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[ CAS No. 72054-56-9 ] {[proInfo.proName]}

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Chemical Structure| 72054-56-9
Chemical Structure| 72054-56-9
Structure of 72054-56-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 72054-56-9 ]

CAS No. :72054-56-9 MDL No. :MFCD12025077
Formula : C9H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :NNNRGWOWXNCGCV-UHFFFAOYSA-N
M.W : 210.07 Pubchem ID :12886548
Synonyms :

Calculated chemistry of [ 72054-56-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.8
TPSA : 23.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.79
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.55
Log Po/w (SILICOS-IT) : 3.14
Consensus Log Po/w : 2.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.141 mg/ml ; 0.000673 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.238 mg/ml ; 0.00113 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.15
Solubility : 0.0148 mg/ml ; 0.0000706 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 72054-56-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 72054-56-9 ]

* 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 [ 72054-56-9 ]
  • Downstream synthetic route of [ 72054-56-9 ]

[ 72054-56-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 69395-13-7 ]
  • [ 72054-56-9 ]
YieldReaction ConditionsOperation in experiment
91% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 5 h; To a stirred solution of 4-(2-hydroxyethyl)benzonitrile (1.0g ,6.8mmol,1eq.) in DCM (20 mL) was added CBr4 (4.5016g, 13.6mmol, 2.0 eq) and TPP (3.835g, 13.6mmol, 2.0 eq). The resulting solution was stirred at RT for 5h. Reaction was monitored TLC. Reaction was diluted with water and extracted with EtOAc. Organic layer was dried over sodium sulfate, filtered and the filtrated concentrated. The crude compound was isolated by column chromatography to get pure 4-(2-bromoethyl)benzonitrile (1.3 g, 91percent). LC-MS (method 23): Rt = 2.01 min; m/z = 210.05 (M+H+).
Reference: [1] Patent: WO2018/149986, 2018, A1, . Location in patent: Page/Page column 95
[2] Pharmazie, 1982, vol. 37, # 1, p. 13 - 16
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 1, p. 65 - 68
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1979, p. 1128 - 1132
[5] Patent: US5811459, 1998, A,
  • 2
  • [ 7617-70-1 ]
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YieldReaction ConditionsOperation in experiment
74% for 2 h; Reflux Example 8A
4-(2-Bromoethyl)benzonitrile
A solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde from Example 7A in 112.4 ml of formic acid is mixed with 12.42 g (0.18 mol) of hydroxylamine hydrochloride and heated to reflux for 2 hours.
After slow cooling to room temperature, 670 ml of water are added, and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling.
The mixture is then extracted three times with methyl tert-butyl ether.
The combined organic phases are dried over magnesium sulfate and concentrated to dryness.
The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane).
21.3 g (0.10 mol, 74percent yield) of a yellowish solid are obtained.
1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.80 (2H, d), 7.51 (2H, d), 3.77 (2H, t), 3.22 (2H, t).
MS (DCI, NH3): 227 (M+NH4+).
74% for 2 h; Reflux Example 4A; 4-(2-Bromoethyl)benzonitrile 12.42 g (0.18 mol) of hydroxylamine hydrochloride are added to a solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde in 112.4 ml of formic acid, and the mixture is heated under reflux for 2 hours. After slowly cooling to room temperature, 670 ml of water are added and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulphate and evaporated to dryness. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent yield) of a yellowish solid are obtained.1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.80 (2H, d), 7.51 (2H, d), 3.77 (2H, t), 3.22 (2H, t).MS (DCI, NH3): m/z=227 (M+NH4+).
74% for 2 h; Reflux A solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde in 112.4 ml of formic acid is mixed with 12.42 g (0.18 mol) of hydroxylamine hydrochloride and heated under reflux for 2 hours. After slow cooling to room temperature, 670 ml of water are added, and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulfate and concentrated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent of theory) of a yellowish solid are obtained.1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.80 (2H, d), 7.51 (2H, d), 3.77 (2H, t), 3.22 (2H, t).MS (DCI, NH3): 227 (M+NH4+).
Reference: [1] Patent: US2009/227640, 2009, A1, . Location in patent: Page/Page column 33
[2] Patent: US2010/29772, 2010, A1, . Location in patent: Page/Page column 15
[3] Patent: US2009/215843, 2009, A1, . Location in patent: Page/Page column 18
  • 3
  • [ 69395-13-7 ]
  • [ 72054-56-9 ]
Reference: [1] Patent: US5340831, 1994, A,
[2] Patent: US5422358, 1995, A,
  • 4
  • [ 100-27-6 ]
  • [ 72054-56-9 ]
Reference: [1] Pharmazie, 1982, vol. 37, # 1, p. 13 - 16
  • 5
  • [ 52062-92-7 ]
  • [ 72054-56-9 ]
Reference: [1] Patent: US2009/215843, 2009, A1,
  • 6
  • [ 103-63-9 ]
  • [ 72054-56-9 ]
Reference: [1] Patent: US2009/215843, 2009, A1,
  • 7
  • [ 5339-26-4 ]
  • [ 72054-56-9 ]
Reference: [1] Journal of the Chemical Society, 1942, p. 103,107
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