[ CAS No. 192182-54-0 ] {[proInfo.proName]}

Name: 192182-54-0|3,5-Dimethoxybenzeneboronic acid|98%
Brand: Ambeed
SKU: A154620
Price: 9.0 USD
Availability: InStock
Rating: 94 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 192182-54-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 192182-54-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 192182-54-0 ]

SDS Specification

Alternatived Products of [ 192182-54-0 ]

Product Details of [ 192182-54-0 ]

CAS No. :	192182-54-0	MDL No. :	MFCD03095127
Formula :	C₈H₁₁BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XUIURRYWQBBCCK-UHFFFAOYSA-N
M.W :	181.98	Pubchem ID :	4374257
Synonyms :		Chemical Name :	3,5-Dimethoxybenzeneboronic acid

Calculated chemistry of [ 192182-54-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	49.25
TPSA :	58.92 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) :	-6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.77
Log Po/w (WLOGP) :	-0.62
Log Po/w (MLOGP) :	-0.25
Log Po/w (SILICOS-IT) :	-0.74
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) :	-1.6
Solubility :	4.6 mg/ml ; 0.0253 mol/l
Class :	Very soluble
Log S (Ali) :	-1.59
Solubility :	4.7 mg/ml ; 0.0258 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.54
Solubility :	5.21 mg/ml ; 0.0286 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 192182-54-0 ]

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

Application In Synthesis of [ 192182-54-0 ]

* 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 [ 192182-54-0 ]
Downstream synthetic route of [ 192182-54-0 ]

[ 192182-54-0 ] Synthesis Path-Upstream 1~17

1
[ 7677-24-9 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1] Chinese Journal of Chemistry, 2013, vol. 31, # 1, p. 27 - 30

2
[ 55305-43-6 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 519 - 522

3
[ 68-12-2 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 5, p. 2528 - 2531

4
[ 75-05-8 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13246 - 13252

5
[ 192182-54-0 ]
[ 25245-27-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1 h;	General procedure: A mixture of the arylboronic acid (0.55mmol), KF (96mg, 1.65mmol) and I₂ (127mg, 0.50mmol) in 1,4-dioxane (5mL) was stirred at 80°C for 1h. Then it was filtered through silica gel, eluting with Et₂O (10mL) and the solvent was removed by rotary evaporation. When necessary, the product was purified by chromatography on silica gel (petroleum ether/Et₂O 98:2).

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1122 - 1123

6
[ 20469-65-2 ]
[ 192182-54-0 ]

Reference： [1] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17500 - 17521
[2] Organic Letters, 2004, vol. 6, # 15, p. 2547 - 2550
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 10, p. 3012 - 3018
[4] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[5] Patent: WO2009/141386, 2009, A1, . Location in patent: Page/Page column 59; 67

7
[ 5419-55-6 ]
[ 20469-65-2 ]
[ 192182-54-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere Stage #2: at -78℃; for 2 h; Stage #3: With sulfuric acid In tetrahydrofuran; hexane at 20℃;	a. Synthesis of 3,5-dimethoxyphenylboronicacid: In a flame dried vessel, cooled under argon 3,5-dimethoxy bromo benzene (3 g, 13.82 mmol) was taken in dry THF (36 ml). The resultant mixture was stirred to obtain a clear solution. This reaction mixture was then cooled to - 78 °C and maintained at this temperature for 15 min. This was followed by the addition of n-BuLi (10.92 ml, <n="27"/>2.1M in hexane) following which the reaction was stirred for 30 min. Triisopropyl borate ( 5.2 g, 27.64 mmol) was then added drop wise and the reaction was stirred at - 78 ⁰C for further 2hr. The reaction was subsequently allowed to warm to room temperature and acidified to pH 2 using sulphuric acid (2M). The resultant mixture was then extracted using ethylacetate. The extracts were combined, dried (MgSO₄) and the solvent removed under vacuum. The crude solid was purified using petroleum ether to yield 3,5-dimethoxy phenylboronic acid. Yield (92 percent).

Reference： [1] Patent: WO2008/118802, 2008, A1, . Location in patent: Page/Page column 25-26

8
[ 121-43-7 ]
[ 20469-65-2 ]
[ 192182-54-0 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 4, p. 935 - 945
[2] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17500 - 17521
[3] Patent: US6248738, 2001, B1,
[4] Polyhedron, 2012, vol. 33, # 1, p. 347 - 352

9
[ 7647-01-0 ]
[ 121-43-7 ]
[ 20469-65-2 ]
[ 7732-18-5 ]
[ 192182-54-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Stage #2: at -78 - 20℃;	PREPARATION 15 3,5-dimethoxyphenylboronic acidTo a solution of l-bromo-3, 5-dimethoxybenzene (5g, 23 mmol) in THF (100 mL) at -78 ⁰C was added n-Bu-Li (2.5M in hexane, 10 mL, 25 mmol). The mixture was stirred at -78 ⁰C for 30 min and transferred to a solution of B(OCH₃)₃ (3.1ml) in THF at -78 ⁰C. The resulting mixture was warmed up to rt and allowed to stir overnight. The reaction was quenched with 2N aq HCl and extracted with EtOAc. The combined organic extracts were dried over Na₂SO₄ and concentrated. The residue <n="119"/>was washed with hexane to give 2.2g (53percent yield) of 3,5-dimethoxyphenylboronic acid as a solid. MS m/z = 182.2 (M+H)+.

Reference： [1] Patent: WO2008/124582, 2008, A1, . Location in patent: Page/Page column 117-118

10
[ 151-10-0 ]
[ 192182-54-0 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 5, p. 761 - 764
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 519 - 522

11
[ 25245-27-6 ]
[ 192182-54-0 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 49, p. 11191 - 11204

12
[ 5419-55-6 ]
[ 25245-27-6 ]
[ 192182-54-0 ]

Reference： [1] Patent: US2003/27814, 2003, A1,

13
[ 557-91-5 ]
[ 121-43-7 ]
[ 7051-16-3 ]
[ 192182-54-0 ]

Reference： [1] Patent: US6252070, 2001, B1,

14
[ 365564-07-4 ]
[ 192182-54-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 519 - 522

15
[ 7051-16-3 ]
[ 192182-54-0 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673

16
[ 13675-18-8 ]
[ 20469-65-2 ]
[ 192182-54-0 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851

17
[ 76-09-5 ]
[ 192182-54-0 ]
[ 365564-07-4 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851

[ 192182-54-0 ] Synthesis Path-Downstream 1~84

1
[ 344-04-7 ]
[ 192182-54-0 ]
[ 671235-27-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With pyridine; palladium diacetate; triphenylphosphine at 23℃; for 24h;

Reference： [1]Göttker-Schnetmann, Inigo; White, Peter; Brookhart, Maurice [Journal of the American Chemical Society, 2004, vol. 126, # 6, p. 1804 - 1811]

2
[ 20469-65-2 ]
[ 192182-54-0 ]

Yield	Reaction Conditions	Operation in experiment
		f-BuLi (1.7 M in pentatne, 63 ml_, 106 mmol, 2.1 equiv) was added dropwise to a cold (-78C) solution of 3,5-dimethoxy-bromobenzene (1 1 g, 50.7 mmol) in THF (400 ml_), under an argon atmosphere. The yellow mixture si stirred for 45 min at -78C. Trimethyl borate (20 ml_, 179 mmol, 3.5 equiv) was then added. The colorless reaction mixture was allowed to warm to 00C, quenched by addition of a saturated solution of NH4CI (5 ml_), and concentrated. The residue was diluted with EtOAc/NH4CI (saturated aqueous solution), and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated. The residue was triturated in Et2O to provide 6.8 g of the title compound as a white solid: ESI-MS: 183.1 [M+H]+; tR= 2.70 min (System 1 ).

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 17500 - 17521
[2]Organic Letters,2004,vol. 6,p. 2547 - 2550
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 3012 - 3018
[4]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673
[5]Patent: WO2009/141386,2009,A1 .Location in patent: Page/Page column 59; 67

3
[ 5111-65-9 ]
[ 192182-54-0 ]
[ 869788-93-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene for 5h; Heating;
50%	With potassium phosphate In 1,4-dioxane at 80℃;
	With 1,3-dibenzyl-1H-benzimidazol-3-ium bromide; palladium diacetate; sodium hydride In N,N-dimethyl-formamide; mineral oil at 130℃; for 1h;	3.7. General procedure for palladium-catalyzed Suzuki{Miyaura cross-coupling reactions and GCanalyses General procedure: The solution of Pd(OAc)2 in DMF, the solution of the ligand in DMF, aryl bromide (0.5 mmol), 3,5-dimethoxyphenylboronic acid (0.091 g, 0.75 mmol), NaH (0.030 g, 0.75 mmol), and an additional amountof DMF (to have a nal reaction volume of 1.5 mL) were put into a 10 mL reaction ask. The reaction mixturewas then heated for 1 h at 130 C. After cooling to room temperature, 1 mL of the reaction mixture was passedthrough a Millipore lter and analyzed by GC-MS.The runs were carried out using an ArBr/Pd ratio of 10,000. The calibration was based on diethyleneglycol monobuthyl ether. Conversions given in Tables 1-3 were averaged over two runs and have been calculatedrelatively to the aryl bromide.

	With 1,3‐dibenzyl‐(5,6‐dimethyl)benzimidazolium bromide; palladium diacetate; sodium hydride In N,N-dimethyl-formamide; mineral oil at 130℃; for 1h;	3.7. General procedure for palladium-catalyzed Suzuki{Miyaura cross-coupling reactions and GCanalyses General procedure: The solution of Pd(OAc)2 in DMF, the solution of the ligand in DMF, aryl bromide (0.5 mmol), 3,5-dimethoxyphenylboronic acid (0.091 g, 0.75 mmol), NaH (0.030 g, 0.75 mmol), and an additional amountof DMF (to have a nal reaction volume of 1.5 mL) were put into a 10 mL reaction ask. The reaction mixturewas then heated for 1 h at 130 C. After cooling to room temperature, 1 mL of the reaction mixture was passedthrough a Millipore lter and analyzed by GC-MS.The runs were carried out using an ArBr/Pd ratio of 10,000. The calibration was based on diethyleneglycol monobuthyl ether. Conversions given in Tables 1-3 were averaged over two runs and have been calculatedrelatively to the aryl bromide.
	With C₆₉H₈₁N₂O₈⁽¹⁺⁾*Br^(1-); palladium diacetate; sodium hydride In N,N-dimethyl-formamide at 130℃; for 1h;	3.7. General procedure for palladium-catalyzed Suzuki{Miyaura cross-coupling reactions and GCanalyses General procedure: The solution of Pd(OAc)2 in DMF, the solution of the ligand in DMF, aryl bromide (0.5 mmol), 3,5-dimethoxyphenylboronic acid (0.091 g, 0.75 mmol), NaH (0.030 g, 0.75 mmol), and an additional amountof DMF (to have a nal reaction volume of 1.5 mL) were put into a 10 mL reaction ask. The reaction mixturewas then heated for 1 h at 130 C. After cooling to room temperature, 1 mL of the reaction mixture was passedthrough a Millipore lter and analyzed by GC-MS.The runs were carried out using an ArBr/Pd ratio of 10,000. The calibration was based on diethyleneglycol monobuthyl ether. Conversions given in Tables 1-3 were averaged over two runs and have been calculatedrelatively to the aryl bromide.

Reference： [1]Roberti, Marinella; Pizzirani, Daniela; Recanatini, Maurizio; Simoni, Daniele; Grimaudo, Stefania; Di Cristina, Antonietta; Abbadessa, Vincenzo; Gebbia, Nicola; Tolomeo, Manlio [Journal of Medicinal Chemistry, 2006, vol. 49, # 10, p. 3012 - 3018]
[2]Minutolo, Filippo; Sala, Giusy; Bagnacani, Annalisa; Bertini, Simone; Carboni, Isabella; Placanica, Giorgio; Prota, Giovanni; Rapposelli, Simona; Sacchi, Nicoletta; Macchia, Marco; Ghidoni, Riccardo [Journal of Medicinal Chemistry, 2005, vol. 48, # 22, p. 6783 - 6786]
[3]Işci, Ümit; Aygün, Muhittin; Sevincek, Resul; Zorlu, Yunus; Dumoulin, Fabienne [Turkish Journal of Chemistry, 2015, vol. 39, # 6, p. 1300 - 1309]
[4]Işci, Ümit; Aygün, Muhittin; Sevincek, Resul; Zorlu, Yunus; Dumoulin, Fabienne [Turkish Journal of Chemistry, 2015, vol. 39, # 6, p. 1300 - 1309]
[5]Işci, Ümit; Aygün, Muhittin; Sevincek, Resul; Zorlu, Yunus; Dumoulin, Fabienne [Turkish Journal of Chemistry, 2015, vol. 39, # 6, p. 1300 - 1309]

4
hexane chloroform [ No CAS ]
[ 482627-80-5 ]
[ 118062-05-8 ]
[ 192182-54-0 ]
[ 482627-31-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 24 1,4-Bis[5-(2,3,4-trimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine Following the procedure of Example 1, an oil was obtained from 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (115.0 mg, 0.280 mmol) synthesised in Reference Example 1 and <strong>[118062-05-8]2,3,4-trimethoxyphenylboronic acid</strong> (130.0 mg, 0.620 mmol) synthesised from 2,3,4-trimethoxybromobenzne (J. Org. Chem., 23, 16-17 (1958)) in a similar manner as in Reference Example 2. Chloroform-hexane was added to the oil, and the resulting precipitate was collected by filtration to yield the title compound as a yellow crystalline powder (melting point: 192.0-194.0 C.) (57.0 mg, yield: 35%). 1H-NMR (CDCl3) delta: 2.17 (tt, J=6.1, 6.1 Hz, 2 H), 3.65 (dd, J=6.1, 6.1 Hz, 4 H), 3.72 (s, 6 H), 3.89 (s, 6 H), 3.92 (s, 6 H), 3.96 (s, 4 H), 6.60 (d, J=8.8 Hz, 2 H), 6.73 (d, J=8.5 Hz, 2 H), 7.00 (d, J=8.5 Hz, 2 H), 7.67 (dd, J=2.4, 8.8 Hz, 2 H), 8.28 (d, J=2.4 Hz, 2 H).

Reference： [1]Patent: US2003/27814,2003,A1

5
[ 18982-54-2 ]
[ 192182-54-0 ]
[ 1065544-17-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium fluoride; palladium diacetate; johnphos In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;
88%	With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 0 - 20℃; for 20.5h; Inert atmosphere;
85%	With sodium carbonate In water; N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Hwang, Seung Jun; Kim, Hyun Jin; Chang, Sukbok [Organic Letters, 2009, vol. 11, # 20, p. 4588 - 4591]
[2]Kwon, Yongseok; Cho, Hyunkyung; Kim, Sanghee [Organic Letters, 2013, vol. 15, # 4, p. 920 - 923]
[3]Li, Guijie; Wang, Erjuan; Chen, Haoyi; Li, Hongfeng; Liu, Yuanhong; Wang, Peng George [Tetrahedron, 2008, vol. 64, # 38, p. 9033 - 9043]

6
[ 192182-54-0 ]
[ 42087-81-0 ]
[ 1166398-61-3 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2936 - 2939
[2]Journal of Organic Chemistry,2010,vol. 75,p. 8224 - 8233

7
[ 148231-12-3 ]
[ 192182-54-0 ]
[ 1197331-92-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; at 105℃; for 2h;Inert atmosphere;	A mixture of 3,5-dimethoxyphenylboronic acid (Step 1.8) (3.38 g, 18.6 mmol) in EtOH (15 ml.) was added dropwise to a mixture of <strong>[148231-12-3]5,8-dibromo-quinoxaline</strong> (Step 1.5) (10.7 g, 37.1 mmol, 2 equiv), PdCI2(dppf) (530 mg, 0.7 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 37 ml_, 74.3 mmol, 4 equiv) in toluene (100 ml.) at 1050C, under an argon atmosphere. The reaction mixture was stirred at 105 0C for 2 h, allowed to cool to rt, diluted with EtOAc and H2O, filtered through a pad of celite and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by trituration in DCM, followed by silica gel column chromatography (Hex/EtOAc, 4:1 ) to afford 4.54 g of the title compound as a yellow solid: ES-MS: 345.0 [M+H]+; tR= 5.13 min (System 1 ); Rf = 0.17 (Hex/EtOAc, 4:1 ).

Reference： [1]Patent: WO2009/141386,2009,A1 .Location in patent: Page/Page column 59; 64; 66; 174-175

8
[ 928839-62-7 ]
[ 192182-54-0 ]
[ 1197333-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; at 105℃; for 1.0h;Inert atmosphere;	A mixture of 3,5-dimethoxyphenylboronic acid (217 mg, 1.19 mmol, 1.2 equiv) (Step 1.8) inEtOH (0.5 ml.) was added dropwise to a mixture of delta-bromo-quinoline-delta-carboxylic acid <n="164"/>(Step 159.3) (250 mg, 0.99 mmol), PdCI2(dppf) (22mg, 0.03 mmol, 0.03 equiv), Na2CO3 (2M solution in H2O, 1 ml_, 3.97mmol, 4equiv) in toluene (5ml_) at 1050C, under an argon atmosphere. The reaction mixture was stirred at 1050C for 1 h, allowed to cool to rt, diluted with EtOAc and H2O, basified by addition of a 2N aqueous solution of NaOH (2ml_), filtered through a pad of celite and the filtrate was extracted with EtOAc. The aqueous layer was separated and acidified to pH 5. The resulting precipitate was collected by vacuum filtration to provide 248mg of the title compound as a white solid: ESI-MS:310.1 [M+H]+; tR=4.06min (System 1 ).

Reference： [1]Patent: WO2009/141386,2009,A1 .Location in patent: Page/Page column 162-163

9
[ 192182-54-0 ]
[ 1761-61-1 ]
[ 1063714-84-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: 3,5-dimethoxyphenylboronic acid; 5-bromosalicyclaldehyde With potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water	3.b b. Synthesis of 3,5-dimethoxyphenylsalicylaldehyde: In a round-bottom flask equipped with a magnetic stirrer, 5-bromosalicylaldehyde (1 g, 4.97 mmol), K2CO3 (2.061 g, 14.91 mmol), 3,5-dimethoxyphenylboronic acid (0.9954 g, 5.47mmol), triphenyl-phosphine (1 mol%) and Pd(OAc)2 (1 mol%) were taken in DME: water (1 : 1) (12 ml). The mixture was stirred at room temperature under an atmosphere of m'trogen for 24 hours. The reaction mixture was then acidified using HCl (IN) followed by extraction with ethyl acetate . The extracts were combined, dried (MgSO4) and the solvent removed under vacuum. The crude solid was purifed by flash chromatography to isolate the desired 3,5- dimethoxyphenylsalicylaldehyde. Yield (48 %).
45%	With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 20℃; for 24h; Inert atmosphere;
	With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 20℃; for 24h;

Reference： [1]Current Patent Assignee: UNIVERSITY OF MINNESOTA SYSTEM - WO2008/118802, 2008, A1 Location in patent: Page/Page column 26
[2]Location in patent: experimental part Das, Sonia G.; Doshi, Jignesh M.; Tian, Defeng; Addo, Sadiya N.; Srinivasan, Balasubramanian; Hermanson, David L.; Xing, Chengguo [Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5937 - 5949]
[3]Location in patent: scheme or table Aridoss, Gopalakrishnan; Zhou, Bo; Hermanson, David L.; Bleeker, Nicholas P.; Xing, Chengguo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5566 - 5581]

10
[ 10401-18-0 ]
[ 192182-54-0 ]
[ 1194487-30-3 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 8709 - 8712

11
[ 33994-44-4 ]
[ 192182-54-0 ]
[ 1071836-13-9 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 17500 - 17521

12
[ 55305-43-6 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 519 - 522

13
[ 365564-07-4 ]
[ 192182-54-0 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 519 - 522

14
[ 124-11-8 ]
[ 192182-54-0 ]
[ 188975-30-6 ]
[ 1286254-43-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In N,N-dimethyl acetamide at 55℃; for 12h; regioselective reaction;

Reference： [1]Liao, Longyan; Jana, Ranjan; Urkalan, Kaveri Balan; Sigman, Matthew S. [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 5784 - 5787]

15
[ 151583-29-8 ]
[ 192182-54-0 ]
[ 1358694-32-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 5.0h;Inert atmosphere; Reflux;	General procedure: In distinct reactors, 3-(bromophenyl)-propionic methyl esters 16, 17 (1.0 equiv) were dissolved in toluene (7 mL). Phenyl boronic acids 18-21 (2 equiv) in EtOH (3.5 mL) and Na2CO3 2 M (2 M, aq, 3.0 equiv) were then added to the corresponding reactors, and the resulting mixtures were deoxygenated with a stream of N2. After 10 min, Pd(PPh3)4 (0.005 equiv) was added and each mixture was stirred at reflux temperature for 5 h under N2, then cooled to room temperature and treated as follows. Each solution was poured into a mixture of H2O (5 mL) and Et2O (5 mL), and the two phases were separated. The aqueous layer was washed with Et2O (5 mL), and the organic phases were combined and washed with 1 M NaOH (5 mL), followed by brine (5 mL), then dried over Na2SO4 and evaporated. Purification of each crude product performed by flash chromatography on silica gel (petroleum ether/EtOAc = 8/2) yielded the corresponding biphenyl propanoic acid methyl esters 22a-e (Scheme 3).

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 48,p. 206 - 213

16
[ 75567-84-9 ]
[ 192182-54-0 ]
[ 1071836-13-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 5h;Inert atmosphere; Reflux;	General procedure: In distinct reactors, 3-(bromophenyl)-propionic methyl esters 16, 17 (1.0 equiv) were dissolved in toluene (7 mL). Phenyl boronic acids 18-21 (2 equiv) in EtOH (3.5 mL) and Na2CO3 2 M (2 M, aq, 3.0 equiv) were then added to the corresponding reactors, and the resulting mixtures were deoxygenated with a stream of N2. After 10 min, Pd(PPh3)4 (0.005 equiv) was added and each mixture was stirred at reflux temperature for 5 h under N2, then cooled to room temperature and treated as follows. Each solution was poured into a mixture of H2O (5 mL) and Et2O (5 mL), and the two phases were separated. The aqueous layer was washed with Et2O (5 mL), and the organic phases were combined and washed with 1 M NaOH (5 mL), followed by brine (5 mL), then dried over Na2SO4 and evaporated. Purification of each crude product performed by flash chromatography on silica gel (petroleum ether/EtOAc = 8/2) yielded the corresponding biphenyl propanoic acid methyl esters 22a-e (Scheme 3).

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 48,p. 206 - 213

17
[ 68-12-2 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 2528 - 2531

18
[ 850012-44-1 ]
[ 192182-54-0 ]
[ 1373752-25-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 7262 - 7265

19
[ 19063-55-9 ]
[ 192182-54-0 ]
[ 1063714-86-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5566 - 5581

20
[ 192182-54-0 ]
[ 175278-17-8 ]
[ 1412911-98-8 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6280 - 6287,8

21
[ 192182-54-0 ]
[ 175278-17-8 ]
[ 1412912-60-7 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6280 - 6287,8

22
[ 444-14-4 ]
[ 192182-54-0 ]
[ 1412912-61-8 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6280 - 6287,8

23
[ 180340-70-9 ]
[ 192182-54-0 ]
[ 1412912-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 70℃; for 2h;

Reference： [1]Augustine, John Kallikat; Alagarsamy, Padma; Jothi, Anandh; Bombrun, Agnes [Tetrahedron Letters, 2012, vol. 53, # 46, p. 6280 - 6287,8] Augustine, John Kallikat; Bombrun, Agnes; Alagarsamy, Padma; Jothi, Anandh [Tetrahedron Letters, 2012, vol. 53, # 46, p. 6280 - 6287]

24
[ 7677-24-9 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 27 - 30

25
[ 192182-54-0 ]
[ 290368-00-2 ]
C₁₅H₁₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 120℃; for 1h;Microwave irradiation;	General procedure: <strong>[290368-00-2]ter<strong>[290368-00-2]t-butyl 3-iodo-1H-indazole-1-carboxylate</strong></strong> (S2, 100 mg, 0.29 mmol) was placed in a microwave vial and dissolved in 1,4-dioxane (11.5 mL). 3-Methoxyphenylboronic acid (88 mg, 0.58 mmol, 2.0 equiv) and tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol, 0.06 equiv) were added, and the resulting mixture was sparged thoroughly with nitrogen. An aqueous solution of sodium carbonate (2.0 M, 0.65 mL, 1.3 mmol, 4.5 equiv) was then added. The biphasic mixture was microwaved for 1 hour at a reaction temperature of 120 C. After cooling to room temperature, the reaction was diluted with ethyl acetate (2 mL), and then filtered through a celite pad with additional ethyl acetate. The filtrate was concentrated under reduced pressure to give an oil. The crude material was purified by column chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 30/70) to give the title compound as an oil (58.0 mg, 89%).

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1501 - 1507

26
[ 16308-68-2 ]
[ 459-64-3 ]
[ 192182-54-0 ]
3-(3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)propyl phenyl carbonate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5008 - 5011

27
[ 953039-25-3 ]
[ 192182-54-0 ]
[ 1538605-46-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 80℃; for 3h; Inert atmosphere;	10 Synthesis of 2-chloro-6-(3 ,5-dimethoxyphenyl)-8-fluoroquinazoline A mixture of 6-bromo-2-chloro-8-fluoroquinazoline (4.0 g, 15.4 mmol), 3,5-dimethoxyphenylboronic acid (4.47 g, 16.9 mmol), cesium carbonate (10.0 g, 30.8 mmol) andPd(PPh3)2C12 (236 mg, 0.77 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stuffed at 80 °C for 3 h. Both TLC and LCMS showed the reaction was completed. The reaction mixture was cooled to RT and directly concentrated. The residue was purified by silica gel chromatography (petroleum ether:dichloromethane = 2:1 to 1:1) to afford the title compound (2.5 g, 51%) as a yellow solid. MS (ES+) C16H12C1FN202 requires: 3 18/320,found: 3 19/321 [M + Hf’.
51%	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran; water at 80℃; for 3h; Inert atmosphere;	8; 14 Step 14: Synthesis of 2-chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazoline A mixture of 6-bromo-2-chloro-8-fluoroquinazoline (4.0 g, 15.4 mmol), 3,5-dimethoxyphenylboronic acid (4.47 g, 16.9 mmol), cesium carbonate (10.0 g, 30.8 mmol) and Pd(PPh3)2Cl2 (236 mg, 0.77 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and directly concentrated. The residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1) to afford the title compound (2.5 g, 51%) as a yellow solid. MS (ES+) C16H12ClFN2O2 requires: 318/320, found: 319/321 [M+H]+.

Reference： [1]Current Patent Assignee: BLUEPRINT MEDICINES CORP - WO2014/11900, 2014, A2 Location in patent: Page/Page column 77; 79
[2]Current Patent Assignee: BLUEPRINT MEDICINES CORP - US2015/119405, 2015, A1 Location in patent: Paragraph 0446; 0457; 0458

28
[ 882672-05-1 ]
[ 192182-54-0 ]
[ 1538605-05-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; water; for 4.0h;Reflux; Inert atmosphere;	SM1 (5.00 g, 20.5 mmol) and SM2 (3.73 g, 20.5 mmol) were dissolved in tetrahydrofuran (30 ml), added with a solution of cesium carbonate (20.00 g, 61.5 mmol) in water (30 ml), and added with a catalytic amount of Pd(PPh3)Cl2. The resulting mixture was heated to reflux for 4 h under nitrogen atmosphere. (0060) The reaction solution was concentrated to dryness and extracted with ethyl acetate. The organic phase was washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was subjected to column chromatography (200-300 mesh silica gel, petroleum ether/ethyl acetate=10/1) to obtain intermediate I-1 (3.80 g, yield of 62%) as a pale yellow solid.
62%	With trans-bis(triphenylphosphine)palladium dichloride; caesium carbonate; In tetrahydrofuran; water; for 4.0h;Inert atmosphere; Reflux;	SM1 (5.00g, 20.5mmol) and SM2 (3.73g, 20.5mmol) was dissolved in tetrahydrofuran (30ml) was added cesium carbonate (20.00g, 61.5mmol) in water (30ml) was added a catalytic amount of Pd(PPh3)Cl2, the mixture was heated to reflux under a nitrogen atmosphere for 4 hours. The reaction solution was concentrated to dryness, extracted with ethyl acetate.(200-300 mesh silica gel, petroleum ether / ethyl acetate = 10/1) to give the organic phase was washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product subjected to column chromatography of Intermediate I- 1 (3.80g, 62% yield) as a pale yellow solid.
38%	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; water; at 80℃; for 3.0h;Inert atmosphere; Microwave irradiation;	Step 5: Synthesis of 2-chloro-6-(3,5-dimethoxyphenyl)quinazoline A mixture of <strong>[882672-05-1]6-bromo-2-chloroquinazoline</strong> (32) (5.0 g, 20.5 mmol), 3,5- dimethoxyphenylboronic acid (33) (3.7 g, 20.5 mmol), CS2CO3 (20.0 g, 61.5 mmol) and Pd(PPh3)2Cl2 (1.4 g, 2.1 mmol) in THF (50 mL), dioxane (50 mL) and water (10 mL) was degassed with N2 three times, and stirred at 80 C for 3 hours. An aliquot of the reaction mixture was analyzed by both TLC and LCMS, which indicated that the reaction had proceeded to completion. The mixture was cooled to room temperature, and extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc = 8: 1) to obtain 2-chloro-6-(3,5-dimethoxyphenyl)quinazoline (34) as a light yellow solid (2.4 g, 38%). MS (ES+) C16Hi3ClN202 requires: 300, found: 301, 303 [M + H]+.

38%	With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; water; at 80℃; for 3.0h;Inert atmosphere;	A mixture of <strong>[882672-05-1]6-bromo-2-chloroquinazoline</strong> (32) (5.0 g, 20.5 mmol), 3,5-dimethoxyphenylboronic acid (33) (3.7 g, 20.5 mmol), Cs2CO3 (20.0 g, 61.5 mmol) and Pd(PPh3)2Cl2 (1.4 g, 2.1 mmol) in THF (50 mL), dioxane (50 mL) and water (10 mL) was degassed with N2 three times, and stirred at 80 C. for 3 hours. An aliquot of the reaction mixture was analyzed by both TLC and LCMS, which indicated that the reaction had proceeded to completion. The mixture was cooled to room temperature, and extracted with EtOAc (3*200 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc=8:1) to obtain 2-chloro-6-(3,5-dimethoxyphenyl)quinazoline (34) as a light yellow solid (2.4 g, 38%). MS (ES+) C16H13ClN2O2 requires: 300, found: 301, 303 [M+H]+.
38%	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; water; for 3.0h;Inert atmosphere; Microwave irradiation;	A mixture of <strong>[882672-05-1]6-bromo-2-chloroquinazoline</strong> (32) (5.0 g, 20.5 mmol), 3,5-dimethoxyphenylboronic acid (33) (3.7 g, 20.5 mmol), Cs2CO3 (20.0 g, 61.5 mmol) and Pd(PPh3)2Cl2 (1.4 g, 2.1 mmol) in THF (50 mL), dioxane (50 mL) and water (10 mL) was degassed with N2 three times, and stirred at 80 C. for 3 hours. An aliquot of the reaction mixture was analyzed by both TLC and LCMS, which indicated that the reaction had proceeded to completion. The mixture was cooled to room temperature, and extracted with EtOAc (3×200 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc=8:1) to obtain 2-chloro-6-(3,5-dimethoxyphenyl)quinazoline (34) as a light yellow solid (2.4 g, 38%). MS (ES+) C16H13ClN2O2 requires: 300, found: 301, 303 [M+H]+.

Reference： [1]Patent: US2019/209564,2019,A1 .Location in patent: Paragraph 0057; 0058; 0059; 0060
[2]Patent: CN110386921,2019,A .Location in patent: Paragraph 0159-0165
[3]Patent: WO2014/11900,2014,A2 .Location in patent: Page/Page column 37; 38; 39
[4]Patent: US2015/197519,2015,A1 .Location in patent: Paragraph 0133; 0134
[5]Patent: US9695165,2017,B2 .Location in patent: Page/Page column 39

29
[ 1029720-65-7 ]
[ 192182-54-0 ]
[ 1585145-77-2 ]

Yield	Reaction Conditions	Operation in experiment
0.5 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; Sealed tube; Inert atmosphere;	1.1 Step 1.1: 3-chloro-7-(3,5-dimethoxyphenyl) isoquinoline: To a solution of 7-bromo-3-chloroisoquinoline (500 mg, 2.0 mmol) and 3,5- dimethoxyphenylboronic acid (364 mg, 2.0 mmol) in DME and water (1 : 1) in a sealed tube was added S-Phos (42 mg, 5 mole %) followed by Pd(OAc)2 (23 mg, 5 mole %) and disodium carbonate (262 mg, 2.47 mmol). The reaction mixture was purged with Argon, then heated at 90°C for O/N, allowed to cool to room temperature, diluted with EtOAc and water, filtered through a pad of celite and extracted with EtOAc. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The crude product was purified by Flash chromatography (n-Hexane: EtOAc (9: 1) to afford 0.5 g of the title compound as white solid. 1H NMR (400 MHz, CDC13) δ 9.12 (s, 1H), 8.15 - 8.11 (m, 1H), 7.96 (dd, J = 8.6, 1.8 Hz, 1H), 7.83 (d, J = 8.7 Hz, 1H), 7.75 (s, 1H), 6.82 (d, J = 2.2 Hz, 2H), 6.53 (t, J = 2.2 Hz, 1H), 3.89 (s, 6H). M/Z: 299.7, M+l : 300.3, tR= 3.44 min. (System 2)

Reference： [1]Current Patent Assignee: EVOTEC AG - WO2014/44846, 2014, A1 Location in patent: Page/Page column 24

30
[ 66191-86-4 ]
[ 192182-54-0 ]
[ 1624332-55-3 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 6752 - 6755

31
[ 1150617-54-1 ]
[ 192182-54-0 ]
[ 1614234-21-7 ]

Yield	Reaction Conditions	Operation in experiment
0.38 g	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 85℃;Sealed tube;	A mixture of <strong>[1150617-54-1]6-bromo-1H-pyrazolo[4,3-b]pyridine</strong> (0.3 g, 2 mmol;)(Annova Chem Cat. No. L05238), (3,5-dimethoxyphenyl)boronic acid (0.33 g, 1.8 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (100 mg, 0.1 mmol), and potassium phosphate (0.64 g, 3.0 mmol) in 1,4-dioxane (1 mL) and water (0.12 mL) was degassed and sealed. It was stirred at 85 C. overnight. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.38 g). LCMS (M+H)+=256.2.

Reference： [1]Patent: US2014/171405,2014,A1 .Location in patent: Paragraph 0444

32
[ 3572-43-8 ]
[ 192182-54-0 ]
[ 1618645-51-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	4.2 General procedure of Suzuki couplings reactions (3a-r, 5a-b) General procedure: The reaction was carried out in an Ace-pressure tube. To a dioxane suspension (3mL) of 1 (200mg, 0.53mmol), arylboronic acids (1.60mmol), K2CO3 (1M in water, 2mL), Pd(OAc)2 (5mol%) and ligand III (S-Phos, 10mol%) were added under argon atmosphere. The pressure tube was fitted with a Teflon cap and heated at 100°C (TLC control). The mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water. After removal of the solvent in vacuum, the coupling products were isolated by column chromatography in hexane/ethyl acetate.
58%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	16 4.2. General procedure of Suzuki couplings reactions (3a-r,5a-b) The reaction was carried out in an Ace-pressure tube. To a dioxane suspension (3 mL) of 1 (200 mg, 0.53 mmol), arylboronic acids (1.60 mmol), K2CO3 (1 M in water, 2 mL), Pd(OAc)2 (5 mol %) and ligand III (S-Phos, 10 mol %) were added under argon atmosphere. The pressure tube was fitted with a Teflon cap and heated at 100°C (TLC control). The mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water. After removal of the solvent in vacuum, the coupling products were isolated by column chromatography in hexane/ethyl acetate.

Reference： [1]Sharif, Muhammad; Pews-Davtyan, Anahit; Lukas, Jan; Pohlers, Susann; Rolfs, Arndt; Langer, Peter; Beller, Matthias [Tetrahedron, 2014, vol. 70, # 34, p. 5128 - 5135]
[2]Sharif, Muhammad; Pews-Davtyan, Anahit; Lukas, Jan; Pohlers, Susann; Rolfs, Arndt; Langer, Peter; Beller, Matthias [Tetrahedron, 2014, vol. 70, # 34, p. 5128 - 5135]

33
[ 757978-19-1 ]
[ 192182-54-0 ]
C₂₁H₁₇BrN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

34
[ 233770-01-9 ]
[ 192182-54-0 ]
C₁₃H₁₂BrNO₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7900 - 7915

35
[ 105309-59-9 ]
[ 192182-54-0 ]
tetrakis(3',5'-dimethoxy[1,1'-biphenyl]-4-yl)methane [ No CAS ]

Reference： [1]CrystEngComm,2013,vol. 15,p. 6845 - 6862

36
[ 25676-75-9 ]
[ 192182-54-0 ]
4-(3,5-dimethoxyphenyl)-1-methyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride; In water; toluene; for 48h;Reflux; Inert atmosphere;	General procedure: A deaerated mixture of <strong>[25676-75-9]4-bromo-1-methyl-1H-imidazole</strong> (10) (0.800g, 5.00mmol), an arylboronic acid 7 (10.0mmol), CsF (2.28g, 15.0mmol), PdCl2(dppf) (0.183g, 0.25mmol), and BnEt3NCl (0.057g, 0.25mmol) in toluene (30mL) and water (30mL) was heated at reflux under argon for 48h. The mixture was then cooled to room temperature and partitioned between water and AcOEt, and the organic extract was dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to provide the desired product. This procedure was used to prepare compounds 9a and 9b, both in 95% yield.

Reference： [1]Tetrahedron,2015,vol. 71,p. 2298 - 2305

37
[ 2302-25-2 ]
[ 192182-54-0 ]
[ 312583-37-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride; In water; toluene; for 96h;Inert atmosphere; Reflux;	General procedure: A deaerated mixture of 4(5)-bromo-1H-imidazole (6) (0.735g, 5.00mmol), an arylboronic acid 7 (10.0mmol), CsF (2.28g, 15.0mmol), PdCl2(dppf) (0.183g, 0.25mmol), and BnEt3NCl (0.057g, 0.25mmol) in toluene (30mL) and water (30mL) was heated at reflux under argon for 96h. The mixture was then cooled to room temperature and partitioned between water and AcOEt, and the organic extract was dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to provide the desired product. This procedure was used to prepare compounds 5a and 5b, in 75 and 95% yields.

Reference： [1]Tetrahedron,2015,vol. 71,p. 2298 - 2305

38
[ 192182-54-0 ]
[ 213382-45-7 ]
6-fluoro-3',5'-dimethoxy-4-nitrobiphenyl-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9 g	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In 1,4-dioxane; water at 90℃; for 3h; Inert atmosphere;	2 Step 2: Synthesis of 6-fluoro-3′,5′-dimethoxy-4-nitrobiphenyl-3-carbaldehyde A mixture of 5-bromo-4-fluoro-2-nitrobenzaldehyde (10.0 g, 40.0 mmol), 3,5-dimethoxyphenylboronic acid (7.3 g, 40.0 mmol), bis(triphenylphosphino) palladium(II) chloride (1.4 g, 2.0 mmol) and cesium carbonate (32.6 g, 100.0 mmol) in dioxane/ water (550 mL, v/v=10/1) was degassed with nitrogen for three times and heated at 90° C. for 3 hours. The mixture was cooled to room temperature, concentrated, diluted with ethyl acetate (1000 mL), and washed by water (500 mL) and brine (500 mL). The organic layer was dried, concentrated, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=8/1 to 5/1) to afford the title compound (9 g, 61%) as a yellow solid. MS (ES+) C15H12FNO5 requires: 305, found: 306 [M+H]+.

Reference： [1]Current Patent Assignee: BLUEPRINT MEDICINES CORP - US2015/119405, 2015, A1 Location in patent: Paragraph 0431; 0434; 0435

39
[ 953039-25-3 ]
[ 192182-54-0 ]
[ 1538605-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / water; tetrahydrofuran / 3 h / 80 °C / Inert atmosphere 2: sulfuryl dichloride / tetrahydrofuran / 1 h / 0 °C

Reference： [1]Current Patent Assignee: BLUEPRINT MEDICINES CORP - US2015/119405, 2015, A1

40
[ 1036756-07-6 ]
[ 192182-54-0 ]
2-chloro-6-(3,5-dimethoxyphenyl)-5-fluoroquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; caesium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere;	6 Step 6: Synthesis of 2-chloro-6-(3,5-dimethoxyphenyl)-5-fluoroquinazoline A mixture of 6-bromo-2-chloro-5-fluoroquinazoline (1.5 g, 5.74 mmol), 3,5-dimethoxyphenylboronic acid (1.15 g, 6.31 mmol), cerium carbonate (1.87 g, 5.74 mmol) and bis(tri-tert-butylphosphine)palladium (148 mg, 0.29 mmol) in THF (30 mL) and water (3 mL) was degassed with nitrogen for three times and stirred at 80° C. overnight. The mixture was cooled to room temperature and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=8:1) to get the title product as a white solid (1.3 g, 70%). MS (ES+) C16H12ClFN2O2 requires: 318, found: 319, 321 [M+H]+.

Reference： [1]Current Patent Assignee: BLUEPRINT MEDICINES CORP - US2015/119405, 2015, A1 Location in patent: Paragraph 0461; 0472; 0473

41
[ 99655-68-2 ]
[ 192182-54-0 ]
3-(3,5-dimethoxyphenyl)-1-(phenylsulfonyl)indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 100℃; for 17h; Inert atmosphere;

Reference： [1]Cooper, Stephen P.; Booker-Milburn, Kevin I. [Angewandte Chemie - International Edition, 2015, vol. 54, # 22, p. 6496 - 6500]

42
[ 75-05-8 ]
[ 192182-54-0 ]
[ 19179-31-8 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 13246 - 13252

43
[ 1813-33-8 ]
[ 192182-54-0 ]
[ 935520-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; toluene; for 12h;Reflux;	General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6844 - 6854

44
[ 7311-64-0 ]
[ 192182-54-0 ]
3-(3,5-dimethoxyphenyl)thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5484 - 5487

45
[ 18698-96-9 ]
[ 192182-54-0 ]
2-(3',5'-dimethoxy-[1,1'-biphenyl]-2-yl)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: o-iodophenylacetic acid; 3,5-dimethoxyphenylboronic acid With lithium hydroxide In tetrahydrofuran; water at 20℃; for 0.116667h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In tetrahydrofuran; water at 80℃; for 14h; Inert atmosphere; Sealed tube;

Reference： [1]Motiwala, Hashim F.; Vekariya, Rakesh H.; Aubé, Jeffrey [Organic Letters, 2015, vol. 17, # 21, p. 5484 - 5487]

46
[ 22288-66-0 ]
[ 192182-54-0 ]
2-(3,5-dimethoxyphenyl)-4H-pyrido[1,2-a]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 2H,3H,4H-pyrido[1,2-a]pyrimidine-2,4-dione With potassium carbonate; p-toluenesulfonyl chloride In 1,4-dioxane; water at 25 - 28℃; for 1h; Stage #2: 3,5-dimethoxyphenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane; water at 100℃;	4.1.2 Typical experimental procedure for the synthesis of 2-aryl-4H-pyrido[1,2- a]pyrimidin-4-ones (3a-r): [21] General procedure: A mixture of the 4H-pyrido[1,2-a]pyrimidin-4-one (1mmol), and K2CO3 (2.5eq) in 1,4-dioxane (2mL) and H2O (1mL) taken in a round-bottomed flask and p-TsCl (1.3eq) was added to it. The mixture was stirred under open air for 1h at rt (25-28°C). The boronic acid (1.2eq) and Pd(PPh3)4 (3mol %) were subsequently added and the mixture was heated at 100°C under open air. Upon completion of reaction as indicated by TLC (1-1.5h), the resultant mixture was cooled to rt and extracted with EtOAc (2×25mL). The combined organic solution was washed with water (2×5mL) and brine (1×5mL), dried with anhyd. Na2SO4, and concentrated under reduced pressure. The column chromatographic purification of crude mass was performed on neutral alumina using EtOAc-hexane (30-40%) as eluting solvent afford the arylated products (3a-r).

Reference： [1]Priyadarshani, Garima; Amrutkar, Suyog; Nayak, Anmada; Banerjee, Uttam C.; Kundu, Chanakya N.; Guchhait, Sankar K. [European Journal of Medicinal Chemistry, 2016, vol. 122, p. 43 - 54]

47
[ 100-42-5 ]
[ 192182-54-0 ]
[ 22139-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro bis(acetonitrile) palladium(II); sodium carbonate; oxygen / N,N-dimethyl-formamide / 18 h / 50 °C 2: boron tribromide / dichloromethane / 24 h / -10 - 20 °C / Inert atmosphere

Reference： [1]Uzura, Saori; Sekine-Suzuki, Emiko; Nakanishi, Ikuo; Sonoda, Motohiro; Tanimori, Shinji [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3886 - 3891]

48
[ 1520-21-4 ]
[ 192182-54-0 ]
[ 586410-15-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With dichloro bis(acetonitrile) palladium(II); oxygen; sodium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	1. General synthetic procedure of stilbenes 4 General procedure: The mixture of styrene 2 (0.5 mmol) and phenylboronic acid 3 (182 mg, 1.0 mmol), (CH3CN)2PdCl2 (13 mg, 0.05 mmol) and Na2CO3 (106 mg, 1.0 mmol) in DMF (2.5 mL) was stirred at 50 for 3-24 h under an oxygen balloon. The mixture was then diluted with ethyl acetate (20 mL), and washed with aqueous NaCl solution (3 X 10 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and subjected to flash chromatography (ca. 5 g of SiO2). Elution with hexanes/EtOAc afforded stilbene.

Reference： [1]Uzura, Saori; Sekine-Suzuki, Emiko; Nakanishi, Ikuo; Sonoda, Motohiro; Tanimori, Shinji [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3886 - 3891]

49
[ 1158680-88-6 ]
[ 192182-54-0 ]
C₂₀H₂₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 4h;Inert atmosphere; Reflux;	In a dry 250mL round-bottomed flask at room temperature were added sequentially compound 2 (8.90g, 31.7mmol), 3 (5.77g, 31.7mmol), Pd (PPh3) 4 (3.66g, 3.17mmol), K2CO3 (8.75g, 63.4 mmol), 1,4- dioxane (60.0mL) and water (15.0mL), stirring until evenly dispersed in the system. Under nitrogen, was heated under reflux for 4.0h. The reaction was cooled to room temperature, the solvent was spin-dry the crude product by column chromatography (ethyl acetate: petroleum ether = 1:10) to obtain compound 4 (8.10g, 76%).

Reference： [1]Patent: CN105524048,2016,A .Location in patent: Paragraph 0228; 0229

50
[ 190273-89-3 ]
[ 192182-54-0 ]
C₁₆H₁₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.1%	With palladium on activated charcoal; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; for 3h;Inert atmosphere;	2.00 g (8.9 mmol) of compound V,(13.4 mmol) of 3,5-dimethoxybenzeneboronic acid,Palladium on carbon (475 mg, 0.45 mmol)And 2.47 g (17.9 mmol) of potassium carbonateIn a 250 mL round bottom flask,Using 60 mL of ethylene glycol dimethyl etherAnd 10 mL of water as a solvent,The reaction was heated to 80 C for 3 hours under a nitrogen atmosphere.The reaction solution was filtered through celite,The filtrate was concentrated to give the crude product.Then add as little as possible to dissolve the hot ethyl acetate,Then quickly add a large number of cold ether and rapid cooling,Precipitation of a large number of light yellow solid,Filtered and washed to give compound VI as a yellow solid (2.01 g)Yield 80.1%

Reference： [1]Patent: CN105669566,2016,A .Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047

51
[ 192182-54-0 ]
[ 415718-60-4 ]
2-(4-amidinophenyl)-5-(3,5-dimethoxyphenyl)thiophene hydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 126,p. 789 - 798

52
[ 192182-54-0 ]
[ 415718-60-4 ]
2-(4-cyanophenyl)-5-(3,5-dimethoxyphenyl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In methanol; water; toluene; at 80℃; for 16.0h;	General procedure: To a stirred solution of the appropriate bromobenzonitrile (5 mmol), and tetrakis(triphenyl-phosphine) palladium (150 mg) intoluene (10 mL) was added 5 mL of a 1.5 M aqueous solution ofNaHCO3 followed by phenylboronic acid derivative (6 mmol) in5 mL of methanol. The vigorously stirred reaction mixture waswarmed to 80 C for 16 h. The solvent was then evaporated todryness, and the solid residue was partitioned between methylenechloride (250 mL) and an aqueous solution containing 5 mLconcentrated ammonia. The target diarylthiophene carbonitrileswere obtained from the methylene chloride layer upon evaporationto dryness under vacuum

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 126,p. 789 - 798

53
[ 52133-67-2 ]
[ 192182-54-0 ]
ethyl 2-(3,5-dimethoxyphenyl)-1H-pyrrole-3-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2214 - 2217

54
[ 446-09-3 ]
[ 192182-54-0 ]
C₁₄H₁₂FNO₄ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 1865 - 1869

55
[ 349-03-1 ]
[ 192182-54-0 ]
C₁₅H₁₂F₃NO₄ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 1865 - 1869

56
[ 19064-67-6 ]
[ 192182-54-0 ]
6-chloro-2-(3,5-dimethoxyphenyl)pyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With pyridine; copper diacetate; In dichloromethane; at 20℃; for 60h;	A solution of 6-chloropyridazin-3(2H)-one (506.5 mg, 3.880 mmol) in DCM (38 mL) was treated with 3,5-dimethoxyphenylboronic acid (776.8 mg, 4.268 mmol), Cu(OAc)2 (1410 mg, 7.760 mmol), and pyridine (627.7 tL, 7.760 mmol). The resulting mixture was stirred open to the atmosphere for 60 h at ambient temperature. The reaction mixture was filtered, and the filtrate was concentrated under vacuum. The resulting crude residue was purified by silica chromatography (5-60% DCM/ EtOAc as the gradient eluent) to afford the title compound (560 mg, 54% yield). MS (apci) m/z = 269.0 [(M+H)+2], 267.0 (M+H), with Cl pattern.

Reference： [1]Patent: WO2017/70708,2017,A1 .Location in patent: Paragraph 00511; 00512; 00513; 00514

57
[ 1834-27-1 ]
[ 192182-54-0 ]
6-chloro-2-(3,5-dimethoxyphenyl)-4-methylpyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; pyridine N-oxide; copper diacetate; In dichloromethane; at 20℃;	A solution of 6-chloro-4-methylpyridazin-3-ol (Intermediate X17; 500 mg, 3.46mmol) in DCM (20.3 mL) and pyridine (1 mL, 3.46 mmol) was treated with (3,5-dimethoxyphenyl)boronic acid (1.26 g, 6.92 mmol), Cu(OAc)2 (1.26 g, 6.92 mmol), and pyridine 1-oxide (1 .32 g, 13.8 mmol). The resulting mixture was stirred open to the atmosphere overnight at ambient temperature. The reaction mixture was diluted with DCM (100 mL) and filtered. The filtrate was washed with water (2 x 30 mL), and the organics were dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The crude residue was precipitated from MeOH to cleanly afford the title compound (780 mg, 80%). MS (apci) m/z = 281.1 (M+H), 283.0 [(M+H)+2] (with Cl pattern).

Reference： [1]Patent: WO2017/70708,2017,A1 .Location in patent: Paragraph 00553; 00554; 00555; 00556

58
[ 25462-61-7 ]
[ 192182-54-0 ]
3,3’’,5,5’’-tetramethoxy-1,1’:4’,1’-terphenyl-2’,5’-diamine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 532 - 536

59
[ 2077-19-2 ]
[ 192182-54-0 ]
2-(3',5'-dimethoxy[1,1'-biphenyl]-4-yl)propan-2-ol [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3776 - 3779

60
[ 2077-19-2 ]
[ 192182-54-0 ]
6-(3,5-dimethoxyphenyl)-3,3-dimethylisobenzofuran-1(3H)-one [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3776 - 3779

61
[ 365427-30-1 ]
[ 192182-54-0 ]
4-(3,5-dimethoxyphenyl)-1-methyl-1H-indazole [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 3588 - 3597

62
[ 89978-52-9 ]
[ 192182-54-0 ]
ethyl 2-(3,5-dimethoxyphenyl)isonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); triethylamine; In toluene; at 110℃; for 20h;	In a 100 mL two-necked flask, 2.10 g of 2-bromo-4-carboxylatepyridine, 2.01 g of 3,5-dimethoxyphenylboronic acid, 4.86 g of potassium carbonate, and 0.66 g of tetrakis(triphenylphosphine)palladium, toluene were added. 60 mL, heated at 110 C for 20 hours. After cooling to room temperature, the solution was washed with water (3×60 mL). The organic layer was dried with anhydrous MgSO4, filtered and evaporated. Purification by column chromatography (eluent:Petroleum ether / ethyl acetate = 80:1) gave 1.47 g of a white product.The yield was 56%.

Reference： [1]Patent: CN109053815,2018,A .Location in patent: Paragraph 0067; 0068; 0069; 0070
[2],2020,vol. 8,p. 2467 - 2474

63
[ 5350-41-4 ]
[ 192182-54-0 ]
[ 52692-17-8 ]

Reference： [1]RSC Advances,2019,vol. 9,p. 5738 - 5741

64
[ 176967-80-9 ]
[ 192182-54-0 ]
5-(3,5-dimethoxyphenyl)-8-nitroquinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 1609 - 1625

65
[ 57531-37-0 ]
[ 192182-54-0 ]
2-chloro-1-(3,5-dimethoxyphenyl)-4-nitro-1H-imidazole [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 2134 - 2147

66
[ 55583-59-0 ]
[ 192182-54-0 ]
4,6-bis(3,5-dimethoxyphenyl)pyrimidine-2,5-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 20h;Inert atmosphere; Reflux;	In the reaction vessel, <strong>[55583-59-0]4,6-dichloropyrimidine-2,5-diamine</strong>(499 mg, 2.79 mmol), 3,5-dimethoxyphenylboronic acid (1.21 g, 6.66 mmol),Sodium carbonate (1.48 g, 14.0 mmol),And tetrakis (triphenylphosphine) palladium (0)Ethanol (7 mL) and distilled water (7 mL) are added to a solution of (323 mg, 0.279 mmol) in toluene (28 mL) at room temperature, and the reaction solution is stirred for 20 hours under heating and reflux conditions under an argon atmosphere. It cooled to room temperature. Add distilled water (8 ml) and stir.The separated aqueous layer was extracted three times with ethyl acetate (12 mL).Thereafter, the entire organic layer was combined, saturated aqueous sodium chloride solution (12 mL) was added thereto, the mixture was stirred and washed, anhydrous sodium sulfate was added to the separated organic layer for dehydration, and the filtrate after filtration was concentrated under reduced pressure. . The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Bis (3,5-dimethoxyphenyl) pyrimidin-2,5-diamine(0.769 g, 72% yield).

Reference： [1]Patent: JP2019/64981,2019,A .Location in patent: Paragraph 0089; 0090; 0091

67
[ 192182-54-0 ]
[ 1538605-06-9 ]

Reference： [1]Patent: US2019/209564,2019,A1
[2]Patent: CN110386921,2019,A

68
[ 619-58-9 ]
[ 192182-54-0 ]
[ 913647-91-3 ]

Yield	Reaction Conditions	Operation in experiment
23%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water for 6h; Inert atmosphere;

Reference： [1]Pollinger, Julius; Schierle, Simone; Gellrich, Leonie; Ohrndorf, Julia; Kaiser, Astrid; Heitel, Pascal; Chaikuad, Apirat; Knapp, Stefan; Merk, Daniel [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1346 - 1352]

69
[ 22918-01-0 ]
[ 156545-07-2 ]
[ 192182-54-0 ]
C₁₉H₁₅F₂NO₂ [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 8331 - 8337

70
[ 777899-57-7 ]
[ 192182-54-0 ]
methyl 2-(3,5-dimethoxyphenyl)-5-nitroisonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 110℃;Inert atmosphere;	3,5-dimethoxyphenylboronic acid (8.47 g, 46 mmol), tetrakis(triphenylphosphine)palladium (5 g, 4.6 mmol) and sodium carbonate (5 g, 16 mmol) were added to a solution of <strong>[777899-57-7]methyl 2-chloro-5-nitroisonicotinate</strong> (10.0 g, 46.0 mmol) in the mixture of dioxane (200 mL) and water (50 mL). After the addition was completed, the mixture was stirred under N2 at 110 C. until the reaction of the starting materials was completed. The reaction solution was concentrated and separated by column chromatography (eluent: CH2Cl2/PE 20:1) to obtain compound methyl-(3,5-dimethoxyphenyl)-5-nitroisonicotinate (6 g, yield: 41%). MS (ESI): m/z 318.9 [M+1]+.

Reference： [1]Patent: US2019/270742,2019,A1 .Location in patent: Paragraph 0164-0165

71
[ 40396-54-1 ]
[ 192182-54-0 ]
1-(3',5'-dimethoxy-[1,1'-biphenyl]-3-yl)-2-phenylethane-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	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]

72
[ 93683-65-9 ]
[ 192182-54-0 ]
6-(3,5-dimethoxyphenyl)-3-nitropyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 95℃;Inert atmosphere;	General procedure: Generalprocedure. A solution of 6-chloro-2-cyano-3-nitropyridine (1 equiv) in toluene or dioxane/water (see compound description) was degassed with argon and subsequently, the corresponding aryl boronic acid (1.2equiv), Pd(PPh3)4 (0.02 equiv) and K2CO3 (2 equiv) were added. The mixture was degassed a second time, filled with argon and stirred at 95 C overnight. After completion of the reaction as monitored by TLC,the volatiles were evaporated to dryness and the crude residue was diluted with EtOAc (20 mL) and washed with water (2×20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated invacuo. The resulting residue was purified by silica gel flash chromatography, yielding the corresponding 6-aryl-3-nitropyridine-2-carbonitrile. The following compounds were made according to this procedure.

Reference： [1]Bioorganic and medicinal chemistry,2020,vol. 28

73
[ 192182-54-0 ]
[ 25069-38-9 ]
4-(bis(3',5'-dimethoxy-[1,1'-biphenyl]-4-yl)amino)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336; potassium carbonate In tetrahydrofuran; water at 85℃; for 10h; Inert atmosphere;

Reference： [1]Abdellah, Islam M.; El-Shafei, Ahmed [RSC Advances, 2019, vol. 10, # 1, p. 610 - 619]

74
[ 765278-73-7 ]
[ 192182-54-0 ]
[ 2414570-37-7 ]

Yield	Reaction Conditions	Operation in experiment
49%	With palladium diacetate; potassium carbonate; catacxium A In 1,2-dimethoxyethane; water at 100℃; for 18h; Inert atmosphere; Sealed tube;

Reference： [1]Meek, Simon J.; Zanghi, Joseph M. [Angewandte Chemie - International Edition, 2020, vol. 59, # 22, p. 8451 - 8455][Angew. Chem., 2020, vol. 132, # 22, p. 8529 - 8533,5]

75
[ 87486-33-7 ]
[ 192182-54-0 ]
C₁₃H₁₃ClN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	2.2 Step 2: synthesis of compound BB-2 In a microwave tube, under nitrogen protection, compound BB-2-3 (0.2 g, 1.12 mmol, 1 eq) and compound BB-1-2 (213 mg, 1.17 mmol, 1.05 eq) are dissolved in a mixed solution of dioxane (1.5 mL) and water (1.5 mL), and added with tetrakistriphenylphosphorpalladium (65 mg, 55.86 µmol, 0.05 eq) and sodium carbonate (130 mg, 1.23 mmol, 1.1 eq), and the mixture is stirred in a microwave at 120°C for 30 minutes. The reaction solution is directly concentrated. The crude product is separated by column chromatography (petroleum ether : ethyl acetate = 1 : 0 to 0 : 1) (TLC detection, petroleum ether : ethyl acetate = 1 : 1) to obtain compound BB-2. MS (ESI) m/z: 279.0 [M+1]+. 1H NMR (400MHz, CHCl3) δ: 7.64 (d, 2H), 7.28 (s, 1H), 6.59 (t, 1H), 3.86 (s, 6H), 3.61 (s, 3H).

Reference： [1]Current Patent Assignee: ZHANGZHOU PIENTZEHUANG PHARMACEUTICAL CO., LTD. - EP3750880, 2020, A1 Location in patent: Paragraph 0081; 0083

76
[ 138642-47-4 ]
[ 192182-54-0 ]
2-(3’,5’-dimethoxyphenyl)-5-methoxybenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	1.2.4.Generalprocedure4:Synthesisofbiphenyl-2-carbonitrilesandbiphenyl-2-ylmethylaminoformic acid tert-butyl esters by Suzuki cross-coupling General procedure: Boronicacid7(1.5 equiv),2-bromobenzonitrile12orN-Boc-benzylamine13(1.0 equiv),Pd(PPh3)4 (0.050 equiv), and Na2CO3 (3.0 equiv) were dissolved in a mixture of H2O/DMF 1:1 (10 mL)4per mmol o-bromobenzonitrile or o-bromo-N-Boc-benzylamine under a N2 atmosphere. The resultingheterogeneous mixture was refluxed for 18 h, before it was diluted with H2O. The mixture was extractedwith EtOAc, the combined organic layers washed with brine, dried over MgSO4, and concentrated in vacuo.The crude product was purified by FCC.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 110℃; Inert atmosphere;

Reference： [1]Bracher, Franz; Jourjine, Ilya A. P.; Krauß, Jürgen; Zeisel, Lukas [Beilstein Journal of Organic Chemistry, 2021, vol. 17, p. 2668 - 2679]
[2]Ito, Mamoru; Takaki, Asahi; Okamura, Moeka; Kanyiva, Kyalo Stephen; Shibata, Takanori [European Journal of Organic Chemistry, 2021, vol. 2021, # 11, p. 1688 - 1692]

77
[ 60656-87-3 ]
[ 192182-54-0 ]
C₁₇H₁₉BO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With trifluoroacetic acid In chloroform at 20℃; for 24h; Inert atmosphere;
41%	With trifluoroacetic acid In chloroform at 20℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	17 Method One Into the Schlenk tube, add the stirring magnet, the above formula 1a (182mg, 1mmol), the above formula 4d (180mg, 1.2mmol),Under nitrogen protection, trichloromethane (10 mL) was added, and trifluoroacetic acid (297 μL, 4 mmol) was added under stirring, and then sealed and stirred at room temperature for 24 hours. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain the compound 5d (124 mg, 41%).

Reference： [1]Zhao, Jing; Chen, Jiuxi; Xu, Qing; Li, Huan [Organic Letters, 2021, vol. 23, # 6, p. 1986 - 1990]
[2]Current Patent Assignee: WENZHOU UNIVERSITY - CN112625056, 2021, A Location in patent: Paragraph 0117-0123

78
[ 600-22-6 ]
[ 192182-54-0 ]
methyl 1-hydroxy-4,6-dimethoxy-3-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With trifluoroacetic acid In chloroform at 20℃; for 72h; Inert atmosphere;
56%	With trifluoroacetic acid In chloroform at 20℃; for 72h; Schlenk technique; Inert atmosphere; Sealed tube;	42 Method One Into the Schlenk tube, add the stirring magnet and the compound 1a (182mg, 1mmol) of the above formula one by one,Under nitrogen protection, chloroform (10 mL) was added, and compound 6e (108 μL, 1.2 mmol) and trifluoroacetic acid (1500 μL, 20 mmol) of the above formula were sequentially added with stirring, then sealed and reacted with stirring at room temperature for 72 hours. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain the compound 7e (149 mg, 56%).

79
[ 434-45-7 ]
[ 192182-54-0 ]
4,6-dimethoxy-3-phenyl-3-(trifluoromethyl) benzo[c][1,2]oxaborol-1(3H)-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With trifluorormethanesulfonic acid In chloroform at 20℃; for 22h; Inert atmosphere;
92%	With trifluorormethanesulfonic acid In chloroform at 20℃; for 22h; Schlenk technique; Inert atmosphere; Sealed tube;	44 Example 44 Into the Schlenk tube, add the stirring magnet and the compound 1a (182mg, 1mmol) of the above formula one by one,Under nitrogen protection, chloroform (10 mL) was added, and 6 g (168 μL, 1.2 mmol) of the compound of the above formula and trifluoromethanesulfonic acid (106 μL, 1.2 mmol) were successively added under stirring, then sealed, and stirred at room temperature for 22 hours. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 7 g (312 mg, 92%) of the compound of formula.

80
[ 15206-55-0 ]
[ 192182-54-0 ]
methyl 1-hydroxy-4,6-dimethoxy-3-phenyl-1,3-dihydrobenzo[c][1,2]oxaborole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With trifluorormethanesulfonic acid In chloroform at 20℃; for 12h; Inert atmosphere;
86%	With trifluorormethanesulfonic acid In chloroform at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	45 Example 45 Into the Schlenk tube, add the stirring magnet and the compound 1a (182mg, 1mmol) of the above formula one by one,Under nitrogen protection, chloroform (10 mL) was added, and the compound of the above formula 6h (170 μL, 1.2 mmol) and trifluoromethanesulfonic acid (44 μL, 0.5 mmol) were sequentially added with stirring, then sealed, and stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain the compound of formula 7h (282 mg, 86%).

81
[ 40102-86-1 ]
[ 192182-54-0 ]
2-bromo-7-(3,5-dimethoxyphenyl)-9H-thioxanthen-9-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 23911 - 23916
Angew. Chem.,2021,vol. 133,p. 24105 - 24111

82
[ 52414-99-0 ]
[ 192182-54-0 ]
C₁₅H₁₅NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dichloro-ethane at 60℃; for 14h;

Reference： [1]Echavarren, Antonio M.; García-Morales, Cristina; Mayans, Joan Guillem; Montesinos-Magraner, Marc; Tan, Eric [Chemical Science, 2021, vol. 12, # 44, p. 14731 - 14739]

83
[ 1121545-24-1 ]
[ 192182-54-0 ]
1-(3,4-dimethoxyphenyl)-8-phenylnaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.4%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; potassium carbonate In water; toluene at 90℃; for 48h; Inert atmosphere;

Reference： [1]Hu, Renjian; Li, Ruoxin; Lin, Shiyun; Shuai, Zhigang; Wang, Mengshi; Wei, Yen [Chemistry - A European Journal, 2022, vol. 28, # 3]

84
[ 98192-14-4 ]
[ 192182-54-0 ]
3',5'-dimethoxy-N-methyl-[1,1'-biphenyl]-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; water monomer; toluene at 120℃; for 0.5h; Microwave irradiation; Inert atmosphere; Sealed tube;

Reference： [1]Grøtli, Morten; Liljenberg, Sara; Matic, Josipa; Nain-Perez, Amalyn; Nilsson, Oscar [New Journal of Chemistry, 2022, vol. 46, # 12, p. 5593 - 5605]

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 192182-54-0 ]

Organoboron

[ 10365-98-7 ]

3-Methoxyphenylboronic acid

Similarity: 0.98

[ 5720-07-0 ]

4-Methoxyphenylboronic acid

Similarity: 0.96

[ 122775-35-3 ]

3,4-Dimethoxyphenylboronic acid

Similarity: 0.94

[ 182344-21-4 ]

(4-Hydroxy-3-methoxyphenyl)boronic acid

Similarity: 0.94

[ 90555-66-1 ]

3-Ethoxyphenylboronic acid

Similarity: 0.94

Aryls

[ 10365-98-7 ]

3-Methoxyphenylboronic acid

Similarity: 0.98

[ 5720-07-0 ]

4-Methoxyphenylboronic acid

Similarity: 0.96

[ 122775-35-3 ]

3,4-Dimethoxyphenylboronic acid

Similarity: 0.94

[ 182344-21-4 ]

(4-Hydroxy-3-methoxyphenyl)boronic acid

Similarity: 0.94

[ 90555-66-1 ]

3-Ethoxyphenylboronic acid

Similarity: 0.94

Ethers

[ 10365-98-7 ]

3-Methoxyphenylboronic acid

Similarity: 0.98

[ 5720-07-0 ]

4-Methoxyphenylboronic acid

Similarity: 0.96

[ 122775-35-3 ]

3,4-Dimethoxyphenylboronic acid

Similarity: 0.94

[ 182344-21-4 ]

(4-Hydroxy-3-methoxyphenyl)boronic acid

Similarity: 0.94

[ 90555-66-1 ]

3-Ethoxyphenylboronic acid

Similarity: 0.94

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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

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. 192182-54-0 ] {[proInfo.proName]}

Quality Control of [ 192182-54-0 ]

Related Doc. of [ 192182-54-0 ]

Product Details of [ 192182-54-0 ]

Calculated chemistry of [ 192182-54-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 192182-54-0 ]

Application In Synthesis of [ 192182-54-0 ]

[ 192182-54-0 ] Synthesis Path-Upstream 1~17

[ 192182-54-0 ] Synthesis Path-Downstream 1~84

Related Functional Groups of [ 192182-54-0 ]

Organoboron

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 192182-54-0 ]