[ CAS No. 127972-00-3 ] {[proInfo.proName]}

Name: 127972-00-3|2-Methoxy-5-methylphenylboronic acid|97%
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SKU: A131966
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Quality Control of [ 127972-00-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 127972-00-3 ]

SDS Specification

Alternatived Products of [ 127972-00-3 ]

Product Details of [ 127972-00-3 ]

CAS No. :	127972-00-3	MDL No. :	MFCD02179465
Formula :	C₈H₁₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CSVKZOZMPSRLTC-UHFFFAOYSA-N
M.W :	165.98	Pubchem ID :	2773485
Synonyms :

Calculated chemistry of [ 127972-00-3 ]

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 :	1.67

Safety of [ 127972-00-3 ]

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

Application In Synthesis of [ 127972-00-3 ]

* 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 [ 127972-00-3 ]
Downstream synthetic route of [ 127972-00-3 ]

[ 127972-00-3 ] Synthesis Path-Upstream 1~4

1
[ 121-43-7 ]
[ 22002-45-5 ]
[ 127972-00-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Stage #2: at -78 - 20℃; for 4 h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	To the THF solution of 2-bromo-1-methoxy-4-methybenzene(1.39 g, 15 mmol) at -780° C. under nitrogen was added n-butyllithium (15 mmol) dropwise. After stiring at -78° C. for one hour, the solution was added to trimethylborate (15 mmol) in THF (100 mL). The reaction mixture was warmed to room temperature and continuously stirred for four hours before poured into 3N hydrochloride (125 mL), then extracted with ethyl acetate three time. The organics were combined, dried over magnesium and concentrated to give yellow-white solid(2.2 g, 89percent). 1H NMR (300 MHz, d6-DMSO) δ 7.6 (s, 1H), 7.38 (d, J=2.3 Hz, 1H), 7.19 (dd, J=8.4 Hz, 2.3 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 3.78 (s, 3H), 2.2 (s, 3H).
96%	With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid	2-Methoxy-5-methylphenylboronic Acid (Structure 37 of Scheme XI, where R¹ =H, R² =methyl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.
96%	With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid	EXAMPLE 216 1,2-Dihydro-2,2,4,9-tetramethyl-5-coumarino[3,4-f]quinoline (Compound 316, structure 41 of Scheme XI, where R¹ =H, R² =methyl) 2-Methoxy-5-methylphenylboronic acid (structure 37 of Scheme XI, where R¹ =H, R² =methyl). This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.

96%

With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid

EXAMPLE 216
1,2-Dihydro-2,2,4,9-tetramethyl-5-coumarino[3,4-f]quinoline (Compound 316, structure 41 of Scheme XI, where R¹ =H, R² =methyl)
2-Methoxy-5-methylphenylboronic acid (structure 37 of Scheme XI, where R¹ =H, R² =methyl)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.

Reference： [1] Patent: US2004/19190, 2004, A1, . Location in patent: Page 24
[2] Patent: US5688808, 1997, A,
[3] Patent: US5693646, 1997, A,
[4] Patent: US5688810, 1997, A,
[5] Patent: US5693647, 1997, A,
[6] Patent: US5696127, 1997, A,
[7] ACS Catalysis, 2017, vol. 7, # 4, p. 2607 - 2615

2
[ 104-93-8 ]
[ 121-43-7 ]
[ 127972-00-3 ]

Reference： [1] Dalton Transactions, 2013, vol. 42, # 45, p. 15974 - 15986

3
[ 22002-45-5 ]
[ 127972-00-3 ]

Reference： [1] Macromolecules, 2004, vol. 37, # 22, p. 8201 - 8203
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6626 - 6637

4
[ 127972-00-3 ]
[ 259209-21-7 ]

Reference： [1] Journal of Combinatorial Chemistry, 2010, vol. 12, # 5, p. 664 - 669
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 37, p. 9755 - 9758

[ 127972-00-3 ] Synthesis Path-Downstream 1~87

1
[ 127972-00-3 ]
[ 127971-98-6 ]
[ 127972-04-7 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

2
[ 127972-00-3 ]
[ 75640-69-6 ]
2,2'-Dimethoxy-3,3'-bis-(2-methoxy-5-methyl-phenyl)-[1,1']binaphthalenyl [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

3
C₁₀H₁₅BO₃ [ No CAS ]
[ 127972-00-3 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 8201 - 8203

4
[ 98591-57-2 ]
[ 127972-00-3 ]
7-chloro-4-(2-methoxy-5-methylphenyl)quinoline [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2004,vol. 82,p. 206 - 214

5
[ 1564-64-3 ]
[ 127972-00-3 ]
[ 796975-81-0 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 8201 - 8203

6
[ 852111-55-8 ]
[ 127972-00-3 ]
(+/-)-[5-fluoro-7-(2-methoxy-5-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 225 (+-)-[5-fluoro-7-(2-methoxy-5-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine The title compound was prepared (0.017 g, 5percent) following the general procedure of Example 154 as a white solid, hydrochloride salt from (+-)-(7-bromo-5-fluoro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.40 g, 1.0 mmol) <strong>[127972-00-3](2-methoxy-5-methylphenyl)boronic acid</strong> (0.51 g, 3.0 mmol). mp 110-111° C.

Reference： [1]Patent: US2005/261347,2005,A1

7
[ 861942-71-4 ]
[ 127972-00-3 ]
(1R)-(2-methoxy-5-methylphenyl)[(S)-2-(p-tolylsulfinyl)phenyl]methanol [ No CAS ]
(1S)-(2-methoxy-5-methylphenyl)[(S)-2-(p-tolylsulfinyl)phenyl]methanol [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 1628 - 1634

8
[ 955134-09-5 ]
[ 127972-00-3 ]
[ 955134-11-9 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10445 - 10453

9
[ 955134-22-2 ]
[ 127972-00-3 ]
[ 955134-24-4 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10445 - 10453

10
[ 127972-00-3 ]
methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-L-histidinate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10445 - 10453
[2]Tetrahedron,2007,vol. 63,p. 10445 - 10453

11
[ 22002-45-5 ]
[ 127972-00-3 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 8201 - 8203
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 6626 - 6637

12
[ 127972-00-3 ]
[ 792934-42-0 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 8201 - 8203

13
[ 127972-00-3 ]
C₄₈H₄₄N₂O₂ [ No CAS ]

Reference： [1]Macromolecules,2004,vol. 37,p. 8201 - 8203

14
[ 127972-00-3 ]
[ 179898-48-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 135 - 138

15
[ 127972-00-3 ]
[ 179898-49-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 135 - 138
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 135 - 138

16
[ 127972-00-3 ]
[ 827623-17-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 135 - 138

17
[ 127972-00-3 ]
[ 71128-89-7 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2002,vol. 390,p. 5 - 10

18
[ 127972-00-3 ]
(R)-3,3'-bis(2'-methoxy-5'-methylphenyl)-1,1'-bi-2-naphthol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 7940 - 7956

19
[ 127972-00-3 ]
3,3'-Bis-(2-hydroxy-5-methyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

20
[ 127972-00-3 ]
[ 148950-84-9 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

21
[ 127972-00-3 ]
3,3'-Bis-(2-hydroxy-5-methyl-3-tri-tert-butylsilanyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

22
[ 127972-00-3 ]
3,3'-Bis-(3-bromo-5-methyl-2-tri-tert-butylsilanyloxy-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

23
[ 127972-00-3 ]
3,3'-Bis-[3-(tert-butyl-diphenyl-silanyl)-2-hydroxy-5-methyl-phenyl]-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

24
[ 127972-00-3 ]
[ 148951-16-0 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

25
[ 127972-00-3 ]
3,3'-Bis-(2-hydroxy-5-methyl-3-triphenylsilanyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

26
[ 127972-00-3 ]
[ 148950-85-0 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

27
[ 127972-00-3 ]
3,3'-Bis-(2-hydroxy-5-methyl-3-tri-o-tolylsilanyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

28
[ 127972-00-3 ]
[ 148950-90-7 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2938 - 2939

29
[ 127972-00-3 ]
[ 127972-14-9 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585
[3]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

30
[ 127972-00-3 ]
[ 127972-05-8 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

31
[ 127972-00-3 ]
[ 127972-07-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

32
[ 127972-00-3 ]
[ 127972-10-5 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

33
[ 127972-00-3 ]
[ 127972-06-9 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

34
[ 127972-00-3 ]
[ 127972-09-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

35
[ 127972-00-3 ]
[ 127972-08-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4581 - 4585

37
[ 6952-59-6 ]
[ 127972-00-3 ]
[ 777944-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 48h;Heating / reflux;	A mixture of the product from step (i) (0.8g), 3-BROMOBENZONITRILE (0.877g), 2M aqueous sodium carbonate (3. 0ML) and TETRAKISTRIPHENYLPHOSPHINE palladium (0) (0.2g) in TOLUENE (12ML) and ethanol (3ml) was heated at reflux for 48h. The mixture was partitioned between EtOAc and water, the organics separated, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 10percent ETOAC/ISOHEXANE. Yield 0.92g LH NMR DMSO : No. 7.9 (1H, d); 7.8 (2H, m); 7.61 (1H, t) ; 7.16-7. 22 (2H, m); 7.04 (1H, d); 3.75 (3H, s); 2.29 (3H, s)

Reference： [1]Patent: WO2004/89884,2004,A1 .Location in patent: Page 29

38
[ 934842-20-3 ]
[ 127972-00-3 ]
methyl [3,5-bis(trifluoromethyl)benzyl][2'-methoxy-5'-methyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; In water; acetone; for 1h;Heating / reflux;	A mixture of methyl [3,5-bis(trifluoromethyl)benzyl][2-iodo-5-(trifluoromethyl)benzyl]carbamate (0.10 g, 0.17 mmol) from Example 5, and <strong>[127972-00-3]2-methoxy-5-methylphenyl boronic acid</strong> (0.034 g, 0.2 mmol), palladium acetate (0.0038 g, 0.017 mmol) and potassium carbonate (0.047 g, 0.34 mmol) in 4:1 acetone/water (10 ml) was heated and maintained at reflux for 1 h. The color of the solution turned dark. Acetone was removed and the residue was extracted with methylene chloride (3 x 10 ml). The combined organic layers were washed with water, then brine, and dried over sodium sulfate. The title compound was obtained as a colorless oil by preparative thin layer chromatography using acetone/hexane (5: 95) as the eluant. 'H NMR (CDC13, 500 MHz): 8 7.73 (s, 1H), 7.58 (d, J= 8.5 Hz, 1H), 7.47 (s, 2H), 7.35 (m, 1H), 7.32 (d, J = 8.0 Hz, 1H), 7.19 (m, 1H), 6.85 (m, 2H), 4.23-4.36 (m, 4H), 3.79 (m, 3H), 3.68 (s, 3H), 2.25 (s, 3H). LC-MS (M+1): 580.0 (4.61 min).

Reference： [1]Patent: WO2005/100298,2005,A1 .Location in patent: Page/Page column 47-48

39
[ 868167-54-8 ]
[ 127972-00-3 ]
methyl [3,5-bis(trifluoromethyl)benzyl][(4-fluoro-2'-methoxy-5'-methylbiphenyl-2-yl)methyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; In water; acetone; for 1h;Heating / reflux;	To a solution of 2-bromo-5-fluoro benzyl bromide (0.5 g, 1.86 mmol) and 3,5- bis (trifluoromethyl)benzylamine (0.45 g, 1.86 mmol) in methylene chloride (10 ml) at 0 °C, triethyl amine (0.39 ml, 2.80 mmol) was added. The solution was slowly warmed to room temperature and stirred for 18 h. The solvent was removed under reduced pressure. The title compound was obtained by flash column chromatography using EtOAc/hexane (2: 8) as the eluant. 1H NMR (CDCl3,500 MHz) No. 7.88 (s, 2H), 7.80 (s, 1H), 7.53 (dd, J = 8.8,5.3 Hz, 1H), 7.18 (dd, J = 9, 3.3 Hz, 1H), 6.91 (dt, J = 8.5,3.3 Hz, 1H), 3.98 (s, 2H), 3.90 (s, 2H). Step B: Methyl 13,5-bis(trifluoromethyl)benzyll(2-bromo-5-fluorobenzyl)carbamate To a solution of [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)amine from Step A (0.14 g) in methylene chloride at room temperature, excess methyl chloroformate (0.1 ml) and triethyl amine (0.1 ml) were added. The solution was stirred at room temperature for 2 h and the solvent was removed under reduced pressure. The title compound was obtained by flash column chromatography using EtOAc/hexane (1: 9) as the eluant.'H NMR (CDC13, 500 MHz) 8 7.80 (s, 1H), 7.68 (s, 1H), 7.60 (s, 1H), 7.48 (m, 1H), 6.88 (m, 2H), 4.60 (m, 4H), 3.81 (s, 3H). Step C: Methyl f 3,5-bis(trifluoromethyl)ben(at)ll f (4-fluoro-2'-methox(at)5'-methylbiphenyl- 2-yl)methyllcarbamate A mixture of the Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)carbamate from Step B (0.02g, 0.04 mmol), potassium carbonate (0.011 g, 0.08 mmol) , 2-methoxy-5-methyl phenyl boronic acid (0.008 g, 0.05 mmol) and catalytic amount of palladium acetate (1 mg) in 4:1 acetone/water (2.5 ml) was heated to and maintained at reflux for 1 h. TLC analysis (acetone/hexane = 5: 95) showed no starting material. The solvent was removed under reduced pressure and the residue was extracted with methylene chloride (3 x 10 ml). The combined organic layers were washed with brine and dried over sodium sulfate. The title compound was obtained by preparative thin layer chromatography using acetone:hexane (5: 95) as the eluant. 1H NMR (CDCl3,500 MHz) No. 7.75 (s, 1H), 7.50 (s, 1H), 7.38 (s, 1H), 7.20 (m, 2H), 7.04 (m, 2H), 6.84 (s, 1H), 6.80 (m, 1H), 4.18-4.60 (m, 4H), 3.80 (s, 3H), 3.68 (s, 3H), 2.32 (s, 3H). LC- MS (M+1) 530.4 (4.43 min).

Reference： [1]Patent: WO2005/100298,2005,A1 .Location in patent: Page/Page column 48-49

40
[ 127972-00-3 ]
[ 86544-77-6 ]
[ 859221-55-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 3h;	To a mixture of 2-methoxy-5-methylphenylboronic acid (1 g, 6.02 mmol), trifluoromethanesulfonic acid 3,3,5,5-tetramethylcyclohex-1-enyl ester (1.9 g, 6.62 mmol) produced in Example (4a) and 1,2-dimethoxyethane (30 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.30 mmol) and 2N aqueous solution of sodium carbonate (9.0 mL, 18.0 mmol), followed by stirring for 3 hours at an external temperature of 90° C. under a nitrogen atmosphere. Brine was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtrated, the resultant filtrate was concentrated under reduced pressure to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 1.0 g of the title compound as a light yellow oil. 1H-NMR (400 MHz, CDCl3) delta: 1.01 (s, 6H), 1.07 (s, 6H), 1.39 (s, 2H), 2.07 (d, J=1.6 Hz, 2H), 2.28 (s, 3H), 3.75 (s, 3H), 5.42 (s, 1H), 6.73 (d, J=8.4 Hz, 1H), 6.91 (d, J=2.0 Hz, 1H), 6.97 (dd, J=8.4, 2.0 Hz, 1H).

Reference： [1]Patent: US2005/261291,2005,A1 .Location in patent: Page/Page column 154

41
[ 888738-22-5 ]
[ 127972-00-3 ]
(3,5-bis-trifluoromethyl-benzyl)-[2-(2-methoxy-5-methyl-phenyl)-6-trifluoromethyl-pyridin-3-ylmethyl]-(2-methyl-2H-tetrazol-5-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; ethanol; at 95℃; for 16h;	To a solution of 2-methoxy-5-methylphenylboronic acid (0.15 mmol) in ethanol (0.5 ml.) was added the product of preparation 10 (0.1 mmol) in 1 ,4-dioxan (0.4 ml_) followed by Pd(PPh3)4 in ethanol (0.5 mL) and Na2CO3 (0.8 mmol). The resulting mixture was shaken at 95°C for 16 hours, diluted with ethyl acetate (2 mL) and washed with 10percent w/v Na2CO3. The mixture was purified by Shimadzu HPLC using nonpolar acidic method to yield the title compound (43.2 mg). 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 2.3 (s, 3 H) 3.7 (s, 3 H) 4.2 (s, 3 H) 4.38 (d, J=17.0 Hz, 1 H) 4.43 (d, J=17.0 Hz, 1 H) 4.6 (d, J=15.8 Hz, 1 H) 4.8 (d, J=16.8 Hz, 1 H) 6.8 (d, J=8.5 Hz, 1 H) 7.1 (d, J=2.1 Hz, 1 H) 7.2 (dd,-J=8.4, 2.2 Hz, 1 H) 7.5 (s, 2 H) 7.6 (d, J=7.9 Hz, 1 H) 7.7 (s, 1 H) 7.8 (d, J=7.9 Hz, 1 H); MS (ES+) CaIc: 604.16, Found: 605.2 (M+1).

Reference： [1]Patent: WO2006/56854,2006,A1 .Location in patent: Page/Page column 73

42
[ 121-43-7 ]
[ 22002-45-5 ]
[ 127972-00-3 ]

Yield	Reaction Conditions	Operation in experiment
89%		To the THF solution of 2-bromo-1-methoxy-4-methybenzene(1.39 g, 15 mmol) at -780° C. under nitrogen was added n-butyllithium (15 mmol) dropwise. After stiring at -78° C. for one hour, the solution was added to trimethylborate (15 mmol) in THF (100 mL). The reaction mixture was warmed to room temperature and continuously stirred for four hours before poured into 3N hydrochloride (125 mL), then extracted with ethyl acetate three time. The organics were combined, dried over magnesium and concentrated to give yellow-white solid(2.2 g, 89percent). 1H NMR (300 MHz, d6-DMSO) delta 7.6 (s, 1H), 7.38 (d, J=2.3 Hz, 1H), 7.19 (dd, J=8.4 Hz, 2.3 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 3.78 (s, 3H), 2.2 (s, 3H).
1.60 g (96%)	In (5-fluoro-2-methoxyphenyl)boronic acid;	EXAMPLE 216 1,2-Dihydro-2,2,4,9-tetramethyl-5-coumarino[3,4-f]quinoline (Compound 316, structure 41 of Scheme XI, where R1 =H, R2 =methyl) 2-Methoxy-5-methylphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methyl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLl (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.
1.60 g (96%)	With n-butyllithium; In (5-fluoro-2-methoxyphenyl)boronic acid;	2-Methoxy-5-methylphenylboronic Acid (Structure 37 of Scheme XI, where R1 =H, R2 =methyl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.

1.60 g (96%)	With n-butyllithium; In (5-fluoro-2-methoxyphenyl)boronic acid;	EXAMPLE 216 1,2-Dihydro-2,2,4,9-tetramethyl-5-coumarino[3,4-f]quinoline (Compound 316, structure 41 of Scheme XI, where R1 =H, R2 =methyl) 2-Methoxy-5-methylphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methyl). This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.
1.60 g (96%)	With n-butyllithium; In (5-fluoro-2-methoxyphenyl)boronic acid;	EXAMPLE 216 1,2-Dihydro-2,2,4,9-tetramethyl-5-coumarino[3,4-f]quinoline (Compound 316, structure 41 of Scheme XI, where R1 =H, R2 =methyl) 2-Methoxy-5-methylphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methyl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-methylanisole (2.00 g, 9.94 mmol), n-BuLi (2.5M in hexanes; 4.00 mL, 10 mmol), and trimethylborate (3.4 mL, 30 mmol) to afford 1.60 g (96percent) of 2-methoxy-5-methylphenylboronic acid which was used without further purification.

Reference： [1]Patent: US2004/19190,2004,A1 .Location in patent: Page 24
[2]Patent: US5688808,1997,A
[3]Patent: US5693646,1997,A
[4]Patent: US5688810,1997,A
[5]Patent: US5693647,1997,A
[6]ACS Catalysis,2017,vol. 7,p. 2607 - 2615

43
(PPh₃)4 Pd [ No CAS ]
[ 6942-36-5 ]
[ 127972-00-3 ]
[ 179898-46-5 ]

Yield	Reaction Conditions	Operation in experiment
2.03 g (98%)	In methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate;	Methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate This compound was prepared in a manner similar to that of methyl 5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (1.80 g, 6.92 mmol), (PPh3)4 Pd (0.33 g, 0.28 mmol), and 2-methoxy-5-methylphenylboronic acid (1.58 g, 9.51 mmol) to afford 2.03 g (98percent) of methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate as a white solid. Data for methyl (2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate): 1 H NMR (400 MHz, CDCl3) 8.69 (d, J=2.5, 1 H), 8.36 (dd, J=8.4, 2.5, 1H), 7.51 (d, J=8.5, 1H), 7.20 (m, 1H), 7.07 (d, J=2.1, 1H), 6.81 (d, J=8.4, 1H), 3.75 (s, 3H), 3.69 (s, 3H), 2.35 (s, 3H).
2.03 g (98%)	In methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate;	Methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate. This compound was prepared in a manner similar to that of methyl 5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (1.80 g, 6.92 mmol), (PPh3)4 Pd (0.33 g, 0.28 mmol), and 2-methoxy-5-methylphenylboronic acid (1.58 g, 9.51 mmol) to afford 2.03 g (98percent) of methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate as a white solid. Data for methyl (2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate): 1 H NMR (400 MHz, CDCl3) 8.69 (d, J=2.5, 1H), 8.36 (dd, J=8.4, 2.5, 1H), 7.51 (d, J=8.5, 1H), 7.20 (m, 1H), 7.07 (d, J=2.1, 1H), 6.81 (d, J=8.4, 1H), 3.75 (s, 3H), 3.69 (s, 3H), 2.35 (s, 3H).
2.03 g (98%)	In methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate;	Methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate This compound was prepared in a manner similar to that of methyl 5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (1.80 g, 6.92 mmol), (PPh3)4 Pd (0.33 g, 0.28 mmol), and 2-methoxy-5-methylphenylboronic acid (1.58 g, 9.51 mmol) to afford 2.03 g (98percent) of methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate as a white solid. Data for methyl (2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate): 1 H NMR (400 MHz, CDCl3) 8.69 (d, J=2.5, 1H), 8.36 (dd, J=8.4, 2.5, 1H), 7.51 (d, J=8.5, 1H), 7.20 (m, 1H), 7.07 (d, J=2.1, 1H), 6.81 (d, J=8.4, 1H), 3.75 (s, 3H), 3.69 (s, 3H), 2.35 (s, 3H).

Reference： [1]Patent: US5688808,1997,A
[2]Patent: US5688810,1997,A
[3]Patent: US5693646,1997,A

44
[ 205585-50-8 ]
[ 35661-60-0 ]
[ 127972-00-3 ]
[ 1086462-70-5 ]
[ 1086462-68-1 ]
[ 1086462-72-7 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 10538 - 10545

45
[ 34160-40-2 ]
[ 127972-00-3 ]
C₁₄H₁₃NO₂ [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 9857 - 9864

46
[ 107346-32-7 ]
[ 127972-00-3 ]
4-amino-8-(2-methoxy-5-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		EXAMPLE 49 4-amino-8-(2-methoxy-5-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (150 mg, 0.485 mmol) and 2-methoxy-5-methyl-phenylboronic acid (166 mg, 1.000 mmol) were reacted to afford the title compound (141mg, 83percent yield) as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.56 (br, 1H), 7.88-7.82 (m, 1H), 7.76-7.65 (m, 2H), 7.22-7.12 (m, 2H), 6.93 (m, 1H), 3.67 (s, 3H), 3.45 (apparent q, J=7.0 Hz, 2H), 2.34 (s, 3H), 1.65 (apparent sextet, J=7.0 Hz, 2H), 0.99 (t, J=7.0 Hz, 3H). MS APCI, m/z=351 (M+H). HPLC 1.96 min.
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 90℃;	General procedure: 4-Amino-7-X-8-(aryl)-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).The corresponding bromide-precursor(III) (1 equiv), the corresponding aryl boronic acid reagent (2.2 equiv), tetrakis(triphenylphosphine)palladium(0) (0.05 equiv) and potassium carbonate (3.0 equiv) in DME/ethanol/water (7/2/3) were heated at 90 °C, monitored by LC/MS. The reaction concentration was 0.3 M. Upon completion, the reaction mixture was cooled to room temperature, diluted with chloroform and washed with water. The chloroform layer was dried with magnesium sulfate, and evaporated to constant mass. The crude product was loaded onto a silica gel column, and eluted with 0-10percent methanol in methylene chloride to give a yellow or tan solid. The solid was further crystalized from ether/methylene chloride, or purified by HPLC to give a white, yellow or tan solid as the desired product in 50-85percent yield.

Reference： [1]Patent: US2008/318925,2008,A1
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2927 - 2938

47
4-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide [ No CAS ]
[ 127972-00-3 ]
4-amino-N-cyclopropyl-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		EXAMPLE 94 4-amino-N-cyclopropyl-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (143 mg, 0.47 mmol) and 2-methoxy-5-methylphenylboronic acid (155 mg, 0.94 mmol) were reacted. After purification the title compound (120 mg, 74percent yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) delta 9.00 (d, J=4.9 Hz, 1H), 8.38 (d, J=7.1 Hz, 1H), 7.74 (t, J=7.7 Hz, 1H), 7.68 (d, J=7.1 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 7.06 (s, 1H), 6.98 (d, J=8.5 Hz, 1H), 3.57 (s, 3H), 2.96 (m, 1H), 2.28 (s, 3H), 0.70(m, 4H). MS APCI, m/z=349.

Reference： [1]Patent: US2008/318925,2008,A1

48
[ 942438-80-4 ]
[ 127972-00-3 ]
4-amino-N-cyclopropyl-7-fluoro-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		EXAMPLE 167 4-amino-N-cyclopropyl-7-fluoro-8-(2-methoxy-5-methylphenyl)cinnoline-3-carboxamide Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (178 mg, 0.48 mmol) and 2-methoxy-5-methylphenylboronic acid (160 mg, 0.96 mmol) were reacted. After purification the title compound (134 mg, 76percent yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) delta 8.98 (d, J=4.8 Hz, 1H), 8.50 (a dd, J=5.5, 9.3 Hz, 1H), 7.71 (t, J=9.1 Hz, 1H), 7.23 (m,1H), 7.106(s, 1H), 7.02 (d, J=8.4 Hz, 1H), 3.60 (s, 3H), 2.95 (m, 1H), 2.28 (s, 3H), 0.67 (m, 4H). MS APCI, m/z=367.

Reference： [1]Patent: US2008/318925,2008,A1

49
[ 942438-93-9 ]
[ 127972-00-3 ]
4-amino-N-cyclobutyl-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 139 4-amino-N-cyclobutyl-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide Using Method A, 4-amino-8-bromo-N-cyclobutyl-cinnoline-3-carboxamide (145 mg) and 2-methoxy-5-methyl-phenyl boronic acid (186 mg) were reacted to afford the title compound (94 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) delta 9.20 (d, 1H), 8.38 (d, 1H), 7.76-7.66 (m, 2H), 7.20 (m, 1H), 7.07 (m, 1H), 7.00 (m, 1H), 4.50 (m, 1H), 3.58 (s, 3H), 2.29 (s, 3H), 2.26-2.10 (m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=363 (M+H).

Reference： [1]Patent: US2008/318925,2008,A1

50
[ 942438-94-0 ]
[ 127972-00-3 ]
4-amino-N-cyclobutyl-7-fluoro-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 124 4-amino-N-cyclobutyl-7-fluoro-8-(2-methoxy-5-methyl-phenyl)cinnoline-3-carboxamide Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 2-methoxy-5-methyl-phenyl boronic acid (187 mg) were reacted to afford the title compound (128 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) delta 9.18 (d, 1H), 8.50 (m, 1H), 7.71 (m, 1H), 7.24 (m, 1H), 7.07 (m, 1H), 7.03 (m, 1H), 4.49 (m, 1H), 3.61 (s, 3H), 2.29 (s, 3H), 2.26-2.10 (m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=381 (M+H).

Reference： [1]Patent: US2008/318925,2008,A1

51
[ 645-00-1 ]
[ 127972-00-3 ]
[ 1155877-66-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate;palladium diacetate; In methanol; water; at 20℃; for 20h;	2-Methoxy-5-methyl-3'-nitro-biphenyl INT-1 A reaction mixture of <strong>[127972-00-3]2-methoxy-5-methylphenyl boronic acid</strong> (5 g, 30.3 mmol), 3-nitro-iodobenzen (7.5 g, 30.3 mmol), K2CO3 (8.36 g, 60.6 mmol), Pd(OAc)2 (339 mg, 1.52 mmol) in methanol (150 ml) and water (30 ml) was stirred at room temperature for 20 hours. The reaction mixture was diluted with ethyl acetate (600 ml) washed with diluted NaHSO3 aq., water, brine and dried over Na2SO4. After removal of solvent, 6.7 g of crude product INT-1 was obtained. Yield: 91percent.

Reference： [1]Patent: US2009/136473,2009,A1 .Location in patent: Page/Page column 21

52
[ 1146160-27-1 ]
[ 127972-00-3 ]
[ 1146160-29-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; butan-1-ol; for 17h;Heating / reflux;	Synthesis 30-B; (S)-tert-Butyl 3-(2-(2-methoxy-5-methylphenyl)quinazolin-4-ylamino)pyrrolidine-1- carboxylate; <n="131"/>A mixture of toluene (1.8 ml_), n-butanol (3 ml.) and 2M Na2CO3 (3 ml.) was degassed with a stream of nitrogen for 20 minutes. The mixture was transferred onto a degassed mixture of (S)-tert-butyl 3-(2-chloroquinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.300 g, 0.86 mmol), palladium tetrakistriphenyl phosphine (0.0718 g, 0.06 mmol) and <strong>[127972-00-3]5-methyl-2-methoxyphenylboronic acid</strong> (0.143 g, 0.86 mmol) and the solution was heated at reflux. After 17 hours the reaction was cooled, diluted with water (20 mL), and extracted with ethyl acetate (2 x 20 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4), and concentrated. Silica chromatography (6:1-1:1 petroleum ether/ethyl acetate) gave the title compound as a colourless solid (0.329 g, 99percent).LC-MS (LCT2) m/z 435 [M+H+], R, 3.77 minutes. 1H NMR (CDCI3) delta 7.91 (d, J 8.0 Hz, 1H), 7.82 (s, 1H)1 7.69 (t, J 8.0 Hz, 1H). 7.54 (s, 1H), 7.39 (t, J 8.0 Hz, 1H), 7.17 (d, J 8.0, 1 H), 6.91 (d, J 8.0, 1 H), 6.16-6.07 (m, 1H), 4.92 (s, 1 H), 3.82 (s, 3H), 3.56 (br s, 1 H), 3.48 (br s, 2H), 3.35 (br s, 1 H), 2.33 (s, 3H), 2.27 (br s, 1 H), 2.08 (br s, 1 H), 1.47 (s, 9H).

Reference： [1]Patent: WO2009/53694,2009,A1 .Location in patent: Page/Page column 128-129
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 580 - 590

53
[ 935-02-4 ]
[ 127972-00-3 ]
[ 1152781-50-4 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 4232 - 4235

54
[ 1128268-00-7 ]
[ 127972-00-3 ]
[ 1128268-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 70℃; for 18h;	Step A. Ethyl 1-[6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate; To a flask containing the title compound from Example 1 Step A (1.50 g, 4.69 mmol) were added <strong>[127972-00-3]2-methoxy-5-methylphenyl boronic acid</strong> (0.779 g, 4.69 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (329 mg, 0.469 mmol). Acetonitrile (12 mL) and sodium carbonate (11.7 mL, 1.0 M aqueous, 11.7 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 18 h, then was allowed to cool to room temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 20percent EtOAc in hexanes, then 20 to 100percent EtOAc in hexanes) provided compound the title compound: LCMS m/z 406.4 [M+H]+; 1H NMR (500 MHz, CDCl3) delta 8.12 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.91 (t, J=8.0 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.19 (dd, J=8.0, 2.0 Hz, 1H), 6.91 (d, J=8.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 3.87 (s, 3H), 2.35 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 70℃; for 18h;Inert atmosphere;	Example 12; Step A. Ethyl 1-[6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylateTo a flask containing the title compound from Example 1 Step D (1.50 g, 4.69 mmol) were added <strong>[127972-00-3]2-methoxy-5-methylphenyl boronic acid</strong> (0.779 g, 4.69 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (329 mg, 0.469 mmol). Acetonitrile (12 mL) and sodium carbonate (11.7 mL, 1.0 M aqueous, 11.7 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 18 h, then was allowed to cool to room temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 20percent EtOAc in hexanes, then 20 to 100percent EtOAc in hexanes) provided the title compound: LCMS m/z 406.4 [M+H]+; 1H NMR (500 MHz, CDCl3) delta 8.12 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.91 (t, J=8.0 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.19 (dd, J=8.0, 2.0 Hz, 1H), 6.91 (d, J=8.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 3.87 (s, 3H), 2.35 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 15h;	Compound 1-4 (3.40 g, 10.6 mmol) is combined with boronic acid 1-5 (3.50 g, 21.1 mmol), tetrakis(triphenylphoshphine)palladium (Pd(PPh3)4) (615 mg, 0.532 mmol), and aqueous sodium carbonate (Na2C03) (2N, 21.0 mL, 42.0 mmol) in 1,2-DME. The mixture is heated to 80 °C for 15 h, then diluted with DCM and poured into brine. The layers are separated and the combined organic phases are dried over MgS04, filtered, and concentrated in vacuo. The crude product is purified by reverse phase column chromatography on CI 8 (using a solvent gradient of 45- 95percent MeCN/H20 + 0.1percent TFA). The product fractions are neutralized with saturated sodium bicarbonate solution and brine. The organic phase is separated, then the aqueous phase is extracted with EtOAc. The combined organic phases are dried over MgS04, filtered and concentrated in vacuo to provide intermediate 1-6 (4.19 g).

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; acetonitrile; at 70℃; for 18h;Inert atmosphere;

Step B. Ethyl 1-[6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate To a flask containing the title compound from the above Step A (1.50 g, 4.69 mmol) were added <strong>[127972-00-3]2-methoxy-5-methylphenyl boronic acid</strong> (0.779 g, 4.69 mmol) and dichloro bis(triphenylphosphine) palladium (0.33 g, 0.469 mmol). Acetonitrile (12 mL) and sodium carbonate (11.7 mL of 1.0 M aqueous solution, 11.7 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 18 h, then was allowed to cool to room temperature and was poured into water. The mixture was extracted with EtOAc, and the organic was concentrated in vacuo. Purification by chromatography on silica gel (0 to 20percent EtOAc in hexanes, then 20 to 100percent EtOAc in hexanes) provided the title compound: LCMS m/z 406.4 [M+H]+; 1H NMR (500 MHz, CDCl3) delta 8.12 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.91 (t, J=8.0 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.19 (dd, J=8.0, 2.0 Hz, 1H), 6.91 (d, J=8.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 3.87 (s, 3H), 2.35 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).

Reference： [1]Patent: US2009/209556,2009,A1 .Location in patent: Page/Page column 22
[2]Patent: US2010/216764,2010,A1 .Location in patent: Page/Page column 29
[3]Patent: WO2012/122340,2012,A1 .Location in patent: Page/Page column 53
[4]Patent: US2013/210798,2013,A1 .Location in patent: Paragraph 0134; 0135

55
[ 3934-20-1 ]
[ 127972-00-3 ]
[ 1044766-08-6 ]

Yield	Reaction Conditions	Operation in experiment
41.3%	With sodium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 90℃;	Description 10a: 2-chloro-4-(2-methoxy-5-methylphenyl)pyrimidine (D10a); To a solution of 2,4-dichloropyrimidine (Aldrich, 5g, 33.56mmol) in DME (80ml) and H2O (8ml), were added 2-methoxy-5-methylphenylboronic acid (Aldrich, 5.85g, 35.23mmol), Na2CO3 (5.34g, 50.34mmol), Pd(OAc)2 (0.188g, 0.84mmol) and triphenylphosphine (0.44g, 1.68mmol), and then the mixture was heated at 900C overnight, then cooled and poured into water. After extraction with CH2CI2, the organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by chromatography on silicagel (CH2CI2/Chex, 3/2 then 4/1 ). The title compound was obtained as a colorless oil which crystallised (3.25g, yield= 41.3percent). LC/MS: 235.1 (M+H), Rt= 3.27min. 1H NMR (CDCI3, ppm) : 8.58 (d, 1 H), 7.98 (d, 1 H), 7.89 (sd, 1 H), 7.28 (dd, 1 H), 6.93 (d, 1 H), 3.90 (s, 3H), 2.38 (s, 3H).

Reference： [1]Patent: WO2010/15653,2010,A1 .Location in patent: Page/Page column 44

56
[ 66-77-3 ]
[ 127972-00-3 ]
C₁₉H₁₈O₂ [ No CAS ]
[ 1196789-13-5 ]

Reference： [1]Chemical Communications,2009,p. 5713 - 5715

57
[ 1269818-09-8 ]
[ 127972-00-3 ]
[ 1269818-11-2 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 4200 - 4203

58
[ 51699-89-9 ]
[ 127972-00-3 ]
[ 71128-90-0 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

59
[ 31106-74-8 ]
[ 127972-00-3 ]
[ 110355-20-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

60
[ 31106-74-8 ]
[ 127972-00-3 ]
[ 110355-19-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

61
[ 443-41-4 ]
[ 127972-00-3 ]
[ 1310744-26-3 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

62
[ 443-41-4 ]
[ 127972-00-3 ]
[ 1310744-38-7 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

63
[ 22812-61-9 ]
[ 127972-00-3 ]
[ 1310744-24-1 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

64
[ 22812-61-9 ]
[ 127972-00-3 ]
[ 1310744-35-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

65
[ 174913-44-1 ]
[ 127972-00-3 ]
[ 1310744-33-2 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

66
[ 174913-44-1 ]
[ 127972-00-3 ]
[ 1310744-36-5 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

67
[ 3336-39-8 ]
[ 127972-00-3 ]
[ 1310744-34-3 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

68
[ 3336-39-8 ]
[ 127972-00-3 ]
[ 1310744-22-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5747 - 5758

69
[ 583-55-1 ]
[ 127972-00-3 ]
2'-bromo-2-methoxy-5-methylbiphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16955 - 16958,4

70
[ 127972-00-3 ]
C₁₃H₁₁BrO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16955 - 16958,4

71
[ 127972-00-3 ]
C₂₉H₂₉BrOSi [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16955 - 16958,4

72
[ 1422022-42-1 ]
[ 127972-00-3 ]
[ 1422021-15-5 ]

Yield	Reaction Conditions	Operation in experiment
7.6 mg	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 130℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step (b): 4'-hydroxy-2-iodo-5-(trifluoromethyl)-[l,r-biphenyl]-3-carboxamide (20 mg, 0.05 mmol), (2- methoxy-5-methylphenyl)boronic acid (16.3 mg, 0.10 mmol), PdCl2(PPh3)2 (3.45 mg, 0.005 mmol) and K2C03 (20.3 mg, 0.15 mmol) were mixed in DME/EtOH H20 (1 mL, 4:1 :1) under nitrogen. The reaction mixture was heated in microwave at 130 °C for 30 min, cooled to room temperature, filtered through ceiite and evaporated under reduced pressure. The crude mixture was purified on preparative HPLC using MeCN/acidic H20 (0 - 20 percent MeCN) as mobile phase. 7.6 mg 4-hydroxy-2"-methoxy-5"-methyl-5'- (trifluoromethyl)-[l,i':2,,l"-terphenyl]-3'-carboxamide (E288) was obtained. ES/MS m/z: 402.2 (M+H), 400.4 (M-H); 'H NMR (MeOD, 500MHz): 7.73 (d, 1H, J=1.6Hz), 7.64 (d, 1H, J=1.6Hz), 7.03 (m, 1H), 6.88 (m, 2H), 6.80 (d, 1H, J=2.0Hz), 6.74 (d, 1H, J=8.4Hz), 6.57 (m, 2H), 3.54 (s, 3H) and 2.15 (s, 3H).
7.6 mg	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 130℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step (b): 4'-hydroxy-2-iodo-5-(trifluoromethyl)-[1,1'-biphenyl]-3-carboxamide (20 mg, 0.05 mmol), <strong>[127972-00-3](2-methoxy-5-methylphenyl)boronic acid</strong> (16.3 mg, 0.10 mmol), PdCl2(PPh3)2 (3.45 mg, 0.005 mmol) and K2CO3 (20.3 mg, 0.15 mmol) were mixed in DME/EtOH/H2O (1 mL, 4:1:1) under nitrogen. The reaction mixture was heated in microwave at 130° C. for 30 min, cooled to room temperature, filtered through celite and evaporated under reduced pressure. The crude mixture was purified on preparative HPLC using MeCN/acidic H2O (0-20percent MeCN) as mobile phase. 7.6 mg 4-hydroxy-2"-methoxy-5"-methyl-5'-(trifluoromethyl)-[1,1':2',1"-terphenyl]-3'-carboxamide (E288) was obtained. ES/MS m/z: 402.2 (M+H), 400.4 (M-H); 1H NMR (MeOD, 500 MHz): 7.73 (d, 1H, J=1.6 Hz), 7.64 (d, 1H, J=1.6 Hz), 7.03 (m, 1H), 6.88 (m, 2H), 6.80 (d, 1H, J=2.0 Hz), 6.74 (d, 1H, J=8.4 Hz), 6.57 (m, 2H), 3.54 (s, 3H) and 2.15 (s, 3H).

Reference： [1]Patent: WO2013/17654,2013,A1 .Location in patent: Page/Page column 107
[2]Patent: US2014/323518,2014,A1 .Location in patent: Paragraph 0208

73
[ 127972-00-3 ]
[ 2216-94-6 ]
C₁₉H₂₀O₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6748 - 6752
Angew. Chem.,2013,vol. 125,p. 6880 - 6884

74
[ 127972-00-3 ]
(E)-3-(2-methoxy-5-methylphenyl)-3-phenylacrylic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6748 - 6752
Angew. Chem.,2013,vol. 125,p. 6880 - 6884

75
[ 127972-00-3 ]
(+)-3-(2-methoxy-5-methylphenyl)-3-phenylpropanoic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6748 - 6752
Angew. Chem.,2013,vol. 125,p. 6880 - 6884

76
[ 127972-00-3 ]
[ 1398414-30-6 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 9755 - 9758

77
[ 127972-00-3 ]
C₁₅H₁₂F₃NO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 9755 - 9758

78
[ 127972-00-3 ]
C₁₈H₁₈F₃NO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 9755 - 9758

79
[ 127972-00-3 ]
C₁₈H₁₉ClF₃NO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 9755 - 9758

80
[ 127972-00-3 ]
C₁₈H₁₈F₃NO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 9755 - 9758

81
2-[1-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazole-1-yl)-3-methylphenyl-2-yl]methyloxy}-4-bromothiazole [ No CAS ]
[ 127972-00-3 ]
2-[1-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazole-1-yl)-3-methylphenyl-2-yl]methyloxy}-4-(5-methyl-2-methoxyphenyl)thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.29 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride; In 1,4-dioxane; for 5h;Reflux;	Preparation example 148A mixture of Present compound (T057) 0.30 g, <strong>[127972-00-3]5-methyl-2-methoxyphenylboronic acid</strong> 0.26 g, cesium fluoride 0.42 g,[1,1? -bis(diphenylphosphino) ferrocene]palladium(II) dichioride dichioromethane adduct 0.06 g and dioxane 6 mL was stirred with heating under reflux for five hours. After cooling the reaction mixtures, the mixtures werefiltered and the filtrates were concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 2-[1--(4,5- dihydro-4--methyl-5-oxo-1H-tetrazole-1-yl) -3-methylphenyl-2- yl]methyloxy}-4- (5?methyl-2-methoxyphenyl)thiazole(hereinafter, referred to as ??Present compound (T148) ?0.29 g.?H NMR (CDC13) 5: 2.36 (3H, 5), 2.55 (3H, s), 3.56 (3H, s),3.87 (3H, s), 5.58 (2H, s), 6.83 (1H, d, J = 8.2 Hz), 7.05(1H, ddd, J 8.2, 1.6, 0.7 Hz), 7.25 (1H, dd, J = 6.9, 2.3Hz), 7.32 (1H, s), 7.36-7.42 (2H, rn), 7.91 (1H, d, J = 2.3Hz)

Reference： [1]Patent: WO2013/162077,2013,A1 .Location in patent: Paragraph 0431

82
[ 104-93-8 ]
[ 121-43-7 ]
[ 127972-00-3 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986

83
[ 127972-00-3 ]
6′,6′′-(2-methoxy-5-methyl-1,3-phenylene)bis-(6-(2-methoxy-5-methylphenyl)-2,2′-bipyridine) monohydrate [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986

84
[ 127972-00-3 ]
2,2′-(6′,6′′-(2-hydroxy-5-methyl-1,3-phenylene)bis-(2,2′-bipyridine-6′,6-diyl))bis(4-methylphenol)*monohydrate [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986

85
[ 127972-00-3 ]
[(2,2′-(6′,6′′-(2-hydroxy-5-methyl-1,3-phenylene)bis-(2,2′-bipyridine-6′,6-diyl))bis(4-methylphenol)(-3H))Zn2(OAc)]*MeOH [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986

86
[ 127972-00-3 ]
[(2,2′-(6′,6′′-(2-hydroxy-5-methyl-1,3-phenylene)bis-(2,2′-bipyridine-6′,6-diyl))bis(4-methylphenol)(-3H))2Ni4][OAc]2*14H2O [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986

87
[ 49669-22-9 ]
[ 127972-00-3 ]
6-bromo-6′-(2-methoxy-5-methylphenyl)-2,2′-bipyridine [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986

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Precautionary Statements-General
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Response
Code	Phrase
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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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.
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P361	Remove/Take off immediately all contaminated clothing.
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P370	In case of fire:
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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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.
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Physical hazards
Code	Phrase
H200	Unstable explosive
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
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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
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H332	Harmful if inhaled
H333	May be harmful if inhaled
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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. 127972-00-3 ] {[proInfo.proName]}

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[ 127972-00-3 ] Synthesis Path-Upstream 1~4

[ 127972-00-3 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 127972-00-3 ]

Organoboron

Aryls

Ethers

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[ 127972-00-3 ]