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[ CAS No. 34403-48-0 ] {[proInfo.proName]}

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Chemical Structure| 34403-48-0
Chemical Structure| 34403-48-0
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Product Details of [ 34403-48-0 ]

CAS No. :34403-48-0 MDL No. :MFCD09738490
Formula : C9H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :DWXAJFNXJVIBDP-UHFFFAOYSA-N
M.W : 146.19 Pubchem ID :10606883
Synonyms :

Calculated chemistry of [ 34403-48-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.73
TPSA : 35.82 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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 1.81
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 3.54 mg/ml ; 0.0242 mol/l
Class : Very soluble
Log S (Ali) : -1.29
Solubility : 7.51 mg/ml ; 0.0514 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.31
Solubility : 0.0724 mg/ml ; 0.000495 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 34403-48-0 ]

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 [ 34403-48-0 ]

* 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 [ 34403-48-0 ]
  • Downstream synthetic route of [ 34403-48-0 ]

[ 34403-48-0 ] Synthesis Path-Upstream   1~11

  • 1
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  • [ 34403-48-0 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: for 2 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
Methylamine (350 ml of a 40percent aqueous solution, 4.06 mol) was added to a solution of 4-(bromomethyl)benzonitrile (51.3 g, 262 mmol) in EtOH (500 ml). After 2 h, the solvent was removed in vacuo and CH2Cl2 (500 ml) and aqueous saturated NaHCO3 solution (400 ml) were added. The organic phase was separated off and extracted with aqueous saturated NaCl solution (250 ml), over Na2SO4, and the solvent was removed after filtration in vacuo. The residue was taken up in 1 M HCl in Et2O (300 ml) and stirred for 30 min., then filtered off and washed with Et2O. The residue was taken up in H2O (500 ml), rendered basic with aqueous 6 M NaOH and extracted with CH2Cl2 (500 ml). The organic phase was dried over Na2SO4 and filtered off, and the solvent was removed in vacuo. Yield: 31.17 g, 81percent
37% for 20 h; INTERMEDIATE 64-[(Methylamino)methyl]benzonitrileMethylamine (40percent wt in H20, 25 mL, 322 mmol) was added to a solution of 4-(bromomethyl)benzonitrile (4.00 g, 20.4 mmol) in EtOH (40 mL) and the reaction mixture was stirred for 20 h. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography to give the title compound (1 .10 g, 37percent) as a yellow oil. LCMS: ES+ 147.1 [MH]+.
35.6 g at 20℃; To a solution of 4-(bromomethyl)benzonitrile (49 g, 1 eq.) in tetrahydrofurane (500 mL) methylamine (194 g of a 40percent solution by weight, 10 eq. ) was added. The mixture was stirred overnight at room temperature. After removing the solvent under reduced pressure, an aqueous solution of sodium chloride was added and the aqueous mixture was extracted with ethylacetate. The combined organic layer was dried with magnesium sulfate and freed from solvent. The title compound (35.6 g) was used directly without further purification.
Reference: [1] Patent: US2008/153843, 2008, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2012/101453, 2012, A1, . Location in patent: Page/Page column 41
[3] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 309 - 312
[4] Journal of Medicinal Chemistry, 1986, vol. 29, # 1, p. 40 - 44
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2882 - 2891
[6] Patent: WO2018/114393, 2018, A1, . Location in patent: Page/Page column 52
[7] Patent: WO2018/153730, 2018, A1, . Location in patent: Page/Page column 52
  • 2
  • [ 118964-95-7 ]
  • [ 34403-48-0 ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide; sodium tetrahydroborate In ethanol (ii)
Methyl-4-cyanobenzylamine
NaBH4 (4.54 g; 0.42 mol) was added in portions to an ice-cold solution of methyl-4-cyanobenzylideneimine (14.4 g; 0.1 mol; from step (i) above) in EtOH.
The solution was stirred at RT overnight and the resultant solution was quenched with HCl (2M; aq.), washed with ether (2*), made alkaline with NaOH (2M; aq.) to pH 10, and extracted with EtOAc (3*).
The organic solution was washed with water and brine, dried (Na2SO4), and concentrated.
Yield 11.4 g (78percent).
1H-NMR (300 MHz; CDCl3): δ7.92 (d, 2H); 7.76 (d, 2H); 4.82 (s+b, 5H); 4.40 (s, 2H)
Reference: [1] Synlett, 2004, # 9, p. 1484 - 1488
[2] Tetrahedron, 2005, vol. 61, # 24, p. 5725 - 5734
[3] Patent: US6265397, 2001, B1,
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 5, p. 1295 - 1301
[5] New Journal of Chemistry, 2010, vol. 34, # 12, p. 2922 - 2931
[6] Chemistry - A European Journal, 2014, vol. 20, # 52, p. 17565 - 17571
  • 3
  • [ 7487-88-9 ]
  • [ 105-07-7 ]
  • [ 34403-48-0 ]
Reference: [1] Patent: US2003/100554, 2003, A1,
  • 4
  • [ 2083-91-2 ]
  • [ 623-00-7 ]
  • [ 34403-48-0 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 28, p. 4188 - 4193
  • 5
  • [ 105-07-7 ]
  • [ 34403-48-0 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 21, p. 2571 - 2574
[2] Tetrahedron Letters, 1988, vol. 29, # 21, p. 2571 - 2574
[3] New Journal of Chemistry, 2010, vol. 34, # 12, p. 2922 - 2931
[4] Chemistry - A European Journal, 2014, vol. 20, # 52, p. 17565 - 17571
  • 6
  • [ 105-07-7 ]
  • [ 74-89-5 ]
  • [ 34403-48-0 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 12, p. 1771 - 1776
  • 7
  • [ 118964-95-7 ]
  • [ 34403-48-0 ]
  • [ 118964-96-8 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 21, p. 2571 - 2574
[2] Tetrahedron Letters, 1988, vol. 29, # 21, p. 2571 - 2574
  • 8
  • [ 118964-95-7 ]
  • [ 34403-48-0 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 21, p. 2571 - 2574
  • 9
  • [ 35525-86-1 ]
  • [ 34403-48-0 ]
  • [ 105-07-7 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 2, p. 64 - 65
[2] Journal of the Chemical Society, Chemical Communications, 1985, # 2, p. 64 - 65
  • 10
  • [ 74-89-5 ]
  • [ 874-86-2 ]
  • [ 34403-48-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1962, vol. 660, p. 60 - 73
  • 11
  • [ 17201-43-3 ]
  • [ 74-89-5 ]
  • [ 34403-48-0 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 1241,1249
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