[ CAS No. 590371-73-6 ] {[proInfo.proName]}

Name: 590371-73-6|4-Iodo-2-(trifluoromethyl)pyridine|97%
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3d Animation Molecule Structure of 590371-73-6

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Quality Control of [ 590371-73-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 590371-73-6 ]

SDS Specification

Alternatived Products of [ 590371-73-6 ]

Product Details of [ 590371-73-6 ]

CAS No. :	590371-73-6	MDL No. :	MFCD08234939
Formula :	C₆H₃F₃IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OYQSAEIWDLIZHC-UHFFFAOYSA-N
M.W :	272.99	Pubchem ID :	23436940
Synonyms :

Calculated chemistry of [ 590371-73-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.96
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	2.42
Log Po/w (WLOGP) :	3.86
Log Po/w (MLOGP) :	2.49
Log Po/w (SILICOS-IT) :	3.34
Consensus Log Po/w :	2.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.11 mg/ml ; 0.000403 mol/l
Class :	Soluble
Log S (Ali) :	-2.33
Solubility :	1.27 mg/ml ; 0.00464 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.86
Solubility :	0.0376 mg/ml ; 0.000138 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.61

Safety of [ 590371-73-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 590371-73-6 ]

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

Upstream synthesis route of [ 590371-73-6 ]
Downstream synthetic route of [ 590371-73-6 ]

[ 590371-73-6 ] Synthesis Path-Upstream 1~4

1
[ 201230-82-2 ]
[ 590371-73-6 ]
[ 131747-41-6 ]

Yield	Reaction Conditions	Operation in experiment
146 mg	Stage #1: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate In tetrahydrofuran at 120℃; for 20 h; Stage #2: With hydrogenchloride; water In water at 20℃; for 1 h;	Example 9 Preparation of 2-Trifluoromethyl-isonicotinic acid from 4-Chloro-2-trifluoromethyl pyridine A mixture of 182 mg (1.0 mmol) 4-Chloro-2-trifluoromethyl pyridine, 18.0 mg PdCl₂(dppp) and 210 mg sodium hydro gencarbonate in 1.5 ml THF and 1.5 ml water was stirred under 70 bar CO for 20 hour at 120°C, THF was removed under reduced pressure, 0.5 ml 2M NaOH was added and the suspension was filtered. The clear solution was treated with 0.52 ml hydrochloric acid 25 percent, stirred for lh at rt, filtered and the white crystals were dried at 40°C, to obtain 146 mg 2-trifluoromethyl-isonicotinic acid. GC-EI-MS: M 191⁺.

Reference： [1] Patent: WO2014/76127, 2014, A1, . Location in patent: Page/Page column 11-12

2
[ 124-38-9 ]
[ 590371-73-6 ]
[ 131747-41-6 ]

Reference： [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568

3
[ 590371-71-4 ]
[ 590371-73-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2 h; Cooling with acetone-dry ice	A 2.5M solution of BuLi in hexane (7.2 mL) was diluted in THF (30 mL) and cooled to -78⁰C (dry ice/acetone). To this solution were subsequently and dropwise added ¹Pr₂NH (2.5 mL) and the title compound from Step A above (4.9 g). The mixture was stirred at -78°C for 2 h, quenched at -78⁰C with MeOH (2 mL), concentrated and purified by EPO <DP n="159"/>chromatography (silica, cyclohexane/EtOAc) to afford the title compound as yellow needles (1.6 g, 32percent). ¹H-NMR (CDCl₃) D= 8.40 (d, 1 H), 8.06 (s, 1 H), 7.90 (d, 1 H).

Reference： [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[2] Patent: WO2006/128184, 2006, A2, . Location in patent: Page/Page column 157-158

4
[ 368-48-9 ]
[ 590371-73-6 ]

Reference： [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568

[ 590371-73-6 ] Synthesis Path-Downstream 1~6

1
[ 368-48-9 ]
[ 590371-73-6 ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 1559 - 1568

2
[ 5419-55-6 ]
[ 590371-73-6 ]
[ 1093407-58-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; for 3.5h; Inert atmosphere;	3 2-(Trifluoromethyl)pyridine-4-boronic acid To a solution of 4-iodo-2-(trifluoromethyl)pyridine [purchased from Matrix Scientific] (2.5 g, 9.16 mmol) and triisopropylborate (2.54 mL, 10.99 mmol) in anhydrous tetrahydrofuran (20 mL) at -78° C. under nitrogen was added dropwise a solution of n-butyl lithium in hexane (2.5 M, 4.03 mL, 10.07 mmol). The reaction was stirred at -78° C. for 2½ hours then allowed to warm slowly to -10° C. over 1 hour. The reaction mixture was then quenched by the addition of water (20 mL) and the tetrahydrofuran removed under reduced pressure. The resulting aqueous phase was diluted with water (40 mL) and washed with ether (240 mL). The aqueous phase was then acidified to pH 5 by the addition of acetic acid and the resulting oily suspension extracted with ether (100 mL). The organic phase was separated, washed with saturated brine (250 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give an off-white foam. Ether (12 mL) and hexanes (24 mL) were added and the resulting suspension stirred vigorously for 30 minutes then filtered to give 2-(trifluoromethyl)pyridine-4-boronic acid (1.163 g, 67% yield) as a cream solid. HPLC/MS Rt=1.54 min, m/z 192.1 (M+H+).

Reference： [1]Current Patent Assignee: MMV MEDICINES FOR MALARIA VENTURE PPP - US2014/135320, 2014, A1 Location in patent: Paragraph 0227; 0228

3
[ 552846-17-0 ]
[ 590371-73-6 ]
4-(1H-pyrazol-4-yl)-2-(trifluoromethyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.35%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 110℃; for 1h;Inert atmosphere; Microwave irradiation;	A microwave vial was charged with 1 ,4-Dioxane (1 OmL) and Water (3ml_) which was degassed with nitrogen for ~10 mins. To this was added 4-lodo-2-(trifluoromethyl)pyridine (500mg, 1 .83mmol), tert- butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole-1 -carboxylate (808mg, 2.75mmol) and potassium carbonate (506mg, 3.66mmol) followed by [1 ,1 - bis(diphenylphosphino)ferrocene]Palladium(ll) chloride dichloromethane complex (149mg, 0.1800mmol) . The vessel was then sealed, flushed with nitrogen and irradiated for 1 hour at 1 10C. LC-MS after this time showed conversion to the deprotected product and no starting material remaining, so reaction was worked up. The reaction mixture was concentrated to dryness then taken up in MeOH. This was loaded on to a 5g SCX cartridge and washed through with ~10CV of MeOH. The product was then eluted with 1 M ammonia in MeOH (~5CV). The ammonia wash was then concentrated to dryness, but did not yield the desired product. The MeOH washes were then concentrated to dryness and the remaining residue was triturated with chloroform. The resulting suspension was sonicated and then filtered, wasing with a little chloroform, affording 4-(1 H-pyrazol-4-yl)-2-(trifluoromethyl)pyridine (384mg, 1 .80mmol, 98.35% yield) as a beige solid. MS Method 2: RT: 1 .30 min, ES+ m/z 214.0 [M+H]+ H NMR (400MHz, MeOD) delta/ppm: 8.66 (s, 1 H), 8.34-8.38 (m, 2H), 8.08 (s, 1 H), 7.89-7.92 (m, 1 H).

Reference： [1]Patent: WO2016/55786,2016,A1 .Location in patent: Paragraph 00251

4
[ 57090-88-7 ]
[ 590371-73-6 ]
C₁₀H₅F₃N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	A solution of <strong>[57090-88-7]4-cyano-1H-imidazole</strong> (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield). 1H-NMR(DMSO, 400 MHz)8.25 (d, 1H), 7.72 (d, 1H), 7.46 (s, 1H), 7.28 (s, 1H), 7.15 (s, 1H). MS m/z (M + H)+ C10H6F3N4: measured 239.1, calcd 239.0

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3808 - 3812

5
[ 3019-25-8 ]
[ 590371-73-6 ]
1-((1R,2S)-2-(2-(trifluoromethyl)pyridin-4-yl)cyclobutyl)ethan-1-one [ No CAS ]
1-(2-(2-(trifluoromethyl)pyridin-4-yl)cyclobutyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84 % ee	With silver orthophosphate; D-Val-OH; palladium diacetate; trifluoroacetic acid; 3-nitro-5-trifluoromethylpyridin-2-ol at 100℃; for 24h; Microwave irradiation; Sealed tube; Overall yield = 50 percent; Overall yield = 10.2 mg; enantioselective reaction;

Reference： [1]Ewing, William R.; Hong, Kai; Hu, Liang; Luo, Fan; Xiao, Li-Jun; Yeung, Kap-Sun; Yu, Jin-Quan [Angewandte Chemie - International Edition, 2020, vol. 59, # 24, p. 9594 - 9600][Angew. Chem., 2020, vol. 132, # 24, p. 9681 - 9687,7]

6
[ 5117-12-4 ]
[ 590371-73-6 ]
1-morpholino-2-(2-(trifluoromethyl)pyridin-4-yl)propan-1-one [ No CAS ]
C₁₃H₁₅F₃N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetramethylammonium formiate; P(p-C₆H₄F)3 In 1,4-dioxane; water at 80℃; for 4h; Sealed tube;

Reference： [1]Cherney, Emily C.; Engle, Keary M.; Gurak, John A.; Joe, Candice L.; Vasquez, Alena M. [Journal of the American Chemical Society, 2020, vol. 142, # 23, p. 10477 - 10484]

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[ CAS No. 590371-73-6 ] {[proInfo.proName]}

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Calculated chemistry of [ 590371-73-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 590371-73-6 ]

Application In Synthesis of [ 590371-73-6 ]

[ 590371-73-6 ] Synthesis Path-Upstream 1~4

[ 590371-73-6 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 590371-73-6 ]

Fluorinated Building Blocks

Trifluoromethyls

Related Parent Nucleus of [ 590371-73-6 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 590371-73-6 ]

Related Parent Nucleus of
[ 590371-73-6 ]