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CAS No. : | 1813-33-8 | MDL No. : | MFCD00084939 |
Formula : | C8H3ClF3N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GEHMLBFNZKJDQM-UHFFFAOYSA-N |
M.W : | 205.56 | Pubchem ID : | 2736476 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.17 |
TPSA : | 23.79 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) : | -5.32 cm/s |
Log Po/w (iLOGP) : | 1.97 |
Log Po/w (XLOGP3) : | 3.15 |
Log Po/w (WLOGP) : | 4.38 |
Log Po/w (MLOGP) : | 3.08 |
Log Po/w (SILICOS-IT) : | 3.46 |
Consensus Log Po/w : | 3.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.37 |
Solubility : | 0.0868 mg/ml ; 0.000422 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.32 |
Solubility : | 0.0985 mg/ml ; 0.000479 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.99 |
Solubility : | 0.0209 mg/ml ; 0.000102 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.8% | Stage #1: With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere Stage #2: With acetic acid In water; toluene at 0℃; for 2 h; |
2-Chloro-4-(trifluoromethyl)benzonitrile (500 mg, 2.43 mmol) was diluted with toluene (3 mL), placed under nitrogen and cooled to -78°C. DIBAL-H (4865 μL, 4.86 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 00C and acetic acid (2 mL) was added followed by 10 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle's salt, dried over MgSO4, filtered and concentrated. The material was purified using a biotage 25 cartridge running a gradient, 100percenthexanes to 20percentDCM/hexanes to yield 2-chloro-4-(trifluoromethyl)benzaldehyde (400 mg, 1.92 mmol, 78.8 percent yield) as a clear oil. |
30% | Stage #1: With diisobutylaluminium hydride In toluene for 0.5 h; Cooling with ethanol-dry ice Stage #2: With acetic acid In water; toluene at 20℃; for 2 h; |
Dissolve 2-chloro-4-trifluoromethylbenzonitrile (405 mg, 1.97 mmol) in anhydrous toluene (7 mL) and cool in a dry ice/ethanol bath. Add diisobutylaluminum EPO <DP n="62"/>hydride (DIBAL) (3.94 niL, 3.94 mmol, 1.0 M in toluene) slowly. Stir 30 min. Warm to room temperature, add acetic acid (2 mL) and water (10 rnL) and stir for 2 hours. Extract the aqueous layer with ethyl acetate twice. Wash the organic layer with potassium sodium tartrate solution (Rochelle salt) twice. Dry (magnesium sulfate), filter, and concentrate to give a residue. Chromatograph the residue on silica gel eluting with a gradient of 100:0 to 1:1 hexanes:dichloromethane to give 2-chloro-4- trifluoromethylbenzaldehyde (123 mg, 30percent). 1H NMR (400 MHz, CDCl3) δ 10.52 (s, IH), 8.05 (d, IH5 J = 8.0 Hz), 7.75 (s, IH), 7.66 (d, IH, J = 8.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; DavePhos; at 65℃; for 2h; | Example IA. 2-(3.3 -dimethylbut-1-ynyl)-4-(trifluoromethyl)benzonitrile .Pd2dba3:CHCl3 (0.439 g, 0.424 mmol, 1.5%), dicyclohexylphosrhohino-2'-(N,N- dimethylamino)biphenyl (0.640 g, 1.63 mmol, 6%), and CuI (0.155 g, 0.816 mmol, 3%) were placed in a flask and purged with N2. triethylamine (16 mL) was added and the mixture was stirred for 5 minutes followed by the addition of <strong>[1813-33-8]3-chloro-4-cyanobenzotrifluoride</strong> (4.00 mL, 27.0 mmol) and 3,3-dimethylbutyne (4.00 mmol, 1.2 eq). The mixture was heated under N2 at 65 0C for 2 hours, cooled to ambient temperature and diluted with ethyl acetate (~300 mL). The mixture was washed sequentially with ~2% aqueous NH4OH (120 mL) and saturated aqueous NH4CI (10OmL). The organic layer was dried (Na2SO4), filtered, concentrated, and filtered through SiO2 (~90 mL) with 4% diethyl ether/Hex to provide the title compound. 1H- NMR (CDCl3) delta 7.71-7.75 (m, 2H), 7.58 (dd, IH), 1.37 (s, 9H). | |
With copper(l) iodide; triethylamine;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; at 65℃; for 4h;Inert atmosphere; | To a flask was added Pd2dba3 (0.405 g), DavePhos (0.6884 g, 1.75 mmol), and CuI (0.1655 g). This was purged with nitrogen and degassed; triethylamine (100 mL) was then added. <n="43"/>Benzonitrile (XVII) (36.2 g, 176 mmol) was then added, and the mixture was heated to 65 0C. 3,3-dimethylbutyne (23.7 g, 288 mmol) was then slowly added over 2 hours. The mixture was heated an additional 2 hours, and the heat removed. The mixture was diluted with isopropyl acetate (150 mL) and washed twice with water (150 mL) and twice with 10% aqueous citric acid (150 mL). The organics were diluted with methanol (40 mL), and the volume reduced in vacuo to 60 mL. This was repeated twice with 190 mL methanol, the residual material diluted to 250 g with methanol and used in the next step as a solution. An analytical sample was obtained by removing all the solvent in vacuo.1H NMR (CDCl3, 400 mHz) 7.75 - 7.70 (m, 2H), 7.60-7.55 (m, IH), 1.37 (s, 9H); 13C NMR (CDCl3, 100MHz) 132.6, 128.7, 128.6, 123.8, 123.7, 116.24, 107.96, 75.06, 30.73, 28.64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2A. (2-isobutyl-4-(trifluoromethyl)phenyl)methanamine. A solution of 2-methylpropenylmagnesium bromide (0.5 M in THF, 6.0 mL, 3.0 mmol) was added to a solution of ZnCh (1 -0 M in diethyl ether, 3.0 mL, 3.0 mmol) at 00C. The mixture was stirred for 10 minutes cold, and an additional 30 min after removing the cooling bath. 2-chloro-4-trifluoromethyI-benzonitrile (0.35mL, 2.4 mmol) was added, followed by a solution containing Pd2dba3.CHCl3 (48.5 mg, 0.047 mmol) and 2- dicyclohexylphophino-2'-(N,N-dimethylamino)biphenyl (56.3 mg, 0.14 mmol) in THF (1 mL). The mixture was stirred at 60 0C for 3 hours, diluted with ethyl acetate and the resulting mixture washed sequentially with 0.1 N aqueous HCl (2x) and brine (Ix). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure, and purified by flash chromatography (5% diethyl ether/hexane) to provide 0.264 g of the nitrile as a clear oil which was used without further purification. The oil was dissolved in 4:1 methanol: ethyl acetate (25 mL), shaken in the presence of 10% Pd/C and Ra Ni (catalytic amounts) under H2 (60 psi) overnight. The mixture was filtered and concentrated under reduced pressure, and the residue purified by flash chromatography (20-100% ethyl acetate in dichloromethane as a gradient elution) to provide the title compound. 1H NMR (CDCl3) delta 7.43-7.52 (m, 2H), 7.37 (brs, IH), 3.94 (brs, 2H), 2.57 (d, 2H), 1.87 (m, IH), 1.49 (brs, 2H), 0.94 (d, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; toluene; for 18h;Heating / reflux; | Example 4A. 2-isopropyl-4-(trifluoromethyl)benzonitrile. To a solution of <strong>[1813-33-8]2-chloro-4-trifluoromethyl-benzonitril</strong>e (0.67mL, 4.5 mmol) and [1,1 '-bisfdiphenylphosphinojferroceneldichloropalladiumtll) (110 mg, 0.14 mmol) in 15 mL of dioxane was added Zn(iso-Propyl)2 (IN in toluene, 9 mmol). The mixture was heated to reflux for 18 hours, cooled to ambient temperature and diluted with methanol. The mixture was further diluted with ether and washed sequentially with IN HCl, water and brine. The organic layer was dried over Na2SO4, filtered, and then concentrated under reduced pressure. The crude product was purified by flash column chromatography (0% to 10% ethyl acetate/hexane) to provide the title compound. 1H NMR (CDCl3) delta 7.73 (d, IH), 7.63 (s, IH), 7.55 (d, IH), 3.45 (sept, IH), 1.36 (d, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 246A 2-chloro-4-(trifluoromethyl)benzylamine The title compound was prepared using the procedure described in Example 244A using <strong>[1813-33-8]2-chloro-4-(trifluoromethyl)benzonitrile</strong> instead of 4-bromo-3-methylbenzonitrile. MS (ESI+) m/z 209 (M+H)+; 1H NMR (DMSO, 300 MHz) delta 3.97 (s, 2H), 7.50-7.70 (m, 3H). | ||
Example 246A 2-chloro-4-(trifluoromethyl)benzylamine The title compound was prepared using the procedure described in Example 244A using <strong>[1813-33-8]2-chloro-4-(trifluoromethyl)benzonitrile</strong> instead of 4-bromo-3-methylbenzonitrile. MS (ESI+) m/z 209 (M+H)+; 1H NMR (DMSO, 300 MHz) delta 3.97 (s, 2H), 7.50-7.70 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In tetrahydrofuran; tetrahydrofuran, ethyl bromide; | EXAMPLE 17 1'-[4-[1-(4-Fluorophenyl)-5-trifluoromethylindazol-3-yl]-1-butyl]spiro]isobenzofuran-1(3H),4'-piperidine], 17a. To a suspension of magnesium turnings (135 g) in 300 ml of dry tetrahydrofuran, ethyl bromide (140 g) dissolved in 500 ml of dry tetrahydrofuran was slowly added followed by reflux for 20 min. A solution of 4-chloro-1-butanol (274 g) in 500 ml of tetrahydrofuran was added dropwise at reflux temperature. After stirring for 20 min, the Grignard solution was filtered and added portionwise to a solution of <strong>[1813-33-8]2-chloro-4-trifluoromethyl-benzonitril</strong> (200 g) in 600 ml of dry tetrahydrofuran. The reaction mixture was stirred for 16 h at room temperature followed by addition af 2N hydrochloric acid and ice. Extraction with ether, drying of the ether phase over magnesium sulfate and removal of solvent in vacuo left a viscous oil which was applied to a silica gel column (eluent:dichloromethane/ether=3:1) giving 4-(2-chloro-5-trifluoromethylbenzoyl)-1-butanol (101 g) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.8% | 2-Chloro-4-(trifluoromethyl)benzonitrile (500 mg, 2.43 mmol) was diluted with toluene (3 mL), placed under nitrogen and cooled to -78C. DIBAL-H (4865 muL, 4.86 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 00C and acetic acid (2 mL) was added followed by 10 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle's salt, dried over MgSO4, filtered and concentrated. The material was purified using a biotage 25 cartridge running a gradient, 100%hexanes to 20%DCM/hexanes to yield 2-chloro-4-(trifluoromethyl)benzaldehyde (400 mg, 1.92 mmol, 78.8 % yield) as a clear oil. | |
30% | Dissolve <strong>[1813-33-8]2-chloro-4-trifluoromethylbenzonitrile</strong> (405 mg, 1.97 mmol) in anhydrous toluene (7 mL) and cool in a dry ice/ethanol bath. Add diisobutylaluminum EPO <DP n="62"/>hydride (DIBAL) (3.94 niL, 3.94 mmol, 1.0 M in toluene) slowly. Stir 30 min. Warm to room temperature, add acetic acid (2 mL) and water (10 rnL) and stir for 2 hours. Extract the aqueous layer with ethyl acetate twice. Wash the organic layer with potassium sodium tartrate solution (Rochelle salt) twice. Dry (magnesium sulfate), filter, and concentrate to give a residue. Chromatograph the residue on silica gel eluting with a gradient of 100:0 to 1:1 hexanes:dichloromethane to give 2-chloro-4- trifluoromethylbenzaldehyde (123 mg, 30%). 1H NMR (400 MHz, CDCl3) delta 10.52 (s, IH), 8.05 (d, IH5 J = 8.0 Hz), 7.75 (s, IH), 7.66 (d, IH, J = 8.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | at 80℃; | To commercially available <strong>[1813-33-8]2-chloro-4-trifluoromethylbenzonitrile</strong> 13 (1 ml, 7.2 mmol) was added piperidine (4equiv., 2.8ml) and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 1 g of a yellow oil. Yield = 56% 'HNMR (DMSO, 200 MHz) delta 1.60 (6H, m), 3.20 (4H, m), 7.34 (2H, m), 7.89 (1H, dd, J = 8.6 Hz, J' = 0.4 Hz) |
56% | at 80℃; | Preparation of 4-(trifluoromethyl)-2-(piperidin-1-yl)benzonitrile 14c (scheme 7) To commercially available 2-chloro-4-benzonitrile (1 ml, 7.2 mmol) was added piperidine (4equiv., 2.8ml) and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 1 g of a yellow oil. Yield = 56% 1HNMR (DMSO, 200 MHz) delta 1.60 (6H, m), 3.20 (4H, m), 7.34 (2H, m), 7.89 (1H, dd, J = 8.6 Hz, J' = 0.4 Hz) |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 50℃; for 12h; | General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | at 80℃; | To commercially available <strong>[1813-33-8]2-chloro-4-trifluoromethylbenzonitrile</strong> 13 (4 ml, 29 mmol) morpholine (4equiv., 10 ml) was added and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 6.19 g of a yellow oil. Yield = 83% 'HNMR (DMSO, 200 MHz) delta 3.24 (4H, m), 3.75 (4H, m), 7.94 (1H, m), 8.23 (1H, m). |
83% | at 80℃; | Preparation of 4-(trifluoromethyl)-2-morpholinobenzonitrile 14d (scheme 7) To commercially available 2-chloro-4-benzonitrile (4 ml, 29 mmol) morpholine (4equiv., 10 ml) was added and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 6.19 g of a yellow oil. Yield = 83% 1HNMR (DMSO, 200 MHz) delta 3.24 (4H, m), 3.75 (4H, m), 7.94 (1H, m), 8.23 (1H, m). |
In N,N-dimethyl-formamide; at 120℃; for 6h; | General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol)were dissolved in DMF (8 ml). The mixture was stirred for 6 h at120 C. The reaction was quenched with water and extracted withEtOAc twice. The combined organic extracts were dried overMgSO4, filtered, and concentrated in vacuo. The residue was purifiedby flash column chromatography on silica gel using EtOAc/hexane (1:7) eluant condition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | at 80℃; | To commercially available <strong>[1813-33-8]2-chloro-4-trifluoromethylbenzonitrile</strong> 13 (lml, 7.2 mmol) pyrrolidine (4equiv., 2.38 ml) was added and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 940mg of a yellow solid. Yield = 54% 'HNMR (DMSO, 200 MHz) delta 1.95 (4H, m), 3.58 (4H, m), 6.94 (2H, m), 7.73 (1H, dd, J = 8 Hz, J'= 0.8 Hz). |
54% | at 80℃; | Preparation of 4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzonitrile 14b (scheme 8) To commercially available 2-chloro-4-benzonitrile (1ml, 7.2 mmol) pyrrolidine (4equiv., 2.38 ml) was added and the solution was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 940mg of a yellow solid. Yield = 54% 1HNMR (DMSO, 200 MHz) delta 1.95 (4H, m), 3.58 (4H, m), 6.94 (2H, m), 7.73 (1H, dd, J = 8 Hz, J' = 0.8 Hz) |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 50℃; for 12h; | General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | at 80℃;closed vessel; | To commercially available <strong>[1813-33-8]2-chloro-4-trifluoromethylbenzonitrile</strong> 13 (0.5 ml, 3.6 mmol) dimethylamine (4equiv., 0.95 ml) was added and the solution was heated in closed vessel at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 730 mg of a pale yellow oil. Yield = 94% 'HNMR (CDC13, 200 MHz) delta 3.13 (6H, s), 7.05 (1H, bs), 7.59 (1H, dd, J = 8.4 Hz, J' = 0.6 Hz), 7.99 (1H, bs) |
94% | In ethyl acetate; at 80℃;Sealed vessel; | Example 4: 1-(2-(dimethylamino)-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea (scheme 1) Preparation of 2-(dimethylamino)-4-(trifluoromethyl)benzonitrile 14a (scheme 7) To commercially available 2-chloro-4-benzonitrile (0.5 ml, 3.6 mmol) dimethylamine (4equiv., 0.95 ml) was added and the solution was heated in closed vessel at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 730 mg of a pale yellow oil. Yield = 94% 1HNMR (CDCI3, 200 MHz) delta 3.13 (6H, s), 7.05 (1H, bs), 7.59 (1H, dd, J = 8.4 Hz, J' = 0.6 Hz), 7.99 (1H, bs) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | To a suspension of NaH 60% (0.09g, 3.97 mmol) in DMF (20 mL) at 0C was added in one portion lH-imidazole (2.5 mol eq, 0.61g). After 10 min 2-chloro- 4-(trifluoromethyl)-benzonitrile (0.5 mL, 3.61 mmol) was added and the reaction mixture was heated at 100C for 2h. The reaction was cooled at room temperature, water was added and the aqueous solution was extracted with EtOAc (3x25 mL). The recombined organic phases were dried over sodium sulfate and evaporated to dryness to give the 2-imidazol-l-yl-4-(trifluoromethyl)benzonitrile as pale yellow oil (0.63g, 73% Yield) used for the reduction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 80℃; | To commercially available <strong>[1813-33-8]2-chloro-4-trifluoromethylbenzonitrile</strong> 13(lml, 7.2 mmol) in DMF 1 equiv. of NaH and 1 ,2,4-tetrazole (4equiv., 1.98 g) were added and the mixture was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 900mg of a yellow solid. Yield = 53% 'HNMR (DMSO, 200 MHz) delta 8.08 (1H, dd, J = 7.6 Hz, J' = 1 Hz), 8.33 (3H, m), 9.29 (1H, s). |
53% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 80℃; | Preparation of 4-(trifluoromethyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile 14e (scheme7) To commercially available 2-chloro-4-benzonitrile (1ml, 7.2 mmol) in DMF 1 equiv. of NaH and 1,2,4-tetrazole (4equiv., 1.98 g) were added and the mixture was heated at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 900mg of a yellow solid. Yield = 53% 1HNMR (DMSO, 200 MHz) delta 8.08 (1H, dd, J = 7.6 Hz, J' = 1 Hz), 8.33 (3H, m), 9.29 (1H, s). |
Tags: 1813-33-8 synthesis path| 1813-33-8 SDS| 1813-33-8 COA| 1813-33-8 purity| 1813-33-8 application| 1813-33-8 NMR| 1813-33-8 COA| 1813-33-8 structure
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Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
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. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
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: |
P309 | IF exposed or if you feel unwell: |
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. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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