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[ CAS No. 4612-26-4 ] {[proInfo.proName]}

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Chemical Structure| 4612-26-4
Chemical Structure| 4612-26-4
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Product Details of [ 4612-26-4 ]

CAS No. :4612-26-4 MDL No. :MFCD00236018
Formula : C6H8B2O4 Boiling Point : -
Linear Structure Formula :(OH)2B(C6H4)B(OH)2 InChI Key :BODYVHJTUHHINQ-UHFFFAOYSA-N
M.W : 165.75 Pubchem ID :230478
Synonyms :

Calculated chemistry of [ 4612-26-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 4.0
Molar Refractivity : 46.09
TPSA : 80.92 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.27
Log Po/w (WLOGP) : -2.95
Log Po/w (MLOGP) : -1.47
Log Po/w (SILICOS-IT) : -3.26
Consensus Log Po/w : -1.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.94
Solubility : 19.2 mg/ml ; 0.116 mol/l
Class : Very soluble
Log S (Ali) : -0.97
Solubility : 17.7 mg/ml ; 0.107 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.17
Solubility : 112.0 mg/ml ; 0.675 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 4612-26-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4612-26-4 ]

* 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 [ 4612-26-4 ]
  • Downstream synthetic route of [ 4612-26-4 ]

[ 4612-26-4 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 4612-26-4 ]
  • [ 3365-85-3 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 10, p. 1343 - 1346
  • 2
  • [ 121-43-7 ]
  • [ 106-37-6 ]
  • [ 4612-26-4 ]
YieldReaction ConditionsOperation in experiment
84.6%
Stage #1: With iodine; magnesium In tetrahydrofuran at 30℃; for 3 h; Inert atmosphere
Stage #2: at -70℃; for 1 h;
under the protection of nitrogen, into 200 ml THF, 15 . 0g (0.62 µM) magnesium,1.0g(0.004mol)I2, slowly dropping containing 68.4g (0.29 µM) of the two 1, 4 - bromobenzene 300 ml THF solution, adds by drops in 30 °C reaction 3h, cooling to -70 °C, slowly dropping boric acid three methyl ester (78.5 ml, 0 . 72 µM) and 300 ml THF of a mixed solution of the, completion of the dropping, for -70 °C reaction 1h, Slowly to room temperature stirring 12h. Adding 2.5M HCl950ml fast stirring 15min, filtering, with 300 ml hexane washing three times, vacuum drying, the white solid obtained 40.7g, yield of 84.6percent.
Reference: [1] Patent: CN103570530, 2016, B, . Location in patent: Paragraph 0042; 0043
  • 3
  • [ 106-37-6 ]
  • [ 4612-26-4 ]
Reference: [1] Chemistry - An Asian Journal, 2013, vol. 8, # 7, p. 1368 - 1371
[2] Synthesis, 2002, # 6, p. 757 - 760
[3] Chemical Communications, 2000, # 8, p. 681 - 682
[4] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 377, p. 109 - 112
[5] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 16219 - 16234
[6] CrystEngComm, 2013, vol. 15, # 11, p. 2067 - 2075
  • 4
  • [ 121-43-7 ]
  • [ 7519-94-0 ]
  • [ 4612-26-4 ]
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 1957, vol. 79, p. 3081 - 3084
[3] , Gmelin Handbook: B: B-Verb.13, 4.7.2.4, page 203 - 209,
  • 5
  • [ 2449-19-6 ]
  • [ 4612-26-4 ]
Reference: [1] , Gmelin Handbook: B: B-Verb.9, 5.2.8.3, page 226 - 229,
[2] Journal of the American Chemical Society, [3] Journal of the American Chemical Society, 1957, vol. 79, p. 3081 - 3084
  • 6
  • [ 13283-31-3 ]
  • [ 7732-18-5 ]
  • [ 1012-73-3 ]
  • [ 4612-26-4 ]
  • [ 1631-73-8 ]
Reference: [1] Organometallics, 2002, vol. 21, # 22, p. 4886 - 4888
  • 7
  • [ 13675-18-8 ]
  • [ 637-87-6 ]
  • [ 4612-26-4 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
  • 8
  • [ 93687-09-3 ]
  • [ 4612-26-4 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 6, p. 1826 - 1833
[2] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 16219 - 16234
  • 9
  • [ 71258-12-3 ]
  • [ 4612-26-4 ]
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 1957, vol. 79, p. 3081 - 3084
[3] , Gmelin Handbook: B: B-Verb.9, 5.2.8.3, page 226 - 229,
  • 10
  • [ 121-43-7 ]
  • [ 106-37-6 ]
  • [ 7732-18-5 ]
  • [ 4612-26-4 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 16219 - 16234
  • 11
  • [ 2425-81-2 ]
  • [ 4612-26-4 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1970, p. 488 - 493
  • 12
  • [ 4612-26-4 ]
  • [ 71597-85-8 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 9, p. 5283 - 5291
  • 13
  • [ 4612-26-4 ]
  • [ 71597-85-8 ]
  • [ 123-31-9 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 9, p. 6501 - 6504
  • 14
  • [ 1120-87-2 ]
  • [ 4612-26-4 ]
  • [ 113682-56-7 ]
YieldReaction ConditionsOperation in experiment
90% With C37H45ClN2O3PPd; potassium carbonate In ethanol; water at 80℃; for 6 h; Inert atmosphere; Schlenk technique A 10-mL round-bottom flask was charged with the prescribe damount of catalyst, 1,4-benzenediboronic acid (0.5 mmol), N-heteroaryl halides (1.5 mmol), the selected base (1.5 mmol) and solvent (4 mL). The flask was placed in an oil bath and heated at 80 °C for 6 h, then cooled to room temperature and extracted with CH2Cl2. The crude products obtained from evaporation were purified by flash chromatography on silica gel. The products 5b–c, 5f, 5m [21], 5d [22], 5e [23], 5l [24] were known compounds and characterized by the comparison of data with those in the literature. The products 5a, 5g–k, 5n–o were new compounds and characterized by elemental analysis, IR, MS,1H and 13C NMR.
Reference: [1] Transition Metal Chemistry, 2015, vol. 40, # 5, p. 501 - 508
  • 15
  • [ 4612-26-4 ]
  • [ 19524-06-2 ]
  • [ 113682-56-7 ]
Reference: [1] Dalton Transactions, 2014, vol. 43, # 16, p. 6100 - 6107
[2] Inorganic Chemistry, 2014, vol. 53, # 14, p. 7591 - 7598
  • 16
  • [ 4612-26-4 ]
  • [ 158938-08-0 ]
Reference: [1] Patent: CN103570530, 2016, B,
  • 17
  • [ 580-13-2 ]
  • [ 4612-26-4 ]
  • [ 918655-03-5 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 2 h; 2-bromo-naphthalene (2.07g, 10mmol), benzene-1,4-diBoronic acid(2.49g, 15mmol), Pd (PPh3) 4 (0.58 g, 0.5mmol), potassium carbonate (4.15g, 30mmol) and THF: H2O = 2:1 solution dissolved in 200ml 80 After 2 hours reflux agitation. Thereafter it was added and extracted three times with 40ml ethyl ether H2O40ml drying the obtained organic layer with magnesium sulfate, and separating the residue obtained by evaporating the solvent was subjected to silica gel column chromatography purification Intermediate B-1 (1.98g, 80percent yield) It was obtained.
Reference: [1] Patent: KR2016/30001, 2016, A, . Location in patent: Paragraph 0327-0330
  • 18
  • [ 1120-87-2 ]
  • [ 4612-26-4 ]
  • [ 1045332-30-6 ]
YieldReaction ConditionsOperation in experiment
9.8 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 6 h; Inert atmosphere; Reflux Will 10 grams of 4-bromopyridine,11 grams of 1,4-benzenediboronic acid,20 grams of sodium carbonate,120 ml of toluene,80 ml of ethanol,40 ml of water was added to a 500 ml three-necked bottle.Under nitrogen protection,0.65g of Pd(pph3)4 was added,Heated to reflux,The reaction is complete after 6 hoursCooling,The solid obtained by suction filtrationWash with ethyl acetate,Get the product,9.8 grams.
Reference: [1] Patent: CN107759572, 2018, A, . Location in patent: Paragraph 0212; 0213
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