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Structure of 5653-62-3
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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.
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CAS No. : | 5653-62-3 |
Formula : | C9H9NO2 |
M.W : | 163.17 |
SMILES Code : | N#CC1=CC=CC(OC)=C1OC |
MDL No. : | MFCD00001784 |
InChI Key : | LBXGBNHUNHWYRM-UHFFFAOYSA-N |
Pubchem ID : | 21862 |
GHS Pictogram: | ![]() |
Signal Word: | Danger |
Hazard Statements: | H302+H312-H315-H319-H331-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 |
Class: | 6.1 |
UN#: | 3439 |
Packing Group: | Ⅲ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.14 |
TPSA ? Topological Polar Surface Area: Calculated from | 42.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.28 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.83 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 1.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.51 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.9 |
Solubility | 2.07 mg/ml ; 0.0127 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.77 |
Solubility | 2.79 mg/ml ; 0.0171 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.73 |
Solubility | 0.305 mg/ml ; 0.00187 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) | Yes |
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 | -6.39 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 | 0.0 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) | 1.56 |
* 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 |
---|---|---|
With aluminum (III) chloride; triethylamine; In toluene; at 30 - 75℃; for 9.5h; | Preparation of 2, 3-dihydroxy benzoic acid form 2, 3-dimethoxy benzoic acid To a stirred solution of 2, 3-dimethoxy benzoic acid (lOOg; 0.549 mol) in dichloromethane (500 mL) and catalytic amount of DMF (~2 mL) at a temperature about 30-35°C, thionyl chloride (130.6g ; 1.102 mol) was added and stirred for a period of two hours. Reaction was monitored by TLC for completion of the starting material (NMT- 5percent).If reaction not completed added thionyl chloride (9.8 g; 0.823 mol). Upon completion of reaction, the reaction mass was quenched in to the -5°C chilled aqueous ammonia (580 mL) solution at a temperature below 15°C under stirring. The reaction mass was stirred at temperature 30-35°C over a period of 30 min. The separated organic fraction was concentrated under atmospheric distillation at below 50°C, charged toluene (100 ml) and co-distilled until the reaction mass moisture content become less than 0.5 percent. The obtained benzamide compound was dissolved in toluene (500 mL) at temperature about 30-35°C.To the reaction mass was added POCl3 (126.3 g; 0.824 mol).The temperature of the reaction mass was raised to 80-85°C and maintained over a period of 1 -2 hours for the completion of the reaction (Progress of the reaction was monitored by HPLC until the benzamide NMT 1.0 percent). If the reaction was not completed, added second lot of POCl3 (lO.lg; 0.06 mol) at 30-35°C. The reaction mass was cooled to a temperature about 30-35°C upon completion of the reaction. The reaction mixture was added to cold water (1000 mL) at 0-5°C.The organic fraction was separated and washed with 8percent sodium bicarbonate solution. The organic fraction was separated and azeotropic distilled at 110-115°C (until moisture content NMT 0.2 percent), after reaching moisture content to normal limit cooled the reaction mass temperature to 40°C and distilled reaction mass volume becomes ~3 volumes under vacuum at a temperature 40-50°C.After distillation cooled the reaction mass temperature to 30-35°C. In another RB flask charged toluene (160 ml), triethyl amine (199.7 g; 1.977 mol) at 30-35°C and stirred for 10 min. charged aluminum chloride (52.7 g 5; 1.977 mol) in five lots with the gap of 10 min between each lot addition (addition of aluminum chloride may raise the temperature to 45-50°C). The reaction mass temperature was raised to about 70-75 °C and added above reaction mass (methoxy compound) for 30 min. maintained the reaction mass at 70-75°C for 8 hr. Progress of the reaction was monitored by HPLC (until the 2,3-dimethoxybenzonitrile content 0.25 percent and 3-methoxy-2-hydroxybenzonitrile content 0.2 percent). If reaction was not completed added second lot of triethyl amine (27.7 g; 0.27 mol) and aluminum chloride (36.6 g; 0.27 mol).Upon completion of the reaction, the reaction mixture was cooled to 30-35°C and quenched with chilled aqueous HC1 (prepared by addition of water (500 ml) and Cone. HC1 (500 ml)) at 15°C. Stirred reaction mass at 25-30°C for about 30 min, filtered the obtained solids and separated aqueous and organic layers. Charged MIBK (320 ml) to the solids and charged above aqueous layer, filtered through celite and separated aqueous and organic layers. To the aqueous layer given MIBK (320+160 ml) extractions. To the combined organic layer given 20percent sodium chloride solution washing, organic layer was azeotropic distilled at 110°C to remove the water (moisture content NMT 0.2 percent).Cooled the reaction mass temperature to 30°C and filtered through 0.45 micron / 1 micron filter. To the filterate charged 1percent EDTA (400 ml), stirred for 30 min and filtered through 10 micron cloth. The organic fraction was separated and distilled off to obtain the residue. The residue was treated with dichloromethane (400 ml) and the solid obtained was filtered and dried under vacuum over 6 hr at 60-65°C to obtain the title compound 2, 3-dihydroxy benzonitrile. (56g, yield 75.4percent) Purity by HPLC 99.81 percent; Impurity A: 0.05percent Impurity B: 0.07 percent | |
56 g | With aluminum (III) chloride; triethylamine; In toluene; at 70 - 75℃; for 8h; | Example 1 Preparation of 2,3-dihydroxy benzoic acid form 2,3-dimethoxy benzoic acid [0069] To a stirred solution of 2,3-dimethoxy benzoic acid (100 g; 0.549 mol) in dichloromethane (500 mL) and catalytic amount of DMF (2 mL) at a temperature about 30-35° C., thionyl chloride (130.6 g; 1.102 mol) was added and stirred for a period of two hours. Reaction was monitored by TLC for completion of the starting material (NMT-5percent). If reaction not completed added thionyl chloride (9.8 g; 0.823 mol). Upon completion of reaction, the reaction mass was quenched in to the ?5° C. chilled aqueous ammonia (580 mL) solution at a temperature below 15° C. under stirring. The reaction mass was stirred at temperature 30-35° C. over a period of 30 min. The separated organic fraction was concentrated under atmospheric distillation at below 50° C., charged toluene (100 ml) and co-distilled until the reaction mass moisture content become less than 0.5percent. The obtained benzamide compound was dissolved in toluene (500 mL) at temperature about 30-35° C. To the reaction mass was added POCl3 (126.3 g; 0.824 mol). The temperature of the reaction mass was raised to 80-85° C. and maintained over a period of 1-2 hours for the completion of the reaction (Progress of the reaction was monitored by HPLC until the benzamide NMT 1.0percent). If the reaction was not completed, added second lot of POCl3 (10.1 g; 0.06 mol) at 30-35° C. The reaction mass was cooled to a temperature about 30-35° C. upon completion of the reaction. The reaction mixture was added to cold water (1000 mL) at 0-5° C. The organic fraction was separated and washed with 8percent sodium bicarbonate solution. The organic fraction was separated and azeotropic distilled at 110-115° C. (until moisture content NMT 0.2percent), after reaching moisture content to normal limit cooled the reaction mass temperature to 40° C. and distilled reaction mass volume becomes 3 volumes under vacuum at a temperature 40-50° C. After distillation cooled the reaction mass temperature to 30-35° C. In another RB flask charged toluene (160 ml), triethyl amine (199.7 g; 1.977 mol) at 30-35° C. and stirred for 10 min. charged aluminum chloride (52.7 g×5; 1.977 mol) in five lots with the gap of 10 min between each lot addition (addition of aluminum chloride may raise the temperature to 45-50° C.). The reaction mass temperature was raised to about 70-75° C. and added above reaction mass (methoxy compound) for 30 min. maintained the reaction mass at 70-75° C. for 8 hr. Progress of the reaction was monitored by HPLC (until the 2,3-dimethoxybenzonitrile content 0.25percent and 3-methoxy-2-hydroxybenzonitrile content 0.2percent). If reaction was not completed added second lot of triethyl amine (27.7 g; 0.27 mol) and aluminum chloride (36.6 g; 0.27 mol). Upon completion of the reaction, the reaction mixture was cooled to 30-35° C. and quenched with chilled aqueous HCl (prepared by addition of water (500 ml) and Conc. HCl (500 ml)) at 15° C. Stirred reaction mass at 25-30° C. for about 30 min, filtered the obtained solids and separated aqueous and organic layers. Charged MIBK (320 ml) to the solids and charged above aqueous layer, filtered through celite and separated aqueous and organic layers. To the aqueous layer given MIBK (320+160 ml) extractions. To the combined organic layer given 20percent sodium chloride solution washing, organic layer was azeotropic distilled at 110° C. to remove the water (moisture content NMT 0.2percent). Cooled the reaction mass temperature to 30° C. and filtered through 0.45 micron/1 micron filter. To the filterate charged 1percent EDTA (400 ml), stirred for 30 min and filtered through 10 micron cloth. The organic fraction was separated and distilled off to obtain the residue. The residue was treated with dichloromethane (400 ml) and the solid obtained was filtered and dried under vacuum over 6 hr at 60-65° C. to obtain the title compound 2,3-dihydroxy benzonitrile. (56 g, yield 75.4percent) [0070] Purity by HPLC 99.81percent; [0071] Impurity A: 0.05percent [0072] Impurity B: 0.07percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | To a stirred solution of 2,3-dimethoxybenzonitrile (25)(5.0 g, 30 mmol) in Et2O (12.5 mL) under N2 atmosphere was added methylmagnesium bromide (37percent in Et2O) (12.5 mL, 37 mmol).The mixture was stirred for 16 h, and then 50percent AcOH (20 mL) was added.After it was stirred for 30 min, the solution was poured into crushed ice, extracted with CH2Cl2, washed with 10percent Na2CO3 and then with water, dried over MgSO4 and concentrated.The crude was purified by column chromatography (SiO2, n-hexane: EtOAc=4:1) to give 26. Liquid; yield: 92.5percent; 1H-NMR (CDCl3, 200 MHz): delta 2.56 (s, 3H), 3.82 (s, 3H), 3.85 (s, 3H), 6.99-7.02 (m, 2H), 7.13-7.18 (m, 1H); 13C-NMR (CDCl3, 50 MHz): delta 31.18, 55.98, 61.29, 115.83, 120.80, 123.94, 133.62, 148.63, 153.04, 200.26; Anal. calcd for C10H12O3: C, 66.65; H, 6.71. Found: C, 66.60; H, 6.73. |
Tags: 5653-62-3 synthesis path| 5653-62-3 SDS| 5653-62-3 COA| 5653-62-3 purity| 5653-62-3 application| 5653-62-3 NMR| 5653-62-3 COA| 5653-62-3 structure
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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 |
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P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
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P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
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P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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H303 | May be harmful if swallowed |
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H305 | May be harmful if swallowed and enters airways |
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H311 | Toxic in contact with skin |
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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 |
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H335 | May cause respiratory irritation |
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H340 | May cause genetic defects |
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H351 | Suspected of causing cancer |
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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 |
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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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