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[ CAS No. 3240-34-4 ] {[proInfo.proName]}

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Chemical Structure| 3240-34-4
Chemical Structure| 3240-34-4
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Product Details of [ 3240-34-4 ]

CAS No. :3240-34-4 MDL No. :MFCD00008692
Formula : C10H11IO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZBIKORITPGTTGI-UHFFFAOYSA-N
M.W :322.10 Pubchem ID :76724
Synonyms :

Calculated chemistry of [ 3240-34-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.07
TPSA : 52.6 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) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.77
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 2.12
Log Po/w (SILICOS-IT) : 2.18
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.55
Solubility : 0.0912 mg/ml ; 0.000283 mol/l
Class : Soluble
Log S (Ali) : -3.53
Solubility : 0.095 mg/ml ; 0.000295 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.105 mg/ml ; 0.000327 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.48

Safety of [ 3240-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3240-34-4 ]

* 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 [ 3240-34-4 ]
  • Downstream synthetic route of [ 3240-34-4 ]

[ 3240-34-4 ] Synthesis Path-Upstream   1~39

  • 1
  • [ 3240-34-4 ]
  • [ 1342517-04-7 ]
  • [ 42602-67-5 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 197 - 209
  • 2
  • [ 3240-34-4 ]
  • [ 42602-67-5 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 197 - 209
  • 3
  • [ 3240-34-4 ]
  • [ 65094-35-1 ]
  • [ 1780-17-2 ]
  • [ 60483-07-0 ]
Reference: [1] Heterocycles, 1996, vol. 43, # 6, p. 1151 - 1158
  • 4
  • [ 3240-34-4 ]
  • [ 79669-49-1 ]
  • [ 19477-73-7 ]
Reference: [1] Patent: WO2011/44506, 2011, A2, . Location in patent: Page/Page column 151
  • 5
  • [ 230-27-3 ]
  • [ 3240-34-4 ]
  • [ 33155-90-7 ]
  • [ 83491-10-5 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 8, p. 2300 - 2301
  • 6
  • [ 4702-13-0 ]
  • [ 3240-34-4 ]
  • [ 124-38-9 ]
  • [ 5493-24-3 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 18, p. 4476 - 4478
  • 7
  • [ 3240-34-4 ]
  • [ 76-05-1 ]
  • [ 2712-78-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 1685 - 1689[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 9, p. 1886 - 1892
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 1709 - 1716
[4] Journal of Chemical Research, 2009, # 1, p. 30 - 31
[5] Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 1246 - 1249[6] Zhurnal Organicheskoi Khimii, 1975, vol. 11, p. 1259 - 1262
[7] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1935 - 1939[8] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2124 - 2129
[9] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4272 - 4276
[10] Tetrahedron, 1983, vol. 39, # 14, p. 2393 - 2397
[11] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
[12] Synthesis, 2007, # 18, p. 2913 - 2919
[13] Journal of Organic Chemistry, 2018, vol. 83, # 23, p. 14262 - 14268
  • 8
  • [ 3240-34-4 ]
  • [ 407-25-0 ]
  • [ 2712-78-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1281 - 1286
  • 9
  • [ 3240-34-4 ]
  • [ 2712-78-9 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 3509 - 3512
[2] Journal of Organic Chemistry, 2015, vol. 80, # 6, p. 3339 - 3342
  • 10
  • [ 591-50-4 ]
  • [ 108-24-7 ]
  • [ 3240-34-4 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 8, p. 1735 - 1742
[2] Molecules, 2002, vol. 7, # 11, p. 806 - 809
[3] Molecules, 2001, vol. 6, # 11, p. 881 - 891
[4] Angewandte Chemie - International Edition, 2009, vol. 48, # 45, p. 8547 - 8550
[5] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 197 - 209
[6] Molecules, 2005, vol. 10, # 1, p. 190 - 194
[7] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1975, p. 1161 - 1166
[8] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1935 - 1939[9] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2124 - 2129
[10] Zeitschrift fuer Physikalische Chemie (Leipzig), 1981, vol. 262, # 1, p. 176 - 188
[11] Journal of Chemical Research, 2007, # 4, p. 252 - 256
[12] Tetrahedron Letters, 2012, vol. 53, # 34, p. 4588 - 4590
  • 11
  • [ 591-50-4 ]
  • [ 75-07-0 ]
  • [ 3240-34-4 ]
YieldReaction ConditionsOperation in experiment
92% at 23℃; for 5 h; Sealed tube General procedure: In a typical experiment, a 20 ml scintillation vial was charged with glacial AcOH (2 ml), iodoarene (0.401 mmol) andCoCl2·6H2O (0.004 mmol, 1 molpercent) and was fitted with a rubber septum. The reaction vessel was purged with O2 for 5 min before acetaldehyde (4.07 mmol, 10.2 equiv.) was added in one portion. The reaction mixture was stirred under 1 atm O2, delivered by inflated balloon at 23 °C for 5 h. The solvent was removed in vacuo and the residuewasdissolved in CH2Cl2. The organic layer was washed with distilled water and extracted with CH2Cl2 (3 × 7 ml). The organic layer was dried over MgSO4 and solvent was removed in vacuo to afford the corresponding iodobenzene diacetate. The isolatedcompounds were characterized by 1H and 13C NMR spectroscopies.
Reference: [1] Nature Chemistry, 2018, vol. 10, # 2, p. 200 - 204
  • 12
  • [ 591-50-4 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 3240-34-4 ]
YieldReaction ConditionsOperation in experiment
91% at 45℃; General procedure: The aromatic iodine compound (1, 2 or 3) (1 g) was dissolved in a mixed solution of acetic acid (3 mL) and acetic anhydride (3 mL)Under stirring at 45 to the solution was slowly added sodium borate (aromatic iodine molar amount of 10 times), maintaining the temperature constant reaction until the raw material disappears completely, about 4-6 hours, cooled to room temperature and water ( The mixture was filtered to give a white solid which was filtered to give a solid which was extracted three more times with ethyl acetate (20 mL). The organic phase was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a white solid which was combined with the previously filtered solid , And the crude product was washed with a mixed solution of acetone and petroleum ether in a volume ratio of 1: 1 to obtain the pure product (4,5 or 6) as a white solid with the corresponding yields of 91percent, 86percent and 88percent, respectively.
Reference: [1] Patent: CN106883170, 2017, A, . Location in patent: Paragraph 0038; 0039; 0040
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4303 - 4308
  • 13
  • [ 64-19-7 ]
  • [ 71-43-2 ]
  • [ 3240-34-4 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 45, p. 7889 - 7891
[2] Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 11, p. 2213 - 2219
[3] RSC Advances, 2014, vol. 4, # 6, p. 2954 - 2960
  • 14
  • [ 79-21-0 ]
  • [ 591-50-4 ]
  • [ 3240-34-4 ]
Reference: [1] Molecules, 2005, vol. 10, # 1, p. 217 - 225
[2] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 1709 - 1716
[3] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1930, vol. 33, p. 827,828[4] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1932, vol. 35, p. 1140
[5] Journal fuer Praktische Chemie (Leipzig), 1931, vol. <2> 131, p. 357,367[6] Trudy Kazansk. chim. technol. Inst., 1936, # 6, p. 190,225
[7] Organic Syntheses, 1963, vol. 43, p. 65,67
[8] Journal of the American Chemical Society, 1967, vol. 89, # 10, p. 2333 - 2338
  • 15
  • [ 591-50-4 ]
  • [ 64-19-7 ]
  • [ 3240-34-4 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6984 - 6986
[2] Synthesis, 2005, # 12, p. 1932 - 1934
[3] Chemistry - A European Journal, 2016, vol. 22, # 45, p. 16072 - 16077
[4] Synlett, 2012, vol. 23, # 18, p. 2663 - 2666,4
[5] Tetrahedron, 1989, vol. 45, # 11, p. 3299 - 3306
[6] Journal of Organic Chemistry, 2018,
[7] European Journal of Organic Chemistry, 2013, # 12, p. 2334 - 2345
[8] Tetrahedron, 1989, vol. 45, # 11, p. 3299 - 3306
[9] Tetrahedron Letters, 1995, vol. 36, # 38, p. 6945 - 6948
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 17, p. 2135 - 2140
[11] Organic Letters, 2005, vol. 7, # 18, p. 3961 - 3964
[12] Patent: WO2010/30967, 2010, A1, . Location in patent: Page/Page column 60
[13] Patent: WO2010/30967, 2010, A1, . Location in patent: Page/Page column 60
[14] Rapid Communications in Mass Spectrometry, 2012, vol. 26, # 6, p. 616 - 620
[15] Chemistry - A European Journal, 2016, vol. 22, # 10, p. 3485 - 3490
  • 16
  • [ 64-19-7 ]
  • [ 71-43-2 ]
  • [ 591-50-4 ]
  • [ 3240-34-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 11, p. 2213 - 2219
  • 17
  • [ 55962-05-5 ]
  • [ 64-19-7 ]
  • [ 3240-34-4 ]
  • [ 70-55-3 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 40, p. 5578 - 5581
  • 18
  • [ 2754-27-0 ]
  • [ 536-80-1 ]
  • [ 3240-34-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 8.2, p. 1633 - 1634[2] Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 8, p. 1807 - 1808
  • 19
  • [ 591-50-4 ]
  • [ 3240-34-4 ]
Reference: [1] Oriental Journal of Chemistry, 2012, vol. 28, # 2, p. 857 - 866,10
  • 20
  • [ 873-49-4 ]
  • [ 3240-34-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1935 - 1939[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2124 - 2129
  • 21
  • [ 536-80-1 ]
  • [ 64-19-7 ]
  • [ 3240-34-4 ]
Reference: [1] Journal of the Chemical Society, 1960, p. 1209 - 1214
[2] Journal of the Chemical Society, 1965, p. 3721 - 3728
  • 22
  • [ 64-19-7 ]
  • [ 122-97-4 ]
  • [ 3240-34-4 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 787 - 793
  • 23
  • [ 3240-34-4 ]
  • [ 618-51-9 ]
  • [ 618-91-7 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 10, p. 2027 - 2031
  • 24
  • [ 3240-34-4 ]
  • [ 108549-23-1 ]
  • [ 108-68-9 ]
  • [ 17176-77-1 ]
YieldReaction ConditionsOperation in experiment
52% With 1H-tetrazole In dichloromethane; acetonitrile Example 8
Dibenzylphosphonate 11:
A solution of 10 (85 mg, 0.15 mmol) and 1H-tetrazole (14 mg, 0.20 mmol) in CH2Cl2 (2 mL) was treated with Dibenzyldiisopropylphosphoramidite (60 μL, 0.20 mmol) and stirred at room temperature overnight.
The product was partitioned between CH2Cl2 and H2O, dried with Na2SO4, filtered and concentrated.
The crude product was purified by column chromatography to give the intermediate dibenzylphosphite (85 mg, 0.11 mmol) which was dissolved in CH3CN (2 mL) and treated with iodobenzenediacetate (51 mg, 0.16 mmol).
The reaction mixture was stirred at room temperature for 3 h and concentrated.
The residue was partitioned between EtOAc and NaHCO3.
The organic layer was washed with H2O, dried with Na2SO4, filtered, and concentrated.
The crude product was purified by column chromatography on silica gel (3percent 2-propanol/CH2Cl2) to give the dibenzylphosphonate (45 mg, 52percent) as a white solid.
52% With 1H-tetrazole In dichloromethane; acetonitrile Example W8
Dibenzylphosphonate 11:
A solution of 10 (85 mg, 0.15 mmol) and 1H-tetrazole (14 mg, 0.20 mmol) in CH2Cl2 (2 mL) was treated with Dibenzyldiisopropylphosphoramidite (60 μL, 0.20 mmol) and stirred at room temperature overnight.
The product was partitioned between CH2Cl2 and H2O, dried with Na2SO4, filtered and concentrated.
The crude product was purified by column chromatography to give the intermediate dibenzylphosphite (85 mg, 0.11 mmol) which was dissolved in CH3CN (2 mL) and treated with iodobenzenediacetate (51 mg, 0.16 mmol).
The reaction mixture was stirred at room temperature for 3 h and concentrated.
The residue was partitioned between EtOAc and NaHCO3.
The organic layer was washed with H2O, dried with Na2SO4, filtered, and concentrated.
The crude product was purified by column chromatography on silica gel (3percent 2-propanoUICH2Cl2) to give the dibenzylphosphonate (45 mg, 52percent) as a white solid.
Reference: [1] Patent: US2004/121316, 2004, A1,
[2] Patent: US2005/239054, 2005, A1,
  • 25
  • [ 3240-34-4 ]
  • [ 17729-59-8 ]
  • [ 40400-15-5 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0833333 h; Inert atmosphere
Stage #2: at -78℃; for 0.0833333 h;
Under N2 protection,The re-distilled dichloromethane (5 mL) was added to a 25 ml reaction tube.Then 161 mg (0.5 mmol) of iodobenzene diacetate was added.Then 180 μl of trimethylsilyl triflate (TMSOTf, 1.0 mmol) was added.The reaction solution was stirred at room temperature for 5 min.Finally, 198 mg (0.6 mmol) of α-tributyltin acetonitrile was added at -78 °C.Stir for 5min,Track the progress of the reaction by thin layer chromatography.After the reaction was completed, a saturated sodium hydrogencarbonate solution (3 ml) was added to quench the reaction.Slowly warm to room temperature,Then extracted with dichloromethane (3 mL×3).The organic phase is dried over anhydrous sodium sulfate.Concentrated in vacuo,Separated by column chromatography (Rf = 0.19, developing solvent: petroleum ether / ethyl acetate = 40/1, v/v),Product obtainedThe α-aryl nitrile compound is a white solid.The yield was 86percent.
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 29, p. 9078 - 9082[2] Angew. Chem., 2018, vol. 130, # 29, p. 9216 - 9220,5
[3] Patent: CN108409602, 2018, A, . Location in patent: Paragraph 0022; 0023; 0024
  • 26
  • [ 3240-34-4 ]
  • [ 614-76-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 197 - 209
  • 27
  • [ 1039765-14-4 ]
  • [ 3240-34-4 ]
  • [ 614-76-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 197 - 209
  • 28
  • [ 88-67-5 ]
  • [ 3240-34-4 ]
  • [ 610-97-9 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 10, p. 2027 - 2031
  • 29
  • [ 3240-34-4 ]
  • [ 14199-15-6 ]
  • [ 1198-84-1 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, # 29, p. 2747 - 2750
  • 30
  • [ 108-86-1 ]
  • [ 3240-34-4 ]
  • [ 1927-95-3 ]
  • [ 1829-37-4 ]
  • [ 35065-86-2 ]
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  • 31
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  • [ 35065-86-2 ]
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  • 32
  • [ 26838-86-8 ]
  • [ 3240-34-4 ]
  • [ 34883-46-0 ]
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  • 33
  • [ 3240-34-4 ]
  • [ 86941-88-0 ]
  • [ 32136-81-5 ]
Reference: [1] Helvetica Chimica Acta, 1994, vol. 77, p. 1595 - 1610
  • 34
  • [ 3240-34-4 ]
  • [ 3113-71-1 ]
  • [ 24078-21-5 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 10, p. 2027 - 2031
  • 35
  • [ 1493-13-6 ]
  • [ 3240-34-4 ]
  • [ 71-43-2 ]
  • [ 66003-76-7 ]
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[2] Synthesis, 1994, # 2, p. 147 - 148
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  • 36
  • [ 1493-13-6 ]
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  • [ 66003-76-7 ]
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  • 37
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  • [ 3240-34-4 ]
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  • 38
  • [ 3240-34-4 ]
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Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 21, p. 3721 - 3722
  • 39
  • [ 3240-34-4 ]
  • [ 3375-31-3 ]
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