of Organic Chemistry,2009,p. 6328 - 6335

3
[ 13438-65-8 ]
[ 402-49-3 ]
2-Imino-1-(4-trifluoromethyl-benzyl)-1,2-dihydro-pyridine-3-carboxylic acid amide; hydrobromide [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1009 - 1015

4
[ 7418-66-8 ]
[ 402-49-3 ]
4-Imino-1-(4-trifluoromethyl-benzyl)-1,4-dihydro-pyridine-3-carboxylic acid amide; hydrobromide [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1009 - 1015

5
[ 1873-77-4 ]
[ 622-95-7 ]
[ 402-49-3 ]
[ 6140-17-6 ]
[ 106-43-4 ]
[ 5089-31-6 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 8479 - 8490

6
[ 402-49-3 ]
[ 18672-03-2 ]
5,6-Dichloro-1-(4-trifluoromethyl-benzyl)-1H-benzoimidazol-2-ylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1252 - 1262

7
[ 402-49-3 ]
[ 74-89-5 ]
[ 90390-11-7 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2882 - 2891

8
[ 31374-18-2 ]
[ 402-49-3 ]
7-chloro-3-(4-trifluoromethyl-benzyl)-3<i>H</i>-quinazolin-4-one [ No CAS ]

Reference： [1]Revue Roumaine de Chimie,1999,vol. 44,p. 341 - 350

9
[ 144978-12-1 ]
[ 402-49-3 ]
(2R,4S)-5-Oxo-4-(4-trifluoromethyl-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4559 - 4570

10
[ 774197-61-4 ]
[ 6140-17-6 ]
[ 402-49-3 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3353 - 3356

11
[ 64318-28-1 ]
[ 402-49-3 ]
[ 788824-77-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In acetone; for 4h;Reflux;	General procedure: To a N-Boc-tyramine dissolved in acetone was added benzyl bromide derivative and potassium carbonate. The reaction mixture was refluxed at 50-60 C for 4 h. After the reaction, the reaction mixture was filtered, and filtered solution was evaporated in vacuo. The product residue was purified by column chromatography. Using Method C, N-Boc-tyramine (0.50 g, 2.1 mmol), 4-(trifluoromethyl)benzyl bromide (0.60 g, 2.5 mmol), and potassium carbonate (1.17 g, 8.4 mmol) gave 11c as a white solid (0.85 g, 100%): Rf = 0.38 (EtOAc 1: n-Hexane 3): 1H NMR (DMSO-d6, 400 MHz) d 1.35 (s, C(CH3)3), 2.61 (t, J = 7.5 Hz, NHCH2CH2), 3.08 (q, J = 7.9 Hz, NHCH2CH2), 5.19 (s, OCH2), 6.85 (t, J = 5.4 Hz, 1 ArH), 6.91-6.96 (m, 2 ArH), 7.08-7.14 (m, 2 ArH), 7.63-7.78 (m, 4 ArH); 13C NMR (DMSO-d6, 100 MHz) d 28.2 (C(CH3)3), 34.2 (NHCH2CH2), 41.7 (NHCH2CH2), 68.2 (OCH2), 77.4 (C(CH3)3), 114.7, 124.2 (q, JC-F = 270.2 Hz), 125.3, 127.9, 128.2 (q, JC-F = 31.4 Hz), 129.6, 131.9, 142.2, 155.5 (13 ArC), 156.4 (C(O)C(CH3)3).

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 232 - 244
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 1101 - 1112

12
[ 3034-62-6 ]
[ 402-49-3 ]
1-[4-(trifluoromethyl)benzyl]-2-iodo-1H-imidazole [ No CAS ]

Reference： [1]Synthesis,2007,p. 529 - 540

13
[ 40928-13-0 ]
[ 402-49-3 ]
C₆H₃C₂O₃NClCH₂C₆H₄CF₃ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 7058 - 7061

14
[ 402-49-3 ]
[ 67531-86-6 ]
[ 946134-83-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3624 - 3629

15
[ 583-02-8 ]
[ 402-49-3 ]

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 1221 - 1227
[2]Journal of the American Chemical Society,1949,vol. 71,p. 1767,1768, 3482, 3485
[3]Canadian Journal of Chemistry,1970,vol. 48,p. 125 - 132

16
[ 402-49-3 ]
[ 775-00-8 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 4247 - 4252
[2]Canadian Journal of Chemistry,1970,vol. 48,p. 125 - 132

17
[ 4383-06-6 ]
[ 402-49-3 ]
[ 613240-66-7 ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-trifluoromethyl-benzene and 5-hydroxymethyl-2-methoxy-phenol. MS m/z 295 (M-OH).

Reference： [1]Patent: US2003/225158,2003,A1 .Location in patent: Page 67

Yield	Reaction Conditions	Operation in experiment
	With piperidine; Carbonyldiimidazole; tin-2-ethylhexanoate dihydrate; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; dibromotriphenylphosphorane; In DMF (N,N-dimethyl-formamide); dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane;Combinatorial reaction / High throughput screening (HTS);	EXAMPLE 1 [0213] This example shows the synthesis of a combinatorial library of thioquinazolinone derivatives. [0214] Step 1a: Preparation of Wang Bromide Resin [0215] 40 tea bags containing 2 g each of Wang resin (80 g, 120 mmol) was taken in a 5 L PP container. A solution of triphenylphosphine dibromide (152 g, 0.15 M, 3 eq., 360 mmol) in 2000 ml DCM was added and the solution was shaken at room temperature overnight. The resin was sequentially washed with DCM (4×, 1.5 L each) and diethylether (6×, 1.5 L each) and dried under vacuum, to give the bromo wang resin. [0216] Step 1b: Loading of the Nitrophenol on Bromo Wang [0217] 20 g of the Bromo wang resin (1.5 meq/g) was taken in a 2 L wide-mouthed glass container and 1000 mL DMA was addded to it followed by the addition of the nitro phenol (10 eq., 0.3M, 300 mmol). Potasium t-butoxide (33.46 g, 10 eq., 300 mmol) was then added to it and the bottles were heated at 50 C. overnight. The bags were washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The tea bags were then dried overnight in air. The following nitrophenols were used: [0218] 2-METHYL-5-NITROPHENOL [0219] 5-HYDROXY-2-NITROBENZOTRIFLUORIDE [0220] 3-METHYL-4-NITROPHENOL [0221] 2-METHOXY-5-NITROPHENOL [0222] M-NITROPHENOL [0223] Step 1c: Reduction of the Nitro Group to Amine [0224] A 2.0 M solution of tin-2-ethylhexanoate dihydrate was prepared in DMF containing 0.5% H2O. The tea bags were added and the solution is heated at 50 C. for 40 hours. After cooling the bags are washed with DMF/10% HOAc (3×), DMF (3×), 5% DIEA/DCM (2×), DCM (2×) and MeOH (2×) and dried in air overnight. [0225] Step 1d: Coupling N-FMOC Protected Amino Acid to Wang Resin. [0226] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL plastic bottle. DMF (300 mL), DCM (300 mL), FMOC-Cyclohexyl alanine (70.82 g, 6 eq., 0.3M, 180 mmol), DIC (22.71 g, 6 eq., 180 mmol), HOBt (24.32 g, 6 eq., 180 mmol) were added sequentially. After shaking for 12 hours, the packet was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried overnight in air. The tea bags containing the amino acids were then treated with 20% piperidine/DMF for 2 h at room temperature to deblock the FMOC group. The following amino acids were used: [0227] FMOC-GLY-OH [0228] FMOC-ALA-OH [0229] FMOC-L-ISOLEUCINE [0230] FMOC-L-PHENYLALANINE [0231] FMOC-D-NLE-OH [0232] FMOC-CHA-OH [0233] FMOC-L-TRYPTOPHAN [0234] Step 1e: Coupling of the Diamines to Wang Resin [0235] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL Nalgene bottle. 600 mL of DCM was added followed by the addition of the carbonyl diimidazole (29.9 g, 6 eq., 0.3M, 180 mmol) and the flasks were shaken at room temperature for 3 hours after which they were decanted and washed with DCM (2×, 600 mL). To these Nalgene bottles were added the diamines (6 eq., 0.4M, 180 mmol) in 450 mL of DCM (0.4M) and they were shaken at room temperature overnight. The diamines used were as follows: [0236] 2,2-DIMETHYL-1,3-PROPANEDIAMINE [0237] 1,3-CYCLOHEXANEDIAMINE [0238] (1R,2R)-(-)-1,2-DIAMINOCYCLOHEXANE [0239] TRANS-1,4-DIAMINOCYCLOHEXANE [0240] P-XYLYLENEDIAMINE [0241] 1,4-BIS(3-AMINOPROPYL)PIPERAZINE [0242] ETHYLENEDIAMINE [0243] 1,3-DIAMINOPROPANE [0244] 1,8-DIAMINO-3,6-DIOXAOCTANE [0245] 1,4-DIAMINOBUTANE [0246] 1,5-DIAMINOPENTANE [0247] 1,6-HEXANEDIAMINE [0248] N,N-BIS(3-AMINOPROPYL)METHYLAMINE [0249] 2,2'-THIOBIS(ETHYLAMINE) [0250] 2,5-DIMETHYL-1,4-PHENYLENEDIAMINE [0251] After shaking overnight, the packets was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried in air. [0252] Step 2: Formation of the Isothiocyanate [0253] The o-amino benzoate ester (136 g, 10 eq., 900 mmol) was taken in a 5 L wide-mouthed glass bottle and 2.7 L of dichloroethane was added to it (0.3M). The following esters were used: [0254] METHYL ANTHRANILATE [0255] METHYL 2-AMINO-4-CHLOROBENZOATE [0256] 2-AMINO-4,5-DIMETHOXYBENZOIC ACID [0257] METHYL ESTER [0258] METHYL 3,4,5-TRIMETHOXYANTHRANILATE [0259] DIMETHYL AMINOTEREPHTHALATE [0260] METHYL 2-AMINO-5-BROMOBENZOATE [0261] METHYL 3-AMINOTHIOPHENE-2-CARBOXYLATE [0262] METHYL 3-AMINO-5-PHENYLTHIOPHENE-2-CARBOXYLATE [0263] Thiocarbonyl diimidazole (160 g, 10 eq., 900 mmol) was added to it and the solution was heated at 55 C. overnight to form the isothiocyanate. [0264] Step 3: Formation of the Thioquinazolinone [0265] The next day the tea bags containing the amino acids, diamines and the amino phenols on wang resin (90 mmol) was added to the isothiocyanate solution from reaction 2 and the glass bottles were heated at 55 C. overnight. After cooling the bags was washed alternatively with DMF (2000 mL) and DCM (2000 mL) 3 cycles followed by 6 cycles of MeOH...

Reference： [1]Patent: US2004/102629,2004,A1 .Location in patent: Page 16-18

19
[ 618-49-5 ]
[ 402-49-3 ]
NU 1036 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; acetonitrile;	EXAMPLE 8 3-(4-Trifluoromethylbenzyloxy)benzamide (Compound NU1036) <strong>[618-49-5]3-hydroxybenzamide</strong> (0.137 g; 1 mmol) was dissolved in anhydrous acetonitrile (20 ml) under a nitrogen atmosphere. To this was added potassium carbonate (0.138 g; 1 mmol) and 4-(trifluoromethyl)benzyl bromide (0.155 ml; 1 mmol). This mixture was left to reflux for 17 hours. The reaction was followed by TLC. Upon completion the acetonitrile was removed under reduced pressure to leave a white solid which was dissolved in water. The organics were extracted into dichloromethane (3*30 ml), dried over magnesium sulphate, filtered and the solvent removed under reduced pressure to leave a white crystalline solid which was recrystallized from boiling ethyl acetate and petrol (60-80). M/Z (EI): 295 (35%; M+) 159 (100%)

Reference： [1]Patent: US5756510,1998,A

20
[ 80866-82-6 ]
[ 402-49-3 ]
4-bromo-1-methoxy-2-([4-(trifluoromethyl)benzyl]oxy}methyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; water;	Production Example 26b) 0.8 g of 5-bromo-2-methoxyphenyl methanol was dissolved in 30 ml tetrahydrofuran. 2.6 g of 4- (trifluoromethyl)benzyl bromide and 0.22 g of sodium hydride (60 % oily) were added thereto, followed by stirring at room temperature for 16 hours. Water was added to the reaction solution, followed by extracting with diethyl ether. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, to give 1.4 g of 4-bromo-1-methoxy-2-([4-(trifluoromethyl)benzyl]oxy}methyl)benzene from fractions eluted with hexane-ethyl acetate (9:1). 1H-NMR(CDCl3) delta: 3.80 (s, 3H) 4.57 (s, 2H) 4.64 (s, 2H) 6.77 (d, J=8.0Hz, 1H) 7.37 (dd, J=2.0, 8.0Hz, 1H) 7.50 (d, J=8.0Hz, 2H) 7.52 (d, J=2.0Hz, 1H) 7.61 (d, J=8.0Hz, 2H)

Reference： [1]Patent: EP1216980,2002,A1

21
[ 350-29-8 ]
[ 402-49-3 ]
[ 636795-20-5 ]

Yield	Reaction Conditions	Operation in experiment
69%		a 3-Fluoro-4-(4-trifluoromethyl-benzyloxy)-benzoic Acid 4-Trifluoromethyl-benzyl Ester As described for example 18a, <strong>[350-29-8]3-fluoro-4-hydroxybenzoic acid</strong> (2.5 g, 16 mmol) [using 4-(trifluoromethyl)-benzyl bromide instead of 4-fluorobenzyl bromide] was converted to the title compound (5.3 g, 69percent) which was obtained as a white solid. MS: m/e=472.1 (M+).

Reference： [1]Patent: US2003/236304,2003,A1

22
[ 93247-78-0 ]
[ 402-49-3 ]
[ 1050656-28-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of lH-Indole-7-carboxylic acid methyl ester 1 (209.8 g, 1.20 mole) in DMF (1.4 L) at 9 0C was added KOtBu (161.6 g, 1.44 mole) portion wise (temperature rose to 15 0C). The cold bath was removed and the reaction mixture was stirred at r.t. for 2 hours. The reaction mixture was cooled to 10 0C and a solution of l-bromomethyl-4-trifluoromethyl-benzene 2 (343.7g, 1.44 mole) in DMF (400 mL) was added over 2.5 hours and the flask was rinsed with DMF (100 mL). H2O (1.9 L) was added at 15 0C in order to precipitate the product. The slurry was filtered and rinsed with H2O (4 X IL) and the product dried under a flow of N2 under vacuum. 411.1 g of material was obtained at 82 A%. A sample was purified by chromatography : 1H NMR (500 MHz, Acetone-/) delta 7.88 (dd, J = 7.8, 1.1 Hz, IH), 7.60 (d, J = 8.2 Hz, IH), 7.58 (d, J = 3.2 Hz, IH), 7.53 (dd, J= 7.5, 1.1 Hz, IH), 7.13 (X, J = 7.6 Hz, IH), 7.07 (d, J = 8.0 Hz, IH), 6.74 (d, J = 3.2 Hz, IH), 5.83 (s, 2H), 3.72 (s, 3H); 19F NMR (377 MHz, Acetone-afe) delta - 62.4; 13C NMR (100 MHz, Acetone-tf6) delta 167.7, 143.8, 132.8, 132.7, 132.2, 128.9 (q, J= 32 Hz), 127.3, 126.0, 125.5 (m), 124.9, 123.3, 119.0, 117.4, 102.8, 52.2, 51.8; IR (CDCl3) 3112, 3076, 3038, 2987, 2949, 2844, 1925, 1716, 1619, 1524, 1448, 1421, 1321, 1275, 1161, 1134, 1113, 1067, 1017, 844, 749, 731cm"1; HRMS-ESI (m / z): [M+H]+ calcd for Ci8H14F3NO2, 334.10494; found 334.10548
	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃;	EXAMPLE 34- { 1 -[( { 1 - [4-(trifluoromethyl)benzyl] - 1 H-indol-7-yl } carbonyl)amino]cyclopropyl } benzoic acidStep 1 : Methyl l-[4-(trifluoromethyl)benzyl]-lH-indole-7-carboxylateMethyl lH-indole-7-carboxylate (47.8 g, 273 mmol) and l-(bromomethyl)-4- (trifluoromethyl)benzene (81 g, 341 mmol) were dissolved in DMF (1.3 L) at O0C. 60% w/w NaH (12 g, 300 mmol) was added portion wise. The ice bath was removed and the mixture stirred at O0C for 3 hours, then overnight at RT. The reaction mixture was quenched with 3 L of NH4Cl(sat.) and the aqueous layer was extracted 3 times with 1 L of ether. The organic layers were combined, washed with water and brine. The compound was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d): delta 8.90 (d, IH), 7.70 (s, IH), 7.60 (d, 2H), 7.40 (d, IH), 7.10 (t, IH), 7.00 (d, 2H), 6.70 (d, IH), 5.70 (s, 2H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3760 - 3763
[2]Patent: WO2010/121382,2010,A1 .Location in patent: Page/Page column 9; 10
[3]Patent: WO2008/104055,2008,A1 .Location in patent: Page/Page column 28

23
[ 402-49-3 ]
[ 408355-23-7 ]
[ 1050656-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at -10℃; for 1.08333h;	Step 2: 7-bromo-5-fluoro-l-[4-(trifluoromethyl)benzyl]-l//-indole7-bromo-5-fiuoro-lH-indole (900mg, 4.20mmol) and l-(bromomethyl)-4- (trifluoromethyl)benzene (1.6g, 6.7mmol) were dissolved in DMF (20 ml). The mixture was cooled to -100C and NaH (185 mg, 4.6 mmol) was added portion wise over 5 min. The mixture was stirred for 1 hour at this temperature. Quenched with NH4Cl (1/2 sat.) and IN HCl. The mixture was diluted with water and the aqueous phase was extracted 3x with ether. The combined organic layers were washed with 3x water, Ix brine and dried over MgSO4. The product was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): delta 7.70 (m, 3H), 7.45 (dd, IH), 7.25 (dd, IH), 7.10 (d, 2H), 6.65 (d, IH), 5.90 (s, 2H).

Reference： [1]Patent: WO2008/104055,2008,A1 .Location in patent: Page/Page column 32

24
[ 402-49-3 ]
[ 485-71-2 ]
[ 101311-12-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran;Reflux;	General procedure: The phase-transfer catalysts (C1-C11) were synthesized according to the proceduresbelow. To a solution of cinchonidine (1.00 g, 3.4 mmol) in THF (50 mL) was addedthe aryl benzyl bromides (3.4 mmol). The mixture was heated for 6-8 h at reflux.After cooling to room temperature, the mixture was poured into MTBE (150 mL)under stirring. The precipitated solid was filtrated and recrystallized fromCH3OH/MTBE to afford C1-C11

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 1421 - 1427
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 3238 - 3241

25
[ 39824-26-5 ]
[ 402-49-3 ]
6-chloro-9-((3aR,4R,6R,6aR)-2,2-dimethyl-6-(((4-(trifluoromethyl)benzyl)oxy)methyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1510 - 1513
[2]Chemical Communications,2017,vol. 53,p. 5167 - 5170

26
[ 1640-39-7 ]
[ 17028-61-4 ]
[ 402-49-3 ]
[ 1039745-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane-CH2Cl2; ethanol; dichloromethane; toluene;	1-(4'-trifluoromethyl-benzyl)-3,3-dimethyl-2-methylene-indoline A solution of 2,3,3-trimethylindolenine (3 g, 12.3 mmol) and 4-(trifluoromethyl)benzyl bromide (2.35 g, 14.8 mmol) was stirred under nitrogen in 20 ml toluene for 24 h at 90 C. The mixture was cooled to room temperature, evaporated under reduced pressure, a residue was dissolved in CH2Cl2 and treated with NaOH(aq) 5% for 45 min. The organic phase was separated, dried over Na2SO4, chromatographed through a short alumina column in hexane-CH2Cl2 (1:1). The solvent was evaporated (cooling under nitrogen), giving rise to 151(2.9 g, 9.1 mmol), as a free base which was immediately dissolved in 45 ml ethanol containing a few drops of Et3N. 3-methoxy-5-nitrosalicylaldehyde (1.8 g, 9.1 mmol) was added to the solution and the reaction mixture was refluxed for 50 min. The reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure, a residue was chromatographed on a short alumina column, eluent: hexane-CH2Cl2 (10-40%). The product was crystallized from ether-hexane, dried in vacuo. Yield 1.35 g, 19.7%

Reference： [1]Patent: US2010/34961,2010,A1

27
[ 402-49-3 ]
[ 3060-50-2 ]
[ 1204177-05-8 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 316 - 319

28
[ 402-49-3 ]
[ 939-69-5 ]
[ 676460-22-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 15h;Reflux;	6-(4-Trifluoromethylbenzyloxy)-2-cyanobenzothiazole: A suspension of <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong> (1.0 g, 5.68 mmol) in acetone (5 mL) was prepared in a 100-mL 2-necked round-bottomed flask fitted with a reflux condenser. Anhydrous potassium carbonate (0.94 g, 6.82 mmol) was added to the reaction mixture and the suspension turned to a yellow solution. Then 4-(trifluoromethyl)benzyl bromide (1.49 g, 6.25 mmol) was added and the reaction mixture was heated at reflux for 15 h using a heated stir plate and oil bath. The reaction mixture was allowed to cool to ambient temperature and then filtered to remove inorganic salts. The filtrate was concentrated by rotoevaporation to provide 1.7 g (89percent yield) of an off-white solid that was used without purification. The structure was confirmed by 1H NMR analysis in DMSO-d6

Reference： [1]Patent: US7692022,2010,B2 .Location in patent: Page/Page column 36

29
[ 22300-52-3 ]
[ 402-49-3 ]
[ 1248676-30-3 ]
[ 1248676-65-4 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4632 - 4635

30
[ 1004-40-6 ]
[ 402-49-3 ]
[ 1094534-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water; at 20 - 50℃; for 17h;	General procedure: In 2-dram vials (round bottom, 15x75 mm) containing substituted alkyl or benzyl bromides (0.800 mmol) was added 0.5 mL of EtOH via a syringe. The stock solution containing 6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (0.500 mmol) and 3.45 M aqueous solution of NaOH (0.800 mmol) in EtOH was prepared as followed. In a 250 mL round-bottom flask was added 4.82 g of 6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one, 69.6 mL of EtOH, 20 mL of water, and 10.4 mL of 3.25 M aqueous solution of NaOH. This mixture was stirred at rt until a homogenous solution was formed. 2.50 mL of this stock solution was dispensed into each 2-dram vial.The vials were capped and heated to 50 C in a shaker. After 17 h, LCMSs were randomly taken from different reactions and all showed product formation cleanly. All vials were placed in a Genevac to remove the solvents and the product was purified by mass-directed high throughput purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1055 - 1060

31
[ 402-49-3 ]
[ 68-41-7 ]
C₁₁H₁₁F₃N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-<strong>[68-41-7]cycloserine</strong>, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-<strong>[68-41-7]cycloserine</strong> were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2564 - 2567

32
[ 402-49-3 ]
[ 82337-58-4 ]
[ 3832-75-5 ]

Reference： [1]Patent: WO2012/109164,2012,A1

33
[ 402-49-3 ]
[ 142643-29-6 ]
[ 1093396-77-0 ]

Reference： [1]Patent: WO2008/156715,2008,A1

34
[ 402-49-3 ]
[ 142643-29-6 ]
[ 1093396-78-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; at 70℃; for 0.5h;	To a mixture of 830 mg of potassium carbonate in 50 ml of methanol was added ter t-butyl (piperidin-3 -ylmethyl)carbamate (643 mg), followed by l-(bromomethyl)-4- (trifluoromethyl)benzene (717 mg). The mixture was heated to 7O0C and stirred for 0.5 h. The sample was filtered through a small plug of silica gel and concentrated in vacuo to provide tert- butyl({ l-[4-(trifluoromethyl)benzyl]piperidin-3-yl}methyl)carbamate (640 mg). To a solution of this protected amine in 10 ml of dichloromethane was added trifluoroacetic acid (5 ml). The mixture was stirred at 7O0C for 1.5 h, and then concentrated in vacuo. The residue was diluted with 30 ml of ethyl acetate and basified by slow and cautious addition of 30 ml of a saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated and extracted once with 30 ml of ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound (418 mg, 89%). Mass spectrum (ESI) 273.2 (M+l).

Reference： [1]Patent: WO2008/156715,2008,A1 .Location in patent: Page/Page column 57

35
[ 96293-19-5 ]
[ 402-49-3 ]
C₃₅H₃₀F₃N₃NiO₃ [ No CAS ]
{N-{phenyl{2-{[(1R,2S)-1-(phenylmethyl)pyrrolidin-2-yl-kN]carbonyl}amino-kN}phenyl}methylene}-4-(trifluoromethyl)-L-phenylalaninato(2 )-kN,kO}nickel [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 2672 - 2679

36
[ 402-49-3 ]
[ 25163-98-8 ]
4-isobutyl-2-phenyl-4-[4-(trifluoromethyl)benzyl]oxazol-5(4H)-one [ No CAS ]

Reference： [1]Synlett,2013,vol. 24,p. 701 - 704

37
[ 4294-57-9 ]
[ 402-49-3 ]
[ 613-33-2 ]
[ 538-39-6 ]
[ 170789-13-6 ]

Yield	Reaction Conditions	Operation in experiment
76%Chromat.	With FeCl(THF)L1; In diethyl ether; at 20℃; for 0.5h;Schlenk technique; Inert atmosphere;Catalytic behavior;	General procedure: [00283] Catalyst 20 (0.10 mmol) in CH2C12 (3 mL) was added to a 30 mL Schlenk flask and the solvent removed in vacuo. Et20 (5 mL) and the alkyl halide (2.0 mmol) were added to the catalyst under dry nitrogen. A solution of Grignard reagent (4.0 mmol) was added dropwise under vigorous stirring. The resulting mixture was stirred at roomtemperature for 30 min and the reaction was quenched with HC1 (2.0 M, 5 mL). The organic phase was extracted with Et20 (5 mL) and dried over MgSC>4. The organic phase was then passed through a plug of silica and the diethyl ether was removed in vacuo. The resulting products were then analyzed by GC-MS (using dodecane as internal standard) and NMR spectroscopy (using acetophenone as internal standard).

Reference： [1]Patent: WO2013/53046,2013,A1 .Location in patent: Paragraph 00282; 00283; 00285

38
[ 38427-94-0 ]
[ 402-49-3 ]
[ 1445435-59-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3476 - 3479

39
[ 15297-33-3 ]
[ 402-49-3 ]
(R)-N-methyl-1-(naphthalen-1-yl)-N-(4-(trifluoromethyl)benzyl)ethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 2h;Reflux; Inert atmosphere;	General procedure: N-Methyl-1-(naphthalen-1-yl)ethanamine (8) (0.37g, 2.00mmol), N,N-diisopropylethylamine (0.39g, 3.02mmol), 1-(bromomethyl)-4-tert-butylbenzene (0.50g, 2.20mmol) and acetonitrile (5mL) were mixed and stirred at reflux under an N2-atmosphere for 2h. The solvent was then removed at reduced pressure and CH2Cl2 (5mL) was added. The dichloromethane phase was washed with water (5mL) and the water phase was back extracted with CH2Cl2 (3×5mL). The combined organic fractions were dried over Na2SO4, and concentrated in vacuum. The crude product was purified by silica-gel column chromatography. Alternatively, the purification was done by filtration through a short silica-gel column (pentane:EtOAc, 9:1), followed by precipitation as it hydrochloride salt by addition of HCl saturated ether. The solid material was washed with cold pentane. Alternatively, using 8·HCl the reaction was run similarly, but employing a 3-fold excess of N,N-diisopropylethylamine.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 68,p. 482 - 496

40
[ 60481-36-9 ]
[ 402-49-3 ]
1-(3,5-dimethylphenyl)-1-(4-(trifluoromethyl)benzyl)hydrazine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 5202 - 5205
Angew. Chem.,2014,vol. 126,p. 5303 - 5306,4

41
[ 590418-08-9 ]
[ 402-49-3 ]
[ 1627143-97-8 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 4404 - 4407
Angew. Chem.,2014,vol. 126,p. 4493 - 4496,4

42
[ 402-49-3 ]
[ 321574-29-2 ]

Reference： [1]Patent: WO2014/192023,2014,A1
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3064 - 3066

43
[ 3920-50-1 ]
[ 402-49-3 ]
1-(4-(trifluoromethyl)benzyl)-1H-pyrazole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With potassium carbonate; In acetonitrile; at 20℃;	General procedure: A mixture of 1H-imidazole-2-carbaldehyde 40 (200 mg, 2.08 mmol), potassium carbonate (0.8630 g, 6.24 mmol) and 3-(bromomethyl)-1,1'-biphenyl 38 (0.7716 g, 3.12 mmol) in acetonitrile (10 mL) was stirred overnight at room temperature, then the solvent was removed, diluted with water, and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 44 as a pale yellow solid (527 mg, 97percent).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 86,p. 639 - 652

44
[ 1303587-99-6 ]
[ 402-49-3 ]
2-chloro-8-(4-(trifluoromethyl)benzyl)-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0℃; for 0.5h;Inert atmosphere;	Synthesis of2-chloro-8-(4-(trifluoromethyl) benzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] [0459] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (3 mL) under argon atmosphere were added sodium hydride (42 mg, 1.75 mmol) and l-(bromomethyl)-4-(trifluoromethyl) benzene (251 mg, 1.05 mmol) at 0 C. The reaction mixture was stirred for 30 min at 0 C. After consumption of the starting materials (monitored by TLC), the reaction was quenched with cold water (20 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine (5 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was washed with n-pentane (2 x 5 mL) to afford 2-chloro-8-(4-(trifluoromethyl) benzyl)-7, 8- dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (220 mg, 76%) as an off-white solid. 1H-NMR (OMSO-d6, 500 MHz): delta 7.76 (s, 1H), 7.74 (d, 2H), 7.52 (d, 2H), 4.89 (s, 2H), 4.23-4.20 (m, 2H), 3.57-3.54 (m, 2H); LCMS: 329.8 (M+l); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.88 min 0.05% Aq TFA: ACN; 0.80 mL/min); UPLC (purity): 90.0%; (column; Acquity UPLC BEH C-18 2.1 X 50 mm, 1.7 mupiiota); RT 2.58 min. ACN: 0.025% Aq TFA; 0.5 mL/min; TLC: 30% EtOAc/hexane (R 0.4).

Reference： [1]Patent: WO2015/66697,2015,A1 .Location in patent: Paragraph 0459

45
[ 402-49-3 ]
[ 6140-17-6 ]

Reference： [1]Chemical Science,2015,vol. 6,p. 3434 - 3439
[2]Chemical Communications,2019,vol. 55,p. 7247 - 7250

46
[ 442-51-3 ]
[ 402-49-3 ]
7-methoxy-1-methyl-9-[[4-(triuoromethyl)phenyl]methyl]-pyrido[3,4-b]indole [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 53809 - 53818

47
[ 402-49-3 ]
[ 288-36-8 ]
[ 63778-04-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 7146 - 7148

48
[ 40598-94-5 ]
[ 402-49-3 ]
3-bromo-1-(4-(trifluoromethyl)benzyl)-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		[0164] A mixture of KOH (1.12 g, 20 mmol) in DMSO (50 mL) was stirred at room temperature for 5 min. 3-bromo-lH-indazole (1.97 g, 10 mmol) was then added in one portion. The resulting mixture was stirred at room temperature for 5 min. A solution of 1- (bromomethyl)-4-(trifluoromethyl)benzene (3.6 g, 15 mmol) in DMSO (5 mL) was then added dropwise over 10 min. When the addition was complete, the resulting mixture was stirred at room temperature for an additional 1 h. The mixture was quenched by the addition of water (200 mL). The mixture was then extracted with CH2C12 (3 X 100 mL). The combined extracts were washed with () (2 X 100 mL), brine (1 X 100 mL), then dried over MgS0 , filtered and concentrated in vacuo. Purification by flash chromatography (0553) (Silica, 200g, 10 - 100% EtOAc/Hexanes) gave 3-Bromo-l-(4-(trifluoromethyl)benzyl)-lH- indazole (3.1 g, 8.7 mmol, 87 % yield) as an off-white crystalline solid. MS (ESI) m/z: (0554) 355and 357 (Mu+Eta)+·

Reference： [1]Patent: WO2015/127125,2015,A1 .Location in patent: Paragraph 0164

49
[ 40598-94-5 ]
[ 402-49-3 ]
3-phenyl-1-(4-(trifluoromethyl)benzyl)-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2015/127125,2015,A1

50
[ 22818-40-2 ]
[ 402-49-3 ]
[4-(4-trifluoromethyl)benzyloxy]-D-phenylglycine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9354 - 9370

51
[ 1105187-36-7 ]
[ 402-49-3 ]
3-bromo-4-(4-trifluoromethylbenzyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4 g	With caesium carbonate; at 20℃; for 14.0h;	A solution of 3-Bromo-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-S-carboxylic acid methyl ester (2.3 g), 4-trifluoromethybenzyl bromide (2.4 g) and Cs2CO3 (4 g) was stirred for 14 h at room temperature. The reaction mixture was then diluted with 100 ml of 1:1 hexane/EtOAc and filtered through a pad of silica gel. The filtrate was concentrated to give 4.0 g of the crude title compound which was used for the next step without further purification.

Reference： [1]Patent: EP2320906,2016,B1 .Location in patent: Paragraph 0142; 0143

52
[ 42726-73-8 ]
[ 402-49-3 ]
1-tert-butyl 3-methyl 2-benzoyloxy-2-(4-trifluoromethylbenzyl)malonate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5484 - 5487

53
[ 42726-73-8 ]
[ 402-49-3 ]
1-tert-butyl 3-methyl 2-(4-trifluoromethylbenzyl)malonate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5484 - 5487

54
[ 185613-91-6 ]
[ 402-49-3 ]
4-(benzo[d][1,3]dioxol-5-yl)-N-(4-(trifluoromethyl)benzyl)thiazole-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%		General procedure: A solution of <strong>[185613-91-6]4-(benzo[d][1,3]dioxol-5-yl)thiazol-2-amine</strong> (1.0 equiv) and NaH (1.5 equiv) in THF was stirred at room temperature. After 1 h, benzyl bromide (1.5 equiv) was added and stirring was continued for 10 more min. The reaction progress was monitored by TLC. After completion of the reaction, quenched with saturated NH4Cl solution and extracted with EtOAc, the organic layer was dried over MgSO4, filtered, concentrated invacuo. The residue was purified by silica gel column chromatography (16% EtOAc/hexanes) to afford desired product.
16.7%		4-(Benzo[d] [1,3]dioxol-5-yl)thiazol-2-amine(2) (1.00 g, 4.54 mmol) and NaH (0.164 g, 6.82 mmol) to THF (15 ml) todissolved and then allowed to react at room temperature for 1 hour under a nitrogen stream. Then slowly added dropwise atroom temperature to 4-(trifluoromethyl) benzyl bromide (1.63g, 6.82mmol) and the reaction was carried out for 10 minutes.After the reaction was finished, it was concentrated under reduced pressure and extracted three times into a saturatedsolution of NaHCO3 is dissolved in ethyl acetate. The ethyl acetate layer was separated and dried with anhydrous Na2SO4,then purified by column chromatography (Ethyl acetate: Hexane = 1: 5) to give the compound 1d to give. Yield 16.7%

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4854 - 4857
[2]Patent: KR101651208,2016,B1 .Location in patent: Paragraph 0139-0141

55
[ 82380-18-5 ]
[ 402-49-3 ]
2-fluoro-4-[(4-trifluoromethylphenylmethoxy)]benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; at 100℃; for 1.5h;Sealed tube; Inert atmosphere;	[00191]To a stirred solution of <strong>[82380-18-5]2-fluoro-4-hydroxybenzonitrile</strong> (200 mg, 1.46 mmol) and 1-(bromomethyl)-4-(trifluoromethyl)benzene (349 mg, 1.46 mmol) in anhydrous acetonitrile (3.8ml) at room temperature in a sealable pressure tube under nitrogen was added Cs2CO3 (523 mg,1.6 mmol). The tube was then sealed and the mixture heated to 100 oC for 1.5 hr.[00192]The reaction was cooled to rt and diluted with DCM (10 ml) and washed with water(3x 5 ml). The organic layer was dried over MgSO4, filtered and evaporated to dryness to give369mg of the title compound TH NIvIR (500 M}Iz, DMSO-d6) 7.91-7.85 (m, 1H), 7.80 (d, J8.1 Hz, 2H), 7.69 (d, J = 8.0 Hz, 211), 7.30 (dd, J = 11.8, 2.4 Hz, lH), 7.08 (dd, J = 8.8, 2.4 Hz,1 H), 5.36 (s, 2H).

Reference： [1]Patent: WO2017/45751,2017,A1 .Location in patent: Paragraph 00191; 00192

56
[ 402-49-3 ]
[ 196603-96-0 ]
4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(4-trifluoromethylbenzyloxy)quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate; In N,N-dimethyl-formamide; for 4h;Reflux;	Example 4 Synthesis of 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(4-trifluoromethyl-benzyloxy)quinazoline (Compound 5) <strong>[196603-96-0]4-(4-bromo-2-fluoroanilino)-6-methoxy-7-hydroxyquinazoline</strong> (500mg, 1.37mmol), 1-(trifluoromethyl)-4-bromomethylbenzene (393mg, 1.64mmol) and potassium carbonate (568mg, 4.11mmol) were dispersed in N,N-dimethylformamide (DMF, 15mL). The resulting mixture was heated to reflux for 4 hours to conduct the reaction. The reaction mixture was cooled to room temperature and poured into water (80mL). The resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain a crude product (800mg). The crude product was purified by a preparative thin-layer chromatography (methylene chloride:methanol=10:1) to produce a white solid (287mg, yield: 40%). 1H-NMR(400 MHz, DMSO-d6) delta: 9.57(s, 1H), 8.36(s, 1H), 7.85-7.80(m, 3H), 7.74-7.72(m, 2H), 7.66(dd, 1H, J = 10.0, 2.0 Hz), 7.53-7.45(m, 2H), 7.30(s, 1H), 5.43(s, 2H), 3.97(s, 3H). MS 522, 524(M+1).

Reference： [1]Patent: EP3181554,2017,A1 .Location in patent: Paragraph 0110-0113

57
[ 32996-16-0 ]
[ 402-49-3 ]
C₁₉H₁₆F₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		As shown in Figure 1A, (i) NaH (60% dispersion in mineral oil, 11.0 mmol) was added in portionsat 0 C to a stirred solution of m<strong>[32996-16-0]ethyl 1H-indole-5-carboxylate</strong> 1 (1.89 g, 10.0 mmol) in dry DMF (10 mL).After stirring for 30 min at 0 C, 1-(bromomethyl)-4-(trifluoromethyl) benzene 2 (2.88 g, 12.0 mmol)was added and the mixture was then stirred at room temperature for 24 h. Then, the reaction mixturewas cooled to ambient temperature, poured into H2O (100 mL), and extracted with EtOAc (100 mL).The organic phase was dried over anhydrous Na2SO4. After evaporation of the solvents underreduced pressure, the crude product was purified on a silica gel column using EtOAc/petroleumether (1:9) to obtain the pure 3 (2.94 g, 80%) as a white solid. 1H NMR (400 MHz, CDCl3)delta 8.29(d, J = 1.6 Hz, 1H), 7.76-7.65 (m, 4H), 7.55 (d, J = 8.7 Hz, 1H), 7.36 (d, J = 7.9 Hz, 2H), 6.74-6.66 (m, 1H),5.60 (s, 2H), 3.83 (s, 3H); (ii) A suspension of 3 (1.67 g, 5.0 mmol) and 5 M NaOH solution (5 mL) inTHF (20 mL) was stirred at 50 C until consumption of the starting material. It was allowed to reachroom temperature, 2 M HCl was added, diluted with EtOAc (50 mL) and washed brine. The combinedorganic phase was dried (Na2SO4). After evaporation of the solvents under reduced pressure, the crudeproduct was purified on Flash chromatography to afford the product 4 (1.41 g, 88%) as a white solid.1H NMR (400 MHz, CDCl3) delta 12.47 (s, 1H), 8.26 (s, 1H), 7.76-7.66 (m, 3H), 7.65 (d, J = 3.2 Hz, 1H),7.51 (d, J = 8.6 Hz, 1H), 7.36 (d, J = 8.1 Hz, 2H), 6.68 (d, J = 3.1 Hz, 1H), 5.60 (s, 2H), 1.39 (s, 2H);(iii) To a solution of 4 (1.60 g, 5.0 mmol) in dry DMF (20 mL) were added 2.0 equiv. of DMAP (1.22 g,10 mmol) and 2.0 equiv. of BOP (4.42 g, 10 mmol) at 0 C in an ice bath. After stirring for 0.5 h, 1.2 equiv.of pyridin-4-ylmethanamine 5 (0.65 g, 6.0 mmol) were added, and the reaction was allowed to stiruntil all starting material had disappeared. Then, the mixture was poured into a 10% aqueous solutionof HCl. The aqueous phase was extracted with EtOAc (2 times), and the combined organic layers weredried (anhydrous Na2SO4) and concentrated in vacuo. Flash chromatography (Silica gel, hexane/ethylacetate = 2/1) yielded the desired product VSP-17 (1.64 g, 80%) as a colorless solid. 1H NMR (400 MHz,CDCl3)delta 8.59-8.51 (m, 2H), 7.83-7.77 (m, 2H), 7.65 (d, J = 8.1 Hz, 2H), 7.58-7.52 (m, 2H), 7.25-7.22(m, 2H), 7.04-6.96 (m, 2H), 6.63 (t, J = 6.0 Hz, 1H), 5.17 (s, 2H), 4.64 (d, J = 6.0 Hz, 2H). HRMS (ESI) m/zcalcd. for [M + H]+: 410.1480, found: 410.1478 [M + H]+.

Reference： [1]Molecules,2018,vol. 23

58
[ 64318-28-1 ]
[ 402-49-3 ]
2-(4-((4-(trifluoromethyl)benzyl)oxy)phenyl)ethan-1-aminium chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 232 - 244

59
[ 402-49-3 ]
[ 520-33-2 ]
(S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[4-(trifluoromethyl)benzyl]oxy}chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Alkaline conditions;	General procedure: K2CO3 (172.76 mg, 1.25 mmol) and the appropriate substitutedbromine (4-10 mmol) were added, under stirring, to a solution of <strong>[520-33-2]hesperetin</strong>(604 mg, 2 mmol) in anhydrous DMF (15 mL). Another 1 mmolof K2CO3 was intermittently added to the solution to keep the pH as aweak alkaline. The mixture was reacted at room temperature for 4-6 hunder atmospheric conditions. The progress of the reaction was monitoredby TLC. The reaction mixture poured into ice cold water thenacidified by dilute hydrochloric acid and extracted with ethyl acetate,then washed three times with saturated aqueous NaCl solution. After drying with anhydrous sodium sulfate, the solution was filtered throughabsorbent cotton. The precipitate obtained by removing the solventunder reduced pressure was purified by column chromatography (SiO2)using trichloromethane/petroleum ether (1:1-5) as eluent. The purifiedprecipitate was recrystallized from dichloromethane/petroleum ether.

Reference： [1]International Immunopharmacology,2018,vol. 61,p. 82 - 91

60
[ 617-05-0 ]
[ 402-49-3 ]
ethyl 3-methoxy-4-((4-(trifluoromethyl)benzyl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, potassium carbonate (1.86 g, 13.46 mmol), <strong>[617-05-0]ethyl 4-hydroxy-3-methoxybenzoate</strong> (1.2 g, 6.12 mmol) and CH3CN (26 mL) were added. The mixture was stirred for 30 minutes before 1- (bromomethyl)-3-(trifluoromethyl)benzene (1.59 g, 6.65 mmol) was added. The mixture was then stirred at reflux temperature for overnight hours. The reaction mixture was rotary evaporated. Water (100 mL) was then added to the residue and the aqueous was then extracted with EtOAc (50 mL x 3). The combined organic layers were evaporated and then dried in vacuo yielding 2.08 g (96 %) of ethyl 3-methoxy-4-((3-(trifluoromethyl)benzyl)oxy)benzoate as beige solid. (0311) lH NMR (400 MHz, Chloroform-d) delta 7.80 - 7.39 (m, 6H), 6.83 (d, J= 8.4 Hz, 1H), 5.24 (0312) (s, 2H), 4.33 (q, J = 7.1 Hz, 2H), 3.93 (s, 3H), 1.36 (t, J = 7.1 Hz, 3H).

Reference： [1]Patent: WO2018/144900,2018,A1 .Location in patent: Page/Page column 50

61
[ 14140-15-9 ]
[ 402-49-3 ]
1-(2-bromoethyl)-4-[4-(trifluoromethyl)benzyloxy]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate; In acetone; at 20℃; for 24h;	General procedure: The commercially available 4-hydroxyphenethyl bromide(4.9 mmol) was dissolved in 20 mL of acetone; K2CO3 (10 mmol) andthe appropriate benzyl bromide (9.9 mmol) were added, and the reactionmixture was stirred at room temperature for 24 h. After this timethe solvent was removed in vacuum, water was added, and the resultingsuspension was extracted with EtOAc (3×50 mL). The combined organiclayers were washed with water, dried on anhydrous sodium sulfate,and evaporated to obtain a residue that was recrystallized by theopportune solvent. By use of this procedure, the subsequent compoundswere obtained.

Reference： [1]Bioorganic Chemistry,2018,vol. 81,p. 334 - 339

62
[ 93247-78-0 ]
[ 402-49-3 ]
1-(4-(trifluoromethyl)benzyl)-1H-indazole-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/195123,2018,A1

63
[ 93247-78-0 ]
[ 402-49-3 ]
C₁₇H₁₃F₃N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With caesium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	A suspension of methyl 1H-indazole-7-carboxylate (1 eq.) and cesium carbonate (3 eq.) in DMF (0.74 M) was cooled to 0°C and 1-(bromomethyl)-4-(trifluoromethyl)benzene (1.2 eq., 0.89M in DMF) was added dropwise. The reaction mixture was allowed to warm slowly to rt over 16 h and then quenched with ice-water and extracted with TBME. The combined organic extracts were washed further with water and brine, dried over MgSO4, and filtered. Concentration of the filtrate in vacuo furnished the crude reaction product as a golden yellow oil, which was purified with column chromatography (Si02, 9:1 (v/v) Hex:EtOAc to EtOAc) to afford the product as a colorless oil (76percent yield).

Reference： [1]Patent: WO2018/195123,2018,A1 .Location in patent: Paragraph 00242

64
[ 3304-70-9 ]
[ 402-49-3 ]
dimethyl 1-(4-(trifluromethyl)benzyl)-1H-imidazole-4,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 30 - 120℃;	Free <strong>[3304-70-9]dimethyl 1H-imidazole-4,5-dicarboxylate</strong> (7 g, 38 mmol, 1 eq), 4-(trifluromethyl)benzyl bromide (1 to 5 eq) and potassium carbonate (0.2 to 5 eq) were dissolved in about 60 ml of DMF, and then the mixture was stirred at 30 to 120 C. for 3 to 24 hours. TLC (PE:EA=1:2) showed that the <strong>[3304-70-9]dimethyl 1H-imidazole-4,5-dicarboxylate</strong> was reacted almost completely, and a new spot appeared. The mixture was added with 150 ml of water and further added with 200 ml of ethyl acetate, and thereby the layers were separated. The organic layer was washed with 200 ml of water and dried by a rotary evaporator to obtain a transparent liquid which was used in the next step.

Reference： [1]Patent: US2018/370921,2018,A1 .Location in patent: Paragraph 0101-0103

65
[ 71759-89-2 ]
[ 402-49-3 ]
4-iodo-1-(4-(trifluoromethyl)benzyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	4-Iodo-1H-imidazole (1 g, 5.2 mmol) and N,N-diisopropylethylamine (1.34 g, 10.4 mmol) wereadded to dry dimethylformamide (20 mL), and 1-(bromomethyl)-4-(trifluoromethyl)benzene (1.48 g,6.2 mmol) was added to reaction mixture at 20 C. After the reaction mixture was stirred at 20 Cuntil the starting material disappeared in thin layer chromatography (TLC), the reaction mixture was distilled in vacuo, dichloromethane (50 mL) was added to the mixture. The organic extract was washed twice with saturated aqueous NaHCO3 and NaCl (20 mL) respectively, and the organic extract was dried over Na2SO4. After solvent was removed under vacuum, the unpurified product was added to the next step directly.

Reference： [1]Molecules,2019,vol. 24

66
[ 22479-95-4 ]
[ 402-49-3 ]
C₁₈H₁₅F₃O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 141,p. 8171 - 8184

67
[ 67-20-9 ]
[ 402-49-3 ]
(E)-1-([(5′-nitrofuran-2′-yl)methylene]amino)-3-(p-(trifluoromethyl)benzyl) imidazolidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: <strong>[67-20-9]Nitrofurantoin</strong>, 1, (2.94mmol, 0.7g) was dissolved in 10mL of anhydrous dimethyl formamide (DMF), and trimethylamine (TEA, 4.41mmol, 1.5eq.) was added. The solution was stirred at room temperature for 15min. To resulting yellow solution, the appropriate n-alkyl or benzyl bromide (4.41mmol, 1.5eq) was added. The reaction was stirred at room temperature and monitored by TLC eluting with DCM:MeOH (19:1, v/v). Upon completion, the reaction was quenched with 20mL water and extracted with ethyl acetate (3X20mL). The organic layer was washed once with saturated NH4Cl and once with water. The solution was concentrated in vacuo. The resulting paste was purified by recrystallization in ethanol/water) to afford the desired analogue (Scheme 1 ).

Reference： [1]Bioorganic Chemistry,2020,vol. 96

68
[ 3272-08-0 ]
[ 402-49-3 ]
3-nitro-4-((4-(trifluoromethyl)benzyl)oxy)benzonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 1178 - 1198

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Ghs Precautionary Statements

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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P103	Read label before use
Prevention
Code	Phrase
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P222	Do not allow contact with air.
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P234	Keep only in original container.
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P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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Response
Code	Phrase
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P321
P322
P330	Rinse mouth.
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P378
P380	Evacuate area.
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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.
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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.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P401
P402	Store in a dry place.
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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
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H220	Extremely flammable gas
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H222	Extremely flammable aerosol
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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
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H242	Heating may cause a fire
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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