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CAS No. : | 53936-56-4 | MDL No. : | MFCD09970981 |
Formula : | C11H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GFBCWCDNXDKFRH-UHFFFAOYSA-N |
M.W : | 194.23 | Pubchem ID : | 11745519 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.45 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.16 |
TPSA : | 38.69 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) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 2.07 |
Log Po/w (XLOGP3) : | 2.4 |
Log Po/w (WLOGP) : | 2.3 |
Log Po/w (MLOGP) : | 1.53 |
Log Po/w (SILICOS-IT) : | 2.07 |
Consensus Log Po/w : | 2.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.74 |
Solubility : | 0.352 mg/ml ; 0.00181 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.85 |
Solubility : | 0.272 mg/ml ; 0.0014 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.46 |
Solubility : | 0.667 mg/ml ; 0.00344 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
52.7% | With pyridinium p-toluenesulfonate In dichloromethane at 10 - 25℃; for 16 h; Inert atmosphere | Under a nitrogen atmosphere, the compound (T-1) (19.1g, 227.0mmol) was dissolved in a p-toluenesulfonic acid pyridinium (PPTS) (5.7g, 22.7mmol) in dichloromethane (200ml) . After cooling to 10°C , the compound (T-7) (25.0g, 227.0mmol) was dropped slowly dichloromethane (100ml) solution. The reaction mixture is allowed to warm to 25°C. After stirring for 16 hours, poured into water (500ml). After the aqueous layer was extracted with dichloromethane, and the combined organic layer, water, saturated sodium hydrogen carbonate aqueous solution was washed successively with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, toluene: ethyl acetate = 5: 1) to give the compound (T-8) (23.2g, 119.7mmol, 52.7 percent) was obtained. |
43% | Inert atmosphere | Example 17 Step 1; To a reaction flask containing a mixture of hydroquinone (110 g, 1.0 mol), pTSA (9.5 g, 0.05 mol), and 1 L of diethyl ether was added DHP (84 g, 1.0 mol) over a period of 30 min with stirring under a nitrogen atmosphere. After stirring overnight with nitrogen bubbling, the solution was extracted twice with nitrogen-purged solutions of 22.5 g of NaOH in 300 mL of water (total: 1.12 mol). The combined aqueous NaOH solutions were extracted with 300 mL of diethyl ether and cooled to 0° C. with an ice bath. Sodium bicarbonate (5.0 g) was added, and the stirred solution was slowly acidified with 64 mL of acetic acid (1.12 mol). The resulting mixture was stored at -18° C. overnight and then allowed to warm up to 0° C. The precipitated product was washed three times with 300 mL of water and dried under vacuum. The yield was 84 g (43percent). NMR showed that the product had a structure consistent with 4-(tetrahydro-2H-pyran-2-yloxy) phenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 3 h; Autoclave | To a 1-liter autoclave, 56.3 g (198 mmol) of the compound (9-2), 2.8 g of a catalyst (5percent Pd/C), and 250 ml of ethanol were added. The resulting mixture was reacted at room temperature for 3 hours while the hydrogen pressure was maintained to be 0.4 MPa. After the catalyst had been removed by filtration, vacuum concentration was performed. Hereby, 38.5 g of the compound (9-3) was prepared (quantitative) |
82% | With aluminum oxide; hydrogen In ethyl acetate at 20℃; | According to this procedure several other bases were tested (see table). |
80% | With hydrogen; calcium carbonate In ethyl acetate at 20℃; | Example 2; Step 2; To a stirred solution of the product (30 g, 0.105 mol), calcium carbonate (2.79 g, 0.027 mol) and ethyl acetate (120 ml) was added palladium on carbon (3.6 g). The mixture was stirred at ambient temperature under hydrogen pressure until uptake of hydrogen ceased. The mixture was filtered and washed with ethyl acetate. The solvent was distilled off in vacuum. The evaporation residue was dissolved in alcohol (36 ml) and the product precipitated by the addition of water (144 ml). The slurry was cooled to 00C and stirred vigorously for 2 h. Precipitated product was filtered and washed with water, dried in vacuum to give 80percent of Deoxyarbutin with a purity of 99.8percent (area by HPLC). |
80% | With hydrogen; sodium carbonate In isopropyl alcohol at 20℃; | According to this procedure several other bases were tested (see table). |
80% | With hydrogen; calcium carbonate In ethanol; ethyl acetate at 20℃; | According to this procedure several other bases were tested (see table). |
78% | With hydrogen; calcium carbonate In ethanol at 20℃; | According to this procedure several other bases were tested (see table). |
77% | With hydrogen; calcium carbonate In isopropyl alcohol at 20℃; | According to this procedure several other bases were tested (see table). |
4.1 g | With pyridine; 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; ethanol at 50℃; for 8 h; | In a pressure-resistant container, 6.7 g of the compound represented by the formula (I-1-4) 70 mL of tetrahydrofuran, 20 mL of ethanol, 10 mL of pyridine, 0.7 g of 5percent palladium carbon (containing 60percent of water) was added, 0.5 MPa, And the mixture was heated and stirred at 50 ° C. for 8 hours. The palladium was removed by filtration and the solvent was distilled off. Dissolve in ethyl acetate, add 1percent hydrochloric acid, Washed sequentially with water and brine. Purification was carried out by column chromatography (alumina, ethyl acetate) 4.1 g of a compound represented by the formula (I-1-5) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.7% | With pyridinium p-toluenesulfonate; In dichloromethane; at 10 - 25℃; for 16h;Inert atmosphere; | Under a nitrogen atmosphere, the compound (T-1) (19.1g, 227.0mmol) was dissolved in a p-toluenesulfonic acid pyridinium (PPTS) (5.7g, 22.7mmol) in dichloromethane (200ml) . After cooling to 10C , the compound (T-7) (25.0g, 227.0mmol) was dropped slowly dichloromethane (100ml) solution. The reaction mixture is allowed to warm to 25C. After stirring for 16 hours, poured into water (500ml). After the aqueous layer was extracted with dichloromethane, and the combined organic layer, water, saturated sodium hydrogen carbonate aqueous solution was washed successively with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, toluene: ethyl acetate = 5: 1) to give the compound (T-8) (23.2g, 119.7mmol, 52.7 %) was obtained. |
43% | toluene-4-sulfonic acid; In diethyl ether;Inert atmosphere; | Example 17 Step 1; To a reaction flask containing a mixture of hydroquinone (110 g, 1.0 mol), pTSA (9.5 g, 0.05 mol), and 1 L of diethyl ether was added DHP (84 g, 1.0 mol) over a period of 30 min with stirring under a nitrogen atmosphere. After stirring overnight with nitrogen bubbling, the solution was extracted twice with nitrogen-purged solutions of 22.5 g of NaOH in 300 mL of water (total: 1.12 mol). The combined aqueous NaOH solutions were extracted with 300 mL of diethyl ether and cooled to 0 C. with an ice bath. Sodium bicarbonate (5.0 g) was added, and the stirred solution was slowly acidified with 64 mL of acetic acid (1.12 mol). The resulting mixture was stored at -18 C. overnight and then allowed to warm up to 0 C. The precipitated product was washed three times with 300 mL of water and dried under vacuum. The yield was 84 g (43%). NMR showed that the product had a structure consistent with 4-(tetrahydro-2H-pyran-2-yloxy) phenol. |
pyridinium p-toluenesulfonate; In diethyl ether; dichloromethane; | [Reference Example 3 (synthesis of acrylic compound 3)]; In accordance with Scheme 3 below, an acrylic compound 3 was synthesized. [Show Image]; [Reference Example 4 (synthesis of acrylic compound 4)]; In accordance with Scheme 4 below, an acrylic compound 4 was synthesized. [Show Image]; [Example 1 (synthesis of dioxetane compound 1)]; [Show Image] In accordance with Scheme 8 above, a dioxetane compound 1 was synthesized using hydroquinone, 3,4-dihydro-2H-pyrane, the intermediate compound 1 having an oxetanyl group and the intermediate compound 2 having an oxetanyl group. The resulting compound was refined by recrystallization with a hexane/ethyl acetate solvent. The recrystallized product was white solid at room temperature. The 1H-NMR spectrum of the dioxetane compound 1 is shown in Fig. 1 and the result of the DSC measurement is shown in Fig. 2. It was confirmed from the result of DSC and polarizing microscope observation that the dioxetane compound 1 exhibited C-Iso phase behavior and no liquid crystallinity. (1) Peak positions of dioxetane compound 1 in 1H-NMR (CDCl3; TMS) delta 0.9(t, 3H), 1.0(t, 3H), 1.7(dd, 2H), 1.8(m, 2H), 1.9(m, 4H), 3.6(t, 4H), 4.1(t, 2H), 4.2(s, 2H), 4.4(d, 2H), 4.5(d, 2H), 4.5(d, 2H), 4.6(d, 2H), 7.0(dd, 4H), 7.3(s, 2H), 8.2(dd, 4H) (2) Peak positions of dioxetane compound 1 in 13C-NMR (CDCl3; TMS) delta 8.46, 26.30, 26.39, 26.89, 27.02, 43.37, 43.63, 68.24, 70.69, 71.26, 73.72, 78.20, 78.73, 114.52, 114.60, 121.68, 121.22, 122.84, 122.88, 132.52, 132.57, 148.57, 148.65, 163.56, 163.69, 164.92, 165.00 |
With pyridinium p-toluenesulfonate; In diethyl ether; dichloromethane; at 20℃; for 3h; | In accordance with Scheme 1 below, an acrylic compound having an oxetanyl group (acrylic compound 1) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd.). The 1H-NMR spectrum of the acrylic compound 1 is shown in Fig. 1. "x" in the figures indicates the peak of the impurities. | |
With poly(4-vinylpyridine) supported copper(II) oxide nanoparticles; In dichloromethane; at 20℃; for 0.0833333h; | General procedure: A mixture of the substrate (1 mmol), 3,4-dihydro-2H-pyran (1 mmol) and PC-NPs (12 mg) in CH2Cl2 (3 drops) was stirred at room temperature. The progress of the reaction was monitored by TLC (EtOAc: n-hexane; 1:1). After completion of the reaction, the mixture was filtered to separate the solid catalyst. Then, the solution was filtered through a silica gel pad and washed with CH2Cl2 (2 × 5 mL). Evaporation of the solvent gave the desired product in high yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; | [Reference Example 3 (synthesis of acrylic compound 3)]; In accordance with Scheme 3 below, an acrylic compound 3 was synthesized. [Show Image]; [Reference Example 4 (synthesis of acrylic compound 4)]; In accordance with Scheme 4 below, an acrylic compound 4 was synthesized. [Show Image] | |
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 100℃; for 4h; | In accordance with Scheme 6 below, an acrylic compound 6 having an oxetanyl group (acrylic compound 6) was synthesized. The 1H-NMR spectrum of the acrylic compound 6 is shown in Fig. 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In accordance with Scheme 2 below, an acrylic compound having an oxetanyl group (acrylic compound 2) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd). The 1H-NMR spectrum of the acrylic compound 2 is shown in Fig. 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In accordance with Scheme 1 below, an acrylic compound having an oxetanyl group (acrylic compound 1) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd.). The 1H-NMR spectrum of the acrylic compound 1 is shown in Fig. 1. "x" in the figures indicates the peak of the impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Examples of preferred hydroquinone derivatives include: ... ethyl-2,5-diydroxy-4,6-dimethylphenylacetate; 2-(2,5-dihydroxy-4-methylphenyl)-N-octylacetamide; 6-(2,5-dihydroxy-4-methoxyphenyl)hexanoic acid; 4-[(6-methoxytetrahydro-2H-pyran-2-yl)oxyphenol; 4-[(tetrahydro-2H-pyran-2-yl)oxy]phenol; and 4-[(tetrahydro-2H-thiopyran-2-yl)oxy]phenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.6 g (47%) | With tributylphosphine; In tetrahydrofuran; | (i) 4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile A cooled (0 C.) mixture of 4-(1-hydroxy-3-butenyl)benzonitrile (4.93 g, 28.5 mmol) and <strong>[53936-56-4]4-(tetrahydro-2H-pyran-2-yloxy)phenol</strong> (8.3 g, 42.7 mmol) in dry THF (200 mL) was treated with tributylphosphine (8.85 mL, 42.7 mmol), followed by 1,1'-(azodicarbonyl)dipiperidine (10.77 g, 42.7 mmol). After addition was complete, the reaction mixture was stirred at 0 C. for 10 min, before being stirred at rt overnight. The precipitate of tributylphosphine oxide was removed by filtration and the filtrate was concentrated in vacuo to give 24.6 g of crude product. This was purified by chromatography on silica gel, eluding with IPA:EtOAc heptane (5:5:90), to give 4.6 g (47%) of the sub-title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24 g (68.7%) | In toluene; | (i) 4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile 4-(Tetrahydro-2H-pyran-2-yloxy)phenol (19.0 g; 0.1 mol) and 4-(1-hydroxy-3-butenyl)benzonitrile (17.8 g; 0.1 mol) was mixed in toluene, and cooled to 0 C. (under nitrogen). TBP (22.9 g; 0.11 mol) was added, followed by ADDP. The mixture was stirred at rt overnight, filtered, and evaporated. Purification by chromatography on silica gave 24 g (68.7%) of the desired compound. |
24 g (68.7%) | In toluene; | (d) 4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl} benzonitrile 4-(Tetrahydro-2H-pyran-2-yloxy)phenol (19.0 g, 0.1 mol) and 4-(1-hydroxy-3-butenyl)benzonitrile (17.8 g, 0.1 mol) was mixed in toluene, and cooled to 0 C. (under nitrogen). TBP (22.9 g, 0.11 mol) was added, followed by ADDP. The mixture was stirred at rt overnight, filtered, and evaporated. Purification by chromatography on silica gave 24 g (68.7%) of the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; chloroform; | Reference Example 14 2-[4-(Tetrahydropyran-2-yloxy)phenoxy]-6-chloro-3-cyanoimidazo[1,2-a]pyridine To a suspension of 60% sodium hydride in oil (0.66g) in anhydrous dimethylformamide (10ml) was dropwise added a solution of <strong>[53936-56-4]p-(tetrahydropyran-2-yloxy)phenol</strong> (2.9g) in dimethylformamide (10ml) at room temperature. The mixture was stirred for 40 minutes at room temperature, to which 2,6-dichloro-3-cyanoimidazo[1,2-a]pyridine in crystalline form (2.1g) was added and stirred for 1.5 hours at 130 to 135C. The reaction mixture was concentrated under reduced pressure, and the residue was treated with chloroform to remove insoluble material. The chloroform layer was distilled to remove chloroform. The residue was purified by a silica gel column chromatography to obtain colorless crystals of the title compound (1.9g). m.p. 172 - 175C NMR(CDCl3)delta: 1.33-2.12(br,m,6H), 3.38-3.71(br,m,1H), 3.75-4.10(br.m,1H), 5.31-5.44(m,1H), 6.93-7.31(m,4H), 7.35-7.60(m,2H), 8.25(s,1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20℃; under 3000.3 Torr; for 3h;Autoclave; | To a 1-liter autoclave, 56.3 g (198 mmol) of the compound (9-2), 2.8 g of a catalyst (5% Pd/C), and 250 ml of ethanol were added. The resulting mixture was reacted at room temperature for 3 hours while the hydrogen pressure was maintained to be 0.4 MPa. After the catalyst had been removed by filtration, vacuum concentration was performed. Hereby, 38.5 g of the compound (9-3) was prepared (quantitative) |
82% | With aluminum oxide; hydrogen;palladium on activated charcoal; In ethyl acetate; at 20℃;Product distribution / selectivity; | According to this procedure several other bases were tested (see table). |
80% | With hydrogen; calcium carbonate;palladium on activated charcoal; In ethyl acetate; at 20℃;Product distribution / selectivity; | Example 2; Step 2; To a stirred solution of the product (30 g, 0.105 mol), calcium carbonate (2.79 g, 0.027 mol) and ethyl acetate (120 ml) was added palladium on carbon (3.6 g). The mixture was stirred at ambient temperature under hydrogen pressure until uptake of hydrogen ceased. The mixture was filtered and washed with ethyl acetate. The solvent was distilled off in vacuum. The evaporation residue was dissolved in alcohol (36 ml) and the product precipitated by the addition of water (144 ml). The slurry was cooled to 00C and stirred vigorously for 2 h. Precipitated product was filtered and washed with water, dried in vacuum to give 80% of Deoxyarbutin with a purity of 99.8% (area by HPLC). |
80% | With hydrogen; sodium carbonate;palladium on activated charcoal; In isopropyl alcohol; at 20℃;Product distribution / selectivity; | According to this procedure several other bases were tested (see table). |
80% | With hydrogen; calcium carbonate;palladium on activated charcoal; In ethanol; ethyl acetate; at 20℃;Product distribution / selectivity; | According to this procedure several other bases were tested (see table). |
78% | With hydrogen; calcium carbonate;palladium on activated charcoal; In ethanol; at 20℃;Product distribution / selectivity; | According to this procedure several other bases were tested (see table). |
77% | With hydrogen; calcium carbonate;palladium on activated charcoal; In isopropyl alcohol; at 20℃;Product distribution / selectivity; | According to this procedure several other bases were tested (see table). |
4.1 g | With pyridine; 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; ethanol; at 50℃; under 3750.38 Torr; for 8h; | In a pressure-resistant container, 6.7 g of the compound represented by the formula (I-1-4) 70 mL of tetrahydrofuran, 20 mL of ethanol, 10 mL of pyridine, 0.7 g of 5% palladium carbon (containing 60% of water) was added, 0.5 MPa, And the mixture was heated and stirred at 50 C. for 8 hours. The palladium was removed by filtration and the solvent was distilled off. Dissolve in ethyl acetate, add 1% hydrochloric acid, Washed sequentially with water and brine. Purification was carried out by column chromatography (alumina, ethyl acetate) 4.1 g of a compound represented by the formula (I-1-5) was obtained. |
8.8 g | With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; ethanol; at 50℃; under 3750.38 Torr; for 8h; | 13.5 g of a compound represented by Formula (I-11-11), 0.1 g of 5% palladium carbon, 50 mL of tetrahydrofuran, and 50 mL of ethanol were added to a pressure-resistant container. The mixture was heated and stirred at 50 C. for 8 hours under a hydrogen pressure of 0.5 MPa. After filtration of the catalyst, the solvent was distilled off to obtain 8.8 g of a compound represented by Formula (I-11-12). |
8.8 g | With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; ethanol; at 50℃; under 3750.38 Torr; for 8h; | 13.5 g of the compound represented by the formula (I-9-11), 0.1 g of 5% palladium carbon, 50 mL of tetrahydrofuran, and 50 mL of ethanol were placed in a pressure-resistant container.The mixture was heated and stirred at a hydrogen pressure of 0.5 MPa at 50 C for 8 hours.After filtering the catalyst, the solvent was distilled off, whereby 8.8 g of the compound represented by the formula (I-9-12) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-carbodiimide;dmap; In dichloromethane; | [Example 1 (synthesis of dioxetane compound 1)]; [Show Image] In accordance with Scheme 8 above, a dioxetane compound 1 was synthesized using hydroquinone, 3,4-dihydro-2H-pyrane, the intermediate compound 1 having an oxetanyl group and the intermediate compound 2 having an oxetanyl group. The resulting compound was refined by recrystallization with a hexane/ethyl acetate solvent. The recrystallized product was white solid at room temperature. The 1H-NMR spectrum of the dioxetane compound 1 is shown in Fig. 1 and the result of the DSC measurement is shown in Fig. 2. It was confirmed from the result of DSC and polarizing microscope observation that the dioxetane compound 1 exhibited C-Iso phase behavior and no liquid crystallinity. (1) Peak positions of dioxetane compound 1 in 1H-NMR (CDCl3; TMS) delta 0.9(t, 3H), 1.0(t, 3H), 1.7(dd, 2H), 1.8(m, 2H), 1.9(m, 4H), 3.6(t, 4H), 4.1(t, 2H), 4.2(s, 2H), 4.4(d, 2H), 4.5(d, 2H), 4.5(d, 2H), 4.6(d, 2H), 7.0(dd, 4H), 7.3(s, 2H), 8.2(dd, 4H) (2) Peak positions of dioxetane compound 1 in 13C-NMR (CDCl3; TMS) delta 8.46, 26.30, 26.39, 26.89, 27.02, 43.37, 43.63, 68.24, 70.69, 71.26, 73.72, 78.20, 78.73, 114.52, 114.60, 121.68, 121.22, 122.84, 122.88, 132.52, 132.57, 148.57, 148.65, 163.56, 163.69, 164.92, 165.00 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a mixture of 2-(2-chloroethoxy)ethyl p-toluenesulfonate (14) (2.04 g, 7.34 mmol) and <strong>[53936-56-4]p-(tetrahydropyran-2-yloxy)phenol</strong> (13) (950 mg, 4.89 mmol), DMF (25.0 mL) was added K2CO3 (1.35 g, 9.78 mmol) at room temperature under argon. After the reaction mixture was stirred at 70 C for 30 h, sodium azide (1.30 g, 19.6 mmol) and tetra-n-butylammonium iodide (1.80 g, 4.89 mmol) were added to the reaction mixture at the same temperature. After being stirred at same temperature for 30 h, the reaction mixture was poured into ice-cooled 3 M HCl. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layer was washed with saturated aq NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was used for the next reaction without further purification. To a stirred solution of the above residue in methanol (10.0 mL) and THF (5.00 mL) was added a catalytic amount of 10-camphorsufonic acid at room temperature under argon. After being stirred at same temperature for 5 min, the reaction mixture was concentrated in vacuo. The residue purified by chromatography on silica gel with 75:25 ethyl acetate-hexane to give 4-[2-(2-azidoethoxy)ethoxy]phenol (16) (981 mg, 4.39 mmol, 90% in three steps). 1H NMR (270 MHz, CDCl3): delta 6.73-6.85 (m, 4H), 4.10 (t, 2H, J=4.9 Hz), 3.84 (t, 2H, J=4.9 Hz), 3.74 (t, 2H, J=5.3 Hz), 3.41 (t, 2H, J=5.3 Hz); 13C NMR (100 MHz, CDCl3) delta 152.2, 149.9, 115.9, 115.7, 69.9, 69.6, 68.0, 50.4; IR (neat): 3377, 2929, 2106, 1603, 1509, 1452, 1346, 1233, 1129, 1063, 927, 829, 755, 643, 521 cm-1; HRMS (ESI-TOF) calcd for C10H13O3 [M+H]+m/z=224.1035, found: 224.1037. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium carbonate; In ISOPROPYLAMIDE; at 90 - 100℃;Inert atmosphere; | Example 4; [Show Image] [Show Image] According to the method described in JP 2004-262884 A, the compound represented by formula (A-I) was produced by reacting dihydroquinone with dihydropyran in the presence of an acid catalyst. One hundred point one (100.1) grams of the compound represented by formula (A-I) was mixed with 97.1 g of potassium carbonate, 64 g of 6-chlorohexanol and N,N-dimethylacetamide, and the mixture obtained was stirred at 90C under an atmosphere of nitrogen, and further stirred at 100C. The solution obtained was cooled down to room temperature, and then, pure water and methyl isobutyl ketone were added thereto. The organic layer was separated from the mixture obtained, and then, the organic layer was washed with an aqueous sodium hydroxide solution and pure water. The organic layer was filtrated, and then, concentrated under reduced pressure. To the residue obtained, methanol was added, and the precipitate generated was isolated by filtration. The precipitate isolated was dried in a vacuum to obtain 126 g of a compound represented by formula (A-II). Yield: 91% (based on 6-chlorohexanol). |
91% | With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 100℃;Inert atmosphere; | Compound (a) of the 100 g, 97 g of potassium carbonate and 64 g of 6-chloro-hexanol, N, N- dimethylacetamide, a nitrogen atmosphere, and reacted by heating at 90C. In addition, the reaction was heated to 100C. Cooling the reaction mixture to room temperature and was added to pure water and methyl isobutyl ketone, and the organic layer was separated. The organic layer was washed with aqueous solution of sodium hydroxide and pure water, and dehydrated. Remove the dehydrating agent by filtration, the resulting filtrate was concentrated under reduced pressure. Methanol was added to the resulting residue, to remove the resulting precipitate by filtration and vacuum drying, the compound (b) to obtain a 126 g. Yield: 91% (based on 6-chloro-hexanol). |
84.9% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 24h;Inert atmosphere; | In a nitrogen atmosphere, 38.5 g of the compound (9-3), 41.0 g (297 mmol) of potassium carbonate, 27.0 g (198 mmol) of 6-chloro-1-hexanol, and 300 ml of dimethylformamide were added to a 500-mi four-necked flask. The resulting liquid mixture was heated to 1000 C. and then reacted for 24 hours. Afier cooling had been performed, 600 ml of ethyl acetate and 600 ml of water were added to the mixture and liquid separation was performed. The resulting organic layer was cleaned with water and a saturated saline solution in this order. Then, drying with sodium sulfate was performed. After sodium sulfate had been removed by filtration, vacuum concentration was performed. While ice- cooling was performed, hexane was added to the concentrated residue and crystallization was performed. The resulting crystals were filtered and then vacuum-dried. Hereby, 49.5 g of the compound (9-4) was prepared (yield: 84.9%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide; In chloroform;Inert atmosphere; Cooling with ice; | Example 5; [Show Image] [Show Image] Sixteen point nine (16.9) grams of a compound represented by formula (A-I) was mixed with 0.85 g of dimethylaminopyridine, 15 g of 2-acryloyloxyethyl succinate, 80 mg of 3,5-di-tert-butyl-4-hydroxytoluene and 100 mL of chloroform. The solution obtained was cooled with ice under an atmosphere of nitrogen, and then, a solution obtained by dissolving 19.68 g of dicyclohexylcarbodiimide in 20 mL of chloroform was added dropwise thereto. After completion of addition, the mixture obtained was stirred. To the reaction mixture obtained, 200 mL of chloroform and 200 mL of heptane were added to filtrate precipitation. The filtrate was washed with 2N hydrochloric acid, and then, insoluble matter was removed by filtration. The filtrate was dried over anhydrous sodium sulfate. After removing sodium sulfate by filtration, the filtrate was concentrated. The residue obtained was dried in a vacuum to obtain 21 g of a compound represented by formula (B-1). Twenty one (21) grams of the compound represented by formula (B-1) was mixed with 1.16 g of pure water, 1.02 g of p-toluenesulfonic acid monohydrate, 100 mg of 3,5-di-tert-butyl-4-hydroxytoluene and 200 mL of tetrahydrofuran. Under an atmosphere of nitrogen, the mixture obtained was stirred at 30C. The reaction mixture was cooled down to room temperature, and then, 200 ml of toluene was added thereto. The mixture obtained was washed with pure water, and then, 200 mL of heptane was added thereto. The insoluble matter was removed by filtration, and then, the filtrate obtained was concentrated under reduced pressure. To the concentrated residue, chloroform was added, and the mixture obtained was filtrated through silica gel. The filtrate was concentrated under reduced pressure, and the residue obtained was dried in a vacuum to obtain 16 g of a compound represented by formula (B). Yield: 75% (based on the compound represented by formula (A-I)). Ten point zero five (10.05) grams of the compound represented by formula (B) was mixed with 0.40 g of dimethylaminopyridine, 7.5 g of a compound represented by formula (3-A-3), 20 mg of 3,5-di-tert-butyl-4-hydroxytoluene and 300 mL of chloroform. The mixture obtained was cooled with ice, and then, a solution obtained by dissolving 7.39 g of dicyclohexylcarbodiimide in 20 mL of chloroform was added dropwise thereto. After completion of addition, the mixture obtained was stirred at room temperature for 3 hours to effect reaction. To the reaction solution, 200 mL of chloroform and 200 mL of heptane were added, and precipitation was removed by filtration. The filtrate obtained was washed with hydrochloric acid, and then, insoluble matter was removed by filtration. The filtrate was dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated. The residue obtained was dried in a vacuum to obtain 14.2 g of a compound represented by formula (6-B). Fourteen point two (14.2) grams of the compound represented by formula (6-B) was mixed with 0.59 g of pure water, 0.62 g of p-toluenesulfonic acid monohydrate, 40 mg of 3,5-di-tert-butyl-4-hydroxytoluene and 80 mL of tetrahydrofuran. Under an atmosphere of nitrogen, the mixture obtained was stirred at 50C for 3 hours to effect reaction. The reaction mixture was cooled down to room temperature, and then, concentrated to remove tetrahydrofuran. To the residue, 200 mL of heptane was added. The precipitation precipitated was isolated by filtration, and washed with pure water, and then, dried in a vacuum. The powder obtained was mixed with chloroform, and the mixture obtained was filtrated through silica gel. The filtrate was dissolved in 400 mL of chloroform, and the solution obtained was concentrated. To the concentrated residue, toluene was added to concentrate under reduced pressure. To the residue, 500 mL of heptane was added to conduct crystallization. The powder obtained was isolated by filtration, and dried in vacuum to obtain 10.1 g of a compound represented by formula (7-B). Yield: 67% (based on the compound represented by formula (B)). According to the result of high performance liquid chromatography analysis, impurities were not detected. |
Yield | Reaction Conditions | Operation in experiment |
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94% | With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide; In chloroform; at 20℃;Inert atmosphere; Cooling with ice; | Example 6; [Show Image] [Show Image] Ten point zero (10.0) grams of a compound represented by formula (A-I) was mixed with 5.14 g of dimethylaminopyridine, 10.5 g of 6-(2-acryloyloxyethoxy) caproate, 0.1 g of 3,5-di-tert-butyl-4-hydroxytoluene and 100 mL of chloroform. The solution obtained was cooled with ice under an atmosphere of nitrogen, and then, a solution obtained by dissolving 10.72 g of dicyclohexylcarbodiimide in 50 mL of chloroform was added dropwise thereto. After completion of addition, the mixture obtained was stirred at room temperature for 2 hours to effect reaction. The reaction mixture obtained was filtrated. To the filtrate obtained, 45 g of silica gel was added, and then, the mixture obtained was stirred at room temperature for 1 hour. The mixture was filtrated, and the filtrate obtained was concentrated under reduced pressure with a evaporator. The concentrated residue was mixed with tetrahydrofuran, and the mixture obtained was filtrated to remove insoluble matter. The filtrate obtained was concentrated under reduced pressure to obtain 17.55 g of a compound represented by formula (C-1) as a viscous liquid. Yield: 94% (based on the compound represented by formula (A-I)). Fourteen point zero (14.0) grams of the compound represented by formula (C-1) was mixed with 0.70 g of pure water, 0.367 g of p-toluenesulfonic acid monohydrate, 0.1 g of 3,5-di-tert-butyl-4-hydroxytoluene and 100 mL of tetrahydrofuran. Under an atmosphere of nitrogen, the mixture obtained was stirred at 30C, and then, further stirred at 60C for 30 minutes. The reaction mixture was concentrated under reduced pressure below 30C until the amount thereof became a third. The concentrated solution was mixed with 800 g of ice, and the white powder precipitated was isolated by filtration. The powder isolated was washed twice with 200 mL of pure water, and then, dried in a vacuum to obtain 9.11 g of white powder of a compound represented by formula (C). Yield: 85% (based on the compound represented by formula (C-I)). Eight point zero zero (8.00) grams of the compound represented by formula (C) was mixed with 0.245 g of dimethylaminopyridine, 6.62 g of a compound represented by formula (3-A-3), 0.1 g of 3,5-di-tert-butyl-4-hydroxytoluene and 80 mL of chloroform. Under an atmosphere of nitrogen, a solution obtained by dissolving 6.05 g of dicyclohexylcarbodiimide in 30 mL of chloroform was added dropwise to the mixture obtained under ice-cooling. After completion of addition, the mixture obtained was stirred at room temperature for 3 hours to effect reaction. The reaction mixture was filtrated. To the filtrate, 10 g of silica gel was added, and then, the mixture obtained was stirred at room temperature for 1 hour. The mixture was filtrated, and the filtrate obtained was concentrated under reduced pressure. The concentrated residue was mixed with 60 mL of tetrahydrofuran, and the mixture obtained was filtrated to remove insoluble matter. The filtrate obtained was concentrated under reduced pressure. The residue obtained was dried in a vacuum to obtain 13.56 g of a compound represented by formula (6-C) as a viscous liquid. Yield: 96% (based on the compound represented by formula (C)). Thirteen point five six (13.56) grams of the compound represented by formula (6-C) was mixed with 0.512 g of pure water, 0.631 g of p-toluenesulfonic acid monohydrate and 0.1 g of 3,5-di-tert-butyl-4-hydroxytoluene. Under an atmosphere of nitrogen, the mixture obtained was stirred at 50C for 2 hours to effect reaction. The reaction mixture was concentrated below 30C under reduced pressure. To the concentrated residue, 400 g of ice was added. The white crystal precipitated was isolated by filtration. The crystal isolated was washed twice with 300 mL of pure water, and then, further washed three times with a mixed solution of 100 mL of pure water and 50 mL of methanol. The crystal was dried in a vacuum to obtain 9.98 g of a compound represented by formula (7-C). Yield: 84% (based on the compound represented by formula (C)). |
Yield | Reaction Conditions | Operation in experiment |
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And synthesized naphthalene derivative in Preparation 1 (S-1) and hydroquinone monomethyl tetrahydropyranyl ether after the esterification reaction using a dehydrating condensing agent such as dicyclohexylcarbodiimide, and desorbed tetrahydropyranyl group using hydrochloric acid naphthalene derivatives get the (S-16). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.6% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25℃; for 16h;Inert atmosphere; Cooling with ice; | Under a nitrogen atmosphere, the compound (T-8) (23.2g, 119.7mmol), methacrylic acid (10.8g, 125.6mmol), and N, N-dimethyl-4-aminopyridine (DMAP) ( 0.4 g, 3.6 mmol) was dissolved in dichloromethane (300ml). To this solution, under ice-cooling with dicyclohexylcarbodiimide (DCC) (29.6g, 143.6mmol) to was added as a solid and stirred for 16 hours at 25 C.. After completion of the reaction, the resulting insoluble was filtered, the filtrate was extracted with dichloromethane, the combined organic layer was washed successively with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (toluene) to give compound (T-9) (26.2g, 100.0mmol, 83.6%). |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate; In N,N-dimethyl-formamide;Heating; | A compound represented by Formula (1-1-7), a compound represented by Formula (1-1-8), potassium carbonate, andN, N-dimethylformamide were put into a reaction container, followedby heating and stirring. The resultant product was diluted with dichloromethane, and then washed with water and brine. Purification was performed by column chromatography (alumina) to obtain a compound represented by Formula (1-1-9). | |
18.9 g | With caesium carbonate; In dimethyl sulfoxide; at 70℃; for 8h; | To a reaction container, 15.0 g of the compound represented by Formula (I-108-1), 13.8 g of the compound represented by Formula (I-108-2), 37.7 g of cesium carbonate, and 100 mL of dimethyl sulfoxide were added. The resulting mixture was stirred for 8 hours while being heated at 70 C. After the mixture had been cooled and then diluted with dichloromethane, washing was performed with water and subsequently with a saline solution. Then, purification was performed by column chromatography (alumina, dichloromethane). Hereby, 18.9 g of the compound represented by Formula (I-108-3) was prepared. (0164) To a reaction container, 18.9 g of the compound represented by Formula (I-108-3), 80 mL of tetrahydrofuran, 80 mL of methanol, and 1 mL of concentrated hydrochloric acid were added. The resulting mixture was stirred at room temperature for eight hours. After the solvent had been distilled away, dilution was performed with ethyl acetate. Subsequently, washing was performed with water and then with a saline solution. Then, purification was performed by column chromatography (alumina, ethyl acetate). Hereby, 11.0 g of the compound represented by Formula (I-108-4) was prepared. (0165) In a nitrogen atmosphere, 5.0 g of the compound represented by Formula (I-108-5), 5.3 g of the compound represented by Formula (I-108-4), 0.7 g of N,N-dimethylaminopyridine, and 200 mL of dichloromethane were added. While the resulting mixture was cooled with ice, 3.8 g of diisopropylcarbodiimide was added dropwise to the mixture, which was then stirred at room temperature for 10 hours. After the precipitate had been filtered away, the filtrate was washed with 1%-hydrochloric acid, with water, and then with a saline solution. After recrystallization (dichloromethane/methanol) had been performed, purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane/methanol). Hereby, 6.9 g of the compound represented by Formula (I-108-6) was prepared. (0166) In a nitrogen atmosphere, 100 mL of hydrazine monohydrate and 100 mL of ethanol were added to a reaction container. While the resulting mixture was heated at 50 C., 10.0 g of the compound represented by Formula (I-108-7) was added dropwise to the mixture, which was then stirred for 3 hours while being heated. Subsequently, dilution with dichloromethane and washing with a saline solution were performed. After drying had been performed with sodium sulfate, the solvent was distilled away. Hereby, 8.6 g of the compound represented by Formula (I-108-8) was prepared. (0167) In a nitrogen atmosphere, 10.8 g of the compound represented by Formula (I-108-9), 100 mL of 1,2-dimethoxyethane, and 7.7 g of triethylamine were added to a reaction container. While the resulting mixture was heated at 60 C., 8.6 g of the compound represented by Formula (I-108-8) was added dropwise to the mixture, which was then stirred for 2 hours while being heated. The reaction liquid was poured into water to precipitate a solid, which was then filtered. After the solid had been washed with water and then with hexane, it was dried. Hereby, 8.5 g of the compound represented by Formula (I-108-10) was prepared. (0168) To a reaction container, 1.4 g of the compound represented by Formula (I-108-10), 5.0 g of the compound represented by Formula (I-108-6), 0.6 g of (±)-10-camphorsulfonic acid, 20 mL of tetrahydrofuran, and 20 mL of ethanol were added. The resulting mixture was stirred for 8 hours while being heated at 50 C. After the solvent had been distilled away, purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane/methanol). Hereby, 5.0 g of the compound represented by Formula (I-108-11) was prepared. (0169) In a nitrogen atmosphere, 5.0 g of the compound represented by Formula (I-108-11), 0.8 g of diisopropylethylamine, and 80 mL of dichloromethane were added to a reaction container. While the resulting mixture was cooled with ice, 0.5 g of acryloyl chloride was added dropwise to the mixture, which was then stirred at room temperature for 12 hours. Subsequently, washing was performed with 1%-hydrochloric acid and then with a saline solution. After reprecipitation (methanol) had been performed, purification was performed by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane/methanol). Hereby, 3.2 g of the compound represented by Formula (I-108) was prepared. (0170) LCMS: 1086 [M+1] |
18.9 g | With caesium carbonate; In dimethyl sulfoxide; at 70℃; for 8h; | 15.0 g of the compound represented by the formula (I-4-1), 13.8 g of the compound represented by the formula (I-4-2), 37.7 g of cesium carbonate and 100 mL of dimethyl sulfoxide were put into a reactor, and heated with stirring at 70 C. for 8 hours. After cooled, this was diluted with dichloromethane, and then washed sequentially with water and salt water. Purification through column chromatography (alumina, dichloromethane) gave 18.9 g of the compound represented by the formula (I-4-3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide;Heating; | The compound represented by Formula (1-121-1) , a compoundrepresented by Formula (1-121-2) , potassiurr carbonate, and N, Ndimethvlformamide were put into a reaction container, followed by heatinq and stirrinq. The resultant product was diluted with dichIoromethane, and then washed with water and brine. Purification was performed by column chromatography (alumina) to obtain a compound represented by Formula (1-121-3).The compound represented by Formula (1-121-3), | |
166.5 g | With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 10h; | 115.9 g of a compound represented by the formula (I-118-1), 120.7 g of a compound represented by the formula (I-118-2), 272.2 g of cesium carbonate, and 580 mL of N,N-dimethylformamide were put in a reactor, and stirred at 60 C. for 10 hours. The reaction liquid was diluted with dichloromethane, and washed sequentially with water and salt solution. This was purified through column chromatography (alumina) to give 166.5 g of a compound represented by the formula (I-118-3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide;Heating; | The compound represented by Formula (1-7-5), a compound represented by Formula (1-7-6), potassium carbonate, andN, N-dimethylformamide were put into a reaction container, followedby heating and stirring. The resultant product was diluted with dichloromethane, and then washed with water and brine. Purification was performed by column chromatography (alumina) to obtain a compound represented byFormula (1-7-7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
410 g | To a reaction flask containing a suspension of the product of Step 1 (242.4 g, 1285.4 mmol), trans,trans-4-pentyl-[1,1?-bi(cyclohexane)]-4-carboxylic acid (360.4 g, 1248 mmol), and N,N-dimethylamino pyridine (15.2 g, 124.8 mmol) in 2.5 L of dichloromethane was added N,N?-dicyclohexylcarbodiimide (282.8 g, 1372.8 mmol) while stirring under nitrogen. The reaction was followed by HPLC, which indicated the reaction was complete within 2-3 hours. The reaction was stirred overnight then diluted with additional dichloromethane (1 L), whereafter the byproduct N,N?-dicyclohexylurea was removed by filtration. The filtrate was passed through a short pad of silica gel using dichloromethane as eluent. The resultant solution was washed 3 times with 300 mL 10% HCl then dried over anhydrous MgSO4. After subsequent filtration, removal of the solvent of the filtrate gave a light brown solid that was used directly for the next step without further purification; To a reaction flask containing a suspension of the product from Step 2 in 700 mL of THF and 100 mL of ethanol was added 10 mL of concentrated (36%) HCl drop-wise. The reaction mixture was gently stirred in a 35 C. water bath for 10 minutes. The resultant solution was quickly added to an excess of ice-cold water. The precipitate was collected by filtration and rinsed with deionized water. The crude product was crystallized from THF/ethanol (1:1, v/v). The solid thus obtained was dried under vacuum for 3 h at 60 C. to yield 410 g of a white crystalline powder. NMR showed that the product had a structure consistent with 4-hydroxyphenyl trans, trans-4?-pentyl-[1,1?-bi(cyclohexane)]-4-carboxylate. |
Tags: 53936-56-4 synthesis path| 53936-56-4 SDS| 53936-56-4 COA| 53936-56-4 purity| 53936-56-4 application| 53936-56-4 NMR| 53936-56-4 COA| 53936-56-4 structure
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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 |
Sorry,this product has been discontinued.
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