[ CAS No. 349-75-7 ] {[proInfo.proName]}

Name: 349-75-7|(3-(Trifluoromethyl)phenyl)methanol|98%
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SKU: A224961
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Quality Control of [ 349-75-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 349-75-7 ]

Product Details of [ 349-75-7 ]

CAS No. :	349-75-7	MDL No. :	MFCD00004645
Formula :	C₈H₇F₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BXEHKCUWIODEDE-UHFFFAOYSA-N
M.W :	176.14	Pubchem ID :	67681
Synonyms :

Calculated chemistry of [ 349-75-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.57
TPSA :	20.23 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 :	No
Log Kp (skin permeation) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	3.2
Log Po/w (MLOGP) :	2.61
Log Po/w (SILICOS-IT) :	2.68
Consensus Log Po/w :	2.53

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.58
Solubility :	0.462 mg/ml ; 0.00262 mol/l
Class :	Soluble
Log S (Ali) :	-2.3
Solubility :	0.882 mg/ml ; 0.00501 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.11
Solubility :	0.137 mg/ml ; 0.000776 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 349-75-7 ]

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 [ 349-75-7 ]

* 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 [ 349-75-7 ]
Downstream synthetic route of [ 349-75-7 ]

[ 349-75-7 ] Synthesis Path-Upstream 1~4

1
[ 349-75-7 ]
[ 2338-76-3 ]

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

2
[ 349-75-7 ]
[ 351-35-9 ]

Reference： [1] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253
[2] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897

3
[ 67-56-1 ]
[ 349-75-7 ]
[ 201230-82-2 ]
[ 616-38-6 ]
[ 62451-84-7 ]

Reference： [1] Green Chemistry, 2018, vol. 20, # 5, p. 969 - 972

4
[ 349-75-7 ]
[ 62451-84-7 ]

Reference： [1] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897

[ 349-75-7 ] Synthesis Path-Downstream 1~88

1
[ 349-75-7 ]
[ 401-79-6 ]
[ 454-89-7 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4079,4082

2
[ 454-92-2 ]
[ 349-75-7 ]

Yield	Reaction Conditions	Operation in experiment
97%		To lithium aluminum hydride (37.9 g, 1.2 mol, 1.2 equiv.) in THF (500 mL) at 0 C. was added 3-(trifluoromethyl)benzoic acid (200 g, 1.0 mol) in THF (1000 mL) dropwise at 0-10 C. The mixture was stirred overnight followed by dropwise addition of 10% sulfuric acid (500 ml) and water (1000 mL). The solution was filtrated and the filtrate was extracted with ethyl acetate (3×500 mL). The combined organic solution was washed with water (500 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as an orange oil (180 g, 97%).

Reference： [1]Organic Preparations and Procedures International,2002,vol. 34,p. 665 - 670
[2]Patent: US2005/234046,2005,A1 .Location in patent: Page/Page column 97
[3]Helvetica Chimica Acta,1971,vol. 54,p. 868 - 897

3
[ 349-75-7 ]
[ 2373-51-5 ]
[ 88023-85-2 ]

Reference： [1]Synthesis,1983,p. 762 - 763
[2]European Journal of Medicinal Chemistry,1993,vol. 28,p. 463 - 472

4
[ 349-75-7 ]
[ 454-89-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hypochlorite solution; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; isocyanuric acid; In ethyl acetate; at 0 - 10℃; for 5h;pH > 12;	General procedure: To a mixture of the alcohol (3.839 mmol), K2CO3 (2.0 equiv, 7.678 mmol) and cyanuric acid (0.1 equiv, 0.384 mmol) in 20 mL of ethyl acetate were added TEMPO or AZADO (3 mol%, 0.115 mmol) and 12% NaOCl (1.2 equiv, 4.607 mmol, Wako Pure Chemical Industries, Ltd.) at 0-10C. The mixture was then stirred to complete. The reaction mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford the corresponding product.
98%	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; isocyanuric acid; In water; ethyl acetate; at 0 - 10℃; for 5h;Inert atmosphere;	To a mixture of 16 (676 mg, 3.84 mmol), cyanuric acid (50 mg, 0.38mmol, 0.1 equiv), and K2CO3 (1.06 g, 7.68 mmol, 2.0 equiv) in EtOAc(10 mL) were added TEMPO (18 mg, 0.12 mmol, 0.03 equiv) and 12%(w/w) aq NaOCl (2.86 g, 4.61 mmol, 1.2 equiv) at 0-10 C, and themixture was stirred for 5 h at 0-10 C. The mixture was then extractedwith EtOAc (20 mL). The organic layer was washed with 10% aq.NaCl (10 mL) then concentrated under reduced pressure. The residuewas purified by column chromatography (silica gel, EtOAc-hexane) togive a colorless oil; yield: 398 mg (98%).1H NMR (600 MHz, CDCl3): delta = 7.70 (t, J = 7.7 Hz, 1 H), 7.90 (d, J = 7.9Hz, 1 H), 8.09 (d, J = 7.6 Hz, 1 H), 8.15 (s, 1 H), 10.09 (s, 1 H).13C NMR (151 MHz, CDCl3): delta = 123.6 (q, J = 272.5 Hz), 126.5 (q, J = 3.8Hz), 129.8, 130.8 (q, J = 3.3 Hz), 131.9 (q, J = 33.2 Hz), 132.7, 136.9,190.7.
85%	With tert.-butylhydroperoxide; 2,2?-((1E,1?E)-(1,2-phenylenebis(azanylylidene))bis(methanylylidene))diphenolcopper(II); sodium hydroxide; In water; acetonitrile; at 20℃;	General procedure: Alcohol (0.5 mmol), salophen copper (II) complex (2 mol%), NaOH (0.6 equiv), and 70% TBHP in water (1.1 equiv) were dissolved in acetonitrile (5 mL), and the homogeneous solution was stirred at room temperature in air overnight. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified over silica gel by column chromatography (10-25% EtOAc in hexane).

73%

With Nitrogen dioxide; In acetonitrile; at 140℃; under 760.051 Torr; for 5h;Sealed tube;

General procedure: To a dried 45 mL tube equipped with a magnetic stirring, 2 mL acetonitrile, 0.5 mmol substrate and 0.046 mmol NO2 were sequentially added (note: the air in the tube was not removed). Then the reaction tube was sealed and stirred magnetically at a constant-temperature to perform the reaction for 5 h. Once the reaction time was reached, GCanalysis of the mixture provided the GC yields of the products. Then the crude product from another parallel experiment was purified by silicagel chromatography to give the desired product.

Reference： [1]Chemical Communications,1999,p. 1907 - 1908
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 448 - 452
[3]Tetrahedron Letters,2015,vol. 56,p. 3905 - 3908
[4]Synthesis,2015,vol. 47,p. 3467 - 3472
[5]Synlett,1999,p. 1489 - 1490
[6]Chemistry - A European Journal,2016,vol. 22,p. 4008 - 4014
[7]Synthetic Communications,2015,vol. 45,p. 1334 - 1341
[8]Chemistry - A European Journal,2016,vol. 22,p. 8814 - 8822
[9]Catalysis Communications,2017,vol. 101,p. 98 - 101
[10]Journal of Organic Chemistry,1988,vol. 53,p. 2154 - 2159
[11]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 968 - 974
[12]International Journal of Chemical Kinetics,1997,vol. 29,p. 9 - 16
[13]Tetrahedron,1993,vol. 49,p. 7267 - 7276
[14]Journal of Chemical Research, Miniprint,1998,p. 2251 - 2272
[15]Journal of Chemical Research - Part S,1998,p. 644 - 645
[16]Journal of Chemical Research, Miniprint,1999,p. 2118 - 2135
[17]Journal of Chemical Research, Miniprint,2001,p. 562 - 585
[18]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2000,vol. 39,p. 1258 - 1263
[19]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2002,vol. 41,p. 493 - 499
[20]Journal of Physical Organic Chemistry,2002,vol. 15,p. 721 - 727
[21]Journal of the Indian Chemical Society,2004,vol. 81,p. 467 - 473
[22]Journal of Chemical Research,2004,p. 581 - 584
[23]Advanced Synthesis and Catalysis,2003,vol. 345,p. 497 - 505
[24]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2008,vol. 47,p. 669 - 676
[25]Journal of the Indian Chemical Society,2008,vol. 85,p. 496 - 501
[26]European Journal of Organic Chemistry,2010,p. 3445 - 3448
[27]Journal of Catalysis,2010,vol. 274,p. 76 - 83
[28]Journal of Organic Chemistry,2017,vol. 82,p. 11440 - 11446
[29]ACS Catalysis,2018,vol. 8,p. 6939 - 6947
[30]ChemBioChem,2019,vol. 20,p. 276 - 281
[31]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267
[32]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194

5
[ 454-89-7 ]
[ 349-75-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With [Ir(2,2':6',2'?-terpyridine)(1,10-phenanthroline)Cl](PF6)2; sodium formate; In ethanol; water; at 100℃; for 0.5h;Microwave irradiation;	General procedure: An aldehyde (1 mmol),sodium formate (4.5 eq), and catalyst (0.2 mol%) were taken in70% ethanol in water (4 mL) in a microwave vial and vortexed togenerate a homogenous solution. The mixture was heated in MWat 100 C using 150W of irradiation. Reaction progress was monitored by TLC. If complete conversion took place, the reaction colorturns to emerald green (color disappears after sometime) from paleyellow, and byproduct Na2CO3 precipitates. The Na2CO3 solid wasremoved by decanting the supernatant. The solid was washed withethyl acetate (20 mL). The combined decanted solution waswashed with water (5.0 mL), followed by brine solution (5.0 mL),dried over Na2SO4, filtered, and evaporated to dryness to affordthe desired alcohol as a pale-yellow liquid or off-white solid.

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9080 - 9083
Angew. Chem.,2016,vol. 128,p. 9226 - 9229,4
[2]Journal of Catalysis,2019,vol. 378,p. 283 - 288
[3]Tetrahedron Letters,1988,vol. 29,p. 4057 - 4060
[4]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 311 - 314
[5]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017
[6]Journal of the American Chemical Society,2007,vol. 129,p. 2772 - 2773
[7]Tetrahedron Letters,2009,vol. 50,p. 4624 - 4628
[8]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1768 - 1777
[9]Inorganic Chemistry,2017,vol. 56,p. 11282 - 11298

6
[ 51445-96-6 ]
[ 349-75-7 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 2585 - 2592
[2]Canadian Journal of Chemistry,1980,vol. 58,p. 2142 - 2145

7
[ 349-75-7 ]
[ 814-49-3 ]
[ 128732-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 16h;	General procedure: To a flask charged with the requisite benzyl alcohol (20.0mmol), Et3N (4.2 mL, 30.0 mmol, 150 mol%), DMAP (244mg, 2.0 mmol, 10 mol%), and THF (5 mL), was added neat diethyl chlorophosphate (2.9 mL, 20.0 mmol, 100 mol%) over a 30 min period at r.t. The resultant white, heterogeneous mixture was stirred for 16 h then poured into a solution of 1 M KHSO4 (50 mL). The separated organicphase was then washed with sat. aq NaHCO3 (30 mL) and brine (30 mL), before it was dried over MgSO4, filtered, and concentrated to give a crude oil. The crude oil was purified by flash chromatography (petroleum ether-EtOAc, 5:1, v/v) to give the product 1a.

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6016 - 6021
[2]Synlett,2014,vol. 25,p. 2928 - 2932

8
[ 349-75-7 ]
[ 124-63-0 ]
[ 96258-55-8 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 2165 - 2170

9
[ 349-75-7 ]
[ 814-68-6 ]
[ 144261-45-0 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 6371 - 6384

10
[ 349-75-7 ]
[ 881-10-7 ]
[ 119584-56-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1183 - 1190

11
[ 705-29-3 ]
[ 75-65-0 ]
[ 349-75-7 ]
[ 72390-17-1 ]
[ 72390-22-8 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 951 - 957

12
[ 705-29-3 ]
[ 75-65-0 ]
[ 349-75-7 ]
[ 72390-17-1 ]
[ 72390-22-8 ]
[ 72390-24-0 ]
[ 67646-72-4 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 951 - 957

13
[ 349-75-7 ]
[ 75-65-0 ]
[ 72390-17-1 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 951 - 957

14
[ 88023-79-4 ]
[ 349-75-7 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 9832 - 9839

15
[ 349-75-7 ]
[ 1005750-98-0 ]
[ 1005751-66-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 2h;	Preparation 22-1); 2-[3-Oxo-2-(3-trifluoromethyl-benzyl)-2,3-dihydro-pyridazin-4-yl]-butyricacid ethyl esterThe compound of Preparation 6-6) (100 mg, 0.48 mmol), DIAD(diisopropyl azodicarboxylate, 192 mg, 2.0 eq), (3-trifluoromethyl-phenyl)-methanol (168 mg, 2.0 eq) and triphenylphosphine (312 mg, 2.5 eq) were dissolved in THF (6 mL), and stirred for 2 h at room temperature. The mixture was concentrated under reduced pressure and separated by column chromatography (30% EA/Hexane) to give the title compound (158 mg, 90%).1H-NMR (500MHz, CDCl3) delta 7.76(d, IH), 7.65(s, IH), 7.60(d, IH), 7.53(d, IH), 7.43(t, IH), 7.20(d, IH), 5.40-5.30(ABq, 2H), 4.20-4.08(m, 2H), 3.85(t, IH), 2.01-1.76(two m, 2H), 1.19(t, 3H), 0.94(t, 3H)

Reference： [1]Patent: WO2008/16239,2008,A1 .Location in patent: Page/Page column 65

16
[ 402-24-4 ]
[ 349-75-7 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 2772 - 2773

17
[ 1428-54-2 ]
[ 349-75-7 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 2772 - 2773

18
[ 349-75-7 ]
(1R,2R,3R,5R,6R)-2-Amino-6-fluoro-3-(3-trifluoromethyl-benzyloxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

19
[ 349-75-7 ]
(1R,2R,3R,5R,6R)-2-Amino-6-fluoro-3-(3-trifluoromethyl-benzyloxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

20
[ 349-75-7 ]
(1R,2R,3R,5R,6R)-2-Azido-6-fluoro-3-(3-trifluoromethyl-benzyloxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

21
[ 349-75-7 ]
5-(3-trifluoromethyl-benzyloxy)-naphthalen-2-ylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1893 - 1899

22
[ 349-75-7 ]
N-[5-(3-trifluoromethyl-benzyloxy)-naphthalen-2-yl]-terephthalamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1893 - 1899

23
[ 349-75-7 ]
(Z)-2-Cyano-3,4-diphenyl-but-2-enoic acid 3-trifluoromethyl-benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1870 - 1877

24
[ 349-75-7 ]
2-cyano-4-phenyl-3-p-tolyl-but-2-enoic acid 3-trifluoromethyl-benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1870 - 1877

25
[ 349-75-7 ]
2-amino-4,5-diphenyl-thiophene-3-carboxylic acid 3-trifluoromethyl-benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1870 - 1877

26
[ 349-75-7 ]
2-amino-5-phenyl-4-p-tolyl-thiophene-3-carboxylic acid 3-trifluoromethyl-benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1870 - 1877

27
[ 349-75-7 ]
[ 35675-77-5 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

28
[ 349-75-7 ]
[ 221533-83-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

29
[ 349-75-7 ]
[ 1026739-32-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

30
[ 349-75-7 ]
[ 221533-17-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

31
[ 349-75-7 ]
6-(3-trifluoromethyl-benzyl)-5,6,7,8-tetrahydro-quinazoline-2,4-diamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

32
[ 349-75-7 ]
3-Trifluoromethylbenzylphosphonic acid [ No CAS ]