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Quality Control of [ 106854-74-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 106854-74-4 ]

CAS No. :	106854-74-4	MDL No. :	N/A
Formula :	C₉H₉F₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	206.16	Pubchem ID :	-
Synonyms :

Safety of [ 106854-74-4 ]

Signal Word:	Class:	N/A
Precautionary Statements:	UN#:	N/A
Hazard Statements:	Packing Group:	N/A

Application In Synthesis of [ 106854-74-4 ]

* 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 [ 106854-74-4 ]
Downstream synthetic route of [ 106854-74-4 ]

[ 106854-74-4 ] Synthesis Path-Upstream 1~2

1
[ 106854-74-4 ]
[ 160968-99-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron tribromide In dichloromethane for 2 h;	A 1 M solution of boron tribromide (30 mL, 0.03 mol) in CH2Cl2 was added to a solution ofintermediate 2 (4.3 g, 0.02 mol) in anhydrous CH2Cl2 (50 mL) at -20 °C. The reaction mixture waswarmed to room temperature and, after, quenched by addition of excess saturated aqueous sodiumbicarbonate solution (40 mL). The organic layer was dried over Na2SO4, filtered, and concentratedunder reduced pressure. The crude material was sufficiently pure to be used directly in the next step(yield 98percent). Yellow oil (3.8 g); UPLC/MS purity 99percent, tR = 5.37. C8H7F3O2, MW 192.14, MonoisotopicMass 192.04, [M + H]- 191.0. 1H-NMR (300 MHz, CDCl3) δ 4.36 (q, J = 8.4 Hz, 2H, O–CH2–CF3),6.81–7.11 (m, 4H, Ar–H), 9.72 (br.s., 1H, O–H). 13C-NMR (75 MHz, CDCl3) δ 56.2, 68.1, 119.2, 121.5,122.4, 123.7, 126.4, 127.3, 136.4

Reference： [1] Molecules, 2018, vol. 23, # 9,
[2] Patent: US5387603, 1995, A,
[3] Patent: WO2011/30356, 2011, A2, . Location in patent: Page/Page column 23
[4] Patent: WO2011/101864, 2011, A1, . Location in patent: Page/Page column 21-22
[5] Patent: US2012/165548, 2012, A1, . Location in patent: Page/Page column 11

2
[ 106854-74-4 ]
[ 160969-03-9 ]

Reference： [1] Patent: WO2011/101864, 2011, A1,

[ 106854-74-4 ] Synthesis Path-Downstream 1~6

1
[ 353-83-3 ]
[ 90-05-1 ]
[ 106854-74-4 ]
[ 160969-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; N,N-dimethyl-formamide	5 1-(2-Bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene Reference Example 5 1-(2-Bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene To dry N,N-dimethylformamide (10 ml) were added 2-methoxyphenol (150 mg), 2,2,2-trifluoroethyl iodide (584 mg) and potassium carbonate (400 mg), and the mixture was stirred vigorously at 130° C. for 6 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent to give 179 mg of 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene as an oil. NMR (CDCl3)

Reference： [1]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED - US5387603, 1995, A

2
[ 106854-74-4 ]
[ 160968-99-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron tribromide; In dichloromethane; for 2.0h;	A 1 M solution of boron tribromide (30 mL, 0.03 mol) in CH2Cl2 was added to a solution ofintermediate 2 (4.3 g, 0.02 mol) in anhydrous CH2Cl2 (50 mL) at -20 C. The reaction mixture waswarmed to room temperature and, after, quenched by addition of excess saturated aqueous sodiumbicarbonate solution (40 mL). The organic layer was dried over Na2SO4, filtered, and concentratedunder reduced pressure. The crude material was sufficiently pure to be used directly in the next step(yield 98%). Yellow oil (3.8 g); UPLC/MS purity 99%, tR = 5.37. C8H7F3O2, MW 192.14, MonoisotopicMass 192.04, [M + H]- 191.0. 1H-NMR (300 MHz, CDCl3) delta 4.36 (q, J = 8.4 Hz, 2H, O-CH2-CF3),6.81-7.11 (m, 4H, Ar-H), 9.72 (br.s., 1H, O-H). 13C-NMR (75 MHz, CDCl3) delta 56.2, 68.1, 119.2, 121.5,122.4, 123.7, 126.4, 127.3, 136.4
	With boron tribromide; In dichloromethane;	To a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (3.83 g) in dry methylene chloride (50 ml) was added boron tribromide (3.1 ml) with stirring under ice cooling, and the mixture was reacted for 30 minutes. The reaction mixture was poured into an aqueous sodium bicarbonate solution (500 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent to give 2.37 g of 2-(2,2,2-trifluoroethoxy)phenol melting at 49-50 C. IR (KBr): upsilonOH 3310 cm-1
		Example-6 Preparation of 2-(2,2,2-trifluoroethoxy) phenol (XI) Boron tribromide (2.8 ml, 0.03 mole) was added to a solution of 1-methoxy-2-(2,2,2- trifluoroethoxy)benzene (X) (6.0 g, 0.03 mole) in methylene chloride (90 ml) with stirring below -10C. Reaction was stirred at -10 to -20C for 30 minutes. The reaction mixture was quenched using aqueous sodium bicarbonate solution. Organic layer was separated, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC) = 95 %.

	With aluminum (III) chloride; ethanethiol; In dichloromethane; at 0 - 20℃; for 4.0h;	Example 2: Preparation of 2-(2,2,2-Trifluoroethoxy)phenol (VI):a) Route-1 : To a mixture of ethanethiol (2 ml) in methylene chloride (4 ml) was added aluminum chloride (6.77 g, 50.9 mmol) slowly at 0 C. The resulting solution was stirred for 10 min and 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene (IV) (3.5 g, 16.9 mmol) in methylene chloride (4 ml) was added at 0C. The mixture was warmed to room temperature and stirred for 4 h. The mixture was diluted with water (50 ml), extracted with methylene chloride (3 X 100 ml) and concentrated under reduced pressure. The product was purified by column chromatography to give 3 g of 2-(2,2,2-trifluoroethoxy) phenol (VI) as a thick gel.
		Boron tribromide (2.8 ml, 0.03 mole) was added to a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (X) (6.0 g, 0.03 mole) in methylene chloride (90 ml) with stirring below -10 C. Reaction was stirred at -10 to -20 C. for 30 minutes. The reaction mixture was quenched using aqueous sodium bicarbonate solution. Organic layer was separated, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC)=95%

Reference： [1]Molecules,2018,vol. 23
[2]Patent: US5387603,1995,A
[3]Patent: WO2011/30356,2011,A2 .Location in patent: Page/Page column 23
[4]Patent: WO2011/101864,2011,A1 .Location in patent: Page/Page column 21-22
[5]Patent: US2012/165548,2012,A1 .Location in patent: Page/Page column 11

3
[ 353-83-3 ]
[ 90-05-1 ]
[ 106854-74-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 24h;	7.1.2. Preparation of 1-Methoxy-2-(2,2,2-trifluoroethoxy)benzene (2) 2-Methoxy-phenol 1 (5.19 g, 0.04 mol) was dissolved in DMF (25 mL), after addition of K2CO3,(16.6 g, 0.12 mol) a mixture that was heated to 90 °C. Then 2-iodo-1,1,1-trifluoroethane (4.2 mL,0.05 mol) was added dropwise in 30 min. The reaction mixture was then heated under reflux for 24 h.Inorganic residues were filtered off and organic mixture was concentrated under reduced pressure.The obtained crude product was purified using silica gel with AcOEt/Hexane (1/9, v/v) as an elutingsystem (isolated yield 65%). Yellow oil (5.6 g); UPLC/MS purity 99%, tR = 6.52. C9H9F3O2, MW206.16,Monoisotopic Mass 206.06, [M + H]+ 207.1. 1H-NMR (300 MHz, CDCl3) δ 3.91 (s, 3H, O-CH3), 4.36 (q,J = 8.4 Hz, 2H, O-CH2-CF3), 6.81-7.11 (m, 4H, Ar-H). 13C-NMR (75 MHz, CDCl3) δ 56.4, 68.3, 119.0,121.5, 122.3, 123.8, 126.1, 127.2, 138.9
	With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 10h;	5 Example-5 Preparation of 1-Methoxy-2-(2,2,2-trifluoroethoxy) benzene (X) To a solution of 2-Methoxy phenol (IX) (5 g, 0.04 moles) in N-methyl pyrrolidone (50 ml) were added, potassium carbonate (7.8 g, 0.06 mole) and 2, 2, 2-trifluoroethyl iodide (33.8 g, 0.16 mole) under stirring. The reaction mixture was stirred vigorously at 120°C for 10 hours. Water (150 ml) was added to the reaction mixture and the mixture was extracted in Toluene (250 ml).Organic layer was washed with 1N Sodium hydroxide solution (150 ml), followed by brine wash. The extract was dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 7.2 g of (X) as oil. Purity (by GC) = 94 %
	With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 10h;	5 To a solution of 2-Methoxy phenol (IX) (5 g, 0.04 moles) in N-methylpyrrolidone (50 ml) were added, potassium carbonate (7.8 g, 0.06 mole) and 2,2,2-trifluoroethyl iodide (33.8 g, 0.16 mole) under stirring. The reaction mixture was stirred vigorously at 120° C. for 10 hours. Water (150 ml) was added to the reaction mixture and the mixture was extracted in Toluene (250 ml). Organic layer was washed with 1 N Sodium hydroxide solution (150 ml), followed by brine wash. The extract was dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 7.2 g of (X) as oil. Purity (by GC)=94%

Reference： [1]Canale, Vittorio; Rak, Aleksandra; Kotanska, Magdalena; Knutelska, Joanna; Siwek, Agata; Bednarski, Marek; Nowinski, Leszek; Zygmunt, Małgorzata; Koczurkiewicz, Paulina; P ekala, Elzbieta; Sapa, Jacek; Zajdel, Paweł [Molecules, 2018, vol. 23, # 9]
[2]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - WO2011/30356, 2011, A2 Location in patent: Page/Page column 22; 23
[3]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - US2012/165548, 2012, A1 Location in patent: Page/Page column 11

4
[ 106854-74-4 ]
[ 160970-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 115 - 120 °C 2.2: 20 °C / pH 3 - 4 / Acidic conditions 3.1: sulfuric acid / 1,4-dioxane; water / 5 h / 95 - 100 °C 4.1: acetic acid / methanol / 1 h / 20 °C 4.2: 25 - 45 °C 5.1: sodium hydroxide; water / methanol / 6 h / 20 °C 6.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C
	Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 - 105 °C 3.1: sodium hydrogencarbonate; sodium hypochlorite; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0 - 5 °C 4.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 2 h 4.2: 1 h / 25 - 30 °C 4.3: 2 h / 40 - 45 °C
	Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 115 - 120 °C 2.2: 20 °C / pH 3 - 4 / Acidic conditions 3.1: sulfuric acid / 1,4-dioxane; water / 5 h / 95 - 100 °C 4.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 2 h 4.2: 1 h / 25 - 30 °C 4.3: 2 h / 40 - 45 °C

	Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 - 105 °C 3.1: sodium hydrogencarbonate; sodium hypochlorite; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0 - 5 °C 4.1: acetic acid / methanol / 1 h / 20 °C 4.2: 25 - 45 °C 5.1: sodium hydroxide; water / methanol / 6 h / 20 °C 6.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C
	Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 - 105 °C 3.1: triethylamine; oxalyl dichloride / dichloromethane; dimethyl sulfoxide / -70 - -50 °C 4.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 2 h 4.2: 1 h / 25 - 30 °C 4.3: 2 h / 40 - 45 °C
	Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 115 - 120 °C 3.1: water; sulfuric acid / 1,4-dioxane / 5 h / 95 - 100 °C 4.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 2 h 4.2: 1 h / 25 - 30 °C 4.3: 2 h / 40 - 45 °C
	Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 - 105 °C 3.1: triethylamine; oxalyl dichloride / dichloromethane; dimethyl sulfoxide / -70 - -50 °C 4.1: acetic acid / methanol / 1 h / 20 °C 4.2: 3 h / 25 - 45 °C 5.1: sodium hydroxide; water / methanol / 6 h / 20 °C 6.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C
	Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 0.5 h / -20 - -10 °C 2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 115 - 120 °C 3.1: water; sulfuric acid / 1,4-dioxane / 5 h / 95 - 100 °C 4.1: acetic acid / methanol / 1 h / 20 °C 4.2: 3 h / 25 - 45 °C 5.1: sodium hydroxide; water / methanol / 6 h / 20 °C 6.1: sodium hydroxide; dihydrogen peroxide / dimethyl sulfoxide / 6 h / 20 °C

Reference： [1]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - WO2011/30356, 2011, A2
[2]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - WO2011/30356, 2011, A2
[3]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - WO2011/30356, 2011, A2
[4]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - WO2011/30356, 2011, A2
[5]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - US2012/165548, 2012, A1
[6]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - US2012/165548, 2012, A1
[7]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - US2012/165548, 2012, A1
[8]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - US2012/165548, 2012, A1

5
[ 106854-74-4 ]
[ 160969-03-9 ]

Reference： [1]Patent: WO2011/101864,2011,A1

6
[ 106854-74-4 ]
[ 160969-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 2 h 2: potassium carbonate; potassium iodide / acetone / 48 h / 60 °C

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H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
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. 106854-74-4 ] {[proInfo.proName]}

Quality Control of [ 106854-74-4 ]

Related Doc. of [ 106854-74-4 ]

Product Details of [ 106854-74-4 ]

Safety of [ 106854-74-4 ]

Application In Synthesis of [ 106854-74-4 ]

[ 106854-74-4 ] Synthesis Path-Upstream 1~2

[ 106854-74-4 ] Synthesis Path-Downstream 1~6

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry