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[ CAS No. 18595-12-5 ] {[proInfo.proName]}

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Chemical Structure| 18595-12-5
Chemical Structure| 18595-12-5
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Product Details of [ 18595-12-5 ]

CAS No. :18595-12-5 MDL No. :MFCD08752568
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JNPZKGOLYSCSEL-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :15049977
Synonyms :

Calculated chemistry of [ 18595-12-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
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 : 47.09
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 2.07
Log Po/w (WLOGP) : 1.37
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.44
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.648 mg/ml ; 0.00392 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.263 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.531 mg/ml ; 0.00321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 18595-12-5 ]

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

Application In Synthesis of [ 18595-12-5 ]

* 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 [ 18595-12-5 ]
  • Downstream synthetic route of [ 18595-12-5 ]

[ 18595-12-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 77324-87-9 ]
  • [ 18595-12-5 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol for 20 h; Methyl 2-methyl-5-nitrobenzoate (5.0 g, 25.6 mmol) was dissolved in [ETOH] with Raney nickel under a 35 psi atmosphere of H2. The reaction was stirred for 20 h, then filtered through Celite washed with [MEOH] and concentrated in vacuo to afford 4.2 g (100percent) of methyl [5-AMINO-2-METHYLBENZOATE.]
99% With hydrogen In ethyl acetate at 23℃; for 16 h; 5-Amino-2-methylbenzoic Acid Methyl Ester (41). To a solution of nitro 35 (635 mg, 3.3 mmol) in EtOAc (10 mL) was added 10percent Pd-C (30 mg) and it was allowed to stir for 16 h at 23° C. under H2 atmosphere. The reaction was filtered through a celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to furnish compound 41 (536 mg, >99percent) as a colorless oil, Rf=0.57 (hexane:EtOAc=1:1). 1HNMR(400 MHz, CDCl3): δ 7.21 (d, 1H, J=2.5 Hz), 6.97 (d, 1H, J=8.1 Hz), 6.69 (dd, 1H, J=2.5 and 8.1 Hz), 3.82 (s, 3H), 3.64 (s, 2H), 2.43 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 168.1, 144.1, 132.3, 129.8, 129.5, 118.8, 116.7, 51.6, 20.6. MS (EI): m/z 165.20 [M]+. HRMS (EI), calcd for C9H11NO2165.0790, found [M]+ 165.0787.
86% With hydrogen In methanol at 80℃; for 14 h; 6.3 g (32 mmol) of methyl 2-methyl-5-nitrobenzoate are dissolved in 80 ml of anhydrous methanol and then transferred into a steel reactor. The mixture is degassed with nitrogen and then 630 mg of Pd/C (5percent) are added. The reaction medium is then subjected to a hydrogen pressure of 4 bar and to a temperature of 80° C. for 14 hours and then brought to ambient pressure and temperature and filtered. The residue, after evaporation, is purified by chromatography on a silica column. A brown oil is obtained (m=4.6 g, Y=86percent).
860 mg With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 3 h; 153.1
5-Amino-2-methyl-benzoic acid methyl ester
To a solution of 2-methyl-5-nitrobenzoic acid methyl ester (1015 mg) in EtOH (33 mL) was added 10percent palladium on charcoal (175 mg) and the reaction mixture was stirred under an atmospheric pressure of hydrogen for 3 h at RT.
It was filtered over a pad of celite and the filtrate was concentrated in vacuo to give 860 mg of the titled compound as an orange oil.
1H NMR (CDCl3) δ: 7.27 (d, J=2.6 Hz, 1H), 7.05 (d, J=8.1 Hz, 1H), 6.77 (dd, J1=8.1 Hz, J2=2.6 Hz, 1H), 3.89 (s, 3H), 3.64 (s, 2H), 2.49 (s, 3H)

Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12074 - 12075
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
[3] Patent: WO2004/18414, 2004, A2, . Location in patent: Page 110
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5228 - 5240
[5] Patent: US2011/269834, 2011, A1, . Location in patent: Page/Page column 29
[6] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 635 - 654
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 634 - 639
[8] Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 2176 - 2186
[9] Tetrahedron, 2008, vol. 64, # 14, p. 3253 - 3267
[10] Patent: US6689922, 2004, B1, . Location in patent: Page column 86
[11] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[12] Patent: US2005/43385, 2005, A1, . Location in patent: Page/Page column 14
[13] Patent: WO2006/63805, 2006, A1, . Location in patent: Page/Page column 76
[14] Patent: WO2007/71955, 2007, A1, . Location in patent: Page/Page column 52
[15] Patent: US2009/239859, 2009, A1, . Location in patent: Page/Page column 298
[16] Patent: WO2005/9940, 2005, A1, . Location in patent: Page 175
[17] Patent: US2010/81643, 2010, A1, . Location in patent: Page/Page column 37
[18] Patent: WO2010/47982, 2010, A1, . Location in patent: Page/Page column 78
[19] Patent: WO2012/114268, 2012, A1, . Location in patent: Page/Page column 134
[20] Patent: US2014/73651, 2014, A1, . Location in patent: Paragraph 0984; 0985
  • 2
  • [ 1975-52-6 ]
  • [ 18595-12-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
[2] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12074 - 12075
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 635 - 654
[4] Patent: US2011/269834, 2011, A1,
  • 3
  • [ 18583-89-6 ]
  • [ 83140-97-0 ]
  • [ 18595-12-5 ]
Reference: [1] Patent: US5234946, 1993, A,
  • 4
  • [ 18595-12-5 ]
  • [ 421551-82-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
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