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CAS No. : | 22162-15-8 | MDL No. : | MFCD12755934 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PXSWIWNWHAUARP-UHFFFAOYSA-N |
M.W : | 167.16 | Pubchem ID : | 21345674 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.36 |
TPSA : | 66.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 1.66 |
Log Po/w (WLOGP) : | 1.24 |
Log Po/w (MLOGP) : | 0.68 |
Log Po/w (SILICOS-IT) : | -0.03 |
Consensus Log Po/w : | 1.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.16 |
Solubility : | 1.16 mg/ml ; 0.00692 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.66 |
Solubility : | 0.365 mg/ml ; 0.00218 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.99 |
Solubility : | 1.72 mg/ml ; 0.0103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
90% | With manganese(IV) oxide In dichloromethane at 20℃; | General procedure: Adapting literature known protocol (Aoyama, et al., Synlett, 1998, 35-36), commercial activated manganese(IV) oxide (MnO2) (250-275 mmol) is added at room temperature to a solution of the benzylic alcohol (25 mmol) in dichloromethane (DCM) (100 mL). The reaction mixture is stirred for 12-24 h. The reaction is monitored by TLC and/or LCMS to completion. The reaction mixture is filtered over a short path of Celite® 545 and the filtrate is concentrated under reduced pressure. The material is often of sufficient purity to be used directly in the next step without further isolation and purification. If needed, the crude material is purified by silica gel column chromatography or is re-crystallized 2-Methyl-4-nitro-benzaldehyde (2b) Following the General Procedure of Description 2 (Variant B), 2-methyl-4-nitro-benzaldehyde (2b) was prepared from 2-methyl-4-nitro-phenyl)methanol (1a) (8.4 g, 50.3 mmol) in the presence of manganese dioxide (MnO2) (48.1 g, 553 mmol). Work-up afforded 7.5 g (90percent yield) of the target compound (7b) as a yellow solid. The material was of sufficient purity to be used directly in the next step without further isolation and purification. Rf: ˜0.58 (EtOAc/Hxn=1:2 v/v). 1H NMR (300 MHz, CDCl3): δ 10.39 (s, 1H), 8.20 (dd, J=8.4, 2.1 Hz, 1H), 8.14 (br. s, 1H), 7.98 (d, J=8.1 Hz, 1H), 2.79 (s, 3H) ppm. The spectroscopic data correspond to the data provided in the literature. The compound is also commercially available. |
90% | With manganese(IV) oxide In dichloromethane at 20℃; | General procedure: Variant B: Adapting literature known protocol (Aoyama, et al., Synlett, 1998, 35- 36), commercial activated manganese(IV) oxide (Mn02) (250-275 mmol) is added at room temperature to a solution of the benzylic alcohol (25 mmol) in dichloromethane (DCM) (100 mL). The reaction mixture is stirred for 12-24 h. The reaction is monitored by TLC and/or LCMS to completion. The reaction mixture is filtered over a short path of Celite® 545 and the filtrate is concentrated under reduced pressure. The material is often of sufficient purity to be used directly in the next step without further isolation and purification. If needed, the crude material is purified by silica gel column chromatography or is re-crystallized. Following the General Procedure of Description 2 (Variant B), 2-methyl-4-nitro- benzaldehyde (2b) was prepared from 2-methyl-4-nitro-phenyl)methanol (la) (8.4 g, 50.3 mmol) in the presence of manganese dioxide (Mn02) (48.1 g, 553 mmol). Work-up afforded 7.5 g (90percent yield) of the target compound (2b) as a yellow solid. The material was of sufficient purity to be used directly in the next step without further isolation and purification. Rf. -0.58 (EtOAc/Hxn = 1 :2 v/v). 1H MR (300 MHz, CDC13): δ 10.39 (s, 1H), 8.20 (dd, J = 8.4, 2.1 Hz, 1H), 8.14 (br. s, 1H), 7.98 (d, J= 8.1 Hz, 1H), 2.79 (s, 3H) ppm. The spectroscopic data correspond to the data provided in the literature. The compound is also commercially available |
13 g | With manganese(IV) oxide In dichloromethane at 40℃; for 2 h; | A flask was charged with (2-methyl-4-nitro-phenyl)-methanol (16.7 g, 0.100 mol) (334 mL), to manganese(IV) oxide (5 μm, 102.3 g, 1.00 mol), and CH2Cl2 (334 mL). The stirred mixture was heated at 40° C. for at least 2 h or until in-process HPLC analysis showed that conversion was greater than 95percent. The cooled mixture was filtered through a celite cake (8 g) loaded onto a fritted funnel and the filter cake was rinsed with CH2Cl2 (340 mL). The filtrate and wash were concentrated under reduced pressure to dryness to afford the title compound as an amorphous solid (13.0 g, 78percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With calcium carbonate In water | ||
Multi-step reaction with 2 steps 1: AcOH / 7 h / 120 °C 2: NaOH / methanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With Trimethyl borate; dimethylsulfide borane complex; In tetrahydrofuran; at 65℃; for 2h;Inert atmosphere; | A flask was purged with nitrogen and charged with <strong>[1975-51-5]2-methyl-4-nitro-benzoic acid</strong> (45.3 g, 0.25 mol), trimethyl borate (103.9 g, 1.00 mol), and tetrahydrofuran (906 mL). Neat borane dimethyl sulfide complex (39.9 g, 49.8 mL, 0.525 mol) was added drop-wise at 20-35 C. over at least 30 min. An exotherm and effervescence were observed during this addition. When the addition was complete, the reaction mixture was stirred at 65 C. for at least 2 h or until in-process HPLC analysis showed that conversion was greater than 97%. The batch was quenched with cooling by drop-wise addition of methanol (46 mL), followed by a solution of 12.1 N aqueous hydrochloric acid (97 g, 82.1 mL, 1.00 mol) in water (138 mL) over at least 30 min. Batch temperature was held at 20-35 C. during quench; an exotherm and effervescence were observed during the quench. The mixture was stirred at 50 C. for at least 1 h and concentrated under reduced pressure to a volume of 230 mL (to remove tetrahydrofuran). The concentrate was diluted with water (453 mL) and extracted with ethyl acetate (2×453 mL). The organic layer was washed with saturated aqueous sodium chloride solution (230 mL), dried over anhydrous magnesium sulfate (23 g), filtered, and concentrated in vacuo to dryness to give the title compound as a beige solid (41 g, 98% yield). |
To a solution of <strong>[1975-51-5]2-methyl-4-nitrobenzoic acid</strong> (5 g, 27.6 mmol, Aldrich) in THF) (95 ml) was added dropwise 1.0 M borane-tetrahydrofuran complex (55 ml, 55.0 mmol, Aldrich) at ambient temperature under nitrogen. The resulting red solution was heated to 80 0C for 2 h. To the solution at ambient temperature was added methanol (30 ml) and then heated to 80 0C for 30 min. The solvent was evaporated in vacuo to leave a yellow oil. The residue was dissolved in methanol (80 ml) and the solvent evaporated in vacuo to leave (2-methyl-4-nitrophenyl)methanol as a yellow solid (4.73 g). | ||
9 g | With borane-THF; In tetrahydrofuran; methanol; at 80℃; for 6.66667h; | (A) (2-Methyl-4-nitrophenyl)methanol A 1.0 M solution of borane-THF complex in THF (110 mL) was added dropwise to a mixture of <strong>[1975-51-5]2-methyl-4-nitrobenzoic acid</strong> (10 g) and THF (200 mL) at room temperature, and the resulting mixture was stirred at 80 C. for 5.5 hours. The reaction mixture was cooled to room temperature, then methanol (50 mL) was added thereto, and the mixture was stirred at room temperature 10 minutes and then stirred at 80 C. for 1 hour. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue. The reaction mixture was washed with 0.5 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain the title compound (9.0 g). 1H NMR (300 MHz, CDCl3) delta 1.81 (1H, t, J=5.6 Hz), 2.40 (3H, s), 4.80 (2H, d, J=5.6 Hz), 7.62 (1H, d, J=8.4 Hz), 8.00-8.11 (2H, m). |
9 g | With borane-THF; In tetrahydrofuran; at 80℃; for 5.5h; | At room temperature,A 1.0 M borane-THF complex was addedTHF solution (110 mL)Was added dropwise to a mixture of <strong>[1975-51-5]2-methyl-4-nitrobenzoic acid</strong> (10 g) and THF (200 mL)The resulting mixture was stirred at 80 C for 5.5 hours.The reaction mixture was cooled to room temperature,Methanol (50 mL) was added thereto, and the mixture was stirred at room temperature for 10 minutes and then at 80 C for 1 hour.The solvent was removed by distillation under reduced pressure, and ethyl acetate was added to the residue. The reaction mixture was washed with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain the title compound (9.0 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With manganese(IV) oxide; In dichloromethane; at 20℃; | General procedure: Adapting literature known protocol (Aoyama, et al., Synlett, 1998, 35-36), commercial activated manganese(IV) oxide (MnO2) (250-275 mmol) is added at room temperature to a solution of the benzylic alcohol (25 mmol) in dichloromethane (DCM) (100 mL). The reaction mixture is stirred for 12-24 h. The reaction is monitored by TLC and/or LCMS to completion. The reaction mixture is filtered over a short path of Celite 545 and the filtrate is concentrated under reduced pressure. The material is often of sufficient purity to be used directly in the next step without further isolation and purification. If needed, the crude material is purified by silica gel column chromatography or is re-crystallized2-Methyl-4-nitro-benzaldehyde (2b) Following the General Procedure of Description 2 (Variant B), 2-methyl-4-nitro-benzaldehyde (2b) was prepared from 2-methyl-4-nitro-phenyl)methanol (1a) (8.4 g, 50.3 mmol) in the presence of manganese dioxide (MnO2) (48.1 g, 553 mmol). Work-up afforded 7.5 g (90% yield) of the target compound (7b) as a yellow solid. The material was of sufficient purity to be used directly in the next step without further isolation and purification. Rf: ?0.58 (EtOAc/Hxn=1:2 v/v). 1H NMR (300 MHz, CDCl3): delta 10.39 (s, 1H), 8.20 (dd, J=8.4, 2.1 Hz, 1H), 8.14 (br. s, 1H), 7.98 (d, J=8.1 Hz, 1H), 2.79 (s, 3H) ppm. The spectroscopic data correspond to the data provided in the literature. The compound is also commercially available. |
90% | With manganese(IV) oxide; In dichloromethane; at 20℃; | General procedure: Variant B: Adapting literature known protocol (Aoyama, et al., Synlett, 1998, 35- 36), commercial activated manganese(IV) oxide (Mn02) (250-275 mmol) is added at room temperature to a solution of the benzylic alcohol (25 mmol) in dichloromethane (DCM) (100 mL). The reaction mixture is stirred for 12-24 h. The reaction is monitored by TLC and/or LCMS to completion. The reaction mixture is filtered over a short path of Celite 545 and the filtrate is concentrated under reduced pressure. The material is often of sufficient purity to be used directly in the next step without further isolation and purification. If needed, the crude material is purified by silica gel column chromatography or is re-crystallized. Following the General Procedure of Description 2 (Variant B), 2-methyl-4-nitro- benzaldehyde (2b) was prepared from 2-methyl-4-nitro-phenyl)methanol (la) (8.4 g, 50.3 mmol) in the presence of manganese dioxide (Mn02) (48.1 g, 553 mmol). Work-up afforded 7.5 g (90% yield) of the target compound (2b) as a yellow solid. The material was of sufficient purity to be used directly in the next step without further isolation and purification. Rf. -0.58 (EtOAc/Hxn = 1 :2 v/v). 1H MR (300 MHz, CDC13): delta 10.39 (s, 1H), 8.20 (dd, J = 8.4, 2.1 Hz, 1H), 8.14 (br. s, 1H), 7.98 (d, J= 8.1 Hz, 1H), 2.79 (s, 3H) ppm. The spectroscopic data correspond to the data provided in the literature. The compound is also commercially available |
13 g | With manganese(IV) oxide; In dichloromethane; at 40℃; for 2.0h; | A flask was charged with (2-methyl-4-nitro-phenyl)-methanol (16.7 g, 0.100 mol) (334 mL), to manganese(IV) oxide (5 mum, 102.3 g, 1.00 mol), and CH2Cl2 (334 mL). The stirred mixture was heated at 40 C. for at least 2 h or until in-process HPLC analysis showed that conversion was greater than 95%. The cooled mixture was filtered through a celite cake (8 g) loaded onto a fritted funnel and the filter cake was rinsed with CH2Cl2 (340 mL). The filtrate and wash were concentrated under reduced pressure to dryness to afford the title compound as an amorphous solid (13.0 g, 78% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In methanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-bromosuccinimide; 2,2'-dimethyl-2,2'-diazenediyldipropanenitrile / ethyl acetate / 27.5 h / Heating 2: AcOH / 7 h / 120 °C 3: NaOH / methanol / 2 h / Heating | ||
Multi-step reaction with 2 steps 1: NBS, (PhCO)2O2 / CCl4 2: CaCO3 / H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1.38 g / MnO2 / acetone / 20 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 44 percent / diethyl ether; hexane; tetrahydrofuran / -78 °C 3.1: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1.38 g / MnO2 / acetone / 20 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 44 percent / diethyl ether; hexane; tetrahydrofuran / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1.38 g / MnO2 / acetone / 20 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 44 percent / diethyl ether; hexane; tetrahydrofuran / -78 °C 3.1: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 20 °C 4.1: benzotriazol-1-ol; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 1.5 h / 20 °C 4.2: 72 percent / Et3N / dimethylformamide / 20 °C 5.1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 20 °C 6.1: 97 percent / NaBH4 / ethanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 1.38 g / MnO2 / acetone / 20 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 44 percent / diethyl ether; hexane; tetrahydrofuran / -78 °C 3.1: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 20 °C 4.1: benzotriazol-1-ol; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 1.5 h / 20 °C 4.2: 72 percent / Et3N / dimethylformamide / 20 °C 5.1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 20 °C 6.1: 97 percent / NaBH4 / ethanol / 20 °C 7.1: 91 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1.38 g / MnO2 / acetone / 20 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 44 percent / diethyl ether; hexane; tetrahydrofuran / -78 °C 3.1: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 20 °C 4.1: benzotriazol-1-ol; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 1.5 h / 20 °C 4.2: 72 percent / Et3N / dimethylformamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1.38 g / MnO2 / acetone / 20 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 44 percent / diethyl ether; hexane; tetrahydrofuran / -78 °C 3.1: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 20 °C 4.1: benzotriazol-1-ol; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 1.5 h / 20 °C 4.2: 72 percent / Et3N / dimethylformamide / 20 °C 5.1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzene; tetrahydrofuran / 16 h / 20 °C 2: CS2CO3 / dimethylformamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: benzene; tetrahydrofuran / 16 h / 20 °C 2: CS2CO3 / dimethylformamide / 16 h / 20 °C 3: 80 percent / NaOH; H2O / methanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: benzene; tetrahydrofuran / 16 h / 20 °C 2: CS2CO3 / dimethylformamide / 16 h / 20 °C 3: 80 percent / NaOH; H2O / methanol / 1 h / 20 °C 4: dimethylformamide / 0.17 h / 50 °C 5: dimethylformamide / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: benzene; tetrahydrofuran / 16 h / 20 °C 2: CS2CO3 / dimethylformamide / 16 h / 20 °C 3: 80 percent / NaOH; H2O / methanol / 1 h / 20 °C 4: dimethylformamide / 0.17 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: benzene; tetrahydrofuran / 16 h / 20 °C 2: CS2CO3 / dimethylformamide / 16 h / 20 °C 3: 80 percent / NaOH; H2O / methanol / 1 h / 20 °C 4: dimethylformamide / 0.17 h / 50 °C 5: dimethylformamide / 2 h / 20 °C 6: aq. phosphate buffer; propan-2-ol / 20 °C / Radiolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 3h; | s27.2 Step 2: Synthesis of 1-(bromomethyl)-2-methyl-4-nitrobenzene. To a solution of (2-methyl-4-nitrophenyl)methanol (9.0 g, 53.84 mmol) in CH2Cl2 (100.0 mL) was added PPh3 (21.2 g, 80.76 mmol) and CBr4 (26.8 g, 80.76 mmol) at 0^ . The resulting mixture was stirred at room temperature for 3 h. After the reaction was completed, the resulting mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography with petroleum ether/ethyl acetate (87/13, v/v) to afford 1-(bromomethyl)-2-methyl-4-nitrobenzene (6.0 g, 48%) as a yellow solid. |
48% | With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 3h; | s27.2 Step 2: Synthesis of 1-(bromomethyl)-2-methyl-4-nitrobenzene. To a solution of (2-methyl-4-nitrophenyl)methanol (9.0 g, 53.84 mmol) in CH2Cl2 (100.0 mL) was added PPh3 (21.2 g, 80.76 mmol) and CBr4 (26.8 g, 80.76 mmol) at 0^ . The resulting mixture was stirred at room temperature for 3 h. After the reaction was completed, the resulting mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography with petroleum ether/ethyl acetate (87/13, v/v) to afford 1-(bromomethyl)-2-methyl-4-nitrobenzene (6.0 g, 48%) as a yellow solid. |
With phosphorus tribromide In dichloromethane at 20℃; Inert atmosphere; Cooling with ice; | 32 To a solution of (2-methyl-4-nitrophenyl)methanol (2 g, 12 mmol) in DCM (25 ml) in an ice-water bath under nitrogen was added a solution of phosphorous tribromide (1.13 ml, 12 mmol, Aldrich) in DCM (20 ml). The resulting solution was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was poured onto ice-water (70 ml) and saturated sodium hydrogen carbonate (30 ml). The mixture was diluted with DCM (50 ml) and the phases separated. The aqueous extract was washed with DCM (20 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to leave 1-(bromomethyl)-2-methyl-4-nitrobenzene as a yellow solid (1.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: manganese(IV) oxide / dichloromethane / 2 h / 40 °C 2: aluminum oxide / 3 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 2 h / 40 °C 2: aluminum oxide / 3 h / 100 °C / Inert atmosphere 3: hydrogen; 10 wt% platinum on carbon; palladium 10% on activated carbon / methanol / 72 h / 55 - 60 °C / 3102.97 Torr / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: manganese(IV) oxide / dichloromethane / 2 h / 40 °C 2.1: aluminum oxide / 3 h / 100 °C / Inert atmosphere 3.1: hydrogen; 10 wt% platinum on carbon; palladium 10% on activated carbon / methanol / 72 h / 55 - 60 °C / 3102.97 Torr / Inert atmosphere 4.1: <i>tert</i>-butyl alcohol; N,N-dimethyl-formamide / 3 h / 75 °C / Inert atmosphere 4.2: 10 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: manganese(IV) oxide / dichloromethane / 2 h / 40 °C 2.1: aluminum oxide / 3 h / 100 °C / Inert atmosphere 3.1: hydrogen; 10 wt% platinum on carbon; palladium 10% on activated carbon / methanol / 72 h / 55 - 60 °C / 3102.97 Torr / Inert atmosphere 4.1: <i>tert</i>-butyl alcohol; N,N-dimethyl-formamide / 3 h / 75 °C / Inert atmosphere 4.2: 10 h / 80 °C 5.1: triethylamine / dichloromethane / 22 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: manganese(IV) oxide / dichloromethane / 2 h / 40 °C 2.1: aluminum oxide / 3 h / 100 °C / Inert atmosphere 3.1: hydrogen; 10 wt% platinum on carbon; palladium 10% on activated carbon / methanol / 72 h / 55 - 60 °C / 3102.97 Torr / Inert atmosphere 4.1: <i>tert</i>-butyl alcohol; N,N-dimethyl-formamide / 3 h / 75 °C / Inert atmosphere 4.2: 10 h / 80 °C 5.1: triethylamine / dichloromethane / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 1 h / Cooling with ice 1.2: 21 h / 10 - 35 °C 2.1: pyrographite; iron(III) chloride hexahydrate; hydrazine hydrate / tetrahydrofuran; methanol / 3 h / 70 °C | ||
Multi-step reaction with 2 steps 1.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice 1.2: 21 h / 20 °C / Cooling with ice 2.1: pyrographite; iron(III) chloride hexahydrate; hydrazine hydrate / tetrahydrofuran; methanol / 3 h / 20 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 1 h / Cooling with ice 1.2: 21 h / 10 - 35 °C 2.1: pyrographite; iron(III) chloride hexahydrate; hydrazine hydrate / tetrahydrofuran; methanol / 3 h / 70 °C 3.1: N,N-dimethyl-formamide; oxalyl dichloride / tetrahydrofuran / 1 h / 10 - 35 °C 3.2: 2 h / 10 - 35 °C | ||
Multi-step reaction with 3 steps 1.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice 1.2: 21 h / 20 °C / Cooling with ice 2.1: pyrographite; iron(III) chloride hexahydrate; hydrazine hydrate / tetrahydrofuran; methanol / 3 h / 20 - 70 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 3.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 1 h / Cooling with ice 1.2: 21 h / 10 - 35 °C 2.1: pyrographite; iron(III) chloride hexahydrate; hydrazine hydrate / tetrahydrofuran; methanol / 3 h / 70 °C 3.1: N,N-dimethyl-formamide; oxalyl dichloride / tetrahydrofuran / 1 h / 10 - 35 °C 3.2: 2 h / 10 - 35 °C 4.1: chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; ruphos; caesium carbonate / 1,2-dimethoxyethane; water / 18 h / 90 °C / Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice 1.2: 21 h / 20 °C / Cooling with ice 2.1: pyrographite; iron(III) chloride hexahydrate; hydrazine hydrate / tetrahydrofuran; methanol / 3 h / 20 - 70 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 3.2: 2 h / 20 °C 4.1: caesium carbonate; ruphos; chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct / 1,2-dimethoxyethane; water / 18 h / 20 - 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.8 g | Stage #1: (2-methyl-4-nitro-phenyl)methanol With methanesulfonyl chloride; triethylamine In tetrahydrofuran for 1h; Cooling with ice; Stage #2: morpholine In acetonitrile at 10 - 35℃; for 21h; | 109.B (B) 4-(2-Methyl-4-nitrobenzyl)morpholine (B) 4-(2-Methyl-4-nitrobenzyl)morpholine To a reaction mixture of (2-methyl-4-nitrophenyl)methanol (9.0 g), triethylamine (14.8 mL) and THF (100 mL), methanesulfonyl chloride (6.3 mL) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour. Water was added to the reaction mixture under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Acetonitrile (100 mL) and morpholine (23.6 mL) were added to the residue, and the reaction mixture was stirred at room temperature for 21 hours. The reaction mixture was concentrated into half the amount under reduced pressure, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (11.8 g). MS: [M+H]+236.9. |
11.8 g | Stage #1: (2-methyl-4-nitro-phenyl)methanol With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 20℃; for 1h; Cooling with ice; Stage #2: morpholine In acetonitrile at 20℃; for 21h; Cooling with ice; | 109.B 4-(2-methyl-4-nitrobenzyl)morpholine (2-methyl-4-nitrophenyl) methanol (9.0 g) under ice-Triethylamine (14.8 mL) and THF (100 mL)addPlus methanesulfonyl chloride(6.3 mL),The mixture was stirred at room temperature for 1 hour.Water was added to the reaction mixture under ice-cooling followed by extraction with ethyl acetate.The organic layer was washed with brine,Dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure.Acetonitrile (100 mL) and morpholine (23.6 mL) were added to the residue, and the reaction mixture was stirred at room temperature for 21 hours.The reaction mixture was concentrated to a half volume under reduced pressure and water was added thereto,Followed by extraction with ethyl acetate.The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure.The residue was purified by silica gel column chromatography (ethyl acetate / hexane) to give the title compound (11.8 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With Re2O7*SiO2 at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridinium chlorochromate; silica gel / dichloromethane / 20 °C 2.1: methanesulfonic acid / 90 °C 2.2: Reflux 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: pyridinium chlorochromate; silica gel / dichloromethane / 20 °C 2.1: methanesulfonic acid / 90 °C 2.2: Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: pyridinium chlorochromate; silica gel / dichloromethane / 20 °C 2.1: methanesulfonic acid / 90 °C 2.2: Reflux 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 1 h / 20 °C 4.1: recombinant human glutathione S-transferase P1 / aq. phosphate buffer; dimethyl sulfoxide / pH 7.4 / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With oxygen at 120℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: water monomer; iron(0); ammonia hydrochloride / methanol / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: water monomer; iron(0); ammonia hydrochloride / methanol / 1 h / 80 °C 6: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate methanesulfonate; Cs2CO3 / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate methanesulfonate; Cs2CO3 / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 6: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate methanesulfonate; Cs2CO3 / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 6: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C 7: tris(methyl)aluminum / tetrahydrofuran / 3 h / 0 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: isopropanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: isopropanol / 2 h / 20 °C 5: water monomer; iron(0); ammonia hydrochloride / ethanol / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2.1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3.1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4.1: isopropanol / 2 h / 20 °C 5.1: water monomer; iron(0); ammonia hydrochloride / ethanol / 3 h / 80 °C 6.1: isobutyl chloroformate; 4-methyl-morpholine / tetrahydrofuran / 0.25 h / 0 °C 6.2: 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: isopropanol / 16 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: isopropanol / 16 h / 25 °C 5: water monomer; iron(0); ammonia hydrochloride / methanol / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2.1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3.1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4.1: isopropanol / 16 h / 25 °C 5.1: water monomer; iron(0); ammonia hydrochloride / methanol / 1 h / 80 °C 6.1: isobutyl chloroformate; 4-methyl-morpholine / tetrahydrofuran / 0.25 h / 0 °C 6.2: 0.67 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate methanesulfonate; Cs2CO3 / toluene / 16 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: glacial acetic acid / 2 h / 85 °C 5: dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate methanesulfonate; Cs2CO3 / toluene / 16 h / 100 °C / Inert atmosphere 6: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 3 h / 0 - 20 °C 2.1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / water monomer; 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 3.1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4.1: glacial acetic acid / 2 h / 85 °C 5.1: dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate methanesulfonate; Cs2CO3 / toluene / 16 h / 100 °C / Inert atmosphere 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C 7.1: isobutyl chloroformate / tetrahydrofuran / 0.25 h / 0 °C 7.2: 1 h / 0 °C |
Tags: 22162-15-8 synthesis path| 22162-15-8 SDS| 22162-15-8 COA| 22162-15-8 purity| 22162-15-8 application| 22162-15-8 NMR| 22162-15-8 COA| 22162-15-8 structure
[ 54915-41-2 ]
(2-Methyl-6-nitrophenyl)methanol
Similarity: 0.94
[ 71176-55-1 ]
(5-Nitro-1,3-phenylene)dimethanol
Similarity: 0.93
[ 54915-41-2 ]
(2-Methyl-6-nitrophenyl)methanol
Similarity: 0.94
[ 71176-55-1 ]
(5-Nitro-1,3-phenylene)dimethanol
Similarity: 0.93
[ 54915-41-2 ]
(2-Methyl-6-nitrophenyl)methanol
Similarity: 0.94
[ 71176-55-1 ]
(5-Nitro-1,3-phenylene)dimethanol
Similarity: 0.93
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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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