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[ CAS No. 437-81-0 ] {[proInfo.proName]}

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Chemical Structure| 437-81-0
Chemical Structure| 437-81-0
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Product Details of [ 437-81-0 ]

CAS No. :437-81-0 MDL No. :MFCD00010293
Formula : C7H4F2O Boiling Point : -
Linear Structure Formula :- InChI Key :SOWRUJSGHKNOKN-UHFFFAOYSA-N
M.W :142.10 Pubchem ID :136284
Synonyms :

Calculated chemistry of [ 437-81-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 31.75
TPSA : 17.07 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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 2.32
Log Po/w (SILICOS-IT) : 2.82
Consensus Log Po/w : 2.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.14 mg/ml ; 0.00805 mol/l
Class : Soluble
Log S (Ali) : -1.55
Solubility : 4.01 mg/ml ; 0.0282 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.88
Solubility : 0.188 mg/ml ; 0.00132 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 437-81-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 437-81-0 ]

* 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 [ 437-81-0 ]
  • Downstream synthetic route of [ 437-81-0 ]

[ 437-81-0 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 437-81-0 ]
  • [ 341-23-1 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 6331 - 6334
[2] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8166 - 8172
  • 2
  • [ 83-38-5 ]
  • [ 437-81-0 ]
YieldReaction ConditionsOperation in experiment
77% With potassium fluoride; tetraphenylphosphonium bromide In sulfolane at 100 - 180℃; for 2 h; Inert atmosphere 34.8 g (0.6 mo) KF is dissolved in 250 m sulfolan under nitrogen for 2h at 100°C. By azeotropic distiNation water is removed. 20 g (0,11 mo) 26-dichlorobenzadehyde and 2.8 g (6.68 mmo) tetrapheny phosphoniumbromide are given to the water-free mixture and heated overnight to 180°C. The resu[ting dark so’ution is fi[tered, the solid washed with ethy’ acetate and the ‘ow-boNing components removed by water pressure evaporation. By vacuum dsUNation (24 mbar, 85-86°C) the color’ess product is obtained, yield 77percent
Reference: [1] Patent: WO2016/102207, 2016, A1, . Location in patent: Page/Page column 32
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Chemistry Letters, 1988, # 9, p. 1355 - 1358
[4] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2720 - 2725
[5] Patent: US6103659, 2000, A,
[6] Patent: US6103659, 2000, A,
[7] Patent: US6103659, 2000, A,
  • 3
  • [ 1897-52-5 ]
  • [ 437-81-0 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid; hydrogen In methanol at 35 - 70℃; for 3 h; Inert atmosphere A stirring bar was placed in a pressurized container, and 5.0 g of methanol was charged, 1.5 g of sulfuric acid (95percent) was added dropwise, Further, 5percent rhodium carbon (hydrated product) was converted to dry weight 18 mg was charged. The container was hermetically sealed, pressurized nitrogen substitution, pressurized hydrogen replacement was carried out. Under a hydrogen atmosphere, at a pressure of 0.3 MPa in a pressurized container at 35 ° C. , And the resulting mixture was stirred for 1 hour. After cooling the obtained mixture to room temperature, The interior of the container was pressurized with nitrogen. To the resulting mixture, 1.0 g of 2,6-difluorobenzonitrile was added. Pressurized nitrogen substitution and pressurized hydrogen replacement inside the container, and at 70 ° C., Pressure in pressurized container 0. 3 MPa to 0.14 MPa, The resulting mixture was stirred for 3 hours. The resulting mixture was cooled to room temperature, filtered, And washed with 15 mL of methanol to obtain 15.8 g of a solution. 8.1 g of the obtained solution was concentrated to obtain 2.7 g of a solution. To the resulting solution, 0.1 g of water and 3.0 g of methanol were added and concentrated, 2.7 g of a solution containing 2,6-difluorobenzaldehyde was obtained. The yield of 2,6-difluorobenzaldehyde was 85percent.
Reference: [1] Patent: JP2015/214503, 2015, A, . Location in patent: Paragraph 0072
  • 4
  • [ 372-18-9 ]
  • [ 109-94-4 ]
  • [ 437-81-0 ]
  • [ 19064-14-3 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In hexane at -78 - 20℃; for 16 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 5
  • [ 67-56-1 ]
  • [ 372-18-9 ]
  • [ 68-12-2 ]
  • [ 437-81-0 ]
  • [ 13671-00-6 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 6
  • [ 372-18-9 ]
  • [ 93-61-8 ]
  • [ 437-81-0 ]
YieldReaction ConditionsOperation in experiment
58% With n-butyllithium; sulfuric acid In tetrahydrofuran; hexane PREPARATION 14
2,6-Difluorobenzaldehyde
1,3-Difluorobenzene (25 g., 0.22 mole) was dissolved in 150 ml. of tetrahydrofuran and cooled to -50° C.
Butyl lithium (99 ml. of 2.3 M in hexane, 0.228 mole) was added over 20 minutes, maintaining the temperature at -50° C.
After 1.5 hours of stirring at the same temperature, N-methylformanilide (29.7 g., 0.22 mole) in 50 ml. of tetrahydrofuran was added over 20 minutes at -50° C.
After an additional 1.5 hours of stirring at -50° C., the reaction mixture was poured slowly into 1 liter of cold 1 N sulfuric acid, and extracted with three portions of ether.
The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil.
The oil was distilled.
Middle cuts were combined to yield 2,6-difluorobenzaldehyde (18.2 g., 58percent; b.p. 72°-74°/12 mm.).
Reference: [1] Patent: US4367234, 1983, A,
[2] Journal of Medicinal Chemistry, 1968, vol. 11, # 4, p. 814 - 819
  • 7
  • [ 372-18-9 ]
  • [ 68-12-2 ]
  • [ 437-81-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4575 - 4579
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 2998 - 3001
[3] Tetrahedron Letters, 2013, vol. 54, # 45, p. 6053 - 6056
  • 8
  • [ 443-84-5 ]
  • [ 437-81-0 ]
YieldReaction ConditionsOperation in experiment
30.2% at 130℃; for 0.5 h; (2) 6.06 g of cobalt acetate and 6.06 g of sodium molybdate were respectively dissolved in 200 ml of 2,6-difluorotoluene and 200 ml of acetic acid Into a mixed solution, where n (cobalt acetate): n (2,6-difluorotoluene) = 0.015: 1, 6.06 g of sodium bromide was dissolved in 25percent of H2O2 Into H2O2-acetic acid solution, when n (sodium bromide): n (2,6-difluorotoluene) = 0.015: 1,2,6-difluorotoluene-acetic acid solution with And H2O2-acetic acid solution were injected into the continuous heat transfer tube through a constant current pump at flow rates of 5.56 ml / min and 11.11 ml / min, respectively In the reactor, n (H2O2): n (2,6-difluorotoluene) = 2: 1, using the microchannel reactor in Figure 2, the reaction temperature is controlled at 130 , dwell time 1800s. The outlet was cooled at 0 ° C and the reaction quenched with difluoromethane. After GC analysis, 2,6-difluorotoluene The conversion was 45.1percent and the yield of 2,6-difluorobenzaldehyde was 30.2percent.
Reference: [1] Patent: CN106748681, 2017, A, . Location in patent: Paragraph 0026; 0028; 0030; 0032; 0034; 0036; 0038; 0040
[2] Kogyo Kagaku Zasshi, 1956, vol. 59, p. 1160[3] Chem.Abstr., 1958, p. 13265
  • 9
  • [ 387-45-1 ]
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Reference: [1] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[2] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[3] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[4] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[5] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[6] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[7] Patent: WO2003/101926, 2003, A1, . Location in patent: Page 18, 19
[8] Patent: US6465643, 2002, B1,
[9] Patent: WO2004/74296, 2004, A2, . Location in patent: Page/Page column 12-13
[10] Patent: WO2004/74296, 2004, A2, . Location in patent: Page/Page column 13
[11] Patent: WO2004/74296, 2004, A2, . Location in patent: Page/Page column 13
  • 10
  • [ 19064-18-7 ]
  • [ 437-81-0 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 90, p. 48777 - 48782
[2] Chinese Journal of Chemistry, 2014, vol. 32, # 2, p. 117 - 122
  • 11
  • [ 85068-28-6 ]
  • [ 437-81-0 ]
Reference: [1] Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1081 - 1084
[2] Journal of the Iranian Chemical Society, 2011, vol. 8, # 2, p. 470 - 476
  • 12
  • [ 83-38-5 ]
  • [ 2751-90-8 ]
  • [ 437-81-0 ]
Reference: [1] Patent: US6127581, 2000, A,
  • 13
  • [ 83-38-5 ]
  • [ 437-81-0 ]
  • [ 387-45-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
  • 14
  • [ 446-52-6 ]
  • [ 437-81-0 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792
  • 15
  • [ 617-84-5 ]
  • [ 372-18-9 ]
  • [ 93343-10-3 ]
  • [ 256417-10-4 ]
  • [ 437-81-0 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 43, p. 10280 - 10284
  • 16
  • [ 19064-18-7 ]
  • [ 105-56-6 ]
  • [ 437-81-0 ]
  • [ 790227-40-6 ]
Reference: [1] ChemCatChem, 2016, vol. 8, # 5, p. 929 - 937
  • 17
  • [ 67-56-1 ]
  • [ 372-18-9 ]
  • [ 68-12-2 ]
  • [ 437-81-0 ]
  • [ 13671-00-6 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 20℃; for 2 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 18
  • [ 67-56-1 ]
  • [ 437-81-0 ]
  • [ 13671-00-6 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 5, p. 1082 - 1089
  • 19
  • [ 437-81-0 ]
  • [ 13671-00-6 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 17, p. 3931 - 3943
  • 20
  • [ 437-81-0 ]
  • [ 28177-48-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 7-8, p. 1027 - 1034
  • 21
  • [ 83-38-5 ]
  • [ 437-81-0 ]
  • [ 387-45-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
  • 22
  • [ 437-81-0 ]
  • [ 19064-18-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1968, vol. 11, # 4, p. 814 - 819
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1110 - 1113
  • 23
  • [ 437-81-0 ]
  • [ 654-01-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1110 - 1113
  • 24
  • [ 372-18-9 ]
  • [ 109-94-4 ]
  • [ 437-81-0 ]
  • [ 19064-14-3 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In hexane at -78 - 20℃; for 16 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 25
  • [ 437-81-0 ]
  • [ 310466-38-7 ]
Reference: [1] Bioorganic and medicinal chemistry, 2004, vol. 12, # 9, p. 2251 - 2273
[2] Dyes and Pigments, 2014, vol. 100, # 1, p. 57 - 65
  • 26
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  • [ 372-18-9 ]
  • [ 93343-10-3 ]
  • [ 256417-10-4 ]
  • [ 437-81-0 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 43, p. 10280 - 10284
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