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CAS No. : | 2924-16-5 | MDL No. : | MFCD00012934 |
Formula : | C6H8ClFN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SKVGLOFWEJFQKU-UHFFFAOYSA-N |
M.W : | 162.59 | Pubchem ID : | 2723914 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 39.46 |
TPSA : | 38.05 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.83 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.06 |
Log Po/w (WLOGP) : | -1.54 |
Log Po/w (MLOGP) : | 2.13 |
Log Po/w (SILICOS-IT) : | 0.79 |
Consensus Log Po/w : | 0.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.52 |
Solubility : | 0.487 mg/ml ; 0.00299 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.49 |
Solubility : | 0.529 mg/ml ; 0.00325 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.33 |
Solubility : | 0.766 mg/ml ; 0.00471 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
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 |
---|---|---|
99.2% | With hydrogenchloride In water at 65℃; | 4) salt [0026] A mixture of 22. lg 3-fluorophenylhydrazine was dissolved in 15.4 ml of 37percent hydrochloric acid and stirred at 65 ° C until the reaction solution was precipitated Crystallization, cooling to 20 ° C, filtration, with acetone leaching filter cake, after drying to be 3-fluorophenylhydrazine hydrochloride products 24. 4g, content 99. 2percent yield of 39. 1percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Table 1 shows some examples that are encompassed by the general formula (I) and in Table 2 the data are indicated for identification of these compounds. The examples 1-36, 44-63 and 65-74 have been prepared according to method A, examples 37-39 according to method B, examples 40-42 according to method C, example 64 according to method F and the enantiomerically pure compounds 75-78 by resolution of the racemic mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol; at 70℃; for 6h;Heating / reflux; | EXAMPLE 96 6H-[1,3]Thiazolo[5,4-e]indole-7,8dione 8-[N-(3-fluorophenyl)hydrazone](Z-isomer) 6H-1-Thia-3,6-diaza-as-indacen-7,8-dione (Procedure A, 50 mg, 0.25 mmol) was combined with <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> (50 mg, 0.3 mmol) in 2 ml of ethanol and heated at 70 C. for 6 hrs.. The product was collected by filtration of the hot solution, washing with ethanol and diethyl ether, to give 47 mg (60%) of the title compound as a brown solid. 1H NMR (DMSO-d6): delta 6.82 (t, J=8.7 Hz, 1H); 7.10 (d, J=8.6 Hz, 1H); 7.37 (m, 2H); 7.41 (dd, 1H); 7.97 (d, J=8.6 Hz, 1H); 9.25 (s, 1H); 11.2 (s, 1H). ES-MS m/z 311 (M-1)-. |
47 mg (60%) | In ethanol; | EXAMPLE 96 6H-[1,3]Thiazolo[5,4-e]indole-7,8-dione 8-[N-(3-fluorophenyl)hydrazone] (Z-isomer) 6H-1-Thia-3,6-diaza-as-indacen-7,8-dione (Procedure A, 50 mg, 0.25 mmol) was combined with <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> (50 mg, 0.3 mmol) in 2 ml of ethanol and heated at 70 C. for 6 hrs. The product was collected by filtration of the hot solution, washing with ethanol and diethyl ether, to give 47 mg (60%) of the title compound as a brown solid. 1H NMR (DMSO-d6): delta6.82 (t, J=8.7 Hz, 1H); 7.10 (d, J=8.6 Hz, 1H); 7.37 (m, 2H); 7.41 (dd, 1H); 7.97 (d, J=8.6 Hz, 1H); 9.25 (s, 1H); 11.2 (s, 1H). ES-MS m/z 311 (M-1)-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; ethyl acetate; | 1. Preparation of 1-(3-Fluorophenyl)-1,2,4-triazole A mixture of 1,3,5-triazine (1 g, 12.3 mmol) and <strong>[2924-16-5]3-Fluorophenylhydrazine hydrochloride</strong> (2 g, 12.3 mmol) in ethanol (20 mL) is heated at reflux overnight. After concentrating, ethyl acetate is added, the mixture is washed with aqueous bicarbonate followed by saturated aqueous sodium chloride, dried (MgSO4), and concentrated to give 1.8 g of crude 1-(3-Fluorophenyl)-1,2,4-triazole. 1H NMR (CDCl3): delta 8.57 (s, 1H), 8.12 (s, 1H), 7.46-7.51 (m, 3H), 7.08-7.15 (m, 1H). LCMS 164.1 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | 2D-a) 3- fluorophenylhydrazine hydrochloride This intermediate was prepared by diazotisation of commercially available 3-Fluoroaniline. The Hydrazine hydrochloride was recrystallized from water to give a light brown powder in 70% yield M.pt: 237 deg C decomposes IR (KBr) cm-1 3448 and 3199(NH), 1581 (NH), 1496 (C=C), 675(C-CI), 1151,1263 (C-F) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; acetic acid; ethyl acetate; | 5.1. Ethyl 7-chloro-3-(3-fluorophenyl)-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate The preparation is carried out as in Example 1.3. from 2.0 g (12.3 mmol) of <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> and from 1.75 g (5.4 mmol) of ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-alpha-oxo-1H-indole-3-acetate in 100 ml of acetic acid. After reacting, the mixture is cooled, 50 ml of water are added and an insoluble material is isolated by filtration and washed with water. It is purified by chromatography on a silica column (eluant: dichloromethane/ethyl acetate: 99/1). After recrystallizing from ethyl acetate, 1.65 g (4.13 mmol) of compound are isolated in the form of a white solid. Melting point: 241-242 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In ethanol; | EXAMPLE 23 Preparation of 1-(3-Fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic Acid Ethyl Ester Similar to Example 1, equimolar amounts of <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> and 2-acetyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis showed that resulting solid was the named product (m.p. 55 C.-56.1 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 26 2-(3-Fluorophenyl)-5-(4-methylsulfonyl)phenyl-4-phenyl-2H-pyridazin-3-one Following the procedure described for example 1, the title compound was prepared from 5-hydroxy-4-(4-methylsulfonyl)phenyl-3-phenyl-5H-furan-2-one and <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> (Et3 N was used to neutralized the HCl salt.). 1 H NMR (Acetone-d6) d 8.16 (s, 1H), 7.90 (d, 2H), 7.60 (m, 5H), 7.35--7.15 (m, 6H), 3.12 (s, 3H). MS (FAB+): m/z 421 (M+ +1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In ethanol; water; | EXAMPLE 10 7-Fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole 4-Piperidone hydrochloride monohydrate (4.55 g) and 3-fluorophenylhydrazine hydrochloride (4.85 g) were added to ethanol (80 ml) and the mixture was heated under reflux for one hour. Hydrogen chloride gas was bubbled into the mixture and refluxing was recommenced for another 1.5 hours. The solution was cooled to 0 C., the hydrochloride was filtered off, washed with ethanol, dissolved in boiling water, decolourised with activated charcoal and filtered. 2M Sodium hydroxide solution was added to the warm solution until it was neutral when tested with pH paper. The pale cream solid was filtered off, washed with water and dried. Recrystallisation from acetonitrile gave a white solid which was a mixture of 7-fluoro and 9-fluoro-isomers in a ratio of 86:14 respectively (HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; hexane; dichloromethane; water; acrylonitrile; | EXAMPLE 4 3-Amino-1-(m-fluorophenyl)-2-pyrazoline A 1.38 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 8.1 g. of <strong>[2924-16-5]m-fluorophenylhydrazine hydrochloride</strong> is added followed in 15 minutes by 2.75 g. of acrylonitrile. The reaction mixture is refluxed for 5 hours, then is evaporated to dryness in vacuo. Water is added and the separated solid is collected by filtration. The solid is dissolved in dichloromethane and the solution is passed through a short column of a hydrous magnesium silicate. The effluent is heated to reflux on a steam bath and hexane is added to precipitate a product. The solid is collected, dissolved in acetone, treated with activated charcoal and filtered. Hexane is added to the filtrate to crystallize 2.95 g. of the product of the Example as off-white needles, m.p. 146-147 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; hexane; dichloromethane; water; | EXAMPLE 36 N-[1-(m-Fluorophenyl)-4-methyl-2-pyrazolin-3-yl]acetamide A 2.8 g. amount of sodium metal is dissolved in 200 ml. of absolute ethanol, then 16.2 g. of <strong>[2924-16-5]m-fluorophenylhydrazine hydrochloride</strong> is added, followed by 13.4 g. of methacrylonitrile. The reaction mixture is refluxed for 18 hours, then the solvent is evaporated in vacuo. Water is added to give a gum. The gum is dissolved in dichloromethane and the solution is passed through a short column of a hydrous magnesium silicate. The effluent is concentrated while adding hexane until turbidity occurs. The solution is cooled and seeded to separate a pink solid which is collected by filtration and dried to give 4.2 g. of 3-amino-1-(m-fluorophenyl)-4-methyl-2-pyrazoline. | |
In ethanol; hexane; dichloromethane; water; | (A) A 2.8 g. amount of sodium metal is dissolved in 200 ml. of absolute ethanol, then 16.2 g. of <strong>[2924-16-5]m-fluorophenylhydrazine hydrochloride</strong> is added followed by 13.4 g. of methacrylonitrile. The reaction mixture is refluxed for 18 hours then the solvent is evaporated in vacuo. Water is added to give a gum. The gum is dissolved in dichloromethane and the solution is passed through a short column of a hydrous magnesium silicate. The effluent is concentrated while adding hexane until turbidity occurs. The solution is cooled and seeded to separate a pink solid which is collected by filtration and dried to give 4.2 g. of 3-amino-1-(m-fluorophenyl)-4-methyl-2-pyrazoline. | |
In ethanol; hexane; dichloromethane; water; | EXAMPLE 3 3-Amino-1-(m-fluorophenyl)-4-methyl-2-pyrazoline A 1.38 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 8.1 g. of <strong>[2924-16-5]m-fluorophenylhydrazine hydrochloride</strong> is added followed by 3.9 g. of methacrylonitrile. The reaction mixture is refluxed for 5 hours, then is evaporated to dryness in vacuo. Water is added to give a dark semi-solid precipitate. The aqueous is decanted then more water is added and the solid is collected by filtration. The solid is dissolved in dichloromethane and the solution is passed through a short column of a hydrous magnesium silicate. The effluent is evaporated to give an oil. The oil is dissolved in hexane, treated with activated charcoal and filtered and evaporated to give a solid. The solid is recrystallized from hexane to give 0.65 g. of the desired product as light orange prisms, m.p. 78-80 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In ethanol; chloroform; | EXAMPLE 238 3-(Dimethylamino)-7-fluoro-1,2,3,4-tetrahydrocarbazole A solution of 35.5 g. of dimethylaminocyclohexanone hydrochloride and 34.5 g. of <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> in 500 ml. of absolute ethyl alcohol was heated at reflux for 20 hours and then cooled in an ice bath. The resulting crystals were collected by filtration, suspended in chloroform, and treated with dilute potassium hydroxide. The chloroform layer was separated and evaporated to dryness under reduced pressure to give, after recrystallizaton from isopropyl alcohol, 31.5 g. of 3-(dimethylamino)-7-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 174-176C. | |
In ethanol; | EXAMPLE 238 3-(Dimethylamino)-7-fluoro-1,2,3,4-tetrahydrocarbazole A solution of 35.5 g. of dimethylaminocyclohexanone hydrochloride and 34.5 g. of <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> in 500 ml. of absolute ethyl alcohol was heated at reflux for twenty hours and then cooled in an ice bath. The resulting crystals were collected by filtration, suspended in chloroform, and treated with dilute potassium hydroxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium nitrite; In diethyl ether; water; at 0 - 20℃; for 3h; | Sodium nitrite (262 mg) dissolved in 1.0 ml of water was dropped, under cooling with ice, into a solution of 500 mg of <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> in 2.5 ml of concentrated hydrochloric acid and 3.0 ml of diethyl ether. Temperature of the reaction solution was raised to room temperature followed by stirring for 3 hours. The reaction solution was diluted with diethyl ether, washed with water and then with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 252 mg of the title compound as a brown oily crude product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; | EXAMPLE 7A 5-Amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile In analogy to the preparation of Example 1A, 1.5 g (31% of theory) of the desired product are obtained starting from 4 g (24.6 mmol) of <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong>, 3 g (24.6 mmol) of ethoxymethylenemalononitrile and 10.3 ml (73.8 mmol) of triethylamine. LC-MS (Method 1): Rt=2.90 min. MS (ESI pos): m/z=203 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=6.81 (s, 2H), 7.28 (m, 1H), 7.36 (m, 2H), 7.57 (m, 1H), 7.80 (s, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | 3-Oxo-4-phenylbutanenitrile (0.831 g, 5.22 mmol) and <strong>[2924-16-5]3-fluorophenyl hydrazine hydrochloride</strong> (0.849 g, 5.22 mmol) were dissolved in ethanol (15 mL). To this mixture was added a catalytic amount of acetic acid (0.1 mL) after which the mixture was heated at reflux for 6 h. The reaction mixture was allowed to cool, and was <n="82"/>partitioned between EtOAc (50 ml_) and 10% aq. NaHCO3 (50 ml_). The phases were separated, and the organic phase was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by MPLC (eluting with 1:3 EtOAc/hexanes) to provide the product 3-benzyl-1-(3-fiuorophenyl)-1H- pyrazol-5-amine (1.16 g, 83%) as a crystalline white solid. 1H NMR (400 MHz, Acetone-de) delta 7.54-7.49 (m, 3 H), 7.35-7.25 (m, 4 H), 7.30-7.21 (m, 1 H), 7.14-7.04 (m, 1 H), 5.40 (s, 1 H), 5.40 (s, 2 H), 3.82 (s, 2 H); LC-MS m/z 268.2 [M+H]+, RT 2.79 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Piperidin-4-one hydrochloride (3.37 g, 24.8 mmol) was dissolved in ethanol (80 mL). Water (3 drops) was added followed by <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> (4.04 g, 24.8 mmol) and the reaction mixture heated at reflux for 1 hour. The mixture was allowed to cool to room temperature and hydrogen chloride gas was bubbled through the solution for approximately 15 minutes. Refluxing was recommenced for 1.5 hours. The suspension was cooled to room temperature overnight, cooled to 0 C. and the resultant filtered and washed with ethanol (c.f. 30 mL). The residue was taken up in water (30 mL), made basic with 2M aqueous sodium hydroxide and the resulting precipitate filtered off and washed with water to afforded the desired compounds as an off white solid consisting of a mixture of isomers (9-fluoro-2,3,4,5-tetrahydropyrido[4,3-B]indole: 7-fluoro-2,3,4,5-tetrahydropyrido[4,3-B]indole (30:70)) (1.76 g, 37% yield). The isomers were inseparable by column chromatography and the mixture was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With hydrogenchloride; water; In ethanol; at 20℃; for 67.5h;Heating / reflux; | Preparation 5: 1 -(3 -Fluoro-phenyl)-3 -methyl- lH-pyrazoleAdd hydrochloric acid (5M, 12 mL, 60 mmol) to a mixture of 4,4- dimethoxybuta-2-one (6.61 g, 6.67 mL, 50 mmol) and <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> (8.13 g, 50 mmol) in ethanol (50 mL). Heat and stir under reflux under nitrogen for 7.5 hr., cool to room temperature, allow to stand for 60 hr. Evaporate the ethanol in vacuo, and chromatograph the residue on silica eluting with DCM. Evaporate the dichlormethane to give l-(3-fluoro-phenyl)-3-methyl-lH-pyrazole as a liquid (4.38 g, 49%). MS (m/z): 171.1 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In ethanol; at 90℃; for 2h; | Step 1: Ethyl 5-amino-1-(3 -fluorophenyl)-1H-pyrazole-4-carboxylate (Compound 10). Compound 10 was made by a method similar to that described in Goldstein, D. M. et al., J. Med. Chem. 2006, 49, 1562-1575. In a 500 mL RBF was weighed ethyl (ethoxymethylene)cyanoacetate (4.49 g, 26.5 mmol) and <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> (4.11 g, 25.3 mmol) followed by ethanol (150 mL). The reaction mixture was treated with TEA (3.87 mL, 27.8 mmol) and heated at 90 0C in an oil bath for 2 h. The volatiles were removed under reduced pressure. The remaining solid was dissolved in EtOAc, washed sequentially with water, 1 N NaOH and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain a yellow solid. This solid was triturated with about 10 mL of ether and about 50 mL of hexanes to afford ethyl 5-amino- 1 -(3 -fluorophenyl)- 1 H-pyrazole-4-carboxylate as a yellow crystalline solid. MS (ESI, pos.ion) m/z: 250.1 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 71 : 4-((S)-4-Carboxy-2-[5-[2-((S)-2-cyclopropylcarbamoyl-pyrrolidin-1-yl)-2-oxo- ethoxy]-1 -(3-fluoro-phenyl)-1 H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1 - carboxylic acid ethyl ester; (i) 4-((S)-4-tert-Butoxycarbonyl-2-[1 -(3-fluoro-phenyl)-5-hydroxy-1 H-pyrazole-3- carbonyl]-amino}-butyryl)-piperazine-1 -carboxylic acid ethyl ester; <n="104"/>To a solution of 2.500 g 1-(3-fluoro-phenyl)-5-hydroxy-1 H-pyrazole-3-carboxylic acid (prepared by Standard procedure using <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> and sodium diethyl-2-oxosuccinate followed by ester hydrolysis) and 3.864 g 4-((S)-2-amino-4-tert- butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 20 ml DMF 1.723 g HOBt1 1.9 ml DIPEA and 2.157 g EDC were added and the reaction mixture was stirred for 16 h at RT. Then the reaction mixture was evaporated, diluted with ethyl acetate and subsequently extracted with aqueous LiCI (4 % w/w) and aqueous NaHCCb. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction. Yield: 7.2 g.; Example 77: 4-((S)-3-Carboxy-2-[5-[2-((S)-2-cyclopropylmethyl-carbamoyl-pyrrolidin-1 -yl)- 2-oxo-ethoxy]-1-(3-fluoro-phenyl)-1 H-pyrazole-3-carbonyl]-amino}-propionyl)-piperazine-1- carboxylic acid ethyl ester; (i) 4-((S)-3-tert-Butoxycarbonyl-2-[1 -(3-fluoro-phenyl)-5-hydroxy-1 H-pyrazole-3- carbonyl]-amino}-butyryl)-piperazine-1 -carboxylic acid ethyl ester; To a solution of 3.199 g 1-(3-fluoro-phenyl)-5-hydroxy-1 H-pyrazole-3-carboxylic acid(prepared by standard procedure using <strong>[2924-16-5]3-fluorophenylhydrazine hydrochloride</strong> and sodium diethyl-2-oxosuccinate followed by ester hydrolysis) and 4.743 g 4-((S)-2-amino-3-tert- butoxycarbonyl-propionyl)-piperazine-1 -carboxylic acid ethyl ester in 26 ml DMF 2.205 g HOBt, 2.5 ml DIPEA and 2.760 g EDC were added and the reaction mixture was stirred for 16 h at RT. Then the reaction mixture was evaporated, diluted with ethyl acetate and subsequently extracted with aqueous LiCI (4 % w/w) and aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction. Yield: 7.2 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; at 85℃; for 72h; | Example 2: {6-fluoro-1-[2-(4-fluorobenzenesulfonyl)benzyl]-2-methyl-1 H- indol-3-yl}acetic acid; Preparation 2a: (6-f luoro-2-methyl-1 H-indol-3-yl)acetic acid ethyl ester; A mixture of <strong>[2924-16-5](3-fluorophenyl)hydrazine hydrochloride</strong> salt (3.5 g), 4-oxo- pentanoic acid (2.3 g) and ethanol (24 ml_) was treated with sulfuric acid (2.0 mL), and the resulting reaction mixture was stirred at 85C for 3 days. The mixture was cooled to room temperature, poured onto a mixture of ice and water and extracted with dichloromethane (3 x 50 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (2.0 mL) and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane, ethyl acetate and formic acid (1 :0:0.001 to 0:1 :0.001 by volume) to afford the title compound as a yellow oil (0.40 g).MS: ESI (+ve) (Method B): 236 (M+H)+, Retention time 3.5 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | A mixture of triphosgene (0.230 g, 0.775 mmol) and sodium carbonate (0.65 g, 6.13 mmol) was suspended in dry DCM (5 mL), cooled down to Oo C under N2. Aniline 1 (0.251 g, 2.14 mmol) was added drop wise to the reaction mixture. The mixture was stirred at the same temperature for 1.5 h. Solid hydrazine hydrochloride 2 (0.370 g, 2.276 mmol) was added followed by TEA (0.599 mL, 4.3 mmol). The reaction mixture was allowed to warm from OoC to r.t. overnight, diluted with DCM, washed with sat. NaHCO3 then water, dried (MgSO4), filtered and concentrated to afford compound 3 (530 mg, 92% yield) that was used in the next step without further purification. MS (m/z): 270.0 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In ethanol; for 2h;Inert atmosphere; Reflux; | Step 1: <strong>[2924-16-5](3-fluorophenyl)hydrazine hydrochloride</strong> (Int-2b, 153.8 mmols, 25 g) and ethanol (400 mL) were added to a IL round-bottomed flask equipped with a reflux condenser and for stirring under nitrogen. l-(pyridin-3-yl)ethanone (Int-2a, 153.8 mmols, 16.84 mL) was added and the resultant solution was heated to reflux for 2h. The reaction solution was cooled to room temperature, filtered, and washed twice with cold ethanol (50 mL). The collected solid was dried in-vacuo to afford the product Int-2c as a bright yellow solid. (147.4 mmols, 33.8 g, 96% Yield) ESI-MS: m/z 230.1 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol; at 20℃; | General procedure: Suitable indoline-2,3-dione 1a-c (1.0 mmol) was dissolved in methanol (5 mL) with gentle heating, then arylhydrazine (2.4 mmol) was slowly added with stirring at room temperature. After stirring overnight, the resulting precipitate was filtered and crystallized or the reaction mixture was evaporated to dryness and the residue suitably purified. |
Tags: 2924-16-5 synthesis path| 2924-16-5 SDS| 2924-16-5 COA| 2924-16-5 purity| 2924-16-5 application| 2924-16-5 NMR| 2924-16-5 COA| 2924-16-5 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
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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