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Product Details of [ 2252-51-9 ]

CAS No. :2252-51-9 MDL No. :MFCD00010615
Formula : C7H4ClFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GRPWQLDSGNZEQE-UHFFFAOYSA-N
M.W : 174.56 Pubchem ID :75259
Synonyms :

Calculated chemistry of [ 2252-51-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.37
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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.34
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 2.6
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 2.28
Consensus Log Po/w : 2.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.59
Solubility : 0.45 mg/ml ; 0.00258 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.522 mg/ml ; 0.00299 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.379 mg/ml ; 0.00217 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 2252-51-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2252-51-9 ]

* 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 [ 2252-51-9 ]
  • Downstream synthetic route of [ 2252-51-9 ]

[ 2252-51-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 201230-82-2 ]
  • [ 101335-11-9 ]
  • [ 2252-51-9 ]
YieldReaction ConditionsOperation in experiment
89% With water; palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane at 110℃; for 2 h; Flow reactor General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 °C, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit® column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 × 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.
Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1503 - 1511
  • 2
  • [ 2457-76-3 ]
  • [ 2252-51-9 ]
YieldReaction ConditionsOperation in experiment
97.5%
Stage #1: With dihydrogen peroxide In water at 40 - 50℃; for 3 h; Ionic liquid
Stage #2: With potassium fluoride In water at 40 - 50℃; for 3 h;
To a four-necked flask was charged with 4-amino-2-chlorobenzoic acid 0.56mol, ionic liquids and water 3mol 50mol, warmed to 40-50 ° C, was added 3mol hydrogen peroxide, the reaction 3h, continue to add potassium fluoride 5mol and Tungstophoric ammonium salt 0.08mol, stirred 3h, filtered, and the filtrate solvent was removed under reduced pressure and dried to give 2-chloro-4-fluoro-benzoic acid, yield 97.5percent.
Reference: [1] Patent: CN105732357, 2016, A, . Location in patent: Paragraph 0041-0042
  • 3
  • [ 84194-36-5 ]
  • [ 2252-51-9 ]
YieldReaction ConditionsOperation in experiment
90.8% With hydrogenchloride; sodium chlorite In water; acetonitrile at 0 - 80℃; for 1 h; Compound 17 (1 g, 6.31 mmol) and CH3CN (20 ml) were added to a 100 ml three-necked flask and stirred at 0°C until dissolved.Further, 5 ml of an aqueous solution of NaClO2 (1.71 g, 18.92 mmol) was added thereto, the mixture was further stirred and mixed, and 5 ml of an aqueous solution of HCl (3.31 ml, 25.23 mmol) was slowly added dropwise.After the addition was completed, the mixture was stirred at 0°C for 0.5 h. The reaction flask was transferred to a silicone oil bath, and the temperature was raised to 80°C and stirred for 0.5 h. The reaction was completed by TLC. The acetonitrile in the reaction solution was spin-dried and diluted with 10 ml of H2O.Adjust pH to 2 with 6N HCl, extract with ethyl acetate/water, dissolve the product in the organic phase, separate the liquid, collect the organic phase, dry with anhydrous Na2SO4, and spin dry the organic solvent.The crude product was obtained, purified by column chromatography, and eluted with petroleum ether:ethyl acetate=2:1 to give compound 21 as a white solid, 1.0 g, yield: 90.8percent.
Reference: [1] Patent: CN107556289, 2018, A, . Location in patent: Paragraph 0099; 0101; 0102; 0103
  • 4
  • [ 452-73-3 ]
  • [ 2252-51-9 ]
Reference: [1] Synthesis, 1987, # 10, p. 883 - 887
[2] Zhurnal Obshchei Khimii, 1941, vol. 11, p. 243,246[3] Chem.Abstr., 1941, p. 7965
  • 5
  • [ 157165-30-5 ]
  • [ 2252-51-9 ]
Reference: [1] Patent: US5481032, 1996, A,
  • 6
  • [ 625-98-9 ]
  • [ 2252-51-9 ]
Reference: [1] Journal of the Chemical Society, 1963, p. 2784 - 2787
  • 7
  • [ 700-35-6 ]
  • [ 2252-51-9 ]
Reference: [1] Journal of the Chemical Society, 1963, p. 2784 - 2787
  • 8
  • [ 2252-51-9 ]
  • [ 700-35-6 ]
Reference: [1] Patent: EP3333157, 2018, A1,
  • 9
  • [ 2252-51-9 ]
  • [ 124-41-4 ]
  • [ 21971-21-1 ]
Reference: [1] Patent: WO2005/30217, 2005, A1, . Location in patent: Page/Page column 21
  • 10
  • [ 2252-51-9 ]
  • [ 4793-24-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3756 - 3767
  • 11
  • [ 2252-51-9 ]
  • [ 114776-15-7 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 10℃; for 2 h; Compound 3-1 (9.3 g, 53.3 mmol) was dissolved in 100 ml of concentrated sulfuric acid,Nitric acid (3.5 g, 44.5 mmol) was added dropwise in an ice-water bath,The reaction was carried out at 0-10 ° C for 2 hours. After completion of the reaction, 0.5 L of ice water was added to the system,Extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column.Compound 3-2 (11.7 g, 99.0percent) was obtained.
97.1%
Stage #1: With zirconium chloride; sulfuric acid; cobalt(II) chloride In ethanol; water at 25℃; for 1 h;
Stage #2: With nitric acid In ethanol; water at -5 - 8℃; for 1 h;
50 grams of concentrated sulfuric acid was charged into the reaction flask, 0.8 grams of the catalyst prepared in Example 1,10 g of 2-chloro-4-fluorobenzoic acid was added in portions and stirred at 25 ° C for 1 hour. The mixture was cooled to 0 ° C in an ice bath and 5 g of fuming nitric acid was added dropwise to control the reaction temperature at -5 to 8 ° C. 5 ~ 8 for 1 hour, the control 2-chloro-4-fluorobenzoic acid content of less than 0.5percent; the reaction was stirred slowly poured into 80 grams of crushed ice, filtered, the filter cake was rinsed with 30 grams of ice water , 65 blast drying, have white solid products12.0 g of 2-chloro-4-fluoro-5-nitrobenzoic acid was obtained in a yield of 97.1percent and a purity of 97.2percent. The weight content of the isomeric compound of formula (II) was 1.1percent.
58.1% With nitric acid In sulfuric acid Example 1
Preparation of 2-Chloro-4-fluoro-5-nitrobenzoic Acid
A solution of 2-chloro-4-fluorobenzoic acid (24.4 g, 0.142 mol) in 150 ml of concentrated sulfuric acid at 0° C. was treated dropwise with 90percent nitric acid (13.2 ml, 20 mol percent, 0.284 mol) over a 10 min. period at 10° C., stirred for 2.5 hours at 0 to 10° C., poured onto one liter of ice.
The white solid was filtered.
The filtercake was air-dried and recrystallized from ethyl acetate/heptane to afford the title compound as off-white needles. Yield: 18.0 g (58.1percent); identified by NMR spectral analysis.
Reference: [1] Patent: CN106866684, 2017, A, . Location in patent: Paragraph 0131-0132; 0204-0205
[2] Patent: CN106905161, 2017, A, . Location in patent: Paragraph 0014; 0015; 0016; 0017
[3] Farmaco, 2004, vol. 59, # 6, p. 463 - 471
[4] Synthesis, 1987, # 10, p. 883 - 887
[5] Patent: US2002/45550, 2002, A1,
[6] Patent: US6090753, 2000, A,
[7] Patent: US5700761, 1997, A,
[8] Patent: EP863142, 1998, A1,
[9] Patent: US6348628, 2002, B1, . Location in patent: Page column 60-61
[10] Patent: WO2007/95124, 2007, A2, . Location in patent: Page/Page column 54-55
[11] Patent: WO2008/28617, 2008, A1, . Location in patent: Page/Page column 58
[12] Patent: EP2511273, 2012, A1, . Location in patent: Page/Page column 50
[13] Patent: WO2012/140243, 2012, A1, . Location in patent: Page/Page column 69
[14] Patent: WO2013/106409, 2013, A1, . Location in patent: Page/Page column 56
  • 12
  • [ 67-56-1 ]
  • [ 2252-51-9 ]
  • [ 85953-29-3 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; for 24 h; A mixture of 2-chloro-4-fluorobenzoic acid (6.5 g, 37 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (14.0 mL, 111 mmol), stirred 24h at room temperature and evaporated. The residue was dissolved in dichloromethane, washed with sodium bicarbonate, dried (sodium sulfate) and evaporated to provide 2-chloro-4-fluoro-benzoic acid methyl ester (7.01 g, 99percent yield) as a pale yellow oil. 1H-NMR (CDCl3, 500 MHz) 7.93 (m, 1H), 7.22 (m, 1H), 7.06 (m, 1H), 3.95 (s, 3H) ppm; MS (FIA) 189.1 (M+H); HPLC (Method A) 3.37 min.
92% at 60℃; for 10 h; General procedure: To a mixture of the appropriate substituted benzoic acid (8.6 mmol) in methanol (10 mL) was added sulfuric acid (0.5 mL),and the mixture was heated overnight at 60 °C. The reaction was then allowed to cool to room temperature, the solvent was reduced by evaporation, and the residue was diluted in cold water and neutralized with sodium hydrogen carbonate solution. The aqueous solution was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give the title compound as oil.
Reference: [1] Patent: WO2004/46120, 2004, A2, . Location in patent: Page 175; 176
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9524 - 9535
[3] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 195 - 208
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3130 - 3141
  • 13
  • [ 2252-51-9 ]
  • [ 74-88-4 ]
  • [ 85953-29-3 ]
Reference: [1] Patent: JP2015/54844, 2015, A, . Location in patent: Paragraph 0115-0117
  • 14
  • [ 2252-51-9 ]
  • [ 264927-52-8 ]
YieldReaction ConditionsOperation in experiment
99% With sodium iodate; iodine In sulfuric acid at 20℃; for 8 h; A mixture of 2-chloro-4-fluorobenzoic acid 4 (4.000 g, 22.91 mmol), NaIO3 (0.906 g, 4.58 mmol) and I2 (2.037 g, 8.02 mmol) in conc. H2SO4 (40 mL) was stirred at room temperature for 8 h. Chilled water (100 mL) was added to quench the reaction. The resulting solid was filtered, washed with H2O, dried at 50 °C in vacuum to give the white solid 3 (6.824 g, 99percent yield). Mp 124-126 °C; IR (neat): 1700, 1580, 1558, 1400, 1348, 1298, 1258 cm-1; 1H NMR (500 MHz, CD3OD): δ=8.33 (d, J=7.0 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H); 13C NMR (125 MHz, CD3OD): δ=164.9, 163.3 (d, J=250.0 Hz), 142.0 (d, J=3.7 Hz), 135.1 (d, J=10.0 Hz), 128.4, 117.9 (d, J=28.7 Hz), 78.1 (d, J=26.2 Hz); 19F NMR (470 MHz, CD3OD): δ=-89.5; HRMS (EI) m/z [M]+ calcd for C7H3ClFIO2: 299.8850; found: 299.8855.
Reference: [1] Tetrahedron, 2016, vol. 72, # 39, p. 5880 - 5885
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