Home Cart 0 Sign in  

[ CAS No. 10365-98-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 10365-98-7
Chemical Structure| 10365-98-7
Structure of 10365-98-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 10365-98-7 ]

Related Doc. of [ 10365-98-7 ]

Alternatived Products of [ 10365-98-7 ]

Product Details of [ 10365-98-7 ]

CAS No. :10365-98-7 MDL No. :MFCD00161359
Formula : C7H9BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :NLLGFYPSWCMUIV-UHFFFAOYSA-N
M.W :151.96 Pubchem ID :2734370
Synonyms :

Calculated chemistry of [ 10365-98-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.76
TPSA : 49.69 Ų

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) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : -0.63
Log Po/w (MLOGP) : 0.0
Log Po/w (SILICOS-IT) : -0.76
Consensus Log Po/w : -0.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.56
Solubility : 4.21 mg/ml ; 0.0277 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 5.71 mg/ml ; 0.0376 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.4
Solubility : 6.08 mg/ml ; 0.04 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 10365-98-7 ]

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 [ 10365-98-7 ]

* 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 [ 10365-98-7 ]
  • Downstream synthetic route of [ 10365-98-7 ]

[ 10365-98-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 10365-98-7 ]
  • [ 106-95-6 ]
  • [ 24743-14-4 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 27, p. 3590 - 3592
  • 2
  • [ 10365-98-7 ]
  • [ 536-90-3 ]
  • [ 92248-06-1 ]
YieldReaction ConditionsOperation in experiment
25% With pyridine In dichloromethane at 20℃; for 72 h; λ/-[2-(bis-3-methoxyphenylamino)ethyllacetamide (5c):Cupric acetate (2.1 mmol) and pyridine (0.25 ml) were added to a vigorously stirred solution of 3-methoxyaniline (1 mmol) and 3-methoxyphenylboronic acid (2 mmol) in dry methylene chloride (3.5 ml), under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 72 h (the progress of the reaction was monitored by TLC). λ/-(3-Methoxyphenyl)-3-methoxyaniline (3c) was isolated by direct flash chromatography of the crude reaction mixture following preabsorption on silica gel. Yield (3c): 25percent; EI-MS 229 (M+) [Lit.: Urgaonkar, S.; Verkade, J.G. J. Org. Chem. 2004, 69, 9135-9142].
Reference: [1] Patent: WO2007/79593, 2007, A1, . Location in patent: Page/Page column 31
  • 3
  • [ 10365-98-7 ]
  • [ 92248-06-1 ]
Reference: [1] Synlett, 2009, # 19, p. 3198 - 3200
[2] Chemistry Letters, 2009, vol. 38, # 7, p. 708 - 709
  • 4
  • [ 2398-37-0 ]
  • [ 10365-98-7 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere; Schlenk technique
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 16 h; Inert atmosphere; Schlenk technique
1-bromo-3-methoxybenzene (20 g, 107 mmol) was dissolved in dry THF (200 mL) in a Schlenk tube. The solution was purged with N2 and cooled to -78 ºC. n-Butyllithium (2.5 mol/L, 64.2 mL) was added slowly. A white precipitate was formed during the addition. The mixture was stirred for 1 h at the same temperature and then trimethyl borate (74 mL, 321.0 mmol) was added. The resulting clear solution was slowly warmed to room temperature and stirred for 16 h. Concentrated hydrochloric acid was added until a pH of 3-4 was reached. The reaction mixture was poured into ethyl acetate (200 mL) and the aqueous layer was discarded. The organic layer was washed three times with saturated salt water, dried over anhydrous Na2SO4 and filtered. The solvent was removed and the product was recrystallized from ethyl acetate/petroleum ether (1:10) to afford the title compound (13.8 g, 85 percent). 1H NMR (DMSO-d6, 400 MHz, ppm): δ 8.02 (s, 2H, OH-H), 7.36 (d, J = 4.0 Hz, 2H, Ar-H), 7.25 (t, J = 8.0 Hz, 1H, Ar-H), 6.95 (d, J = 8.0 Hz, 2H, Ar-H), 3.75 (s, 3H, CH3-H); 13C NMR (CDCl3, 100 MHz, ppm): δ 158.55, 128.48, 126.32, 118.98, 115.72, 54.78.
78%
Stage #1: With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran; hexaneInert atmosphere
General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 °C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 °C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 °C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried.
Reference: [1] Tetrahedron, 2013, vol. 69, # 19, p. 3934 - 3941
[2] Patent: US6342610, 2002, B2, . Location in patent: Page column 75
[3] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[4] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4212 - 4218
[5] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[6] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
  • 5
  • [ 2398-37-0 ]
  • [ 121-43-7 ]
  • [ 10365-98-7 ]
YieldReaction ConditionsOperation in experiment
92.1% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane 1st Stage
3-Methoxybenzeneboronic Acid
41.3 g (220 mmol) 3-bromoanisole were dissolved in 880 ml tetrahydrofuran and the solution was cooled to -70° C. in a cooling bath (ethanol/dry ice).
160 ml (250 mmol) butyllithium solution (1.6 M in hexane) were added dropwise under nitrogen such that the temperature did not rise above -60° C.
After stirring at -70° C. for 1.5 hours, 75 ml (660 mmol) trimethyl borate were also added dropwise such that the temperature did not rise above -60° C.
After stirring in the cold for a further hour, the mixture was warmed to 25° C. in the course of two hours, 720 ml hydrochloric acid (1 M) were added and the mixture was stirred at 25° C. for 15 hours.
For working up, the mixture was extracted three times with 300 ml ether each time, the organic phases were combined, washed with 100 ml each of water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered and the filtrate was concentrated on a rotary evaporator (500-10 mbar).
In this manner, 30.8 g 3-methoxybenzeneboronic acid (92.1percent of theory) were obtained.
80%
Stage #1: With magnesium In tetrahydrofuran; toluene at 60 - 80℃; Inert atmosphere
Stage #2: at 0℃; Inert atmosphere
Stage #3: With sulfuric acid In tetrahydrofuran; toluene at 20℃; Inert atmosphere
To a mixture of magnesium (2.95 g, 121mmol), THF (35mL), and toluene (35 mL)was added dropwise 3-bromoanisole 2(13.0 mL, 103mmol)with keeping temperature at 60 ºC. The reaction mixture was stirred at 80 ºC for 2hours. Prepared Grignard reagent was slowly dropwise to a toluene solution (20 mL) of trimethyl borate (11.4 mL, 102 mmol) at 0 ºC. The reaction mixture was stirred at 0 ºC for 2 hours, then neutralized with 10percent sulfuric acid, and stirred at r.t. overnight. Organic phase was separated, dried over MgSO4, and evaporated to give 3-methoxyphenylboronic acid (12.36 g, 80percent) as white powder.
Reference: [1] Patent: US2002/198251, 2002, A1,
[2] Tetrahedron Letters, 2012, vol. 53, # 46, p. 6182 - 6185,4
[3] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 17, p. 2513 - 2523
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922
  • 6
  • [ 2398-37-0 ]
  • [ 5419-55-6 ]
  • [ 10365-98-7 ]
YieldReaction ConditionsOperation in experiment
156.1 g
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1 h; Inert atmosphere
Stage #2: at 20℃; for 18 h; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water
n-Butyllithium in n-hexane (925.0 mL, 1.59 M) was added dropwise to a mixture of THF (1,000 mL) and 1-bromo-3-methoxybenzene (T-1) (250.0 g, 1.34 mol) at -70° C. under an atmosphere of nitrogen.
After the addition had been completed, the reaction mixture was stirred at the same temperature for 1 hour. Triisopropyl borate (300.9 g, 1.60 mol) was added dropwise, and then the mixture was warmed slowly to room temperature.
The stirring was continued at room temperature for 18 hours, and the reaction mixture was poured into 6M-hydrochloric acid. The mixture was extracted with ethyl acetate (500 mL) four times, and the organic layer was washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure.
The residue was sufficiently washed with heptane to leave colorless solids (156.1 g) of 3-methoxyphenylboronic acid (T-2).
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 23, p. 5612 - 5615
[2] Chemistry - A European Journal, 2017, vol. 23, # 4, p. 935 - 945
[3] Patent: US8394468, 2013, B2, . Location in patent: Page/Page column 52; 53
[4] Organic Letters, 2015, vol. 17, # 2, p. 346 - 349
[5] Journal of Materials Chemistry C, 2015, vol. 3, # 22, p. 5754 - 5763
  • 7
  • [ 7732-18-5 ]
  • [ 10365-98-7 ]
YieldReaction ConditionsOperation in experiment
85% at 25℃; for 2 h; General procedure: In a flask containing the appropriate potassiumorganotrifluoroborate (0.5 mmol) in distilled water(1 mL) was added montmorillonite K10 (150percent m/m). Themixture was stirred for the time indicated in Scheme 1at room temperature. After this period, the mixture wasextracted with EtOAc (3 × 10 mL) and the organic phasewas washed with water (2 × 15 mL). The organic phasewas dried over anhydrous MgSO4, filtered and the solventwas removed in vacuo to yield the corresponding boronicacids 2a-o.
Reference: [1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 9, p. 1777 - 1785
  • 8
  • [ 325142-84-5 ]
  • [ 10365-98-7 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 35, p. 6657 - 6660
  • 9
  • [ 13675-18-8 ]
  • [ 2398-37-0 ]
  • [ 10365-98-7 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
  • 10
  • [ 100-66-3 ]
  • [ 73183-34-3 ]
  • [ 10365-98-7 ]
  • [ 5720-07-0 ]
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[3] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
  • 11
  • [ 157670-38-7 ]
  • [ 10365-98-7 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
  • 12
  • [ 100-66-3 ]
  • [ 10365-98-7 ]
  • [ 5720-07-0 ]
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
  • 13
  • [ 13195-76-1 ]
  • [ 36282-40-3 ]
  • [ 10365-98-7 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 153,169,170
  • 14
  • [ 10365-98-7 ]
  • [ 89694-46-2 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 4, p. 1042 - 1045
  • 15
  • [ 10365-98-7 ]
  • [ 89694-44-0 ]
YieldReaction ConditionsOperation in experiment
61% With N-Bromosuccinimide; triphenylphosphine sulfide In dichloromethane at 20℃; for 48 h; Inert atmosphere Under an argon atmosphere,To a 300 mL 2-diameter eggplant-shaped flask, 3-methoxyphenylboronic acid (12)(9.12 g, 60.0 mmol),Triphenylphosphine sulfide (932 mg, 6.00 mmol),Dichloromethane (200 mL) was added,This was stirred to make a homogeneous solution.In contrast, N-bromosuccinimide (13.0 g, 72.0 mmol) was added,And the mixture was stirred at room temperature for 2 days.To the reaction mixture was added a saturated aqueous solution of sodium thiosulfate to stop the reaction, followed by extraction with dichloromethane (100 mL × 3).The combined organic layer was washed with saturated brine and dried over sodium sulfate.After filtration, concentration under reduced pressure gave a crude product.Purification by silica gel column chromatography (290 g, n-hexane / acetone = 1/1) gave 2-bromo-5-methoxyphenylboronic acid (8b) (8.45 g, 36.6 mmol, yield 61.0 percent) Was obtained.
Reference: [1] Organic Letters, 2010, vol. 12, # 11, p. 2480 - 2483
[2] Patent: JP2018/30788, 2018, A, . Location in patent: Paragraph 0057
[3] Organic Letters, 2015, vol. 17, # 4, p. 1042 - 1045
  • 16
  • [ 584-12-3 ]
  • [ 10365-98-7 ]
  • [ 35461-93-9 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 14, p. 2138 - 2146
[2] Synthesis, 2011, # 5, p. 731 - 738
  • 17
  • [ 110-00-9 ]
  • [ 10365-98-7 ]
  • [ 35461-93-9 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 578 - 580
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 10365-98-7 ]

Organoboron

Chemical Structure| 192182-54-0

[ 192182-54-0 ]

3,5-Dimethoxybenzeneboronic acid

Similarity: 0.98

Chemical Structure| 5720-07-0

[ 5720-07-0 ]

4-Methoxyphenylboronic acid

Similarity: 0.98

Chemical Structure| 90555-66-1

[ 90555-66-1 ]

3-Ethoxyphenylboronic acid

Similarity: 0.96

Chemical Structure| 22237-13-4

[ 22237-13-4 ]

4-Ethoxyphenylboronic acid

Similarity: 0.94

Chemical Structure| 149557-18-6

[ 149557-18-6 ]

3-Propoxyphenylboronic acid

Similarity: 0.92

Aryls

Chemical Structure| 192182-54-0

[ 192182-54-0 ]

3,5-Dimethoxybenzeneboronic acid

Similarity: 0.98

Chemical Structure| 5720-07-0

[ 5720-07-0 ]

4-Methoxyphenylboronic acid

Similarity: 0.98

Chemical Structure| 90555-66-1

[ 90555-66-1 ]

3-Ethoxyphenylboronic acid

Similarity: 0.96

Chemical Structure| 22237-13-4

[ 22237-13-4 ]

4-Ethoxyphenylboronic acid

Similarity: 0.94

Chemical Structure| 149557-18-6

[ 149557-18-6 ]

3-Propoxyphenylboronic acid

Similarity: 0.92

Ethers

Chemical Structure| 192182-54-0

[ 192182-54-0 ]

3,5-Dimethoxybenzeneboronic acid

Similarity: 0.98

Chemical Structure| 5720-07-0

[ 5720-07-0 ]

4-Methoxyphenylboronic acid

Similarity: 0.98

Chemical Structure| 90555-66-1

[ 90555-66-1 ]

3-Ethoxyphenylboronic acid

Similarity: 0.96

Chemical Structure| 22237-13-4

[ 22237-13-4 ]

4-Ethoxyphenylboronic acid

Similarity: 0.94

Chemical Structure| 149557-18-6

[ 149557-18-6 ]

3-Propoxyphenylboronic acid

Similarity: 0.92