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Chemical Structure| 658-27-5 Chemical Structure| 658-27-5

Structure of 658-27-5

Chemical Structure| 658-27-5

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Product Details of [ 658-27-5 ]

CAS No. :658-27-5
Formula : C6H7FN2
M.W : 126.13
SMILES Code : NNC1=CC=CC(F)=C1
MDL No. :MFCD00041261
InChI Key :HFSXFDKOXKNGIA-UHFFFAOYSA-N
Pubchem ID :581026

Safety of [ 658-27-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H315-H318-H335
Precautionary Statements:P280-P301+P310+P330-P302+P352-P305+P351+P338+P310
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 658-27-5 ]

* 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.

  • Downstream synthetic route of [ 658-27-5 ]

[ 658-27-5 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 50-99-7 ]
  • [ 658-27-5 ]
  • [ 454-17-1 ]
  • 2
  • [ 372-19-0 ]
  • [ 658-27-5 ]
YieldReaction ConditionsOperation in experiment
74.81% General procedure: Substituted aniline (0.17mol) and aqueous solution of NaNO2 (71.0mL, 1.24mol) were successively added to aqueous hydrochloric acid (115mL) maintaining the temperature between 0 and 5C. The reaction mixture was stirred for 2h, alkalized to pH 6-7 with 12% w/v sodium carbonate solution, and the resulting diazonium salt solution was added drop-wise to sodium sulfite solution (443.0mL, 1.9mol) below 0C. And then the mixture was stirred at room temperature for a future 1h, concentrated hydrochloric acid (277.0mL) was added slowly, and heated to 100C for 3h. The mixture was then cooled and filtered, and dried to give compounds 12a-e.
General procedure: Substituted aniline 4a-4s (50 mmol) was dissolved in the 50 mL HCl (18%, aqueous) in the icebath. NaNO2 (50 mmol) dissolved in 50 mL water was added dropwise. The reaction mixture wasstirred for 1 h to obtain a clear solution. Then the solution of SnCl2 (0.1 mol) in 30 mL of concentratedHCl was added dropwise at 0 C. The mixture was stirred at room temperature for 2 h. Afterwards,the mixture was extracted with 50 mL EtOAc and the organic impurities were discarded. Then thesolution was basified with NaOH (40%, aqueous) until it reached pH 7.0. The reaction mass wasextracted with EtOAc three times. Finally, substituted phenylhydrzine 5a-5s was afforded after beingvapored under reduced pressure (in 55%-80% yield) [12].
22.1 g A process for the preparation of 3-fluorophenylhydrazine hydrochloride, comprising the steps of: [0019] diazotization [0020] was added in a 1 L three-necked flask 50 g of 3-fluoroaniline and 150 ml of 37% concentrated hydrochloric acid, Cool with ice salt to 2 C 35% aqueous sodium nitrite solution was added with stirring, The temperature was maintained at 2 C for 1 hour.reduction [0022] To the reaction solution was added 37 ml of concentrated hydrochloric acid (450 ml), 450 ml of water and 120 g of zinc powder, and the temperature was maintained at 18 C To complete reaction, the reaction solution becomes gray and then add 20% sodium hydroxide solution to the reaction solution PH value of 10,5 C insulation 1 Hour, precipitation of crystals, filter was 26. 6g 3-fluorophenylhydrazine crude. [0023] purification [0024] A crude product of 26. 6 g of 3-fluorophenylhydrazine was dissolved in 532 g of water, heated to 60 C to completely dissolve, and then Charcoal decolorization for 20 minutes, hot and filtered to a colorless filtrate, 5 C insulation for 1 hour, precipitation of crystals, filtration was 22. lg 3 - fluorophenylhydrazine Pure.
292 g (1) Diazotization: 10 g of a three-necked flask was added with 500 g of 3-fluoroaniline and 1500 ml of 37% concentrated hydrochloric acid, cooled with ice salt to 2 C, and 857 g of 35% aqueous solution of sodium nitrite was added with stirring. The temperature was maintained at 0 to 5 C for 1.5 hours. (2) Reduction: To the reaction solution was added 730 ml of 37% concentrated hydrochloric acid, 730 ml of water and 480 g of zinc powder, the reaction was maintained at a temperature between 18 C and the reaction was completed. The reaction liquid becomes off-white. Then 30% sodium hydroxide solution was added to the reaction solution to adjuste the pH value of 10.5 for 2 hours, crystals were precipitated and filtered to obtain crude 292 g 3-fluorophenylhydrazine. (3) Purification: A crude product of 292 g of 3-fluorophenylhydrazine was dissolved in 5840 g of water, heated to 60 C to completely dissolve, then right amount of activated carbon was added, decolorized for 20 minutes, hot-filtered at 5C for 2 hours to a colorless filtrate, crystallized, and filtered to give 236 g of pure 3-fluorophenylhydrazine. (4) Salt: A pure product of 236 g of 3-fluorophenylhydrazine was dissolved in 408 ml of 40% sulfuric acid, crystals were precipitated by stirring at 65 C to the reaction solution, cooled to 20 C, filtered, the filter cake was washed with acetone and dried to obtain 3-fluorophenylhydrazine sulfate finished product 379 g, Content of 99.3%,Yield 42.7%.

  • 3
  • [ 122-51-0 ]
  • [ 658-27-5 ]
  • [ 109-77-3 ]
  • [ 51516-71-3 ]
  • 4
  • [ 26893-17-4 ]
  • [ 658-27-5 ]
  • 2-(3-Fluoro-phenyl)-2,5-dihydro-7,9-dioxa-1,2,5-triaza-dicyclopenta[a,g]naphthalen-3-one [ No CAS ]
  • 6
  • [ 98263-41-3 ]
  • [ 658-27-5 ]
  • (2-Fluoro-7,12-dihydro-6H-5,7,12-triaza-indeno[1,2-a]fluoren-5-yl)-phenyl-methanone [ No CAS ]
  • 7
  • [ 98263-41-3 ]
  • [ 658-27-5 ]
  • (2-Fluoro-7,12-dihydro-6H-5,7,12-triaza-indeno[1,2-a]fluoren-5-yl)-phenyl-methanone [ No CAS ]
  • (4-Fluoro-7,12-dihydro-6H-5,7,12-triaza-indeno[1,2-a]fluoren-5-yl)-phenyl-methanone [ No CAS ]
  • 8
  • [ 98263-41-3 ]
  • [ 658-27-5 ]
  • [ 106252-00-0 ]
  • 4-Fluoro-7,12-dihydro-5,7,12-triaza-indeno[1,2-a]fluorene [ No CAS ]
  • 9
  • [ 79240-21-4 ]
  • [ 658-27-5 ]
  • 3-<1-(3-pyridyl)ethyl>-6-fluoroindole [ No CAS ]
  • 3-<1-(3-pyridyl)ethyl>-4-fluoroindole [ No CAS ]
  • 10
  • [ 149301-52-0 ]
  • [ 658-27-5 ]
  • 8-Butyl-2-(3-fluoro-phenyl)-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 11
  • [ 149301-52-0 ]
  • [ 658-27-5 ]
  • 8-Cyclohexyl-2-(3-fluoro-phenyl)-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 12
  • [ 150258-20-1 ]
  • [ 658-27-5 ]
  • 6,8-Difluoro-2-(3-fluoro-phenyl)-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 13
  • [ 150258-21-2 ]
  • [ 658-27-5 ]
  • 7,9-Dichloro-2-(3-fluoro-phenyl)-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 14
  • [ 81761-73-1 ]
  • [ 658-27-5 ]
  • [ 81761-79-7 ]
  • 15
  • [ 658-27-5 ]
  • [ 99-93-4 ]
  • [ 104815-80-7 ]
  • 17
  • [ 123-54-6 ]
  • [ 658-27-5 ]
  • [ 81329-49-9 ]
  • 18
  • [ 122-31-6 ]
  • [ 658-27-5 ]
  • 1-(3-fluorophenyl)-1H-pyrazole [ No CAS ]
  • 19
  • [ 658-27-5 ]
  • [ 207231-23-0 ]
  • 2-(3-Fluoro-phenyl)-8-trifluoromethoxy-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 20
  • [ 64-17-5 ]
  • [ 1049019-27-3 ]
  • [ 658-27-5 ]
  • [ 220000-31-7 ]
  • 21
  • [ 658-27-5 ]
  • [ 75706-11-5 ]
  • 1-(3-Fluoro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (4-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 25
  • [ 658-27-5 ]
  • [ 328088-55-7 ]
  • 2-cyano-5-fluoro-3-methyl-9H,10H-indolizino[1,2-b]indole-1-one [ No CAS ]
  • 2-cyano-7-fluoro-3-methyl-9H,10H-indolizino[1,2-b]indole-1-one [ No CAS ]
  • 26
  • [ 23572-06-7 ]
  • [ 658-27-5 ]
  • <i>N</i>-(3-fluoro-phenyl)-<i>N</i>'-[phenyl-(5-phenyl-[1,2,4]oxadiazol-3-yl)-methylene]-hydrazine [ No CAS ]
  • 27
  • [ 658-27-5 ]
  • [ 2642-63-9 ]
  • [ 1026622-41-2 ]
  • 28
  • [ 658-27-5 ]
  • [ 462654-15-5 ]
  • acetic acid 3-acetoxy-5-[(3-fluoro-phenyl)-hydrazonomethyl]-9-oxo-9<i>H</i>-xanthen-1-yl ester [ No CAS ]
  • 29
  • [ 658-27-5 ]
  • [ 462654-16-6 ]
  • acetic acid 3-acetoxy-2,4-dichloro-5-[(3-fluoro-phenyl)-hydrazonomethyl]-9-oxo-9<i>H</i>-xanthen-1-yl ester [ No CAS ]
  • 30
  • [ 333-20-0 ]
  • [ 2114-00-3 ]
  • [ 658-27-5 ]
  • 1-(3-fluoro-phenylamino)-4-methyl-5-phenyl-1<i>H</i>-imidazole-2-thiol [ No CAS ]
  • 31
  • [ 617-35-6 ]
  • [ 658-27-5 ]
  • [ 404-69-3 ]
  • 32
  • [ 658-27-5 ]
  • [ 635325-01-8 ]
  • [ 635325-08-5 ]
YieldReaction ConditionsOperation in experiment
88% 2,6-di-tert-butyl-4-methylpyridine; In toluene; for 36h;Heating / reflux; EXAMPLE 78 Preparation of 2-(3-Fluorophenyl)-6-methyl-1,2,5,6-tetrahydro-1,2,5,6,7-pentaza-as-indacene-3,4-dione A suspension of ethyl 4-chloro-1-methyl-6-trifluoromethanesulfonyloxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (524 mg, 2.05 mmol) in toluene is treated with <strong>[658-27-5]3-fluorophenyl hydrazine</strong> (651 mg, 5.13 mmol) and a catalytic amount of 2,6-di-t-butyl-4-methylpyridine, heated at reflux temperature for 36 h, cooled to room temperature and filtered.The filtercake is washed with cold toluene and dried in vacuo to give the 4-hydrazinyl intermediate as a white powder, 624 mg (88% yield).This white powder (550 mg, 1.59 mmol) is suspended in THF, treated with NaH (60% in oil, 187 mg, 5.58 mmol), heated at reflux temperature for 24 h, cooled to room temperature, quenched carefully with 10% HCl, diluted with EtOAc and filtered.The filtercake is washed sequentially with water and EtOAc and air-dried to afford the title product as a white powder, 391 mg (83% yield, 73% yield over 2 steps), identified by HNMR and mass spectral analyses.
  • 33
  • [ 658-27-5 ]
  • [ 726134-68-5 ]
  • 4-[<i>N</i>'-(3-fluoro-phenyl)-hydrazino]-1-methyl-6-thiophen-3-yl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carboxylic acid ethyl ester [ No CAS ]
  • 34
  • [ 658-27-5 ]
  • [ 635325-78-9 ]
  • 2-(3-fluoro-phenyl)-4-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyrazolo[4,3-<i>c</i>]pyridin-3-one [ No CAS ]
  • 35
  • [ 658-27-5 ]
  • [ 635324-65-1 ]
  • [ 635325-89-2 ]
  • 36
  • [ 658-27-5 ]
  • [ 635324-62-8 ]
  • [ 635325-91-6 ]
 

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