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Quality Control of [ 20469-65-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 20469-65-2 ]

SDS Specification

Alternatived Products of [ 20469-65-2 ]

Product Citations

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su JOC,2020,85(16):10966-10972. DOI: 10.1021/acs.joc.0c01065 PubMed ID: 32806093

Abstract: In this study, we developed a simple

Purchased from AmBeed: class="">20469-65-2 ; class="">13675-18-8 ; class="">2564-83-2 ; class="">872-31-1 ; class="">192863-35-7 ; class="">871231-46-8 ; class="">192863-36-8 ; class="">6793-92-6 ; class="">3972-65-4 ; class="">2398-37-0 ; class="">850623-47-1 ; class="">705254-31-5 ; class="">580-13-2 ; class="">2635-13-4 ; class="span_more span_less">623-12-1 ; class="span_more span_less">1015082-71-9 ; class="span_more span_less">52415-29-9 ; class="span_more span_less">23145-07-5 ; class="span_more span_less">619-42-1 ; class="span_more span_less">99-90-1 ; class="span_more span_less">192863-37-9 ; class="span_more span_less">578-57-4 ; class="span_more span_less">407-14-7 ; class="span_more span_less">216434-82-1 ; class="span_more span_less">668984-08-5 ; class="span_more span_less">423118-47-2 ; class="span_more span_less">108-85-0 ; class="span_more span_less">252726-24-2 ; class="span_more span_less">101-55-3 ; class="span_more span_less">850623-36-8 ; class="span_more span_less">4923-87-9 ; class="span_more span_less">1394827-04-3 ; class="span_more span_less">850623-42-6 ; class="span_more span_less">438553-44-7 ; class="span_more span_less">460-00-4 ; class="span_more span_less">1187951-62-7 ; class="span_more span_less">705254-34-8 ; class="span_more span_less">111-83-1 ; class="span_more span_less">929626-22-2 ; class="span_more span_less">111-83-1 ; class="span_more span_less">906007-40-7 ; class="span_more span_less">1443282-44-7 ; class="span_more span_less">1000160-76-8 ; class="span_more span_less">1111733-01-7 ; class="span_more span_less">99-90-1 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Product Details of [ 20469-65-2 ]

CAS No. :	20469-65-2	MDL No. :	MFCD06200685
Formula :	C₈H₉BrO₂	Boiling Point :	-
Linear Structure Formula :	C₆H₃Br(OCH₃)₂	InChI Key :	KRWRFIMBWRVMKE-UHFFFAOYSA-N
M.W :	217.06	Pubchem ID :	639187
Synonyms :	3,5-Dimethoxybromobenzene

Calculated chemistry of [ 20469-65-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.13
TPSA :	18.46 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.57
Log Po/w (XLOGP3) :	2.69
Log Po/w (WLOGP) :	2.47
Log Po/w (MLOGP) :	2.22
Log Po/w (SILICOS-IT) :	2.49
Consensus Log Po/w :	2.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.15
Solubility :	0.153 mg/ml ; 0.000705 mol/l
Class :	Soluble
Log S (Ali) :	-2.73
Solubility :	0.404 mg/ml ; 0.00186 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0668 mg/ml ; 0.000308 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 20469-65-2 ]

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 [ 20469-65-2 ]

* 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 [ 20469-65-2 ]
Downstream synthetic route of [ 20469-65-2 ]

[ 20469-65-2 ] Synthesis Path-Upstream 1~2

1
[ 57753-81-8 ]
[ 20469-65-2 ]
[ 944261-79-4 ]

Reference： [1] Green Chemistry, 2014, vol. 16, # 9, p. 4170 - 4178

2
[ 20469-65-2 ]
[ 1044870-39-4 ]

Reference： [1] Patent: CN108218798, 2018, A,

[ 20469-65-2 ] Synthesis Path-Downstream 1~10

1
[ 626-39-1 ]
[ 124-41-4 ]
[ 621-23-8 ]
[ 20469-65-2 ]
[ 74137-36-3 ]

Reference： [1]Organic Preparations and Procedures International,2003,vol. 35,p. 225 - 227

2
[ 109-72-8 ]
[ 20469-65-2 ]
[ 127842-54-0 ]
[ 757962-27-9 ]

Yield	Reaction Conditions	Operation in experiment
42%	In tetrahydrofuran; water;	4.6.2.34 3-(3,4-Bis-difluoromethoxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylonitrile (E and Z Isomers) n-Butyl lithium (2.5 M, 3.7 mL) was added to s stirred solution of 3,5-dimethoxy-bromobenzene (2.0 g, 9.2 mmol) in THF (15 mL) at -65 C. After stirring for 30 min, a solution of <strong>[127842-54-0]3,4-bis-difluoromethoxy-benzaldehyde</strong> (2.0 g, 8.4 mmol) in THF (15 mL) was added slowly. The resulting mixture was stirred at -65 C. for 6 h and then quenched with isopropanol (5 mL). Water (40 mL) was added and the mixture was extracted with ether (360 mL). The combined organic layers were washed with water (240 mL), brine (40 mL), and dried (MgSO4). Solvent was removed and the residue was purified by flash chromatography (Silica gel, Hexane:EtOAc 7:3) to afford (3,4-bis-difluoromethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanol (1.3 g, 42%): 1H NMR (CDCl3) delta 7.32 (m, 1H), 7.19 (m, 2H), 6.86-6.19 (m 5H), 5.69 (d, J=2 Hz, 1H), 3.76 (s, 6H), 2.47 (d, J=2 Hz, 1H).

Reference： [1]Patent: US2005/107339,2005,A1

3
[ 20469-65-2 ]
[ 98-80-6 ]
[ 64326-17-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90.0℃; for 4.0h;Inert atmosphere;	a) 3,5-Dimethoxy-1,1'-biphenyl I115 A suspension of <strong>[20469-65-2]1-bromo-3,5-dimethoxybenzene</strong> (5.0 g, 23.0 mmol), phenylboronic acid (2.8 g, 23.0 mmol), Pd(dppf)Cl2 (0.57 g, 0.69 mmol) and potassium carbonate (4.8 g, 34.6 mmol) in 1,4-dioxane (80 ml.) and water (20 ml.) was heated at 90 C under N2 for 4 h. The mixture was diluted with water, extracted with EtOAc and the combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Pet.ether/EtOAc = 500/1 to 200/1 to 100/1) to give the title compound (5.2 g, 100 %) as a white solid. LCMS-C: Rt 2.47 min; m/z 215.0 [M+H]+.
100%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90.0℃; for 4.0h;Inert atmosphere;	A suspension of <strong>[20469-65-2]1-bromo-3,5-dimethoxybenzene</strong> (5.0 g, 23.0 mmol), phenylboronic acid (2.8 g, 23.0 mmol), Pd(dppf)Cl2 (0.57 g, 0.69 mmol) and potassium carbonate (4.8 g, 34.6 mmol) in 1,4-dioxane (80 ml.) and water (20 ml.) was heated at 90 C under N2 for 4 h. The mixture was diluted with water, extracted with EtOAc and the combined organic extracts were dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether/EtOAc = 500/1 to 200/1 to 100/1) to give the title compound 3,5-dimethoxy-1,1'-biphenyl I22 (5.2 g, 100 %) as a white solid. LCMS-A (ES-API): Rt 2.47 min; m/z 215.0 [M+H]+.

Reference： [1]Patent: WO2019/243491,2019,A1 .Location in patent: Page/Page column 117
[2]Patent: WO2020/2587,2020,A1 .Location in patent: Page/Page column 65
[3]European Journal of Organic Chemistry,2012,p. 1504 - 1508
[4]RSC Advances,2016,vol. 6,p. 34866 - 34871
[5]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1075 - 1080
[6]RSC Advances,2019,vol. 9,p. 8239 - 8245
[7]Journal of Natural Products,2018,vol. 81,p. 1850 - 1859
[8]Chemical Communications,2016,vol. 52,p. 12976 - 12979
[9]Journal of Organic Chemistry,2019,vol. 84,p. 1580 - 1587
[10]Organic Process Research and Development,2012,vol. 16,p. 117 - 122
[11]Journal of Organometallic Chemistry,2018,vol. 868,p. 76 - 85

4
[ 20469-65-2 ]
[ 1569-16-0 ]
[ 1256347-51-9 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5359 - 5361

5
[ 20469-65-2 ]
[ 17924-92-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5271 - 5274

6
[ 57753-81-8 ]
[ 20469-65-2 ]
[ 944261-79-4 ]

Reference： [1]Green Chemistry,2014,vol. 16,p. 4170 - 4178

7
[ 20469-65-2 ]
[ 15861-23-1 ]
1-(3,5-dimethoxyphenyl)indoline-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Materials Chemistry A,2015,vol. 3,p. 17704 - 17712

8
[ 20469-65-2 ]
[ 3282-99-3 ]
C₅₀H₅₄N₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.8%	With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 100 - 108℃; for 8h;Inert atmosphere;	The reaction route is as follows:250 mL three neck flask was added 2.41 g (9.0 × 10 -3 mol)1,1-bis (4-aminophenyl) cyclohexane,8.84 g (0.041 mol) of 3,5-dimethoxybromobenzene,5.08 g (0.045 mol) potassium tert-butoxide,48.2 g toluene.Under nitrogen atmosphere, 0.331 g (3.6 x 10-4 mol) of Pd2 (dba) 3,0.210 g (7.2 × 10 -4 mol) (t-Bu) 3PH · BF 4,The temperature was raised to 100 C to 108 C and refluxed for 8 hours.Completed the reaction,Add 50g water twice,Dried over anhydrous sodium sulfate,Decompression solvent was brown viscous liquid.The above crude product was treated with THF,Ethyl acetate (mass ratio of 5: 5) recrystallization,5.6g white powder was obtained,Yield: 76.8%.

Reference： [1]Patent: CN106565507,2017,A .Location in patent: Paragraph 0072; 0073; 0074; 0075

9
[ 20469-65-2 ]
[ 34595-26-1 ]
(3,5-dimethoxyphenyl)(2-(piperidin-1-yl)phenyl)methanol [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 138 - 141

10
[ 20469-65-2 ]
[ 34595-26-1 ]
12,14-dimethoxy-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrido[1,2-a]azepine [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 138 - 141

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Nomenclature of Ethers ? Preparation of Alkylbenzene ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions of Ethers ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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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

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[ CAS No. 20469-65-2 ] {[proInfo.proName]}

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[ 20469-65-2 ] Synthesis Path-Upstream 1~2

[ 20469-65-2 ] Synthesis Path-Downstream 1~10

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Aryls

Bromides

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[ 20469-65-2 ]