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CAS No. : | 20010-99-5 | MDL No. : | MFCD00673149 |
Formula : | C5H7N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HQIBSDCOMQYSPF-UHFFFAOYSA-N |
M.W : | 109.13 | Pubchem ID : | 266781 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 29.71 |
TPSA : | 51.8 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.89 cm/s |
Log Po/w (iLOGP) : | 0.85 |
Log Po/w (XLOGP3) : | -1.3 |
Log Po/w (WLOGP) : | -0.22 |
Log Po/w (MLOGP) : | -1.39 |
Log Po/w (SILICOS-IT) : | 0.55 |
Consensus Log Po/w : | -0.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.19 |
Solubility : | 71.0 mg/ml ; 0.651 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.71 |
Solubility : | 560.0 mg/ml ; 5.13 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.63 |
Solubility : | 2.53 mg/ml ; 0.0232 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P264-P270-P301+P310-P321-P330-P405-P501 | UN#: | 2810 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
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 |
---|---|---|
100% | With Ni-doped silica; hydrogen In toluene at 140℃; for 4 h; Autoclave; Inert atmosphere | The synthesis of 2-aminomethyl pyradine(2-AMPZ) was carried out by a method shown below, byreference to the method described in literature (JP A 2001-894594). 2-cyanopyradine used was from Sigma-Aldrich Co.LLC.1.05 g of 2-cyanopyradine (10 mmol) and 100mg of60 wt percent-Ni/5i02 were placed in an autoclave (5U53 16) with20 mL of toluene and replaced with argon gas. This waspressurized with hydrogen gas to 50 atm, stirred at 140°C. for4 hours. The reaction solution was filtered and concentratedto give 2-aminomethyl pyradine (2-AMPZ) quantitatively.10152] ‘H-NMR spectrum (399.78 MHz, CDC13):ö8.60-8.45 (m, 3H), 4.07 (s, 2H), 1.79 (br, 2H) |
98% | With hydrogen In 1,4-dioxane at 60℃; for 8 h; Autoclave | Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane under stirring, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was hydrogenated for 8 hours under 40 atmosphere at 60 °C, filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methylamine 1h (10.7 g, yield 98percent) as a brown oil. MS m/z (ESI): 110 [M+1] |
98% | With hydrogen In 1,4-dioxane at 60℃; for 8 h; Autoclave | Step 6 C-Pyrazin-2-yl-methylamine Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was reacted in hydrogen atmosphere for 8 hours under 40 atmosphere at 60 °C and filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methyl amine 1h (10.7 g, yield 98percent) as a brown oil. MS m/z (ESI): 110 [M+1]. |
98% | With hydrogen In 1,4-dioxane at 60℃; for 8 h; | Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was reacted in hydrogen atmosphere for 8 hours under 40 atmosphere at 60° C. and filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methyl amine 1h (10.7 g, yield 98percent) as a brown oil. MS m/z (ESI): 110 [M+1]. |
98% | With pyridine; hydrogen In 1,4-dioxane at 60℃; for 8 h; Autoclave | 2-cyano-pyrazol 1g (10.5 g, 100 mmol) was dissolved in 150 mL 1,4- dioxane was added 1.0 g Raney nickel in 250 mL autoclave at 60 , 40 atm of hydrogen the reaction was stirred for 8 hours. Filtered, and the filtrate was concentrated under reduced pressure, to give C- pyridin-2-yl - methylamine 1h (10.7 g, brown oil). Yield: 98percent. |
98.9% | With hydrogen In 1,4-dioxane at 60℃; for 48 h; | Pyrazine-2-carbonitrile (19 g, 180 mmol) was dissolved in 1,4-dioxane (280 mL), and then Raney nickel (1.9 g) was added. The reaction mixture was reacted in hydrogen atmosphere at 60°C for 48 hours. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to obtain the title compound (1) (19 g, 98.9percent) as a brown oil. 1H MR (400 MHz, DMSO-d6): δ 871 (s, 1H), 8.54-8.53 (m, 2H), 8.48 (d, J = 2.4Hz, 1H), 3.86 (s, 2H), 1.97 (br, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | for 1 h; Reflux | B. A suspension of 2-(pyrazin-2-ylmethyl)isoindoline-1 ,3-dione (3.56 g, 14.9 mmol) in 5 N aqueous sodium hydroxide (180 mL) was heated at reflux for 1 h, allowed to cool to ambient temperature extracted with dichloromethane (4 x 50 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford pyrazin-2-ylmethanamine as a yellow oil in 67percent yield (1.09 g), which was used without further purification: 1H NMR (300 MHz, CDCI3) £8.55 (br s, 1 H), 8.49-8.47 (m, 1 H), 8.42 (d, J = 2.4 Hz, 1 H), 3.99 (s, 2H), 1.66 (s, 2H); MS (ES+) m/z 109.7 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃; for 18h; | Example 70; 4- (3-Phenvl-indole-1-sulfoni)-N-pyrazin-2-Imethvl-benzamide; Add 10ml dry DMF to a flask under N2 containing 4- (3-Phenyl-indole-l- sulfonyl)-benzoic acid (500mg, 1. 33mmol, 1. Oeq), 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (279mg, 1. 46mmol, 1.1 eq), Dimethyl-pyridin-4-yl- amine (16mg,. 132mmol,. 1 eq), and C-Pyrazin-2-yl-methylamine (217mg, 1. 99mmol, 1.5 eq). Stir for 18 hours at room temperature. Remove solvent on rotovap and purify by silca gel chromatography to give 4- (3-Phenyl-indole-l-sulfonyl)-N-pyrazin-2-ylmethyl- benzamide (127mg, 20% yield). Mass Spectrum (m/e): 468.95 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.0% | With triethylamine; In ethanol; at 20℃; for 18h; | General procedure: To 2,3-dichloro-1,4-naphthoquinone (0.341g, 1.50mmol) in 1.5mlof ethanol was added 2-methoxyethylamine (0.124g, 1.65mmol) and triethylamine (0.227g,2.25mmol) and the mixture stirred at r. t. for 18h. The red precipitate formedwas filtered under suction, washed with distilled water and dried to afford (4) as a dark red solid, 87.8%. |
With N-ethyl-N,N-diisopropylamine; In water; benzene; | REFERENCE EXAMPLE 4 <strong>[20010-99-5]2-(Aminomethyl)pyrazine</strong> (3.2 g) and diisopropylethylamine (5.8 ml) were added to a solution of 2,3-dichloro-1,4-dihydro-1,4-dioxonaphthalene (3.0 g) in benzene (90 ml) and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction solution and the resulting precipitate was removed by filtration and then the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution with chloroform) to give 2-chloro-1,4-dihydro-1,4-dioxo-3-[(2-pyrazinylmethyl)amino]naphthalene (0.23 g) as a light brown powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In isopropyl alcohol; at 20℃; for 2h; | To a solution of 2-aminomethyl-pyrazine (5.0 g, 45.87 mmol) in isopropanol (50 ml) was added di-tert-butyl-pyrocarbonate (12.0 g, 55.84 mmol); the mixture was stirred at ambient temperature for 2 h. Next, the solvent was evaporatedand the residue was dissolved in DCM (30 ml), and subjected to silica gel purification (chloroformlmethanol gradient 0-30% in 100 mm.). Fractions containing desired product were combined and evaporated. Residue was dried under vacuum to provide Compound AA in quantitative yield(10.22 g, 99% purity) as amorphous solid. LC-MS: (mlz) observed (M+H) 210.5 (C10H15N302+H calc: 210.3) |
In dichloromethane; | Example 8. Synthesis of the primary amine, pyrazin-2-ylmethanaminechromatography 17 3. TFA / CH2CI2 18[0096] Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-fert-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate:methanol) provided 0.5O g of pure tert-butyl pyrazin-2-ylmethylcarbamate. Pure pyrazin-2- ylmethanamine (18) was obtained as the TFA salt from deprotection of the carbamate with 1:1 TFA / CH2Cl2. EPO <DP n="33"/>[0097] | |
In dichloromethane; | Example 8 Synthesis of the primary amine, pyrazin-2-ylmethanamine Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-tert-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate:methanol) provided 0.50 g of pure tert-butyl pyrazin-2-ylmethylcarbamate. |
In dichloromethane; | Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-terf-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate methanol) provided 0.50 g of pure tert-butyl pyrazin-2-ylmethylcarbamate. Pure pyrazin-2-yhnethanamine (18) was obtained as the TFA salt from deprotection of the carbamate with 1:1 TFA / CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7 6-methyl-N-(2-pyrazinylmethyl)ergoline-8beta-carboxamide In an analogous manner to that described in Example 1, 6-methyl-N-(2-pyrazinylmethyl)ergoline-8beta-carboxamide is prepared from aminomethylpyrazine (obtained according to J. Org. Chemistry 38, 2049 (1973)) as a starting compound. After pouring onto a 2N-soda solution and extracting with methylene chloride and evaporating the solvent, the crude product is purified by chromatography on a column of silica gel using methylene chloride/methanol/concentrated ammonia (93:7:0.7) as the eluant. The pure product is crystallized from ethanol/n-hexane. Decomposition without melting above 194. [alpha]D20 =-93.0 (c=1,0 in dimethylformamide). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | EXAMPLE 10 Preparation of 1-Amino-3-(pyrazinylmethyl)guanidine hydriodide A solution of 3.66 g. of methyl thiocarbazimidate hydriodide and 3.42 g. of (aminomethyl)pyrazine [A. Hirschberg and P. Mattner, J. Med. Chem., 11, 911 (1961)] in 50 ml. of absolute ethanol is heated at reflux for 20 hours and then concentrated to dryness under reduced pressure to give the desired product as an orange solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; | Preparation 103 To a solution of <strong>[20010-99-5]2-aminomethylpyrazine</strong> (2.18g) and triethylamine (4.05g) in tetrahydrofuran (50ml) was added 2-chloro-5-nitropyridine (3.17g). The mixture was stirred at 60C for 6 hours, poured into ice-water and stirred for 10 minutes. The precipitate was collected by filtration, washed with water and dried to give 5-nitro-N-(2-pyrazinylmethyl)-2-pyridylamine (4.06g). APCI-mass;m/z232.20(M+H+) 1H-NMR(DMSO-d6): delta;4.78(2H,d,J=5.9Hz), 6.72(1H,d,J=9.4Hz), 8.16(1H,dd, J=2.8Hz,9.4Hz), 8.5-8.9(4H,m), 8.89(1H,d,J=2.8Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 0 - 20℃; for 3h;Cooling with ice; | C-Pyrazin-2-yl-methylamine 1h (10.9 g, 100 mmol) was added into a reaction flask, then 20 mL of trifluoroacetic anhydride was added dropwise slowly within an hour at 0 C in an ice-water bath. The reaction mixture was reacted at room temperature for 2 hours and monitored by thin layer chromatography until the disappearance of the starting materials. Then it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 2,2,2-trifluoro-N-pyrazin-2-ylmethyl-acetamide 1i (21.0 g) as a brown oil. MS m/z (ESI): 206.1 [M+1] | |
at 0 - 20℃; for 3h; | Step 7 2,2,2-Trifluoro-N-pyrazin-2-ylmethyl-acetamide C-Pyrazin-2-yl-methylamine 1h (10.9 g, 100 mmol) was added into a reaction flask, then 20 mL of trifluoroacetic anhydride was added dropwise slowly within an hour at 0C in an ice-water bath. The reaction mixture was reacted at room temperature for 2 hours. Then the mixture was concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography with system A as eluant to obtain the title compound 2,2,2-trifluoro-N-pyrazin-2-ylmethyl-acetamide 1i (21.0 g) as a brown oil. MS m/z (ESI): 206.1 [M+1]. | |
at 0 - 20℃; for 3h; | C-Pyrazin-2-yl-methylamine 1 h (10.9 g, 100 mmol) was added into a reaction flask, then 20 mL of trifluoroacetic anhydride was added dropwise slowly within an hour at 0 C. in an ice-water bath. The reaction mixture was reacted at room temperature for 2 hours. Then the mixture was concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography with system A as eluant to obtain the title compound 2,2,2-trifluoro-N-pyrazin-2-ylmethyl-acetamide 1i (21.0 g) as a brown oil. MS m/z (ESI): 206.1 [M+1]. |
21.0 g | at 20℃; for 3h;Cooling with ice; | The C- pyridin-2-yl - methylamine 1h (10.9 g, 100 mmol) was added to the reaction flask under ice bath, was added dropwise over 1 hour 20 mL of trifluoroacetic anhydride, the reaction was stirred at room temperature for 2 hours, The reaction solution was concentrated under reduced pressure, column chromatography using silica gel eluting with system A was obtained residue was purified to give the title product 2,2,2-trifluoro-2-methyl -N- pyridin - formamide 1i ( 21.0 g, brown oil). |
at 0 - 20℃; for 12h; | In the 0 C lower, will be C - pyrazine -2 - yl - amine (5 g, 45.9 mmol) is added to the reaction flask, slowly dropping 9.8 ml trifluoroacetic anhydride, stir at room temperature 12 hours, the reaction solution is concentrated under reduced pressure, to obtain the title product trifluoro acetyl pyrazine -2 - methylamine (15 g crude, brown oily matter), directly used for the next step reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 48: 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1 -(2-pyrazinylmethyl)-1 ,3- dihydro-2H-imidazo[4,5-c]quinolin-2-one; In a 100ml flask a mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3- quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg,) and (2- pyrazinylmethyl)amine (2.5 eq) in acetonitrile was heated at 100C for 2h. The reaction mixture was hydrolyzed with a solution of sodium hydrogen carbonate, extracted with DCM and the organic dried over Na2S04, filtered and concentrated to dryness to give the crude intermediate. The residue was dissolved in acetonitrile (15ml), bis(trifluoroacetoxy)iodo]benzene (0.5g) was added and the reaction mixture was stirred for 3h at room temperature. The reaction mixture was washed with water, extracted with DCM and the organic were dried over Na2S04, filtered and concentrated to dryness. The resulting crude compound was purified by chromatography on silica gel eluting with DCM / methanol (95:5) and the resulting residue was recrystallised from acetonitrile and dried in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1 -(2-pyrimidinylmethyl)-1 ,3- dihydro-2H-imidazo[4,5-c]quinolin-2-one (100mg) as a beige powder.LC-HRMS: ES+ exact mass calculated for C2i H19N603 403.1519 MH+, found: 403.1550, Rt 2.06min. | ||
In acetonitrile; at 100℃; for 2h; | In a 100 ml flask a mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg,) and (2-pyrazinylmethyl)amine (2.5 eq) in acetonitrile was heated at 100 C. for 2 h. The reaction mixture was hydrolyzed with a solution of sodium hydrogen carbonate, extracted with DCM and the organic dried over Na2SO4, filtered and concentrated to dryness to give the crude intermediate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; isopropyl alcohol; | Synthesis of pyrazin-2-ylmethyl-carbamic acid tert-butyl ester (Compound AA) To a solution of 2-aminomethyl-pyrazine (5.0 g, 45.87 mmol) in isopropanol (50 ml) was added di-tert-butyl-pyrocarbonate (12.0 g, 55.84 mmol); the mixture was stirred at ambient temperature for 2 h. Next, the solvent was evaporated and the residue was dissolved in DCM (30 ml), and subjected to silica gel purification (chloroform/methanol gradient 0->30% in 100 min.). Fractions containing desired product were combined and evaporated. Residue was dried under vacuum to provide Compound AA in quantitative yield (10.22 g, 99% purity) as amorphous solid. LC-MS: (m/z) observed (M+H+) 210.5 (C10H15N3O2+H calc: 210.3). | |
In isopropyl alcohol; | Synthesis of pyrazin-2-ylmethyl-carbamic acid tert-butyl ester (Compound AA) To a solution of 2-aminomethyl-pyrazine (5.0 g, 45.87 mmol) in isopropanol (50 ml) was added di-tert-butyl-pyrocarbonate (12.0 g, 55.84 mmol); the mixture was stirred at ambient temperature for 2 h. Next, the solvent was evaporated and the residue was dissolved in DCM (30 ml), and subjected to silica gel purification (chloroform/methanol gradient 0->30% in 100 min.). Fractions containing desired product were combined and evaporated. Residue was dried under vacuum to provide Compound AA in quantitative yield (10.22 g, 99% purity) as amorphous solid. LC-MS: (m/z) observed (M+H+) 210.5 (C10H15N3O2+H calc: 210.3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With water; sodium hydroxide; for 1h;Reflux; | B. A suspension of 2-(pyrazin-2-ylmethyl)isoindoline-1 ,3-dione (3.56 g, 14.9 mmol) in 5 N aqueous sodium hydroxide (180 mL) was heated at reflux for 1 h, allowed to cool to ambient temperature extracted with dichloromethane (4 x 50 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford pyrazin-2-ylmethanamine as a yellow oil in 67% yield (1.09 g), which was used without further purification: 1H NMR (300 MHz, CDCI3) £8.55 (br s, 1 H), 8.49-8.47 (m, 1 H), 8.42 (d, J = 2.4 Hz, 1 H), 3.99 (s, 2H), 1.66 (s, 2H); MS (ES+) m/z 109.7 (M + 1). |
With hydrazine hydrate; In ethanol; for 2h;Reflux; | 2-Pyrazinemethylphthalimide(0.15 g, 0.63 mmol) was suspended in ethanol (10 mL) andhydrazine hydrate (80% w/w%, 1.5 mL, 3.1 mmol) addedbefore the suspension was heated to reflux for two hours.The suspension was then cooled to room temperaturethen further cooled in the fridge. The suspension wasfiltered and the filtrate taken to dryness yielding 2-(aminomethyl)pyrazine as a yellow oil that was used without further purification (0.05 g, ca. 74%). Found: C, 52.70; H,6.60; N, 36.43. Calculated for C5H7N3O·H2O: C, 52.43; H,6.69; N, 36.69. 1H NMR (300 MHz, CDCl3): delta (ppm) 8.54 (d,J = 1.5 Hz, 1H, H-3), 8.46 (dd, J = 1.5, 2.7 Hz, 1H, H-2), 8.40(d, J1,2 = 2.7 Hz, 1H, H-1), 3.96 (s, 2H, CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.379 g | With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;Reflux; | C. To a suspension of 5-chlorosalicylic acid (0.96 g, 5.6 mmol) in dichloromethane (13 mL) was added thionyl chloride (2 mL, 28 mmol) and N,N- dimethylformamide (~3 drops). The reaction mixture was heated at reflux for 1 h, at which point a clear solution was obtained. The mixture was allowed to cool to ambient temperature and was concentrated in vacuo. The residue was dissolved in dichloromethane (10 mL), and pyrazin-2-ylmethanamine (0.80 g, 4.6 mmol), N,N- diisopropylethylamine (1.6 mL, 9.3 mmol), and 4-(W,W-dimethylamino)pyridine (0.056 m, 0.5 mmol) were added. The reaction mixture was stirred at ambient temperature for 16 h, diluted with dichloromethane (70 mL) and washed with 1 N hydrochloric acid (2 x 7 mL), water (2 x 7 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography eluting with a 10-60% gradient of ethyl acetate in hexanes to afford 5-chloro-2-hydroxy-A/-(pyrazin-2-ylmethyl)benzamide as a yellow solid in 31 % yield (0.379 g): 1H NMR (300 MHz, CDCI3) £ 12.10 (s, 1 H), 8.67 (s, 1 H), 8.57 (s, 2H), 7.57 (br s, 1H), 7.46 (d, J = 2.1 Hz, 1 H), 7.34 (dd, J = 8.9, 1.8 Hz, 1H), 6.93 (d, J = 8.9 Hz, 1 H), 4.78 (d, J = 4.8 Hz, 2H); MS (ES+) m/z 264.0 (M + 1 ), 266.0 (M + 1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.1% | With triethylamine; In toluene; at 50℃; for 3h; | To a suspension of (17) (0.809g, 2.4mmol) in 3mL of toluene, pyrazin-2-ylmethylamine(0.338g, 3.1mmol) then triethylamine (0.364g, 3.6mmol) was added drop-wise andstirred at 50C for 3h. The toluene was evaporated in vacuo. Reaction mixture was filtered under vacuum suction,washed with distilled water and EtOH and dried to afford (61) as an orange solid, 96.1%.1H (CDCl3) delta 8.80 (s, 1H),8.63 (s, 1H), 8.53 (s, 2H), 8.41 (d, 1H, J=2.56Hz),8.21 (s, 1H), 8.10 (d, 1H, J=7.62Hz),8.04 (d, 1H, J=7.60Hz), 7.76 (dt, 1H,J=1.29, 7.57Hz), 7.66 (dt, 1H, J=1.24, 7.54Hz), 2.00 (s, 4H)), 1.26 (s,3H); 13C (CDCl3) delta 155.58, 155.04, 143.97, 143.84,143.80, 143.74, 143.46, 142.88, 135.03, 132.64, 132.01, 126.61, 126.45, 124.83,107.41, 52.55, 29.58, 29.31. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.7% | With triethylamine; In toluene; at 50℃; for 3h; | To a suspension of (18) (0.483g, 1.50mmol) in 2mL of toluene, pyrazin-2-ylmethylamine(0.236g, 2.25mmol) then triethylamine (0.227g, 2.25mmol) was added drop-wiseand stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extractedwith EtOAc, washed with brine and dried over anhydrous Na2SO4.Purification by column (EtOAc/Hexane 1:1) afforded (51) as a red oil, 24.7%.1H (CDCl3) delta 8.64(d, 1H, J=1.11Hz), 8.59-8.61 (m, 1H),8.55 (d, 1H, J=2.51Hz), 8.14 (dd, 1H,J=0.71, 7.65Hz), 8.09 (d, 1H, J=7.63Hz), 7.77 (dt, 1H, J=1.27. 7.58Hz), 7.67 (dt, 1H, J=1.26, 7.56Hz), 7.59 (br s, 1H), 4.87-5.12(m, 2H), 3.74-3.79 (m, 2H), 3.48-3.53 (m, 2H), 3.27-3.39 (m, 2H), 1.97 (s, 3H),0.91 (t, 2H, J=7.00Hz); 13C(CDCl3) delta 192.42, 181.81, 178.90, 172.87, 148.51, 144.87, 143.77,143.55, 135.10, 135.06, 132.62, 132.56, 126.73, 126.64, 126.57, 126.36, 67.71,67.29, 66.19, 48.82, 22.23, 14.91. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.7% | With triethylamine; In toluene; at 50℃; for 3h; | To a suspensionof (19) (0.395, 1.50mmol) in 2mL oftoluene, pyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227g,2.25mmol) were added drop-wise and stirred at 50C for 3h. The toluene was thenremoved in vacuo. Reaction mixturewas filtered under vacuum suction, washed with distilled water and EtOH anddried to afford (52) as an orangesolid, 99.7%.1H (CDCl3) delta 8.65-8.57 (m,3H), 8.16 (dd, 1H, J=1.15,7.71Hz), 8.13 (dd, 1H, J=1.06, 7.70Hz),7.79 (dt, 1H, J=1.31, 7.57Hz),7.69 (dt, 1H, J=1.27, 7.55Hz),7.53 (br s, 1H), 4.76 (s, 2H), 3.17 (s, 3H), 1.96 (s, 3H); 13C (CDCl3)delta 182.05, 179.42, 172.59, 150.55, 144.07, 143.86, 143.80, 143.14, 135.33,132.78, 132.44, 130.23, 126.78, 45.81, 44.98, 21.82. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.9% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspensionof (19) (0.395, 1.50mmol) in 2mL oftoluene, pyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227g,2.25mmol) were added drop-wise and stirred at 50C for 3h. The toluene was thenremoved in vacuo. Reaction mixturewas filtered under vacuum suction, washed with distilled water and EtOH anddried to afford (52) as an orangesolid, 99.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.9% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspensionof (19) (0.395, 1.50mmol) in 2mL oftoluene, pyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227g,2.25mmol) were added drop-wise and stirred at 50C for 3h. The toluene was thenremoved in vacuo. Reaction mixturewas filtered under vacuum suction, washed with distilled water and EtOH anddried to afford (52) as an orangesolid, 99.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.0% | With triethylamine; In toluene; at 50℃; for 3h; | To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%.1H (CDCl3) delta 8.64 (s, 1H), 8.62 (d,1H, J=2.40Hz), 8.58 (d, 1H, J=2.30Hz), 8.17 (dd, 1H, J=0.80, 7.68Hz), 8.13 (dd, 1H, J=0.75, 7.77Hz), 7.80 (dt, 1H, J=1.26, 7.58Hz), 7.70 (dt, 1H, J=1.24, 7.55Hz), 7.49 (br s, 1H),4.90-4.72 (m, 2H), 4.65-4.55 (m, 1H), 1.96 (s, 3H), 1.33 (d, 3H, J=6.35Hz), 1.11 (d, 2H, J=6.93Hz); 13C (CDCl3)delta 171.97, 150.50, 144.07, 143.96, 143.75, 135.25, 132.70, 132.36, 130.40,126.84, 126.67, 77.20, 50.35, 45.15, 29.68, 23.33, 21.43, 19.94 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.9% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.5% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.2% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.0% | With triethylamine; In toluene; at 50℃; for 3h; | General procedure: To a suspension of (22) (0.437g, 1.50mmol) in 2ml of toluene was addedpyrazin-2-ylmethylamine (0.246g, 2.25mmol) and triethylamine (0.227mg,2.25mmol) and stirred at 50C for 3h. Toluene was removed in vacuo. Distilled water was added to the residue and extracted with CH2Cl2, washed with brine and driedover anhydrous Na2SO4. Purification by columnchromatography (3:1 EtOAc/Hexanes) afforded (55) as red solids, 65.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.2% | With triethylamine; In toluene; at 50℃; for 3h; | To a suspension of (72) (1.415g, 4.4mmol) in 5mL of toluene, pyrazin-2-ylmethylamine(0.576g, 5.3mmol) and triethylamine (0.667g, 6.6mmol) were added drop-wise andstirred at 50C for 3h. The toluene was removed in vacuo. 25mL of distilled water was added and then extracted withEtOAc. The organic layer was washed with brine and dried over Na2SO4.Purification by column (92:8 EtOAC/MeOH) afforded (73) as an orange oil, 32.2%.1H (CDCl3) delta 8.60(s, 1H), 8.59 (d, 1H, J=2.13Hz), 8.54 (d, 1H, J=2.18Hz), 8.12 (d, 1H, J=7.54Hz),8.08 (d, 1H, J=7.55Hz), 7.76 (dt, 1H, J=1.03, 7.48Hz), 7.66 (dt, 1H, J=0.96, 7.55Hz), 7.50 (br s, 1H), 5.10-4.73 (m, 2H), 3.95-3.43 (m,4H), 3.17 (s, 3H), 2.28-2.12 (m, 2H), 1.05 (t, 3H, J=7.39Hz); 13C(CDCl3) delta 175.92, 143.81, 135.04, 132.60, 132.38, 130.56, 126.63,126.55, 69.87, 58.44, 48.82, 27.26, 9.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 140℃; for 0.5h;Microwave irradiation; Inert atmosphere; | To(80) (0.419g, 1.5mmol) in 0.5ml ofCH3CN was added pyrazin-2-ylmethylamine (0.818g, 7.5mmol) and themixture irradiated by microwave at 140C for 30min under inert atmosphere. Thereaction mixture was cooled and concentrated in vacuo. Distilled water was added to the residue and extractedwith CH2Cl2. The organic layer was washed with brine anddried over anhydrous Na2SO4. Removal of solvent afforded(81) which was not purified furtherbut used immediately for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In tetrahydrofuran;Inert atmosphere; | N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide (4) (5.00 g, 20 mmol) wasdissolved in 150 mL THF, followed by the addition of triethylamine (2.35 g, 23 mmol) andpyrazin-2-ylmethanamine (2.27 g, 21 mmol). After the mixture was stirred overnight underN2 atmosphere, the solvent was removed under reduced pressure. Pure water (100 mL) wasadded to the residue, stirred for 1 hour and the precipitate was filtered and dried undervacuum to give N-(1,4-dioxo-3-((pyrazin-2-ylmethyl)amino)-1,4-dihydronaphthalen-2-yl)acetamide (5) as an orange solid (5.59 g, 87% yield). |
59.6% | With triethylamine; In ethanol; toluene; at 45℃; for 1h; | To a suspension of (85) (0.501g, 2.00mmol) in 1mL of toluene and 1mL of EtOH,pyrazin-2-ylmethylamine (0.262g, 2.4mmol) and triethylamine (0.303g, 3.00mmol)were added drop-wise and stirred at 45C for 1h. The precipitate was filteredunder suction, washed with distilled water and EtOH to afford (86) as orange solids, 59.6%.1H (D6-DMSO) delta 8.89(s, 1H), 8.51 (d, 1H, J=2.35Hz), 8.57 (s, 1H), 8.56 (d, 1H, J=1.49Hz),8.00 (d, 1H, J=7.55Hz), 7.93 (d, 1H, J=7.20Hz), 7.83 (dt, 1H, J=1.23, 7.55Hz), 7.75 (dt, 1H, J=1.27, 7.50Hz), 7.67 (br t, 1H, J=6.36Hz),4.78 (d, 2H, J=6.46Hz), 1.84 (s, 3H); 13C (D6-DMSO)delta 182.10, 178.42, 169.89, 153.76, 143.87, 143.61, 143.04, 142.93, 134.94, 132.60,132.04, 130.09, 126.05, 125.59, 112.64, 45.97, 22.43. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26.1% | With triethylamine; In ethanol; at 0 - 20℃; for 2h; | To 2,3-dichloro-5,6-dimethyl-1,4-benzoquinone(0.820g, 4.00mmol) in 1.5ml of ethanol at 0C was added pyrazin-2-ylmethylamine(0.501g, 4.60mmol) and triethylamine (0.606g, 6.00mmol) and the mixture stirredfor 1h. Subsequently, the reaction mixture was allowed to warm to room temperatureand stirred for another hour. Ethanol was removed in vacuo. Distilled water was added and extracted with EtOAc,washed with brine and dried over Na2SO4. Purification by column (1:2Hexanes/EtOAc) afforded (74) as darkpurple solids, 26.1%.1H (CDCl3) delta 8.63 (d, 1H, J=1.52Hz), 8.61 (dd, 1H, J=1.50, 2.36Hz), 8.55 (d, 1H, J=2.45Hz),6.96 (br s, 1H), 5.15 (d, 2H, J=5.16Hz), 2.10 (d, 3H, J=1.01Hz),2.02 (d, 3H, J=1.02Hz); 13C (CDCl3) delta 182.46, 179.12, 151.98,143.81, 143.70, 143.51, 143.48, 142.05, 136.49, 46.51, 13.42, 12.19. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃; for 16h;Reflux; | General procedure: To a solution of 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine (1 equiv) and diisopropylethylamine (1.5 equiv) in 2-propanol was added amine (1.2 equiv). After refluxing for 16 h, the reaction mixture was concentrated in vacuo and the appropriate solvent added to precipitate the crude product, which was collected by filtration and then purified by recrystallization, prep HPLC or column chromatography. |
Tags: 20010-99-5 synthesis path| 20010-99-5 SDS| 20010-99-5 COA| 20010-99-5 purity| 20010-99-5 application| 20010-99-5 NMR| 20010-99-5 COA| 20010-99-5 structure
[ 210037-98-2 ]
2-(Chloromethyl)pyrazine hydrochloride
Similarity: 0.71
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
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P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
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P240 | Ground/bond container and receiving equipment. |
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P243 | Take precautionary measures against static discharge. |
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P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
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P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
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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. |
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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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