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[ CAS No. 10406-25-4 ] {[proInfo.proName]}

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Chemical Structure| 10406-25-4
Chemical Structure| 10406-25-4
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Product Details of [ 10406-25-4 ]

CAS No. :10406-25-4 MDL No. :MFCD00025578
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :LFIWXXXFJFOECP-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :82608
Synonyms :

Calculated chemistry of [ 10406-25-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.83
TPSA : 49.81 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 : Yes
Log Kp (skin permeation) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 1.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.31
Solubility : 6.4 mg/ml ; 0.0485 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 11.7 mg/ml ; 0.0883 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.424 mg/ml ; 0.00321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 10406-25-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10406-25-4 ]

* 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 [ 10406-25-4 ]
  • Downstream synthetic route of [ 10406-25-4 ]

[ 10406-25-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 10406-25-4 ]
  • [ 17201-43-3 ]
Reference: [1] Patent: US6187945, 2001, B1,
  • 2
  • [ 10406-25-4 ]
  • [ 107-06-2 ]
  • [ 874-86-2 ]
Reference: [1] Patent: US6187945, 2001, B1,
  • 3
  • [ 10406-25-4 ]
  • [ 56-91-7 ]
Reference: [1] Patent: US5777158, 1998, A,
  • 4
  • [ 623-26-7 ]
  • [ 10406-25-4 ]
  • [ 539-48-0 ]
YieldReaction ConditionsOperation in experiment
92.1% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; EXAMPLE 5 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.2 molpercent and the yield of p-xylynenediamine was 92.1 molpercent.
87.7% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; EXAMPLE 2 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46percent by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.5 molpercent and the yield of p-xylynenediamine was 87.7 molpercent.
Reference: [1] Patent: EP1449825, 2004, A1, . Location in patent: Page 5
[2] Patent: EP1449825, 2004, A1, . Location in patent: Page 5
  • 5
  • [ 623-26-7 ]
  • [ 10406-25-4 ]
  • [ 539-48-0 ]
YieldReaction ConditionsOperation in experiment
88.8% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; EXAMPLE 2 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46percent by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.5 molpercent and the yield of p-xylynenediamine was 87.7 molpercent. EXAMPLE 5 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.2 molpercent and the yield of p-xylynenediamine was 92.1 molpercent.
Reference: [1] Patent: EP1449825, 2004, A1, . Location in patent: Page 5
[2] Patent: US6392083, 2002, B1, . Location in patent: Page column 5-6
[3] Patent: EP1454895, 2004, A1, . Location in patent: Page 7; 8
  • 6
  • [ 10406-25-4 ]
  • [ 874-89-5 ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate; dimethyl sulfoxide; trifluoroacetic acid; sodium nitrite In water Example 1
p-Cyanobenzylamine (26.2 g), sodium nitrite (20.8 g), and dimethyl sulfoxide (200 ml) were mixed, and the mixture was vigorously stirred at room temperature (about 20 to 30° C.).
Trifluoroacetic acid (45.6 g) was added dropwise to the mixture over a one hour period.
After completion of addition, the mixture was further allowed to react at 100° C. for one hour.
The reaction mixture was analyzed by use of high performance liquid chromatography, to thereby obtain proportions (on the mol basis) of predominant reaction products: p-cyanobenzyl alcohol:p-cyanobenzaldehyde:p-cyanobenzoic acid=72:18:10.
Dimethyl sulfoxide was removed through distillation under vacuum, and water (300 ml) was added to the residue.
Sodium carbonate was added to the thus-formed solution, to thereby adjust pH to 8.
The resultant aqueous solution was subjected to extraction with toluene (300 ml*2).
Toluene was removed through distillation under reduced pressure, and the resultant solution was subsequently distilled under vacuum, to thereby obtain 16.2 g of p-cyanobenzyl alcohol (bp. 175-178° C./1.5 kPa) (yield 61percent).
The purity of the product was 98percent.
51% With sulfuric acid; sodium nitrite In water; toluene Example 3
p-Cyanobenzylamine (13.2 g), water (54 g), and toluene (20 g) were mixed, and the mixture was stirred with cooling with ice.
Concentrated sulfuric acid (14.7 g) was added to the mixture.
Subsequently, a 20 wt percent aqueous solution (44.9 g) of sodium nitrite was added dropwise to the mixture over one hour.
The mixture was stirred at the same temperature for four hours.
For the subsequent process, the procedure of Example 1 was repeated, to thereby obtain 6.8 g of p-cyanobenzyl alcohol (yield 51percent).
The purity of the product was 98percent.
Reference: [1] Patent: US6187945, 2001, B1,
[2] Patent: US6187945, 2001, B1,
  • 7
  • [ 24424-99-5 ]
  • [ 10406-25-4 ]
  • [ 66389-80-8 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine In dichloromethane at 20℃; To a round-bottom flask equipped with a stir bar was added 17a-b (1.0 eq), Boc2O (1.1 eq), CH2Cl2 (10mL/mmol), and triethylamine (1.5 eq). The reaction mixture was stirred at room temperature overnight. The reaction was concentrated in vacuo and partitioned between ethyl ether and 1M HCl. The organic layer were separated, washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo to give a white crystalline solid. 4.2.4.2 128 tert-Butyl (4-cyanobenzyl)carbamate (18a) Yield: 93percent. MP: 114–116°C. 1H NMR (400MHz, CDCl3) δ 7.62 (d, J=7.9Hz, 2H, -ArH), 7.39 (d, J=8.5Hz, 2H, -ArH), 4.96 (s, 1H, -NH-), 4.37 (d, J=5.9Hz, 2H, -CH2-), 1.46 (s, 9H, -CH3)
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1843 - 1852
[2] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 796 - 808
[3] Bioorganic & Medicinal Chemistry Letters, 2002, vol. 12, # 4, p. 644 - 648
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3477 - 3482
[5] Patent: WO2013/138665, 2013, A1, . Location in patent: Paragraph 00095
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 1, p. 98 - 109
  • 8
  • [ 10406-25-4 ]
  • [ 15996-76-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In ethyl acetate In a 200 ml four-neck flask equipped with an agitator, a thermometer, a gas conduit, and a reflux condenser, p-cyanobenzylamine (10.0 g) obtained in Preparation Example 3 was dissolved in ethyl acetate (90.0 g). While the reactor was cooled in a water bath, hydrogen chloride gas was fed into the vapor phase of the reactor while stirring. Immediately after the introduction of hydrogen chloride, heat generation was confirmed, and a white solid was precipitated. After the reaction mixture was cooled to room temperature, the white solid was separated through filtration and dried in a desiccator under vacuum, thereby yielding 12.6 g of p-cyanobenzylamine hydrochloride (yield based on p-cyanobenzylamine: 99percent). Through high-performance liquid chromatographic analysis of the thus-obtained p-cyanobenzylamine hydrochloride, the p-cyanobenzylamine content in the hydrochloride was found to be 77 mass percent. In addition, the hydrogen chloride content in p-cyanobenzylamine hydrochloride was found to be 23 mass percent through anion chromatographic analysis. The thus-obtained p-cyanobenzylamine hydrochloride has a bulk density of 0.3 g/ml.
75% With hydrogenchloride In water In a 200 ml three-neck flask equipped with an agitator, a thermometer, and a dropping funnel, p-cyanobenzylamine hydrate (32.5 g) obtained in Preparation Example 2 and water (20.2 g) were placed. Concentrated hydrochloric acid (35 mass percent aqueous solution of hydrogen chloride, hereinafter the same solution was employed) (20.5 g) was added dropwise to the mixture through the dropping funnel under stirring, thereby forming a white solid. The white solid was separated through filtration and dried in a desiccator under vacuum, thereby yielding 24.5 g of p-cyanobenzylamine hydrochloride (yield based on p-cyanobenzylamine hydrate: 75percent).
Reference: [1] Patent: US6392083, 2002, B1, . Location in patent: Page column 6
[2] Patent: US6392083, 2002, B1, . Location in patent: Page column 7
  • 9
  • [ 10406-25-4 ]
  • [ 108468-00-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3477 - 3482
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1843 - 1852
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