[ CAS No. 1221171-95-4 ] {[proInfo.proName]}

Name: 1221171-95-4|6-Chloro-3-iodo-2-(trifluoromethoxy)pyridine|95%
Brand: Ambeed
SKU: A897612
Rating: 95 (22 reviews)

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3d Animation Molecule Structure of 1221171-95-4

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Quality Control of [ 1221171-95-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1221171-95-4 ]

SDS Specification

Alternatived Products of [ 1221171-95-4 ]

Product Details of [ 1221171-95-4 ]

CAS No. :	1221171-95-4	MDL No. :	MFCD22571777
Formula :	C₆H₂ClF₃INO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AFPPAOOKEWWCBK-UHFFFAOYSA-N
M.W :	323.44	Pubchem ID :	49871100
Synonyms :

Calculated chemistry of [ 1221171-95-4 ]

Physicochemical Properties

Num. heavy atoms :	13
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 :	48.65
TPSA :	22.12 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) :	-5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.3
Log Po/w (XLOGP3) :	3.98
Log Po/w (WLOGP) :	4.5
Log Po/w (MLOGP) :	2.53
Log Po/w (SILICOS-IT) :	3.59
Consensus Log Po/w :	3.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.56
Solubility :	0.00886 mg/ml ; 0.0000274 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.15
Solubility :	0.0231 mg/ml ; 0.0000715 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.2
Solubility :	0.0206 mg/ml ; 0.0000638 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Safety of [ 1221171-95-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1221171-95-4 ]

* 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 [ 1221171-95-4 ]
Downstream synthetic route of [ 1221171-95-4 ]

[ 1221171-95-4 ] Synthesis Path-Upstream 1~1

1
[ 1221171-95-4 ]
[ 1221171-96-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water	2-ChIoro-4-iodo-6-trifluoromethoxy pyridine (42); At 0 ⁰C, diisopropylamine (1.4 g, 1.9 mL, 13.6 mmol, 1.1 eq) was added dropwise to a solution of butyllithium (1.56 M in hexane, 9.0 mL, 13.6 mmol, 1.1 eq) in THF (20 mL). At -78 ⁰C, a solution of 2-chloro-5-iodo-6-trifluoromethoxypyridine (41, 4.0 g, 12.4 mmol, 1 eq) in THF (10 mL) was added dropwise and the reaction mixture was stirred for 1 h at this temperature. It was then neutralized with a solution of hydrochloric acid (2N, 10 mL), treated with a saturated aqueous solution sodium hydrogencarbonate (30 mL) and extracted with diethylether (3 x 20 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude dark oil was distilled under vacuum (b.p. 104-107 ⁰C / 16 mbar) to afford pure 2-chloro-4-iodo-6- trifluoromethoxypyridine (42, 3.2 g, 10.9 mmol, 80percent) as a colorless oil; ¹H NMR(CDCl₃, 300 MHz): δ = 7.66 (d, J= 1.0 Hz, 1 H), 7.34 (d, J= 1.0 Hz, 1 H). - ¹⁹F NMR (CDCl₃, 282 MHz): δ = -57.1 - ¹³C NMR (CDCl₃, 75 MHz): δ = 155.1, 149.4, 130.7, 120.3, 119.1 (q, J= 262 Hz), 108.3.

Reference： [1] Patent: WO2010/40461, 2010, A1, . Location in patent: Page/Page column 44
[2] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066

[ 1221171-95-4 ] Synthesis Path-Downstream 1~2

1
[ 1221171-70-5 ]
[ 1221171-95-4 ]

Yield	Reaction Conditions	Operation in experiment
78%		2-Chloro-5-iodo-6-trifluoromethoxy pyridine (41); At 0 0C, diisopropylamine (2.2 g, 3.1 mL, 22.2 mmol, 1.1 eq) was added dropwise to a solution of butyllithium (1.56 M in hexane, 14.2 mL, 22.2 mmol, 1.1 eq) in THF (35 mL). At -78 0C, a solution of <strong>[1221171-70-5]2-chloro-6-trifluoromethoxypyridine</strong> (2, 4.0 g, 20.2 mmol,1 eq) in THF (10 mL) was added dropwise followed after 2 h by a solution of iodide (5.7 g, 22.2 mmol, 1.1 eq) in THF (10 mL). The reaction mixture was allowed to reach 25 0C before being treated with a saturated aqueous solution of sodium sulfite (30 mL) and extracted with dichloromethane (3 x 20 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude dark oil was distilled under vacuum (b.p. 103-106 0C / 16 mbar) to afford pure 2-chloro-5-iodo-6- trifluoromethoxypyridine (41, 5.1 g, 15.7 mmol, 78%) as colorless needles; m.p. 33-350C.1H NMR (CDCl3, 300 MHz): delta = 8.11 (d, J = 8.1 Hz, 1 H), 7.03 (d, J= 8.1 Hz, I H). - 19F NMR (CDCl3, 282 MHz): delta = -57.1 - 13C NMR (CDCl3, 75 MHz): delta = 154.9, 151.7, 148.8, 142.0, 123.3, 120.4 (q, J = 264 Hz).
65.2%		To a solution of LDA (2 M, 2.5 mL) in THF ( 27.0 mL) was added dropwise a solution of <strong>[1221171-70-5]2-chloro-6-(trifluoromethoxy)pyridine</strong> (900 mg, 4.6 mmol) in THF (9.0 mL) at -78C under N2. The mixture was stirred at -78C for 2 h. A solution of I2 (1.3 g, 5.0 mmol, 1.0 mL) in THF (9.0 mL) was added at -78C. Then the mixture was slowly warmed to 25C and stirred for 12 h. The reaction was quenched with saturated H4C1 (15.0 mL) and extracted with ethyl acetate (15.0 mL chi 3). The combined organic phase was washed with brine (15 mL chi 3), dried over anhydrous Na2S04, filtered and concentrated to give a residue. The residue was purified by prep-TLC (Si02) to give 6-chloro-3-iodo-2-(trifluoromethoxy)pyridine (1.2 g, 3.0 mmol, 65.2% yield). 1H MR (400MHz, CHLOROFORM-i ) delta 8.10 (d, J= 8.1 Hz, 1H), 7.03 (d, J= 8.1 Hz, 1H).
61.07%		To a cooled solution of <strong>[1221171-70-5]2-chloro-6-(trifluoromethoxy)pyridine</strong> (0.3 g, 1.51 mmol) in anhydrous THF (2 ml.) was added LDA (2M in THF, 0.9 ml_, 1 .82 mmol) dropwise over 5 min and the resulting solution was stirred for 2 h at -78C. Iodine (0.5 g, 1 .97 mmol) in anhydrous TFIF (1 ml.) was then added dropwise over 5 min at -78C and stirred for an hour at same temperature. The reaction mixture was then quenched with saturated aq.NFUCI solution (5 ml_). Crude was extracted with EtOAc (10 mL X 2) and combined organic phases were washed with Na2S2C>3 (2M, 10 mL), dried over sodium sulphate, evaporated under reduced pressure to afford a title compound as colourless liquid (0.30g, 61 .07 %), Rf = 0.6 (05% EtOAc in n-Hexane); 1H NMR (300 MHz, Chloroform-d) d 8.09 (d, J = 8.0 Hz, 1 H), 7.02 (d, J = 8.2 Hz, 1 H).

Reference： [1]Patent: WO2010/40461,2010,A1 .Location in patent: Page/Page column 43-44
[2]European Journal of Organic Chemistry,2010,p. 6043 - 6066
[3]Patent: WO2018/222918,2018,A1 .Location in patent: Paragraph 00215
[4]Patent: WO2019/244049,2019,A1 .Location in patent: Paragraph 00246

2
[ 1221171-95-4 ]
[ 1221171-96-5 ]

Yield	Reaction Conditions	Operation in experiment
80%		2-ChIoro-4-iodo-6-trifluoromethoxy pyridine (42); At 0 0C, diisopropylamine (1.4 g, 1.9 mL, 13.6 mmol, 1.1 eq) was added dropwise to a solution of butyllithium (1.56 M in hexane, 9.0 mL, 13.6 mmol, 1.1 eq) in THF (20 mL). At -78 0C, a solution of 2-chloro-5-iodo-6-trifluoromethoxypyridine (41, 4.0 g, 12.4 mmol, 1 eq) in THF (10 mL) was added dropwise and the reaction mixture was stirred for 1 h at this temperature. It was then neutralized with a solution of hydrochloric acid (2N, 10 mL), treated with a saturated aqueous solution sodium hydrogencarbonate (30 mL) and extracted with diethylether (3 x 20 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude dark oil was distilled under vacuum (b.p. 104-107 0C / 16 mbar) to afford pure 2-chloro-4-iodo-6- trifluoromethoxypyridine (42, 3.2 g, 10.9 mmol, 80%) as a colorless oil; 1H NMR(CDCl3, 300 MHz): delta = 7.66 (d, J= 1.0 Hz, 1 H), 7.34 (d, J= 1.0 Hz, 1 H). - 19F NMR (CDCl3, 282 MHz): delta = -57.1 - 13C NMR (CDCl3, 75 MHz): delta = 155.1, 149.4, 130.7, 120.3, 119.1 (q, J= 262 Hz), 108.3.

Reference： [1]Patent: WO2010/40461,2010,A1 .Location in patent: Page/Page column 44
[2]European Journal of Organic Chemistry,2010,p. 6043 - 6066

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[ CAS No. 1221171-95-4 ] {[proInfo.proName]}

Quality Control of [ 1221171-95-4 ]

Related Doc. of [ 1221171-95-4 ]

Product Details of [ 1221171-95-4 ]

Calculated chemistry of [ 1221171-95-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1221171-95-4 ]

Application In Synthesis of [ 1221171-95-4 ]

[ 1221171-95-4 ] Synthesis Path-Upstream 1~1

[ 1221171-95-4 ] Synthesis Path-Downstream 1~2

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

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