[ CAS No. 461-96-1 ] {[proInfo.proName]}

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Quality Control of [ 461-96-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 461-96-1 ]

SDS Specification

Alternatived Products of [ 461-96-1 ]

Product Details of [ 461-96-1 ]

CAS No. :	461-96-1	MDL No. :	MFCD00010305
Formula :	C₆H₃BrF₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	JHLKSIOJYMGSMB-UHFFFAOYSA-N
M.W :	192.99	Pubchem ID :	136313
Synonyms :

Calculated chemistry of [ 461-96-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.06
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
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) :	-5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.16
Log Po/w (XLOGP3) :	2.81
Log Po/w (WLOGP) :	3.57
Log Po/w (MLOGP) :	3.91
Log Po/w (SILICOS-IT) :	3.38
Consensus Log Po/w :	3.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.0967 mg/ml ; 0.000501 mol/l
Class :	Soluble
Log S (Ali) :	-2.47
Solubility :	0.658 mg/ml ; 0.00341 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.81
Solubility :	0.0298 mg/ml ; 0.000155 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 461-96-1 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P260-P264-P270-P272-P273-P280-P301+P312+P330-P303+P361+P353-P314-P333+P313-P370+P378-P391-P403+P235-P501	UN#:	1993
Hazard Statements:	H225-H302-H315-H317-H373-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 461-96-1 ]

* 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 [ 461-96-1 ]
Downstream synthetic route of [ 461-96-1 ]

[ 461-96-1 ] Synthesis Path-Upstream 1~2

1
[ 461-96-1 ]
[ 144261-13-2 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 899 - 910
[2] Patent: JP6085912, 2017, B2,

2
[ 461-96-1 ]
[ 40649-36-3 ]
[ 144261-13-2 ]

Reference： [1] Patent: US2014/275577, 2014, A1,

[ 461-96-1 ] Synthesis Path-Downstream 1~6

1
[ 461-96-1 ]
[ 160976-02-3 ]

Reference： [1]Helvetica Chimica Acta,2003,vol. 86,p. 2671 - 2686
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 187 - 191
Angew. Chem.,2018,vol. 130,p. 193 - 197,5
[3]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1553 - 1560

2
[ 6704-31-0 ]
[ 461-96-1 ]
[ 1395281-64-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	In tetrahydrofuran; ethyl acetate;	Synthesis of 3-(3,5-difluorophenyl)oxetan-3-ol To a solution of 1-bromo-3,5-difluorobenzene in THF (0.27 M) under Ar was added Mg turnings (1.6 M). A reflux condenser was attached and the solution was submerged in a 90 C. oil bath and refluxed for two hours. The oxetan-3-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar overnight. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-100% EtOAc/n-heptanes gradient) to yield 3-(3,5-difluorophenyl)oxetan-3-ol in 56% yield. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.82 (d, J=7.63 Hz, 2H), 4.91 (d, J=7.63 Hz, 2 H), 7.16-7.23 (m, 2H).
56%		To a solution of 1-bromo-3,5-difluorobenzene in THF (0.27 M) under Ar was added Mg turnings (1.6 M). A reflux condenser was attached and the solution was submerged in a 90 C. oil bath and refluxed for two hours. The oxetan-3-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar overnight. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-100% EtOAc/n-heptanes gradient) to yield 3-(3,5-difluorophenyl)oxetan-3-ol in 56% yield. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.82 (d, J=7.63 Hz, 2H), 4.91 (d, J=7.63 Hz, 2 H), 7.16-7.23 (m, 2H).
56%		To a solution of 1-bromo-3,5-difluorobenzene in THF (0.27 M) under Ar was added Mg turnings (1.6 M). A reflux condenser was attached and the solution was submerged in a 90 C. oil bath and refluxed for two hours. The oxetan-3-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar overnight. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-100% EtOAc/n-heptanes gradient) to yield 3-(3,5-difluorophenyl)oxetan-3-ol in 56% yield. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.82 (d, J=7.63 Hz, 2H), 4.91 (d, J=7.63 Hz, 2 H), 7.16-7.23 (m, 2H).

56%		Synthesis of 3-(3,5-difluorophenyl)oxetan-3-ol To a solution of l-bromo-3,5-difluorobenzene in THF (0.27 M) under Ar was added Mg turnings (1.6 M). A reflux condenser was attached and the solution was submerged in a 90 C oil bath and refluxed for two hours. The oxetan-3-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar overnight. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sat), dried over MgS04, filtered, concentrated and purified by ISCO Si02 chromatography (0-100%) EtOAc/n-heptanes gradient) to yield 3-(3,5-difluorophenyl)oxetan-3-ol in 56% yield. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.82 (d, J=7.63 Hz, 2 H), 4.91 (d, J=7.63 Hz, 2 H), 7.16 - 7.23 (m, 2 H).
56%		To a solution of l-bromo-3,5-difluorobenzene in THF (0.27 M) under Ar was added Mg turnings (1.6 M). A reflux condenser was attached and the solution was submerged in a 90 C oil bath and refluxed for two hours. The oxetan-3-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar overnight. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sat.), dried over MgS04, filtered, concentrated and purified by ISCO Si02 chromatography (0-100% EtOAc/n-heptanes gradient) to yield 3-(3,5- difhiorophenyl)oxetan-3-ol in 56% yield. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.82 (d, J=7.63 Hz, 2 H), 4.91 (d, J=7.63 Hz, 2 H), 7.16 - 7.23 (m, 2 H).
56%		Synthesis of 3-(3,5-difluorophenyl)oxetan-3-ol To a solution of l-bromo-3,5-difluorobenzene in THF (0.27 M) under Ar was added Mg turnings (1.6 M). A reflux condenser was attached and the solution was submerged in a 90 C oil bath and refluxed for two hours. The oxetan-3-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar overnight. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sa ), dried over MgS04, filtered, concentrated and purified by ISCO Si02 chromatography (0-100%) EtOAc/n-heptanes gradient) to yield 3-(3,5-difluorophenyl)oxetan-3-ol in 56% yield. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.82 (d, J=7.63 Hz, 2 H), 4.91 (d, J=7.63 Hz, 2 H), 7.16 - 7.23 (m, 2 H).

Reference： [1]Patent: US2012/225061,2012,A1
[2]Patent: US2012/225062,2012,A1 .Location in patent: Page/Page column 39
[3]Patent: US2012/225061,2012,A1 .Location in patent: Page/Page column 38
[4]Patent: WO2014/33631,2014,A1 .Location in patent: Page/Page column 52
[5]Patent: WO2014/33630,2014,A1 .Location in patent: Page/Page column 64
[6]Patent: WO2014/99880,2014,A1 .Location in patent: Page/Page column 161

3
[ 22929-52-8 ]
[ 461-96-1 ]
3-(3,5-difluorophenyl)tetrahydrofuran-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.7%	In tetrahydrofuran; n-heptane; ethyl acetate;	Intermediate 142 3-(3,5-difluorophenyl)tetrahydrofuran-3-ol to a solution of 1-bromo-3,5-difluoro-benzene (4.00 g, 20.7 mmol) in tetrahydrofuran (70 mL) under nitrogen was added magnesium (6.0 equiv., 124 mmol) and the solution was heated at 85° C. for three hours. The solution was cooled to rt and 3-oxotetrahydrofuran (1 equiv., 20.726 mmol) in THF (20 mL) was added via syringe. The mixture was stirred at rt for three days. The reaction was quenched with sat NaHCO3, extracted with EtOAc and washed with brine. Purification by CombiFlash (0 to 100percent EtOAc in heptane) provided the title compound (405 mg, 9.7percent).
9.7%		To a solution of l-bromo-3,5-difluoro-benzene (4.00 g, 20.7 mmol) in tetrahydrofuran (70 mL) under nitrogen was added magnesium (6.0 equiv., 124 mmol) and the solution was heated at 85 °C for three hours. The solution was cooled to room temperature (rt) and 3- oxotetrahydrofuran (1 equiv., 20.726 mmol) in THF (20 mL) was added via syringe. The mixture was stirred at rt for three days. The reaction was quenched with sat NaHCOs, extracted with EtOAc and washed with brine. Purification by CombiFlash (0 to 100percent EtOAc in heptane) provided the title compound (405 mg, 9.7percent).

Reference： [1]Patent: US2014/88117,2014,A1 .Location in patent: Page/Page column
[2]Patent: WO2015/140189,2015,A1 .Location in patent: Page/Page column 125

4
[ 461-96-1 ]
[ 121554-09-4 ]
3,5-difluoro-4-(n-octyloxy)biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 90℃; for 20h;Inert atmosphere;	2.4g (13mmol) of 1-bromo-3,5-difluoro-benzene, 3.2g (13mmol) of 4- (1-octyl) phenyl boronic acid, tris (2, 0.24g (0.80mmol) - methylphenyl) phosphine into a 200mL three-necked flask was replaced with nitrogen the flask. 2.0M aqueous solution of potassium carbonate in 13mL of a mixture, 31mL of toluene, was added 31mL of ethanol, was degassed by stirring under reduced pressure. To this mixture was added palladium acetate (II) of 29mg (0.13mmol) and stirred at 90 for 20 hours under a nitrogen flow. After a predetermined time elapses, the aqueous layer of the obtained mixture was performed by the toluene extraction. After combining the resulting extraction solution and the organic layer was washed with saturated brine, and dried over magnesium sulfate. Separated by the mixture to the natural filtration, the filtrate was concentrated to give a light brown solid. Methanol was added to the obtained solid, and applying ultrasonic waves, and the solid was collected by suction filtration. The resulting solid was purified by silica gel column (developing solvent: hexane) was purified by using a. By concentration of the resulting peusyeon, into the target product, 3,5-difluoro -4- (n- octyl-1-oxy)biphenyl to obtain a white solid in quantities of 3.1g, 78% yield

Reference： [1]Patent: KR2015/15418,2015,A .Location in patent: Paragraph 0205-0208

5
[ 56309-94-5 ]
[ 461-96-1 ]
C₂₀H₂₆F₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.4 g	With magnesium; In tetrahydrofuran; at 50℃; for 1h;Cooling;	First Step (0184) To a THF suspension (10 mL) of magnesium (4.5 g, 186.5 mmol), a THF solution (90 mL) of compound (e-1) (30.0 g, 155.5 mmol) was slowly added dropwise while liquid temperature was kept at 50° C. or less. To a Grignard reagent cooled in a water bath, a THF solution (80 mL) of compound (e-2) (40.8 g, 171.0 mmol) was slowly added dropwise while liquid temperature was kept at 50° C. or less. The resulting reaction mixture was stirred at room temperature for 1 hour and then quenched by an ammonium chloride solution, and the resulting mixture was subjected to extraction with ethyl acetate (400 mL). Combined organic layers were washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then a solvent was distilled off to obtain compound (e-3) (48.4 g, 137.4 mmol).

Reference： [1]Patent: US2016/280997,2016,A1 .Location in patent: Paragraph 0183; 0184

6
[ 461-96-1 ]
[ 1082549-89-0 ]

Reference： [1]Patent: CN109320449,2019,A
[2]Patent: US2019/229276,2019,A1
[3]Patent: KR2019/78763,2019,A
[4]Dyes and Pigments,2020,vol. 180

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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
H270	May cause or intensify fire; oxidizer
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

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[ CAS No. 461-96-1 ] {[proInfo.proName]}

Quality Control of [ 461-96-1 ]

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[ 461-96-1 ] Synthesis Path-Upstream 1~2

[ 461-96-1 ] Synthesis Path-Downstream 1~6

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Fluorinated Building Blocks

Aryls

Bromides

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[ 461-96-1 ]