[ CAS No. 242475-26-9 ] {[proInfo.proName]}

Name: 242475-26-9|2-Amino-2-(3-(trifluoromethyl)phenyl)acetic acid|97%
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Quality Control of [ 242475-26-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 242475-26-9 ]

CAS No. :	242475-26-9	MDL No. :	MFCD02662404
Formula :	C₉H₈F₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SRHNOGZIXICHOU-UHFFFAOYSA-N
M.W :	219.16	Pubchem ID :	2777629
Synonyms :

Calculated chemistry of [ 242475-26-9 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.7
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-8.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	-0.82
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	-0.39
Log Po/w (SILICOS-IT) :	1.6
Consensus Log Po/w :	0.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.78
Solubility :	36.4 mg/ml ; 0.166 mol/l
Class :	Very soluble
Log S (Ali) :	-0.03
Solubility :	205.0 mg/ml ; 0.933 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.35
Solubility :	0.97 mg/ml ; 0.00443 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 242475-26-9 ]

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

Application In Synthesis of [ 242475-26-9 ]

* 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 [ 242475-26-9 ]
Downstream synthetic route of [ 242475-26-9 ]

[ 242475-26-9 ] Synthesis Path-Upstream 1~3

1
[ 82425-18-1 ]
[ 242475-26-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 314 - 319

2
[ 2338-76-3 ]
[ 242475-26-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 314 - 319

3
[ 24424-99-5 ]
[ 242475-26-9 ]
[ 146621-92-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 314 - 319

[ 242475-26-9 ] Synthesis Path-Downstream 1~62

1
[ 24424-99-5 ]
[ 242475-26-9 ]
[ 146621-92-3 ]

Yield	Reaction Conditions	Operation in experiment
200 g		To a suspension of 2-amino-2-(3-(trifluoromethyl) phenyl) acetic acid (commercially available) (200 g, 913 mmol) in t-BuOH (2500 mL) cooled to 0 C was added sodium hydroxide pellets (36 g, 892 mmol) solution with water (1000 mL), this solution was stirred for 10 min and Boc anhydride (289.6 g, 1339 mmol) was added portionwise. The mixture was then warmed to ambient temperature and stirred for 18 h. The reaction mixture was concentrated to remove t-Butanol and diluted with water and the pH was adjusted up to 5-6 with solid citric acid and extracted with ethyl acetate (3 x 1500 mL). The combined organic layer were dried over anhydrous sodium sulphate and evaporated to afford 2-[(tert-butoxy)carbonyl]amino}-2-[3- (trifluoromethyl)phenyl] acetic acid (200 g) as a colourless gum which was used in the next step without further purification. HNMR (400 MHz, DMSO-d6) delta 12.98 (bs, 1H), 7.81 (d, 1H, J = 9.20 Hz), 7.72 (dd, 2H, J = 17.2, 7.60 Hz), 7.59 (t, 1H, J = 8.00 Hz), 5.28 (d, 1H, J = 8.40 Hz), 1.39 (s, 9H);MS: m/z 318 (M-l).

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319
[2]Patent: WO2019/38315,2019,A1 .Location in patent: Page/Page column 27; 28

2
[ 82425-18-1 ]
[ 242475-26-9 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

3
[ 82911-69-1 ]
[ 242475-26-9 ]
[(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)]-(3-trifluoromethyl-phenyl)-acetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 6852 - 6853

4
[ 242475-26-9 ]
(R)-1-[2-tert-Butoxycarbonylamino-2-(3-trifluoromethyl-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

5
[ 242475-26-9 ]
C₂₁H₁₇Cl₃F₃NO₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

6
[ 242475-26-9 ]
[ 1053181-86-4 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

7
[ 242475-26-9 ]
[2-{(S)-2-[(S)-1-(Benzyloxycarbonylamino-imino-methyl)-2-oxo-piperidin-3-ylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

8
[ 242475-26-9 ]
Boc-DL-1-Phg(3-CF₃)-Pro-Arg-H*2HOAc [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

9
[ 2338-76-3 ]
[ 242475-26-9 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319

10
[ 242475-26-9 ]
[ 407-25-0 ]
C₁₁H₅F₆NO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 292 - 304

11
[ 67-56-1 ]
[ 242475-26-9 ]
[ 179811-81-5 ]

Yield	Reaction Conditions	Operation in experiment
94%		Scheme Q; Step 1; Thionyl chloride (1.5 mL) was added dropwise to MeOH (35 mL) at 0 C. After stirring at 0 C for 45 minutes, the phenyl glycine (3 g, 13.7 mmol) was added, and the resulting solution was heated at 45 C for 16 h. The solution was concentrated. The residue was triturated with Et.20. The solid was collected and dried which furnished 3.5 g (94 %) of the methyl ester HCI salt.
7 g	With thionyl chloride; for 16h;Reflux;	(0685) To a well stirred solution of commercially available 2-amino-2-(3-(trifluoromethyl)phenyl)ace- tic acid (7 g, 32 mmol) in methanol (70 mL) was added thionyl chloride (4.6 mL, 64 mmol) at 0 C and refluxed for 16 h. The reaction mixture was concentrated. The residue was washed with diethyl ether (3 x 100 mL) to afford the title compound as hydrochloride salt (7g). (0686) FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-de) delta 9.32 (s, 3H, exchangeable), 7.98 (s, 1H), 7.98-7.80 (m, 2H), 7.71 (t, 1H, J = 7.6 Hz), 5.48 (d, 1H, J = 4.40 Hz), 3.71 (s, 3H); (0687) MS: m z 234.0 (M+l).
7 g	With thionyl chloride; at 0℃; for 16h;Reflux;	To a well stirred solution of <strong>[242475-26-9]2-amino-2-(3-(trifluoromethyl)phenyl)acetic acid</strong> (7 g, 32 mmol) in methanol (70 mL) was added thionyl chloride (4.6 mL, 64 mmol) at 0 C and refluxed for 16 h. The reaction mixture was concentrated. The residue was washed with diethyl ether (3 x 100 mL) to afford methyl 2-amino-2-(3- (trifluoromethyl)phenyl)acetate hydrochloride as the hydrochloride salt (7 g). NMR (400 MHz, DMSO-de) delta 9.32 (s, 3H), 7.98 (s, 1H), 7.98-7.80 (m, 2H), 7.71 (t, 1H, J = 7.6 Hz), 5.48 (d, 1H, J = 4.40 Hz), 3.71 (s, 3H); MS: m/z 234.0 (M+l).

Reference： [1]Patent: WO2011/119559,2011,A1 .Location in patent: Page/Page column 114-115
[2]Patent: WO2017/144183,2017,A1 .Location in patent: Page/Page column 83; 84
[3]Patent: WO2019/34603,2019,A1 .Location in patent: Page/Page column 26

12
[ 242475-26-9 ]
[ 1220903-34-3 ]

Reference： [1]Patent: WO2011/119559,2011,A1

13
[ 242475-26-9 ]
[ 959139-86-7 ]

Reference： [1]Patent: WO2011/119559,2011,A1

14
[ 242475-26-9 ]
[ 1220903-30-9 ]

Reference： [1]Patent: WO2011/119559,2011,A1

15
[ 242475-26-9 ]
[ 1220918-12-6 ]

Reference： [1]Patent: WO2011/119559,2011,A1

16
[ 242475-26-9 ]
[ 1336889-10-1 ]

Reference： [1]Patent: WO2011/119559,2011,A1

17
[ 242475-26-9 ]
[ 1220903-31-0 ]

Reference： [1]Patent: WO2011/119559,2011,A1

18
[ 242475-26-9 ]
C₁₁H₁₀F₃NO₃ [ No CAS ]
[ 1228568-48-6 ]

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1338 - 1342,5

19
[ 108-24-7 ]
[ 242475-26-9 ]
[ 1404627-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In water; N,N-dimethyl-formamide; at 20℃;	General procedure: To a solution of amino acid (50 mmol) in a 50 mL solution (25 mL DMF and 25 mL H2O), 52 mmol of acetic anhydride and triethylamine (60 mmol, 6.06 g) were added. The solution was stirred at room temperature overnight. After reaction, the solution was evacuated at reduced pressure to remove DMF. The residue was added to 30 mL of H2O, stirred at rt for 40 min, after which the pH value of the solution was changed to 7.0 with a solution of sodium carbonate and extracted with 20 mL of ethyl acetate three times. The combined organic solution was washed with saturated brine and then dried over anhydrous magnesium sulfate. The organic solution was evacuated to remove the organic solvent, and the residue was chromatographed to afford pure amino acid amides.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1338 - 1342,5

20
[ 242475-26-9 ]
3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-4-methyl-5-(3-(trifluoromethyl)phenyl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

21
[ 242475-26-9 ]
[ 1279819-87-2 ]

Reference： [1]Patent: WO2016/201168,2016,A1

22
[ 242475-26-9 ]
2-(methylamino)-2-(3-(trifluoromethyl)phenyl)ethan-1-ol [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

23
[ 242475-26-9 ]
[ 1245623-25-9 ]

Reference： [1]Patent: WO2016/201168,2016,A1

24
[ 242475-26-9 ]
tert-butyl-(2-((1,3-dioxoisoindolin-2-yl)oxy)-1-(3-(trifluoromethyl)phenyl)ethyl)(methyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

25
[ 242475-26-9 ]
2-(2-(methyl-(2,2,2-trifluoroacetyl)-1-(4-azanyl))-2-(3-(trifluoromethyl)phenyl)ethoxy)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

26
[ 242475-26-9 ]
5-bromo-N-(2-((1,3-dioxoisoindolin-2-yl)oxy)-1-(3-(trifluoromethyl)phenyl)ethyl)-6-methoxy-N-methylpicolinamide [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

27
[ 242475-26-9 ]
N-(2-(aminooxy)-1-(3-(trifluoromethyl)phenyl)ethyl)-5-bromo-6-methoxy-N-methylpicolinamide [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

28
[ 242475-26-9 ]
3-(5-bromo-6-methoxypyridin-2-yl)-4-methyl-5-(3-(trifluoromethyl)phenyl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

29
[ 242475-26-9 ]
3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-4-methyl-5-(3-(trifluoromethyl)phenyl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]
3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-4-methyl-5-(3-(trifluoromethyl)phenyl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]

Reference： [1]Patent: WO2016/201168,2016,A1

30
[ 67-56-1 ]
[ 242475-26-9 ]
methyl-2-amino-2-(3-(trifluoromethyl)phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In methanol; at 0℃; for 16h;Reflux; Inert atmosphere;	To a stirred solution of 2- amino-2-(3-(trifluoromethyl) phenyl) acetic acid (10 g, 46 mmol) in MeOH (200 mL) at 0 C under an argon atmosphere was added thionyl chloride (10.4 mL, 137 mmol). The reaction mixture was stirred at reflux for 16 h. After consumption of starting material (monitored by TLC), the volatiles were evaporated in vacuo to afford methyl 2-amino-2-(3-(trifluoromethyl) phenyl) acetate (10.1 g, crude) as an off-white solid used in the next step without further purification. TLC: 50% EtOAc Hexane (R1 0.5).

Reference： [1]Patent: WO2016/201168,2016,A1 .Location in patent: Paragraph 0303

31
[ 242475-26-9 ]
2-[(1H-1,3-benzodiazol-2-yl)amino]-2-[3-(trifluoromethyl)phenyl]acetic acid [ No CAS ]

Reference： [1]Patent: WO2017/144183,2017,A1

32
[ 242475-26-9 ]
methyl 4-{2-[(1H-1,3-benzodiazol-2-yl)amino]-2-[3-(trifluoromethyl)phenyl]acetyl}piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/144183,2017,A1

33
[ 242475-26-9 ]
methyl 2-[(1H-1,3-benzodiazol-2-yl)amino]-2-[3-(trifluoromethyl)phenyl]acetate [ No CAS ]

Reference： [1]Patent: WO2017/144183,2017,A1
[2]Patent: WO2019/34603,2019,A1

34
[ 242475-26-9 ]
N-(2-aminoethyl)-2-[(1H-1,3-benzodiazol-2-yl)amino]-2-[3-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: WO2017/144183,2017,A1

35
[ 242475-26-9 ]
2-[(1H-1,3-benzodiazol-2-yl)amino]-1-[3-(dimethylamino)azetidin-1-yl]-2-[3-(trifluoromethyl)phenyl]ethan-1-one hydrochloric acid [ No CAS ]

Reference： [1]Patent: WO2017/144183,2017,A1

36
[ 242475-26-9 ]
ethyl 2'-(1-amino-2-ethoxy-2-oxoethyl)-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 9535 - 9541

37
[ 242475-26-9 ]
ethyl 2-amino-2-(3-(trifluoromethyl)phenyl)acetate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 9535 - 9541

38
[ 242475-26-9 ]
[ 54-12-6 ]
1-(3-(trifluoromethyl)phenyl)-9H-pyrido[3,4-b]indole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 12247 - 12254

39
[ 242475-26-9 ]
C₁₇H₉ClF₃NO₃ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7100 - 7103

40
[ 242475-26-9 ]
2-phthalimido-N-(pyridin-2-yl)-2-(3-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7100 - 7103

41
[ 242475-26-9 ]
2-phthalimido-2-fluoro-N-(pyridin-2-yl)-2-(3-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7100 - 7103

42
[ 85-44-9 ]
[ 242475-26-9 ]
C₁₇H₁₀F₃NO₄ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7100 - 7103

43
[ 242475-26-9 ]
2-[(1H-1,3-benzodiazol-2-yl)amino]-N,N-dimethyl-2-[3-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: WO2019/34603,2019,A1

44
[ 242475-26-9 ]
2-[(1H-1,3-benzodiazol-2-yl)amino]-N-(2-methylpropyl)-2-[3-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: WO2019/34603,2019,A1

45
[ 242475-26-9 ]
2-[(1H-1,3-benzodiazol-2-yl)amino]-N-cyclopropyl-2-[3-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: WO2019/34603,2019,A1

46
[ 242475-26-9 ]
(-)2-[(1H-1,3-benzodiazol-2-yl)amino]-N,N-dimethyl-2-[3-(trifluoromethyl)phenyl]acetamide [ No CAS ]
(+)2-[(1H-1,3-benzodiazol-2-yl)amino]-N,N-dimethyl-2-[3-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: WO2019/34603,2019,A1

47
[ 242475-26-9 ]
[ 1036474-23-3 ]