Home Cart 0 Sign in  

[ CAS No. 867288-00-4 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 867288-00-4
Chemical Structure| 867288-00-4
Structure of 867288-00-4 *Storage: {[proInfo.prStorage]}

Quality Control of [ 867288-00-4 ]

Related Doc. of [ 867288-00-4 ]

SDS
Alternatived Products of [ 867288-00-4 ]
Alternatived Products of [ 867288-00-4 ]

Product Details of [ 867288-00-4 ]

CAS No. :867288-00-4MDL No. :MFCD14585527
Formula : C13H11F2NO Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :235.23Pubchem ID :53375439
Synonyms :

Computed Properties of [ 867288-00-4 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 867288-00-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 867288-00-4 ]

  • Downstream synthetic route of [ 867288-00-4 ]

[ 867288-00-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 867288-00-4 ]
  • [ 3205-94-5 ]
  • 2-(3,5-difluoro-3'-methoxy-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid [ No CAS ]
  • 3
  • [ 10365-98-7 ]
  • [ 67567-26-4 ]
  • [ 867288-00-4 ]
YieldReaction ConditionsOperation in experiment
61% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; for 3.5h;Inert atmosphere; 4-bromo-2.6-difluoro-aniline 1 g (4.81 mmol) and m-methoxyphenylboronic acid 730 mg (4.81 mmol. 1 eq)Potassium carbonate (4.82 g 24.88 mmol 6 eq) [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (425.35 mg481 mmol 6 eq) was placed in a 100 ml two-necked flask, and 30 ml (dioxane: water = 3:1) was injected with nitrogen to protect the solution, and 80 was allowed to react for 3.5 h. After the TLC monitoring reaction is completed, the post-treatment distillation is carried out under reduced pressure to about 10 ml, and the solution is poured into a separating funnel, extracted with dichloromethane for 2-3 times, dried over anhydrous Na 2 SO 4 , filtered, and evaporated to dryness to give a black oily drop. Separated and purified by petroleum ether: ethyl acetate = 6:1 silica gel column chromatography to obtain a pale yellow oily liquid about 690 mg, yield 61percent.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; toluene; at 72℃; for 4h;Industry scale; Inert atmosphere;Product distribution / selectivity; 10 kg of <strong>[67567-26-4]4-bromo-2,6-difluoroaniline</strong> (48.08 mol) and 67 L of toluene were charged into a reactor under nitrogen atmosphere and stirred at 20 °C until complete dissolution. 1.67 kg of Pd(PPh3)4 (1.44 mol) were charged and stirred for 10 min. 48 L of a 20 wt. percent aqueous solution of Na2C03 were then charged, followed by the addition of a solution of 3- methoxyboronic acid (8.77 kg, 57.7 mol) in methanol (32 L) over 20 minutes. The mixture was heated at 72 °C for 4 hours and then cooled to 20 °C.
YieldReaction ConditionsOperation in experiment
With ammonia; sodium carbonate; In Isopropyl acetate; water;Industry scale;Purification / work up; A solution of 123 L of a 10% aqueous solution of Na2C03, 1.5 L of a 25 wt. % aqueous solution of ammonia and 2.0 kg of a filtration resin (Dicalite) were charged to the reactor and the mixture stirred for 5 minutes. The mixture was recirculated through a filter until clarification of the liquors (35 min) and charged into a reactor. 60 L of isopropyl acetate were added and the mixture was stirred for 10 minutes and the phases (A1 +01 ) were allowed to separate. The aqueous phase (A1 ) was transferred to a different reactor and 60 L of isopropyl acetate were charged. The mixture was stirred and the phases (A2 + 02) were allowed to separate. Both organic phases (01+02) were charged into a reactor and 108 L of a 10 wt. % aqueous solution of Na2C03 were added. The mixture was stirred and the phases (A3+03) were allowed to separate. The organic phase (03) was stirred with 108 L of a 10 wt. % aqueous solution of Na2C03 and the phases (A4+04) were allowed to separate. The organic phase (04) was stirred with 100 L demineralised water and the phases (A5+05) were allowed to separate. The organic phase (05) was filtered over a filtration resin (Dicalite) in a filter and charged in to a reactor. 2.2. Distillation: The organic phase (05) was distilled during 2 hours under reduced pressure (approx. 750 mm Hg) keeping the distilled mixture at temperature below 65 C.
With a filtration resin (Dicalite); In water; ethyl acetate;Purification / work up; 2) Purification of <strong>[867288-00-4]3,5-difluoro-3'-methoxybiphenyl-4-amine</strong> 2.1. 600 mL of isopropyl acetate were added and the mixture was stirred for 10 minutes and the phases (A1 +O1) were allowed to separate. The aqueous phase (A1) was stirred with 600 mL of isopropyl acetate for 10 minutes and the phases (A2 + 02) were allowed to separate. Both organic phases (O1+O2) were stirred with 600 mL demineralised water and the phases (A3+O3) were allowed to separate. The organic phase (03) was filtered over a filtration resin (Dicalite) in a filter. 2.2. Distillation: The organic phase (03) was distilled under reduced pressure (approx. 750 mm Hg) keeping the distilled mixture at temperature below 65C to yield a dark coloured oil residue.
  • 5
  • [ 867288-00-4 ]
  • [ 1290050-53-1 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; In Isopropyl acetate; water; at 0 - 5℃; for 2h;pH < 2;Product distribution / selectivity; The distillation residue was dissolved in 800 L of isopropyl acetate (8 vol/w) , the mixture was cooled to 0-5 C and 50 mL of a 35 wt. % aqueous solution of HCI were added drop- wise until the pH was lower than 2. The aminium salt precipitated as a white solid from the dark brown coloured solution. The slurry was stirred for 2 hours at 0-5 C, filtered and the cake washed twice with 50 mL of previously cooled isopropyl acetate. The cake was pulled dry under reduced pressure and dried at 60 C under reduced pressure (approx. 750 mm Hg) to constant weight. A total of 1 17 g (0.431 mmol, 89 % yield) of 3,5-difluoro- 3'-methoxybiphenyl-4-aminium chloride were isolated as beige solid
89% With hydrogenchloride; In Isopropyl acetate; water; at 0 - 5℃;pH 2;Product distribution / selectivity; 3) Preparation of the aminium salt (step b) The distillation residue was dissolved in 800 L of isopropyl acetate (8 vol/w) , the mixture was cooled to 0-5 C and 50 mL of a 35 wt. % aqueous solution of HCl were added drop-wise until the pH was lower than 2. The aminium salt precipitated as a white solid from the dark brown coloured solution. The slurry was stirred for 2 hours at 0-5 C, filtered and the cake washed twice with 50 mL of previously cooled isopropyl acetate. The cake was pulled dry under reduced pressure and dried at 60 C under reduced pressure (approx. 750 mm Hg) to constant weight. A total of 117 g (0.431 mmol, 89 % yield) of 3,5-difluoro-3'-methoxybiphenyl-4-aminium chloride were isolated as beige solid.
  • 6
  • [ 867288-00-4 ]
  • [ 85-44-9 ]
  • [ 1346705-25-6 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane;Reflux; Procedure-1A solution of an anhydride (1.3 eq.) and an amine (1 eq) were dissolved in dioxane and refluxed overnight. Dioxane was evaporated and the resultant residue dissolved in AcOEt and extracted into aq. 2N NaHCO3 solution. The aqueous layer was acidified with aq. 2N HCl to obtain a solid, which was filtered and dried to give the desired amide.Examples 1-11, 14, 16-17 and 20 were synthesized using general procedure-1. EXAMPLE 1 2-(3,5-Difluoro-3'-methoxybiphenyl-4-ylcarbamoyl)benzoic acid The title compound (52 mg) was obtained from intermediate 1 (150 mg, 0.64 mmol) and phthalic anhydride (189 mg) as a white solid. M.P.: 168-173 C. 1H-NMR (delta ppm, DMSO-d6, 400 MHz): 13.05 (s, 1H), 10.19 (s, 1H), 7.83 (d, J7.4, 1H), 7.69-7.63 (m, 1H), 7.62-7.52 (m, 4H), 7.39 (t, J 7.9, 1H), 7.34-7.27 (m, 2H), 6.98 (d, J 6.8, 1H), 3.83 (s, 3H). MS (m/z): 381.55 ([M-H]-).
In 1,4-dioxane;Reflux; Procedure -1A solution of an anhydride (1.3 eq.) and an amine (1 eq) were dissolved in dioxane and refluxed overnight. Dioxane was evaporated and the resultant residue dissolved in AcOEt and extracted into aq. 2N NaHC03 solution. The aqueous layer was acidified with aq. 2 HC1 to obtain a solid, which was filtered and dried to give the desired amide.Example 12-(3^-Difluoro-3'-methoxybiphenyl-4-yIcarbainoyI)berizoic acid:The title compound (52 mg) was obtained from intermediate 1 (150 mg, 0.64 mmol) and phthalic anhydride (189 mg) as a white solid. MJ: 168-173G te-NMR (delta ppm, DUSO- k, 400 MHz): 13.05 (s, 1H), 10.19 (s, 1H), 7.83 (d, J 7.4, 1H), 7.69-7.63 (m, 1H), 7.62-7.52 (m, 4H), 7.39 (t, / 7.9, 1H), 7.34-7.27 (m, 2H), 6.98 (d, / 6.8, 1H), 3.83 (s, 3H). MS (m z): 381.55 ([itf-H]").
  • 7
  • [ 867288-00-4 ]
  • [ 280-57-9 ]
  • [ 75-15-0 ]
  • C14H11F2NOS2*C6H12N2 [ No CAS ]
Historical Records

Related Functional Groups of
[ 867288-00-4 ]

Fluorinated Building Blocks

Chemical Structure| 867287-99-8

[ 867287-99-8 ]

3-Fluoro-3'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.98

Chemical Structure| 893734-49-1

[ 893734-49-1 ]

3-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.95

Chemical Structure| 1035689-62-3

[ 1035689-62-3 ]

3-Fluoro-3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-amine

Similarity: 0.86

Chemical Structure| 217314-46-0

[ 217314-46-0 ]

2-Fluoro-6-methoxy-4-methylaniline

Similarity: 0.82

Chemical Structure| 1373233-05-6

[ 1373233-05-6 ]

3-(4-Fluoro-3-methoxyphenyl)aniline, HCl

Similarity: 0.80

Amines

Chemical Structure| 867287-99-8

[ 867287-99-8 ]

3-Fluoro-3'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.98

Chemical Structure| 893734-49-1

[ 893734-49-1 ]

3-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.95

Chemical Structure| 1035689-62-3

[ 1035689-62-3 ]

3-Fluoro-3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-amine

Similarity: 0.86

Chemical Structure| 217314-46-0

[ 217314-46-0 ]

2-Fluoro-6-methoxy-4-methylaniline

Similarity: 0.82

Chemical Structure| 1373233-05-6

[ 1373233-05-6 ]

3-(4-Fluoro-3-methoxyphenyl)aniline, HCl

Similarity: 0.80

Aryls

Chemical Structure| 867287-99-8

[ 867287-99-8 ]

3-Fluoro-3'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.98

Chemical Structure| 893734-49-1

[ 893734-49-1 ]

3-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.95

Chemical Structure| 1035689-62-3

[ 1035689-62-3 ]

3-Fluoro-3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-amine

Similarity: 0.86

Chemical Structure| 217314-46-0

[ 217314-46-0 ]

2-Fluoro-6-methoxy-4-methylaniline

Similarity: 0.82

Chemical Structure| 1373233-05-6

[ 1373233-05-6 ]

3-(4-Fluoro-3-methoxyphenyl)aniline, HCl

Similarity: 0.80

Ethers

Chemical Structure| 867287-99-8

[ 867287-99-8 ]

3-Fluoro-3'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.98

Chemical Structure| 893734-49-1

[ 893734-49-1 ]

3-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-amine

Similarity: 0.95

Chemical Structure| 1035689-62-3

[ 1035689-62-3 ]

3-Fluoro-3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-amine

Similarity: 0.86

Chemical Structure| 217314-46-0

[ 217314-46-0 ]

2-Fluoro-6-methoxy-4-methylaniline

Similarity: 0.82

Chemical Structure| 1373233-05-6

[ 1373233-05-6 ]

3-(4-Fluoro-3-methoxyphenyl)aniline, HCl

Similarity: 0.80