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[ CAS No. 178752-79-9 ] {[proInfo.proName]}

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Chemical Structure| 178752-79-9
Chemical Structure| 178752-79-9
Structure of 178752-79-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 178752-79-9 ]

CAS No. :178752-79-9 MDL No. :MFCD01318996
Formula : C8H12BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YZQQHZXHCXAJAV-UHFFFAOYSA-N
M.W : 165.00 Pubchem ID :2762527
Synonyms :

Calculated chemistry of [ 178752-79-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.47
TPSA : 43.7 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) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : -0.57
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : -1.2
Consensus Log Po/w : -0.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 3.3 mg/ml ; 0.02 mol/l
Class : Very soluble
Log S (Ali) : -1.45
Solubility : 5.79 mg/ml ; 0.0351 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.39
Solubility : 6.72 mg/ml ; 0.0407 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 178752-79-9 ]

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 [ 178752-79-9 ]

* 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 [ 178752-79-9 ]
  • Downstream synthetic route of [ 178752-79-9 ]

[ 178752-79-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 178752-79-9 ]
  • [ 99-07-0 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10391 - 10398
  • 2
  • [ 16518-62-0 ]
  • [ 178752-79-9 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With n-butyllithium; Trimethyl borate In tetrahydrofuran; hexanes at -78 - -20℃; for 1.41667 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexanes; water for 0.0833333 h;
3-Bromo-N,N-dimethylaniline (500 mg, 2.50 mmol) was dissolved in THF (8 mL) and the solution was cooled to -78° C. n-Butyllithium (1.6M in hexanes, 1.56 mL, 3.75 mmol) was added drop-wise at -78° C. and the reaction mixture was stirred at this temperature for another 5 min. Trimethylborate (1.11 mL, 10.0 mmol) was added and the mixture was stirred for 1 h at -78° C. and was then left to warm to -20° C. over a period of 20 min. 2M HCl (3 mL) was added and the mixture was stirred for 5 min and was then neutralized by the addition of sat. NaHCO3 solution. The mixture was extracted with AcOEt (3.x.10 mL) and the combined organics were concentrated under reduced pressure to provide the crude boronic acid. Flash chromatography on silica gel eluting with acetone/CH2Cl2 1:1 provided 3-dimethylaminophenylboronic acid (251 mg, 61percent).
61%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.0833333 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexanes at -78 - -20℃; for 1.33 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexanes for 0.0833333 h;
[0230] (a) 3-Dimethylaminophenylboronic acid. 3-Bromo-N,N- dimethylaniline (500 mg, 2.50 mmol) was dissolved in THF (8 mL) and the solution was cooled to -78°C. n-Butyllithium (1.6M in hexanes, 1.56 mL, 3.75 mmol) was added drop- wise at -780C and the reaction mixture was stirred at this temperature for another 5 min. Trimethylborate (1.11 mL, 10.0 mmol) was added and the mixture was stirred for 1 h at -78°C and was then left to warm to -20°C over a period of 20 min. 2M HCl (3 mL) was added and the mixture was stirred for 5 min and was then neutralized by the addition of sat. NaHCO3 solution. The mixture was extracted with AcOEt (3x10 mL) and the combined organics were concentrated under reduced pressure to provide the crude boronic acid. Flash chromatography on silica gel eluting with acetone/CH2Cl2 1:1 provided 3-dimethylaminophenylboronic acid (251 mg, 61percent).
Reference: [1] Patent: US2006/270686, 2006, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2008/8059, 2008, A1, . Location in patent: Page/Page column 68
[3] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[4] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
  • 3
  • [ 121-43-7 ]
  • [ 16518-62-0 ]
  • [ 178752-79-9 ]
Reference: [1] Patent: US5914327, 1999, A,
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