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[ CAS No. 19499-61-7 ] {[proInfo.proName]}

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Chemical Structure| 19499-61-7
Chemical Structure| 19499-61-7
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Product Details of [ 19499-61-7 ]

CAS No. :19499-61-7 MDL No. :MFCD04115408
Formula : C8H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NTPAPKLGADEFAM-UHFFFAOYSA-N
M.W : 166.18 Pubchem ID :409439
Synonyms :

Calculated chemistry of [ 19499-61-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.84
TPSA : 57.85 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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.16
Log Po/w (MLOGP) : 0.68
Log Po/w (SILICOS-IT) : -0.34
Consensus Log Po/w : 0.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.81 mg/ml ; 0.0109 mol/l
Class : Very soluble
Log S (Ali) : -2.28
Solubility : 0.87 mg/ml ; 0.00523 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.61
Solubility : 0.404 mg/ml ; 0.00243 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 19499-61-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19499-61-7 ]

* 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 [ 19499-61-7 ]
  • Downstream synthetic route of [ 19499-61-7 ]

[ 19499-61-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 7697-37-2 ]
  • [ 103-67-3 ]
  • [ 19499-60-6 ]
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Reference: [1] Journal of the Chemical Society, 1926, p. 2458
[2] Journal of the Chemical Society, 1925, vol. 127, p. 1810
  • 2
  • [ 99-61-6 ]
  • [ 74-89-5 ]
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YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 80℃; for 24 h; Molecular sieve; Sealed tube
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 24 h;
General procedure: The desired nitro-substituted benzaldehyde (1 eq, 13.2 mmol, 2.0 g), methylamine (40percent watersolution, 1.1 eq, 14.5 mmol, 0.95 mL) and molecular sieves (3A, 100 mg) were introduced in a screw cap vialand the mixture was heated at 80°C for 24h. After cooling to RT, the mixture was diluted with chloroform (3mL) and filtered. The solvent was removed by rotary evaporation and the crude obtained was redissolved inmethanol (30 mL) and cooled to 0 °C. NaBH4 (1.1 eq, 14.5 mmol, 550 mg) was added in three portions andthe resultant mixture allowed warming to RT and reacting for 24 h. The mixture was then quenched with aq.NH4OH 5percent (10 mL) and the solvent was concentrated by rotary evaporation. The obtained aqueous layer wasextracted with CH2Cl2 (3 x 10 mL). The combined organic extracts were dried over Na2SO4, filtered and thefiltrate was concentrated by rotary evaporation. The residue was purified by silica gel flash chromatographyor distillation under vacuum to give the title compound.
Reference: [1] Molecules, 2017, vol. 22, # 12,
[2] Patent: WO2013/140347, 2013, A1, . Location in patent: Page/Page column 48-49
[3] Patent: US2015/51257, 2015, A1, . Location in patent: Paragraph 0519-0520
  • 3
  • [ 593-51-1 ]
  • [ 99-61-6 ]
  • [ 19499-61-7 ]
YieldReaction ConditionsOperation in experiment
67% With sodium tetrahydroborate; titanium(IV)isopropoxide; triethylamine In ethanol at 20℃; for 24 h; A mixture of 3-nitrobenzaldehyde (1.50 g), methylamine hydrochloride (1.35 g), tetraisopropoxytitanium (5.90 mL) and triethylamine (2.79 mL) in ethanol (15 mL) was stirred at room temperature for 12 hrs. To the reaction mixture was added sodium borohydride (0.57 g) and the mixture was stirred at room temperature for 12 hrs. To the reaction mixture was added 2M aqueous ammonia. The resulting inorganic salt was removed by filtration and washed with dichloromethane. The organic layer was separated and the aqueous layer was extracted. with dichloromethane. The organic layers were combined and washed with 1N hydrochloric acid. The aqueous layer was basified with 2N aqueous sodium hydroxide, extracted with dichloromethane and dried (MGSO4). The solvent was evaporated to give the title compound (1.11 g, yield 67percent). 1H NMR (300 MHz, CDC13) 8 ppm: 2.47 (s, 3 H), 3.86 (s, 2 H), 7.49 (t, J = 7.8 Hz, 1 H), 7.62-7. 71 (m, 1 H), 8.06-8. 15 (m, 1 H), 8.20 (t, J = 1.7 Hz, 1 H).
Reference: [1] Patent: WO2004/46107, 2004, A1, . Location in patent: Page 188
[2] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
[3] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 16, p. 2527 - 2531
[4] Patent: WO2006/40526, 2006, A1, . Location in patent: Page/Page column 104
  • 4
  • [ 99-61-6 ]
  • [ 19499-61-7 ]
YieldReaction ConditionsOperation in experiment
27% With methylamine hydrochloride; sodium cyanoborohydride; triethylamine In methanol Example 42
Synthesis of N-(3-nitrophenylmethyl)methylamine
To a mixture of sodium cyanoborohydride (2.52 g), triethylamine (18.7 ml), methylamine hydrochloride (5.42 g) and methanol (660 ml), m-nitrobenzaldehyde (10.10 g) was added dropwise over 20 minutes at room temperature and the resulting mixture was stirred at room temperature for 20 h.
The pH of the reaction mixture was adjusted to 2 by addition of 10percent HCl and the methanol was distilled off under reduced pressure.
The residue was washed with chloroform and a 10percent aqueous potassium hydroxide solution was added to the aqueous layer for pH adjustment to 12, and the mixture was extracted with chloroform.
The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure.
The resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=95:5) to give 3.0 g of the titled compound (yield, 27percent).
1H-NMR(CDCl3) δ: 1.52(1H,brs), 2.47(3H,s), 3.87(2H,s), 7.50(1H,dd, J=7.8, 7.8 Hz), 7.68(1H,d J=7.8 Hz), 8.20(1H,d, J=7.8 Hz), 8.44(1H,s)
Reference: [1] Patent: US6534546, 2003, B1,
[2] Organic Process Research and Development, 2005, vol. 9, # 6, p. 837 - 842
[3] Organic Process Research and Development, 2005, vol. 9, # 6, p. 837 - 842
  • 5
  • [ 74-89-5 ]
  • [ 619-23-8 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1810
[2] Patent: WO2007/124898, 2007, A1, . Location in patent: Page/Page column 29-30
  • 6
  • [ 74-89-5 ]
  • [ 3958-57-4 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 1, p. 40 - 44
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2882 - 2891
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8694 - 8712
  • 7
  • [ 121004-44-2 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118
[2] Organic Process Research and Development, 2005, vol. 9, # 6, p. 837 - 842
  • 8
  • [ 103-67-3 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 2458
[2] Journal of the Chemical Society, 1925, vol. 127, p. 1810
  • 9
  • [ 100-44-7 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1810
[2] Journal of the Chemical Society, 1925, vol. 127, p. 1810
  • 10
  • [ 1576-37-0 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1810
  • 11
  • [ 3695-02-1 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1810
  • 12
  • [ 100-46-9 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1810
  • 13
  • [ 74-89-5 ]
  • [ 619-23-8 ]
  • [ 19499-61-7 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 1241,1249
  • 14
  • [ 98760-23-7 ]
  • [ 121004-44-2 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4943 - 4946
  • 15
  • [ 7697-37-2 ]
  • [ 103-67-3 ]
  • [ 19499-60-6 ]
  • [ 19499-61-7 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 2458
[2] Journal of the Chemical Society, 1925, vol. 127, p. 1810
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