[ CAS No. 139911-29-8 ] {[proInfo.proName]}

Name: 139911-29-8|2-Methyl-4-fluorophenylboronic acid|98%
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SKU: A144806
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Quality Control of [ 139911-29-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 139911-29-8 ]

Product Details of [ 139911-29-8 ]

CAS No. :	139911-29-8	MDL No. :	MFCD17214439
Formula :	C₇H₈BFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQMLIVUHMSIOQP-UHFFFAOYSA-N
M.W :	153.95	Pubchem ID :	2734665
Synonyms :		Chemical Name :	2-Methyl-4-fluorophenylboronic acid

Calculated chemistry of [ 139911-29-8 ]

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 :	2.0
Molar Refractivity :	41.19
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.29
Log Po/w (WLOGP) :	0.23
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	0.12
Consensus Log Po/w :	0.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.94
Solubility :	1.75 mg/ml ; 0.0114 mol/l
Class :	Very soluble
Log S (Ali) :	-1.74
Solubility :	2.8 mg/ml ; 0.0182 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.94
Solubility :	1.77 mg/ml ; 0.0115 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 139911-29-8 ]

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

Application In Synthesis of [ 139911-29-8 ]

* 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 [ 139911-29-8 ]
Downstream synthetic route of [ 139911-29-8 ]

[ 139911-29-8 ] Synthesis Path-Upstream 1~5

1
[ 5419-55-6 ]
[ 452-63-1 ]
[ 139911-29-8 ]

Yield	Reaction Conditions	Operation in experiment
61.5%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: for 1 h;	In a solution of 2-bromo-5-fluorotoluene (250 g) in tetrahydrofuran (250 ml) and n- hexane (250 ml) was added n-butyl lithium (991.5 ml) drop wise at -78°C in a dry-ice bath. The solution was stirred for an hour. Triisopropyl borate (373.11 g) was added drop wise and reaction was stirred for further an hour. The resulting solution was diluted with aqueous sodium hydroxide and then washed with n-heptane. The pH of the aqueous layer was adjusted to pH 2-3 using hydrochloric acid and then extracted with ethyl acetate. The organic layer was concentrated under vacuum. This was dissolved in ethyl acetate at about 40°C and to this heptane was added to obtain 2- methyl-4-fluorophenylboronic acid. Yield: 61.5percent; HPLC purity: 99.00percent.

Reference： [1] Patent: WO2017/125835, 2017, A1, . Location in patent: Paragraph 00117

2
[ 5419-55-6 ]
[ 452-63-1 ]
[ 7732-18-5 ]
[ 1310-73-2 ]
[ 139911-29-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃;	Fluoro-2-methylphenyl)boronic acidTo a solution of l-bromo-4-fluoro-2-methylbenzene (5 g, 26.45 mmol) in THF (100 mL) was added n-butyllithium (12.7 mL) dropwise at -78°C. Tris(propan-2-yl)borate (10 g, 53.17 mmol) was added dropwise and the reaction was stirred overnight at -78°C in a liquid nitrogen bath. The resulting solution was diluted with aqueous sodium hydroxide (IN, 30 mL) and extracted with ether (2 x 50 mL). The aqueous layers were combined and adjusted to pH 3 with HC1 (3N), extracted with ethyl acetate (3 x 50 mL), and the organic layers were combined and concentrated in vacuo to give (4-fluoro-2-methylphenyl)boronic acid as a white solid (2.1 g, 52 percent).

Reference： [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 248

3
[ 121-43-7 ]
[ 452-63-1 ]
[ 139911-29-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydroxide; n-butyllithium In tetrahydrofuran	Step 1 Preparation of 2-methyl-4-fluorophenyl Boronic Acid 2-Bromo-5-fluorotoluene (52.9 mmol, 10 g) in 400 ml of tetrahydrofuran was cooled to -78° C. and n-butyllithium (2.5 M, 58.2 mmol) was added. The solution was stirred for 20 minutes, trimethoxy borane (3 eq, 0.16 mol) was added, and the reaction was allowed to warm to room temperature overnight. Sodium hydroxide (60 ml of 1.25 M) was added and the reaction was stirred for 30 minutes. The tetrahydrofuran was removed in vacuo. The remaining aqueous layer was diluted and extracted with diethyl ether The aqueous layer was adjusted to pH 3 with 2N HCl and extracted with ethyl acetate, which was dried (MgSO₄) and concentrated in vacuo to give 6.57 g (81percent) of a colorless solid: MS(FAB) m/e (rel. intensity) 154(48), 136(100).

Reference： [1] Patent: US6274590, 2001, B1,

4
[ 121-43-7 ]
[ 452-63-1 ]
[ 106-93-4 ]
[ 139911-29-8 ]

Reference： [1] Patent: US2003/92712, 2003, A1,

5
[ 139911-29-8 ]
[ 174671-46-6 ]

Reference： [1] Patent: WO2017/125835, 2017, A1, . Location in patent: Paragraph 00117

[ 139911-29-8 ] Synthesis Path-Downstream 1~15

1
[ 3622-23-9 ]
[ 139911-29-8 ]
6-chloro-2-(4-fluoro-2-methyl-phenyl)-benzothiazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3091 - 3094

2
[ 139911-29-8 ]
[ 673456-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 20 h / Heating 2: 0.73 g / N-bromosuccinimide; AIBN / CCl₄ / 16 h / Heating

Reference： [1]Stones, Duane; Manku, Sukhdev; Lu, Xiaosong; Hall, Dennis G. [Chemistry - A European Journal, 2004, vol. 10, # 1, p. 92 - 100]

3
[ 598-54-9 ]
[ 139911-29-8 ]
[ 130735-95-4 ]
2-(4-morpholinyl)-8-(4-fluoro-2-methylphenyl)oxy-4H-1-benzopyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol; dichloromethane;	2-(4-morpholinyl)-8-(4-fluoro-2-methylphenyl)oxy-4H-1-benzopyran-4-one (TGX-184) To a mixture of 2-(4-morpholinyl)-8-hydroxy-4H-1-benzopyran-4-one (77 mg, 0.31 mmol), 4-fluoro-2-methylphenylboronic acid (48 mg, 0.31 mmol) and copper acetate (57 mg, 0.31 mmol) suspended in dichloromethane (3.1 ml) was added triethylamine (216 uL, 1.56 mmol) and the mixture was stirred at room temperature for 24 h. The solvent was removed and the product chromatographed through a silica column with 0-10% methanol in dichloromethane to yield an off white solid (37 mg). 1H-NMR (d6-DMSO 300 MHz): delta 2.27 (s,31), 3.38 (t, 4H, 5 Hz), 3.74 (t, 4H, 5 Hz), 5.51 (s, 1H), 6.7-6.9 (m, 2H), 7.01 (m, 2H), 7.22 (t, 1H, J=9 Hz), 8.55 (dd, 1H, J=9 Hz, 2 Hz).

Reference： [1]Patent: US2003/216389,2003,A1

4
[ 59786-31-1 ]
[ 139911-29-8 ]
[ 873458-21-0 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 70℃; for 1h;	(2) To 120 ml of an N,N-dimethylformamide solution containing 12 g of the compound obtained in the above-mentioned (1) were added 9.3 g of 4-fluoro-2-methylphenylboric acid, 19.6 g of cesium carbonate, 1.12 g of palladium acetate and 2.63 g of triphenylphosphine, and the mixture was stirred at 700C for 1 hour. After completion of the reaction, ethyl acetate and brine were added to the mixture, and insoluble materials were filtered off. The filtrate was washed successively with brine and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n- hexane:ethyl acetate=4:l) to give 7.9 g of methyl 3- (4-fluoro-2- methylphenyl) isonicotinate shown in the following Table 66.

Reference： [1]Patent: WO2006/30984,2006,A1 .Location in patent: Page/Page column 57; 129

5
[ 139911-28-7 ]
[ 144-55-8 ]
[ 497-19-8 ]
[ 139911-29-8 ]
ethyl 2-(2-methyl-4-fluorophenyl)-5-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.4 g (92%)	tetrakis(triphenylphosphine)palladium (0); In ethanol; toluene;	Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(0) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of <strong>[139911-28-7]ethyl 2-bromo-5-fluorobenzoate</strong> (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mL each of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate and the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta 7.7 (dd, 1 H), 7.5 (m, 1 H), 7.25- 6.75 (m, 4 H), 4.0 (q, 2 H), 2.0 (s, 3 H), 1.0 (t, 3 H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

Reference： [1]Patent: US5070100,1991,A

6
[ 14221-01-3 ]
[ 139911-28-7 ]
[ 144-55-8 ]
[ 497-19-8 ]
[ 139911-29-8 ]
ethyl 2-(2-methyl-4-fluorophenyl)-5-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.4 g (92%)	In ethanol; toluene;	Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(O) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of <strong>[139911-28-7]ethyl 2-bromo-5-fluorobenzoate</strong> (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mLeach of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate an the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta7.7 (dd, 1H), 7.5 (m, 1H), 7.25-6.75 (m, 4H), 4.0 (q, 2H), 2.0 (s, 3H), 1.0 (t, 3H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

Reference： [1]Patent: US4864028,1989,A

7
[ 5509-65-9 ]
[ 139911-29-8 ]
[ 33097-11-9 ]
[ 444605-29-2 ]

Yield	Reaction Conditions	Operation in experiment
		4,6-Dich.loro-2-(methylthio)pyrimidin.e-5-carboxaldehyde (40kg) was dissolved in anhydrous THF (200L) at room temperature. Triethylamine (20kg) was added followed by 2,6-difluoroan.iline (26kg) and the reaction mixture was heated at 60-650C for 12h. The mixture was cooled to room temperature. To the mixture was added water (160L) followed by triethylamine (25.6kg), 4-fluoro-2-mcthylbcnzcncboronic acid (33.2kg), palladium acetate (0.8kg, 2mol%) and. triphenylphosphine (1.88kg, 4mol%). The reaction mixture was heated to 65C and stirred vigorously at this temperature for 3h. The mixture was cooled to 55-600C and THF (160L) was added. The bottom aqueous phase was separated at 55-600C. The organic phase was concentrated to200L, methanol (400L) was added and the THF was removed (until <3mol% THF by NMR) by atmospheric distillation, keeping the volume of the solution at ca.600L by adding methanol (600- 800L). The solution was cooled to 55-6O0C and seeded with the title compound (0.16kg). The slurry was stirred at 55C for at least 30 min and then cooled to 2O0C over Ih. The slurry was stirred at 2O0C for at least 2h and filtered. The cake was washed with methanol (160L) followed by MeOH:water (4: 1,120L) and dried in vacuo at 60-650C <n="87"/>overnight to give the title compound (43.8kg) 400MHzNMR in CDCb. Tetramethylsilane as reference at 0.00 ppm. delta(ppm): 2.29 (3 H) s, 2.33 (3 H) s, 6.97 - 7.05 (4 H) m, 7.24 - 7.32 (3 H) m, 9.64 (1 H) s, 10.38 (1 H) s.

Reference： [1]Patent: WO2007/59500,2007,A2 .Location in patent: Page/Page column 85-86

8
[ 5419-55-6 ]
[ 452-63-1 ]
[ 7732-18-5 ]
[ 1310-73-2 ]
[ 139911-29-8 ]

Yield	Reaction Conditions	Operation in experiment
52%		Fluoro-2-methylphenyl)boronic acidTo a solution of l-bromo-4-fluoro-2-methylbenzene (5 g, 26.45 mmol) in THF (100 mL) was added n-butyllithium (12.7 mL) dropwise at -78C. Tris(propan-2-yl)borate (10 g, 53.17 mmol) was added dropwise and the reaction was stirred overnight at -78C in a liquid nitrogen bath. The resulting solution was diluted with aqueous sodium hydroxide (IN, 30 mL) and extracted with ether (2 x 50 mL). The aqueous layers were combined and adjusted to pH 3 with HC1 (3N), extracted with ethyl acetate (3 x 50 mL), and the organic layers were combined and concentrated in vacuo to give (4-fluoro-2-methylphenyl)boronic acid as a white solid (2.1 g, 52 %).

Reference： [1]Patent: WO2012/119046,2012,A2 .Location in patent: Page/Page column 248

9
[ 1124382-72-4 ]
[ 139911-29-8 ]
[ 1262197-62-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 110℃; for 12h;Inert atmosphere;	General procedure: A mixture of <strong>[1124382-72-4]8-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine</strong> (35a) (10 g, 45 mmol), 4-fluoro-phenylboronic acid (12.61 g, 89 mmol), [1,1?-bis(diphenylphosphino)ferrocene] dichloro palladium(II) (2.93 g, 4 mmol) and sodium carbonate solution (2N in water, 44.6 mL, 89 mmol) in 1,4-dioxane (200 mL) was stirred at 110C under nitrogen atmosphere for 12h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The remainder was purified by preparative MPLC (silica gel, PE/ethyl acetate 20:1) to afford the product

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3227 - 3241
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4794 - 4800

10
[ 1160247-93-7 ]
[ 139911-29-8 ]
[ 1674373-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.5h; Sealed tube; Microwave irradiation;	6 Method 6: Synthesis of Intermediate L To a solution of L-1 (800 mg, 3.17 mmol), L-2 (732 mg, 4.76 mmol) and aqueous Na2C03 (2M, 6.3 mL, 12.7 mmol) in DMF (24 mL) is added dichloropalladium 4-ditert- butylphosphanyl-N,N-dimethyl-aniline ( 224 mg, 0.32 mmol). The reaction vial is sealed and heated to 100 °C for 30 min at Biotage microwave reactor. The resulting mixture is diluted with water (10 mL) and ethyl acetate (30 mL). Phases are separated and organics is washed with brine (20 mL). Organic layer is seperated and dried over anhydrous Na2S04, filtered and concentrated. The residue is purified by column chromatography on silica gel (10-50% EtOAc/Heptane) to yield Intermediate L. MS (ES+): m/z 282.0 [M+H]+.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2015/35032, 2015, A1 Location in patent: Page/Page column 56

11
[ 139911-29-8 ]
[ 174671-46-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); bromine; In dichloromethane; at 34 - 37℃; for 6h;	N-bromosuccinimide (144.51 g), AIBN (31.99 g), and catalytic quantity of bromine (2.07 g) was added to a slurry of 2-methyl-4-fluorophenylboronic acid (100.0 g) in methylene dichloride (5000.0 ml) at 34 to 37C. The resulting reaction mixture was heated to reflux for 6 hrs. The reaction mass was washed with water at 33 to 37C. The methylene chloride layer was added to a solution of sodium hydroxide(150.0 gm sodium hydroxide into 1500.0 ml water) at 10 to 20C and the methylene chloride layer was separated. The pH of aqueous layer was adjusted to pH 2-3 with conc.HCl. Compound of formula V:not detected, Compound of formula XIV: 0.9%, purity(HPLC): 98.9%. The solid was filtered and dried in oven at 45 to 50C for 12 h. The crude compound was dissolved in ethyl acetate (450.0 ml)and to this was added charcoal and stirred at 40C for lh. The reaction mass was filtered and concentrated under vacuum. The solid was dissolved in ethanol and to this water (2.5:6.0) was added. The product obtain 5- Fluoro-l,3-dihydro-l-hydroxy-2,l-benzoxaborole was filtered. Purity (HPLC): 99.9%, Compound of formula XIV: Not detected by HPLC. NuMuKappa (300 MHz, DMSO-d6): delta 4.97, 7.13-7.19 , 7. 23-7. 26, 7.73-7.77, 9.24.

Reference： [1]Patent: WO2017/125835,2017,A1 .Location in patent: Paragraph 00117

12
[ 5419-55-6 ]
[ 452-63-1 ]
[ 139911-29-8 ]

Yield	Reaction Conditions	Operation in experiment
61.5%		In a solution of 2-bromo-5-fluorotoluene (250 g) in tetrahydrofuran (250 ml) and n- hexane (250 ml) was added n-butyl lithium (991.5 ml) drop wise at -78C in a dry-ice bath. The solution was stirred for an hour. Triisopropyl borate (373.11 g) was added drop wise and reaction was stirred for further an hour. The resulting solution was diluted with aqueous sodium hydroxide and then washed with n-heptane. The pH of the aqueous layer was adjusted to pH 2-3 using hydrochloric acid and then extracted with ethyl acetate. The organic layer was concentrated under vacuum. This was dissolved in ethyl acetate at about 40C and to this heptane was added to obtain 2- methyl-4-fluorophenylboronic acid. Yield: 61.5%; HPLC purity: 99.00%.

Reference： [1]Patent: WO2017/125835,2017,A1 .Location in patent: Paragraph 00117

13
[ 139911-29-8 ]
[ 5401-94-5 ]
1-(4-fluoro-2-methylphenyl)-5-nitro-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With pyridine; copper diacetate In dichloromethane at 20℃;	Synthetic Procedure for 1-(4-Fluoro-2-Methylphenyl)-5-Nitro-1H-Indazole (17f). The mixture of 5-nitro-1Hindazole(50 mg, 0.31 mmol), 4-fluoro-2-methylphenylboronicacid (94 mg, 0.61 mmol), and cupric acetate (50 mg,0.28 mmol) in pyridine/dichloromethane (0.1 mL/3 mL) wasstirred at room temperature overnight. The solvent was evaporatedin vacuo and the residue was chromatographed on a silicagel column (n-hexane: ethyl acetate = 4: 1) to give1-(4-fluoro-2-methylphenyl)-5-nitro-1H-indazole (17f, 40 mg,48%). 1H NMR (500 MHz, CDCl3): δ 8.84 (s, 1H), 8.44(s, 1H), 8.30 (dd, J = 9.2, 2.1 Hz, 1H), 7.38 (m, 1H), 7.26(m, 1H), 7.17 (m, 1H), 7.11 (m, 1H), 2.11 (s, 3H); MS (ESI):m/z for C14H10FN3O2, found 272 [M + H+].

Reference： [1]Gu, Sujin; Jung, Myoung Eun; Yoon, Ji-Yong; Yoon, Sang-Eun; Lee, Jeong-Ju; Lee, Kwangho; Choi, Gildon; Kim, Nam-Soon; Jeon, Moon-Kook [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 10, p. 1125 - 1138]

14
[ 40396-54-1 ]
[ 139911-29-8 ]
1-(4'-fluoro-2'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylethane-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;	1-([1,1':4',1''-terphenyl]-3-yl)-2-phenylethane-1,2-dione(T-2) General procedure: A dried radius flask was charged with T-1 (115.2 mg, 0.4 mmol, 1.0 equiv.),4-biphenylboronic acid (158.4 mg, 0.8 mmol, 2.0 equiv.), Pd(PPh3)2Cl2(28.08 mg, 0.04 mmol, 10 mol %), K2CO3 (165.6mg, 1.2 mmol, 3 equiv.), H2O (100 μL) and 1,4-dioxane (4.0 mL). Themixture was stirred at 100 °C for 3 h under nitrogen. Upon completion of thereaction as monitored by TLC, the reaction was allowed to cool to roomtemperature, and extracted with ethyl acetate (20 mL × 3). The organic phasewas collected and washed with brine, dried over with anhydrous Na2SO4,ltered, and concentrated. The filtrate was evaporated under reduced pressure,and the residue was purified by column chromatography on silica gel usingpetroleum ether/ethyl acetate as eluent to afford the desired product T-2 (136.4 mg, 94 %) as yellow solid.

Reference： [1]Fan, Tian-Yuan; Wu, Wen-Yu; Yu, Shao-Peng; Zhong, Yue; Zhao, Chao; Chen, Min; Li, He-Min; Li, Nian-Guang; Chen, Zhi; Chen, Sai; Sun, Zhi-Hui; Duan, Jin-Ao; Shi, Zhi-Hao [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 24]

15
[ 3989-13-7 ]
[ 139911-29-8 ]
((4’-fluoro-2’-methyl-[1,1’-biphenyl]-3-yl)ethynyl)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In tetrahydrofuran; water; at 80 - 90℃; for 24h;Inert atmosphere;	Step I: (4-fluoro-2-methylphenyl)boronic acid (1 eq.), ((3- bromophenyl)ethynyl) trimethylsilane (1.2 eq.), Pd(dppf)Cl2 (0.05 eq.) and Cs2CO3 (2.5 eq.) were added to a flask containing 8 ml of a degassed solution of tetrahydrofuran/water (4:1, v/v). The flask was fit with a condenser and transferred to a pre-heated oil bath maintained at 80-90 C. The reaction was allowed to reflux for 24 h and monitored by TLC. After 24 h, the reaction was quenched by adding 30 ml of water and extracted three times with 60 ml of dichloromethane. The combined organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified over silica gel with 100 % hexanes to give a clear oil in 86 % yield.

Reference： [1]Patent: WO2021/243015,2021,A1 .Location in patent: Page/Page column 48-49

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
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

[ CAS No. 139911-29-8 ] {[proInfo.proName]}

Quality Control of [ 139911-29-8 ]

Related Doc. of [ 139911-29-8 ]

Product Details of [ 139911-29-8 ]

Calculated chemistry of [ 139911-29-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 139911-29-8 ]

Application In Synthesis of [ 139911-29-8 ]

[ 139911-29-8 ] Synthesis Path-Upstream 1~5

[ 139911-29-8 ] Synthesis Path-Downstream 1~15

Related Functional Groups of [ 139911-29-8 ]

Fluorinated Building Blocks

Organoboron

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 139911-29-8 ]