1206980-39-3|2-Chloro-3-(trifluoromethoxy)pyridine| Ambeed

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Quality Control of [ 1206980-39-3 ] Purity: 95% SDS Specification

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Product Details of [ 1206980-39-3 ]

CAS No. :	1206980-39-3
Formula :	C₆H₃ClF₃NO
M.W :	197.54
SMILES Code :	FC(F)(F)OC1=CC=CN=C1Cl
MDL No. :	MFCD17168453
InChI Key :	VJUMNUANNCTDHC-UHFFFAOYSA-N
Pubchem ID :	49871751

Safety of [ 1206980-39-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 1206980-39-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	2
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	35.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.9
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.89
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.25
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.58
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.42

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.85
Solubility	0.277 mg/ml ; 0.0014 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.57
Solubility	0.534 mg/ml ; 0.0027 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.27
Solubility	0.106 mg/ml ; 0.000535 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.76 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.93

Application In Synthesis of [ 1206980-39-3 ]

* 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 [ 1206980-39-3 ]

[ 1206980-39-3 ] Synthesis Path-Upstream 1~4

1
[ 1221171-74-9 ]
[ 1206980-39-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 120 - 150℃;	2-Ch.oro-3-triflaoroniεthoxypyridi.iε (8); 2-Chloro-3-trichloromethoxypyridine (7, 32.9 g, 0.13 mol) is added dropwise to a molten mixture Of SbF₃ (46.5 g, 0.26 mol, 2.0 eq) and SbCl₅ (5.8 g, 2.5 mL, 19.5 mmol, 0.15 eq) at 120 ⁰C and stirred for 7 h at 150 ⁰C. GC monitoring indicates 100percent conversion and disappearance of byproduct OCF₂CI. The mixture is then cooled to 0 ⁰C and dissolved in dichloromethane (300 mL). The solution is quenched with a saturated aqueous solution of sodium hydrogencarbonate (300 mL) and potassium fluoride (20percent, 150 mL), the aqueous layer is extracted with dichloromethane (2 x 150 mL). The combined organic layers are dried over sodium sulfate and the solvent is distilled. The crude product is distilled under vacuum to afford pure 2-chloro-3-trifluoromethoxypyridine (8, 14.9 g, 75.6 mmol, 60percent) as a colorless oil; b.p. 57-59 °C / 19 mbar.¹H NMR (CDCl₃, 300 MHz): δ = 8.37 (dd, J = 4.7, 1.5 Hz, 1 H), 7.68 (dt, J = 8.1, 1.5 Hz, 1 H), 7.41 (dd, J = 8.1, 4.7 Hz, 1 H). - ¹³C NMR (CDCl₃, 75 MHz): δ = 147.4, 144.9, 142.2, 130.8, 123.2, 120.2 (q, J= 260 Hz). - MS(EI): m/z = 197 [M⁺], 162 [M⁺-Cl].

References: [1] Patent: WO2010/40461, 2010, A1, . Location in patent: Page/Page column 20-21.
[2] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066.

2
[ 1258190-92-9 ]
[ 1206980-39-3 ]

References: [1] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066.

3
[ 1258190-92-9 ]
[ 1206980-39-3 ]

References: [1] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066.

4
[ 1206980-39-3 ]
[ 1206978-11-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With trimethylsilyl bromide In propiononitrile for 24 h; Reflux	2-Bromo-3-trifluoromethoxypyridine (23); A solution of 2-chloro-3-trifluoromethoxypyridine (8, 4.0 g, 20.2 mmol) and bromotrimethylsilane (6.3 g, 5.4 mL, 40.4 mmol, 2 eq) in propionitrile (20 mL) was heated under reflux for 24 h. GC monitoring indicated 100percent conversion. The mixture was distilled in vacuum to afford pure 2-bromo-3-trifluoromethoxypyridine (23, 3.9 g, 16.1 mmol, 80percent) as a colorless oil; b.p. 63-67 ⁰C / 13 mbar.¹H NMR (CDCl₃, 300 MHz): δ = 8.38 (dd, J = 4.7, 1.6 Hz, 1 H), 7.68 (d, J = 8.1, 1.6Hz, 1 H), 7.34 (dd, J = 8.1, 4.7 Hz, 1 H). - ¹⁹F NMR (CDCl₃, 282 MHz): δ = -58.0. - ¹³C NMR (CDCl₃, 75 MHz): δ = 147.8, 144.8, 142.2, 130.5, 123.7, 120.3 (q, J = 260 Hz). - C₆H₃ClF₃NO (241): calcd. (percent) C 29.78, H 1.25, N 5.79; found C 29.96, H 1.41, N 5.64.

References: [1] Patent: WO2010/40461, 2010, A1, . Location in patent: Page/Page column 34-35.
[2] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Amines • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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CAS No.: 1206980-39-3

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