[ CAS No. 1097871-23-2 ]

Name: 1-Chloro-2,5-difluoro-4-iodobenzene
Brand: Ambeed
SKU: A102750
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Quality Control of [ 1097871-23-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1097871-23-2 ]

SDS

Product Details of [ 1097871-23-2 ]

CAS No. :	1097871-23-2	MDL No. :	MFCD18379746
Formula :	C₆H₂ClF₂I	Boiling Point :	218.6±35.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	274.43	Pubchem ID :	51000088
Synonyms :

Computed Properties of [ 1097871-23-2 ]

TPSA :Topological Polar Surface Area	0	H-Bond Acceptor Count :	2
XLogP3 :	3.4	H-Bond Donor Count :	0
SP3 :	0.00	Rotatable Bond Count :	0

Safety of [ 1097871-23-2 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305 P351 P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1097871-23-2 ]

Upstream synthesis route of [ 1097871-23-2 ]
Downstream synthetic route of [ 1097871-23-2 ]

[ 1097871-23-2 ] Synthesis Path-Upstream 1~1

1
[ 2367-91-1 ]
[ 1097871-23-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	at 0 - 20℃; for 2.17 h;	Trifluoromethanesulfonic acid (9.9 mL, 110 mmol) was added to 2-chloro-1,4-difluorobenzene (2.2 g, 15 mmol) at room temperature and then cooled to 0°C. N- Iodosuccinimide (3.16 g, 14.1 mmol) was then added in multiple portions. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was poured over ice-water and extracted with hexane. The organic layer was washed with saturated Na₂SO₄, dried and concentrated. The crude product was purified by silica gel chromatography (100percent hexanes) to give l-chloro-2,5-difluoro-4-iodobenzene (3.0 g, 74percent). ¹H NMR (400 MHz, CDCl₃) δ 7.52 (dd, J = 5.4, 7.8, IH), 7.17 - 7.08 (m, IH).

Reference： [1] Patent: WO2009/6567, 2009, A2. Location in patent: Page/Page column 97

[ 1097871-23-2 ] Synthesis Path-Downstream 1~5

1
[ 1097871-23-2 ]
C₂₇H₂₇BO₃ [ No CAS ]
C₂₇H₁₇ClF₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 12h;Inert atmosphere;	49-(4-methoxy)-10 borate 1 mmol,1-mmol-4-iododifluorobenzene 1 mmol, tetrakis(triphenylphosphine)palladium 0.1 mmol, toluene 40 mL,10 mL of ethanol and 340 mmol of K2CO (formed as a solution with 10 mL of distilled water) were added to the reaction flask, and then the system was evacuated and protected with nitrogen.The reaction was carried out at 100 C for 12 hours.After the end of the reaction, extraction, rotary distillation, column chromatography (eluent: n-hexane / dichloromethane = 1:1),Recrystallization gave the product A7.The yield was 69%.5A70.5mmol, boranoic acid pinacol ester 1.5mmol,Palladium acetate 0.05 mmol, 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl 0.1 mmol,1.5 mmol of potassium acetate and 25 mL of 1,4-dioxane were added to the reaction flask.The system is then evacuated, protected by nitrogen, and reacted at 90 C for 12 hours.After the reaction is over, extract, spin,Column chromatography (eluent: n-hexane / dichloromethane = 2:1),Recrystallization gave the product B7.The yield was 65%.6 The final product g is obtained by Suzuki coupling reaction:B70.25mmol, the product obtained in step 2, namely 9-bromo-10-(4-cyano)benzoquinone 0.21mmol,Catalyst tetrakis(triphenyl)phosphine palladium 0.03 mmol,Toluene 15mL, ethanol 5mL, K2CO38.4mmol (formed into solution with 5mL distilled water),It was added to the reaction flask and refluxed at 100 C for 12 h under the protection of nitrogen.After the reaction is completed, methanol is washed with hot water, suction filtered, and toluene is recrystallized.Sublimation gives the final product.The yield was 58%.The molecular formula is C48H29F2NO

Reference： [1]Patent: CN109678759,2019,A.Location in patent: Paragraph 0103; 0104; 0105

2
[ 1097871-23-2 ]
(S,E)-N-((3-fluorooxetan-3-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]
(S)-N-((S)-(4-chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.64 g		Synthesis of (S)-N-((S)-(4-Chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide To an oven dried, 100 mL, round bottom flask, under a nitrogen atmosphere, was added <strong>[1097871-23-2]1-chloro-2,5-difluoro-4-iodobenzene</strong> (2.41 g, 8.77 mmol) in anhydrous THF (35 mL). The resulting solution was cooled to -100 C. with an ether/liquid nitrogen bath, and then n-butyllithium (1.6M in hexanes, 5.48 mL, 8.77 mmol) was added dropwise, keeping the internal temperature between -90 and -100 C. The resulting yellow mixture was stirred between -90 and -100 C. for 30 minutes, and then (S,E)-N-((3-fluorooxetan-3-yl)methylene)-2-methylpropane-2-sulfinamide (2.0 g, 9.65 mmol) in THF (5 mL) was added dropwise via syringe, keeping the internal temperature between -90 and -100 C. The resulting mixture was stirred between -90 and -100 C. for 30 minutes and then quenched at the same temperature by dropwise addition of saturated ammonium chloride (25 mL). The mixture was diluted with water (50 mL) and ethyl acetate (50 mL). The layers were shaken and separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to a viscous nearly colorless oil which was purified with silica gel using a gradient to 50% ethyl acetate/hexanes providing (S)-N-((S)-(4-chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide (1.64 g, 4.6 mmol) the desired single diastereomer, as a white foam. 1H NMR (400 MHz, Methanol-d4) delta 7.58-7.37 (m, 2H), 5.28 (d, J=26.1 Hz, 1H), 4.99-4.89 (m, 1H), 4.85-4.76 (m, 1H), 4.69-4.50 (m, 2H), 1.21 (s, 9H). LCMS-ESI (POS.) m/z: 356.10 (M+H)+.

Reference： [1]Patent: US2019/77793,2019,A1.Location in patent: Paragraph 0509

3
[ 1097871-23-2 ]
(S,E)-2-methyl-N-(oxetan-3-ylmethylene)propane-2-sulfinamide [ No CAS ]
(S)-N-((R)-(4-chloro-2,5-difluorophenyl)(oxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.88 g		Step 2: Preparation of (S)-N-(-(4-chloro-2,5-difluorophenyl)(oxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide To an oven-dried 500 mL round bottom flask under a nitrogen atmosphere was added <strong>[1097871-23-2]1-chloro-2,5-difluoro-4-iodobenzene</strong> (9.93 g, 36.18 mmol) in 175 mL anhydrous THF. The resulting solution was cooled to -100 C. with a diethyl ether/liquid nitrogen bath, and then n-BuLi solution (1.6M in THF, 22.6 mL, 36.2 mmol) was added dropwise so that the internal temperature remained between -90 and -100 C. The resulting yellow colored mixture was stirred between -90 and -100 C for 30 min and then (S,E)-2-methyl-N-(oxetan-3-ylmethylene)propane-2-sulfinamide (7.53 g, 39.80 mmol) in 15 mL THF was added dropwise via syringe so that the internal temperature remained between -90 and -100 C. The resulting mixture was stirred between -90 and -100 C. for 30 min and then quenched at the same temperature by dropwise addition of saturated NH4Cl solution followed by warming to room temperature. The mixture was diluted with 150 mL water and 150 mL EtOAc. The layers were shaken and separated and the organic phase was washed with saturated NaCl solution, dried over Na2SO4, and concentrated to a viscous nearly colorless oil which was purified by MPLC using silica gel (0-100% ethyl acetate/hexanes) to provide the desired single diastereomer (6.88 g, 20.38 mmol) as a white foam. LCMS-APCI (POS.) m/z: 338.1 (M+H)+

Reference： [1]Patent: US2019/77793,2019,A1.Location in patent: Paragraph 0301

4
[ 2367-91-1 ]
[ 1097871-23-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-iodo-succinimide; trifluorormethanesulfonic acid; at 0 - 20℃; for 2.16667h;	Trifluoromethanesulfonic acid (9.9 mL, 110 mmol) was added to 2-chloro-1,4-difluorobenzene (2.2 g, 15 mmol) at room temperature and then cooled to 0C. N- Iodosuccinimide (3.16 g, 14.1 mmol) was then added in multiple portions. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was poured over ice-water and extracted with hexane. The organic layer was washed with saturated Na2SO4, dried and concentrated. The crude product was purified by silica gel chromatography (100% hexanes) to give l-chloro-2,5-difluoro-4-iodobenzene (3.0 g, 74%). 1H NMR (400 MHz, CDCl3) delta 7.52 (dd, J = 5.4, 7.8, IH), 7.17 - 7.08 (m, IH).

Reference： [1]Patent: WO2009/6567,2009,A2.Location in patent: Page/Page column 97

5
[ 1097871-23-2 ]
[ 105-53-3 ]
[ 1097871-27-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With copper(l) iodide; caesium carbonate; 2-Phenylphenol; In tetrahydrofuran; at 90℃; for 12h;	Copper(I) iodide (69.4 mg, 0.364 mmol), 2-phenylphenol (93.0 mg, 0.546 mmol) and cesium carbonate (1.78 g, 5.46 mmol) were added to a dry flask under nitrogen. Ethyl malonate (1.11 mL, 7.29 mmol) was added to the mixture, followed by l-chloro-2,5-difluoro-4- iodobenzene (1.00 g, 3.64 mmol) in tetrahydrofuran (3.64 mL, 44.9 mmol). The reaction mixture was sealed and heated to 90C. After 12 hours, the reaction mixture was allowed to cool to room temperature and then diluted with saturated NH4Cl and EtOAc. The organic layer was separated, dried and filtered through Celite. The brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane) to give diethyl 2-(4-chloro-2,5-difluorophenyl)malonate (0.65 g, 58%). 1H NMR (400 MHz, CDCl3) delta 7.37 (dd, J = 6.3, 9.3, IH), 7.17 (dd, J = 6.1, 8.9, IH), 4.91 (s, IH), 4.33 - 4.14 (m, 4H), 1.28 (t, J = 7.2, 6H).

Reference： [1]Patent: WO2009/6567,2009,A2.Location in patent: Page/Page column 98

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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H315	Causes skin irritation
H316	Causes mild skin irritation
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H319	Causes serious eye irritation
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Code	Phrase
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H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1097871-23-2 ]

Quality Control of [ 1097871-23-2 ]

Related Doc. of [ 1097871-23-2 ]

Product Details of [ 1097871-23-2 ]

Computed Properties of [ 1097871-23-2 ]

Safety of [ 1097871-23-2 ]

Application In Synthesis of [ 1097871-23-2 ]

[ 1097871-23-2 ] Synthesis Path-Upstream 1~1

[ 1097871-23-2 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 1097871-23-2 ]

Aryls

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Chlorides

Precautionary Statements-General

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Physical hazards

Health hazards

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