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[ CAS No. 321-21-1 ] {[proInfo.proName]}

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Chemical Structure| 321-21-1
Chemical Structure| 321-21-1
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Product Details of [ 321-21-1 ]

CAS No. :321-21-1 MDL No. :MFCD04115880
Formula : C8H7FO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KDXOONIQRUZGSY-UHFFFAOYSA-N
M.W : 154.14 Pubchem ID :3860639
Synonyms :

Calculated chemistry of [ 321-21-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.33
TPSA : 37.3 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 2.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.7 mg/ml ; 0.00454 mol/l
Class : Soluble
Log S (Ali) : -2.33
Solubility : 0.726 mg/ml ; 0.00471 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.583 mg/ml ; 0.00378 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 321-21-1 ]

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 [ 321-21-1 ]

* 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 [ 321-21-1 ]
  • Downstream synthetic route of [ 321-21-1 ]

[ 321-21-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 321-21-1 ]
  • [ 700-85-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2644 - 2649
  • 2
  • [ 321-21-1 ]
  • [ 134-11-2 ]
  • [ 700-85-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2644 - 2649
  • 3
  • [ 321-21-1 ]
  • [ 619-04-5 ]
  • [ 700-85-6 ]
  • [ 4920-95-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2644 - 2649
  • 4
  • [ 456-22-4 ]
  • [ 598-30-1 ]
  • [ 74-88-4 ]
  • [ 403-15-6 ]
  • [ 321-21-1 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1501 - 1504
[2] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1501 - 1504
  • 5
  • [ 456-22-4 ]
  • [ 74-88-4 ]
  • [ 403-15-6 ]
  • [ 321-21-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 10, p. 1265 - 1272
  • 6
  • [ 456-22-4 ]
  • [ 594-19-4 ]
  • [ 74-88-4 ]
  • [ 403-15-6 ]
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  • [ 64436-59-5 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1501 - 1504
  • 7
  • [ 67-56-1 ]
  • [ 321-21-1 ]
  • [ 174403-69-1 ]
YieldReaction ConditionsOperation in experiment
95% at 80℃; for 3 h; Step 1.
Methyl 4-fluoro-2-methylbenzoate
A solution of 4-fluoro-2-methylbenzoic acid (50 g, 324.38 mmol) and SOCl2 (77 g, 648.76 mmol) in methanol (200 mL) was heated to reflux for 3 hours at 80° C.
Then, the mixture was concentrated in vacuo to afford methyl 4-fluoro-2-methylbenzoate as brown oil (52 g, 95percent).
1H-NMR (300 MHz, CDCl3): δ 7.92-7.98 (m, 1H), 6.88-6.95 (m, 2H), 3.90 (s, 3H), 2.61 (s, 3H)
78% at 130℃; for 1 h; Microwave irradiation Preparation 7; Preparation of methyl 4-fluoro-2-methylbenzoate; In a cylindrical quartz tube was placed 4-fluoro-2-methyl-benzoic acid (1.5 g, 9.7 mmol) in MeOH (15 ml) and 2 drops of H2SO4 cone, were added. The tube was introduced into a Smith Creator.(R). Personal chemistry microwave reactor.Microwave irradiation was carried out at 1300C for 1h until HPLC revealed the disappearance of the starting-material.The mixture was allowed to cool down and the solvent was removed under reduced pressure. The crude was diluted with DCM and washed with NaHCOssat. The organic phase was dried over anhydrous Na2SU4 and concentration of the solution gave the final compound (1.3g, 78percent) as colourless oil. 1 H-NMR (400 MHz), δ (ppm, DMSO-de): 7.91 (dd, J = 6.2, 8.7 Hz, 1H), 7.22 (dd, J = 2.6, 10.2 Hz, 1H), 7.15 (td, J =2.4, 8.4 Hz, 1H), 3.83 (s, 3H), 2.54 (s, 3H)
52% for 40 h; Heating / reflux
A solution of the compound of Example 144 (8.93 g, 57.9 mmol) and sulfuric acid (0.75 ML) in methanol (150 ML) was refluxed 40 h..
The reaction mixture was cooled in an ice bath, and the acid was neutralized to PH 7 with sodium bicarbonate..
The solution was concentrated under reduced pressure..
Diethyl ether and brine were added to the crude residue..
The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo to yield 5.1 g of the title compound (52percent). Rf=0.72 (silica gel, 5percent isopropanol/dichloromethane).
Reference: [1] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 60
[2] Patent: WO2010/69966, 2010, A1, . Location in patent: Page/Page column 78-79
[3] Patent: US6342504, 2002, B1, . Location in patent: Page column 119
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 24, p. 6707 - 6713
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[6] Patent: WO2013/79452, 2013, A1, . Location in patent: Page/Page column 159
  • 8
  • [ 321-21-1 ]
  • [ 174403-69-1 ]
YieldReaction ConditionsOperation in experiment
52% With sulfuric acid In methanol; diethyl ether Example 145
Preparation of methyl 2-methyl-4-fluorobenzoate STR221
A solution of the compound of Example 144 (8.93 g, 57.9 mmol) and sulfuric acid (0.75 mL) in methanol (150 mL) was refluxed 40 h.
The reaction mixture was cooled in an ice bath, and the acid was neutralized to pH 7 with sodium bicarbonate.
The solution was concentrated under reduced pressure.
Diethyl ether and brine were added to the crude residue.
The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo to yield 5.1 g of the title compound (52percent). Rf=0.72 (silica gel, 5percent isopropanol/dichloromethane).
Reference: [1] Patent: US6011158, 2000, A,
  • 9
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  • [ 74-88-4 ]
  • [ 174403-69-1 ]
Reference: [1] Patent: WO2004/50650, 2004, A1, . Location in patent: Page 29
  • 10
  • [ 67-56-1 ]
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  • [ 174403-69-1 ]
Reference: [1] Patent: US2016/362407, 2016, A1, . Location in patent: Paragraph 0646-0649
  • 11
  • [ 321-21-1 ]
  • [ 64695-92-7 ]
  • [ 1079991-68-6 ]
YieldReaction ConditionsOperation in experiment
60% at 0 - 20℃; for 6 h; Inert atmosphere [000146] To a stirred solution of 4-fluoro-2-methylbenzoic acid 83 (500 mg, 3.24 mmol) in concentrated sulfuric acid (2.5 mL) under inert atmosphere was added potassium nitrate (655 mg, 6.49 mmol) at 0 °C; warmed to RT and stirred for 6 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with ice water (20 mL), filtered the precipitated solid and dried in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5percent MeOH/ CH2C12 to afford compound 84 (300 mg, 60percent) as brown syrup. TLC: 10percent MeOH/ CH2C12 (R 0.3); 1H-NMR (DMSO-d6, 500 MHz): ö 13.56 (br s, 1H), 8.52 (d, J= 8.0 Hz, 1H), 7.61 (d, J 12.5 Hz, 1H), 2.63 (s, 3H).
Reference: [1] Patent: WO2015/138895, 2015, A1, . Location in patent: Paragraph 000146
[2] Patent: WO2018/53157, 2018, A1, . Location in patent: Page/Page column 146
  • 12
  • [ 321-21-1 ]
  • [ 1079991-68-6 ]
Reference: [1] Patent: EP2141150, 2010, A1, . Location in patent: Page/Page column 84
  • 13
  • [ 321-21-1 ]
  • [ 1260848-51-8 ]
Reference: [1] Patent: US2012/277224, 2012, A1,
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