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CAS No. : | 160003-66-7 | MDL No. : | MFCD11110639 |
Formula : | C7H5IN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MDOJTZQKHMAPBK-UHFFFAOYSA-N |
M.W : | 292.03 | Pubchem ID : | 9796068 |
Synonyms : |
BSI-201;IND-71677;SAR-240550;INO-2BA;NIBA;ND-71677;NSC-746045
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 56.08 |
TPSA : | 88.91 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.17 cm/s |
Log Po/w (iLOGP) : | 0.93 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.3 |
Log Po/w (MLOGP) : | 1.02 |
Log Po/w (SILICOS-IT) : | -0.17 |
Consensus Log Po/w : | 0.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.67 |
Solubility : | 0.629 mg/ml ; 0.00216 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.75 |
Solubility : | 0.523 mg/ml ; 0.00179 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.31 |
Solubility : | 1.43 mg/ml ; 0.0049 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.02 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.2% | With ammonia In methanol at 35℃; | A solution of 3.7 g of methyl 4-iodo-3-nitrobenzoate and 30 mL of methanol was charged into a reaction flask,Stirring at 35 ° C,Through ammonia,TLCMonitoring the reaction process, the expansion agent volume ratio of ethyl acetate: petroleum ether = 1: 1. After completion of the reaction,The reaction was evaporated to dryness to give 3.3 g of crude product as a yellow solid. The crude product was recrystallized from 19.8 mL of ethanol and pumped to give a yellow crystal which was dried in vacuo to give 3.0 g of 4-iodo-3-nitrobenzamide, HPLC purity 99.75percent and yield 85.2percent. |
80.2% | With ammonia In methanol at -15 - 25℃; for 72 h; | Example 3 Preparation of 4-iodo-3-nitrobenzamide A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0g, 6.5 mmol) in methanol (80 ml) is cooled to -15° C. To the solution, ammonia gas (about 1.02 g, 0.06 mol) is passed till saturation. The solution is kept at room temperature (25+-2° C.) for 3 days. The solvent is then evaporated under reduced pressure to obtain 4-iodo-3-nitrobenzamide as an yellow solid (95percent yield, 98percent HPLC). The solid (1 g) is added to methanol (10 ml) and heated to 55° C. to get a clear solution. While the solution is hot, water (35 ml) is added and the precipitate so formed is filtered to obtain pure 4-iodo-3-nitrobenzamide. 1H-NMR spectrum: DMSO-d6: δ 7.74 (brs, NH2), 7.86 (dd, Ar-H), 8.24 (d, Ar-H), 8.70(d, Ar-H). 13C-NMR spectrum: DMSO-d6: δ 91.76, 123.63, 132.03, 135.36, 141.49, 153.15, and 165.19. Yield: 1.52 g (80.2percent), 99.6 -99.8percent HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.5% | With thionyl chloride In water; N,N-dimethyl-formamide; acetonitrile | C. 4-Iodo-3-Nitrobenzamide In a 100-mL flask equipped with a magnetic stirrer, thermometer and ice bath, a stirred solution of 4-Iodo-3-nitrobenzoic acid (1025 mg, 3.50 mMoles) (Chemica Alta Ltd., Edmonton, Alberta, Canada) in N,N-dimethylformamide (10 mL) is cooled to 10° C., and then thionyl chloride (0.76 mL, 10.5 mMoles) is added to it. There is no exothermicity, the ice bath is removed, and the solution is allowed to warm to ambient temperature, and stirring is continued for a total of 1 hour. Then the solution is poured into chilled, concentrated ammonium hydroxide (20 mL), resulting in a dark yellow mixture, which is stirred for 5 minutes. Then chilled deionized water (50 mL) is added, causing precipitation of the light yellow product. After allowing the precipitation mixture to stand chilled on ice for 10 minutes, the precipitate is collected on a suction filter, rinsed with cold water, and then dried by vacuum pumping. The resultant crude product (500.4 mg) is then re-crystallized by dissolving it in acetonitrile (7.0 mL) heated to about 65° C., followed by cooling and allowing the solution to stand in the refrigerator overnight. The yellow crystals are collected, rinsed with chilled solvent and dried by vacuum pumping, to give 415.2 mg (40.5percent yield) of 4-Iodo-3-nitrobenzamide, m.p. 152°-155° C. 1 H NMR spectrum, in DMSO-d6 δ (ppm) values relative to TMS): broad singlet (7.67) due to one nonequivalent proton of the amido NH2 group; doublet of doublets (7.84, 7.85 and 7.86, 7.87) due to H-5 split by H-6 and finely split by H-2; doublet (8.22, 8.24) due to H-6 split by H-5; broad singlet centered near 8.22, overlapping the signal of H-6, due to the second nonequivalent proton of the amido NH2 group; doublet (8.35, 8.36) due to H-2 finely split by H-5. At higher NMR field signals due to adventitious water (2.5 ppm), deuterated-DMSO impurity protons (3.3 ppm) and crystallization solvent acetonitrile (single at 2.07 ppm) are observed. Integration of the acetonitrile signal indicates approximately one molecule of acetonitrile per 3 molecules of 4-iodo-3-nitrobenzamide. UV absorption spectrum in absolute ethanol, λ max (ε): 308 nm (1.59*103), 242 nm (1.31*104), 208 nm (1.45*104) Elemental analysis (Schwarzkopf Microanalytical Laboratory): Calculated for C7 H5 N2 O3 I: C, 28.79percent; H, 1.72; I, 43.46; N, 9.59. Found: C, 29.63; H, 1.72; I, 41.47; N, 9.99. Deviations from calculated are believed to be due to the presence of acetonitrile (crystallization solvent) as detected in the NMR spectrum. High resolution EI mass spectrum: calculated for C7 H5 N2 O3 I: 291.9345; Found: M+ (m/z) 291.9349 (deviation=-1.4 ppm). |