[ CAS No. 696-62-8 ] {[proInfo.proName]}

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Quality Control of [ 696-62-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 696-62-8 ]

SDS Specification

Alternatived Products of [ 696-62-8 ]

Product Citations

Modular Synthesis of New Metalloid-Substituted Olefins from Diboryl (Silyl) Ethenes via Suzuki–Miyaura Reactions

Sokolnicki, Tomasz ; Stefanowska-K?tna, Kinga ; Czapik, Agnieszka , et al. Int. J. Mol. Sci.,2024,25(22):12208. DOI: 10.3390/ijms252212208

Abstract: A novel approach towards synthesizing new metalloid-substituted olefins has been accomplished by transforming (E)-1,2-diboryl-1-silylethenes through two consecutive Suzuki–Miyaura coupling reactions. This methodology provides an effective and selective way to obtain new, structurally different products, such as (E)-1-silyl-1-boryl-2-arylethens, (1E,3E)-1-silyl-1-boryl-2-alkenylethens, and (E)-1-silyl-1-aryl1-2-aryl2ethenes, which are difficult to synthesize through hydrometallation reactions and related processes. Due to the presence of reactive motifs (silyl group, Bpin moiety, and Csp2-H bond) in the structure of the final products, these molecules might be considered powerful building blocks in modern chemistry. With the aid of demetallation and cross-coupling reactions, they might be further functionalized into several invaluable chemicals, i.e., tetrasubstituted olefins (anti-cancer drugs, fluorescence materials), compounds with high π-conjugation, and polymers.

Keywords: (E)-1-silyl-1,2-diboryl-ethenes ; aryl iodides ; (E)-(2-iodovinyl)benzenes ; Suzuki–Miyaura cross-coupling ; substituted olefins ; building blocks

Purchased from AmBeed: 696-62-8

Product Details of [ 696-62-8 ]

CAS No. :	696-62-8	MDL No. :	MFCD00001056
Formula :	C₇H₇IO	Boiling Point :	-
Linear Structure Formula :	CH₃O(C₆H₄I)	InChI Key :	SYSZENVIJHPFNL-UHFFFAOYSA-N
M.W :	234.03	Pubchem ID :	69676
Synonyms :

Calculated chemistry of [ 696-62-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.65
TPSA :	9.23 ?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) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.26
Log Po/w (XLOGP3) :	2.95
Log Po/w (WLOGP) :	2.3
Log Po/w (MLOGP) :	2.72
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	2.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.58
Solubility :	0.062 mg/ml ; 0.000265 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.366 mg/ml ; 0.00156 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.48
Solubility :	0.0771 mg/ml ; 0.00033 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.0

Safety of [ 696-62-8 ]

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

Application In Synthesis of [ 696-62-8 ]

* 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 [ 696-62-8 ]
Downstream synthetic route of [ 696-62-8 ]

[ 696-62-8 ] Synthesis Path-Upstream 1~1

1
[ 547-63-7 ]
[ 696-62-8 ]
[ 6274-50-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With 2,2,6,6-tetramethylpiperidinyl-lithium In toluene at 20℃; for 0.25 h; Glovebox Stage #2: With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 20℃; Glovebox	General procedure: Inside the glovebox, lithium 2,2,6,6-tetramethylpiperidide (LiTMP, 70.7 mg, 0.48 mmol, 1.2 eq.) was dissolved in toluene (1.5 mL) and carbonyl compound (3, 0.48 mmol, 1.2 eq.) was added. After 15 min of stirring at ambient temperature a solution of Pd(I) iodo dimer (2, 3.5 mg, 0.004 mmol, 1 molpercent for aryl iodides; 17.4 mg, 0.02 mmol, 5 molpercent for aryl bromides) and aryl halide (4, X = I or Br, 0.4 mmol, 1.0 eq.) in toluene (0.5 mL) was added. After 4-18 h of further stirring at ambient temperature (reaction progress was monitored by GCMS), the crude was directly adsorbed onto silica (washing with diethyl ether) and purified by flash column chromatography.

Reference： [1] Synthesis (Germany), 2018, vol. 50, # 22, p. 4471 - 4475

[ 696-62-8 ] Synthesis Path-Downstream 1~10

1
[ 1001-26-9 ]
[ 696-62-8 ]
(Z)-3-Ethoxy-3-(4-methoxy-phenyl)-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Heterocycles,1988,vol. 27,p. 257 - 260

2
(3,5-Dimethylphenyl)(4'-methoxyphenyl)iodonium triflate [ No CAS ]
[ 696-62-8 ]
[ 461-97-2 ]
[ 22445-41-6 ]
[ 108-38-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 2043 - 2046

3
[ 5918-93-4 ]
[ 696-62-8 ]
[ 6794-72-5 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 7768 - 7769

4
[ 52522-41-5 ]
[ 696-62-8 ]
[ 13406-29-6 ]
[ 180891-58-1 ]

Reference： [1]Organometallics,1996,vol. 15,p. 3708 - 3716

5
[ 1271-03-0 ]
[ 696-62-8 ]
[ 13406-29-6 ]
[ 180891-58-1 ]

Reference： [1]Organometallics,1996,vol. 15,p. 3708 - 3716

6
[ 696-62-8 ]
[ 172732-52-4 ]
[ 3133-07-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2742 - 2745

7
[ 696-62-8 ]
[ 172732-52-4 ]
[ 125610-78-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2742 - 2745

8
[ 2622-63-1 ]
[ 696-62-8 ]
2-(4'-methoxybiphenyl-2-yl)-1-methyl-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; potassium carbonate; triphenylphosphine; In benzene; at 150℃; for 24h;Sealed tube;	General procedure: In a 30-mL sealed tube, <strong>[2622-63-1]1-methyl-2-phenylbenzimidazole</strong> (1, 0.25mmol), [RuCl2(p-cymene)]2 (0.0125 mmol), Ph3P (0.075 mmol),K2CO3 (0.50 mmol), and iodoarene (0.25 mmol) were combined inanhydrous benzene (2 mL) under air. The mixture was then stirredat 150 °C for 24 h. The mixture was cooled to r.t., diluted with EtOAc, and filtered through a small pad of Celite. The filtrate was concentrated in vacuo and purified by flash chromatography (silicagel, EtOAc?hexane) to give the analytically pure 2-(biphenyl-2-yl)benzimidazoles. 2-(4?-Methoxybiphenyl-2-yl)-1-methyl-1H-benzoimidazole (2a) Pale yellow oil; yield: 76 mg (96percent); Rf = 0.26 (hexane?acetone,3:1).1H NMR (400 MHz, CDCl3): delta = 7.85 (d, J = 7.8 Hz, 1 H, HAr), 7.71(d, J = 7.6 Hz, 1 H, HAr), 7.50?7.62 (m, 2 H, HAr), 7.47 (t, J = 7.3Hz, 1 H, HAr), 7.20?7.35 (m, 2 H, HAr), 7.17 (d, J = 7.6 Hz, 1 H,HAr), 7.13 (d, J = 8.8 Hz, 2 H, HAr), 6.73 (d, J = 8.8 Hz, 2 H, HAr),3.73 (s, 3 H, OMe), 3.02 (s, 3 H, NMe).13C NMR (100 Hz, CDCl3): delta = 158.8, 154.1, 143.1, 141.2, 135.5,132.5, 132.1, 130.3, 129.7 (2 CAr), 129.6, 128.7, 127.1, 122.3,122.0, 119.7, 114.0 (2 CAr), 109.5, 55.1 (OMe), 30.2 (NMe).HRMS (FAB): m/z [M + H]+ calcd for C21H19ON2: 315.1497; found: 315.1507.

Reference： [1]Synthesis,2014,vol. 46,p. 3185 - 3190

9
[ 2622-63-1 ]
[ 696-62-8 ]
2-(4'-methoxybiphenyl-2-yl)-1-methyl-1H-benzoimidazole [ No CAS ]
C₂₈H₂₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%; 20%	With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; mesitylenecarboxylic acid; potassium carbonate; In toluene; at 150℃; for 24h;Sealed tube;	General procedure: In a 30-mL sealed tube, <strong>[2622-63-1]1-methyl-2-phenylbenzimidazole</strong> (1, 0.25mmol), [RuCl2(p-cymene)]2 (0.0125 mmol), Ph3P (0.075 mmol),K2CO3 (0.50 mmol), and iodoarene (0.25 mmol) were combined inanhydrous benzene (2 mL) under air. The mixture was then stirredat 150 °C for 24 h. The mixture was cooled to r.t., diluted with EtOAc, and filtered through a small pad of Celite. The filtrate was concentrated in vacuo and purified by flash chromatography (silicagel, EtOAc?hexane) to give the analytically pure 2-(biphenyl-2-yl)benzimidazoles.

Reference： [1]Synthesis,2014,vol. 46,p. 3185 - 3190

10
[ 696-62-8 ]
[ 7499-66-3 ]
6-bromo-2-N,N-bis(4-methoxyphenyl)aminonaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; 1,10-Phenanthroline; sodium t-butanolate; In toluene; at 120℃; for 48h;Inert atmosphere;	The reaction equation is as follows: Paraiodoanisole (15 g, 0.064 mol) and 6-bromo-2-naphthylamine (3.3 g, 0.015 mol) were dissolved in 120 ml of anhydrous toluene.Add CuI (0.89 g, 4.67 mmol) rapidly under nitrogen atmosphere.1,10-phenanthroline (1.232 g, 6.83 mmol) and sodium tert-butoxide (7 g, 75 mmol) were heated to 120C.After about 48 hours of reaction, the toluene is concentrated and removed.Simultaneously added dichloromethane and distilled water extraction (the volume ratio of dichloromethane and distilled water is 1:1),The organic layer was dried over anhydrous magnesium sulfate.filter,After decompression, concentratePurification by column chromatography (column chromatography with petroleum ether and various volumes of petroleum ether and dichloromethane,The first developing agent was petroleum ether.Subsequent developing agents are petroleum ether and dichloromethane in different volume ratios.The volume of methylene chloride increases sequentially;Finally, develop the petroleum ether in the agent:Dichloromethane = 4:1 (v:v)),A pale yellow solid, Compound 1, was obtained.The yield is about 88% (5.8g);

Reference： [1]Organic electronics,2018,vol. 58,p. 139 - 144
[2]Patent: CN107954884,2018,A .Location in patent: Paragraph 0057; 0058; 0059

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? General Reactivity ? Halogenation of Phenols ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Nomenclature of Ethers ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? 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 ? Reimer-Tiemann Reaction ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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[ 696-62-8 ]

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[ 29415-97-2 ]

Methyl 3-bromo-4-hydroxybenzoate

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[ CAS No. 696-62-8 ] {[proInfo.proName]}

Quality Control of [ 696-62-8 ]

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Product Details of [ 696-62-8 ]

Calculated chemistry of [ 696-62-8 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 696-62-8 ]

Application In Synthesis of [ 696-62-8 ]

[ 696-62-8 ] Synthesis Path-Upstream 1~1

[ 696-62-8 ] Synthesis Path-Downstream 1~10

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