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[ CAS No. 5572-94-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 5572-94-1
Chemical Structure| 5572-94-1
Structure of 5572-94-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 5572-94-1 ]

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Alternatived Products of [ 5572-94-1 ]

Product Details of [ 5572-94-1 ]

CAS No. :5572-94-1 MDL No. :MFCD26394871
Formula : C11H14BIO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JKKCLZFCRZKJEG-UHFFFAOYSA-N
M.W : 315.94 Pubchem ID :68755227
Synonyms :

Calculated chemistry of [ 5572-94-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 70.49
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.51
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.24
Solubility : 0.0182 mg/ml ; 0.0000575 mol/l
Class : Moderately soluble
Log S (Ali) : -3.58
Solubility : 0.0829 mg/ml ; 0.000262 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.44
Solubility : 0.0114 mg/ml ; 0.0000361 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.14

Safety of [ 5572-94-1 ]

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 [ 5572-94-1 ]

* 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 [ 5572-94-1 ]

[ 5572-94-1 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 5122-99-6 ]
  • [ 126-30-7 ]
  • [ 5572-94-1 ]
YieldReaction ConditionsOperation in experiment
86% With magnesium sulfate; In dichloromethane; at 20℃;Product distribution / selectivity; Method 3; 4-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzaldehyde; A. 2-(4-iodophenyl)-5,5-dimethyl-l ,3,2-dioxaborinane; 2-(4-iodophenyl)-5,5-dimethyl-l,3,2-dioxaborinane was prepared following the method described in Method 2 step A to yield 5.4 g (86% yield) of the title compound as an off-white solid.LC-MS: [M+H]+ 316.12 Mass: calculated for C11H14BIO2, 315.95
In diethyl ether; at 20℃;Inert atmosphere; Molecular sieve; General procedure: To a Et2O solution of anorganoboronic acid (1.00 equiv) and 2,2-dimethylpropane-1,3-diol (neopentyl glycol)(1.02 equiv), 4A molecular sieves was added and the reaction mixture was stirred atroom temperature. After the reaction finished, the reaction mixture was filtered andconcentrated in vacuo. The residue was subjected to flash column chromatography(eluent: petroleum ether/ethyl acetate) or recrystallization to obtain the desired product
  • 2
  • [ 624-38-4 ]
  • [ 5572-94-1 ]
  • 4
  • [ 5572-94-1 ]
  • [ 63697-96-1 ]
  • [ 1244016-74-7 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen; triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In acetonitrile; at 20 - 75℃;Inert atmosphere;Product distribution / selectivity; Method 4; 4-(4-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzyl) morpholine; A. 4-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzaldehyde; 4-((4-(5,5-Dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzaldehyde was prepared following the method described in Method 3 steps A-C to yield 50.O g (99% yield) of the title compound as a yellow solid. LC-MS: [M+H]+ 319.0 1H NMR (400 MHz, CDCl3) δ: ppm 10.02 (s, IH), 7.95 (d, 2H), 7.79 (m, 4H), 7.66 (d, 2H), 3.78 (s, 4H), 1.00 (s, 6H).
  • 5
  • [ 940911-03-5 ]
  • [ 5572-94-1 ]
  • [ 1244016-81-6 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In acetonitrile; at 20 - 85℃;Inert atmosphere; C . 5 - { [4-(5 ,5 -Dimethyl- 1 ,3 ,2-dioxaborinan-2-yl)phenyl] ethynyl} pyridine -2- carbaldehyde; To an argon purged solution of 2-(4-iodophenyl)-5,5-dimethyl-l,3,2- dioxaborinane (Method 3, step A) (15 g, 48 mmol) in acetonitrile was addedPdCl2(PPh3)2 (0.7 g, 9.5 mmol) and CuI (0.09 g, 4.7 mmol) at room temperature. The resulting solution was stirred under argon for 10 min. Triethylamine (20 mL, 142 mmol) followed by 5-[(trimethylsilyl)ethynyl]pyridine-2-carbaldehyde (8.1 g, 62mmol) were added and the reaction mixture was then stirred at 85 0C for 2 h. The reaction mixture was concentrated under reduced pressure and then ice-cold water was added. The precipitated solid was stirred as a suspension and was then filtered and washed with water followed by pet-ether to provide 5-[4-(5,5-dimethyl-l,3,2-dioxaborinan-2- yl)phenyl]ethynyl}pyridine-2-carbaldehyde (15 g, 99%) as brown solid. LC-MS: [M+H]+ 3201H NMR (400 MHz, CDCl3) delta: ppm 10.08 (s, IH), 8.89 (s, IH), 7.95 (m, 2H), 7.82 (d, 2H), 7.55 (d, 2H), 3.78 (s, 4H), 1.03 (s, 6H).
  • 6
  • [ 2510-23-8 ]
  • [ 5572-94-1 ]
  • [ 1244016-73-6 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 60℃; for 2h;Inert atmosphere; B. 3-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)pyridine; In an oven dried round bottom flask, a solution of <strong>[5572-94-1]2-(4-iodophenyl)-5,5-dimethyl-1,3,2-dioxaborinane</strong> (21 g, 66.47 mmol) and triethylamine (27.8 mL, 199.40 mmol) in acetonitrile (305 mL) was degassed with a stream of N2 for 5 minutes. After this time, 3- ethynylpyridine (7.20 g, 69.79 mmol), Pd(PPh3)2Cl2 (3.5 g, 4.99 mmol) and copper(I) iodide (0.633 g, 3.32 mmol) were added. The flask was then placed in a 60 0C oil bath and was stirred for 2 h, until TLC indicated formation of a new product. The reaction was allowed to cool to room temperature and was then concentrated in vacuo. The resulting brown solid was dissolved in DCM and then impregnated on silica gel. The crude material was purified by silica gel chromatography (5-50% Ethyl Acetate in Hexanes) to afford the desired product as a yellow solid (16.2 g, 83%). 1U NMR (300 MHz, DMSO-d6) δ: ppm 8.77 (s, IH); 8.61 (d, IH); 7.98 (d, IH); 7.76 (d, 2H); 7.58 (d, 2H); 7.48 (dd, IH), 3.78 (s, 4H); 0.97 (s, 6H).
  • 7
  • [ 5572-94-1 ]
  • [ 75748-09-3 ]
  • C22H30BIO4Si [ No CAS ]
  • 8
  • [ 5509-08-0 ]
  • [ 5572-94-1 ]
  • [ 134321-77-0 ]
  • 9
  • [ 5572-94-1 ]
  • [ 71042-21-2 ]
  • [ 1308658-21-0 ]
  • 10
  • [ 5572-94-1 ]
  • [ 7051-34-5 ]
  • [ 1308658-12-9 ]
  • 11
  • [ 5765-65-1 ]
  • [ 5572-94-1 ]
  • [ 87350-77-4 ]
  • 12
  • [ 5542-49-4 ]
  • [ 5572-94-1 ]
  • [ 55376-34-6 ]
  • 13
  • [ 61582-64-7 ]
  • [ 5572-94-1 ]
  • [ 57702-49-5 ]
  • 14
  • N-(benzoyloxy)-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
  • [ 5572-94-1 ]
  • 2-(4-iodophenyl)-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
  • 15
  • [ 52742-32-2 ]
  • [ 5572-94-1 ]
  • [ 76464-91-0 ]
  • 16
  • [ 92197-18-7 ]
  • [ 5572-94-1 ]
  • 4-iodo-N,N-diisopropylaniline [ No CAS ]
  • 17
  • [ 5572-94-1 ]
  • [ 18414-58-9 ]
  • [ 62729-39-9 ]
  • 18
  • [ 1131-33-5 ]
  • [ 5572-94-1 ]
  • [ 1590366-84-9 ]
  • 19
  • (phen)CuCF<SUB>2</SUB>CF<SUB>2</SUB>Ph [ No CAS ]
  • [ 5572-94-1 ]
  • 2-(4-(1,1,2,2-tetrafluoro-2-phenylethyl))-5,5-dimethyl-1,3,2-dioxaborinane [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In tetrahydrofuran; tetrahydrofuran-d8; at 60℃; for 6h;Inert atmosphere; General procedure: The title compound was prepared by method A as described below. (phen)CuCF2CF2Ph (8.4 mg, 0.02 mmol) and 2-(4-iodophenyl)-5,5-dimethyl-1 ,3,2-dioxaborinane (7.6 mg,0.024 mmol) were mixed in 0.5 ml of THF/THF-d8 (v/v’=4/i)solvent under a nitrogen atmosphere and heated at 60 C. for6 hours, thereby giving the corresponding title compound at ayield of 72% (calculated from ‘9F NMR). ‘9F NMR (376 MHz, in THF/THF-d8, it, ö/ppm):-114.6 (s, 2F), -114.4 (s, 2F). HRMS Calcd for C,9H,9F402B 366.1414. found mlz 366.1412.
  • 20
  • [ 51339-03-8 ]
  • [ 5572-94-1 ]
  • [ 40686-52-0 ]
  • 21
  • [ 941-98-0 ]
  • [ 5572-94-1 ]
  • 1-(2-(4-iodophenyl)naphthalene-1-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris(triphenylphosphine)ruthenium(II) chloride; caesium carbonate; at 150℃; for 3h;Inert atmosphere; Under an argon atmosphere, carbonylchloro hydride tris (triphenylphosphine)ruthenium 4.8 mg (5.0μmol), 2-(4- iodophenyl) -5,5 - dimethyl -1, 3, 2 - dioxaborinane 316 mg (1.00mmol), cesium carbonate 97.8mg (300μmol) and 1 - acetonaphthone 1.12 mg (6.58 mmol) are added in a reactioncontainer. The reactionvessel is heated on 135 ,and it is stirred for 12 hour. After thereaction vessel cooled as room temperature,mixture is purified by using silica gel columnchromatography (hexane : ethyl acetate = 10 : 0-9 : 1), 260 mg of 1 - [2 - (4- iodophenyl) naphthalene - 1- yl] ethanone obtained (white solid, yield 70%).
  • 22
  • [ 5572-94-1 ]
  • C22H23NO4 [ No CAS ]
  • C28H28INO4 [ No CAS ]
  • 23
  • [ 5572-94-1 ]
  • C22H23NO4 [ No CAS ]
  • C22H16INO [ No CAS ]
  • 24
  • [ 2040-04-2 ]
  • [ 5572-94-1 ]
  • C15H13IO2 [ No CAS ]
  • 25
  • [ 1316859-98-9 ]
  • [ 5572-94-1 ]
  • C13H10INO2 [ No CAS ]
  • 26
  • [ 930-22-3 ]
  • [ 5572-94-1 ]
  • C10H11IO [ No CAS ]
  • 27
  • [ 930-22-3 ]
  • [ 5572-94-1 ]
  • [ 141-78-6 ]
  • C12H13IO2 [ No CAS ]
  • 29
  • [ 798553-21-6 ]
  • [ 5572-94-1 ]
  • 4'-iodo-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); [bis(acetoxy)iodo]benzene; silver(I) 4-methylbenzenesulfonate; In 1,1,2-trichloroethane; at 110℃; for 1h;Sealed tube; Gold catalyst 1a (8.9 mg, 0.01 mmol), AgOTs (11.2 mg, 0.02 mmol), PhI(OAc) 2 (84 mg, 0.26 mmol) and C2H3Cl3 (1 ml) were added to the dried tube and stirred vigorously at room temperature. 30min. Subsequently, a mixed solution of (59.7 mg, 0.2 mmol) and (82.15 mg, 0.26 mmol) of C2H3Cl3 (1 ml) was dropped into a sealed tube and reacted at 110 C for 1 h. The reaction solution was concentrated, dried, and purified by column chromatography to give the product 71.9mg ( petroleum ether: ethyl acetate=100:1), yield 84%
84% With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); [bis(acetoxy)iodo]benzene; silver(I) 4-methylbenzenesulfonate; In 1,1,2-trichloroethane; at 110℃; for 1h;Schlenk technique; Inert atmosphere; General procedure: To a dried Schlenk tube was added 1f (8.9 mg, 0.01 mmol), AgOTs (11.2 mg, 0.04mmol), PhI(OAc)2 (84.0 mg, 0.26 mmol) and anhydrous TCE (1,1,2-trichloroethane, 1mL) at room temperature under an argon atmosphere. After vigorously stirring for 30min at room temperature, 2 (0.20 mmol) and 3 (0.26 mmol) in 1 mL anhydrous TCEwas added under an argon atmosphere, and then the reaction mixture was stirred at 110oC for 1-2 h. The reaction mixture was concentrated under reduced pressure and theresulting residue was purified by flash chromatography on silica gel (petroleumether/ethyl acetate) to give desired coupling product 4.
  • 30
  • [ 5572-94-1 ]
  • 3-(trimethylsilyl)phenyl methanesulfonate [ No CAS ]
  • 4'-iodo-[1,1'-biphenyl]-3-yl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); [bis(acetoxy)iodo]benzene; silver(I) 4-methylbenzenesulfonate; In 1,1,2-trichloroethane; at 110℃; for 2h;Schlenk technique; Inert atmosphere; General procedure: To a dried Schlenk tube was added 1f (8.9 mg, 0.01 mmol), AgOTs (11.2 mg, 0.04mmol), PhI(OAc)2 (84.0 mg, 0.26 mmol) and anhydrous TCE (1,1,2-trichloroethane, 1mL) at room temperature under an argon atmosphere. After vigorously stirring for 30min at room temperature, 2 (0.20 mmol) and 3 (0.26 mmol) in 1 mL anhydrous TCEwas added under an argon atmosphere, and then the reaction mixture was stirred at 110oC for 1-2 h. The reaction mixture was concentrated under reduced pressure and theresulting residue was purified by flash chromatography on silica gel (petroleumether/ethyl acetate) to give desired coupling product 4.
  • 31
  • [ 24424-99-5 ]
  • [ 5572-94-1 ]
  • [ 74-88-4 ]
  • [ 619-44-3 ]
YieldReaction ConditionsOperation in experiment
92% General procedure: A 15 mL Schlenk tube equipped with a stirrer bar was chargedwith CuCl (10 mol%), L7 (13 mol%), LiOMe (2.5 equiv), and theappropriate boronic ester 1 or 4 (0.375 mmol). The vessel wasthen evacuated and filled with Ar (three cycles). DMA (0.5 mL)and (Boc)2O (0.25 mmol) were added sequentially under Ar, andthe mixture was stirred at 30 for 6 h. MeI (5 equiv) was thenadded in air, and the mixture was stirred at 30 for additional2 h. The mixture was finally diluted with EtOAc and washedwith sat. aq NaCl (20 mL). The aqueous phase was furtherextracted with EtOAc (3 × 20 mL), and the combined organicphases were dried (Na2SO4) and concentrated. The residue waspurified by column chromatography [silica gel EtOAc-hexane(1:100 to 1:50)].
  • 32
  • [ 5572-94-1 ]
  • C15H15F2NO3 [ No CAS ]
  • C21H20F2INO3 [ No CAS ]
  • 33
  • [ 5572-94-1 ]
  • [ 66-99-9 ]
  • (4-iodophenyl)(naphthalen-2-yl)methanol [ No CAS ]
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