Structure of 90924-12-2
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CAS No. : | 90924-12-2 |
Formula : | C10H9NO2 |
M.W : | 175.18 |
SMILES Code : | OCC1=CC(=NO1)C1=CC=CC=C1 |
MDL No. : | MFCD01928812 |
InChI Key : | CITYOBPAADIHAD-UHFFFAOYSA-N |
Pubchem ID : | 2763417 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.1 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 48.07 |
TPSA ? Topological Polar Surface Area: Calculated from | 46.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.18 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.68 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.6 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.16 |
Solubility | 1.2 mg/ml ; 0.00686 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.75 |
Solubility | 3.14 mg/ml ; 0.0179 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.58 |
Solubility | 0.0459 mg/ml ; 0.000262 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 | -6.53 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) | 2.6 |
* 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 |
---|---|---|
93% | With Jones reagent; In acetone; at 20℃; for 3h; | To a stirred solution of 8 (12 mg, 0.07 mmol) in acetone (0.4 ml) was added Jones? reagent (50 mul)at room temperature. Then, the mixture was stirred for 3 h. Then water (2 ml) was added, and theaqueous layer was extracted by diethyl ether (5 ml × 3). The organic layer was collected, washedwith water (5 ml × 3), dried over Na2SO4 and concentrated. The residue was recrystallized in CHCl3to afford the product (2a) as white solid (12 mg, 93.0 %). |
69% | With Jones reagent; In acetone; at 0℃; for 0.5h; | Jones reagent 8 N (0.3 mmol) was added dropwise to a solutionof compound 7 (0.1 mmol) in acetone (4 mL) in an ice bath. Thesolution was stirred for 30 min when TLC analysis showed the totalconsumption of the starting material. The solution was diluted inacetone (15 mL) filtered through celite and evapored under vacuum.The crude extract was purified by flash column chromatographyon silica (hexane:ethyl acetate 3:7) affording compound 23 as a white solid. Yield: 69%. Mp: 155.0-57.4 C. 1H NMR (300 MHz,CDCl3): delta = 7.78-7.90 (m, 2H, Ar), 7.45-7.55 (m, 3H, Ar), 7.25 (s, 1H,Isoxazole). 13C NMR (75 MHz, CDCl3): delta =166.9, 165.5, 162.3, 134.4,133.0, 132.8, 131.9, 130.7, 111.3. HRMS (ESI-TOF) m/z: [M- H]- Calcdfor C10H6NO3 188.0353; Found 188.0321. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triethylamine; In dichloromethane; at 50℃; for 2h; | To a stirred solution of 7 (10 mg, 0.06 mmol) in dichloromethane (DCM) (0.2 ml) was addedpropargyl alcohol (5 mul, 0.09 mmol) and Et3N (13 mul, 0.09 mmol) at room temperature. Then, themixture was heated to 50 C for 2 h. After the removal of the solvent, the residue was purifiedthrough a silica chromatography column (petroleum ether : EtOAc 3 : 1) to afford the product (8)as white solid (10 mg, 89.0 %). |
With (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; In water; at 65℃;Microwave irradiation; Green chemistry; | General procedure: In a round bottomed flask, a mixture of benzaldehyde 1a (0.027 g,0.25 mmol, 1.0 equiv) and NaOH (0.020 g, 0.50 mmol, 2.0 equiv) was added toa solution of hydroxylamine hydrochloride (0.0177 g, 0.25 mmol, 1.0 equiv) containing 5 mL of H2O. The reaction mixture was irradiated under microwave heating at 210W for 5 min at 65 C. The progress of the reaction was monitored by TLC. After completion, N-chlorosuccinimide (0.034 g, 0.25 mmol, 1.0 equiv) was added in small proportions for over 2 min, followed by microwave irradiation at same power for 2 min. After completion, phenylacetylene 3a (0.0255 g, 0.25 mmol, 1.0 equiv) and [Cu(phen)(PPh3)2]NO3 catalysts (0.0042 g, 2 mol%) was immediately added to the reaction mixture. Subsequently, the reaction mixture was irradiated under microwave for 5 min. The reaction progress was monitored by TLC. After completion, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (10 mL, twice). The combined organic layer was dried over anhydrous MgSO4. The combined filtrate was subjected to evaporation to obtain the crude compound, which was purified over silica gel column (60 - 120 mesh) using 1% ethyl acetate in hexane as eluent to obtain the corresponding 3,5-diphenylisoxazoles 4a as the product. | |
With sodium hydrogencarbonate; copper(II) sulfate; sodium L-ascorbate; In water; N,N-dimethyl-formamide; at 30℃; for 0.166667h;Microwave irradiation; | General procedure: The compounds were synthesised based on procedure reportedin the literature [38]. For the preparation of the imidoyl chloride, N-chlorosuccinimide (0.1 mmol) was slowly added to a solution of analdoxime (0.105 mmol) in DMF (1 mL) and the reaction was stirreduntil the starting material was not visible on the TLC analysis. After,the reaction was diluted with brine (15 mL), extracted with ethylether (3 x 10 mL), dried over Na2SO4, concentrated under vacuumand utilized without any purification in the next step. Following,propargylic alcohol (0.105 mmol), copper (II) sulphate (2 mol%),sodium ascorbate (10 mol%), sodium bicarbonate (0.4 mmol) and4mL of H2O:t-BuOH were added to the product obtained in the firstpart, and the reaction was further stirred for 4 h. Next, the reactionwas diluted with brine (15 mL), extracted with ethyl acetate(3 x 10 mL), dried over Na2SO4, concentrated under vacuum andthe crude extract was purified by flash column chromatography onsilica (hexane:ethyl acetate 6:4) yielding the expected product.After purification, they were compared via TLC analysis to therespecting compounds synthesized under microwave irradiation,when this comparison was desired, and characterized by NMR andmass spectrometry. 4.1.3. Structural characterization of compounds 6e314.1.3.1. 5-Hydroxymethyl-3-phenylisoxazole (6). Yield: 72%. YieldMW: 77%. Mp: 48.8-49.5 C. 1H NMR (300 MHz, Methanol-d4): delta 7.78-7.85 (m, 2H, Ar), 7.43-7.50 (m, 3H, Ar), 6.76 (s, 1H, Isoxazole),4.71 (s, 2H, CH2). 13C NMR (75 MHz, Methanol-d4):delta 171.7, 162.5, 130.1, 128.9, 128.8, 126.8, 100.0, 56.7. HRMS (ESITOF)m/z: [M+H]+ Calcd for C10H10NO2 176.0712; Found 176.0699 |
27.36 mg | With sodium hydrogencarbonate; copper(II) sulfate; sodium L-ascorbate; at 35℃; for 0.166667h;Microwave irradiation; Sealed tube; | General procedure: Under microwave irradiation, to a solution of oxime (1.03 mmol) inDMF (0.3 mL), was added NCS (1.1 mmol) and the mixture was irradiatedin a sealed tube during 1 min, at 35 C and 150 W. After that,propargylic alcohol (1.1 mmol), CuSO4 (0.01 mmol) dilute in 50.0 muL ofwater, sodium ascorbate (0.10 mmol) and NaHCO3 (4.10 mmol) wereadded to the tube. The reaction was irradiated again during 10 min., inthe same conditions above. When reaction time was over, the mixturewas diluted in EtOAc (20.0 mL) and washed with NaCl (2×20.0 mL).The organic phase was dried with anhydrous Na2SO4 and the solventwas removed under reduced pressure yielding the expected product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium chloride; triethylamine; In tetrahydrofuran; water; | Reference Example 68 Triethylamine (7.28 ml) was added to a solution of alpha-chlorobenzaldehyde oxime (4.04 g) and 2-propyn-1-ol (1.66 ml) in tetrahydrofuran (130 ml) and stirred at room temperature for 4 days. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain (3-phenyl-5-isoxazolyl)methanol (3.42 g, yield 75%) as colorless crystals. m.p. 48-49 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Production Example 17 {3-[4-(Trifluoromethoxy)phenyl]-1,2-oxazol-5-yl}methanol(2) N-Chlorosuccinimide (1.5 g) was added to a solution of N-hydroxy-1-[4-(trifluoromethoxy)phenyl]methaneimine (2.5 g) in chloroform (50 mL) and the mixture was stirred at room temperature for 1 hr. Propargylalcohol (0.8 mL) was added thereto, triethylamine (1.8 mL) was then added slowly, and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the resulting residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=94:6-50:50) to afford the title compound (1.3 g). 1H NMR (200 MHz, CHLOROFORM-d) d ppm 4.81-4.88 (m, 2H), 6.54-6.58 (m, 1H), 7.27-7.37 (m, 2H), 7.79-7.89 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With thionyl chloride; sodium chloride; In water; toluene; | Reference Example 70 Thionyl chloride (2.41 ml) was added to a solution of (3-phenyl-5-isoxazolyl)methanol (2.89 g) in toluene (10 ml) and stirred at 60 C. for 1 hour. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 5-(chloromethyl)-3-phenylisoxazole (2.75 g, yield 86%) as pale-brown crystals. m.p. 69-70 C. |
With thionyl chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of ?a? derivatives in freshly distilled CH2Cl2 under N2 atmosphere, at roomtemperature, thionyl chloride (1.5 eq) was added. The reactions were monitored by TLC and, at thetotal consumption of the starting material, they were quenched with cold water and extracted withCH2Cl2. Next, the crude products were solubilized in DMF followed by addition of sodium azide (1.5eq). The reactions were kept at room temperature until TLC analyses indicated the disappearance ofthe starting material, then, they were quenched with water and extracted with EtOAc. In the last step,the crude azide derivatives were solubilized in THF followed by addition of triphenylphosphine (1.5 eq).The reactions were maintained overnight at room temperature, quenched by addition of aqueousNa2CO3 [5% (m/v)] and extracted with EtOAc. The crude amine derivatives (compound d) were usedfor the synthesis of the isoxazolyl-sulfonamide derivatives 1-20 without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine; sodium hydrogencarbonate; In ethanol; water; benzene; at 20℃; for 9h; | General procedure: 3-Substituted isoxazole-5-carbaldehydes were synthesized according to reported procedures.37 (3-Phhenylisoxazol-5-yl)methanols (5.0 mmol) were dissolved into benzene (10 mL). An aqueous solution of sodium bicarbonate (13 mL, 1.2 mol/L) was added into the benzene slurry at room temperature. Then, the mixed solid TEMPO (0.5 mmol) was added and solid iodine (10 mmol) dissolved in alcohol was added into the reaction mixture. The reaction mixture was then aged for 10-12 h at room temperature; the reaction was monitored by TLC. The crude product was diluted with ethyl acetate (15 mL). The batch was washed with Na2S2O3 and transferred to a separatory funnel, and the aqueous layer was extracted with ethyl acetate (210 mL). The organic layers were mixed and dried over anhydrous sodium sulfate for 30 min, filtrated and evaporated under vacuum to give the crude product which was purified by column chromatography (silica gel, 200e300 mesh) using petroleum ether/ethyl acetate(4r5: 1) to furnish the product. The yields of obtained 3-substituted isoxazole-5-carbaldehydes products were 58-92%. |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate;Reflux; | A solution of (3-phenylisoxazol-5-yl)methanol (10.0 g) and 2-iodoxybenzoic acid (24.0 g) in ethyl acetate (350 mL) was refluxed overnight. The mixture was cooled to room temperature, filtered and concentrated. The resulting solids were triturated (hexane: diethyl ether = 1: 1) to obtain the title compound (8.22 g) having the following physical data. 1H NMR (DMSO-de): delta 9.97 (s, IH), 8.06-7.91 (m, 3H), 7.64-7.47 (m, 3H). | |
With Jones reagent; In acetone; at 0℃; for 0.583333h; | General procedure: (3-Arylisoxazol-5-yl)methanol 118,19 ( 4 mmol) was taken in dry acetone and cool to 0 oC and added the Jones reagent (CrO3+H2SO4+Acetone) (4 mmol) slowly over 15 minutes. The reaction mixture was stirred for 20 minutes at 0 oC. After completion of reaction, the reaction mixture was filtered through the short pad of celite, collected the filtrate, and concentrated under vacuum. The residue was purified by passing through a column packed with silica gel using petroleum ether/EtOAc (8:2) as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With silver tetrafluoroborate; phenol; In tetrahydrofuran; for 1h;Reflux; | General procedure: To a solution of alkynyl oxime ether 1 (0.15 mmol) in THF (5 mL) were added phenol (28 mg, 0.3 mmol) and AgBF4 (5.8 mg, 0.03 mmol), with a drying tube filled with silica gel at room temperature. After being stirred at reflux for 1-12 h (TLC monitoring), the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/AcOEt=3-10:1) to afford isoxazole 3. The physical and spectroscopic data of 3a5 and 3j12h were in accord with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.8% | (2) 3-phenyl-5-hydroxymethyl-isoxazole10.0 mmol of benzaldehyde oxime and30 mL of dry dichloromethane were placed in a 250 mL single-necked roundEP2 752 413 A18510152025303540455055bottom flask. 1.60g (12.0 mmol) of N-chlorosuccinimide (NCS) was added under stirring. After NCS was completelydissolved by slightly heating, 0.56g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 mL solution of10.1g (10.0 mmol) of triethylamine in dichloromethane. After the addition was complete, the system was refluxed.After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydroussodium sulfate, and seperated by column chromatography (Vpetroleum ether: Vethyl acetate = 5:1 - 2:1) to give 3-phenyl-5-hydroxymethyl- isoxazole in 76.8% yield.(3) 3-phenyl-5-aminomethyl-isoxazole | |
76.8% | With N-chloro-succinimide; triethylamine; In dichloromethane;Reflux; | 10.0 mmol of benzaldehyde oxime and 30 mL of dry dichloromethane were placed in a 250 mL single-necked round-bottom flask. 1.60 g (12.0 mmol) of N-chlorosuccinimide (NCS) was added under stirring. After NCS was completely dissolved by slightly heating, 0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 mL solution of 10.1 g (10.0 mmol) of triethylamine in dichloromethane. After the addition was complete, the system was refluxed. After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1) to give 3-phenyl-5-hydroxymethyl-isoxazole in 76.8% yield. |
76.8% | With N-chloro-succinimide; triethylamine; In dichloromethane; at 0℃;Reflux; | The benzaldehyde oxime 10.0mmol dry dichloromethane was added 30mL and 250mL single-necked round-bottomed flask was added with stirring 1.60g (12.0mmol) N- chlorosuccinimide (NCS), heating slightly to dissolve all the NCS, was added dropwise 0.56g (10.0mmol) 2- propynyl-1-ol, followed by the slow dropwise added 20mL dichloromethane solution containing 10.1g (10.0mmol) of triethylamine, and refluxed after addition. After TLC detection, the mother liquor was washed with water, dried over anhydrous sodium sulfate and separated by column chromatography (V: petroleum ether: V ethyl acetate 5: 1-2: 1) to give 3-phenyl-5-hydroxymethylisoxazole , Yield 76.8%. |
76.8% | With N-chloro-succinimide; triethylamine; In dichloromethane; at 0℃;Reflux; | 10.0 mmol of formaldoxime and 30 mL of dry dichloromethane were added to a 250 mL single-neck round bottom flask, 1.60 g (1.0 mmol) of N-chlorosuccinimide (NCS) was added with stirring, after slightly heating until all the NCS was dissolved, 0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise, soon afterwards, 20 mL of a dichloromethane solution containing 10.1 g (10.0 mmol) of triethylamine was slowly added dropwise. After the addition, the system was refluxed. After tlc detection reaction is completed, the mother liquid washing, dried over anhydrous sodium sulfate, and separated by column (V petroleum ether: V ethyl acetate 5:1~2:1) to obtain 3-phenyl-5-hydroxymethyl-isoxazole, yield 76.8 %. |
With N-chloro-succinimide; triethylamine; In dichloromethane; at 0℃;Reflux; | (2) Synthesis of 3-phenyl-5-hydroxymethyl-isoxazole 10.0 mmol of Benzaldehyde oxime and 30 ml of dry dichloromethane were added into a 250 ml single-necked round-bottom flask. After the addition of 1.60g (12.0 mmol) of N-chlorosuccinimide (NCS) under stirring, the mixture was slightly heated until NCS was completely dissolved. 0.56g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 ml solution of triethylamine in dichloromethane containing 10.1g (10.0 mmol) of triethylamine was slowly added dropwise. After the addition was complete, the system was refluxed. After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydrous sodium sulfate and was separated on column (Vpetroleum ether: Vethylacetate = 5:1 - 2:1) to give 3-phenyl-5-hydroxymethyl-isoxazole in 76.8% yield. | |
General procedure: To a solution of aldoximes (20 mmol) in N,N-dimethylformamide (DMF; 15 mL), N-chlorosuccinimide (NCS; 20.2 mmol, 2.7 g) was added under glacial bath conditions. Triethylamine (1.5 mmol, 4.17 mL)was added to the reaction solution followed by propargyl alcohol (60 mmol, 3.5 mL). The mixture was stirred at ambient temperature until the reaction was complete as monitored by TLC monitoring (ethyl acetate/petroleum ether = 1 : 2). Following the reaction, the slurry was extracted with ethyl acetate.The organic layers were dried over anhydrous sodium sulphate, filtered and then evaporated under vacuum to provide the crude product which was purified by column chromatography (silica gel, 200-300 mesh; Merck, Germany) to furnish the product with a 44-62 % yield. | ||
With N-chloro-succinimide; triethylamine; In dichloromethane;Reflux; | The 10.0 mmol benzaldehyde oxime waning and 30mL of dry dichloromethane was added 250mL single burning mouth round bottom flask was added with stirring 1.60g (12.0mmol) N- chlorosuccinimide (NCS), slightly heated to dissolve all NCS after the dropwise addition of 0.56g (10.0mmol) 2- propynyl-1-ol, followed by the slow dropwise 20 mL of methylene chloride solution containing 10.18 (10.0 mmol) of triethylamine was added after completion of the reaction was refluxed for detecting .tlc after the mother liquor washed with water, dried over anhydrous sodium sulfate, column separation (V petroleum ether: V ethyl acetate 5:1-2:1) to give 3-phenyl-5-hydroxymethylisoxazole, yield 76.8% | |
General procedure: A mixture of a' (10.0 mmol) in CH2Cl2 was stirred at room temperature, NCS (1.60 g, 12.0 mmol) was then added. The resulted mixture was stirred at reflux and propynol (0.56 g, 10.0 mmol) was added dropwise. After 0.5 h, triethylamine (1.01 g, 10 mmol) was added dropwise and refluxed for another 4 h. After cooling, the reaction mixture was washed with water and evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography with petroleum ether/ethyl acetate as eluent to give intermediate b'. | ||
With N-chloro-succinimide; triethylamine; In dichloromethane;Reflux; | Add 10.0 mmol of benzaldehyde oxime and 30 mL of dry dichloromethane to a 250 mL single-neck round bottom flask.1.60 g (12.0 mmol) of N-chlorosuccinimide (NCS) was added with stirring.After slightly heating until the NCS is completely dissolved,0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise.Then 20 mL of a dichloromethane solution containing 10.1 g (10.0 mmol) of triethylamine was slowly added dropwise.After the addition, the system is refluxed. After the TLC detection reaction is completed,The mother liquor is washed,Dry over anhydrous sodium sulfate,Column separation (V petroleum ether: V ethyl acetate 5:1 ~ 2:1)That is, 3-phenyl-5-hydroxymethyl-isoxazole was obtained in a yield of 76.8%. |
Tags: 90924-12-2 synthesis path| 90924-12-2 SDS| 90924-12-2 COA| 90924-12-2 purity| 90924-12-2 application| 90924-12-2 NMR| 90924-12-2 COA| 90924-12-2 structure
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P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
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. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
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 |
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