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[ CAS No. 40788-05-4 ] {[proInfo.proName]}

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Chemical Structure| 40788-05-4
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Product Details of [ 40788-05-4 ]

CAS No. :40788-05-4 MDL No. :MFCD20483887
Formula : C8H9F2N Boiling Point : -
Linear Structure Formula :- InChI Key :QDGJIBRTFXRYTH-UHFFFAOYSA-N
M.W : 157.16 Pubchem ID :23445092
Synonyms :

Calculated chemistry of [ 40788-05-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.6
TPSA : 26.02 Ų

Pharmacokinetics

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) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 3.12
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 2.14
Consensus Log Po/w : 2.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.449 mg/ml ; 0.00286 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.639 mg/ml ; 0.00407 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.15 mg/ml ; 0.000957 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.05

Safety of [ 40788-05-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:1760
Hazard Statements:H302-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40788-05-4 ]

* 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 [ 40788-05-4 ]

[ 40788-05-4 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 40788-04-3 ]
  • [ 40788-05-4 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogen In methanol for 3h; 25 Method 25F3-f 1,1 -Difluoroethγl)phenyl]amme; A solution of l-(l,l-difluoroethyl)-3-nitrobenzene (Method 24, 1.2 g, 6.42 mmol) andPd/C (10 %) (120 mg) in MeOH was treated with a H2 atmosphere. The reaction mixture was stirred for 3 h and then filtered through diatomaceous earth. The solvent was removed under reduced pressure to provide an orange oil (958 mg, 95%); m/z 158.
95% With tin(II) chloride dihdyrate In ethanol for 1h; Reflux;
68% With tin(ll) chloride In ethanol for 1h; Heating / reflux; D.2 A mixture of 3.O g (16 mmol) of 1-(1 ,1-difluoroethyl)-3-nitrobenzene, 18.O g (80 mmol) of tin chloride dihydrate and 50 ml_ of ethanol is refluxed for one hour. The mixture is slowly poured on cooled water. The pH is adjusted to 7 by addition of an aqueous 10N solution of sodium hydroxide, then adjusted to 9 by addition of an aqueous saturated solution of sodium hydrogen carbonate. The product is extracted 4 times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The oily residue (2.2 g) is purified over 100 g of silica gel (eluant heptane/ethyl acetate 2/1) to give 1.7 g (68%) of 3-(1 ,1-difluoroethyl)aniline as an oil. 1H NMR: 7.2 (t, 1 H, J = 7.5) ; 6.9 (d, 1 H, J = 7.5) ; 6.8 (s, 1 H) ; 6.9 (d, 1 H, J = 7.5) ;3.8 (broad s, 2H) ; 1.9 (t, 3H, J = 17.5)
With hydrogen In methanol 39.2 Step-2 -Preparation of 3-(1,1-Difluoroethyl)aniline To a solution of 1-(1,1-difluoroethyl)-3-nitrobenzene (1.00 g, 5.34 mmol) in methanol (5.0 mL) was added Pd/C (catalytic amount) and ethylene diamine (catalytic amount). The reaction mixture was subjected for hydrogenation in Parr apparatus under 30 psi for 5-6 h. The excess of solvent was removed under vacuum to afford 0.800 g of the desired product. 1HNMR (DMSO-d6): δ 1.88 (d, J=18.0 Hz, 3H), 3.74 (s, 1H), 7.72 (t, J=8.4 Hz, 1H), 6.81 (s, 1H), 6.87 (d, J=7.8 Hz, 1H), 7.19 (t, J=7.8 Hz, 1H).
With hydrogenchloride; iron In ethanol; water at 20℃; for 2h; 2 Step 2: Synthesis of 3-(l,l-difluoroethyl)aniline Dissolve the nitro compound obtained in Step 1 (870 mg, 4.8 mmol) in ethanol (10 mL), add iron powder (1.3 g, 23.3 mmol), concentrated aqueous HCl (37%, 2.7 mL), stir the reaction at room temperature for 2 hrs. After the reaction, carefully neutralize the mixture with NaOH solution. Filter off the solid, pour the filtrate to ice water (50 mL), extract with EtOAc (15 mLx3), combine the organic layers, wash with brine (100 mL) and dry over anhydrous Na2S04. Concentrate under reduced pressure to get the crude product (760 mg) which is used without further purification.
With hydrogen; iron In ethanol; water at 25℃; for 2h; 2 Synthesis of 3-(1,1-difluoroethyl)aniline
Dissolve the nitro compound obtained in Step 1 (870 mg, 4.8 mmol) in ethanol (10 mL), add iron powder (1.3 g, 23.3 mmol), concentrated aqueous HCl (37%, 2.7 mL), stir the reaction at room temperature for 2 hrs. After the reaction, carefully neutralize the mixture with NaOH solution. Filter off the solid, pour the filtrate to ice water (50 mL), extract with EtOAc (15 mL*3), combine the organic layers, wash with brine (100 mL) and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the crude product (760 mg) which is used without further purification.

  • 2
  • [ 40788-05-4 ]
  • [ 953414-05-6 ]
  • N-[3-(1,1-difluoroethyl)phenyl]-N'-{4-[(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)oxy]phenyl}urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: 3-(1,1-difluoroethyl)aniline; bis(trichloromethyl) carbonate With triethylamine In 1,2-dichloro-ethane at 25 - 70℃; for 2h; Stage #2: 6-(4-aminophenoxy)-3-methylquinazolin-4(3H)-one In tetrahydrofuran for 2h; 15 Example 15N-["3-(l,l-Di£luoroethyl')phenyll-A/'-{4-[(3-metliyl-4-oxo-3.4-dilivdroquinazolin-6- yPoxyiphenyllurea; A solution of [3-(l,l-difluoroethyl)phenyl]amine (Method 25, 70 mg, 0.45 mmol) and TEA (322 μL, 2.22 mmol) in DCE (4 ml) was treated with triphosgene (132 mg, 0.445 mmol). The reaction mixture was stirred at ~25 0C for 30 min and then at 70 0C for 90 min. The solvent was removed under reduced pressure to give the desired intermediate. The resulting solid was dissolved in THF (5 ml) and 6-(4-ammophenoxy)-3-methylquinazolin- 4(3H)-one (Method 9, 100 mg, 0.401 mmol) was added. The reaction mixture stirred for 2 hr. The solvent was removed under reduced pressure and the residue was redissolved in EtOAc. The organics were dried by νaCl(sat) then Na2SO4(S) and the solvents were again removed under reduced pressure. The crude material was purified by reverse phase Gilson to yield 84 mg (42 %) of a white solid. NMR: 9.16 (s, 1 η), 9.07 (s, 1 η), 8.40 (s, 1 η), 7.77 - 7.69 (m, 2 η), 7.58 - 7.45 (m, 4 η), 7.43 - 7.34 (m, 2 η), 7.17 -7.05 (m, 3 η), 3.47 (s, 3 η), 1.94 (t, 3 η); m/z 450.
  • 3
  • [ 40788-05-4 ]
  • [ 334-22-5 ]
  • [ 1000044-18-7 ]
YieldReaction ConditionsOperation in experiment
90% In chlorobenzene Heating / reflux; D.3 A mixture of 2.5 g (15.9 mmol) of 3-(1 ,1-difluoroethyl)aniline and 2.8 g (15.9 mmol) of bis(2-chloroethyl)amine in 20 ml_ of chlorobenzene is refluxed overnight. After cooling to room temperature, diethyl ether is added and precipitation occurs. The solid is filtered, washed with diethyl ether and dried under reduced pressure to give 3.8 g (90%) of 1-[3-(1 ,1-difluoro-ethyl)phenyl]piperazine, hydrochloride as a white solid. 1H NMR (DMSO D6): 9.2 (broad s, 2H) ; 7.3 (t, 1H, J = 7.5) ; 7.15 to 6.95 (ms, 2H) ;7.0 (d, 1 H, J = 7.5) ; 3.4 (m, 4H) ; 3.2 (m, 4H) ; 1.9 (t, 3H, J = 14.5)
  • 4
  • 3-[1-(6-amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-benzoic acid [ No CAS ]
  • [ 40788-05-4 ]
  • C27H23F2N7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25 - 60℃; for 2h;
  • 5
  • [ 121-89-1 ]
  • [ 40788-05-4 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 3-Nitroacetophenone With diethylamino-sulfur trifluoride In dichloromethane for 48h; Reflux; Stage #2: With iron; ammonium chloride In ethanol; water at 20℃; for 18h;
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; methanol / 16 h / 60 °C / Sealed tube 2: hydrogenchloride; iron / water; ethanol / 2 h / 20 °C
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; methanol / 16 h / 60 °C / Sealed tube 2: hydrogen; iron / water; ethanol / 2 h / 25 °C
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 12 h / 80 °C 2: hydrogen / palladium 10% on activated carbon / methanol / 3 h
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 80 °C 2: tin(ll) chloride / ethanol / 1 h / Heating / reflux
Multi-step reaction with 2 steps 1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / -78 - 26 °C 2: hydrogen / palladium on activated charcoal; ethylenediamine / methanol / 1551.49 Torr
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride; ethanol / dichloromethane; toluene / 48 h / 20 °C / Inert atmosphere 2: tin(II) chloride dihdyrate / ethanol / 1 h / Reflux

  • 6
  • [ 40788-05-4 ]
  • [ 1885-14-9 ]
  • [ 1529770-10-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 5℃; for 2h; 3 Step 3: Synthesis of phenyl N-[3-(l,l-difluoroethyl)phenyl]carbamate Dissolve the amine obtained in Step 2 (760 mg, 4.8 mmol) and pyridine (765 mg, 9.7 mmol) in DCM (15 mL) and cool to 0-5°C on ice bath. Add dropwise phenyl chloro formate (831 mg, 5.3 mmol). After addition, stir the mixture at 0-5°C for 2 hrs. Pour the mixture to water (50 mL), adjust pH to neutral with 1M HCl solution. Extract with EtOAc (15 mLx3), combine the organic layers and wash with brine (100 mL), dry over anhydrous Na2S04. Concentrate under reduced pressure to give the crude product (1.15 g) which is used without further purification.
With pyridine In dichloromethane at 0 - 5℃; for 2h; 3 Synthesis of phenyl N-[3-(1,1-difluoroethyl)phenyl]carbamate
Dissolve the amine obtained in Step 2 (760 mg, 4.8 mmol) and pyridine (765 mg, 9.7 mmol) in DCM (15 mL) and cool to 0-5° C. on ice bath. Add dropwise phenyl chloroformate (831 mg, 5.3 mmol). After addition, stir the mixture at 0-5° C. for 2 hrs. Pour the mixture to water (50 mL), adjust pH to neutral with 1M HCl solution. Extract with EtOAc (15 mL*3), combine the organic layers and wash with brine (100 mL), dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product (1.15 g) which is used without further purification.
  • 7
  • [ 40788-05-4 ]
  • ethyl 6-hydroxy-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate [ No CAS ]
  • N-(3-(1,1-difluoroethyl)phenyl)-6-hydroxy-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In N,N-dimethyl-formamide at 100℃; for 0.5h;
  • 8
  • [ 105130-28-7 ]
  • [ 40788-05-4 ]
  • [ 32315-10-9 ]
  • C19H15ClF2N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: 4-(6-Chloropyrimidin-4-yloxy)phenylamine; bis(trichloromethyl) carbonate at 20℃; for 6h; Stage #2: 3-(1,1-difluoroethyl)aniline With triethylamine at 20℃; for 18h;
  • 9
  • [ 105130-28-7 ]
  • [ 40788-05-4 ]
  • 1-(3-(1,1-difluoroethyl)phenyl)-3-(4-((6-(methylamino)-pyrimidin-4-yl)oxy)phenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 6 h / 20 °C 1.2: 18 h / 20 °C 2.1: methanol / 18 h / 20 °C
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Chemical Structure| 1803593-33-0

A1046105[ 1803593-33-0 ]

3-(1,1-Difluoroethyl)aniline hydrochloride

Reason: Free-salt