[ CAS No. 208399-66-0 ] {[proInfo.proName]}

Name: 208399-66-0|(4-Methoxy-2-methylphenyl)boronic acid|97%
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SKU: A180606
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Quality Control of [ 208399-66-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 208399-66-0 ]

Product Details of [ 208399-66-0 ]

CAS No. :	208399-66-0	MDL No. :	MFCD02684315
Formula :	C₈H₁₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AMSQNQJCBXQYEX-UHFFFAOYSA-N
M.W :	165.98	Pubchem ID :	2773486
Synonyms :

Calculated chemistry of [ 208399-66-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.73
TPSA :	49.69 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) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	-0.32
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	-0.3
Consensus Log Po/w :	0.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.41 mg/ml ; 0.0145 mol/l
Class :	Very soluble
Log S (Ali) :	-1.8
Solubility :	2.64 mg/ml ; 0.0159 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	2.66 mg/ml ; 0.016 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 208399-66-0 ]

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 [ 208399-66-0 ]

* 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 [ 208399-66-0 ]
Downstream synthetic route of [ 208399-66-0 ]

[ 208399-66-0 ] Synthesis Path-Upstream 1~5

1
[ 208399-66-0 ]
[ 102-50-1 ]

Reference： [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2545 - 2553

2
[ 27060-75-9 ]
[ 208399-66-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2553 - 2570
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 12, p. 3953 - 3979
[3] European Journal of Organic Chemistry, 1998, # 5, p. 877 - 888
[4] Organic and Biomolecular Chemistry, 2004, vol. 2, # 23, p. 3504 - 3509
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 5, p. 787 - 797
[6] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2324 - 2341

3
[ 5419-55-6 ]
[ 27060-75-9 ]
[ 208399-66-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	With n-butyllithium In hexane	4-Methoxy-2-methylphenylboronic Acid The title compound was prepared by reacting 4-bromo-3-methylanisole (10 g, 0.050 mol) with n-butyl lithium (24 mL of 2.5 M solution in hexane, 0.055 mol) followed by triisopropyl borate (57.7 mL, 47.02 g, 0.25 mol) according to method F to yield 5.7 g (69percent) of a white solid: MS (ESI) m/z 313 (2M-H₂O-H)^-.

Reference： [1] Organic Letters, 2001, vol. 3, # 26, p. 4263 - 4265
[2] Patent: US2003/181519, 2003, A1,

4
[ 5419-55-6 ]
[ 55171-60-3 ]
[ 208399-66-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 5, p. 787 - 797

5
[ 121-43-7 ]
[ 55171-60-3 ]
[ 208399-66-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 5, p. 787 - 797

[ 208399-66-0 ] Synthesis Path-Downstream 1~31

1
[ 55171-60-3 ]
[ 208399-66-0 ]
[ 217468-53-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With water; sodium carbonate In 1,2-dimethoxyethane for 18h; Heating;
71%	With sodium carbonate In 1,2-dimethoxyethane; ethanol rt, 15 min; reflux, 48 h;

Reference： [1]De Koning, Charles B.; Michael, Joseph P.; Rousseau, Amanda L. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 5, p. 787 - 797]
[2]De Koning, Charles B.; Michael, Joseph P.; Rousseau, Amanda L. [Tetrahedron Letters, 1998, vol. 39, # 47, p. 8725 - 8728]

2
[ 25297-51-2 ]
[ 208399-66-0 ]
[ 392657-97-5 ]

Yield	Reaction Conditions	Operation in experiment
49%	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran Heating;

Reference： [1]Mello, Jesse V.; Finney, Nathaniel S. [Organic Letters, 2001, vol. 3, # 26, p. 4263 - 4265]

3
[ 25297-51-2 ]
[ 208399-66-0 ]
[ 392657-90-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tri-tert-butyl phosphine; caesium carbonate In tetrahydrofuran for 16h; Heating;
82%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tri-tert-butyl phosphine; caesium carbonate In tetrahydrofuran Heating;

Reference： [1]Fang, Albert G.; Mello, Jesse V.; Finney, Nathaniel S. [Organic Letters, 2003, vol. 5, # 7, p. 967 - 970]
[2]Mello, Jesse V.; Finney, Nathaniel S. [Organic Letters, 2001, vol. 3, # 26, p. 4263 - 4265]

4
[ 42521-09-5 ]
[ 208399-66-0 ]
[ 521958-81-6 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 967 - 970

5
[ 75884-70-7 ]
[ 208399-66-0 ]
[ 897661-91-5 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3753 - 3756

6
[ 186593-42-0 ]
[ 208399-66-0 ]
3-(4-methoxyphenyl)-2-methyl-5-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;PdCl2(PPh2(CH2)4PPh2); In N,N-dimethyl-formamide; toluene; at 150℃; for 0.166667h;Microwave irradiation;	Route B: Via cross-coupling of L2-Q to the protected core template.[00434] 3-(4-Methoxyphenyl)2-methyl-5-nitropyridine.; A mixture of 2-methyl-3- bromo-5-nitropyridine (115.3 mg, 0.5 mmol), 2-methyl-4-methoxyphenyl-boronic acid (91.2 mg, 0.5 mmol), Pd(dppb)Cl2 (16.3 mg, 0.03 mmol) and K2CO3 (359 mg, 2.6 mmol) in toluene/DMF (4 ml, 9:1) was heated at 1500C for 10 min under microwave irradiation. The mixture was filtered (celite), the solids were washed with DCM and the filtrate was concentrated. The residue was chromatographed on silica gel using Hex/EtOAc (gradient: 0 to 80% EtOAc) as eluents to afford the target compound. 1H-NMR (500 MHz, CD3OD) delta (ppm) 9.27 (d, J= 2.59 Hz, IH), 8.28 (d, J= 2.62 Hz, IH), 7.09 (d5 J= 8.37 Hz, IH), 6.94 (d, J= 2.56 Hz, IH), 6.89 (dd, J= 2.64 and 8.00 Hz, IH), 3.85 (s, 3H), 2.41 (s, 3H), 2.07 (s, 3H).

Reference： [1]Patent: WO2008/21388,2008,A1 .Location in patent: Page/Page column 186

7
[ 446273-59-2 ]
[ 208399-66-0 ]
[ 446273-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 12h;	4-Bromo-6-chloro-3-pyridazineamine (12 g) and 4-methoxy-2-methylphenylboronic acid (10.5 g) were dissolved in a mixed solvent of toluene (240 mL) and ethanol (45 mL), then tetrakistriphenylphosphine palladium complex (6.7 g) and a 2M aqueous sodium carbonate solution (24 mL) were added thereto, and the mixture was heated under stirring at 100C for 12 hours. After completion of the reaction, the solvent was evaporated. The residue was extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:4) to give the title compound (7.89 g) as brown crystals. 1H NMR (400MHz, CDCl3) delta 2.18 (s, 3H), 3.85 (s, 3H), 5.43 (br s, 2H), 6.82-6.90 (m, 2H), 7.08 (d, J = 8.2 Hz, 1H), 7.14 (s, 1H).

Reference： [1]Patent: EP1364952,2003,A1 .Location in patent: Page/Page column 39

8
[ 54796-47-3 ]
[ 208399-66-0 ]
[ 946426-96-6 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 80℃;	Step 1To amixture of 4-methoxy-2-methylphenylboronic acid (912 mg, 6 mmol), 5-bromo-4-methyl- thiophene-2-carboxylic acid methyl ester (1.1 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in toluene (30 mL) and water (5 mL) is bubbled N2 for 15 minutes followed by addition of tetrakis(triphenylphosphine) palladium (289 mg, 0.25 mmol). The mixture is stirred at 80 0C under Na overnight and filtered through a pad of diatomaceous earth eluting with EtOAc. The combined filtrate is concentrated. The resulting residue is purified by column chromatography (0-15% EtOAc in hexanes) to give 5-(4-methoxy-2-methyl- phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester (540 mg, 39%). 1H-NMR (CDCl3): δ 7.63 (s, <n="14"/>IH), 7.15 (d, IH, J = 8.4 Hz), 6.82 (d, IH, J = 2.8 Hz), 6.78(dd, IH, J = 2.8, J = 8.4 Hz), 4.79 (bs, IH), 3.88 (s, 3H), 3.83 (s, 3H), 2.17 (s, 3H), 2.02 (s, 3H).
39%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 80℃;	Step A; To a mixture of 4-methoxy-2-methylphenylboronic acid (912 mg, 6 mmol), 5- bromo-4-methyl-thiophene-2-carboxylic acid methyl ester (1.1 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in toluene (30 mL) and water (5 mL) is bubbled N2 for 15 minutes followed by addition of tetrakis(triphenylphosphine) palladium (289 mg, 0.25 mmol). The reaction mixture is stirred at 80 0C under N2 overnight. The reaction mixture is filtered through a diatomaceous earth pad eluting with EtOAc. The combined filtrate is <n="31"/>concentrated and the residue is purified by column chromatography on silica gel eluting with 0 - 15 % EtOAc in hexanes to give 5-(4-methoxy-2-methyl-phenyl)-4-methyl- thiophene-2-carboxylic acid methyl ester (540 mg, 39%). 1U NMR (CDCl3): δ 7.63 (s, IH), 7.15 (d, IH, J = 8.4 Hz), 6.82 (d, IH, J = 2.8 Hz), 6.78(dd, IH, J = 2.8, J = 8.4 Hz), 4.79 (bs, IH), 3.88 (s, 3H), 3.83 (s, 3H), 2.17 (s, 3H), 2.02 (s, 3H).
39%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 80℃;	Step ATo a mixture of 4-methoxy-2-methylphenylboronic acid (912 mg, 6 mmol), 5- bromo-4-methyl-thiophene-2-carboxylic acid methyl ester (1.1 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in toluene (30 mL) and water (5 mL) is bubbled N2 for 15 minutes followed by addition of tetrakis(triphenylphosphine) palladium (289 mg, 0.25 mmol). The mixture is stirred at 80 0C under N2 overnight. The reaction mixture is filtered through a Celite pad eluting with EtOAc. The combined filtrate is concentrated under reduced pressure and the residue is purified by column chromatography (0-15% EtOAc in hexanes) to give 5-(4-methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester (540 mg, 39%). 1H NMR (CDCl3): δ 7.63 (s, IH), 7.15 (d, IH, J = 8.4 Hz),6.82 (d, IH, J = 2.8 Hz), 6.78(dd, IH, J = 2.8, J = 8.4 Hz), 4.79 (bs, IH), 3.88 (s, 3H),3.83 (s, 3H), 2.17 (s, 3H), 2.02 (s, 3H).

Reference： [1]Patent: WO2007/92751,2007,A2 .Location in patent: Page/Page column 12-13
[2]Patent: WO2007/140174,2007,A2 .Location in patent: Page/Page column 29-30
[3]Patent: WO2007/140183,2007,A1 .Location in patent: Page/Page column 43

9
[ 100367-39-3 ]
[ 208399-66-0 ]
[ 1234690-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In dimethyl sulfoxide; at 90℃; for 2h;Inert atmosphere;	A suspension of <strong>[100367-39-3]4-bromo-2-methoxypyridine</strong> (341 mg, 1.82 mmol), 4-methyloxy- 2-methylphenyl boronic acid (452 mg, 2.72 mmol), Pd(PPh3)2Cl2 (133 mg, 0.182 mmol) and K2CO3 (503 mg, 3.64 mmol) in DMSO (10 mL) was degassed under reduced pressure for 1 h. The suspension was put under Ar and stirred at 90 0C for 2 h. The suspension was cooled, H2O was added, and the suspension was filtered to afford a light colored solid. Flash chromatography (silica gel, hexanes/(l :l EtOAc/hexanes), 100:0 to 0:100) afforded 235 mg of a white powder.

Reference： [1]Patent: WO2009/89482,2009,A1 .Location in patent: Page/Page column 212

10
[ 701910-14-7 ]
[ 208399-66-0 ]
7-(4-methoxy-2-methyl-phenyl)-2-methyl-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		7-Bromo-2-methyl-2H-indazole (4; 1.76 g, 8.3 mMol) and tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.25 mMol) were stirred in 15 mL of DME under argon atmosphere for 30 min. 4-Methoxy-2-methylbenzeneboronic acid (1.52 g, 9.2 mMol) was added, immediately followed by a solution of sodium carbonate (3.1 g, 29.1 mMol) in 10 mL water. The mixture was heated at a gentle reflux for 4 hr, and then cooled to rt and diluted with EtOAc (150 mL). The organic phase was washed with brine and dried over magnesium sulfate. Evaporation of the solvent afforded an oil, which was flash chromatographed on SiO2 and eluted with hexane:EtOAc (9:1) to afford 4c (1.9 g; 91%).

Reference： [1]Patent: US2004/110815,2004,A1 .Location in patent: Page/Page column 20

11
[ 17135-74-9 ]
[ 208399-66-0 ]
1,8-bis(2'-methyl-4'-methoxyphenyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In toluene; at 110℃; for 18h;Inert atmosphere;	A solution of <strong>[17135-74-9]1,8-dibromonaphthalene</strong>, (1.29 g, 4.5 mmol), 2-methyl-4-methoxyphenylboronic acid, 3, (2.24 g, 13.5 mmol), Pd(PPh3)4 (0.78 g, 0.68 mmol), and K3PO4, (4.30 g, 20.0 mmol) in 50 mL toluene was stirred at 110 C for 18 h. The resulting mixture was allowed to come to room temperature, quenched with water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (CH2Cl2/hexanes 2:3) afforded 1.66 g (4.5 mmol, >99%) of off-white crystals containing syn- and anti-isomers of 4 in a ratio of approximately 1:3.1H NMR: δ=1.76 (s, 4.6H), 1.83 (s, 1.4H), 3.69 (s, 4.4H), 3.71 (s, 1.4H), 6.28-6.39 (m, 4H), 6.66 (d, J=8.2 Hz, 0.5H), 6.87 (d, J=8.2 Hz, 1.5H), 7.16 (d, J=6.8 Hz, 2H), 7.46 (dd, J=6.8, 8.0 Hz, 2H), 7.89 (d, J=8.0 Hz, 2H). 13C NMR: δ=20.9, 21.0, 55.1, 55.2, 109.9, 110.3, 114.3, 114.4, 124.8, 125.0, 128.5, 129.0, 130.2, 130.4, 131.0, 131.6, 132.3, 134.8, 134.9, 135.2, 135.4, 136.5, 136.9, 139.5, 157.6, 158.1. Anal. Calcd for C26H24O2: C, 84.75; H, 6.57. Found: C, 84.74; H, 6.61.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6799 - 6803
[2]Chemical Communications,2009,p. 4827 - 4828
[3]European Journal of Organic Chemistry,2010,p. 5800 - 5806
[4]Organic Letters,2011,vol. 13,p. 4450 - 4453

12
[ 37159-60-7 ]
[ 208399-66-0 ]
[ 1198321-29-7 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5666 - 5669

13
[ 32460-02-9 ]
[ 208399-66-0 ]
[ 1430419-66-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3346 - 3366

14
[ 13191-36-1 ]
[ 208399-66-0 ]
[ 1430419-42-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3346 - 3366

15
[ 13191-36-1 ]
[ 208399-66-0 ]
[ 1430419-46-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3346 - 3366

16
[ 32460-00-7 ]
[ 208399-66-0 ]
[ 1430419-59-2 ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene at 120℃; for 12h; Inert atmosphere;

Reference： [1]Min, Jian; Wang, Pengcheng; Srinivasan, Sathish; Nwachukwu, Jerome C.; Guo, Pu; Huang, Minjian; Carlson, Kathryn E.; Katzenellenbogen, John A.; Nettles, Kendall W.; Zhou, Hai-Bing [Journal of Medicinal Chemistry, 2013, vol. 56, # 8, p. 3346 - 3366]

17
[ 89581-38-4 ]
[ 208399-66-0 ]
C₁₄H₁₄N₂O₃ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 491 - 495

18
[ 1025468-06-7 ]
[ 208399-66-0 ]
C₁₃H₁₃NO₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 491 - 495

19
[ 74290-68-9 ]
[ 208399-66-0 ]
6-(4-methoxy-2-methylphenyl)-5-methylpyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 130℃; for 2h;Inert atmosphere; Microwave irradiation;	(4-Methoxy-2-methylphenyl)boronic acid (104 mg, 0.63 mmol), was combined with <strong>[74290-68-9]6-bromo-5-methylpyrazin-2-amine</strong> (98 mg, 0.52 mmol) andtetrakis(triphenylphosphine)palladium(0) (31.6 mg, 0.03 mmol) in 1,4-dioxane (2 mL) and the reaction mixture was degassed with nitrogen. To this solution was added a degassed solution of sodium carbonate (166 mg, 1.56 mmol) in water (0.6 mL). After being heated in a microwave reactor at 130 00 for 2 hours, the reaction mixture was concentrated in vacuo. Purification via silica gel chromatography (Gradient: 40% to100% ethyl acetate in heptane) provided the product as a white solid. Yield: 111 mg,0.48 mmol, 93%. LCMS m/z 230.1 [M+H]. 1H NMR (400 MHz, CD3OD) oe 7.85 (5, 1H),7.08 (d, J=8.4 Hz, 1H), 6.87 (d, J=2.5 Hz, 1H), 6.84 (dd, J=8.0, 2.3 Hz, 1H), 3.82 (5,3H), 2.13 (5, 3H), 2.09 (5, 3H).

Reference： [1]Patent: WO2015/166370,2015,A1 .Location in patent: Page/Page column 107; 108

20
[ 36848-40-5 ]
[ 208399-66-0 ]
C₂₈H₂₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 6h; Inert atmosphere;	12 The example compound F-2 can be synthesized, for example, by the following procedure. First, a compound XX-9 is synthesized. In a 50-ml reaction chamber, 507 mg (1.50 mmol) of a compound XX-1 and 747 mg (4.5 mmol) of 4-metoxy-2-methylphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (7 ml/7 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Fd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 6 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduce pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-9 was obtained (478 mg, yield: 76%).

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1 Location in patent: Paragraph 0268-0270

21
[ 36848-40-5 ]
[ 208399-66-0 ]
C₃₄H₃₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile; water / 9 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1

22
[ 261953-36-0 ]
[ 208399-66-0 ]
6-(2-methyl-4-methoxyphenyl)-1H-indazole [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 1264 - 1268

23
[ 261953-36-0 ]
[ 208399-66-0 ]
6-(2-methyl-4-hydroxyphenyl)-1H-indazole [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 1264 - 1268

24
[ 208399-66-0 ]
[ 5307-05-1 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 361 - 364

25
[ 213744-81-1 ]
[ 208399-66-0 ]
4-chloro-7-isopropyl-5-(4-methoxy-2-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2037 - 2041

26
[ 54796-47-3 ]
[ 208399-66-0 ]
5-(4-hydroxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Patent: WO2007/140174,2007,A2

27
[ 17135-74-9 ]
[ 208399-66-0 ]
9-methoxy-7-methylfluoranthene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With tris-(dibenzylideneacetone)dipalladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine; In N,N-dimethyl-formamide; at 140℃; for 20h;Inert atmosphere;	<strong>[17135-74-9]1,8-dibromonaphthalene</strong> (50 g, 175 mmol) and (4-methoxy-2-methylphenyl)boronic acid (29.0 g, 175 mmol) was added to a mixture of DMF (1000 ml) and DBU (78 ml, 525 mmol), and the mixture is degassed with bubbling nitrogen for 30 min. Tricyclohexylphosphane (17.31 g, 52.5 mmol) was added and degassing continued for 10 min. Pd2(dba)3 (20.01 g, 21.86 mmol) was added and the reaction mixture heated to an internal temperature of 140 C. which was maintained for 20 h. The reaction mixture was then allowed to cool to room temperature. The reaction mixture was decanted and the vessel washed with methylene chloride (DCM) (2500 ml). The DMF was removed under reduced pressure to give a dark residue. The DCM washes were added to the residue and washed with brine (3400 mL). The DCM layer was concentrated under reduced pressure onto silica (120 g). The crude product was purified by column chromatography (DCM in heptane, 2CV heptane, 10CV 0-20% DCM, 10CV 20-25% DCM) to yield the product as a yellow solid (33.7 g), yield of 54%

Reference： [1]Patent: US2019/214583,2019,A1 .Location in patent: Paragraph 0167; 0168-0169

28
[ 41963-20-6 ]
[ 208399-66-0 ]
C₁₆H₁₅NO [ 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

29
[ 67832-11-5 ]
[ 208399-66-0 ]
C₁₆H₁₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-2-methylbenzonitrile; 4-methoxy-2-methylphenyl boronic acid With potassium carbonate In water at 20℃; for 0.25h; Stage #2: With palladium dichloride In water	4.3. General procedure for the preparation of compounds 3a-r 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]Sang, Yali; Han; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen [European Journal of Medicinal Chemistry, 2019, vol. 182]

30
[ 703-61-7 ]
[ 208399-66-0 ]
4-chloro-2-(4-methoxy-2-methylphenyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 90℃; for 6h;	10 Step 1: General procedure: To a stirring solution of 2,4-dichloroquinoline (6.16 g, 31.10 mmol) in toluene/ethanol (1:1 10 mL) was added 4-methoxyphenylboronic acid (5.2 g, 34.21 mmol), followed by sodium carbonate (1 M, 62 mL, 62.20 mmol). The reaction mixture was degassed over a slow flow of nitrogen for 15 minutes, then tetrakis(triphenylphosphine)- palladium(O) was added, the reaction flask flushed with nitrogen and placed in a heating bath to 90 °C for 6 hours. The cooled reaction mixture was diluted with ethyl acetate (50 mL), washed with water (25 mL), the aqueous washed with brine (20 mL), dried over sodium sulfate and filtered. The product was purified on silica gel (220 gm, 60-120 mesh) and concentrated under reduced pressure to give 4-chloro-2-(4-methoxyphenyl)quinoline as a white solid (5.0 g, 59%).1H NMR (CDCl3) d: 9.06 (d, J=8.2 Hz, 1H), 8.96-9.02 (m, 3H), 8.78-8.79 (m, 1H), 8.59-8.64 (m, 1H), 8.42-8.47 (m, 1H), 8.11-8.12 (m, 1H), 7.90 (d, J=7.6 Hz, 2H), 4.75 (s, 3H). MS m/z (M+) 270.03.

Reference： [1]Current Patent Assignee: BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD - WO2021/35101, 2021, A1 Location in patent: Paragraph 0380

31
[ 716-53-0 ]
[ 208399-66-0 ]
9-(4-methoxy-2-methylphenyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 3-(dicyclohexylphosphanyl)-N,N-diisopropyl-1-methyl-1H-indole-2-carboxamide In 1,4-dioxane at 110℃; for 1h; Schlenk technique; Inert atmosphere;

Reference： [1]Chen, Zicong; Ng, Shan Shan; So, Chau Ming; Yuen, On Ying [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1373 - 1378]

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Response
Code	Phrase
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P321
P322
P330	Rinse mouth.
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P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
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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.
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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:
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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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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:
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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. 208399-66-0 ] {[proInfo.proName]}

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[ 208399-66-0 ] Synthesis Path-Upstream 1~5

[ 208399-66-0 ] Synthesis Path-Downstream 1~31

Related Functional Groups of [ 208399-66-0 ]

Organoboron

Aryls

Ethers

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[ 208399-66-0 ]