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CAS No. : | 123158-75-8 |
Formula : | C6H4ClIN2O2 |
M.W : | 298.47 |
SMILES Code : | NC1=C([N+]([O-])=O)C=C(Cl)C=C1I |
MDL No. : | MFCD23115369 |
InChI Key : | WDQPNLNIJFQQRL-UHFFFAOYSA-N |
Pubchem ID : | 12143564 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
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 | 57.4 |
TPSA ? Topological Polar Surface Area: Calculated from | 71.84 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.62 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.9 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.8 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 0.63 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.88 |
Log S (ESOL):? ESOL: Topological method implemented from | -3.82 |
Solubility | 0.045 mg/ml ; 0.000151 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -4.07 |
Solubility | 0.0255 mg/ml ; 0.0000853 mol/l |
Class? Solubility class: Log S scale | Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.98 |
Solubility | 0.316 mg/ml ; 0.00106 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -6.06 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 4.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 2.56 |
* 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 |
---|---|---|
69% | With iodine; silver nitrate; In ethanol; at 20℃; for 8h; | (Step 1)Commercially available 4-chloro-2-nitro-phenylamine (17.4 g, 131.5 mmol) was dissolved in ethanol (300 mL), and thereto silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol) were added. The mixture was stirred for 8 hours at room temperature. At the end of reaction, the mixture was filtered using celite and washed with 100 ml of ethylacetate and concentrated. To the concentrate, added water and extracted with ethylacetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate to give 2-amino-5-chloro-3-nitro-phenyliodide (27.4 g, Yield 69%).1H-NMR (500 MHz, CDCl3); delta 7.94 (s, 1H), 7.75 (s, 1H), 6.48 (br s, 2H), 2.23 (s, 3H) |
28% | With Iodine monochloride; In glacial AcOH; | A. Synthesis of 4-chloro-2-iodo-6-nitroaniline: The procedure of Leeson, P. D. et al. (J. Med. Chem. 34:1243-1252 (1991)) was adapted. To a solution of 4-chloro-2-nitroaniline (2.15 g, 12.45 mMol, Aldrich, used as received) in glacial AcOH (16 mL) was added iodine monochloride (2.114 g, 12.90 mMol, Aldrich). The mixture was heated at 120 C. for 5 h, then cooled and poured into ice water (30 g). The precipitate was collected and washed with 10% sodium sulfite solution (20 mL), then it was crystallized from MeOH to give 4-chloro-2-iodo-6-nitroaniline (1.05 g, 28%), as long brown needles, m.p. 134-5 C. NMR (1 H, CDCl3): delta6.660 (s, 2H); 7.906 (d, 1H, J=2.1 Hz); 8.188 (d, 1H, J=1.8 Hz). |
With Iodine monochloride; In acetic acid; | a) A solution of 4-chloro-2-nitroaniline (34.5 g) in acetic acid (500 ml) was refluxed with iodine monochloride (65.0 g) for 7 h with stirring, then was cooled and added to excess water. The precipitate was filtered off, washed with aqueous sodium sulphite and after column chromatography yielded 4-chloro-2-iodo-6-nitroaniline (8.5 g). delta (360 MHz, DMSO-d6) 7.13 (2H, bs, NH2), 8.08 (1H, d, 3-H) and 8.13 (1H, d, 5-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;Pb-CaCO3; In tetrahydrofuran; | Example B4 Preparation of 4-chloro-6-iodo-1.2-phenylenediamine 1.5 g of <strong>[123158-75-8]4-chloro-2-iodo-6-nitroaniline</strong> together with 50 ml of tetrahydrofuran and 10 ml of 1-propanol are initially introduced into a stirred autoclave. 5 mg of FeCl2.4H2 O and 0.3 g Pt/Pb-CaCO3 catalyst are added to the solution, and hydrogenation is carried out at 130 C. and 20 bar of hydrogen. After the hydrogenation has come to a standstill, the reaction mixture is cooled to room temperature, the reactor is rendered inert with nitrogen and the catalyst is filtered off. After filtration, the solvent is removed by distillation to give 1.3 g of 4-chloro-6-iodo-1,2-phenylenediamine as a crude product. 1 H-NMR (CDCI3, 300MHz) 3.56 ppm (s, 2H, broad); 3.77 ppm (s, 2H, broad); 6.68 ppm (s, 1H); 7.18 ppm (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; silver nitrate; In ethanol; at 20℃; for 8h; | General procedure: Commercially available 4-methyl-2-nitro-phenylamine (20 g, 131.5 mmol) was dissolved in ethanol (300 mL), silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with 100 mL of ethyl acetate, and concentrated. Water was added to the residue, which was then extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate to give the title compound (29 g, Yield 69%). | |
With iodine; silver nitrate; In ethanol; at 20℃; for 8h; | General procedure: Commercially available 4-methyl-2-nitro - phenylamine (20g, 131.5mmol) was dissolved in ethanol (300mL), was added silver nitrate (27g, 157.7mmol) and iodine (40g, 157.7mmol), in It was stirred at room temperature for 8 hours. After completion of the reaction, the Cellite filtration, washing with ethyl acetate 100mL was concentrated. After addition of water and extracted with ethyl acetate. After washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the harvest of the title compound (29g, yield 69%). | |
With iodine; silver nitrate; In ethanol; at 20℃; for 8h; | General procedure: Commercially available 4-methyl-2-nitro-phenylamine (20 g, 131.5 mmol) was dissolved in ethanol (300 ml), to which were added silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol), and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, the mixture was filtered through Cellite, washed with ethyl acetate (100 ml), and concentrated. The reactant was added with water, extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried with anhydrous magnesium sulfate to give the title compound (29 g, Yield 69%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h; | <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in <n="51"/>Preparation 19 and l-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 rnL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100C . After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%). 1H-NMR (400HMz, CDCl3); delta 9.78(br s, IH), 8.15(s, IH), 7.78(s, IH),7.38~7.48(m, 5H), 0.26(s, 9H) |
87% | With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h; | Preparation 41: 5-Chloro-3-phenyl-7-nitro-1H-indoleStep A: 5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole; <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).1H-NMR (400 MHz, CDCl3); delta 9.78(br s, 1H), 8.15(s, 1H), 7.78(s, 1H), 7.387.48(m, 5H), 0.26(s, 9H) |
87% | With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h; | (Step 2)<strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) obtained in Step 1 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL), and thereto palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added. The mixture was heated under stirring for 3 hours at 100 C. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 5-chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.05 g, Yield 87%).1H-NMR (400 MHz, CDCl3); delta 9.78 (br s, 1H), 8.15 (s, 1H), 7.78 (s, 1H), 7.387.48 (m, 5H), 0.26 (s, 9H) |
87% | With palladium diacetate; triethylamine; lithium chloride; In N,N-dimethyl-formamide; at 100℃; for 3h; | <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With pyridine; In tetrahydrofuran; at 0 - 20℃; for 9h; | (Step 1)2-Iodo-4-chloro-6-nitro-phenylamine (10.0 g, 33.50 mmol) of was dissolved in 200 ml of tetrahydrofuran, and 3.97 g (50.25 mmol) of pyridine and 7.74 g (36.85 mmol) of trifluoroacetic anhydride were added. The mixture was stirred for 9 hours at 0 C.room temperature. At the end of reaction, the reaction mixture was diluted with water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and separated by column chromatography to obtain trifluoroacetamide 12.3 g (Yield 85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
336 mg (96%) | In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; | B. Synthesis of 4-chloro-6-iodo-1,2-phenylenediamine: To a stirred mixture of <strong>[123158-75-8]4-chloro-2-iodo-6-nitroaniline</strong> (389 mg, 1.305 mMol) in ethanol (10 mL) was added SnCl2 ·2H2 O (1.468 g, 6.526 mMol) in one portion. The mixture was refluxed at 80 C. (oil bath 90 C.) with stirring for 0.5 h to form a clear solution and then refluxing was continued for another 0.5 h. The solution was cooled to room temperature and ice water (20 g) was added. The pH was adjusted to pH~7 and the mixture was extracted with ethyl acetate. The extract was dried over MgSO4, and evaporated to dryness to give 336 mg (96%) of 4-chloro-6-iodo-1,2-phenylenediamine, as a brown solid. NMR (1 H, CDCl3): delta3.536 (s, 2H); 3.763 (s, 2H); 7.165 (d, 1H, J=1.8 Hz); 6.671 (d, 1H, J=1.8 Hz). |
Tags: 123158-75-8 synthesis path| 123158-75-8 SDS| 123158-75-8 COA| 123158-75-8 purity| 123158-75-8 application| 123158-75-8 NMR| 123158-75-8 COA| 123158-75-8 structure
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H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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