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[ CAS No. 616-82-0 ] {[proInfo.proName]}

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Chemical Structure| 616-82-0
Chemical Structure| 616-82-0
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Product Details of [ 616-82-0 ]

CAS No. :616-82-0 MDL No. :MFCD00007119
Formula : C7H5NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :QRYSWXFQLFLJTC-UHFFFAOYSA-N
M.W : 183.12 Pubchem ID :12033
Synonyms :

Calculated chemistry of [ 616-82-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.25
TPSA : 103.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.36
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : -0.04
Log Po/w (SILICOS-IT) : -1.38
Consensus Log Po/w : 0.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.817 mg/ml ; 0.00446 mol/l
Class : Soluble
Log S (Ali) : -3.64
Solubility : 0.0418 mg/ml ; 0.000228 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.58
Solubility : 48.5 mg/ml ; 0.265 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 616-82-0 ]

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 [ 616-82-0 ]

* 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 [ 616-82-0 ]
  • Downstream synthetic route of [ 616-82-0 ]

[ 616-82-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 616-82-0 ]
  • [ 15112-41-1 ]
Reference: [1] Patent: WO2013/97773, 2013, A1,
  • 2
  • [ 67-56-1 ]
  • [ 616-82-0 ]
  • [ 536-25-4 ]
YieldReaction ConditionsOperation in experiment
95% at 20℃; for 16 h; To a solution [OF 3-AMINO-4-HYDROXYBENZOIC] acid [(100G,] 0. [65MOL)] in methanol (1. [5L)] was added [THIONYLCHLORIDE] (233g, 1. [96MOL)] drop-wise at [5-10°C] with stirring and allowed to reflux at [65°C] for 16h. Excess methanol and thionylchloride was distilled off and crude dissolved in ethylacetate [(500ML).] The organic layer was washed with 5percent aqueous [NAHC03] solution, water, brine and dried. The solvent was removed under vacuum to give methyl-3-amino-4-hydroxybenzoate [(105G,] 95percent).
Reference: [1] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 75
  • 3
  • [ 616-82-0 ]
  • [ 536-25-4 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 17, p. 6374 - 6381
[2] Journal of Organometallic Chemistry, 2013, vol. 747, p. 189 - 194
[3] Patent: US2008/64871, 2008, A1,
  • 4
  • [ 616-82-0 ]
  • [ 1571-72-8 ]
YieldReaction ConditionsOperation in experiment
98% at 0℃; for 1 h; Reflux To tin(II) chloride (207 mg, 1.09 mmol), 12N-HCl (1.5 mL) and 4-hydroxy-3-nitrobenzoic acid (100 mg, 0.55 mmol) were added successively at 0°C, and the reaction mixture was refluxed for 1 h. After addition of water, the reaction mixture was adjusted to pH 1 using 2N NaOH. The precipitates obtained were filtered and washed with water. The filtrate was concentrated in vacuo, and methanol was added to the residue. The formed precipitate was filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using methylene chloride and methanol (5:1) as eluent to obtain compound 1 (82 mg, 98percent) as a brown solid [1H NMR (500 MHz, DMSO-d6) δ 11.30 (brs, 1 H), 9.42 (brs, 3 H), 7.79 (s, 1 H), 7.60 (d, 1 H, J = 8.0 Hz), 7.07 (d, 1 H, J = 8.0 Hz)].
98% With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; water at 0℃; for 1 h; Concentrated hydrochloric acid (12N-HCl, 1.5 mL)Tin tailored to 0 (II) chloride (tin (II) chloride, 207 mg, 1.09 mmol)After the addition to the,4-hydroxy-3-nitrobenzoic acid (100 mg, 0.55 mmol)And the mixture was stirred under reflux for 1 hour. Then,Water was added and the pH was adjusted to 1 by addition of 2N-NaOH.The resulting solid was filtered, washed with water, and the filtrate was concentrated under reduced pressure,Methanol was added and filtered again.The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride: methanol = 5: 1) to obtain Compound 57 (82 mg, 98percent) as a brown solid.
95% With palladium on activated charcoal; hydrogen In methanol at 20℃; A mixture of 4-hydroxy-3-nitrobenzoic acid (10 g, 1.0 eq) and 2 g Pd/C in 100 mL MeOH was stirred at rt under H2 (1 atm) overnight, and then filtered. The filtrate was concentrated under reduced pressure to afford the desired product (8.0 g, 95percent). :H NMR (400 MHz, DMSO-c ) δ 10.00 (brs, 1H), 7.19 (s, 1H), 7.07 (d, J = 8.4 Hz, 1H), 6.67 (d, J = 8.4 Hz, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 684 - 688
[2] Patent: KR2018/117068, 2018, A, . Location in patent: Paragraph 0084; 0283; 0286; 0288; 0289
[3] Patent: WO2013/97773, 2013, A1, . Location in patent: Paragraph 0267
[4] Chemische Berichte, 1896, vol. 29, p. 1758
[5] Zeitschrift fuer Chemie, 1866, p. 648
[6] Journal of the Chemical Society, 1935, p. 196,199
[7] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3740 - 3744
  • 5
  • [ 89-41-8 ]
  • [ 616-82-0 ]
  • [ 40757-20-8 ]
Reference: [1] Patent: US5424479, 1995, A,
  • 6
  • [ 619-57-8 ]
  • [ 616-82-0 ]
  • [ 74230-08-3 ]
  • [ 99-96-7 ]
YieldReaction ConditionsOperation in experiment
13% at 80℃; for 21 h; Inert atmosphere 4-Hydroxybenzamide (0.2743 g, 2 mmol) was dissolved in acetic acid (4 mL), and to the stirringsolution was added amyl nitrite (1.20 mL, 6 mmol). The reaction was placed under N2 atmosphere andheated to 80 °C. At specified time points (15 min., 30 min., 1 hr, 2 hr, 4 hr, 6 hr, 8 hr, 12 hr, and 24 hr)a 100 μL aliquot of the solution was syringed out of the reaction and quenched by mixing with 1 mLsolution of 5percent Et3N in MeOH. Each aliquot was then condensed and dried in vacuum before beinganalysed via 1H-NMR
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 37, p. 5153 - 5156
  • 7
  • [ 616-82-0 ]
  • [ 758684-29-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Patent: US2008/64871, 2008, A1,
  • 8
  • [ 616-82-0 ]
  • [ 934593-90-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2013, vol. 747, p. 189 - 194
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