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[ CAS No. 320-94-5 ] {[proInfo.proName]}

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Chemical Structure| 320-94-5
Chemical Structure| 320-94-5
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Product Details of [ 320-94-5 ]

CAS No. :320-94-5 MDL No. :MFCD00007142
Formula : C8H4F3NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :MYSAXQPTXWKDPQ-UHFFFAOYSA-N
M.W : 235.12 Pubchem ID :642096
Synonyms :

Calculated chemistry of [ 320-94-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.23
TPSA : 83.12 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) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 3.46
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 0.18
Consensus Log Po/w : 1.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.875 mg/ml ; 0.00372 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.22 mg/ml ; 0.000934 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.04
Solubility : 2.12 mg/ml ; 0.00902 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 320-94-5 ]

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 [ 320-94-5 ]

* 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 [ 320-94-5 ]
  • Downstream synthetic route of [ 320-94-5 ]

[ 320-94-5 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 320-94-5 ]
  • [ 121-17-5 ]
YieldReaction ConditionsOperation in experiment
20% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,47 mg of 2-nitro-4-trifluoromethylbenzoic acid and 17.5 mg of sodium chloride4 mL of dimethyl sulfoxide. The reaction was heated at 160 ° C for 24 hours in the presence of oxygen. After the reaction is complete, distilled water is added to quench the reaction, withEthyl acetate was extracted three times, each 10 mL, the combined organic phase was concentrated to give2-nitro-4-trifluoromethyl chlorobenzene9.0 mg, yield 20percent
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A, . Location in patent: Paragraph 0091
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 2
  • [ 455-24-3 ]
  • [ 320-94-5 ]
YieldReaction ConditionsOperation in experiment
48% at 20℃; for 2 h; Heating / reflux aEXAMPLE 2 a) 2-Nitro-4-trifluoromethylbenzoic Acid 11.97 g of 4 trifluoromethylbenzoic acid (63 mmol) were added slowly in portions at RT to 48 ml of HNO3 (100percent). The mixture was subsequently heated to reflux for 1 h, then cooled to RT and poured onto about 600 g of ice. The mixture was stirred for 1 h, then the precipitate was filtered off and washed with 1 l of water. The filtrate was extracted with 300 ml of CH2Cl2, and the organic phase was combined with the precipitate and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was recrystallized by dissolving in 1 l of DIP at 68° C., adding 2 l of HEP at this temperature and finally cooling the solution slowly to RT. The crystallized product was washed with 1 l of HEP and dried under reduced pressure to obtain 7.1 g (48percent), mp 136° C.-138° C.
Reference: [1] Patent: US2005/124681, 2005, A1, . Location in patent: Page/Page column 16
  • 3
  • [ 778-94-9 ]
  • [ 320-94-5 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2118 - 2122

[2] Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4636 - 4641
[3] Patent: US4781750, 1988, A,
  • 4
  • [ 109466-87-7 ]
  • [ 320-94-5 ]
Reference: [1] Organometallics, 2017, vol. 36, # 21, p. 4095 - 4098
  • 5
  • [ 455-18-5 ]
  • [ 320-94-5 ]
  • [ 116965-16-3 ]
Reference: [1] Patent: CN108558672, 2018, A, . Location in patent: Paragraph 0037; 0039; 0041; 0043; 0045; 0047; 0049-0055
  • 6
  • [ 121-17-5 ]
  • [ 320-94-5 ]
Reference: [1] Patent: US2017/369412, 2017, A1,
  • 7
  • [ 455-24-3 ]
  • [ 320-94-5 ]
  • [ 116965-16-3 ]
Reference: [1] Liebigs Annalen der Chemie, 1990, # 6, p. 569 - 579
  • 8
  • [ 320-94-5 ]
  • [ 61500-87-6 ]
Reference: [1] Patent: WO2006/116412, 2006, A2,
[2] Patent: WO2006/108591, 2006, A1,
  • 9
  • [ 320-94-5 ]
  • [ 349-03-1 ]
YieldReaction ConditionsOperation in experiment
30% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium bromide In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, and 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline47 mg of 2-nitro-4-trifluoromethylbenzoic acid and 30.9 mg of sodium bromide4 mL of dimethyl sulfoxide. Heat 160 ° C in the presence of oxygenReaction for 24 hours. After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated to give16.2 mg of 2-nitro-4-trifluoromethyl bromobenzene,The yield is 30percent.
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A, . Location in patent: Paragraph 0091
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 10
  • [ 320-94-5 ]
  • [ 41253-01-4 ]
YieldReaction ConditionsOperation in experiment
45% With copper(I) oxide; potassium phosphate; bismuth (III) nitrate pentahydrate; palladium(II) trifluoroacetate; oxygen; sodium iodide In dimethyl sulfoxide at 170℃; for 20 h; Schlenk technique In a Schlenk reaction tube equipped with a magnetic stirrer, 6.7 mg of palladium trifluoroacetate was added.Cuprous oxide 28.6mg,Potassium phosphate 6.4 mg, 4-trifluoromethyl-2-nitrobenzoic acid 47 mg,Sodium iodide 36mg,Bismuth nitrate pentahydrate 194 mg and 2 mL of dimethyl sulfoxide.The reaction was heated at 170°C for 20 hours in the presence of oxygen. After the reaction is completed, distilled water is added to quench the reaction.Extraction with ethyl acetate 3 times each 10 mL and the combined organic phases are concentrated to give 1-iodo-3-nitro-5-trifluoromethylBenzene 28.5mg, Yield 45percent
Reference: [1] Patent: CN107513020, 2017, A, . Location in patent: Paragraph 0075-0076
  • 11
  • [ 320-94-5 ]
  • [ 402-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In methanol at 20℃; for 2 h; Example 1 :; N-(6-Acetyl-2,4-dioxo-7-trifluoromethyl-l,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide; 2-Amino-4-trifluoromethyl-benzoic acid; A solution of 2-nitro-4-trifluoromethyl-benzoic acid (100 g, 425 mmol) in MeOH (600 mL) was treated with palladium on carbon (10percent) and the mixture was stirred at r.t. for 2 h under hydrogen (7 bars). The mixture was then filtered and concentrated in vacuo to give 2-amino-4-trifluoromethyl-benzoic acid (87.2 g, 425 mmol, 100percent) as a yellow solid, m.p. 172-173 0C, ESI-MS: m/z 206 [M+H]+.
99% With hydrogen In ethanol at 10 - 104℃; for 2 h; b)
2-Amino-4-trifluoromethylbenzoic Acid
250 g of 2-nitro-4-trifluoromethylbenzoic acid (1.06 mol) were dissolved in 1 l of EtOH and 7.5 g of Pd/C (5percent) were added.
The mixture was hydrogenated under 1-2.5 bar of hydrogen pressure.
During the hydrogen uptake, the temperature rose temporarily from 10° C. to 104° C. After 2 h, the hydrogen uptake was complete.
Subsequently, the catalyst was filtered off and the solvent was removed under reduced pressure to obtain 215 g (99percent) of a pale yellow solid, mp 174-176° C.
99% for 2 h; 2-Nitro-4-trifluoromethyl-benzoic acid (3.07 g, 13.0 mmol) was stirred with Pd/C under hydrogen atmosphere for 2 hrs. The reaction mixture was filtered with celite to remove Pd/C. The filterate was concentrated in vacuo. The residue was extracted with CH2Cl2 (30 ml x 3) and H2O (30 ml). The combined organic layer was dried over MgSO4 and then concentrated to yield title compound (2.66 99percent). 1H NMR (300MHz, DMSO-d&6): δ 7.82 (d, IH)5 7.02 (s, IH), 7.05(m, IH), 2.41(br, IH)
92% With hydrogen In methanol; water at 20℃; for 3 h; Methyl 2-amino-4-(trifluoromethyl)benzoate; Step 1: 2-Amino-4-(trifluoromethyl)benzoic acid; A mixture of 2-nitro-4-(trifluoromethyl)benzoic acid (646 g, 2.75 mol) and 10percent palladium on carbon (50percent in water, 71 g) in MeOH (3.6 L) was allowed to stir at rt under an atmosphere of H2 (15 psi).After 3 h, TLC (DCM:MeOH 10: 1) showed no remaining starting material. The mixture was filtered and the filtrate was concentrated to give 2-amino-4-(trifluoromethyl) benzoic acid (520 g, 92percent) as a white solid.
90% With hydrogen In methanol for 2 h; Example 2; l-(4-(Pyridin-4-yloxy)phenyl)-3-(2-(thiomoφhoIine-l,l-dioxide-4-carbonyl)-5-(trifluoromethyl)phenyl)urea; 16028O[0265] To a 100 mL flask containing 2-nitro-4-(trifluoromethyl)benzoic acid (940.5 mg,4 mmol) in 30 mL MeOH was added 100 mg of 10percent Pd/C. After flushing with hydrogen <n="55"/>three times, the reaction mixture was agitated under a hydrogen atmosphere for 2 h. The mixture was filtered through a plug of Celite, and the filtrate was concentrated to afford 2-amino-4-(trifluoromethyl)benzoic acid (740 mg, 3.6 mmol, 90percent).

Reference: [1] Patent: WO2006/108591, 2006, A1, . Location in patent: Page/Page column 10; 66
[2] Patent: US2005/124681, 2005, A1, . Location in patent: Page/Page column 16
[3] Patent: WO2009/96701, 2009, A2, . Location in patent: Page/Page column 28
[4] Journal of Medicinal Chemistry, 1996, vol. 39, # 5, p. 1172 - 1188
[5] Patent: WO2006/125555, 2006, A2, . Location in patent: Page/Page column 96
[6] Applied Organometallic Chemistry, 2018, vol. 32, # 1,
[7] European Journal of Organic Chemistry, 2012, # 11, p. 2118 - 2122
[8] Patent: WO2010/65134, 2010, A1, . Location in patent: Page/Page column 59-60
[9] Patent: WO2007/81690, 2007, A2, . Location in patent: Page/Page column 53-54

[10] Liebigs Annalen der Chemie, 1990, # 6, p. 569 - 579
[11] Journal of Medicinal Chemistry, 2003, vol. 46, # 26, p. 5834 - 5843
  • 12
  • [ 455-18-5 ]
  • [ 320-94-5 ]
  • [ 116965-16-3 ]
Reference: [1] Patent: CN108558672, 2018, A, . Location in patent: Paragraph 0037; 0039; 0041; 0043; 0045; 0047; 0049-0055
  • 13
  • [ 455-24-3 ]
  • [ 320-94-5 ]
  • [ 116965-16-3 ]
Reference: [1] Liebigs Annalen der Chemie, 1990, # 6, p. 569 - 579
  • 14
  • [ 320-94-5 ]
  • [ 186602-93-7 ]
Reference: [1] Medicinal Chemistry Research, 2000, vol. 10, # 1, p. 19 - 29
  • 15
  • [ 320-94-5 ]
  • [ 872624-52-7 ]
Reference: [1] Patent: WO2006/108591, 2006, A1,
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