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Limited Quantity | USD 15-60 |
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CAS No. : | 93933-49-4 | MDL No. : | MFCD09909742 |
Formula : | C6H6BrNS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WKEYPPZTEITNHZ-UHFFFAOYSA-N |
M.W : | 204.09 | Pubchem ID : | 12199294 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.8 |
TPSA : | 64.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 1.74 |
Log Po/w (XLOGP3) : | 2.08 |
Log Po/w (WLOGP) : | 2.33 |
Log Po/w (MLOGP) : | 2.51 |
Log Po/w (SILICOS-IT) : | 2.1 |
Consensus Log Po/w : | 2.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.91 |
Solubility : | 0.252 mg/ml ; 0.00123 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.07 |
Solubility : | 0.173 mg/ml ; 0.00085 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.01 |
Solubility : | 0.201 mg/ml ; 0.000984 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.48 |
Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 | UN#: | 2923 |
Hazard Statements: | H301-H312-H332-H314 | 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 |
---|---|---|
24% | Stage #1: for 18 h; Reflux Stage #2: With hydrogenchloride In water for 12 h; |
To a solution of2-amino-4-bromobenzenethiol (500 mg,2.50 mmol)in acetic acid (25mL)was added triphosgene (490 mg,1.70 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature,the solution was partially concentrated under reducedpressure,water was added,and the resulting precipitate was removed via filtration,and washedwith aqueous NaOH (1M). The filtrate was acidified with aqueous HCl (2 N)to pH 2,and placed in a refrigerator for 12 h. The resulting precipitate was filtered,washed with water,anddried under reduced pressure to give the title compound (133 mg,24percent)as a while powder thatrequired no further purification. 1H NMR (400 MHz,DMSO-d6)8 10.97 (s,1H),7.33 (d,J = 1.9Hz,1H),7.13 (dd,J = 8.2,1.9 Hz,1H),6.91 (d,J = 8.2 Hz,1H),3.26 (s,3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | for 18 h; Reflux | To a solution of2-amino-4-bromobenzenethiol (544 mg,2.67 mmol)in acetic acid (26.7mL)was added triphosgene (530 mg,1.79 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature,the solution was partially concentrated under reducedpressure,water was added,and the resulting precipitate was removed via filtration,and washed with aqueous NaOH (1.0 M). The filtrate was acidified with HCl (2 N)to pH 2,and placed in arefrigerator for 12 h. The resulting precipitate was filtered,washed with water,and dried underreduced pressure to give the title compound (94 mg,15percent)as a while powder that required nofurther purification. 1H NMR (400 MHz,DMSO-d6)8 12.07 (s,1H),7.55 (d,J = 8.4 Hz,1H),5 7.30 (d,J = 8.0 Hz,1H),7.24 (s,1H). |
20 g | at 0℃; for 18 h; Reflux | Zn (70 g, 1077 mmol) was added to a solution of B (28 g, 120 mmol) in AcOH (500 ml). Reaction mixture was stirred at 65°C for 15 h under nitrogen to give C, monitored by TLC. The mixture was cooled to room temperature, and triphosgene (25 g, 84 mmol) added slowly at 0°C. Mixture was refluxed for 18 h, monitored by TLC. Solution was then concentrated and hydrolyzed with water. Yellow solid was collected to give D (20 g, 73percent, over two steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tin |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In dimethyl sulfoxide for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In dimethyl sulfoxide for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In dimethyl sulfoxide for 1h; | |
With dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In dimethyl sulfoxide for 1h; | |
With dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In dimethyl sulfoxide for 1h; | |
With dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In dimethyl sulfoxide for 1h; | |
With dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With piperidine In ethanol for 0.05h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine at 0 - 20℃; for 48h; | 2.C EXAMPLE 2C; 6-Bromo-3-hydroxy-4H-benzo[1,4]thiazine-2-carboxylic acid ethyl ester The crude product solution from the previous step is stripped to a volume of 300 mL of pyridine. 2-Amino-4-bromo-benzenethiol dimer (64.1 mmol) in pyridine (40 mg/mL) solution is cooled to 0° C. under nitrogen. Chlorocarbonyl-acetic acid ethyl ester (25 g, 0.167 mol) is added drop wise and then warmed to room temperature. Reaction is stirred at room temperature for 2 days. Many transition peaks are observed by HPLC during the reaction. Reaction is extracted with CHCl3 and washed with water several times to remove pyridine. Crude material is carried on to the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In tetrahydrofuran at 50℃; for 41h; | 2.B EXAMPLE 2B; 2-Amino-4-bromo-benzenethiol Dissolved the crude 4-bromo-2-nitro-benzenethiol and dimer (14.9 g, 53.5 mmol) in THF (450 mL) and charged Raney Ni (30 g, 100% wt) into a 1000 mL parr shaker with a hydrogen pressure of 40 psi. Reacted at 50° C. for 41 hr and monitored by HPLC for conversion. Reaction was complete. Filtered. Filtrate contained the over reduced product bromo aniline. Solid filter-cake is dissolved in pyridine (600 mL) at 100° C. and filtered to remove the Ni residue. This contains mostly the 2-amino-4-bromo-benzenethiol dimer dimer. Crude yield=11.9 g (92%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine | 2.C 6-Bromo-3-hydroxy4H-benzo[1,4]thiazine-2-carboxylic acid ethyl ester Example 2C 6-Bromo-3-hydroxy4H-benzo[1,4]thiazine-2-carboxylic acid ethyl ester The 2-amino4-bromophenyldisulfide solution in pyridine from Example 2B was concentrated in vacuo to a volume of 300 mL and cooled to 0° C. under nitrogen. Chlorocarbonyl-acetic acid ethyl ester (25 g, 0.167 mol) was added dropwise and the mixture was warmed to room temperature and stirred for 2 days. The mixture was extracted with CHCl3 and washed with water several times to remove pyridine. Evaporation of the chloroform solutions gave the crude material (6-bromo-3-hydroxy-4H-benzo[1,4]thiazine-2-carboxylic acid ethyl ester) which was carried on to the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.9 g (92%) | In tetrahydrofuran; pyridine; hydrogen | 2.B 2-Amino-4-bromo-benzenethiol Example 2B 2-Amino-4-bromo-benzenethiol The mixture of 4-bromo-2-nitro-benzenethiol and its disulfide from Example 2A (14.9 g, 53.5 mmol) in THF (450 mL) was mixed with Raney Ni (30 g, 100% wt). The mixture was hydrogenated in a 1000 mL Paar shaker at a hydrogen pressure of 40 psi at 50° C. for 41 hours. When the reaction was complete, the solids were filtered. The solid filter-cake was dissolved in pyridine (600 mL) at 100° C. and filtered to remove the Ni residue. This pyridine solution contained mostly the 2-amino-4-bromophenyidisulfide. Crude yield=11.9 g (92%) |
With acetic acid; zinc at 65℃; for 15h; Inert atmosphere; | Zn (70 g, 1077 mmol) was added to a solution of B (28 g, 120 mmol) in AcOH (500 ml). Reaction mixture was stirred at 65°C for 15 h under nitrogen to give C, monitored by TLC. The mixture was cooled to room temperature, and triphosgene (25 g, 84 mmol) added slowly at 0°C. Mixture was refluxed for 18 h, monitored by TLC. Solution was then concentrated and hydrolyzed with water. Yellow solid was collected to give D (20 g, 73%, over two steps). | |
With palladium on activated charcoal; hydrogen |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium sulfide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: zinc; acetic acid / 15 h / 65 °C / Inert atmosphere | ||
With sodiumsulfide nonahydrate In water at 100℃; for 24h; | 97.A Step A: 2-amino-4-bromobenzenethiol Step A: 2-amino-4-bromobenzenethiol A 250 mL round bottom flask was charged with l,4-dibromo-2-nitrobenzene (7 g, 24.92 mmol), Na2S-9H20 (59.9 g, 249 mmol) and water (80 mL). The reaction was heated to 100 °C and stirred for 24 hr. Then the reaction mixture was extracted with EtOAc (50 mL*4) to remove by-product. The aqueous layer was acidfied to pH=7 by cone. HC1. The resulting solution was extracted with EtOAc (50 mL*4). The organic layers were combined and dried over a2S04, filtered and evaporated to give the crude product 2-amino-4-bromobenzenethiol, which was used in the next step directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With acetic acid; for 18h;Reflux; | To a solution of2-amino-4-bromobenzenethiol (544 mg,2.67 mmol)in acetic acid (26.7mL)was added triphosgene (530 mg,1.79 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature,the solution was partially concentrated under reducedpressure,water was added,and the resulting precipitate was removed via filtration,and washed with aqueous NaOH (1.0 M). The filtrate was acidified with HCl (2 N)to pH 2,and placed in arefrigerator for 12 h. The resulting precipitate was filtered,washed with water,and dried underreduced pressure to give the title compound (94 mg,15%)as a while powder that required nofurther purification. 1H NMR (400 MHz,DMSO-d6)8 12.07 (s,1H),7.55 (d,J = 8.4 Hz,1H),5 7.30 (d,J = 8.0 Hz,1H),7.24 (s,1H). |
20 g | for 18h;Reflux; | Zn (70 g, 1077 mmol) was added to a solution of B (28 g, 120 mmol) in AcOH (500 ml). Reaction mixture was stirred at 65C for 15 h under nitrogen to give C, monitored by TLC. The mixture was cooled to room temperature, and triphosgene (25 g, 84 mmol) added slowly at 0C. Mixture was refluxed for 18 h, monitored by TLC. Solution was then concentrated and hydrolyzed with water. Yellow solid was collected to give D (20 g, 73%, over two steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With water; sodium hydroxide; In ethylene glycol; at 140℃; for 4h; | To a stirring solution of 5-bromo-2-methylbenzo[djthiazole (5 g, 22.02 mmol) in ethylene glycol (50 mL) was added 8N sodium hydroxide solution (50 mL) and the resulting reaction mixture was stirred at 140 C for 4 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under reduced pressure to get a crude residue, which was purified by triturating it with pentane/ether to afford the title compound as a yellow solid (4.3 g, 96% yield). ?H NMR (400 MHz, DMSO-d6) = 7.09 (d, J=8.33 Hz, 1H), 6.87 (d, J=1.75 Hz, 1H), 6.62 (dd, J=1.75, 8.33 Hz, 1H), 5.16 (br. s, 3H). LCMS: [M+Hj = 203.83; R = 3.10 mm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; sodium iodide In water; ethyl acetate at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In toluene at 110℃; for 20h; | 97.B Step B: 6-bromo-2-(4-(trifluoromethyl)phenyl)-2H-benzo[b][l,4]thiazin-3(4H)-one Step B: 6-bromo-2-(4-(trifluoromethyl)phenyl)-2H-benzo[b][l,4]thiazin-3(4H)-one A 30 mL vial was charged with 2-amino-4-bromobenzenethiol (1.312 g, 6.43 mmol),ethyl 2-bromo-2-(4-(trifluoromethyl)phenyl)acetate (2 g, 6.43 mmol), DIPEA (3.37 mL, 19.29 mmol) and toluene (20 mL). The mixture was stirred at 110 °C for 20 hr. TLC (Petroleum ether: EtOAc= 8: 1) showed the product was formed (R^0.3). The reaction mixture was poured into water and extracted with EtOAc (50 mL*3). The combined organic layers were evaporated to dryness. The residue was purificed via silica gel column chromatography (EtOAc in Petroleum ether form 0% to 25%) to give 6-bromo-2-(4-(trifluoromethyl)phenyl)-2H- benzo[b][l,4]thiazin-3(4H)-one as a solid. 'H NMR (Cods, 400 MHz): δ 8.56 (brs, 1H), 7.59 (d, J= 8.3 Hz, 2H), 7.50 (d, J= 8.3 Hz, 2H), 7.21 (d, J= 8.0 Hz, 1H), 7.16 (dd, J= 8.0 Hz, 1.8Hz, 1H), 7.04 (d, J= 1.7 Hz, 1H), 4.74 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water at 20℃; for 20h; | 99.A Step A: 6-bromo-3 -(4-(trifluoromethyl)phenyl)-2H-benzo [b] [ 1 ,4]thiazine Step A: 6-bromo-3 -(4-(trifluoromethyl)phenyl)-2H-benzo [b] [ 1 ,4]thiazine To a solution of 2-amino-4-bromobenzenethiol (1 g, 4.90 mmol) in DCM (20 mL) were added K2CO3 (15 mL, 4.45 mmol) in water (15 mL) and tetrabutylammonium hydrogen sulfate (0.015 g, 0.045 mmol), then 2-bromo- 1 -(4-(trifluoromethyl)phenyl)ethanone (1.190 g, 4.45 mmol) in DCM (5 mL) was added dropwise to the reaction mixture. The resulting mixture was stirred at room temperature for 20 h. LCMS showed the desired compound was formed, then the mixture was extracted with DCM (100 mL*3). The combined organic layers were washed with brine (100 mL*3), dried over Na2S04, filtered and concentrated in vacuo to give 6-bromo-3-(4- (trifluoromethyl)phenyl)-2H-benzo[b][l,4]thiazine as an oil, which was used in the next step directly. LC/MS (m/z): 373 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.2% | In dimethyl sulfoxide at 140℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: 2-amino-4-bromobenzenethiol; dimethyl acetylenedicarboxylate at 0℃; for 0.333333h; Stage #2: diethyl malonate In isopropyl alcohol at 50℃; for 7h; | Typical procedure for preparation of 4 General procedure: A mixture of acetylenic ester (1.0mmol) and 2-aminobenzenethiol (1.0 mmol) was stirredat 0°C for 20 min. A solution of malonate source (3.0 mmol) and HPA (0.1 mmol or 100 mg of supported HPA) in i-PrOH (3 ml) was then added to the initial mixture in one portion. The resultingmixture was heated to 50°C for 7 h. After completion of the reaction, it was filtered and then diluted by EtOAc (5 mL) and saturated NH4Cl solution (5 mL). The mixture was stirred for additional 30 min and two layers were separated. The aqueous layer was extracted with EtOAc (7mL×3). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuum. The residue was purified by chromatography (silicagel, hexane:EtOAc 3:1) to give the pure product (see ESI for characterization data for all products). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C | ||
Multi-step reaction with 3 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: methanol; tetrahydrofuran / 12 h / 20 °C | ||
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: methanol; tetrahydrofuran / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: methanol; tetrahydrofuran / 12 h / 20 °C 5: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C | ||
Multi-step reaction with 5 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: methanol; tetrahydrofuran / 12 h / 20 °C 5: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 3 h / 80 °C | ||
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 0 - 20 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 2.16 h / 0 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 3 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane | ||
Multi-step reaction with 5 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 0 - 20 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 2.16 h / 0 - 40 °C 5: N-ethyl-N,N-diisopropylamine / dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 3 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane 4: methanol / 6 h / 20 °C | ||
Multi-step reaction with 6 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 0 - 20 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 2.16 h / 0 - 40 °C 5: N-ethyl-N,N-diisopropylamine / dichloromethane 6: methanol / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 3 h / 80 °C 3: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 2.5 h / 60 °C / Inert atmosphere | ||
Multi-step reaction with 5 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 0 - 20 °C 4: acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 2.16 h / 0 - 40 °C 5: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 2.5 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: 4-methylmorpholine N-oxide / chloroform / 12 h / 25 °C | ||
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: 4-methylmorpholine N-oxide / chloroform / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C | ||
Multi-step reaction with 4 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere | ||
Multi-step reaction with 5 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6: triethylamine / dichloromethane / 16 h / 20 °C | ||
Multi-step reaction with 6 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6: triethylamine / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: acetic acid / ethanol / 16 h / 80 °C 2.1: sulfur; morpholine / ethanol / 16 h / 80 °C 3.1: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4.1: methanol; tetrahydrofuran / 16 h / 20 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 16 h / 20 °C 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; toluene / 0.02 h / 20 °C 7.2: 16 h / 20 °C | ||
Multi-step reaction with 7 steps 1.1: acetic acid / ethanol / 16 h / 80 °C 2.1: sulfur; morpholine / ethanol / 16 h / 80 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4.1: methanol; tetrahydrofuran / 16 h / 20 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 16 h / 20 °C 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; toluene / 0.02 h / 20 °C 7.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: acetic acid / ethanol / 16 h / 80 °C 2.1: sulfur; morpholine / ethanol / 16 h / 80 °C 3.1: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4.1: methanol; tetrahydrofuran / 16 h / 20 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 16 h / 20 °C 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; toluene / 0.02 h / 20 °C 7.2: 16 h / 20 °C 8.1: Oxone / N,N-dimethyl-formamide / 16 h / 20 °C | ||
Multi-step reaction with 8 steps 1.1: acetic acid / ethanol / 16 h / 80 °C 2.1: sulfur; morpholine / ethanol / 16 h / 80 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4.1: methanol; tetrahydrofuran / 16 h / 20 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 16 h / 20 °C 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; toluene / 0.02 h / 20 °C 7.2: 16 h / 20 °C 8.1: Oxone / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: acetic acid / ethanol / 16 h / 80 °C 2.1: sulfur; morpholine / ethanol / 16 h / 80 °C 3.1: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4.1: methanol; tetrahydrofuran / 16 h / 20 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 16 h / 20 °C 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; toluene / 0.02 h / 20 °C 7.2: 16 h / 20 °C 8.1: Oxone / N,N-dimethyl-formamide / 16 h / 20 °C 9.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C | ||
Multi-step reaction with 9 steps 1.1: acetic acid / ethanol / 16 h / 80 °C 2.1: sulfur; morpholine / ethanol / 16 h / 80 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4.1: methanol; tetrahydrofuran / 16 h / 20 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6.1: triethylamine / dichloromethane / 16 h / 20 °C 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; toluene / 0.02 h / 20 °C 7.2: 16 h / 20 °C 8.1: Oxone / N,N-dimethyl-formamide / 16 h / 20 °C 9.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6: triethylamine / dichloromethane / 16 h / 20 °C 7: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C | ||
Multi-step reaction with 7 steps 1: acetic acid / ethanol / 16 h / 80 °C 2: sulfur; morpholine / ethanol / 16 h / 80 °C 3: 4-methylmorpholine N-oxide / dichloromethane / 3 h / 0 - 25 °C 4: methanol; tetrahydrofuran / 16 h / 20 °C 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16.33 h / 100 °C / Inert atmosphere 6: triethylamine / dichloromethane / 16 h / 20 °C 7: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With acetic acid In ethanol at 80℃; for 16h; | 23.2 To a stirring solution of 2-amino-4-bromobenzenethiol (4.3 g, 21.07 mmol) in EtOH (60 mL) was added malononitrile (2.8 g, 42.15 mmol) followed by AcOH (0.2 mL) and the resulting reaction mixture was stirred at 80 °C for 16 h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with water and concentrated under reduced pressure to dryness. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated to get a crude residue, which was purified by flash column chromatography eluting with 0-30% ethyl acetate in n-hexane to afford the title compound as a yellow solid (4.5 g, yield 85%). ‘H NMR (400 MHz, DMSO-d6) = 8.28 (s, 1H), 8.12 (d, J=8.58 Hz, 1H), 7.65 (d, J=8.58 Hz, 1H), 4.78 (s, 2H). LCMS: [M+Hj = 254.85; R = 3.02 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 2-amino-4-bromobenzenethiol; (2E)-3-phenyl-1-(1H-pyrazol-1-yl)prop-2-en-1-one With C32H30F6N4O3 In diethyl ether at 20℃; Inert atmosphere; Stage #2: With silica gel In toluene at 20℃; for 16h; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silica gel In toluene at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid / 18 h / Reflux 2: sodium hydroxide / water / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: acetic acid / 18 h / Reflux 2: sodium hydroxide; water / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | To a solution of2-amino-4-bromobenzenethiol (500 mg,2.50 mmol)in acetic acid (25mL)was added triphosgene (490 mg,1.70 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature,the solution was partially concentrated under reducedpressure,water was added,and the resulting precipitate was removed via filtration,and washedwith aqueous NaOH (1M). The filtrate was acidified with aqueous HCl (2 N)to pH 2,and placed in a refrigerator for 12 h. The resulting precipitate was filtered,washed with water,anddried under reduced pressure to give the title compound (133 mg,24%)as a while powder thatrequired no further purification. 1H NMR (400 MHz,DMSO-d6)8 10.97 (s,1H),7.33 (d,J = 1.9Hz,1H),7.13 (dd,J = 8.2,1.9 Hz,1H),6.91 (d,J = 8.2 Hz,1H),3.26 (s,3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide In ethanol at 20℃; for 4h; Inert atmosphere; | 1 Step 1: 4-Bromo-2-((3-nitropyridin-2-yl)thio)aniline To a stirred solution of 4-bromo-2 amino-benzenethiol (2.0 g, 9.8 mmol) and 2-chloro3-nitro- pyridine (2.0 g, 12.7 mmol) in ethanol was added sodium hydroxide (1.2 g, 29.4 mmol) at r.t. and stirring continuedat r.t for 4 h. Reaction mixture was filtered, solid waswashed with DMwater, and dried completly to offered the desired product as yellow solid (1.3 g, 42%):NIVIR (DMSO-d6,400 MHz) ö 5.55 (s, 2H), 6.68 (d, J 8.8 Hz, 1H) 7.27 (d, J 1.6 Hz, 1H), 7.29-7.42 (m, 2H), 8.59 (d, J= 8.0 Hz, 2H);MS (ESI) m/z 326 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In isopropyl alcohol; at 80℃; for 0.25h;Microwave irradiation; | General procedure: A mixture of o-phenylenediamine (1.0 mmol) and EDC.HCl (1.1 mmol) in 2-propanol (10 mL) was irradiated in microwave apparatus at 200 W (80 C) for 15 min. The reaction was monitored by TLC (eluent CH2Cl2 / MeOH 95:5). After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 25 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure and the obtained crude product was purified by flash column chromatography using silica gel (100-200 mesh) with 1-5% MeOH/CH2Cl2 as eluent. The fractions containing product were collected and concentrated under reduced pressure to afford N-ethyl-1Hbenzo[d]imidazol-2-amine (1a, 90% yield) as an off white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium nitrite In water at 200℃; for 0.166667h; | 5-6 Example 5 Synthesis of 5-bromobenzothiadiazole 100g of 2-mercapto-5-bromoaniline and 43g of sodium nitrite aqueous solution (74wt%) were pumped to the preheating pipeline for preheating, preheated to a temperature of 200 and then sent to the continuous flow reactor, the reaction pressure through the back pressure The valve was controlled at 4 MPa, and the reaction was kept for 10 minutes. The resulting reaction liquid was allowed to stand for layering. The organic layer was collected and washed with saturated sodium chloride solution to obtain a brown-yellow liquid as the product 5-bromobenzothiadiazole, yield 94 %, purity 99.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridine In dichloromethane at 20℃; | 4 Example 4 Dissolve 2-amino-4bromo-benzenethiol A-3 (20.3g, 100.0mmol) in 250mL of dichloromethane and add 2.2 equivalents of pyridine (17.38g) to the system while stirring at room temperature. Add 1.3 equivalents of TsCl (24.79g, 130mmol), continue to stir at room temperature until the substrate is completely reacted. After the substrate reaction is completed, a saturated copper sulfate solution is added to the system to wash the pyridine, and the pyridine is extracted to obtain the product Ts protected 2-aminobenzenethiol B-2 with a yield of 97% (34.63 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.54% | at 80℃; for 17h; | 6KKK.1 Step 1: The Synthesis of 5-Bromo-2-(trifluoromethyl)-1,3-benzothiazole 2-Amino-4-bromo-benzenethiol (9.5 g, 46.55 mmol) was added in one portion to a stirred solution of Trifluoroacetic acid (70 g, 613.93 mmol, 47.30 mL) at 80 °C. The resulting mixture was stirred at 80 °C for 17 hr, and then evaporated in vacuo. The residue was diluted with water (200 mL) and extracted with EtOAc (2*90 mL). The combined organic extracts were dried over sodium sulphate and evaporated in vacuo to afford 5-bromo-2-(trifluoromethyl)-1,3- benzothiazole (9 g, 31.91 mmol, 68.54% yield). 1H NMR (400 MHz, CDCl3) δ 7.66 (d, 1H), 7.84 (d, 1H), 8.35 (s, 1H). |
68.54% | at 80℃; for 17h; | 6KKK.1 Step 1: The Synthesis of 5-Bromo-2-(trifluoromethyl)-1,3-benzothiazole 2-Amino-4-bromo-benzenethiol (9.5 g, 46.55 mmol) was added in one portion to a stirred solution of Trifluoroacetic acid (70 g, 613.93 mmol, 47.30 mL) at 80 °C. The resulting mixture was stirred at 80 °C for 17 hr, and then evaporated in vacuo. The residue was diluted with water (200 mL) and extracted with EtOAc (2*90 mL). The combined organic extracts were dried over sodium sulphate and evaporated in vacuo to afford 5-bromo-2-(trifluoromethyl)-1,3- benzothiazole (9 g, 31.91 mmol, 68.54% yield). 1H NMR (400 MHz, CDCl3) δ 7.66 (d, 1H), 7.84 (d, 1H), 8.35 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.05% | In tetrahydrofuran at 25 - 50℃; for 2h; Inert atmosphere; | 6MMM.1 Step 1: Synthesis of 5-bromobenzo[d]thiazol-2(3H)-one 2-Amino-4-bromo-benzenethiol (30 g, 147.00 mmol) was dissolved in dry THF (500 mL) under argon. To the above solution di(imidazol-1-yl)methanone (26.5 g, 163.43 mmol) was added in one portion under argon and the reaction mixture was stirred under argon at 25°C for 1 hr (slightly exothermic reaction observed). Then the reaction mixture was stirred at 50°C for 1 hr (after the exothermic reaction passed), and then cooled down and concentrated in vacuum. The residue was diluted with water (300 ml), the precipitate was filtered, washed with water (3*50 ml) and dried in vacuum to afford 5-bromo-3H-1,3-benzothiazol-2-one (33.5 g, 145.60 mmol, 99.05% yield) as white solid. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 7.23 (s, 1H), 7.31 (d, 1H), 7.55 (s, 1H), 12.05 (bds, 1H). LCMS(ESI): [M]+ m/z: calcd 230.2; found 231.2; Rt = 1.083 min |
99.05% | In tetrahydrofuran at 25 - 50℃; for 2h; Inert atmosphere; | 6MMM.1 Step 1: Synthesis of 5-bromobenzo[d]thiazol-2(3H)-one 2-Amino-4-bromo-benzenethiol (30 g, 147.00 mmol) was dissolved in dry THF (500 mL) under argon. To the above solution di(imidazol-1-yl)methanone (26.5 g, 163.43 mmol) was added in one portion under argon and the reaction mixture was stirred under argon at 25°C for 1 hr (slightly exothermic reaction observed). Then the reaction mixture was stirred at 50°C for 1 hr (after the exothermic reaction passed), and then cooled down and concentrated in vacuum. The residue was diluted with water (300 ml), the precipitate was filtered, washed with water (3*50 ml) and dried in vacuum to afford 5-bromo-3H-1,3-benzothiazol-2-one (33.5 g, 145.60 mmol, 99.05% yield) as white solid. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 7.23 (s, 1H), 7.31 (d, 1H), 7.55 (s, 1H), 12.05 (bds, 1H). LCMS(ESI): [M]+ m/z: calcd 230.2; found 231.2; Rt = 1.083 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.88% | With phosphorous pentoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 25 - 50 °C / Inert atmosphere 2: trichlorophosphate / 32 h / 110 °C 3: ammonium hydroxide / 1,4-dioxane / 40 h / 135 °C / Autoclave 4: dmap / tetrahydrofuran / 3 h / 25 °C 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate / 1,4-dioxane / 48 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.18% | With toluene-4-sulfonic acid at 100℃; for 6h; | 6T.1 Step 1: Synthesis of 5-bromo-2-methylbenzo[d]thiazole 2-Amino-4-bromo-benzenethiol (19 g, 93.10 mmol) and 4-methylbenzenesulfonic acid; hydrate (106.25 mg, 558.58 μmol, 85.69 μL) were dissolved in trimethyl orthoacetate (38.03 g, 316.53 mmol, 3.49 mL). The resulting solution was stirred at 100°C for an additional 6 hr. Then the mixture was concentrated directly to afford the desired product 5-bromo-2-methyl-1,3- benzothiazole (20 g, 87.68 mmol, 94.18% yield). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 2.79 (s, 3H), 7.55 (d, 1H), 8.00 (d, 1H), 8.11 (s, 1H). LCMS(ESI): [M]+ m/z: calcd 228.2; found 229.2; Rt = 1.267 min |
94.18% | With toluene-4-sulfonic acid at 100℃; for 6h; | 6T.1 Step 1: Synthesis of 5-bromo-2-methylbenzo[d]thiazole 2-Amino-4-bromo-benzenethiol (19 g, 93.10 mmol) and 4-methylbenzenesulfonic acid; hydrate (106.25 mg, 558.58 μmol, 85.69 μL) were dissolved in trimethyl orthoacetate (38.03 g, 316.53 mmol, 3.49 mL). The resulting solution was stirred at 100°C for an additional 6 hr. Then the mixture was concentrated directly to afford the desired product 5-bromo-2-methyl-1,3- benzothiazole (20 g, 87.68 mmol, 94.18% yield). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 2.79 (s, 3H), 7.55 (d, 1H), 8.00 (d, 1H), 8.11 (s, 1H). LCMS(ESI): [M]+ m/z: calcd 228.2; found 229.2; Rt = 1.267 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di(p-tolyl) disulfide In N,N-dimethyl acetamide; lithium hydroxide monohydrate; dimethyl sulfoxide at 25℃; for 4h; Irradiation; |
Tags: 93933-49-4 synthesis path| 93933-49-4 SDS| 93933-49-4 COA| 93933-49-4 purity| 93933-49-4 application| 93933-49-4 NMR| 93933-49-4 COA| 93933-49-4 structure
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H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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