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[ CAS No. 13331-23-2 ] {[proInfo.proName]}

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Chemical Structure| 13331-23-2
Chemical Structure| 13331-23-2
Structure of 13331-23-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13331-23-2 ]

CAS No. :13331-23-2 MDL No. :MFCD00799544
Formula : C4H5BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PZJSZBJLOWMDRG-UHFFFAOYSA-N
M.W :111.89 Pubchem ID :2734357
Synonyms :

Calculated chemistry of [ 13331-23-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 28.53
TPSA : 53.6 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) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.07
Log Po/w (WLOGP) : -1.04
Log Po/w (MLOGP) : -1.76
Log Po/w (SILICOS-IT) : -1.17
Consensus Log Po/w : -0.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.89
Solubility : 14.5 mg/ml ; 0.13 mol/l
Class : Very soluble
Log S (Ali) : -0.6
Solubility : 27.8 mg/ml ; 0.249 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.44
Solubility : 40.5 mg/ml ; 0.362 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.65

Safety of [ 13331-23-2 ]

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 [ 13331-23-2 ]

* 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 [ 13331-23-2 ]
  • Downstream synthetic route of [ 13331-23-2 ]

[ 13331-23-2 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 1104637-62-8 ]
  • [ 13331-23-2 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With water; sodium hydroxide In tetrahydrofuran at 23℃; for 0.333333 h;
Stage #2: Aqueous phosphate buffer
The general method for synthesizing unprotected organoboronic acids was as follows. Under ambient atmosphere, to a 100 mL flask equipped with a stir bar and charged with MIDA boronate (2) (5 mmol) as a solution in THF (50 mL) was added aqueous NaOH (1.0 M, 15 mL). The mixture was vigorously stirred for 20 min. The mixture was then transferred to a separatory funnel and was diluted with EbO (50 mL) and 0.5 M pH 7 sodium phosphate buffer (50 mL). The mixture was shaken, and the phases were separated. The aqueous phase was extracted with THFiEt2O (1 :1 , 2 x 25 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. Residual solvent was co-evaporated with MeCN, and the resulting solid was placed under vacuum ( ~ 1 Torr) for 30 min. All boronic acids thus obtained were judged to be > 95percent pure by 1 H-NMR and were utilized in cross-coupling reactions immediately after preparation. An example of this method is depicted in the scheme below. To form unprotected organoboronic acid 1a, the general procedure was followed using MIDA boronate 2a (1.127 g, 5.002 mmol) to yield the 1a as an off white solid (0.531 g, 95percent). TLC (EtOAc) Rf = 0.46, stained with KMnO4. 1H-NMR (500 MHz, DMSO-d6:D2O 95:5 w/ TMS) δ 7.81 (dd, / = 1 .5, 0.5 Hz, 1 H), 7.07 (dd, / = 3.0, 0.5 Hz, 1 H), 6.48 (dd, / = 3.5, 2.0 Hz, 1 H). 13C-NMR (125 MHz, DMSO-d6:D2O 95:5 w/ TMS) δ 146.4, 121.5, 1 10.3. HRMS (El +) Calculated for C4HsO3B (M) + : 1 12.0332, Found: 1 12.0332.
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
[2] Patent: WO2010/36921, 2010, A2, . Location in patent: Page/Page column 41
  • 2
  • [ 534-22-5 ]
  • [ 121-43-7 ]
  • [ 13331-23-2 ]
Reference: [1] Patent: US2015/266914, 2015, A1, . Location in patent: Paragraph 0147; 0260
[2] Patent: US2015/266914, 2015, A1, . Location in patent: Paragraph 0276
  • 3
  • [ 110-00-9 ]
  • [ 121-43-7 ]
  • [ 7732-18-5 ]
  • [ 13331-23-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 30 - 38
  • 4
  • [ 584-12-3 ]
  • [ 150-46-9 ]
  • [ 13331-23-2 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 1, p. 156 - 159
  • 5
  • [ 3187-94-8 ]
  • [ 13331-23-2 ]
Reference: [1] Patent: US2002/161230, 2002, A1,
  • 6
  • [ 110-00-9 ]
  • [ 5419-55-6 ]
  • [ 13331-23-2 ]
Reference: [1] Patent: US6258822, 2001, B1,
[2] Patent: US6284796, 2001, B1,
  • 7
  • [ 110-00-9 ]
  • [ 5419-55-6 ]
  • [ 13331-23-2 ]
Reference: [1] Patent: US5994394, 1999, A,
  • 8
  • [ 2786-02-9 ]
  • [ 121-43-7 ]
  • [ 13331-23-2 ]
Reference: [1] Patent: WO2004/24738, 2004, A1, . Location in patent: Page/Page column 15-16
  • 9
  • [ 1104637-62-8 ]
  • [ 7732-18-5 ]
  • [ 13331-23-2 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
  • 10
  • [ 110-00-9 ]
  • [ 121-43-7 ]
  • [ 13331-23-2 ]
Reference: [1] Patent: WO2005/30121, 2005, A2, . Location in patent: Figure 11
[2] Patent: WO2005/30121, 2005, A2, . Location in patent: Figure 11
  • 11
  • [ 121-43-7 ]
  • [ 531514-49-5 ]
  • [ 13331-23-2 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 111 - 115
[2] , Gmelin Handbook: B: B-Verb.13, 4.7.2.2, page 189 - 196,
  • 12
  • [ 166328-14-9 ]
  • [ 7732-18-5 ]
  • [ 13331-23-2 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7431 - 7441
  • 13
  • [ 166328-14-9 ]
  • [ 13331-23-2 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7431 - 7441
  • 14
  • [ 13331-23-2 ]
  • [ 540-37-4 ]
  • [ 59147-02-3 ]
YieldReaction ConditionsOperation in experiment
92% With C7H10N2*Pd(2+)*2Cl(1-); potassium carbonate In methanol; water for 0.166667 h; Reflux; Schlenk technique General procedure: A 20mL Schlenk tube with a magnetic stir bar was charged with aryl halide (2mmol), arylboronic acid (2.4mmol), K2CO3 (5mmol), 10mL of solvent [H2O, H2O–MeOH (1:1), H2O–EtOH (1:1), H2O–EG (1:1)] and an aliquot of 0.01M solution of palladium complexes PdCl2(L)2 or Pd[(L)4]Cl2 in MeOH (0.001–0.2molpercent) under air atmosphere. The reaction mixture was placed in a preheated oil bath: at 100°C for MeOH–H2O, at 110°C for EtOH–H2O, at 140°C for H2O and at 160°C for EG–H2O; and stirred under reflux for the given time. After this time, the mixture was cooled, acidified by 5M HCl (in the case of acids) and diluted with 10mL of H2O and 10mL of Et2O (or EtOAc). The organic phase was separated, and the aqueous layer was extracted with Et2O EtOAc) (2×10mL). The combined organic layers were washed with H2O (10mL), brine (10mL), and dried over Na2SO4. The pure products were obtained by a simple filtration of ether solution through silica gel pad and evaporation of a solvent.
Reference: [1] Catalysis Communications, 2016, vol. 79, p. 17 - 20
  • 15
  • [ 13331-23-2 ]
  • [ 106-40-1 ]
  • [ 59147-02-3 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 43, p. 5733 - 5736
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 9, p. 935 - 940
  • 16
  • [ 13331-23-2 ]
  • [ 1168136-15-9 ]
  • [ 7742-73-6 ]
  • [ 1168136-22-8 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 25, p. 3081 - 3083
  • 17
  • [ 13331-23-2 ]
  • [ 2398-37-0 ]
  • [ 35461-93-9 ]
YieldReaction ConditionsOperation in experiment
97% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In methanol; toluene at 100℃; for 16 h; Inert atmosphere General procedure: According to a procedure by Oxford et al.,[3] furan-2-boronic acid (168 mg, 1.5 mmol, 1.5 eq), aryl halide (1.0 mmol, 1.0 eq), Pd(PPh3)4 (116 mg, 0.1 mmol, 10 molpercent) and cesium carbonate (350 mg, 1.1 mmol, 1.1 eq) were suspended in a toluene/MeOH mixture (4:1, 10 mL). The reaction mixture was stirred for 16 h at 100 °C. The reaction mixture was diluted with EtOAc (8 mL) and the organic layer was extracted was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 2, p. 260 - 268
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