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[ CAS No. 1571-08-0 ] {[proInfo.proName]}

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Chemical Structure| 1571-08-0
Chemical Structure| 1571-08-0
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Product Details of [ 1571-08-0 ]

CAS No. :1571-08-0 MDL No. :MFCD00006950
Formula : C9H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :FEIOASZZURHTHB-UHFFFAOYSA-N
M.W : 164.16 Pubchem ID :15294
Synonyms :

Calculated chemistry of [ 1571-08-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.11
TPSA : 43.37 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) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 1.49
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 1.28
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.97
Solubility : 1.77 mg/ml ; 0.0108 mol/l
Class : Very soluble
Log S (Ali) : -2.01
Solubility : 1.61 mg/ml ; 0.00981 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.634 mg/ml ; 0.00386 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.04

Safety of [ 1571-08-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1571-08-0 ]

* 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 [ 1571-08-0 ]
  • Downstream synthetic route of [ 1571-08-0 ]

[ 1571-08-0 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 67-56-1 ]
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  • [ 1571-08-0 ]
Reference: [1] Chemistry Letters, 1980, p. 483 - 486
  • 2
  • [ 1571-08-0 ]
  • [ 7377-26-6 ]
YieldReaction ConditionsOperation in experiment
90% at 60℃; for 10 h; Melt [Example 1] 75percent methyl-4-formylbenzoate (methyl-4-formylbenzoate 16. 4g) was melted at 60°C, and 1.5 molar equivalent of chlorine gas (C12) was added thereto while bubbling for 10 hours to obtain methyl-4-chloroformylbenzoate with the yield of 90percent. 19.8g of methyl-4-chloroformylbenzoate dissolved in 80g of toluene at 60°C was dropwisely added into 10percent aqueous ammonia for 2 hours, which includes 10 molar equivalent of ammonia with respect to methyl-4- chloroformylbenzoate. In this reaction, the reaction temperature was maintained at 5 to 20°C. Then, cooling of the reactant was stopped to increase the temperature of the reactant to room temperature. The reactant was filtered to obtain white crystalline methyl-4-carbamoylbenzoate with the yield of 98percent and the purity of 95percent. 1N aqueous sodium hydroxide solution including 5 molar equivalent of sodium hydroxide with respect to methyl-4-carbamoylbenzoate is cooled to 0°C, and 17. 9g of methyl-4-carbamoylbenzoate was added thereto. While maintaining the temperature of the reactant at 0 to 10°C, 10percent aqueous NaOCI solution including 1.05 molar equivalent of NaOCI was added into the reactant for 30 minutes, and the reaction was continued for 2 hours. Then, the temperature of the reactant was increased to 50°C, and maintained for 1 hour. By adding aqueous NaOH, the pH of the reactant was adjusted to 4, and solid target compound was precipitated. By filtering the reactant, the target compound, p- aminobenzoic acid was obtained with the yield of 95percent.
Reference: [1] Patent: WO2003/72534, 2003, A1, . Location in patent: Page/Page column 9
[2] Medicinal Chemistry Research, 2013, vol. 22, # 8, p. 3857 - 3862
  • 3
  • [ 1571-08-0 ]
  • [ 56-91-7 ]
Reference: [1] Patent: US2012/296114, 2012, A1,
[2] Patent: EP2524909, 2012, A2,
  • 4
  • [ 1571-08-0 ]
  • [ 34040-64-7 ]
Reference: [1] Organic Preparations and Procedures International, 2007, vol. 39, # 4, p. 412 - 415
  • 5
  • [ 1571-08-0 ]
  • [ 34040-64-7 ]
  • [ 106491-50-3 ]
Reference: [1] Canadian Journal of Chemistry, 1986, vol. 64, p. 2342 - 2347
[2] Canadian Journal of Chemistry, 1986, vol. 64, p. 2342 - 2347
  • 6
  • [ 1571-08-0 ]
  • [ 18469-52-8 ]
Reference: [1] Science, 2017, vol. 358, # 6361, p. 326 - 332
  • 7
  • [ 66534-32-5 ]
  • [ 1571-08-0 ]
  • [ 30611-21-3 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 12, p. 2515 - 2517
  • 8
  • [ 1571-08-0 ]
  • [ 30611-21-3 ]
Reference: [1] Patent: WO2018/140338, 2018, A1,
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 21, p. 5701 - 5710
  • 9
  • [ 62-53-3 ]
  • [ 1571-08-0 ]
  • [ 3814-10-6 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 11993 - 11998
  • 10
  • [ 99-75-2 ]
  • [ 7356-11-8 ]
  • [ 1571-08-0 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 24 - 32[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 1, p. 30 - 39
  • 11
  • [ 1571-08-0 ]
  • [ 19675-63-9 ]
Reference: [1] Heterocycles, 1995, vol. 41, # 8, p. 1659 - 1666
  • 12
  • [ 1571-08-0 ]
  • [ 90484-53-0 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
  • 13
  • [ 1571-08-0 ]
  • [ 24589-98-8 ]
  • [ 42137-51-9 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 11, p. 3889 - 3896
  • 14
  • [ 2031-62-1 ]
  • [ 1571-08-0 ]
  • [ 146781-28-4 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With dicarbonyl(pentamethylcyclopentadienyl)(4-methoxyphenyl)iron In dichloromethane for 4 h; Inert atmosphere; Irradiation; Schlenk technique
Stage #2: With sodium hydroxide In methanol; waterSchlenk technique; Inert atmosphere
General procedure: In a Schlenk tube under 1 atm of argon, a solution of the substrate (2 mmol, 1 equiv), the precatalyst (0.04 mmol, 0.02 equiv), and the silane (3 mmol, 1.5 equiv) in methylene chloride (15 mL) was irradiated for 4h. After removal of the solvent, methanol (5 mL) and aqueous NaOH solution (2.5 M, 5 mL) were added and the resulting suspension was stirred overnight. Neutralization with aqueous HCl solution (2 M, 30 mL) and brine (20 mL) followed by standard workup gave the desired products as pure yellow oils.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 37, p. 5015 - 5018
  • 15
  • [ 1571-08-0 ]
  • [ 54274-80-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2004, vol. 689, # 3, p. 639 - 646
  • 16
  • [ 1571-08-0 ]
  • [ 62642-62-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 179 - 190
  • 17
  • [ 1571-08-0 ]
  • [ 106261-48-7 ]
Reference: [1] Patent: WO2011/8788, 2011, A1,
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 179 - 190
  • 18
  • [ 1122-62-9 ]
  • [ 1571-08-0 ]
  • [ 158014-74-5 ]
YieldReaction ConditionsOperation in experiment
50% With ammonia; sodium hydroxide In ethanol; water at 20℃; for 17 h; Round bottom flask 4-methoxycarbonyl benzaldehyde (1.0g, 6.1mmol) and 2-acetyl pyridine (1.37ml, 12.2mmol) were dissolved in 25ml of ethanol.Then 30percent NH3were placed in a round flask, that the solution (1ml) and NaOH (0.488g, 12.2mmol) was dissolved in a minimal amount of water.Put the clear liquid solution of NaOH runners ttuieotgo is light yellow, and after about an hour and caught the red.In about 17 hours at room temperature, open the entrance to the round bottom flask and stirred haenotgo allow air to enter.Over time, the precipitate produced was more yellow.After the reaction was terminated, and then dissolved into water (50ml) and neutralized with HCl.The precipitate was filtered out and washed with water by filtration.And placed in 50ml of ethanol was refluxed for 1 hour and filtered and dried under vacuum (yield: 50percent).
Reference: [1] Patent: KR101489185, 2015, B1, . Location in patent: Paragraph 0268-0271
[2] Dalton Transactions, 2007, # 38, p. 4323 - 4332
  • 19
  • [ 1571-08-0 ]
  • [ 158014-74-5 ]
Reference: [1] New Journal of Chemistry, 2018, vol. 42, # 11, p. 9317 - 9323
  • 20
  • [ 1571-08-0 ]
  • [ 74733-26-9 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
  • 21
  • [ 1571-08-0 ]
  • [ 155405-80-4 ]
Reference: [1] Patent: WO2011/64256, 2011, A1,
  • 22
  • [ 1571-08-0 ]
  • [ 894187-61-2 ]
Reference: [1] Patent: WO2013/155338, 2013, A2,
[2] Patent: US2015/329503, 2015, A1,
[3] Patent: US2015/329503, 2015, A1,
  • 23
  • [ 1571-08-0 ]
  • [ 1403783-31-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9891 - 9899
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