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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 5460-31-1 |
Formula : | C7H7NO3 |
M.W : | 153.14 |
SMILES Code : | OC1=CC=CC([N+]([O-])=O)=C1C |
MDL No. : | MFCD00007241 |
InChI Key : | GAKLFAZBKQGUBO-UHFFFAOYSA-N |
Pubchem ID : | 79579 |
GHS Pictogram: | ![]() |
Signal Word: | Danger |
Hazard Statements: | H301-H315-H319-H412 |
Precautionary Statements: | P501-P273-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
Class: | 6.1 |
UN#: | 2446 |
Packing Group: | Ⅲ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.25 |
TPSA ? Topological Polar Surface Area: Calculated from | 66.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.36 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.36 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.07 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.46 |
Solubility | 0.535 mg/ml ; 0.0035 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -3.13 |
Solubility | 0.114 mg/ml ; 0.000745 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -1.57 |
Solubility | 4.08 mg/ml ; 0.0267 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) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
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 | -5.74 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 | 1.0 |
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 | 2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.64 |
* 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 |
---|---|---|
Intermediate 57To a solution of 2-methyl-3-nitrophenol (15.3 g, 100 mmol) in DMF (150 mL) was added sodium hydride (60% in mineral oil, 2.6 g, 1 10 mmol) at 0C and the mixture was stirred for 30 minutes at room temperature. Methyl iodide (28.4 g, 200 mmol) was added and the mixture was heated to 80 C for 5 hours. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3 times 100 mL). The combined ethyl acetate phases were dried over sodium sulphate and concentrated under vacuum to give a residue, which was purified by column chromatography on silica gel (PE:EtOAc = 5: 1 ). Evaporation afforded the title compound as a yellow solid (14.4 g). | ||
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 14.0h; | Methyl iodide (8.13 mL, 130.6 mmol) was added dropwise to a solution of 8 (10 g, 65.29 mmol) ,and potassium carbonate (18.05 g, 130.6 mmol) in anhydrous DMF (130 mL). The reaction mixture was stirred at rt for 14 h and quenched by the addition of H2O (250 mL). The aqueous phase was extracted with EtOAc (3 × 200 mL), the combined organic layers washed with water (100 mL), saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to give corresponding methyl ether as a colorless solid. Palladium on carbon (10%, 200 mg) was added to a solution of above product in EtOAc (130 mL). The suspension was stirred at rt for 6 h under a hydrogen atmosphere before it was filtered through a plug of celite and eluted with EtOAc (150 mL). The eluent was concentrated to afford 12 (8.59 g, 96% over two steps) as a colorless amorphous solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-chloro-succinimide; sulfuric acid; sodium sulfate; sodium nitrite; In water; acetonitrile; | 4. Preparation of 4-chloro-2-methyl-3-nitrophenol A slurry of 4-chloro-2-methyl-3-nitroaniline (20.9 g), water (200 mL), and fluroboric acid (86 mL) was heated to boiling until almost complete solution took place, then cooled to 0-5 C. A solution of sodium nitrite (8.11 g) in water (20 mL) was then added dropwise to the above mixture, and then the mixture was stirred in the cold for an additional 30 min. The precipitated diazonium salt was filterd off and washed with a little cold water. The wet diazonium salt was added all at once to a hot (100-120 C.) solution of water (230 mL), concentrated sulfuric acid (115 mL), and sodium sulfate (35 g), and allowed to stir for 4 hr. The reaction mixture was cooled to room temperature and extracted with ethyl ether (700 mL in two portions). The combined ether extracts were washed with saturated sodium chloride solution, then dried over magnesium sulfate. Evaporation afforded crude product (17.5 g), which was purified by flash chromatography on silica, eluding with methylene chloride to afford 7.6 g as a yellow solid. The phenol was also prepared by the NCS chlorination of 2-methyl-3-nitrophenol, in a manner similar to that described in Oberhauser, J. Org. Chem. (1997) 62:4504-4506, as follows. STR72 2-Methyl-3-nitrophenol (25.5 g), N-chlorosuccinimide (44.5 g), and trifluormethanesulfonic acid (50.0 g) were combined in dry acetonitrile (500 mL) and allowed to stir under an atmosphere of nitrogen at 75 C. for 1.5 hr. The reaction mixture was cooled to room temperature, diluted with ethyl ether (650 mL), washed with water, 10% sodium bisulfite solution, water, and finally saturated sodium chloride solution. Evaporation of the solvent afforded a crude material which was flash chromatographed on silica and eluted with acetone:hexane (1:9) to afford 16.8 g as a yellow solid. | |
With N-chloro-succinimide; sulfuric acid; sodium sulfate; sodium nitrite; In water; acetonitrile; | 4. Preparation of 4-chloro-2-methyl-3-nitrophenol A slurry of 4-chloro-2-methyl-3-nitroaniline (20.9 g), water (200 mL), and fluroboric acid (86 mL) was heated to boiling until almost complete solution took place, then cooled to 0-5C. A solution of sodium nitrite (8.11 g) in water (20 mL) was then added dropwise to the above mixture, and then the mixture was stirred in the cold for an additional 30 min. The precipitated diazonium salt was filterd off and washed with a little cold water. The wet diazonium salt was added all at once to a hot (100-120C) solution of water (230 mL), concentrated sulfuric acid (115 mL), and sodium sulfate (35 g), and allowed to stir for 4 hr. The reaction mixture was cooled to room temperature and extracted with ethyl ether (700 mL in two portions). The combined ether extracts were washed with saturated sodium chloride solution, then dried over magnesium sulfate. Evaporation afforded crude product (17.5 g), which was purified by flash chromatography on silica, eluding with methylene chloride to afford 7.6 g as a yellow solid. The phenol was also prepared by the NCS chlorination of 2-methyl-3-nitrophenol, in a manner similar to that described in Oberhauser, J. Org. Chem . (1997) 62 :4504-4506, as follows. 2-Methyl-3-nitrophenol (25.5 g), N-chlorosuccinimide (44.5 g), and trifluormethanesulfonic acid (50.0 g) were combined in dry acetonitrile (500 mL) and allowed to stir under an atmosphere of nitrogen at 75 C for 1.5 hr. The reaction mixture was cooled to room temperature, diluted with ethyl ether (650 mL), washed with water, 10% sodium bisulfite solution, water, and finally saturated sodium chloride solution. Evaporation of the solvent afforded a crude material which was flash chromatographed on silica and eluted with acetone:hexane (1:9) to afford 16.8 g as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With 2-(Dimethylamino)pyridine; acetic anhydride; triethylamine;palladium-carbon; In ethyl acetate; | EXAMPLE 2 Synthesis of 4-acetoxyindole A suspension of 3.24 g of trans-6-benzyloxy-2-nitro-beta-pyrrolindino -styrene (prepared from 2-methyl-3-nitrophenol by a procedure reported in Organic Synthesis, Coll. Vol. 7, 34, 1990) and 648 mg of 10% pd/C catalyst in 30 ml of ethyl acetate was shaken under hydrogen atmosphere and at 50 psi, for 5 hours. To this reaction mixture were added acetic anhydride (1.4 ml), triethylamine (2.1 ml) and dimethylaminopyridine (324 mg). The resultant mixture was stirred for 1 hour at room temperature. The catalyst was removed over a layer of Celite and the filtrate was evaporated under reduced pressure to give an oily residue to which crushed ice was added. The resulting white precipitate was collected by filtration to give 1.2 g (69% yield) of 4-acetoxyindole: mp 97-98 C.; H-NMR (300 MHz, DMSO-d6)delta 2.32 (s,3H), 6.31 (s,1H), 6.71 (d,1H,J=8Hz), 7.05 (t, 1H, J=8 Hz), 7.28 (d,1H,J=8Hz), 7.32 (s,1H), 11.27 (s,1H). |
Tags: 5460-31-1 synthesis path| 5460-31-1 SDS| 5460-31-1 COA| 5460-31-1 purity| 5460-31-1 application| 5460-31-1 NMR| 5460-31-1 COA| 5460-31-1 structure
A163381 [180628-74-4]
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A163381 [180628-74-4]
3-(Hydroxymethyl)-5-nitrophenol
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A204107 [20876-37-3]
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P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
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P230 | Keep wetted |
P231 | Handle under inert gas. |
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P233 | Keep container tightly closed. |
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P240 | Ground/bond container and receiving equipment. |
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P263 | Avoid contact during pregnancy/while nursing. |
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P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
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P285 | In case of inadequate ventilation wear respiratory protection. |
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Response | |
Code | Phrase |
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P304 | IF INHALED: |
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P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
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P378 | |
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P391 | Collect spillage. Hazardous to the aquatic environment |
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P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
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P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
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P370 + P378 | In case of fire: |
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H221 | Flammable gas |
H222 | Extremely flammable aerosol |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
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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 |
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H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
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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 |
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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 |
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