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CAS No. : | 51933-78-9 | MDL No. : | MFCD03411571 |
Formula : | C6H6BrNS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CFBYLVDSPYTKPR-UHFFFAOYSA-N |
M.W : | 204.09 | Pubchem ID : | 11424251 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.66 |
TPSA : | 38.19 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) : | -5.85 cm/s |
Log Po/w (iLOGP) : | 2.21 |
Log Po/w (XLOGP3) : | 2.39 |
Log Po/w (WLOGP) : | 2.57 |
Log Po/w (MLOGP) : | 1.85 |
Log Po/w (SILICOS-IT) : | 2.6 |
Consensus Log Po/w : | 2.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.04 |
Solubility : | 0.187 mg/ml ; 0.000915 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.83 |
Solubility : | 0.3 mg/ml ; 0.00147 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.38 |
Solubility : | 0.0851 mg/ml ; 0.000417 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.72 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501 | UN#: | 1759 |
Hazard Statements: | H302-H318 | 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 |
---|---|---|
94% | In N,N-dimethyl-formamide; at 0℃; for 3.5h;Inert atmosphere;Product distribution / selectivity; | (65a) 5-Bromo-2-(methylthio)pyridine Commercially available 2,5-dibromo pyridine (6.01 g, 25.4 mmol) was dissolved in N,N-dimethylformamide (50 mL), and sodium thiomethoxide (2.20 g, 31.4 mmol) was added, followed by stirring at 0C for 3.5 hours under nitrogen atmosphere. The reaction solution was brought back to room temperature, water (250 mL) was added, and extraction was carried out with diethyl ether (250 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-5%) to afford the desired compound (4.90 g, yield 94%) as a white solid. 1H-NMR (CDCl3, 400 MHz): delta 2.54 (3H, s), 7.08 (1H, d, J=8.2 Hz), 7.58 (1H, dd, J=8.6, 2.3 Hz), 8.49 (1H, d, J=2.0 Hz). |
92% | In N,N-dimethyl-formamide; at 20℃; for 4h;Inert atmosphere; | To a stirred solution of 2, 5-dibromopyridine (180 g, 760 mmol) in DMF (1500 mL) at room temperature under argon was added sodium thiomethoxide (55.9 g, 798 mmol). The reaction mixture was stirred at room temperature for 3 h. Additional sodiumthiomethoxide (19.1 g, 272.5 mmol) was added and the reaction mixture was stirred atroom temperature for 1 h. The reaction mixture was concentrated in vacuo to 700 mL at5 0C. The residue was diluted with water (1000 mL) and the product was extracted withEt20 (4 x 500 mL). The combined organic extracts were washed with saturated aqueousNaHCO3 and brine. The organic phase was dried over MgSO4 and concentrated in vacuoto provide Intermediate lB (143.8 g, 92% yield) as a white solid. HPLC (YMCCombiScreen ODS-A S-5i 4.6 x 50 mm column, detection at 220 nm; flow rate = 4mL/min; continuous gradient from 0%B to 100% B over 4 mm + 1 mm hold time at100% B where A = 90:10:0.2 H20:MeOH:H3P04 and B = 10:90:0.2 H20:MeOH:H3P04)85.4%, rt = 3.14 mm; [M + Hj = 204.03; ?H NMR (300 MHz, CDC13) 8.45 (d, J 1.8Hz, 1H), 7.54 (dd, J= 8.6, 2.4 Hz, 1H), 7.04 (d, J= 8.4 Hz, 1H), 2.50 (s, 3H); ?3C NMR (75 JVII-Tz, CDC13) 158.6, 150.1, 138.2, 122.6, 115.6, 13.4; Anal. Calcd. for C6H6BrNS:C, 35.31; H, 2.96; N, 6.86; Found: C, 35.25%; H, 2.94%; N, 6.78%. |
50% | In water; N,N-dimethyl-formamide; at 85℃; for 24h; | 2,5-Dibromopyridine (35 g, 0.15 mol) was dissolved in 50 mL of DMF.To the above solution, 150 mL of an aqueous solution of NaSCH 3 (20%, 0.43 mol) was added.The reaction mixture was heated to 85 C for 24 hours. After cooling,The mixture was extracted with CH2Cl2. The organic phase was washed with saturated brine. After removing the solvent,The crude product was purified by column chromatography to give the compound S1(15 g, 50%, white solid). |
In DMF (N,N-dimethyl-formamide); at 20℃; for 2h; | Add sodiumthiomethoxide (1.0 g, 14.4 mmol) to a suspension OF 2, 5-DIBROMO-PYRIDINE (3.1 g, 13 mmol) in DMF (8ml) at r. t. Stir for 2 h at r. t. , dilute with water (20ml) and extract 2 times with MTBE. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 2.59 g of 5-bromo-2-methylsulfanyl-pyridine. MS (m/e): 205 (M+H). | |
In dimethyl sulfoxide; at 18 - 25℃; for 48h; | To a solution of 3, 6-dibromopyridine (1.0 eq. ) in DMSO (0.3M) was added sodium methylsulfide [(L.] leq. ). The mixture was stirred for 2d at rt then poured in water. The resulting precipitate was filtered to afford the title compound as white solid. | |
In DMF (N,N-dimethyl-formamide); at 20℃; for 0.333333h; | A mixture of 2,5-dibromopyridine and sodium thiomethoxide (1.3 eq) in N,N-dimethylformamide (2 ml/mmol) was stirred at room temperature for 20 minutes then cooled to 0 C. After diluting with cold water the precipitate was filtered to afford the 5-Bromo-2-methylthiopyridine compound as a solid. | |
In N,N-dimethyl-formamide; at 20℃; for 0.5h; | A solution of 2,5-dibromopyridine (1.0 g, 4.22 mmol) in DMF (15 mL) was treated with sodium thiomethoxide (0.69 g, 95%, 9.29 mmol) at ambient temperature. The reaction mixture was stirred for 30 minutes, was diluted water and then extracted with ether. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give crude sulfide as a colorless oil. The crude sulfide was dissolved in acetone (120 mL) and was treated with water (50 mL) followed by Oxone (7.80 g, 12.7 mmol). The reaction mixture was stirred at ambient temperature for 2 h. After more water was added, the mixture was extracted with ether (200 mL) and EtOAc (150 mL). The organic layers were combined and washed with water and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light brown oil. The crude product was purified by chromatography on ISCO silica gel column eluted with a 0 to 45% EtOAc:hexane gradient to give 0.54 g (54% from 2,5-dibromopyridine) of 5-bromo-2-(methylsulfonyl)pyridine as a white solid. 1H NMR (400 MHz, CDCl3): delta 8.78 (d, 1H, J=2.2 Hz), 8.10 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 7.98 (d, 1H, J=8.3 Hz), 3.22 (s, 3H); LRMS (ESI), m/z 236/238 (M+H). | |
In N,N-dimethyl-formamide; for 16h;Cooling with ice; Inert atmosphere; | 1. Preparation of 5-bromo-2-(methylthio)pyridine 2,5-dibromopyridine (3.0g, 12.66mmol) was dissolved in N,N-dimethyl formamide (20mL). To the resulting solution was added sodium methyl mercaptide (1.1g, 15.69mmol). The resulting mixture was placed in an ice-bath in the nitrogen protection to react with stirring for 16hrs. The reaction mixture was poured into water (150mL). The solid was separated out and filtered by suction. The resulting solid was dired to produce 2.5g of the title compound as whilte solid crude, which was directly used in the next step. | |
4.5 g | In N,N-dimethyl-formamide; at 0 - 20℃; for 12h; | To a solution of 2,5-Dibromo-pyridine (6g, 25.327 mmol) in DMF (60 mL) is added sodium thiomethoxide (1.95g, 27.86mmol) at 0C. Reaction mixture is allowed to come to room temperature and resulting reaction mixture is stirred at room temperature for 12h. Reaction mixture is quenched with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by column chromatography using silica (100-200) mesh size and using 4% ethyl acetate in hexane as an eluent to get (4.5g) of yellow solid title compound. H-NMR (400 MHz, DMSO) delta: 2.49 (s, 3H) , 7.29 (d, 1 H, J=8.76 Hz), 7.85-7.88 (dd, 1 H, J7=2.44Hz, J2=8.48Hz), 8.55 (d, 1 H, J=2.4 Hz). LC-MS (m/z): M+H = 206.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In nitrogen; N,N-dimethyl-formamide;liquid N2; | 1. Preparation of 5-bromo-2-(methylthio)pyridine 2,5-dibromopyridine (3.0 g, 12.66 mmol) was dissolved in N,N-dimethyl formamide (20 mL). To the resulting solution was added sodium methyl mercaptide (1.1 g, 15.69 mmol). The resulting mixture was placed in an ice-bath in the nitrogen protection to react with stirring for 16 hrs. The reaction mixture was poured into water (150 mL). The solid was separated out and filtered by suction. The resulting solid was dired to produce 2.5 g of the title compound as white solid crude, which was directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With Oxone; In water; isopropyl alcohol; at 20℃; | B.[00221] A solution of <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> (300 mg, 1.470 mmol) and Oxone(2078 mg, 3.38 mmol) in iPrOH (20 mL) and H2O (10 mL) was stirred at RT overnight. The solid was filtered off. The filtrate was concentrated in vacuo, then was re-dissolved in EtOAc (100 mL), and washed with H2O (2 x 20 mL) and brine (10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to give <n="110"/>Part B compound (349.2 mg, 1.479 mmol, 101 % yield) as a white solid. [M + H] =236/238. |
90% | With Oxone; In water; at 20℃; for 18h; | To a stirred solution of Intermediate lB (143 g, 701 mmol) in water (1200 mL) at room temperature was added OXONE monopersulfate (1077 g, 1752 mmol). The reaction mixture was stirred for 18 h at room temperature. The reaction mixture wasfiltered and the filter cake was washed with water and dried in vacuo to provide Intermediate 1C (148.5 g, 90% yield) as a white solid. HPLC (YMC CombiScreen ODSA S-5i 4.6 x 50 mm column, detection at 220 nm; flow rate = 4 mL/min; continuous gradient from 0%B to 100% B over 4 mm + 1 mm hold time at 100% B where A = 90:10:0.2 H20:MeOH:H3P04 and B = 10:90:0.2 H20:MeOH:H3P04) 98.7%, rt = 1.75mm; [M + Hj = 237.99; ?H NMR (300 MHz, CDC13) 8.76 (dd, J=2.2, 0.7 Hz, 1H),8.08 (dd,J= 8.4, 2.2 Hz, 1H), 7.95 (d,J= 8.1 Hz, 1H), 3.20(s, 3H); ?3CNMR(75 MHz;CDC13) 156.21, 151.1, 140.8, 125.51, 124.82, 122.4, 40.0; Anal. Calcd. forC6H6BrNO2S: C, 30.52; H, 2.56; N, 5.93; Found: C, 30.52%; H, 2.56%; N, 5.93%. |
86% | With oxone; In methanol; water; at 20℃; for 1h; | A water (20 mL) solution of potassium peroxymonosulfate (9.12 g, 0.015 mol) was added to a methanol (20 mL) solution of <strong>[51933-78-9]5-bromo-2-methylthiopyridine</strong> (2.00 g, 0.0098 mol), and the resulting mixture reacted at room temperature for 1h, then was cooled and concentrated under reduced pressure to remove methanol. The residual aqueous phase was extracted with ethyl acetate (20 mL) twice. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a white solid product (2.0 g, 86%). 1H NMR (400 MHz, CDCl3) delta 8.79 (dd, 1H), 8.11 (dd, 1H), 7.99 (dd, 1H), 3.22 (s, 3H). |
With oxone; In methanol; water; at 20℃; for 1h; | Add a suspension OF OXONE ( (4.97 g, 8.1 mmol) in 10 mL water to a solution of 5-bromo- 2-methylsulfanyl-pyridine (1. 1 g, 5.4 mmol) in 10 mL methanol, stir at r. t. for 1 h and remove methanol under vacuum. Extract the aqueous residue with dichloromethane, dry the organic extracts over sodium sulfate, filtrate and concentrate under reduced pressure to obtain 1.24 g of 5-bromo-2-methanesulfonyl-pyridine. MS (m/e): 237 (M+H). | |
With oxone; In water; acetone; at 20℃; for 2h; | A solution of 2,5-dibromopyridine (1.0 g, 4.22 mmol) in DMF (15 mL) was treated with sodium thiomethoxide (0.69 g, 95%, 9.29 mmol) at ambient temperature. The reaction mixture was stirred for 30 minutes, was diluted water and then extracted with ether. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give crude sulfide as a colorless oil. The crude sulfide was dissolved in acetone (120 mL) and was treated with water (50 mL) followed by Oxone (7.80 g, 12.7 mmol). The reaction mixture was stirred at ambient temperature for 2 h. After more water was added, the mixture was extracted with ether (200 mL) and EtOAc (150 mL). The organic layers were combined and washed with water and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light brown oil. The crude product was purified by chromatography on ISCO silica gel column eluted with a 0 to 45% EtOAc:hexane gradient to give 0.54 g (54% from 2,5-dibromopyridine) of 5-bromo-2-(methylsulfonyl)pyridine as a white solid. 1H NMR (400 MHz, CDCl3): delta 8.78 (d, 1H, J=2.2 Hz), 8.10 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 7.98 (d, 1H, J=8.3 Hz), 3.22 (s, 3H); LRMS (ESI), m/z 236/238 (M+H). | |
In water; ethyl acetate; isopropyl alcohol; | 2. Preparation of 5-bromo-2-(methylsulfonyl)pyridine 2.5 g of the crude <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> directly obtained in the above step was dissolved in a mixed solution of isopropanol (10 mL) and water (5 mL). To the resulting mixture was added a compound salt of potassium monopersulfate (15.7 g, 25.5 mmol). The resulting material was stirred overnight at room temperature and filtered. The filtrate was concentrated and then dissolved in ethyl acetate. The resulting material was successively washed with water and saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in a reduced pressure, and then purified with a silica-gel column chromatography (petroleum ether:ethyl acetate=5:1) to produce 0.43 g of the title compound as a white solid in a yield (two steps) of 14.4%. | |
0.43 g | With Oxone; In water; isopropyl alcohol; at 20℃; | 2. Preparation of 5-bromo-2-(methylsulfonyl)pyridine 2.5g of the crude <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> directly obtained in the above step was dissolved in a mixed solution of isopropanol (10mL) and water (5mL). To the resulting mixture was added a compound salt of potassium monopersulfate (15.7g, 25.5mmol). The resulting material was stirred overnight at room temperature and filtered. The filtrate was concentrated and then dissolved in ethyl acetate. The resulting material was successively washed with water and saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in a reduced pressure, and then purified with a silica-gel column chromatography (petroleum ether:ethyl acetate=5:1) to produce 0.43 g of the title compound as a white solid in a yield (two steps) of 14.4%. |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 48h; | To a cooled solution of the above mixture in dichloromethane (80 mL) was added 3- chlorobenzenecarboperoxoic acid (30.2 g, 175 mmol) in portions. The resulting mixture was stilTed at room temperature for 2 days. The reaction mixture was then washed with iN sodium hydroxide (50 mL x 2) after filtration. The organic layer was dried over sodium sulfate and thenconcentrated in vacuo to afford 9.26 g of the crude 5-bromo-2-(methylsulfonyl)pyridine (yield was 78.4%), which was used for the next step directly without any purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Compound S1 was dissolved in 20 mL of THF and cooled to -78 C.n-BuLi (2 mL, 10.3 mmol, 2.5 M) was slowly added to the above solution.Stir for 2 hours. Then DMF (0.9 g, 13.4 mmol) was slowly added and stirred for 3 hours.It was quenched by the addition of saturated aqueous NH 4Cl. The reaction mixture was extracted with diethyl ether.The extract was washed with saturated brine. The solvent was removed to give a crude product.The crude product is purified by column chromatography to give the compound S2(0.5 g, 60%, white solid) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Under the protection of N2, a 2.4 mol/L n-hexane solution of n-butyllithium (10.5 mL) was added dropwise slowly to a methylbenzene (250 mL) solution of 2,5-dibromopyridine (5.00 g, 0.021 mol) at -78C, and stirred for 2h. Then dimethyl disulfide (3.8 mL) was added dropwise slowly, and stirred for additional 1h. The resulting mixture was warmed to room temperature, a saturated of ammonium chloride aqueous solution (40 mL) was added, then ethyl acetate (100 mL) was added, and the resulting mixture was stirred for 15min. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a black residue. The residue was separated through a silica gel column (ethyl acetate/petroleum ether=1:10-1:2) to obtain a white solid product (3.8 g, 88%). 1H NMR (400 MHz, CDCl3,) delta 8.49 (d, J=1.6 Hz, 1H), 7.58 (dd, J=7.6 Hz, J=1.6 Hz, 1H), 7.07 (d, J=7.6 Hz, 1H), 2.56 (s, 3H). | |
64% | To a stirred solution of 2, 5-dibromopyridine (5.00 g, 21.11 mmol) in anhydrous toluene (300 mL) at-78QC under nitrogen was slowly added a solution of n-BuLi (10.13 mL, 25.33 mmol, 2.5M in hexanes). After 2 h at-78M, methyl disulfide (2.47 mL, 27.44 mmol) was added. The reaction mixture was stirred for 1 h at-78 and was allowed to warm to room temperature, quenched with saturated NH4CI to form a two-phase system. The organic layer was separated, washed with sat NH4CI, H20 and brine, dried over anhydrous MgS04, filtered and concentrated. The residue was purified by flash chromatography on silica gel (AcOEt/hexane, 5/95) to afford the title compound 50 (2.74 g, 13.43 mmol, 64% yield) as a pale yellow oily liquid. lu NMR (400 MHz, CDC13) 8 (ppm): 8.49 (dd, J = 2.3, 0.6 Hz, 1H), 7.60 (dd, J = 8. 5, 2.4 Hz, 1H), 7.09 (dd, J = 8.6, 0.8 Hz, 1H), 2.57 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With nitrogen; potassium acetate; triethylamine;palladium; In hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; | Preparation 9 Compounds of Formula (KB) Palladium catalyst ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1), 167 mg, 0.21 mmol), potassium acetate (1.81 g, 18.5 mmol, Aldrich), and bis(pinacolato)diboron (1.56 g, 6.1 mmol) were placed into a vial and degassed with stream of nitrogen for 20 min. In a separate vial, <strong>[51933-78-9]5-bromo-2-methylsulfanylpyridine</strong> (836 mg, 4.1 mmol) was dissolved in 8 ml anhydrous DMSO and degassed with stream of nitrogen for 20 min. The DMSO solution of <strong>[51933-78-9]5-bromo-2-methylsulfanylpyridine</strong> was added to the "catalyst" vial, and then heated at 80 C. overnight. After cooling to ambient temperature, water and ethyl acetate were added to the reaction mixture. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (10?30% EtOAC/Hexane, 0.25% Et3N in hexane) to give 2-methylsulfanyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine as a colorless oil (1.00 g, 97% yield). 1H-NMR (400 MHz, CDCl3): delta 1.35 (s, 12H), 2.58 (s, 3H), 7.16 (dd, 1H, J=1.0, J=8.0), 7.83 (dd, 1H, J=1.8, J=8.0), 8.50 (dd, 1H, J=1.7, J=1.0). |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 12h;Inert atmosphere; | 1. Preparation of 2-(methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine To 1,4-dioxane (20mL) was successively added <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> (326mg, 1.60mmol), bis(pinacolato)diboron (608mg, 2.39mmol), potassium acetate (402mg, 4.08mmol) and [1,1'-bis(diphenylphosphino)ferrocene] palladium(II) chloride dichlormethane complex(35mg), The resulting mixture was reacted under stirring in a nitrogen-protecting atmosphere at 90C for 12hrs. The reaction mixture was cooled and directly used in the next step without a further treatment. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; In tetrahydrofuran; at 40℃; for 68h; | Step 1: DBE (345, UL, 4. 0MMOL) was added to a suspension of Zn dust (2.62g, 40. 0MMOL) in anhydrous THF (4mL). The mixture was heated to boiling, then allowed to cool down to 20 C. This process was repeated three times, then the mixture was stirred at 20 C for 2h, before being treated with TMSC1 (380, UT, 3. 0MMOL). Stirring was continued for 1. 5H, then a solution of (methyl 3- cyclopentyl-2-iodoacrylate (2.52g, 9. 0MMOL) in anhydrous THF (8mL) was added over 3min. The mixture was stirred at 40 C for 2h, before being stirred at 20 C for 16h, and finally allowed to stand for 4h. In a separate reaction vessel, a solution of PPh3 (315mg, 1. 2MMOL) and Pd2 (dba) 3 (150MG, 0. 5MMOL) in anhydrous THF (15ML) was stirred for 2h at 20 C, before being treated with a solution of 5-bromo-2- methylsulfanylpyridine (2.76g, 13. 5MMOL) in anhydrous THF (lOmL). The solution of the freshly prepared organozinc compound was then added via cannula, and the mixture was stirred at 40 C for 68h. Solvent evaporation and column chromatography (4: 1 IH-Et2O) yielded methyl 3-cyclopentyl-2- (6-methylsulfanylpyridin-3-yl) acrylate: MLZ (ES+) = 278.1 [M+ H] +. Step 2: A solution of this compound (1.12g, 4. 0MMOL) in MEOH (5. 5ML) was treated with 1M NAOH (8.9mL, 8. 9MMOL). The mixture was heated at 65 C for 3h, before being stirred at 20 C for 16h. The MEOH was removed under reduced pressure, then H20 (lOmL) and 1M NAOH (lOmL) were added. The resulting mixture was washed with Et2O (25mL), before being acidified with 2M HC1 to adjust the pH to 1. The suspension produced was extracted with EtOAc (2 x 50ML), then the extracts were washed with brine (20mL), before being dried (MGS04). Filtration, solvent evaporation, and recrystallisation (ETOAC-IH) furnished the title compound: mlz (ES+) = 264.1 [M+ H] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | To a stirred solution of 50 (2.74 g, 13.43 mmol) and triisopropylborate (3.72 mL, 16.11 mmol) in a mixture of anhydrous toluene/THF (20 mL/5 mL) at-40 under nitrogen was added dropwise a solution of n-BuLi (6.98 mL, 17.45 mmol, 2.5M in hexanes). After stirring for 1 h at-40CC, the mixture was allowed to warm to room temperature and quenched with 2N HCI. The resultant suspension was filtered ; the precipitate was rinsed with H20 and AcOEt. The filtrate was neutralized with 1N NaOH (pH 7) and extracted with AcOEt. The organic layer and the precipitate were combined, solvent was evaporated and the solid residue was triturated with MeCN-MeOH to afford the title compound 51 (1.84 g, 10.88 mmol, 81% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In water; ethyl acetate; N,N-dimethyl-formamide; | A. 2,5-Dibromo-pyridine (3.0 g, 12.7 mmol) and sodium thiomethoxide (0.84 g, 12 mmol) were dissolved in 18 ml anhydrous N,N-dimethylformamide. The mixture was heated at 160 C. under nitrogen for 6 hrs. After cooling to ambient temperature, water and ethyl acetate were added to the reaction mixture. The aqueous layer was extracted with ethyl acetate several times. The combined extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (06% EtOAC/Hexane) to give 5-bromo-2-methylsulfanylpyridine as a white solid (2.18 g, 84% yield). 1H-NMR (400 MHz, CDCl3): delta 2.55 (s, 3H), 7.09 (dd, 1H, J=0.7, J=8.6), 7.59 (dd, 1H, J=2.4, J=8.6), 8.50 (m, 1H). |
In N,N-dimethyl-formamide; | Step 1 5-Bromo-2-Methylthiopyridine A mixture of 2,5-dibromopyridine and sodium thiomethoxide (1.3 eq) in N,N-dimethylformamide (2 ml/mmol) was stirred at room temperature for 20 minutes then cooled to 0 C. After diluting with cold water the precipitate was filtered to afford the 5-Bromo-2-methylthiopyridine compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 20℃; for 3h;Heating / reflux; | Intermediate 19; 4-(6-Methylsulfanylpyridin-3-yl)piperazine-l-carboxylic acid terf-butyl ester; EPO <DP n="53"/>A mixture of <strong>[51933-78-9]5-bromo-2-methylsulfanylpyridine</strong> (1.06g, 5.2 mmol), 1-boc-piperazine (0.967g, 5.2 mmol), sodium tert-butoxide (0.749g, 7.8 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (0.179g, 0.31 mmol) in toluene (3OmL) was treated with Pd2(dba)3 (0.095g, 0.1 mmol) at rt. The mixture was refluxed for 3h. The reaction was cooled and filtered through celite. The organic layer was diluted with EtOAc (10OmL) then washed with saturated Na2CO3 solution, brine, dried (MgSO4) and the solvent removed in vacuo. The crude mixture was purified by flash chromatography with 20% EtOAc / Hexane as eluent to afford the title compound (1.Og, 61%): RT = 3.22 min; m/z (ES+) = 310.2 [M+ H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(65b) 5-Fluoro-2-(methylsulfonyl)pyridine 5-Bromo-2-(methylthio)pyridine (4.90 g, 24.0 mmol) synthesised in Example (65a) was dissolved in tetrahydrofuran (100 mL), and n-butyl lithium (1.57 mol/L hexane solution, 17.0 mL, 26.7 mmol) was added dropwise at -78C, followed by stirring at -78C for 1 hour under nitrogen atmosphere. N-fluorobenzenesulfonimide (11.0 g, 34.9 mmol) was dissolved in tetrahydrofuran (25 mL), followed by dropwise addition to the reaction solution at -78C, and stirring was carried out at -78C for 2 hours under nitrogen atmosphere. The reaction solution was brought back to room temperature, and stirring was carried out for 1.5 hours. A saturated aqueous ammonium chloride solution (200 mL) was added, and extraction was carried out with diethyl ether (300 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under slightly reduced pressure. The resulting residue was dissolved in methylene chloride (150 mL), and m-chloroperbenzoic acid (65%, 16.5 g, 62.1 mmol) was slowly added at 0C, followed by stirring at 0C for 1.5 hours under nitrogen atmosphere. After removal of white solid material by Celite filtration, a saturated aqueous sodium hydrogencarbonate solution (100 mL) was added, and extraction was carried out with methylene chloride (400 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-5%) to afford the desired compound (1.95 g, yield 46%) as a yellowish white solid. 1H-NMR (CDCl3, 400 MHz): delta 3.24 (3H, s), 7.67 (1H, ddd, J=9.9, 6.9, 1.9 Hz), 8.16 (1H, dd, J=8.6, 4.3 Hz), 8.59 (1H, d, J=2.7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | [Example 18] Preparation of 4-(4-chlorobenzyl)-2-dimethyl-amino-5-(4-isopropoxybenzyl)pyridine (I-165) To a mixture of <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> (7.50 g, 36.6 mmol) and THF (37.5 mL) was added dropwise isopropylmagnesium chloride / lithium chloride (1.3 mol/L in THF, 31.0 ml) at room temperature over 30 minutes, and the resulting mixture was stirred at room temperature for 15 minutes. A solution of 4-isopropoxybenzaldehyde (9.01 g, 54.9 mmol) in THF (37.5 ml) was added gradually at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride (300 mL), and the mixture was extracted with ethyl acetate (300 mL*3). The extract was dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 5-(4-isopropoxy-alpha-hydroxybenzyl)-2-(methylthio)pyrimidine (4.86 g, Yield: 46%) as orange oil. 1H-NMR (delta ppm TMS/DMSO-d6): 1.23 (6H, d, J = 6.1 Hz), 2.50 (3H, s), 4.56 (1H, sept, J=6.0 Hz), 5.70 (1H, d, J = 3.8 Hz), 6.06 (1H, d, J=4.0 Hz), 6.86 (2H, d, J=8.6 Hz), 7.28 (2H, d, J=8.6 Hz), 8.56 (s, 2H). | |
46% | EXAMPLE 18 Preparation of 4-(4-chlorobenzyl)-2-dimethyl-amino-5-(4-isopropoxybenzyl)pyridine (I-165) To a mixture of <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> (7.50 g, 36.6 mmol) and THF (37.5 mL) was added dropwise isopropylmagnesium chloride/lithium chloride (1.3 mol/L in THF, 31.0 ml) at room temperature over 30 minutes, and the resulting mixture was stirred at room temperature for 15 minutes. A solution of 4-isopropoxybenzaldehyde (9.01 g, 54.9 mmol) in THF (37.5 ml) was added gradually at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride (300 mL), and the mixture was extracted with ethyl acetate (300 mL*3). The extract was dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 5-(4-isopropoxy-alpha-hydroxybenzyl)-2-(methylthio)pyrimidine (4.86 g, Yield: 46%) as orange oil. 1H-NMR (delta ppm TMS/DMSO-d6): 1.23 (6H, d, J=6.1 Hz), 2.50 (3H, s), 4.56 (1H, sept, J=6.0 Hz), 5.70 (1H, d, 3.8 Hz), 6.06 (1H, d, J=4.0 Hz), 6.86 (2H, d, J=8.6 Hz), 7.28 (2H, d, J=8.6 Hz), 8.56 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56%; 8% | LDA (33.0 mmol) was added slowly to a suspension of 2b (15.0 mmol) in diethyl ether at 78 C. A reddish brown solutioncontaining the dilithiated species (DL-2b) was formed. DMDS(3.10 g, 33.0 mmol) was added to it at 78 C. The reaction mixture was hydrolyzed and purified by column chromatography (60e120mesh silica gel and 2% EtOAc/hexane) to provide the title compound10b (1.72 g, 56%) as a white solid; mp 34e36 C; [Found: C,35.42, H, 2.94, N, 6.84, S, 15.97. C6H6NBrS requires C, 35.31, H, 2.96,N, 6.86, S, 15.70%]; Rf (5% EtOAc/hexane) 0.88; 1H NMR (400 MHzCDCl3) d 8.47e8.48 (d, J2.52 Hz, 1H), 7.55e7.58 (dd, J2.40,8.56 Hz, 1H), 7.05e7.07 (dd, J0.60, 8.72 Hz, 1H), 2.53 (s, 3H); 13CNMR (100 MHz CDCl3) d 158.7, 150.2, 138.2, 122.6, 115.7, 13.4; MS m/z 205 (M, 69), 170 (19), 157 (31), 78 (100), 50 (52%).3-Bromo-2,6-bis(methylsulfanyl)pyridine (11b) The compound 11b (0.3 g, 8%) was obtained from the above reaction as a yellowish liquid; [Found: C, 33.63, H, 3.21, N, 5.61, S, 25.91.C7H8NBrS2 requires C, 33.60, H, 3.22, N, 5.59, S, 25.63%]; Rf (100% hexane) 0.96; 1H NMR (400 MHz CDCl3) delta 7.37-7.39 (d, J=8.20 Hz, 1H), 6.69-6.71 (d, J=8.20 Hz, 1H), 2.50 (s, 6H); 13C NMR (100 MHz CDCl3) delta 158.4, 157.8, 138.6, 117.4, 113.5, 14.3, 13.5; MS m/z 251 (M+, 100), 236 (7), 217 (68), 170 (71), 155 (36), 136 (69), 124 (43), 109 (28), 96 (29), 78 (12%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; | 1. Preparation of 2-(methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine To 1,4-dioxane (20 mL) was successively added <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> (326 mg, 1.60 mmol), bis(pinacolato)diboron (608 mg, 2.39 mmol), potassium acetate (402 mg, 4.08 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichlormethane complex (35 mg), The resulting mixture was reacted under stirring in a nitrogen-protecting atmosphere at 90 C. for 12 hrs. The reaction mixture was cooled and directly used in the next step without a further treatment. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.7 g | With N-Bromosuccinimide; potassium tert-butylate; In methanol; water; at 0℃; for 1h; | To a solution of 5-Bromo-2-methylsulfanyl-pyridine (4.5g, 22.059mmol) in methanol (50 ml_) is added t-BuOK (2.965g, 26.471 mmol), NH2CN (50% aqueous solution) (2.638g, 28.676mmol) and NBS (5.89g, 33.088mmol) at 0C. The resulting reaction mixture is stirred at 0C for 1 h. Solvent is evaporated in vacuo, reaction mixture is quenched with aqueous sodium metabisulphate solution and extracted with DCM. Organic layer is dried over sodium sulphate, concentrated and purified by silica gel column chromatography (100-200 mesh size) using 3% methanol in DCM as an eluent to give the title compound (4.7g) as a yellow solid. LC-MS (m/z): M+H = 243.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 20℃; for 3h; | A mixture of 2-chloro-5-bromo-pyridine (9.80 g, 50.0 mmol, CAS No.: 53939-30-3) and sodium methanethiolate (5.25 g, 75.0 mmol, CAS No.: 5 188-07-8) in N,N-dimethylformamide (25 mL) was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (50 mL) and then extracted with ethyl acetate (60 mL x 3). The combined organic layer was washed with brine (100 mL x 2), and then dried over sodium sulfate and then concentrated in vacuo to afford a mixture of 5-bromo-2-(methylsulfanyl)pyridine and 2,5- bis(methylsulfanyl)pyridine, which was used directly for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium periodate; acetic acid; In water; at 20℃; for 2h; | NaI04(9.56 g, 44.69 mmol) was added as a slurry in water (10 mL) to a stirred solution of <strong>[51933-78-9]5-bromo-2-(methylsulfanyl)pyridine</strong> (2.4 g, 11.76 mmol) in acetic acid (40 - -mL) at r.t.. The mixture was stirred at r.t. for 2 h. After this time, a colourless precipitate had formed. The mixture was treated with water (50 mL) upon which the precipitate dissolved. The aqueous acidic mixture was basified through addition of saturated aqueous potassium carbonate solution and the product extracted with EtOAc (3 x 50 mL). The combined organic phase was washed with 10 % aqueous sodium thiosulfate solution (50 mL), dried (Na2S04) and reduced in vacuo to give the crude product as an amber glass (2.52 g) which solidified on standing. Purification by chromatography (Si02, 0-100% EtOAc in heptane) afforded the title compound as a pale yellow oil (2.04 g, 79%). deltaEta (500 MHz, CDCls) 8.68 (d, J 2.0 Hz, 1H), 8.08 (dd, J 8.3, 2.2 Hz, 1H), 7.93 (d, J 8.3 Hz, 1H), 2.84 (s, 3H). |
79% | With sodium periodate; acetic acid; In water; at 20℃; for 2h; | Na104 (9.56 g, 44.69 mmol) was added as a slurry in water (10 mL) to a stirred solution of <strong>[51933-78-9]5-bromo-2-(methylsulfanyl)pyridine</strong> (2.4 g, 11.76 mmol) in acetic acid (40 mL) at r.t.. The mixture was stirred at r.t. for 2 h. After this time, a colourless precipitate had formed. The mixture was treated with water (50 mL) upon which the precipitatedissolved. The aqueous acidic mixture was basified through addition of saturated aqueous potassium carbonate solution and the product extracted with EtOAc (3 x 50 mL). The combined organic phase was washed with 10 % aqueous sodium thiosulfate solution (50 mL), dried (Na2SO4) and reduced in vacuo to give the crude product as an amber glass (2.52 g) which solidified on standing. Purification by chromatography (Si02, 0-100% EtOAc in heptane) afforded the title compound as a pale yellow oil (2.04 g, 79%). oH(500 MHz, CDCl3) 8.68 (d, J 2.0 Hz, 1H), 8.08 (dd, J 8.3, 2.2 Hz, 1H), 7.93 (d, J 8.3 Hz, 1H), 2.84 (s, 3H). |
79% | With sodium periodate; acetic acid; In water; at 20℃; for 2h; | NaI04 (9.56 g, 44.69 mmol) was added as a slurry in water (10 mL) to a stirred solution of <strong>[51933-78-9]5-bromo-2-(methylsulfanyl)pyridine</strong> (2.4 g, 11.76 mmol) in acetic acid (40 mL) at room temperature. The mixture was stirred at room temperature for 2 h. After this time, a colourless precipitate had formed. The mixture was treated with water (50 mL), upon which the precipitate dissolved. The aqueous acidic mixture was basified through addition of saturated aqueous potassium carbonate solution and the resulting material was extracted with EtOAc (3 x 50 mL). The combined organic phase was washed with 10% aqueous sodium thiosulfate solution (50 mL), then dried (Na2S04) and reduced in vacuo. The resulting crude amber glass (2.52 g) solidified on standing. Purification by chromatography on silica gel, eluting with 0-100% EtOAc in heptanes, afforded the title compound (2.04 g, 79%) as a pale yellow oil which solidified on standing. deltaEta (500 MHz, CDC13) 8.68 (d, J2.0 Hz, IH), 8.08 (dd, J 8.3, 2.2 Hz, IH), 7.93 (d, J 8.3 Hz, 1H), 2.84 (s, 3H). |
With sodium periodate; acetic acid; In water; at 20℃; for 2h; | Na104 (9.56 g, 44.69 mmol) was added as a slurry in water (10 mL) to a stirredsolution of <strong>[51933-78-9]5-bromo-2-(methylsulfanyl)pyridine</strong> (2.4 g, 11.76 mmol) in acetic acid (40mL) at room temperature. The mixture was stirred at room temperature for 2 h. Afterthis time, a colourless precipitate had formed. The mixture was treated with water (50mL), upon which the precipitate dissolved. The aqueous acidic mixture was basifiedthrough addition of saturated aqueous potassium carbonate solution and the resulting material was extracted with EtOAc (3 x 50 mL). The combined organic phase was washed with 10% aqueous sodium thiosulfate solution (50 mL), then dried (Na2SO4) and reduced in vacuo. The resulting crude amber glass (2.52 g) solidified on standing.Purification by chromatography on silica gel, eluting with 0-100% EtOAc in heptanes, afforded the title compound (2.04 g, 79%) as a pale yellow oil which solidified onstanding. H (500 MHz, CDC13) 8.68 (d,J2.0 Hz, 1H), 8.08 (dd,J8.3, 2.2 Hz, 1H), 7.93(d,J8.3 Hz, 1H), 2.84 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8 mg | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 88℃; for 2h; | To <strong>[51933-78-9]5-bromo-2-(methylthio)pyridine</strong> (14.0 mg, 0.07 mmol), were added 1,2-dimethoxyethane (1.5 mL) and Pd(PPh3)4 (8.4 mg, cat.). To the reaction mixture, were added 1-(2-chloro-phenyl)-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (25.0 mg, 0.05 mmol) prepared in Step 1, ethanol 183.0 uL, and a 2N sodium carbonate solution (183.0 uL). The reaction mixture was stirred at 88 C. for 2 hours and then distilled water was added thereto. The reaction mixture was extracted with diethyl ether two times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 8.0 mg of the titled compound as a white liquid. (0755) 1H NMR (400 MHz, CDCl3) 8.58 (s, 1H), 7.60 (d, 1H), 7.40 (d, 2H), 7.28-7.18 (m, 5H), 7.10 (t, 1H), 6.97 (t, 1H), 5.92 (dd, 1H), 4.94 (s, 1H), 3.66 (dd, 1H), 3.22 (dd, 1H), 2.58 (s, 3H) |
Tags: 51933-78-9 synthesis path| 51933-78-9 SDS| 51933-78-9 COA| 51933-78-9 purity| 51933-78-9 application| 51933-78-9 NMR| 51933-78-9 COA| 51933-78-9 structure
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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 |
Sorry,this product has been discontinued.
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