[ CAS No. 104197-14-0 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 104197-14-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 104197-14-0 ]

SDS Specification

Alternatived Products of [ 104197-14-0 ]

Product Details of [ 104197-14-0 ]

CAS No. :	104197-14-0	MDL No. :	MFCD01631351
Formula :	C₇H₅BrF₂O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	CDOQKISJPOWBKC-UHFFFAOYSA-N
M.W :	223.01	Pubchem ID :	2773287
Synonyms :

Calculated chemistry of [ 104197-14-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.55
TPSA :	9.23 ?2

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) :	-5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.36
Log Po/w (XLOGP3) :	2.79
Log Po/w (WLOGP) :	3.58
Log Po/w (MLOGP) :	3.41
Log Po/w (SILICOS-IT) :	3.34
Consensus Log Po/w :	3.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.32
Solubility :	0.107 mg/ml ; 0.000481 mol/l
Class :	Soluble
Log S (Ali) :	-2.64
Solubility :	0.511 mg/ml ; 0.00229 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.94
Solubility :	0.0254 mg/ml ; 0.000114 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 104197-14-0 ]

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

Application In Synthesis of [ 104197-14-0 ]

* 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 [ 104197-14-0 ]
Downstream synthetic route of [ 104197-14-0 ]

[ 104197-14-0 ] Synthesis Path-Upstream 1~1

1
[ 104197-14-0 ]
[ 363-47-3 ]

Reference： [1] Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688

[ 104197-14-0 ] Synthesis Path-Downstream 1~10

1
[ 104197-14-0 ]
3',5'-difluoro-4'-hydroxy-biphenyl-4-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 355 - 374

2
[ 104197-14-0 ]
3',5'-difluoro-4'-hydroxy-biphenyl-3-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 355 - 374

3
[ 104197-14-0 ]
3',5'-difluoro-4'-hydroxy-biphenyl-4-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 355 - 374

4
[ 104197-14-0 ]
3',5'-difluoro-4'-hydroxy-biphenyl-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 355 - 374

5
[ 868263-37-0 ]
[ 104197-14-0 ]
[2-(3-tert-butyl-3',5'-difluoro-4'-methoxybiphenyl-4-yloxy)ethyl]-methylamino}-acetic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 20℃;Heating / reflux;	Stir a mixture of (12-[2-tert-butyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2- yl) -phenoxy]ethyl}-methylamino)-acetic acid tert-butyl ester prepared essentially as decribed in Preparation 180 (0.4 mg, 0.89 mmol, leq), potassium phosphate (5 eq) and [1,1'bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.1 eq) in 1,2- dimethoxyethane for 15 min at room temperature under nitrogen and add 4-bromo-2,6- difluoroanisole (1.5 eq) in 1,2-dimethoxyethane. Heat to reflux over night under nitrogen. Add extra <strong>[104197-14-0]4-bromo-2,6-difluoroanisole</strong> (0.75 eq), potassium phosphate (2.5 eq) and [1,1'bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.05eq) in 1,2- dimethoxyethane (5 mL) and heat for a further 24 h. Cool to room temperature, filter inorganics on Celite washing with methanol and concentrate. Take up residue in methanol and purify (ion exchange chromatography, eluting with 2 M ammonia in methanol, followed by automated Isco chromatography, eluting with solvent gradient 0:100 to 30:70 cyclohexane:ethyl acetate) to give the title compound as a oil (123 mg, 30%). LC-MS: m/z=464.2

Reference： [1]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 93

6
[ 104197-14-0 ]
[ 73183-34-3 ]
[ 890839-37-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; dichloromethane; at 80℃; for 12.5h;Inert atmosphere;	Intermediate 112 2-(3,5-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa borolane To a solution of intermediate 111 (2.0 g, 8.968 mmoles) in Dioxan (40 ml), bis(pinacaloto)diboron (2.73 g, 10.76 mmoles) and potassium acetate (2.64 g, 26.90 mmoles) were added and the system is degassed for 30 min Bis(diphenylphosphinoferrocene)dichloro palladium.CH2Cl2 (0.219 g, 0.269 mmoles) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as yellow liquid (2.2 g, 90% yield).). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta delta 7.318 (d, J=8.7 Hz, 2H), 4.02 (s, 3H), 1.32 (s, 12H).
24%	With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 16h;	Example VIII2,6-Difluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)anisolTo a solution of <strong>[104197-14-0]4-bromo-2,6-difluoro-anisol</strong> (3.0 g) in dry dioxane (50 mL) and under argon atmosphere is added bis(pinacolato)diboron (5.13 g), potassium acetate (3.94 g), 1 ,1 '- bis(diphenylphosphino)-ferrocene (0.55 g) and 1 ,1'-bis(diphenylphosphino)- ferrocenedichloropalladium (II) (0.82 g). The flask is tightly sealed and heated to 80 0C for 16 h. Then the reaction mixture is concentrated under reduced pressure and the residue is taken up in ethyl acetate. The resulting mixture is washed with water, dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1 :0->2:1 ).Yield: 0.88 g (24% of theory)Mass spectrum (ESI+): m/z = 271 [M+H]+
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 150℃; for 0.333333h;Microwave irradiation;	Preparation 14. 2-r3,5-difluoro-4-(methyloxy)phenylH,4,5,5-tetramethyl-1.3,2- dioxaborolane; A solution of <strong>[104197-14-0]4-bromo-2,6-difluoroanisole</strong> (223mg, 1 mmole), bis(pinacaolato)diboron (275 mg, 1.09 mmole), [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (40 mg) and KOAc (300 mg) in 5 ml of dioxane was heated in the microwave at 150 for 20 minutes. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and evaporated. The residue was chromatographed on a Florisil column, and the titled compound was eluted with Et20, 158 mg (58%). 1H NMR (400 MHz, CDCI3) delta 7.32 (d, J=8Hz, 2H), 4.05 (s, 3H), 1.35 (s, 12H).

Reference： [1]Patent: US2011/118257,2011,A1 .Location in patent: Page/Page column 100
[2]Patent: WO2008/34859,2008,A1 .Location in patent: Page/Page column 40
[3]Patent: WO2006/63167,2006,A1 .Location in patent: Page/Page column 33

7
[ 104197-14-0 ]
6-bromo-2,4-difluoro-3-methoxy-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; phosphoric acid; In tetrahydrofuran; methanol; water;	EXAMPLE 197 2,4-Difluoro-3-methoxy-benzoic acid A solution of <strong>[104197-14-0]5-bromo-1,3-difluoro-2-methoxy-benzene</strong> (12.35 g, 55.4 mmole, L. I. Kruse, et al., Biochemistry 1986, 25, 7271-7278) in anhydrous tetrahydrofuran (350 mL) was transferred via canulla into a 1 L flask which had been flame dried. The solution was cooled to -80 C. and a solution of n-butyl lithium (2.5 M in hexanes, 24.35 mL, 60.9 mmol) was added dropwise via syringe pump over a 1 hour period with stirring under a dry nitrogen atmosphere. After stirring 2.5 hours, dry carbon dioxide gas was bubbled into the cold reaction mixture for 0.5 hour. The solution was then poured onto crushed dry ice and strirred for 0.5 hours. The mixture was causiously added to water (600 mL) and acidified with 10% HCl. The organics were extracted with ether. The extracts were combined and washed with brine. After concentrating and standing at room temperature for two days the residue was redissolved in ether and combined with acid treated (2% H3PO4 in methanol) silica gel. The solvent was removed and the adsorbate was flash chromatographed to give the title compound as an off-white solid: mp 191-192 C.: NMR (400 MHz, DMSO-d6); delta13.37 (broad singlet, 1 H), 7.63-7.58 (m, 1 H,), 7.25 - 7.20 (m, 1 H), 3.92(s, 3 H); MS (+FAB): (M+H): 189 (12%), 154 (100%), 136 (75%); Anal. Calc. for C8H6F2O3: C, 51.08; H, 3.21. Found: C, 50.98, H, 3.15. Concentration of less polar fractions gave 6-bromo-2,4-difluoro-3-methoxy-benzoic acid (3.44 g, 23%) as a white solid: mp 92-94 C.: NMR (400MHz, DMSO-d6); delta14.18 (broad singlet, 1 H), 7.65 (dd, J=3, 1 Hz, 1 H), 3.94 (s, 3 H); MS: (+FAB) (M +H: 267/269 (38%), 91 (100%); Anal. calc. for C8H5BrF2O3: C, 35.98, H, 1.89, N, 0.00. Found: C, 36.26, H, 1.79, N 0.03.

Reference： [1]Patent: US6110962,2000,A

Yield	Reaction Conditions	Operation in experiment
		PREPARATION EXAMPLE 17 Preparation of Compound (17) 2,6-Difluorophenol is brominated and then reacted with methyl iodide, etc. to obtain 4-bromo-2,6-difluoroanisole, which is led to compound (17) in the same manner as in Preparation Example 13.
		A phenol derivative of formula (P22): STR100 is obtained using the resulting 4-bromo-2,6-difluoroanisole, which is then led to compound (35) in the same manner as in Preparation Example 31.

9
[ 104197-14-0 ]
[ 57260-71-6 ]
[ 909418-83-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; johnphos; sodium t-butanolate; In toluene; at 90℃; for 16h;	A mixture of <strong>[104197-14-0]4-bromo-2,6-difluorophenyl methyl ether</strong> (5.Og), 1 ,1-dimethylethyl 1- piperazinecarboxylate (5.Og), 2-biphenylyl[bis(1 ,1-dimethylethyl)]phosphane (0.666g), palladium acetate (0.246g), sodium tert-butoxide (3.01 g) in toluene(30ml) was heated at 9O0C for 16 hours. After cooling ,The reaction mixture was diluted with diethyl ether, filtered through a pad of celite. Then concentrated in vacuo to give a black oil. The desired product was isolated by column chromatography on silica eluting with a gradient of 5 to 100% ethyl acetate in pentane. The title compound was obtained as a solid, (90% yield), LC/MS (ESI) Found 229 (M-BOC+1 ).

Reference： [1]Patent: WO2006/94842,2006,A1 .Location in patent: Page/Page column 59-60

10
[ 544-92-3 ]
[ 104197-14-0 ]
[ 104197-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 120℃; for 48h;	(iii) 3 ,5-Difluoro-4-methoxybenzonitrileA mixture of 4-bromo-2,6-difluororhohenyl methyl ether (11.5 g, 0.0516 mol; see step (ii) above) and CuCN (6.92 g, 0.0774 mol) in dry DMF (15 mL) was stirred at 120C for two days under nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by column chromatography over silica gel, using 2% ethyl acetate in petroleum ether as eluent, yielded 2.7 g of the sub-title compound as a pale yellow solid.

Reference： [1]Patent: WO2006/135316,2006,A1 .Location in patent: Page/Page column 55

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Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Nomenclature of Ethers ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions of Ethers ? Reimer-Tiemann Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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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. 104197-14-0 ] {[proInfo.proName]}

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