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Product Details of [ 618-51-9 ]

CAS No. :618-51-9 MDL No. :MFCD00002496
Formula : C7H5IO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KVBWBCRPWVKFQT-UHFFFAOYSA-N
M.W : 248.02 Pubchem ID :12060
Synonyms :

Calculated chemistry of [ 618-51-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.12
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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.03
Log Po/w (XLOGP3) : 3.13
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 2.18
Consensus Log Po/w : 2.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.73
Solubility : 0.0464 mg/ml ; 0.000187 mol/l
Class : Soluble
Log S (Ali) : -3.58
Solubility : 0.0649 mg/ml ; 0.000262 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.465 mg/ml ; 0.00187 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 618-51-9 ]

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 [ 618-51-9 ]

* 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 [ 618-51-9 ]
  • Downstream synthetic route of [ 618-51-9 ]

[ 618-51-9 ] Synthesis Path-Upstream   1~49

  • 1
  • [ 618-51-9 ]
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Reference: [1] Journal of the Chemical Society, 1943, p. 421,422
[2] Synthesis, 1990, # 12, p. 1143 - 1144
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1878, vol. <2> 18, p. 326
  • 3
  • [ 25487-66-5 ]
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YieldReaction ConditionsOperation in experiment
78% With iodine; potassium carbonate In acetonitrile at 80℃; for 8 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v
Reference: [1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
[2] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
  • 4
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide In 1,4-dioxane at 110℃; for 23 h;
Stage #2: With hydrogenchloride; water In 1,4-dioxane at 20℃;
A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 molpercent), 3- bromobenzoic acid (210 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and [BACKELLEDWITHARGON. TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine [(16) IL,] 0. 10mmol, 10 molpercent), 1,1, 1,3, 3,3-hexamethyldisilazane [(211, UL,] 1.00 mmol), and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature, poured into 10percent aq HCl (20 mL), and extracted with dichloromethane [(3X 15] mL). The combined organic phases were dried [(NA2SO4)] and concentrated. The residue was dissolved in dichloromethane (50 mL) and washed with an aqueous solution of 1percent HCl and 1percent [NA2SO3.] The aqueous phase was extracted with with dichloromethane [(2X20] mL). The organic phases were combined, dried (Na2SO4) and concentrated. The solid residue was washed with hexane [(3X15 ML)] and dried to provide 3-iodobenzoic acid (222 mg, 90percent yield) as white, fine needles.
Reference: [1] Patent: WO2004/13094, 2004, A2, . Location in patent: Page 44
[2] Chemical Communications, 2012, vol. 48, # 33, p. 3993 - 3995
[3] Russian Chemical Bulletin, 1995, vol. 44, # 6, p. 1050 - 1055[4] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1995, # 6, p. 1090 - 1095
  • 5
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YieldReaction ConditionsOperation in experiment
84% at 20℃; for 9 h; General procedure: A 25-mL flask was charged with Pd(OAc)2 (1.2 mg, 0.005 mmol), 1-iodo-4-nitrobenzene (1a, 127.0 mg, 0.5 mmol), K2CO3 (141.0 mg, 1.0 mmol), H2O (0.5 mL), and PEG 400 (2.0 mL); the flask was subjected to standard cycles (3 ×) of evacuation and back-filling with dry and pure CO. The mixture was stirred at r.t. for the indicated time. The mixture was poured into sat. aq NaCl (15 mL), acidified to pH 3 with 3 M aq HCl, and extracted with EtOAc (3 × 15 mL). The solvent was removed from the combined organic phases on a rotary evaporator. The crude product was purified by column chromatography (silica gel, PE–EtOAc–HCO2H, 25:1:1) to afford 2a as a light yellow solid; yield: 75mg (90percent); mp 238.0–239.3 °C. 1H NMR (400 MHz, DMSO-d6): δ = 13.68 (br s, 1 H), 8.30 (d, J = 8.0 Hz,2 H), 8.14 (d, J = 8.0 Hz, 2 H). 13C NMR (100 MHz, DMSO-d6): δ = 165.9, 150.0, 136.4, 130.7, 123.8.
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 13, p. 1861 - 1868
  • 6
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YieldReaction ConditionsOperation in experiment
61% With ethanol In water at 85℃; for 30 h; Ionic liquid General procedure: A mixture of nitrobenzene 1 (4 mmol), KCN (20,40 or 80 mmol), EtOH (5 or 7 ml), water (5 or 7 ml) and [bmim]BF4(7 mmol, 175 molpercent) was heated on the oil bath with stirring at 85 °C (seeTables 1 and 2). Then 10 ml of water was added and the mixture wasextracted with CH2Cl2 (3×10 ml) and diethyl ether (3×20 ml). The aqueouslayer was acidified with HCl to pH 1–2 and extracted with diethyl ether(3×20 ml). Magnesium sulfate (~5 g) and absorbent carbon (~1 g) wereadded to the ether layer and this was stirred for 5 h. The solid was filteredoff, the filtrate was evaporated and the residue was crystallized from thecorresponding solvent to give product 2.
Reference: [1] Mendeleev Communications, 2015, vol. 25, # 1, p. 41 - 43
  • 7
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YieldReaction ConditionsOperation in experiment
61% With dipotassium peroxodisulfate; choline chloride; iodine In acetonitrile at 65℃; for 3 h; General procedure: To a solution of aromatic compound (10 mmol) in acetonitrile (5 mL) in a 100 mL round-bottomed flask with a magnetic bar was added choline chloride(10 mmol), potassium peroxodisulfate (10 mmol) and iodine (15 mmol). The reaction mixture was stirred for the appropriate time at 65 °C. The progress of the reaction was monitored by TLC. The reaction mixture was poured into aqueous sodium thiosulfate solution (1 mol/L) in order to remove unreacted iodine and extracted with ethyl acetoacetate (10 mL, 3 times). Organic layer is dried over anhydrous sodium sulphate. Evaporation of the solvent under vacuum followed by column chromatography on silica gel gave the corresponding iodinated compounds (Scheme-I).
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[3] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8622 - 8624
[4] European Journal of Organic Chemistry, 2017, vol. 2017, # 22, p. 3234 - 3239
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[13] Tetrahedron, 2004, vol. 60, # 41, p. 9113 - 9119
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[15] Chinese Chemical Letters, 2012, vol. 23, # 3, p. 261 - 264
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[18] Molecules, 2005, vol. 10, # 2, p. 394 - 400
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[20] Asian Journal of Chemistry, 2018, vol. 30, # 7, p. 1659 - 1663
[21] Synthesis, 1999, # 5, p. 748 - 750
[22] Synthesis, 2011, # 5, p. 739 - 744
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[27] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 11, p. 2623 - 2624
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[29] Justus Liebigs Annalen der Chemie, 1865, vol. 136, p. 201
[30] Journal of the Chemical Society, 1950, p. 3694
[31] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1022; engl. Ausg. S. 1071
[32] Journal of the Chemical Society, 1952, p. 993,1000
[33] Journal of Organic Chemistry, 1959, vol. 24, p. 1818
[34] Journal of the American Chemical Society, 1919, vol. 41, p. 294
[35] Russian Journal of Organic Chemistry, 2008, vol. 44, # 6, p. 935 - 936
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[2] Justus Liebigs Annalen der Chemie, 1865, vol. 135, p. 108
[3] Journal fuer Praktische Chemie (Leipzig), 1878, vol. <2> 18, p. 326
[4] Justus Liebigs Annalen der Chemie, 1860, vol. 113, p. 335[5] Justus Liebigs Annalen der Chemie, 1861, vol. 117, p. 13,21
  • 9
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[2] Journal of Chemical Education, 1938, vol. 15, p. 217
[3] Journal of the Chinese Chemical Society (Peking), 1946, vol. 14, p. 24,29
  • 10
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Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6921 - 6923
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  • 12
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  • 15
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  • 17
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  • 18
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  • 19
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[3] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 11, p. 2071 - 2075[4] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 11, p. 2368 - 2373
  • 20
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[2] Trans. roy. Soc. Canada, 1934, vol. <3> 28 III, p. 97,98
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  • 22
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  • 32
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  • [ 618-91-7 ]
YieldReaction ConditionsOperation in experiment
97% at 80℃; for 24 h; 3-lodobenzoic acid (50 g, 0.20 mol) was mixed with 300 mL methanol followed by the addition of 1 mL of concentrated sulfuric acid. The reaction was heated at 80 °C for 24 hours. During this process, the mixture of methanol and water was replaced by methanol twice. When the reaction appeared complete by TLC, the solvents were removed. The addition of 600 mL I feO and overnight stirring led to the formation of large amount of white precipitate. The product was readily isolated by filtration and washed by water to give a white solid (51.3 g, 97 percent). NM (300 MHz, C CI3): δ 8.34 (s, br, III), 7.97 (d, J= 7.5 I Iz, I H), 7.85 (d, J= 7.2 Hz, I H), 7.151 (td, J/ - 7.8 Hz, J2 = 2.7 Hz, I II), 3.89 (s, 311). GC-MS (m/z): [M'j calcd. for C8H7l02: 262.0, found: 262.0.
96.5% for 24 h; Reflux To a solution of 3-iodobenzoic acid (50.0 g, 0.202 mol) in methanol (300.0 ml) was added H2SO4 (1.0 ml). The reaction mixture was heated to reflux. After reflux 24 h, heating was stopped. The reaction mixture was cooled to room temperature. Water (400.0 ml) was added, the product was extracted with ethyl acetate (2 x 300.0 ml). The organic layer was washed with 20percent OfNaHCO3 water solution and followed with water. After removal of ethyl acetate, the crude product was purified by recrystallization from ethanol/water. Final white pure product was obtained in 51.0 g (96.5percent) after dry under vacuum. 1H NMR (400 MHz, CDCl3, δ): 8.35 (t, J = 1.6 Hz, 1 H), 7.97 (dt, Ji = 8.4 Hz, J2 = 1.6 Hz, 1 H), 7.85 (dt, Jl = 8.4 Hz, J2 = 1.6 Hz, 1 H), 7.14 (t, J = 8.4 Hz, 1 H), 3.89 (s, 3 H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 165.56, 141.70, 138.42, 131.93, 130.03, 128.70, 93.76, 52.38.
96% for 21 h; Reflux 3-iodobenzoic acid (103) and (3.00 g) was dissolved in methanol (60 mL), concentrated sulfuric acid (2 mL) was added and refluxed for 21 hours. The reaction mixture was concentrated, the residue was dissolved in ethyl acetate (100 mL), the organic layer was washed with water (100 mL), saturated aqueous sodium hydrogen carbonate solution (100 mL), saturated brine (100 mL), sulfuric anhydride dried with sodium, and filtered. The filtrate was concentrated under reduced pressure to give 3-iodo-benzoic acid methyl ester (104) and (3.04 g, 96percent yield) as a pale yellow solid.
93% at 0 - 20℃; for 16 h; 117A: Methyl 3-iodobenzoate; 3-iodobenzoic acid (7.44 g, 30 mmol) was suspended in dry MeOH (40 mL) under nitrogen at 0° C. SOCl2 (3.3 mL) was added over 5 minutes. Stirring continued at room temperature for 16 hours, after which the reaction mixture was concentrated. The residue was dissolved in EtOAc and was washed twice with NaHCO3 (conc.). The organic solution was dried over MgSO4, filtered and concentrated to yield a white crystalline solid (7.32 g, 93percent). NMR 1H (ppm, CDCl3): 8.36 (t, J4=1.6 Hz, 1H), 7.98 (d, J3=7.8 Hz, 1H), 7.86 (d, J3=7.9 Hz, 1H), 7.16 (t, J3=7.8 Hz, 1H), 3.90 (s, 3H).
78.4% at 80℃; for 18 h; Example 3: Synthesis of 3-trimethylstannyl-benzoic acid 2,5-dioxo- pryolidin-1-yl ester3d) Methyl 3-lodobenzoate (2)One drop of dimethylformamide was added to a stirring suspension of 3- iodobenzoic acid (1.Og, 4.03 mmol), in thionyl chloride (20 ml). The mixture was then heated at 800C for 18 hours. After cooling to ambient temperature, the solvent was completely evaporated, then methanol (20 ml) was slowly added and the mixture stirred at ambient temperature for 30 minutes. Evaporation of methanol afforded the crude product as oil which solidified on standing at ambient temperature. The crude product was purified by flash chromatography using ethyl acetate/ hexane (1 :1) and the pure product was obtained as slightly yellow crystals (824 mg, 78.4percent).1H NMR (500 MHz, CDCI3, .pound.3.95 (s, 3H, CH3), 7.20 (t, 1 H), 7.9 (d, 1 H), 8.0 (d, 1 H), 8.20 (s, 1 H)

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[2] Patent: WO2014/11477, 2014, A1, . Location in patent: Page/Page column 29; 30
[3] Patent: WO2010/149620, 2010, A1, . Location in patent: Page/Page column 45
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YieldReaction ConditionsOperation in experiment
100% With chloro-trimethyl-silane In methanol 8(a)
Methyl 3-iodobenzoate
3-Iodobenzoic acid (10.0 g, 40.3 mmol) was placed in dry methanol (50 mL) under an argon atmosphere and was treated with chlorotrimethylsilane (15.4 mL, 0.12 mol).
After heating at 65° C. for 4 h, the mixture was cooled to room temperature and was concentrated in vacuo.
The residue was partitioned between ethyl acetate (100 mL) and water, the organic phase was washed twice with water, was dried (Na2 SO4) and was evaporated to provide the titled compound as a white solid (10.6 g, 100percent).
Reference: [1] Patent: US6037367, 2000, A,
[2] Journal of the Chinese Chemical Society (Peking), 1946, vol. 14, p. 24,29
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  • [ 58313-23-8 ]
YieldReaction ConditionsOperation in experiment
83% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; To a 250 mL round-bottom flask in a 0 °C ice bath was added 3-iodobenzoic acid (10 g, 40 mmol), EDCI (8.5 g, 44 mmol), DCM (80 mL) and allowed to stir for 10 min. To the stirred solution was added DMAP (500 mg, 4 mmol), ethanol (2.9 mL) and allowed to stir overnight. Disappearance of SM was monitored by HPLC and TLC. Reaction mixture was diluted with 1 N HCI, extracted with EtOAc, dried with magnesium sulfate, and concentrated in vacuo. Required column chromotography (10: 1 Hex/EtOAc) to isolate product.
83%
Stage #1: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667 h;
To a 250 mL round-bottom flask in a 0 °C ice bath was added 3-iodobenzoic acid (10 g, 40 mmol), EDCI (8.5 g, 44 mmol), DCM (80 mL) and allowed to stir for 10 min. To the stirred solution was added DMAP (500 mg, 4 mmol), ethanol (2.9 mL) and allowed to stir overnight. Disappearance of SM was monitored by HPLC and TLC. Reaction mixture was diluted with 1 N HCI, extracted with EtOAc, dried with magnisium sulfate, and concentrated in vacuo. Required column chromotography (10: 1 Hex/EtOAc) to isolate product.
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  • [ 10602-06-9 ]
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  • [ 10601-99-7 ]
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  • [ 3872-23-9 ]
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  • [ 946-65-6 ]
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  • [ 25015-63-8 ]
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  • [ 269409-73-6 ]
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  • [ 73183-34-3 ]
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  • [ 914943-91-2 ]
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