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CAS No. : | 117482-84-5 | MDL No. : | MFCD00015431 |
Formula : | C7H3ClFN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAHXXQJJZKBZDX-UHFFFAOYSA-N |
M.W : | 155.56 | Pubchem ID : | 145525 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.12 |
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) : | -5.5 cm/s |
Log Po/w (iLOGP) : | 1.77 |
Log Po/w (XLOGP3) : | 2.46 |
Log Po/w (WLOGP) : | 2.77 |
Log Po/w (MLOGP) : | 2.48 |
Log Po/w (SILICOS-IT) : | 2.86 |
Consensus Log Po/w : | 2.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.8 |
Solubility : | 0.248 mg/ml ; 0.00159 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.6 |
Solubility : | 0.388 mg/ml ; 0.00249 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.36 |
Solubility : | 0.0673 mg/ml ; 0.000433 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium fluoride In water; dimethyl sulfoxide | Example 2 Inventive Preparation of 3-chloro-4-fluorobenzonitrile 172 g of 3,4-dichlorobenzonitrile, 200 g of dimethylsulfoxide, 69.6 g of potassium fluoride, and 3.95 g of (N,N-dimethylimidazolidino)tris-(diethylamino)phosphazenium chloride were placed in a 1 liter four-neck flask equipped with anchor stirrer, thermometer, and reflux condenser with bubble counter. The mixture was then heated with stirring to 170° C. and this temperature was maintained for 6 hours. The mixture was then cooled to room temperature, water was added to the reaction mixture in a volumetric ratio of 1:1, and the 3-chloro-4-fluorobenzonitrile that precipitated was isolated by filtration, washing, and drying. 3-Chloro-4-fluorobenzo-nitrile was obtained in a yield of 92percent of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
204 g | With potassium fluoride; In cyclohexane; water; at 180℃; for 5h;Industrial scale; | In a 2000ml reactor with a stirrer, reflux manifold, thermometer was added 300g3,4_ dichlorobenzonitrile, 920g Example 4 rectification mother liquor (catalyst, a small amount of intermediate), 120g of cyclohexane, Warmed to 120 C, reflux separation.After the water separator to be anhydrous split into 300g spray-dried potassium fluoride, bis - (N- (dimethylamino) methylene) - chloride imide salt 5g, warmed to 130 C, reflux Water reaction 3h, to give the intermediate <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong>, continue to heat up to 180 C, the reaction 5h end.The reaction solution was filtered to remove salts, the filter cake was washed three times with toluene, the filtrate was vacuum-distilled,In the vacuum control 0.08 ~ 0.09MPa,The top of the tower collected 90-105 C of the fraction 204g, GC purity 99.3%, yield 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium fluoride; In cyclohexane; water; at 130℃; for 3h; | In a 2000ml reactor with a stirrer, reflux manifold, thermometer was added 300g3,4_ dichlorobenzonitrile, 920g Example 4 rectification mother liquor (catalyst, a small amount of intermediate), 120g of cyclohexane, Warmed to 120 C, reflux separation.After the water separator to be anhydrous split into 300g spray-dried potassium fluoride, bis - (N- (dimethylamino) methylene) - chloride imide salt 5g, warmed to 130 C, reflux Water reaction 3h, to give the intermediate 3-chloro-4-fluorobenzonitrile, continue to heat up to 180 C, the reaction 5h end.The reaction solution was filtered to remove salts, the filter cake was washed three times with toluene, the filtrate was vacuum-distilled,In the vacuum control 0.08 ~ 0.09MPa,The top of the tower collected 90-105 C of the fraction 204g, GC purity 99.3%, yield 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With caesium carbonate; In N,N-dimethyl-formamide; at 65℃; | EXAMPLE 772-(2-Chloro-4-cvanophenylaminoV5,5-dimethyl-8-oxo-5.6,7,8-tetrahydro-4if-thieno[2,3- clazepine-S-carboxylic acid ethyl ester; Intermediate 6 (1 g, 3.55 mmol), <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (0.55 g, 3.55 mmol) and cesium carbonate (1.15 g, 3.55 mmol) in DMF (10 mL) were stirred at 650C overnight, then partitioned between DCM (200 mL) and water (200 mL). The organic <n="83"/>phase was separated, dried over sodium sulphate and concentrated. After azeotroping with heptane to remove residual DMF the product was subjected to column chromatography (SiO2; DCM/ethyl acetate) to yield the title compound (800 mg, 54%). deltaH (DMSOd6) 10.98 (IH, s), 8.17 (IH, d, J 1.9 Hz), 8.13 (IH, t, J5.0 Hz), 7.90 (IH, dd, J 8.6, 1.9 Hz), 7.80 (IH, d, J 8.6 Hz), 4.33 (2H, q, J 7.1 Hz), 2.93 (2H, s), 2.87 (2H, d, J 5.1 Hz), 1.32 (3H, t, J 7.1 Hz), 1.00 (6H, s). LCMS (ES+) RT 3.31 minutes, 418/420 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Anhydrous p-toluene sulfonic acid (10 g, 52.57 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (3.88 g, 21.44 mmol) obtained in step 1 of Preparation Example 1 and <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (5.0 g, 32.14 mol) were added thereto and stirred at 160 C for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (3.24 g, 9.62 mmol) in a yield of 45 %. 1H NMR (CDCl3): delta 7.96-7.95 (1H, m), 7.76-7.73 (2H, m), 7.60 (1H, bs), 7.17-7.11 (1H, m), 6.93 (1H, d), 3.85 (3H, s), 3.84 (3H, d) MW: 336 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In dimethyl sulfoxide; at 60℃; for 2h; | 4.00 g (25.7 mmol) <strong>[117482-84-5]3-chloro-4-fluoro-benzonitrile</strong> are heated to 60 C. in 20 ml DMSO with 8.00 g (106.5 mmol) 2-amino-1-propanol with stirring for 2 hours. Then the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac. Yield: 5.20 g (96%) C10H11ClN2O (210.66) Mass spectrum: (M+H)+=211/213 (chlorine isotope) Rf value: 0.27 (silica gel; dichloromethane/methanol=19:1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 4-methyl-morpholine; In DMF (N,N-dimethyl-formamide); at 20 - 105℃; for 3.83333h; | 3.49 g (20 mmol) 3-Boc-amino-propylamine in 5 ml DMF are combined with 2.75 ml (25 mmol) NMM. After the addition of 3.11 g (20 mmol) <strong>[117482-84-5]3-chloro-4-fluoro-benzonitrile</strong> the mixture is stirred for 3.5 hours at ambient temperature under a nitrogen atmosphere, heated to 105 C. for 20 minutes and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over magnesium sulphate and evaporated down i. vac. The residue is further reacted without any more purification. Yield: 5.50 g (89%) C15H20N3O2 (309.80) Mass spectrum: (M+H)+=310/312 (chlorine isotope) Rf value: 0.40 (silica gel; petroleum ether/ethyl acetate=2:1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydride; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.5h; | 0.75 g (4.82 mmol) <strong>[117482-84-5]3-chloro-4-fluoro-benzonitrile</strong> together with 0.65 ml (0.58 g, 5.06 mmol) 3-dimethylamino-pyrrolidine in 12 ml DMF are combined with 231 mg (5.30 mmol) 55% sodium hydride dispersion at ambient temperature with stirring and under an argon atmosphere. After stirring at ambient temperature for 3.5 h the reaction mixture is poured into water and extracted with ethyl acetate after thorough mixing. The combined organic phases are washed with sat. sodium chloride solution, dried over magnesium sulphate and evaporated down completely i. vac. Yield: 1.11 g (92%) C13H16ClN3 (249.74) Mass spectrum: (M+H)+=250/252 (chlorine isotope) Rf value: 0.42 (silica gel; petroleum ether/ethyl acetate=1:1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 90℃; for 60h; | 5.90 g (37.9 mmol) <strong>[117482-84-5]3-chloro-4-fluoro-benzonitrile</strong> are dissolved in 65 ml DMF under a nitrogen atmosphere and combined with 5.45 g (39.5 mmol) potassium carbonate and 4.2 ml (3.5 g, 39.5 mmol) 2-methyl-pyrrolidine. After stirring for 2.5 days at 90 C. the reaction mixture is poured into 400 ml of water and extracted with ethyl acetate. The combined organic phases are washed several times with dilute and sat. sodium chloride solution, dried over magnesium sulphate and evaporated down i. vac. The residue remaining is further reacted without any more purification. Yield: 7.90 g (94%) Rf value: 0.40 (silica gel; petroleum ether/ethyl acetate=9:1+0.5% ammonia solution) C12H13ClN2 (220.70) Mass spectrum: (M+H)+=221/223 (chlorine isotope) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 100℃; | A solution of <strong>[117482-84-5]3-chloro-4-fluoro-benzonitrile</strong> (236 mg, 1.52 mmoles), piperazine (784 mg, 9.1 mmoles) and potassium carbonate (276 mg, 2 mmoles) in acetonitrile (5 mL) was heated to 100 C. overnight. The mixture was cooled, filtered and the filtrate concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-5% 2N methanolic ammonia in DCM) to provide the title compound. MS(APCI+) m/z 222 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 110℃; for 1h; | A 1 L flask was charged with the product E obtained above (27.2 g 122.3 mmol, 1.0 equiv), 23.13 g <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (122.3 mmol, 1.0 equiv), 49.8 g cesium carbonate (152.9 mmol, 1.25 equiv) and 200 mL DMF. The flask was equipped with a reflux condenser, and then placed into a preheated 110 C bath with stirring for 1 h under a dry N2 atmosphere. The resulting suspension was then cooled, diluted with H20 and extracted with 50% EtOAc/ Et20. The organics were washed with brine, dried with Na2S04 and concentrated under reduced pressure. Purification of the residue by flash chromatography (Si02, 20% EtOAc/Hexane) provided 33 g of the product as a white solid (90.4 mmol). 'H NMR (500 MHz, CDC13): 8 1.86 (s, 3H), 2.82 (s, 1H), 6.80 (J= 8.5 Hz, 1H), 7.33 (dd, J = 8.5,1.5 Hz, 1 H), 7.59 (d, J= 8.5 Hz, 2H), 7.64 (s, 1H), 7.73 (d, J= 8.5 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl acetamide; at 130℃; for 0.5h; | INTERMEDIATE 2 (263 mg, 1.0 mmol) was combined with <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (178 mg, 1.1 mmol) and Cs2CO3 (3.26 g, 10 mmol) in 10 mL of N,N-dimethylacetamide. The reaction mixture was stirred at 130 0C for 30 min, then was dumped into water and acidified with 2N aq. HCl to pH <2. The resulting solid precipitate was extracted with ethyl acetate and washed with water followed by brine, dried over anhydrous Na2SO4, filtered, and concentrated. Purification by Combi-Flash (silica, 5-30% ethyl acetate/hexane gradient) gave the product. LC-MS calc. for C20H15C1N2O3S: 398; Found: 399 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl acetamide; at 130℃; for 0.5h; | INTERMEDIATE 1 (125 mg, 0.50 mmol) was combined with <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (102 mg, 0.6 mmol) and Cs2CO3 (1.65 g, 5 mmol) in 5 mL of N,N-dimethylacetamide. The reaction mixture was stirred at 130 0C for 30 min, then was dumped into water and acidified with 2N aq. HCl to pH <2. The resulting solid precipitate was extracted with ethyl acetate and washed with water followed by brine, dried over anhydrous Na2SO4, filtered, and concentrated. Purification by Combi-Flash (silica, 5-30% ethyl acetate/hexane gradient) gave the product. LC-MS calc. for C19H13C1N2O3S: 384; Found: 385 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | EXAMPLE 7 5-(3Aminopropylamino)-7(3-chloro-4diethylaminophenyl)-[1,6]naphthyridine A sealed tube with <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (0.366 g, 2.4 mmol) and diethylamine (0.6 mL, 5.8 mmol) was heated to 100 C. for 8 hours. The reaction was allowed to cool to room temperature and water (5 mL) was added. The solution was extracted with dichloromethane (2*5 mL), dried over magnesium sulfate and concentrated in vacuo to afford 3-chloro-4-diethylaminobenzonitrile as an oil (0.38 g). This was reacted as described in Methods A-C (Examples 1-3) to provide the title compound. 1H NMR (CDCl3, 400 MHz) delta8.89 (dd, 1H), 8.26 (d, 1H), 8.11 (ddd, 1H), 7.97 (dd, 2.2 Hz, 1H), 7.53 (d, 1H), 7.27 (dd, 1H), 7.15 (d, 1H), 3.86 (b, 2H), 3.20 (q, 4H), 3.03 (t, 2H), 1.91 (quint, 2H), 1.08 (t, 6H); MS (m/e) calculated for C21 H26ClN5 383, found 384.3 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 37 3-Chloro-4-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-ylmethoxy)-benzonitrile The title compound was produced in accordance with the general method of example 6 from (2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-methanol (example 2) and <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong>. Light yellow solid, ISP-MS: m/e=378.3 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With oxygen; copper(II) trifluoroacetate; In dimethyl sulfoxide; at 110℃; for 24.5h;Sealed tube; Green chemistry; | General procedure: phenylacetic acid or its derivative (0.5mmol), Cu(TFA)2(20mmol%), urea (1.5 mmol) was added to the pressure sealed tube containing (0.75mL) of DMSO, after filling oxygen at 130 stirred for about 20h, the process by TLC and GC tracking (specifically the reaction time is determined by GC and TLC tracking results). After the raw material was observed by the GC and TLC the reaction has been completed the reaction, the reaction was removed, cooled to room temperature.To the reaction was added 20mL of ethyl acetate, washed with NaHCO3(20mL × 2), washed with saturated brine 20mL.The combined aqueous phases with ethyl acetate (20mL × 2) after stripping the combined organic phases with anhydrous sodium sulfate. The organic phase was dried by rotary evaporator spin solvent, product was purified by silica gel column, eluent ratio of ethyl acetate: petroleum ether = 50: 1. Benzonitrile obtained in a yield of 84%. |
81% | Comparative Example 3 Preparation of 3-chloro-4-fluorobenzonitrile According to the Prior Art The procedure was followed as in Example 2, but the catalyst was an equivalent molar amount of tetraphenylphosphonium bromide. 3-Chloro-4-fluorobenzonitrile was obtained in a yield of 81% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.3 g (95%) | With methylamine;P2O5; In tetrahydrofuran; water; | EXAMPLE 84B 3-chloro-4-(methylamino)benzonitrile A mixture of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65 C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) delta7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 3H). |
6.3 g (95%) | With methylamine;P2O5; In tetrahydrofuran; water; | EXAMPLE 84B 3-chloro-4-(methylamino)benzonitrile A mixture of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65 C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) delta 7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium fluoride; In water; dimethyl sulfoxide; | Example 2 Inventive Preparation of 3-chloro-4-fluorobenzonitrile 172 g of 3,4-dichlorobenzonitrile, 200 g of dimethylsulfoxide, 69.6 g of potassium fluoride, and 3.95 g of (N,N-dimethylimidazolidino)tris-(diethylamino)phosphazenium chloride were placed in a 1 liter four-neck flask equipped with anchor stirrer, thermometer, and reflux condenser with bubble counter. The mixture was then heated with stirring to 170 C. and this temperature was maintained for 6 hours. The mixture was then cooled to room temperature, water was added to the reaction mixture in a volumetric ratio of 1:1, and the 3-chloro-4-fluorobenzonitrile that precipitated was isolated by filtration, washing, and drying. 3-Chloro-4-fluorobenzo-nitrile was obtained in a yield of 92% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.54 g (81%) | With sodium chloride; In water; N,N-dimethyl-formamide; | Example 73 Synthesis of 2'-Chloro-4'-cyano-N-methoxy-p-toluenesulfonanilide (Compound No. 566) To a suspension of sodium hydride (60%, 0.09 g (2.25 mmol)) in DMF (3.0 ml), N-methoxy-p-toluenesulfonamide (0.45 g (2.20 mmol)) was added with stirring under cooling with ice. To the resulting mixture, after 15 minutes' stirring under cooling with ice, <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (0.31 g (1.99 mmol)) was added. The resulting mixture was then stirred under cooling with ice for one hour and at 50 C. for 18 hours. Water was added to the reaction mixture and extracted with diethyl ether. The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, to give 0.54 g (81%) of the title compound as white crystals. mp: 145.0-147.0 C.; NMR (CDCl3) delta: 2.49 (3H, s), 3.81 (3H, s), 6.82 (1H, d, J=8.3 Hz), 7.34 (2H, d, J=8.3 Hz), 7.39 (1H, dd, J=8.3 & 1.8 Hz), 7.63 (2H, d, J=8.3 Hz), 7.77 (1H, d, J=1.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; | (1) The title compound (904 mg) of Reference Example 10, diisopropylethylamine (1.57 mL) and <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (467 mg) were dissolved in N-methyl-2-pyrrolidone (9 mL), and the mixture was stirred at 80C for 8 hr. The reaction solution was added to saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 3-[(2S,4S)-1-tert-butoxycarbonyl-4-(2-chloro-4-cyanophenyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine (460 mg) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In tetrahydrofuran; at 50℃; | A mixture of 3-chloro-4-florobenzonitrile (312 mg, 2 mmol) and propylamine (236 mg, 4 mmol) in THF (4 mL) was heated at 50 C. overnight. After the solvent was removed, the residue was purified by flash chromatography with DCM to give 3-chloro-4-(propylamino)benzonitrile (365 mg, 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; | [1st Step: Synthesis of 3-[(3-chloro-4-cyanophenyl) thio]propionic acid] 5 g of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (32.1 mmol), 3.58 g of 3-mercaptopropionic acid (33.7 mmol), and 11.1 g of potassium carbonate (80.4 mmol) were put into 50 mL of DMF (dimethyl formamide) and reacted for 15 hours by maintaining the bath temperature at 100 C. After lowering the reaction temperature to room temperature, the reacted solution was slowly poured into 1500 mL of distilled water and th resulting precipitate was filtered off. The filtrate was acidified (pH up to 4 was confirmed by pH paper) with a 4 N HCl solution, thus producing organic material sediment. After filtering and washing the sediment with distilled water, the product was dried in a vacuum oven, and the structure was analyzed by the NMR (nuclear magnetic resonance) method. The yield was over 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 349A 4-(8-azabicyclo[3.2.1]oct-8-yl)-3-chlorobenzonitrile The title compound was prepared using the procedure described in Example 347A except using <strong>[117482-84-5]4-fluoro-3-chlorobenzonitrile</strong> instead of 4-fluoro-3-(trifluoromethyl)benzonitrile. | ||
Example 349A 4-(8-azabicyclo[3.2.1]oct-8-yl)-3-chlorobenzonitrile The title compound was prepared using the procedure described in Example 347A except using <strong>[117482-84-5]4-fluoro-3-chlorobenzonitrile</strong> instead of 4-fluoro-3-(trifluoromethyl)benzonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In tetrahydrofuran; at 5 - 20℃; for 2h; | To a solution of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (300 mg) and 1,1,1-trifluoro-2-propanol (263 mg) in THF (15 ml) was added 60% NaH (92.5 mg) at 5C, followed by stirring at room temperature for 2 hours, addition of a saturated NH4Cl solution to complete the reaction, and extraction with EtOAc. The obtained organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel chromatography (n-hexane:EtOAc=97:3 to 85:15) to obtain 3-chloro-4-(2,2,2-trifluoro-1-methylethoxy)benzonitrile (435 mg) as a colorless oily substance. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In dimethyl sulfoxide; at 80℃; for 24h; | To a solution of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (1.09g, 7.00mmol) in DMSO (25mL) was added 4-hydroxy-l-napthaldehyde (1.2Og, 7.0mmol) and caesium carbonate (4.55g, 14.0mmol). The reaction mixture was heated to 8O0C for 24h. After cooling to rt the mixture was partitioned between EtOAc (4OmL) and saturated NaHCO3 (5OmL), and the aqueous phase washed with EtOAc (5OmL). Solvent was removed in vacuo and the residue purified by column chromatography (EtOAcdsohexane, 2:8) to give the title compound: RT = 4.10min; m/z (ES+) = NO IONISATION [M + H]+. deltaH (DMSO) 7.10 (IH, t), 7.46 (IH, d), 7.78 (IH, t), 7.88 (IH, t), 7.94 (IH, d), 8.19 (IH, d), 8.32 (IH, d), 8.37 (IH, d), 9.28 (IH, d), 10.33 (IH, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 - 45℃; for 56h; | N,N-Diisopropylethylamine (4.37 mL, 25.1 mmol) was added to a solution of 2-fluoroethylamine hydrochloride (1.20 g, 12.0 mmol) and <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (1.56 g, 10.0 mmol) in DMSO (15 mL) at room temperature. The reaction mixture was stirred over weekend at room temperature and 8 h at 45 C., diluted with water (150 mL), and extracted with EtOAc (3*50 mL). The combined organic phases were washed with water (2*20 mL), saturated NaCl (2*20 mL) and dried with Na2SO4. The crude product was purified by MPLC on silica gel using Hex/EtOAc (4:1) to give 0.82 g (41%) of a white solid as the title compound. 1H NMR (400 MHz, CHLOROFORM-D) delta 3.50-3.64 (m, 2H), 4.57-4.77 (m, 2H), 5.13 (s broad, 1H), 6.67 (d, J=8.59 Hz, 1H), 7.44 (dd, J=8.59, 1.95 Hz, 1H), 7.55 (d, J=1.95 Hz, 1H); MS (ESI) (M+H)+: 199.15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 37 3-Chloro-4-(1-methyl-1-phenyl-ethoxy)-benzonitrile 2-Phenyl-2-propanol (0.191 g, 14.0 mmol) was dissolved in 10 mL DMF and cooled to 0 C. NaH (60% in oil, 0.062 g, 15.0 mmol) was added and the mixture stirred for 10 min. Then <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (0.200 g, 13.0 mmol) was added and the reaction stirred over a weekend. The reaction mixture was poured into 100 mL ice water and stirred vigorously. The solid precipitate was filtered off and suction dried to give 0.106 g off-white solid. (mp 60-62 C., LCMS=91% pure). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 18h; | To 1 mL of a 0.3M solution of the corresponding aryl fluoride in DMF (0.3 mmol) was added a 1 mL slurry of a 0.6 M solution of sodium hydride (60%) in DMF (0.6 mmol) and 0.33 mL of a 1 M solution of the corresponding alcohol (0.33 mmol) in THF. The resultant mixtures were shaken at room temperature over approximately 18 hours. The reactions were quenched with methanol and macroporous tosic acid resin (0.61 mmol, loading 4.07 mmol/g). The resultant mixture was shaken at room temperature for approximately 18 hours. Filtered the reaction, rinsing with methanol. The solvent was removed in vacuo using a Genevac HT-12 to obtain a sample that was then purified by reverse phase HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of NaH (1.25 eq) in DMF (100 ml) is added 1-butyl-piperidin-ol (15 g) obtained such as described under Preparation 3 step A, and stirred 1 h at AT, followed by the addition of <strong>[117482-84-5]3-chloro-4-fluoro-benzonitrile</strong> (1 eq) in DMF (100 ml) and continued stirring for a further 24 h at AT. The solvent is evaporated in vacuo, the residue redissolved in water, extracted with DCM, the organic layer is washed with an aqueous 1N NaOH solution then an aqueous NaCl solution, dried over MgSO4, filtered and evaporated. 20 g of desired product are isolated after chromatography on silica eluting with a DCM/MeOH/NH4OH mixture (97.5:2.5:0.1 v/v/v). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In methanol; at 120℃; for 0.25h;Microwave irradiation; | Example 21; 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-4-methylcarbamoyl-phenyl)-methyl-amide 111; A solution of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (1.0 g), methylamine (16 mL of a 2 M solution in methanol) and diisopropylethylamine was reacted in the microwave at 120 C. for 15 min. The mixture was then partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with brine (30 mL), dried (MgSO4) and reduced in vacuo to give 3-chloro-4-methylamino-benzonitrile. A suspension of 3-chloro-4-methylamino-benzonitrile (900 mg) in 2 M aqueous sodium hydroxide solution (30 mL) was heated at reflux for 3 h. After cooling to room temperature, the solution was acidified with 2 M aqueous hydrochloric acid and the resulting solid collected by filtration and air-dried to give 3-chloro-4-methylamino-benzoic acid. To a solution of 3-chloro-4-methylamino-benzoic acid (860 mg) in DMF (20 mL) was added carbonyl diimidazole (630 mg) and the reaction stirred at room temperature for 1 h. Then, methylamine hydrochloride (262 mg) and triethylamine (1.62 mL) were added and the reaction stirred at room temperature for 16 h. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with brine (3×40 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 3-chloro-N-methyl-4-methylamino-benzamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With caesium carbonate; In dimethyl sulfoxide; at 130℃; for 0.25h;Microwave irradiation; | Example 34; 3-Chloro-4-[6-(dicyclopropylmethyl-amino)-2,8-dimethyl-purin-9-yl]-benzonitrile; Dicyclopropylmethyl-(2,8-dimethyl-9H-purin-6-yl)-amine (0.03Og, 0.1 17mmol), 3-chloro-4- fluorobenzonitrile (0.022g , 0.140mmol) and Cs2CO3 (0.114g , 0.351 mmol) was dissolved in 1 ml of <n="49"/>anhydrous DMSO. The mixture was heated at 13O0C for 15 min in the microwave. The crude was partitioned between 10 ml of water and 2 x 10 ml of EtOAc. Combined organics were dried under MgSO4 and the solvent evaporated to yield a yellow solid which was purified by flash column chromatography in the ISCO with 12g of silica and a gradient of 0 to 50% EtOAc in heptane. Fractions bearing product were combined to yield the title product as a white solid (18mg, 39%):1H NMR (400MHz, CDCI3) delta = 0.37-0.59 (m, 8H), 1.0-1.10(m, 2H), 2.36 (s, 3H), 2.45 (s, 3H), 3.77(Br, 1 H), 5.69(br, 1 H), 7.52(d,1 H), 7.77(m, 1 H), 7.93(m, 1 H)LCMS (System 2): 1.45 mins m/z (APCI) = 393 [MH+], m/z (ES) = 393 [MH+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
~ 100% | Sodium Hydride (60% oil suspension, 28 mmol, 1.12 g) is triturated with hexane and suspended in N,N-dimethylformamide (18 mL). 1-(1H-Indol-3-yl)-2-methyl-propan-1-one (20 mmol, 2.34 g) is added to the ice-cooled suspension. After 5 minutes, 3-chloro, 4-fluorobenzonitrile (28 mmol, 4.37 g) is added. The reaction is stirred at 45 degrees Celsius for 90 minutes. The reaction mixture is allowed to cool and is extracted into ethyl acetate (400 mL) and is washed with water (200 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration, and silica gel chromatography to afford the desired 3-Chloro-4-indol-1-yl-benzonitrile as a white solid (5.78 g, quant) contaminated with some <strong>[117482-84-5]3-chloro,4-fluorobenzonitrile</strong>. The product is used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Sodium Hydride (60% oil suspension, 42 mmol, 1.68 g) is triturated with hexane and suspended in N,N-dimethylformamide (25 mL). 1,2,3,9-Tetrahydro-carbazole-4-one (21 mmol, 3.90 g) is added in several portions to the water-cooled suspension. After 5 minutes, <strong>[117482-84-5]3-chloro,4-fluorobenzonitrile</strong> (28 mmol, 4.35 g) is added, and the flask is lowered into a 50 degree Celsius oil bath. After 1 hour, the reaction mixture is allowed to cool and is extracted into ethyl acetate (1 L) and is washed with water (200 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration and silica gel chromatography (hexane:ethyl acetate 1:1) affords the desired 3-Chloro-4-(4-oxo-1,2,3,4-tetrahydro-carbazol-9-yl)benzonitrile as a solid (3.97 g, 59%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With hydroxylamine hydrochloride; triethylamine; In ethanol; at 50℃; for 13h; | To a solution of <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (500 mg, 3.0 mmol) in 10 ml ethanol was added hydroxylammonium chloride (335 mg, 5.0 mmol) and triethylamine (422 mg, 4.0 mmol) and then the reaction mixture was stirred 13 h at 50 C. After cooling to RT, the solvent was evaporated and the crude was solved in dichloromethane and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (451 mg, 74 % of theory). LC-MS (method 2B): RT = 1.73 min, m/z = 189 (M+H)+ |
With hydroxylamine hydrochloride; potassium carbonate; In ethanol;Reflux; | 3-Chloro-4-fluoro-N'-hydroxybenzimidamide To a solution of <strong>[117482-84-5]3-chloro-4-fluoro benzonitrile</strong> (1.0 g, 6.42 mmol) in ethanol (20 mL), was added hydroxylamine hydrochloride (0.665 g, 9.64 mmol), followed by addition of potassium carbonate (2.66 g, 19.28 mmol). The reaction mass was refluxed for 10-12 h. Excess of solvent was removed under vacuum and the reaction mass was diluted with water, acidified with dilute HCl and filtered to afford 0.400 g the desired product. 1HNMR (DMSO-d6): delta 5.95 (s, 2H), 7.42 (t, J=8.7 Hz, 1H), 7.69 (m, 1H), 7.83 (dd, 1H), 9.80 (s, 1H); MS [M+H]+: 189.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium carbonate; at 90℃; for 24h;Inert atmosphere; | Tert-Butyl piperazine-1-carboxylate (0.931 g, 5 mmol) and <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (0.785 g, 5.00 mmol) were combined, K2CO3 (0.898 g, 6.50 mmol) was added and the reaction mixture was stirred at 90 C. for 1d. The mixture was triturated with ethyl acetate (3*5 mL) and the combined organic extracts were filtered. This was concentrated down to about 5-10 mL and subjected to flash column chromatograhy on silica gel (120 g SiO2, hexanes:ethyl acetate 1:0 to 4:1) to afford tert-butyl 4-(2-chloro-4-cyanophenyl)piperazine-1-carboxylate (1.264 g, 3.93 mmol, 79% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 1.42 (s, 9H) 3.00-3.09 (m, 4H) 3.42-3.53 (m, 4H) 7.25 (d, J=8.59 Hz, 1H) 7.77 (dd, J=8.34, 2.02 Hz, 1H) 7.97 (d, J=2.02 Hz, 1H); [M+H] calc'd for C16H20ClN3O2, 322; found, 322. |
57% | With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h; | A mixture of compound (251) (1.00 g, 6.40 mmol), piperazine-l -carboxylic acid tert-butyl ester (1.43 g, 7.70 mmol) and Cs2C03 (2.45 g, 7.70 mmol) in DMF (10 mL) was stirred at 100 C for 3 h. After cooled to room temperature, the reaction mixture was diluted with EtOAc (80 mL). The mixture was washed with water (50 mL), brine (30 mL x3), dried over anhydrous Na2S04 and filtered. The filtrate was evaporated in vacuum to residue, which was purified by silica gel column chromatography (from PE to PE/EA = 10/1) to give compound (252) (1.2 g, yield: 57%) as white solid. [00645] lH NMR (400MHz, CDC13): delta = 7.64 (s, 1H), 7.51 (d, J= 8.4 Hz, 1H), 7.02 (d, J= 8.8 Hz, 1H), 3.61-3.60 (m, 4H), 3.14-3.06 (m, 4H), 1.48 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1: 3-Chloro-4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-benzonitrile In analogy to Example 156, step 1, 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one (Example 151, step 7) was reacted with <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> and cesium carbonate to give the title compound as a colorless solid. MS (m/e)=497.3 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1: 3-Chloro-4-{3-chloro-4-[2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-benzonitrile In analogy to Example 156, step 1, 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1H-pyridin-2-one (Example 203, step 5) was reacted with <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> and cesium carbonate to give the title compound as a colorless solid. MS (m/e)=511.2 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; at 80℃; for 12h;Sealed tubde; Neat (no solvent); | Step 1: 3-Chloro-4-(isopropylamino)benzonitrile (62). A reaction mixture of isopropylamine (50 mL), 61 (5.0 g, 32.15 mmol) and Et3N (5.4 mL, 38.57 mmol) was heated in a sealed tube at 80 C. The reaction mixture was then cooled and diluted with water. The aqueous layer was extracted with ethyl acetate. The organic layer was dried and concentrated to afford 62 (6.0 g) as a colorless oil which was used as such for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | To a stirring solution of (+/-)-pantolactone (2.8 g, 21.0 mmol, Aldrich) in DMF (39 mL) at 0 C. was added NaH (887 mg, 22.2 mmol, 60% dispersion in mineral oil) portion-wise under a nitrogen atmosphere. After gas evolution ceased, <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (3.0 g, 19.3 mmol, Aldrich) was added. The resulting mixture was allowed to warm to ambient temperature over 19 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and diluted with EtOAc ?ethylacetate?. The layers were separated and the organic layer washed with additional saturated aqueous NH4Cl followed by brine. The organics were dried (MgSO4), filtered, and concentrated in vacuo. The resulting white solid was purified by flash chromatography (5% to 50% EtOAc/hexanes) to afford 2.9 g (56%) of the desired aryl ether as a white solid. MS (AP-)=264.0; LCMS purity=100%, tR=2.307 (50% to 2% H2O+0.1% HCO2H/CH3CN+0.1% HCO2H, 4 min run time |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Sodium Hydride (60% oil suspension, 4 mmol, 0.160 mg) is triturated with hexane and suspended in N,N-dimethylformamide (3 mL). 3-Acetylindole (2 mmol, 318 mg) is added to the water-cooled suspension. After 5 minutes, <strong>[117482-84-5]3-chloro,4-fluorobenzonitrile</strong> (3 mmol, 368 mg) is added. The reaction is stirred at 50 degrees Celsius for 45 minutes. The reaction mixture is allowed to cool and is extracted into ethyl acetate (200 mL) and is washed with water (50 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration, and silica gel chromatography affords the desired 4-(3-Acetyl-indol-1-yl)-3-chloro-benzonitrile as a tan solid (309 mg, 52%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With lithium carbonate; In dimethyl sulfoxide; at 100℃; for 16h; | Reference Example 42 3-chloro-4-(4-formyl-2-methoxyphenoxy)benzonitrile; [Show Image] To a solution (15 mL) of 4-hydroxy-3-methoxybenzaldehyde (1.00 g) in dimethyl sulfoxide were added lithium carbonate (721 mg) and <strong>[117482-84-5]3-chloro-4-fluorobenzonitrile</strong> (1.21 g), and the mixture was stirred at 100C for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=100:0?70:30) to give the title compound as a colorless oil (yield: 1.48 g, 80%). 1H-NMR (DMSO-d6, 300 MHz):delta3.85 (3H, s), 6.92 (1H, d, J = 8.7 Hz), 7.35 (1H, d, J = 8.1 Hz), 7.63 (1H, dd, J = 8.1, 1.7 Hz), 7.70 (1H, d, J = 1.7 Hz), 7.76 (1H, dd, J = 8.7, 1.9 Hz), 8.22 (1H, d, J = 1.9 Hz), 10.00 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Preparation 303-Chloro-4-[(5-chloro-6-methoxypyridin-3-yl)methoxy1benzonitrileTo a solution of 5-chloro-3-hydroxymethyl-6-methoxypyridine (50 mg, 0.29 mmol) in DMF (3 ml_) was added sodium hydride dispersion in oil (60%, 13.8 mg, 0.576 mmol) and the reaction stirred at 0C for 30 minutes. 3-Chloro-4-fluorobenzonitrile (45 mg, 0.288 mmol) was then added and the reaction stirred, warming to room temperature for 2 hours. The reaction was poured onto water (10 ml_) and extracted with EtOAc (10 ml_), dried over sodium sulfate and concentrated in vacuo to afford the title compound (89 mg, 72%).LCMS Rt = 1 .75 minutes MS m/z 309[MH]+1H NMR (de-DMSO): delta 3.95 (s, 3H), 4.25 (s, 2H), 7.45 (d, 1 H), 7.85 (m, 1 H), 8.05 (m, 2H), 8.25 (s, 1 H). |
Tags: 117482-84-5 synthesis path| 117482-84-5 SDS| 117482-84-5 COA| 117482-84-5 purity| 117482-84-5 application| 117482-84-5 NMR| 117482-84-5 COA| 117482-84-5 structure
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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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