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[ CAS No. 105942-08-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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Chemical Structure| 105942-08-3

Chemical Structure| 105942-08-3

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Quality Control of [ 105942-08-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 105942-08-3 ]

SDS Specification

Alternatived Products of [ 105942-08-3 ]

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Product Details of [ 105942-08-3 ]

CAS No. :	105942-08-3	MDL No. :	MFCD00143264
Formula :	C₇H₃BrFN	Boiling Point :	No data available
Linear Structure Formula :	BrC₆H₃(F)(CN)	InChI Key :	HGXWRDPQFZKOLZ-UHFFFAOYSA-N
M.W :	200.01	Pubchem ID :	736029
Synonyms :

Calculated chemistry of [ 105942-08-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
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 :	38.81
TPSA :	23.79 ?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) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	2.43
Log Po/w (WLOGP) :	2.88
Log Po/w (MLOGP) :	2.63
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.05
Solubility :	0.176 mg/ml ; 0.000881 mol/l
Class :	Soluble
Log S (Ali) :	-2.57
Solubility :	0.535 mg/ml ; 0.00268 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.62
Solubility :	0.0481 mg/ml ; 0.00024 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 105942-08-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 105942-08-3 ]

* 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 [ 105942-08-3 ]
Downstream synthetic route of [ 105942-08-3 ]

[ 105942-08-3 ] Synthesis Path-Upstream 1~5

1
[ 201230-82-2 ]
[ 105942-08-3 ]
[ 176508-81-9 ]

Reference： [1] Patent: WO2005/123688, 2005, A2, . Location in patent: Page/Page column 68

2
[ 105942-08-3 ]
[ 79-19-6 ]
[ 299937-74-9 ]

Reference： [1] Patent: WO2006/38100, 2006, A1, . Location in patent: Page/Page column 68

3
[ 105942-08-3 ]
[ 108-95-2 ]
[ 875664-25-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: With potassium carbonate In N,N-dimethyl-formamide; toluene for 4 h; Dean-Stark; Inert atmosphere; Reflux Stage #2: for 4 h; Reflux; Inert atmosphere	In a three-neck flask equipped with a Dean-Stark trap, phenol (12.35 g, 131.25 mmol), K₂CO₃(34.55 g, 250 mmol), N,N-dimethylformamide (125 mL) and toluene (125 mL) were charged, and refluxed in a nitrogen atmosphere for 4 hours to perform dehydration until no further water was formed from the reaction system. Thereafter, 100 mL of toluene was removed with the Dean-Stark trap. (0176) After returning to room temperature, 4-bromo-2-fluorobenzonitrile (25.0 g, 125 mmol) was added thereto, and the mixture was refluxed in a nitrogen atmosphere for 4 hours. After completing the reaction, the solution was diluted by adding toluene (200 mL) thereto, and then filtered with Celite. The solution was rinsed twice with water with a separating funnel, dried over anhydrous magnesium sulfate, and filtered. The product was purified by silica gel chromatography (mobile phase: toluene/ethyl acetate=9/1), and a specimen deposited through concentration of the solution was rinsed with 200 mL of hexane under application of ultrasonic wave for 5 minutes, and then filtered. The specimen was dried in vacuum (50° C. for 4 hours) to provide a white solid matter (yield amount: 31.2 g, yield: 91percent). The product was identified by ¹H-NMR and ESI-MS. (0177) ¹H NMR (500 MHz, CDCl₃, δ): 6.97 (s, 1H), 7.11 (d, 2H), 7.25-7.31 (m, 2H), 7.42-7.48 (m, 2H), 7.51 (d, 1H) (0178) ESI-MS (m/z) (M⁺) calcd. 272.98, found 273.09.

Reference： [1] Patent: US9685615, 2017, B2, . Location in patent: Page/Page column 85-86
[2] Patent: US2006/135524, 2006, A1, . Location in patent: Page/Page column 23
[3] Patent: WO2007/30089, 2007, A1, . Location in patent: Page/Page column 85
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 44, p. 13809 - 13813[5] Angew. Chem., 2017, vol. 129, # 44, p. 13997 - 14001,5
[6] Organic Letters, 2019, vol. 21, # 1, p. 10 - 13
[7] Patent: CN108997299, 2018, A, . Location in patent: Paragraph 0053; 0054

4
[ 139-02-6 ]
[ 105942-08-3 ]
[ 875664-25-8 ]

Reference： [1] Patent: US2006/135522, 2006, A1, . Location in patent: Page/Page column 19

5
[ 623-50-7 ]
[ 105942-08-3 ]
[ 887250-14-8 ]

Reference： [1] Patent: EP1849465, 2007, A1, . Location in patent: Page/Page column 70

[ 105942-08-3 ] Synthesis Path-Downstream 1~6

1
[ 105942-08-3 ]
[ 146014-66-6 ]
[ 1026635-99-3 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7980 - 7997
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2791 - 2795
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 272 - 282

2
[ 50670-64-9 ]
[ 105942-08-3 ]
[ 1016641-71-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium tert-butylate; In dimethyl sulfoxide; at 20℃; for 0.5h;	Example 21 : Scheme G4; Potassium tert-butoxide (2.1 equiv., 104 mmol, 12.0 g) was added to a stirred solution of 4-bromo-2-fluorobenzonitrile (G4.1) (1 equiv., 49 mmol, 10.0 g) and 5-amino-2- methylbenzonitrile (1 equiv., 49 mmol, 6.7 g) in DMSO (60 ml). The reaction mixture was stirred at room temperature for 0.5 h. Water was added, the resulting precipitate was filtered off, washed successively with water, isopropanol and isopropyl ether to give G4.2 (9.9 g, yield = 64%).

Reference： [1]Patent: WO2008/37784,2008,A1 .Location in patent: Page/Page column 54

3
[ 105942-08-3 ]
[ 112734-22-2 ]

Yield	Reaction Conditions	Operation in experiment
5 mmol	With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 16h;	4-Bromo-2-fluorobenzonitrile (5.00 mmol) in THF (30 mL)was cooled to 0 °C. A borane tetrahydrofuran complexsolution (1 M in THF, 15.0 mL) was added dropwise. Thesolution was stirred at 0 °C for 20 mm before being broughtup to RT and stirred for 16 h. MeOH was added dropwise (30 mL) and the solution was concentrated under reduced pressure. The residue was partitionedbetween an aqueous solution of NaOH (1 M) and EtOAc. The organic layer was worked up to give the titled compound (5.00 mmol) as a yellow oil. 1H NMR (400 MHz, CDCI3, ): 7.42-7.27 (m, 1H), 7.25-7.16 (m, 2H), 3.65 (t, J = 6.6 Hz, 2H).
	With borane-THF; In tetrahydrofuran; at 0 - 60℃; for 0.5h;	A solution of 100.00 mg Compound BD2-1 (i.e., 4-bromo-2-fluorobenzonitrile) in THF (2.00 mL) was cooled to 0°C. Then BH3-THF (1 M, 1.50 mL) was added and stirred at 60°C for 0.5 hour. LCMS showed the reaction was completed. The reaction mixture was diluted by addition of MeOH (3 mL) and then concentrated under reduced pressure to afford Compound BD2-2 (100.00 mg, crude) as a red oil.

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1898 - 1905
[2]Journal of Organic Chemistry,2009,vol. 74,p. 1964 - 1970
[3]Patent: WO2017/103611,2017,A1 .Location in patent: Paragraph 00336
[4]Patent: WO2018/75871,2018,A1 .Location in patent: Page/Page column 62

4
[ 53903-49-4 ]
[ 105942-08-3 ]
[ 1360431-01-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In toluene; at 110℃; for 20h;Inert atmosphere;	<strong>[53903-49-4]2-Amino-5-methoxy-benzotrifluoride</strong> (10.46 mmol), K3PO4 (15.7 mmol), Xphos (1.05 mmol) and Pd4(dba)3 (0.314 mmol) were added under nitrogen to a solution of 4-bromo-2-fluoro-benzonitrile (10.46 mmol) in 50 mL toluene and the mixture was stirred for 20 hours at a bath temperature of 110 C. Then the mixture was filtered through a glass fibre filter, then the filtrate was extracted with 150 mL water. The organic phase was dried on sodium sulphate and evaporated down. In this way the product was obtained in a yield of 87% of theory. C15H10F4N2O (310.2) Mass spectrum (ESI): [M+H]+=311 [M-H]-=309 Thin layer chromatograph (silica gel; petroleum ether/ethyl acetate 7:3): Rf=0.48

Reference： [1]Patent: US2012/208823,2012,A1 .Location in patent: Page/Page column 17

5
[ 105942-08-3 ]
[ 133773-29-2 ]
[ 1441793-39-0 ]

Yield	Reaction Conditions	Operation in experiment
3.4 g	With triethylamine; In dimethyl sulfoxide; at 120℃; for 20h;	To a solution of 4-bromo-2-fluoro-benzonitrile (2.0 g, 10.0 mmol) and (LR)-l- (2,4-dichlorophenyl)ethanamine (1.9 g, 10.0 mmol) in dimethyl sulfoxide (DMSO) (4 mL) was added triethylamine (1.45 g, 14.3 mmol). The reaction mixture was heated at 120 C for 20 h. After cooling to room temperature, the mixture was diluted with deionized water and a brown gummy material was obtained. The aqueous layer was decanted off, and the gum was dissolved in ethyl acetate, washed with deionized water, and brine. The organic layer was dried (Na2S04), filtered, and concentrated in vacuo. The crude product was used without further purification ((3.4 g, 9.2 mmol, 92%).

Reference： [1]Patent: WO2013/82490,2013,A1 .Location in patent: Paragraph 0140

6
[ 105942-08-3 ]
[ 175883-62-2 ]
C₁₅H₁₂FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A reaction mixture of 2a-e (5.0 mmol, 1.0 equiv.), differentsubstituted 4-bromobenzonitrile (6.0 mmol, 1.2 equiv.) and potassiumcarbonate (12.5 mmol, 2.5 equiv.) in PEG400/H20 (10 mL/10 mL) was stirred at room temperature for 15 min, and PdCl2(0.05 mmol, 0.01 equiv.) was subsequently added. Stirring wascontinued for an additional 15 h until complete consumption ofstarting material as judged by TLC. Then the reaction mixture waspoured into water (80 mL) and extracted with ethyl acetate(30 mL*3). The organic layers were washed with brine, dried overanhydrous Na2SO4, filtered and condensed under reduced pressure.The residuewas then purified via column chromatography on silicagel, eluting with EtOAc/petroleum ether to 3a-r as white solid.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 182
[2]Journal of Medicinal Chemistry,2019

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction ? 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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