Home Cart 0 Sign in  
X

[ CAS No. 392-09-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 392-09-6
Chemical Structure| 392-09-6
Chemical Structure| 392-09-6
Structure of 392-09-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 392-09-6 ]

Related Doc. of [ 392-09-6 ]

Alternatived Products of [ 392-09-6 ]

Product Details of [ 392-09-6 ]

CAS No. :392-09-6 MDL No. :MFCD08444028
Formula : C8H6FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KJCVCRCYCOWPFY-UHFFFAOYSA-N
M.W : 199.14 Pubchem ID :3013872
Synonyms :

Calculated chemistry of [ 392-09-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.5
TPSA : 72.12 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) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 0.0
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.597 mg/ml ; 0.003 mol/l
Class : Soluble
Log S (Ali) : -3.26
Solubility : 0.111 mg/ml ; 0.000556 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.14
Solubility : 1.45 mg/ml ; 0.00726 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 392-09-6 ]

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

Application In Synthesis of [ 392-09-6 ]

* 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 [ 392-09-6 ]
  • Downstream synthetic route of [ 392-09-6 ]

[ 392-09-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 67-56-1 ]
  • [ 403-24-7 ]
  • [ 392-09-6 ]
YieldReaction ConditionsOperation in experiment
98% Reflux Step 1 : To a solution of 2-fluoro-4-nitrobenzoic acid (1 g, 5.402 mmol) in MeOH was added H2SO4 (2.9 ml). The reaction mixture was refluxed overnight, and then cooled to room temperature and concentrated. The residue was diluted with EtOAc and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4 and concentrated. The crude was purified by column chromatography to afford the pure compound methyl 2-fluoro- 4-nitrobenzoate (1 .05 g, 98 percent).
Reference: [1] Patent: WO2013/68467, 2013, A1, . Location in patent: Page/Page column 57; 59; 60; 61
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 7042 - 7051
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 2, p. 337 - 343
[4] Patent: WO2004/37814, 2004, A1, . Location in patent: Page 166-167
[5] Patent: EP1810969, 2007, A1, . Location in patent: Page/Page column 41
[6] Patent: EP1905769, 2008, A1, . Location in patent: Page/Page column 60
[7] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 169 - 173
  • 2
  • [ 403-24-7 ]
  • [ 18107-18-1 ]
  • [ 392-09-6 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 1.5 h; 471a) Synthesis of Methyl 2-Fluoro-4-nitrobenzoate.To a 500ml round bottom flask, 2-fluoro-4-nitrobenzoic acid (1 1.68g, 63.1mmoles), toluene (200ml) and methanol (30ml) were added, respectively. Trimethylsillyldiazomethane (2M) in diethyl ether (38ml, 76mmoles) was then added dropwise at romm temperature over 30 minutes. The solution was then stired for lhour. The sovents were then removed under vaccum to afford a yellow solid. The residual solvent was co-evaporated with methanol (100ml) to give 12.52g of yellow solid (100percent yield). NMR lH-(DMSO)-I'-8.28 (d, IH, J=7.58Hz), 8.10-8.22 (m, 2H), 3.93 (s, 3H).
Reference: [1] Patent: WO2008/51547, 2008, A1, . Location in patent: Page/Page column 533
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 12, p. 1657 - 1661
  • 3
  • [ 186581-53-3 ]
  • [ 403-24-7 ]
  • [ 392-09-6 ]
YieldReaction ConditionsOperation in experiment
92% at 20℃; Add diazomethane (22.3 mL, 2 M in ether) to a mixture of 2-fluoro-4-nitro benzoic acid (4.14 g) and ether (50 mL). Stir at room temperature overnight. Concentrate under reduced pressure to provide (4.08 g, 92percent) of an oil.
Reference: [1] Patent: WO2004/14900, 2004, A1, . Location in patent: Page 52
  • 4
  • [ 18959-17-6 ]
  • [ 392-09-6 ]
  • [ 151504-81-3 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1993, # 11, p. 921 - 922
  • 5
  • [ 67-56-1 ]
  • [ 1427-07-2 ]
  • [ 392-09-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
  • 6
  • [ 1427-07-2 ]
  • [ 392-09-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 2, p. 337 - 343
  • 7
  • [ 403-24-7 ]
  • [ 392-09-6 ]
Reference: [1] Helvetica Chimica Acta, 1951, vol. 34, p. 1350,1354
  • 8
  • [ 392-09-6 ]
  • [ 73792-08-2 ]
YieldReaction ConditionsOperation in experiment
98% With palladium on activated charcoal; hydrogen In methanol at 23℃; for 2 h; Step 2: Methyl 2-fluoro-4-nitrobenzoate (1 .05 g, 5.273 mmol) was dissolved in MeOH. Pd/C (105 mg) was added to the resulting mixture. The reaction mixture was stirred at room temperature for 2 hours under H2. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The crude was purified by column chromatography to give pure compound methyl 4-amino-2-fluorobenzoate (870 mg, 98 percent).
89% With ammonium formate In ethanol at 95℃; for 6 h; Reflux the mixture of 2-fluoro-4-nitro-benzoic acid methyl ester [(0.] 85 g), ammonium formate (1.1 g) and [PD/C] (10percent, 0.32 g) in ethanol (20 mL) at [95C] for 6 hours. Filter over [CELITE0] and concentrate under reduced pressure to provide (0.64 g, 89percent) a gray solid.
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 7042 - 7051
[2] Patent: WO2013/68467, 2013, A1, . Location in patent: Page/Page column 57; 59; 60; 61
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 2, p. 337 - 343
[4] Patent: WO2004/14900, 2004, A1, . Location in patent: Page 52
[5] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
[6] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2991 - 3013
[7] Patent: EP1810969, 2007, A1, . Location in patent: Page/Page column 41
[8] Patent: EP1905769, 2008, A1, . Location in patent: Page/Page column 60
[9] Patent: WO2011/27106, 2011, A1, . Location in patent: Page/Page column 76
[10] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 4, p. 798 - 814
  • 9
  • [ 392-09-6 ]
  • [ 660432-43-9 ]
YieldReaction ConditionsOperation in experiment
94% at 23℃; for 4 h; Step 1 : To a stirred solution of methyl 2-fluoro-4-nitrobenzoate (10.0 g, 49.7 mmol, 1 eq.) in methanol (100 mL) was added sodium borohydride (9.40 g, 248.7 mmol, 5 eq.) at RT and stirred for 4h. The methanol was evaporated and the residue was diluted with ethyl acetate (50 mL x 2) washed with water (50 mL) and brine (50 mL). The ethyl acetate layer was dried over Na2S04, evaporated under vacuum to get (2-fluoro-4-nitrophenyl)methanol (8 g, 94percent, off-white solid; TLC system: EtOAc/PE (3:7), Rf: 0.30).
94% at 23℃; for 4 h; Step 1 : To a stirred solution of methyl 2-fluoro-4-nitrobenzoate (10.0 g, 49.7 mmol, 1 eq.) in methanol (100 mL) was added sodium borohydride (9.40 g, 248.7 mmol, 5 eq.) at RT and stirred for 4h. The methanol was evaporated and the residue was diluted with ethyl acetate (50 mL x 2) washed with water (50 mL) and brine (50 mL). The ethyl acetate layer was dried over Na2SO4, evaporated under vacuum to get (2-fluoro-4-nitrophenyl)methanol (8 g, 94percent, off-white solid; TLC system: EtOAc/PE (3:7), Rf: 0.30).
Reference: [1] Patent: WO2013/68461, 2013, A1, . Location in patent: Page/Page column 91; 124; 126
[2] Patent: WO2013/68467, 2013, A1, . Location in patent: Page/Page column 65; 66
Recommend Products
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 392-09-6 ]

Venetoclax Intermediates

Chemical Structure| 98549-88-3

[ 98549-88-3 ]

1H-Pyrrolo[2,3-b]pyridin-5-ol

Chemical Structure| 106614-28-2

[ 106614-28-2 ]

Methyl 2,4-difluorobenzoate

Chemical Structure| 105931-73-5

[ 105931-73-5 ]

4-Bromo-2-fluoro-1-iodobenzene

Chemical Structure| 1235865-77-6

[ 1235865-77-6 ]

2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid

Chemical Structure| 1235865-75-4

[ 1235865-75-4 ]

Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate

Related Functional Groups of
[ 392-09-6 ]

Fluorinated Building Blocks

Chemical Structure| 2965-22-2

[ 2965-22-2 ]

Methyl 2-fluoro-5-nitrobenzenecarboxylate

Similarity: 0.97

Chemical Structure| 924868-81-5

[ 924868-81-5 ]

Methyl 2,5-difluoro-4-nitrobenzoate

Similarity: 0.94

Chemical Structure| 946126-94-9

[ 946126-94-9 ]

Methyl 2-fluoro-3-nitrobenzoate

Similarity: 0.93

Chemical Structure| 697739-03-0

[ 697739-03-0 ]

Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Similarity: 0.90

Chemical Structure| 185629-31-6

[ 185629-31-6 ]

Methyl 3-fluoro-4-nitrobenzoate

Similarity: 0.89

Aryls

Chemical Structure| 2965-22-2

[ 2965-22-2 ]

Methyl 2-fluoro-5-nitrobenzenecarboxylate

Similarity: 0.97

Chemical Structure| 924868-81-5

[ 924868-81-5 ]

Methyl 2,5-difluoro-4-nitrobenzoate

Similarity: 0.94

Chemical Structure| 946126-94-9

[ 946126-94-9 ]

Methyl 2-fluoro-3-nitrobenzoate

Similarity: 0.93

Chemical Structure| 697739-03-0

[ 697739-03-0 ]

Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Similarity: 0.90

Chemical Structure| 185629-31-6

[ 185629-31-6 ]

Methyl 3-fluoro-4-nitrobenzoate

Similarity: 0.89

Esters

Chemical Structure| 2965-22-2

[ 2965-22-2 ]

Methyl 2-fluoro-5-nitrobenzenecarboxylate

Similarity: 0.97

Chemical Structure| 924868-81-5

[ 924868-81-5 ]

Methyl 2,5-difluoro-4-nitrobenzoate

Similarity: 0.94

Chemical Structure| 946126-94-9

[ 946126-94-9 ]

Methyl 2-fluoro-3-nitrobenzoate

Similarity: 0.93

Chemical Structure| 697739-03-0

[ 697739-03-0 ]

Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Similarity: 0.90

Chemical Structure| 185629-31-6

[ 185629-31-6 ]

Methyl 3-fluoro-4-nitrobenzoate

Similarity: 0.89

Nitroes

Chemical Structure| 2965-22-2

[ 2965-22-2 ]

Methyl 2-fluoro-5-nitrobenzenecarboxylate

Similarity: 0.97

Chemical Structure| 924868-81-5

[ 924868-81-5 ]

Methyl 2,5-difluoro-4-nitrobenzoate

Similarity: 0.94

Chemical Structure| 946126-94-9

[ 946126-94-9 ]

Methyl 2-fluoro-3-nitrobenzoate

Similarity: 0.93

Chemical Structure| 697739-03-0

[ 697739-03-0 ]

Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Similarity: 0.90

Chemical Structure| 185629-31-6

[ 185629-31-6 ]

Methyl 3-fluoro-4-nitrobenzoate

Similarity: 0.89