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[ CAS No. 17933-03-8 ] {[proInfo.proName]}

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Chemical Structure| 17933-03-8
Chemical Structure| 17933-03-8
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Product Details of [ 17933-03-8 ]

CAS No. :17933-03-8 MDL No. :MFCD00040198
Formula : C7H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BJQCPCFFYBKRLM-UHFFFAOYSA-N
M.W : 135.96 Pubchem ID :2733950
Synonyms :

Calculated chemistry of [ 17933-03-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.23
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : -0.33
Log Po/w (MLOGP) : 0.61
Log Po/w (SILICOS-IT) : -0.3
Consensus Log Po/w : 0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.1 mg/ml ; 0.0155 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.15 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.64
Solubility : 3.09 mg/ml ; 0.0227 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 17933-03-8 ]

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

Application In Synthesis of [ 17933-03-8 ]

* 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 [ 17933-03-8 ]
  • Downstream synthetic route of [ 17933-03-8 ]

[ 17933-03-8 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 17933-03-8 ]
  • [ 4467-07-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516
  • 2
  • [ 121-43-7 ]
  • [ 591-17-3 ]
  • [ 17933-03-8 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With iodine; magnesium In tetrahydrofuran at -50℃; Reflux
Stage #2: Heating
The reaction flask was charged with 0.10 mol (0.1 eq) m-bromotoluene, 1.1 mol (1.1 eq) magnesium turnings, a few grains of simple iodine, 800 ml THF, stirred, and warmed to reflux. When Grignard initiated, 0.90 mol (0.9 eq) of m-bromotoluene was continuously added dropwise under the reflux condition, and the reaction of refluxing and keeping warm was completed. The reaction time is reached and the temperature is reduced to -50.0°C. 2.2 mol (2.2 eq) of trimethyl borate was added dropwise, and the reaction was incubated until the reaction of the raw materials was complete, and the temperature was raised and water was added. Hydrochloric acid was added dropwise, the pH was adjusted to 1-2, the reaction was incubated, the reaction time was reached, rotary evaporation, suction drying, and beating and purification were performed to obtain 0.90 mol of 3-methylphenylboronic acid as a white solid, 0.03percent of water, and a purity of 98.86percent. The yield was 90.0percent.
Reference: [1] Patent: CN106946924, 2017, A, . Location in patent: Paragraph 0009; 0020; 0023; 0026
[2] Patent: US5183653, 1993, A,
  • 3
  • [ 67-56-1 ]
  • [ 55124-35-1 ]
  • [ 591-17-3 ]
  • [ 17933-03-8 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667 h;
Stage #2: at 70℃;
General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H2O.
Reference: [1] Tetrahedron, 2019, vol. 75, # 2, p. 164 - 171
  • 4
  • [ 591-17-3 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 20, p. 7110 - 7123
[2] Patent: US6150413, 2000, A,
[3] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1115 - 1118
[4] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[5] Organic Letters, 2016, vol. 18, # 11, p. 2716 - 2718
  • 5
  • [ 5419-55-6 ]
  • [ 591-17-3 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 23, p. 5612 - 5615
[2] Organic Letters, 2015, vol. 17, # 2, p. 346 - 349
  • 6
  • [ 253342-48-2 ]
  • [ 17933-03-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 35, p. 6657 - 6660
  • 7
  • [ 109-72-8 ]
  • [ 121-43-7 ]
  • [ 591-17-3 ]
  • [ 17933-03-8 ]
Reference: [1] Patent: US5597832, 1997, A,
  • 8
  • [ 13675-18-8 ]
  • [ 591-17-3 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
  • 9
  • [ 7732-18-5 ]
  • [ 108-88-3 ]
  • [ 73183-34-3 ]
  • [ 17933-03-8 ]
  • [ 5720-05-8 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 4, p. 886 - 889
  • 10
  • [ 13675-18-8 ]
  • [ 33046-97-8 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
  • 11
  • [ 108-88-3 ]
  • [ 73183-34-3 ]
  • [ 17933-03-8 ]
  • [ 5720-05-8 ]
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
  • 12
  • [ 625-95-6 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14006 - 14008
  • 13
  • [ 40881-44-5 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
  • 14
  • [ 10325-82-3 ]
  • [ 19287-45-7 ]
  • [ 17933-03-8 ]
Reference: [1] Journal of Organometallic Chemistry, 1980, vol. 195, # 2, p. 147 - 154
  • 15
  • [ 108-88-3 ]
  • [ 17933-03-8 ]
  • [ 5720-05-8 ]
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
  • 16
  • [ 13195-76-1 ]
  • [ 17933-03-8 ]
Reference: [1] Chemische Berichte, 1909, vol. 42, p. 3095
  • 17
  • [ 7722-64-7 ]
  • [ 17933-03-8 ]
  • [ 25487-66-5 ]
YieldReaction ConditionsOperation in experiment
61.2% With sodium hydroxide In water at 30 - 40℃; 250 ml of aqueous sodium hydroxide solution (30percent) was added to the reaction flask, 0.90 mol of 3-methylphenylboronic acid was prepared as described above, and the temperature was controlled to 30-40° C. under stirring. Potassium permanganate 1.50 mol ( 1.7eq) was added in batches, feeding was completed, and the reaction was incubated until the reaction of the raw materials was complete, suction filtration, rotary evaporation, acidification, suction filtration, and beating purification to obtain 0.612 mol 3-carboxyphenylboronic acid as a white solid, purity 99.5percent, yield 61.2percent .
Reference: [1] Patent: CN106946924, 2017, A, . Location in patent: Paragraph 0011; 0019; 0021; 0022; 0024; 0025; 0027
  • 18
  • [ 17933-03-8 ]
  • [ 25487-66-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 153,169,170
[2] Patent: US5183653, 1993, A,
[3] Tetrahedron, 1963, vol. 19, p. 821 - 826
[4] J. Prakt. Chem. (2), 1930, vol. 128, p. 153 - 170
[5] Liebigs Annalen der Chemie, 1901, vol. 315, p. 26 - 40
[6] Arkiv foer Kemi, 1957, vol. 10, p. 473 - 482
[7] Arkiv foer Kemi, 1957, vol. 10, p. 513 - 521
[8] Journal of the American Chemical Society, 1934, vol. 56, p. 1865 - 1870
[9] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 19
  • [ 17933-03-8 ]
  • [ 87199-16-4 ]
YieldReaction ConditionsOperation in experiment
73% With dipotassium peroxodisulfate; iron(II) acetylacetonate In water; acetonitrile at 80℃; for 12 h; Ferroacetylacetonate (0.025mmol), polymethylhydrogensiloxane0 75mmol), Potassium persulfate (0.25mmol), lah (0.25mmol), AcetonitrilelmL),waterlmL),in the reaction mixture 80 ° C reaction under 12 h. The reaction is finished adding ammonia water (2 ml) to remove the peripheric, add saturated salt water 10 ml, and extraction with ethyl ether (10 ml × 3), the combined organic phase, pressure reducing evaporate the solvent column chromatography to obtain yield 73percent.
Reference: [1] Patent: CN107216242, 2017, A, . Location in patent: Paragraph 0092; 0093
  • 20
  • [ 17933-03-8 ]
  • [ 51323-43-4 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
[2] Arkiv foer Kemi, 1957, vol. 10, p. 507,509
  • 21
  • [ 128-08-5 ]
  • [ 17933-03-8 ]
  • [ 51323-43-4 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 22
  • [ 17933-03-8 ]
  • [ 87199-17-5 ]
  • [ 400744-83-4 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With iodine; potassium carbonate In acetonitrile at 80℃; for 8 h; Inert atmosphere; Schlenk technique; Sealed tube
Stage #2: With palladium diacetate In acetonitrile at 80℃; for 12 h; Inert atmosphere; Schlenk technique; Sealed tube
General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t., and thenarylboronic acid 1′ (0.75 mmol) and Pd(OAc)2 (0.025 mmol, 5.6 mg) were added, and the mixture stirred at 80 °C for 12–16 h. The resulting solution was cooled to r.t. and H2O (10mL) was added. The aq layer was extracted with EtOAc(3 × 5 mL). The combined organic phase was dried overanhydrous Na2SO4, filtered and concentrated by rotaryevaporation, and the residue was purified by columnchromatography on silica gel to provide the desired product3a–v. Data for three representative examples are provided
Reference: [1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
  • 23
  • [ 17933-03-8 ]
  • [ 1122-91-4 ]
  • [ 400744-83-4 ]
Reference: [1] Applied Organometallic Chemistry, 2017, vol. 31, # 4,
[2] Journal of Mass Spectrometry, 2008, vol. 43, # 4, p. 542 - 546
  • 24
  • [ 17933-03-8 ]
  • [ 104-88-1 ]
  • [ 400744-83-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 5, p. 1507 - 1510
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 42, p. 10090 - 10094
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 18, p. 3924 - 3929
  • 25
  • [ 69088-97-7 ]
  • [ 17933-03-8 ]
  • [ 400744-83-4 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 14, p. 1967 - 1969
  • 26
  • [ 3132-99-8 ]
  • [ 17933-03-8 ]
  • [ 216443-78-6 ]
Reference: [1] Patent: US6150413, 2000, A,
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