[ CAS No. 155826-85-0 ]

Name: 155826-85-0|2-(4-Methoxyphenyl)-1,3,2-dioxaborinane|98%
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Quality Control of [ 155826-85-0 ]

COA NMR CNMR HPLC LC-MS

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SDS

Alternatived Products of [ 155826-85-0 ]

Product Details of [ 155826-85-0 ]

CAS No. :	155826-85-0	MDL No. :
Formula :	C₁₀H₁₃BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	192.02 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 155826-85-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.91
TPSA :	27.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	0.83
Log Po/w (MLOGP) :	0.56
Log Po/w (SILICOS-IT) :	1.08
Consensus Log Po/w :	0.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.642 mg/ml ; 0.00334 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	1.19 mg/ml ; 0.00619 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.254 mg/ml ; 0.00132 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.61

Safety of [ 155826-85-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 155826-85-0 ]

* 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.

Downstream synthetic route of [ 155826-85-0 ]

[ 155826-85-0 ] Synthesis Path-Downstream 1~24

1
[ 155826-85-0 ]
[ 175791-65-8 ]
[ 175791-66-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	In N,N-dimethyl-formamide at 100℃;

Reference： [1]Sakamoto, Takao; Kondo, Yoshinori; Sato, Shuichiroh; Yamanaka, Hiroshi [Tetrahedron Letters, 1994, vol. 35, # 18, p. 2919 - 2920]

2
[ 1942-45-6 ]
[ 155826-85-0 ]
(E)-1-methoxy-4-(oct-4-en-4-yl)benzene [ No CAS ]
1-Methoxy-4-((1Z,3E)-1,2,3-tripropyl-hepta-1,3-dienyl)-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water In dibutyl ether at 80℃; for 5h; Title compound not separated from byproducts.;

Reference： [1]Shirakawa; Takahashi; Tsuchimoto; Kawakami [Chemical Communications, 2001, # 24, p. 2688 - 2689]

3
[ 513-81-5 ]
[ 155826-85-0 ]
[ 29143-06-4 ]
2,3-dimethyl-3-(4-methoxyphenyl)-1-butene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; butan-1-ol In 1,4-dioxane at 100℃; for 2h;

Reference： [1]Shirakawa, Eiji; Takahashi, Go; Tsuchimoto, Teruhisa; Kawakami, Yusuke [Chemical Communications, 2002, # 19, p. 2210 - 2211]

4
[ 155826-85-0 ]
[ 2132-80-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,3-bis-(diphenylphosphino)propane; oxygen In dimethyl sulfoxide at 80℃; for 26h;

Reference： [1]Yoshida, Hiroto; Yamaryo, Yasuhito; Ohshita, Joji; Kunai, Atsutaka [Tetrahedron Letters, 2003, vol. 44, # 8, p. 1541 - 1544]

5
[ 100-52-7 ]
[ 155826-85-0 ]
[ 720-44-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 4-Octyne; water In 1,4-dioxane at 80℃; for 12h;

Reference： [1]Takahashi, Go; Shirakawa, Eiji; Tsuchimoto, Teruhisa; Kawakami, Yusuke [Chemical Communications, 2005, # 11, p. 1459 - 1461]

6
[ 66-25-1 ]
[ 155826-85-0 ]
1-(4-methoxylphenyl)-1-hexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 4-Octyne; water In 1,4-dioxane at 80℃; for 12h;

Reference： [1]Takahashi, Go; Shirakawa, Eiji; Tsuchimoto, Teruhisa; Kawakami, Yusuke [Chemical Communications, 2005, # 11, p. 1459 - 1461]

7
[ 5720-07-0 ]
[ 504-63-2 ]
[ 155826-85-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	In dichloromethane at 20℃;
	With magnesium sulfate In diethyl ether at 20℃; for 9h;
	In dichloromethane at 20℃; Inert atmosphere;

	In dichloromethane at 20℃; Inert atmosphere;
	In dichloromethane at 20℃; for 16h; Sealed tube;
	In toluene at 80℃; Schlenk technique; Inert atmosphere;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]
[2]Takahashi, Go; Shirakawa, Eiji; Tsuchimoto, Teruhisa; Kawakami, Yusuke [Chemical Communications, 2005, # 11, p. 1459 - 1461]
[3]Oda, Susumu; Yamamoto, Hisashi [Angewandte Chemie - International Edition, 2013, vol. 52, # 31, p. 8165 - 8168][Angew. Chem., 2013, vol. 125, # 31, p. 8323 - 8326,4]
[4]Salim Lew, Tedrick Thomas; Wen Lim, Diane Shu; Zhang, Yugen [Green Chemistry, 2015, vol. 17, # 12, p. 5140 - 5143]
[5]Dimakos, Victoria; Liu, Jacklyn J. W.; Ge, Zhenlu; Taylor, Mark S. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 23, p. 5671 - 5674]
[6]Li, Gen; Qin, Ziyang; Radosevich, Alexander T. [Journal of the American Chemical Society, 2020, vol. 142, # 38, p. 16205 - 16210]

8
[ 1000-87-9 ]
[ 155826-85-0 ]
[ 57095-04-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With (γ-N,N-dimethylaminopropyl)diphenylphosphine In 1-methyl-pyrrolidin-2-one; water at 80℃; for 24h;

Reference： [1]Takahashi, Go; Shirakawa, Eiji; Tsuchimoto, Teruhisa; Kawakami, Yusuke [Advanced Synthesis and Catalysis, 2006, vol. 348, # 7-8, p. 837 - 840]

9
[ 821-74-9 ]
[ 155826-85-0 ]
(Z)-6-(4-methoxyphenyl)-4-nonene [ No CAS ]
(E)-6-(4-methoxyphenyl)-4-nonene [ No CAS ]
(Z)-5-(4-methoxyphenyl)-4-nonene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (γ-N,N-dimethylaminopropyl)diphenylphosphine In 1-methyl-pyrrolidin-2-one; water at 80℃; for 24h; Title compound not separated from byproducts;

Reference： [1]Takahashi, Go; Shirakawa, Eiji; Tsuchimoto, Teruhisa; Kawakami, Yusuke [Advanced Synthesis and Catalysis, 2006, vol. 348, # 7-8, p. 837 - 840]

10
[ 78-94-4 ]
[ 155826-85-0 ]
[ 104-20-1 ]

Yield	Reaction Conditions	Operation in experiment
41%	With water; diphenyl acetylene In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

11
[ 155826-85-0 ]
[ 70720-38-6 ]
[ 1388624-21-2 ]

Yield	Reaction Conditions	Operation in experiment
39%	With dodecacarbonyl-triangulo-triruthenium In 3,3-dimethyl-butan-2-one at 140℃; Inert atmosphere; regioselective reaction;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]

12
[ 155826-85-0 ]
[ 70720-38-6 ]
[ 1370412-41-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	With 3,3-dimethyl-butan-2-one; dodecacarbonyl-triangulo-triruthenium at 140℃; for 24h; Inert atmosphere;

Reference： [1]Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Journal of Organic Chemistry, 2013, vol. 78, # 2, p. 658 - 672]

13
[ 886501-07-1 ]
[ 155826-85-0 ]
[ 1416556-07-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	With 3,3-dimethyl-butan-2-one; dodecacarbonyl-triangulo-triruthenium at 140℃; for 24h; Inert atmosphere;

Reference： [1]Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Journal of Organic Chemistry, 2013, vol. 78, # 2, p. 658 - 672]

14
[ 155826-85-0 ]
2-(piperidin-1-yl)-3-trifluoromethylpyridine [ No CAS ]
[ 1431616-04-4 ]

Yield	Reaction Conditions	Operation in experiment
16%	With copper(ll) sulfate pentahydrate; dodecacarbonyl-triangulo-triruthenium; trimethyleneglycol In o-xylene at 135℃; for 36h; Inert atmosphere;

Reference： [1]Schwarz, Maria C.; Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 539 - 552]

15
[ 1481723-17-4 ]
[ 155826-85-0 ]
C₂₇H₅₄O₃Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: tris(triethylsilyl)silyl triflate With potassium hexamethylsilazane In toluene at -78℃; for 1h; Inert atmosphere; Stage #2: 4-methoxylphenylboronic acid 1,3-propanediol ester In toluene at -78 - 0℃; for 1h; Inert atmosphere;

Reference： [1]Oda, Susumu; Yamamoto, Hisashi [Angewandte Chemie - International Edition, 2013, vol. 52, # 31, p. 8165 - 8168][Angew. Chem., 2013, vol. 125, # 31, p. 8323 - 8326,4]

16
[ 155826-85-0 ]
[ 768392-43-4 ]
[ 1301717-33-8 ]
(R)-3-(4-methoxyphenyl)-3-phenyl-1-butene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88 % ee	Stage #1: 4-methoxylphenylboronic acid 1,3-propanediol ester With 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; sodium methylate; copper(l) chloride In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: (E)-diethyl (3-phenylbut-2-en-1-yl) phosphate In tetrahydrofuran at 30℃; for 40h; Overall yield = 90 %; enantioselective reaction;

Reference： [1]Takeda, Momotaro; Takatsu, Keishi; Shintani, Ryo; Hayashi, Tamio [Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2354 - 2367]

17
[ 155826-85-0 ]
[ 768392-43-4 ]
[ 1334512-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1-((1S,2S)-2-hydroxyindan-1-yl)-3-pentamethylphenylimidazolinium hexafluorophosphate; copper(l) chloride; sodium methylate / tetrahydrofuran / 0.08 h / 20 °C 1.2: 40 h / 30 °C 2.1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 - 20 °C 2.2: 1 h / 0 - 20 °C

Reference： [1]Takeda, Momotaro; Takatsu, Keishi; Shintani, Ryo; Hayashi, Tamio [Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2354 - 2367]

18
[ 14660-45-8 ]
[ 155826-85-0 ]
[ 100-09-4 ]

Yield	Reaction Conditions	Operation in experiment
95 %Spectr.	With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube;

Reference： [1]Duong, Hung A.; Nguyen, Tuan Minh; Rosman, Nurul Zubaidah Binte; Tan, Lionel Jia Liang [Synthesis, 2014, vol. 46, # 14, p. 1881 - 1885]

19
[ 155826-85-0 ]
[ 54132-75-1 ]
[ 127291-98-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere;

Reference： [1]Salim Lew, Tedrick Thomas; Wen Lim, Diane Shu; Zhang, Yugen [Green Chemistry, 2015, vol. 17, # 12, p. 5140 - 5143]

20
[ 120-92-3 ]
[ 155826-85-0 ]
[ 1671-76-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With 3-methylpyridin-2-ylamine; chlorobis(ethylene)rhodium(I) dimer; ethyl crotonate; 1,3-bis(2,4,6-trimethylphenyl)4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene; water; toluene-4-sulfonic acid In 2-methyltetrahydrofuran at 150℃; for 120h; Inert atmosphere; Glovebox; Sealed tube;

Reference： [1]Xia, Ying; Wang, Jianchun; Dong, Guangbin [Journal of the American Chemical Society, 2018, vol. 140, # 16, p. 5347 - 5351]

21
2,3,4,6-tetra-O-benzyl-D-mannopyranose [ No CAS ]
[ 155826-85-0 ]
4-methoxyphenyl-2,3,4,6-tetra-O-benzyl-D-mannopyranoside [ No CAS ]
[ 173597-19-8 ]

Yield	Reaction Conditions	Operation in experiment
77.778 % de	With copper diacetate; triethylamine In acetonitrile at 40℃; Sealed tube; Overall yield = 52 %; stereoselective reaction;

Reference： [1]Dimakos, Victoria; Liu, Jacklyn J. W.; Ge, Zhenlu; Taylor, Mark S. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 23, p. 5671 - 5674]

22
7-bromo-2-hydroxy-9-methyl-2-(trifluoromethyl)-1,2-dihydro-3H-pyrrolo[1,2-α]indol-3-one [ No CAS ]
[ 155826-85-0 ]
2-hydroxy-7-(4-methoxyphenyl)-9-methyl-2-(trifluoromethyl)-1,2-dihydro-3H-pyrrolo[1,2-α]indol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 80℃;

Reference： [1]Wang, Le; Wang, Le; Zhou, Jia; Chen, Han-Qia; Li, Dong-Li; Lin, Jun-Bing; Lin, Jun-Bing; Li, Ke; Ding, Tong-Mei; Zhang, Shu-Yu; Zhang, Shu-Yu [Organic Letters, 2020, vol. 22, # 12, p. 4716 - 4720]

23
[ 75-52-5 ]
[ 155826-85-0 ]
[ 5961-59-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane at 120℃; for 36h; Schlenk technique; Inert atmosphere; chemoselective reaction;

Reference： [1]Li, Gen; Qin, Ziyang; Radosevich, Alexander T. [Journal of the American Chemical Society, 2020, vol. 142, # 38, p. 16205 - 16210]

24
[ 624-31-7 ]
[ 155826-85-0 ]
[ 53040-92-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate In 1,4-dioxane at 115℃; for 30h; Inert atmosphere;

Reference： [1]Sen, Abhijit; Dhital, Raghu N.; Sato, Takuma; Ohno, Aya; Yamada, Yoichi M.A. [ACS Catalysis, 2020, vol. 10, # 24, p. 14410 - 14418]

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P234	Keep only in original container.
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Physical hazards
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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. 155826-85-0 ]

Quality Control of [ 155826-85-0 ]

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Product Details of [ 155826-85-0 ]

Calculated chemistry of of [ 155826-85-0 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 155826-85-0 ]

[ 155826-85-0 ] Synthesis Path-Downstream 1~24

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