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Chemical Structure| 7292-74-2 Chemical Structure| 7292-74-2

Structure of H-DL-Phg(3-F)-OH
CAS No.: 7292-74-2

Chemical Structure| 7292-74-2

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Product Details of [ 7292-74-2 ]

CAS No. :7292-74-2
Formula : C8H8FNO2
M.W : 169.15
SMILES Code : O=C(O)C(N)C1=CC=CC(F)=C1
MDL No. :MFCD00049325
InChI Key :LVYBCZIDQKJNFP-UHFFFAOYSA-N
Pubchem ID :265434

Safety of [ 7292-74-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 7292-74-2 ]

* 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 [ 7292-74-2 ]

[ 7292-74-2 ] Synthesis Path-Downstream   1~49

  • 1
  • [ 24424-99-5 ]
  • [ 7292-74-2 ]
  • [ 142121-94-6 ]
YieldReaction ConditionsOperation in experiment
69% To a suspension of <strong>[7292-74-2]2-amino-2-(3-fluorophenyl)acetic acid</strong> (1.00 g, 5.91 mmol) in THF (30 ml) and water (30 ml), 2N sodium hydroxide (29.6 ml, 59.1 mmol) and di-tert-butyl dicarbonate (2.58 g, 1 1.8 mmol) were added and the reaction was stirred at RT for 15h. THF was evaporated, the aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc and the organic phase was washed with brine, dried over Na2SO4 and evaporated to obtain 2-(tert-butoxycarbonylamino)-2-(3- fluorophenyl)acetic acid (1.10 g; 69% yield).
69% With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 15h; To a suspension of <strong>[7292-74-2]2-amino-2-(3-fluorophenyl)acetic acid</strong> (1.00 g, 5.91 mmol) in THF (30 ml) and water (30 ml), were added 2N sodium hydroxide (29.6 ml, 59.1 mmol) and di-tert-butyl dicarbonate (2.58 g, 11.8 mmol), and the reaction was stirred at RT for 15 hours. THF was evaporated, and the aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc, and the organic phase was washed with brine, dried over Na2SO4 and evaporated to obtain 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetic acid (1.10 g; 69% yield).
  • 2
  • (3-Fluoro-phenyl)-[(E)-hydroxyimino]-acetic acid [ No CAS ]
  • [ 7292-74-2 ]
  • 3
  • [ 271583-22-3 ]
  • [ 7292-74-2 ]
YieldReaction ConditionsOperation in experiment
Substitution in the procedure of Example 3 for the N-tert.-butoxycarbonyl derivative of D-α-aminophenylacetic acid (also called D-α-tert.-butoxycarboxamidophenylacetic acid) of an equimolar weight of the N-tert.-butoxycarbonyl derivative of ... D-α-amino-m-methylphenylacetic acid, D-α-amino-p-chlorophenylacetic acid, D-α-amino-m-chlorophenylacetic acid, D-α-amino-p-fluorophenylacetic acid, D-α-amino-m-fluorophenylacetic acid, D-α-amino-p-aminophenylacetic acid, D-α-amino-p-dimethylaminophenylacetic acid, D-α-amino-m,p-dimethoxyphenylacetic acid, ...
The hydantoin was hydrolyzed at reflux using 1 N NaOH giving 2-amino-2-(3-fluorophenyl)acetic acid which was esterified via Procedure H in methanol to give the title compound.
  • 5
  • [ 271583-58-5 ]
  • [ 7292-74-2 ]
  • 6
  • [ 271583-37-0 ]
  • [ 7292-74-2 ]
  • 7
  • [ 456-48-4 ]
  • [ 7292-74-2 ]
  • 8
  • [ 501-00-8 ]
  • [ 7292-74-2 ]
  • 9
  • [ 7292-74-2 ]
  • (R)-1-[2-tert-Butoxycarbonylamino-2-(3-fluoro-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid [ No CAS ]
  • 10
  • [ 7292-74-2 ]
  • C20H17Cl3FNO6 [ No CAS ]
  • 11
  • [ 7292-74-2 ]
  • C32H41FN6O7 [ No CAS ]
  • 12
  • [ 7292-74-2 ]
  • [2-{(S)-2-[(S)-1-(Benzyloxycarbonylamino-imino-methyl)-2-oxo-piperidin-3-ylcarbamoyl]-pyrrolidin-1-yl}-1-(3-fluoro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 13
  • [ 7292-74-2 ]
  • Boc-D-Phg(F)-Pro-Arg-H*HOAc [ No CAS ]
  • 14
  • [ 7292-74-2 ]
  • rac-2-amino-2-(3-fluorophenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃;Heating; D,L-3-fluorophenylglycine (10 g, 59.2 mmol) was added to a suspension of NaBH4 (5.37 g, 142 mmol) in THF (200 mL). The suspension was cooled to 0 C., and an iodine solution (15 g, 59.2 mmol) in THF was added drop wise. The resulting solution was heated while stirring overnight. This solution was cooled to room temperature, quenched with a 20% KOH solution (150 mL) and extracted with DCM (3×). The organics were combined, dried over MgSO4 and the solvent was removed using a rotary evaporator. The product was purified by flash chromatography (0-10% MeOH/EtOAc) to yield 2-amino-2-(3-fluorophenyl)ethanol (I-8) as a white residue.
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃; for 20h;Reflux; Step 1: Preparation of 2-amino- -(3-fluoro-phenyl)-ethanol Amino-(3-fluoro-phenyl)-acetic acid (1.8 g, 10 mmol), NaBH4 (0.95 g, 2.5 mmol) and THF (30 mL) were added dropwise to a solution of iodine (2.54 g, 10 mmol) in anhydrous THF (7 mL) through a pressure-equalizing addition funnel at 0 C. After the ceasing of the hydrogen gas, the reaction mixture was heated to reflux for 20 hours and then cooled to room temperature. The reaction was quenched with methanol, and then dissolved in 20% aqueous KOH. The reaction mixture was stirred overnight to give 1.4 g of crude 2-amino-2-(3-fluoro-phenyl)- ethanol which was directly used in the next step.
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃;Heating; In step 2-1, D,L-3-fluorophenylglycine (10 g, 59.2 mmol) was added to a suspension Of NaBH4 (5.37 g, 142 mmol) in THF (200 mL). The suspension was cooled to 0 0C, and an iodine (15 g, 59.2 mmol) solution in THF was added drop- wise. The resulting solution was heated while stirring over-night. This solution was cooled to room temperature, quenched with a 20 % KOH solution (150 mL), and extracted with dichloro methane (3x). The organics were combined, dried over MgSO4 and the solvent removed using a rotary evaporator. The product was purified with flash chromatography (0 -10 % methanol/ethyl acetate) to yield 2-amino-2-(3-fluorophenyl)ethanol (2-1) as a white residue.
  • 19
  • [ 7292-74-2 ]
  • [ 1365212-63-0 ]
  • 20
  • [ 7292-74-2 ]
  • [ 1365212-76-5 ]
  • 21
  • [ 7292-74-2 ]
  • [ 1365212-77-6 ]
  • (S)-6-(2-(3-fluorophenyl)-2,5-dihydro-1H-pyrrol-1-yl)imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
  • 22
  • [ 7292-74-2 ]
  • [ 1379513-71-9 ]
  • 23
  • [ 7292-74-2 ]
  • [ 1379513-70-8 ]
  • 24
  • [ 7292-74-2 ]
  • [ 1617545-71-7 ]
  • 25
  • [ 7292-74-2 ]
  • [ 1196547-19-9 ]
  • 26
  • [ 91-02-1 ]
  • [ 7292-74-2 ]
  • 3-(3-fluorophenyl)-1-phenylimidazo[1,5-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With di-tert-butyl peroxide; iodine; In toluene; at 120℃; for 12h;Sealed tube; General procedure: To a 10mL reaction tube were added L-Proline-MCM-41-Cu(OTf)2 (71mg, 0.045mmol), 2-benzoylpyridine 1 (0.3mmol), amino acid 2(0.9mmol), molecular iodine (0.045mmol), DTBP (0.75mmol), and toluene (2mL). The reaction tube was sealed and placed in an oil bath at room temperature. The reaction mixture was stirred at 120 C for 12 h. After being cooled to room temperature, the reaction mixture was diluted with 15 mL of EtOAc, and filtered. The L-Proline-MCM-41-Cu(OTf)2 complex was washed with EtOAc (25mL) and ethanol (2 5mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (petroleum ether: EtOAc 15:1-20:1) to provide the desired product 3.
  • 27
  • [ 7292-74-2 ]
  • S-ethyl 3-(3-fluorophenyl)-3-((4-methoxyphenyl)amino)propanethioate [ No CAS ]
  • 28
  • [ 7292-74-2 ]
  • methyl 3-(3-fluorophenyl)-3-((4-methoxyphenyl)amino)-2,2-dimethylpropanoate [ No CAS ]
  • 29
  • [ 7292-74-2 ]
  • [ 104-94-9 ]
  • [ 64222-81-7 ]
  • 30
  • [ 7292-74-2 ]
  • 7-(3,5-dimethylisoxazol-4-yl)-2-(3-fluorophenyl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]
  • 31
  • [ 7292-74-2 ]
  • C14H9BrFNO2 [ No CAS ]
  • 32
  • [ 7292-74-2 ]
  • C14H10Br2FNO2 [ No CAS ]
  • 33
  • [ 7292-74-2 ]
  • C8H5BrClFO [ No CAS ]
  • 34
  • [ 7292-74-2 ]
  • [ 24805-50-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution ofDL-methionine (3.0 g, 20.1 mmol) in H2O (50 mL) was added 30% HBr (20 mL). The reaction mixture was stirred at 0 C for 10 min. A solution of sodium nitrite (1.7 g, 24 mmol) in H2O (50 mL) was added. The reaction mixture was stirred at 0 C for 30 min and thenwarmed to rt for 3 h. The reaction mixture was extracted withEtOAc (100 mL 3). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure to give 3.6 g of intermediate 35c (83% yield).
  • 35
  • [ 7292-74-2 ]
  • [ 1196546-34-5 ]
  • 36
  • [ 7292-74-2 ]
  • [ 643-79-8 ]
  • C16H12FNO3 [ No CAS ]
  • 37
  • [ 7292-74-2 ]
  • C22H15F2N3O4 [ No CAS ]
  • 38
  • [ 7292-74-2 ]
  • C22H17F2N3O2 [ No CAS ]
  • 39
  • [ 7292-74-2 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(3-fluorophenyl)-2-(1-oxoisoindolin-2-yl)acetamide [ No CAS ]
  • 40
  • [ 7292-74-2 ]
  • C16H11ClFNO2 [ No CAS ]
  • 41
  • [ 550313-06-9 ]
  • [ 7292-74-2 ]
  • 42
  • 5-(m-fluorophenyl)hydantoin [ No CAS ]
  • [ 7292-74-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; at 178℃; under 18751.9 Torr; for 0.0666667h; The aqueous solution of 5-(m-fluorophenyl)-hydantoin (Hayin) obtained above and 276 g of an aqueous solution of potassium carbonate having a mass percentage of 50% by weight (hyperin: potassium ion = 1.0: 2.0)At the same time, the metering pump is pumped into the microchannel reactor, and the flow rate in the hyane microchannel is 58.9g/min.The flow rate of the aqueous solution of potassium carbonate in the microchannel is 25.79 g/min.The temperature of the control reaction is 168 C, the pressure is 2.0 MPa, and the residence time is 4 min (ie, the time during which the reaction liquid flows through the microchannel).The liquid flowing out is a clear yellowish transparent liquid, and the liquid is subjected to deamination and carbon dioxide to obtain 845.2447 g of an aqueous solution of potassium p-fluorophenylglycine.The mass percentage of fluorophenylglycine in the middle is 20.01% by weight, the mass percentage of potassium ion is 9.23% by weight, and the yield of m-fluorophenylglycine is 99.9% or more. The hydrolyzate obtained above is introduced into carbon dioxide gas, the pressure of the carbon dioxide gas is 0.3 MPa, the neutralization temperature is 20 C, and the stirring speed is 120 r/min.The carbon dioxide neutralization end point was pH 7.8, the solid was filtered off, washed with water, and dried to obtain 138.0841 g of m-fluorophenylglycine product, the main content was 98 wt%.The product is in the form of powder and undergoes recrystallization operation to obtain a crystalline DL-o-fluorophenylglycine product having a purity of 99.5 wt% or more, and the recrystallization mother liquor is recycled.The filtrate is an aqueous solution of potassium hydrogencarbonate containing o-fluorophenylglycine, and the mass of the filtrate is 760.5740 g, wherein the mass percentage of potassium ions is 10.26 wt%.The mass percentage of m-fluorophenylglycine is 4.45 wt%, and the filtrate is decarburized by heating, concentrated to a potassium ion mass percentage of 30 wt%, and recycled to the next batch of hydantoin hydrolysis.The mass of the mother liquid obtained after decarburization and concentration was 260.1142 g, and the mass percentage of the intermediate fluorophenylglycine was 13.0% by weight.
  • 43
  • [ 108-30-5 ]
  • [ 7292-74-2 ]
  • C12H12FNO5 [ No CAS ]
  • 44
  • [ 7292-74-2 ]
  • C12H10FNO4 [ No CAS ]
  • 45
  • [ 7292-74-2 ]
  • C23H21F4N3O3 [ No CAS ]
  • 46
  • [ 7292-74-2 ]
  • methyl 2-(7-bromo-1-oxoisoquinolin-2(1H)-yl)-2-(3-fluorophenyl)acetate [ No CAS ]
  • 47
  • [ 7292-74-2 ]
  • methyl 2-(7-bromo-4-oxoquinazolin-3(4H)-yl)-2-(3-fluorophenyl)acetate [ No CAS ]
  • 48
  • [ 67-56-1 ]
  • [ 7292-74-2 ]
  • methyl 2-amino-2-(3-fluorophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.49 g With thionyl chloride; at 0 - 60℃; for 16.5h; Thionyl chloride (7. /2 ml, 0.106 moi) was added dropwise to a mixture of 2-amino-2- (3-fiuoropheny)acetic acid (6.0 g, 0.035 mol) in methanol (100 L) at 0C. The reaction was stirred at room temperature for 30 minutes, then at 6QC for 16 hours. The solvents were removed under reduced pressure, and the residue was dissolved in EtOAc (150 mL). The organic layer was washed with saturated brine and saturated NaHC03, dried (Na2S04) and concentrated to give the title compound, used without further purification (6.49 g).1H NM (500 MHz, de-DMSO) d 7.35 (m, 1 H) 7.20 (d, 1 H) 7.15 (d, 1 H) 7.03 (m, 1 H) 3.74 (s, 3H).
  • 49
  • [ 7292-74-2 ]
  • [ 106-49-0 ]
  • [ 67-68-5 ]
  • 2-(3-fluorophenyl)-6-methylquinazoline [ No CAS ]
 

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