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[ CAS No. 124185-35-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 124185-35-9
Chemical Structure| 124185-35-9
Chemical Structure| 124185-35-9
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Product Details of [ 124185-35-9 ]

CAS No. :124185-35-9 MDL No. :MFCD00055369
Formula : C7H7ClFN Boiling Point : -
Linear Structure Formula :- InChI Key :OXINUINVVAJJSE-UHFFFAOYSA-N
M.W : 159.59 Pubchem ID :2724818
Synonyms :

Calculated chemistry of [ 124185-35-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.78
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) : -5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.33
Log Po/w (WLOGP) : 2.8
Log Po/w (MLOGP) : 2.84
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 2.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.29 mg/ml ; 0.00181 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.487 mg/ml ; 0.00305 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.31
Solubility : 0.0783 mg/ml ; 0.000491 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 124185-35-9 ]

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:

Application In Synthesis of [ 124185-35-9 ]

* 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 [ 124185-35-9 ]

[ 124185-35-9 ] Synthesis Path-Downstream   1~40

  • 2
  • [ 124185-35-9 ]
  • [ 552-30-7 ]
  • [ 371157-46-9 ]
YieldReaction ConditionsOperation in experiment
Multistep reaction;
  • 3
  • [ 124185-35-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ 124185-36-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium nitrite In dichloromethane; water; ethyl acetate; acetone V.1 Example V-1 STR53 40 ml of 25 per cent hydrochloric acid and 28.8 ml (0.37 mol) of acrylonitrile are added to 19.6 g (0.12 mol) of 2-chloro-4-fluoro-5-methylaniline in 40 ml of acetone, 8.7 g (0.13 mol) of sodium nitrite in 17 ml of water are then added dropwise with stirring at 0° C. to 10° C. in the course of one hour, the mixture is stirred for a further hour at 0° C. to 10° C., and several portions of copper(II) oxide powder are then added, with nitrogen gas vigorously evolving. When the evolution of gas has ended, the mixture is stirred for a further 15 hours at room temperature, dichloromethane is then added, the mixture is washed with water, dried over sodium sulphate and concentrated in vacuo, and the oily residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). 25.3 g (90% of theory) of 2-chloro-3-(2-chloro-4-fluoro-5-methylphenyl)-propionitrile are obtained as an oil. 1 H-NMR (CDCl3 /TMS): δ=2.3 (3 H); 3.4 (2 H); 4.7 (1 H); 7.0-7.2 (2 H) ppm.
  • 4
  • [ 124185-35-9 ]
  • [ 922511-38-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-chloro-4-fluoro-5-methylaniline With hydrogenchloride; trifluoroacetic acid; sodium nitrite In water at 0℃; for 1h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0 - 20℃; for 15h; 43.A Example 43 6-Chloro-8-fluoro-9-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride Step A.; A solution of sodium nitrite (1.1 g, 15.9 mmol) and H20 (3.3 mL) was added dropwise at 0° C. to a solution of 2-chloro-4-fluoro-5-methylbenzenamine (2.1 g, 13.2 mmol) in 12N HCl (31.4 mL) and TFA (4.0 mL). The reaction mixture was stirred at 0° C. for 1 h followed by the dropwise addition of a solution of tin(II)chloride (5.5 g, 29.1 mmol) in 12N HCl (7.9 mL) and H2O (1.0 mL) at 0° C. The reaction mixture stirred for 15 h at 20° C. and was filtered to give 1-(2-chloro-4-fluoro-5-methylphenyl)hydrazine hydrochloride (2.7 g, 12.8 mmol).
  • 5
  • [ 124185-35-9 ]
  • [ 14109-72-9 ]
  • [ 628736-90-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-chloro-4-fluoro-5-methylaniline With tert-butylhypochlorite In dichloromethane at -65℃; for 0.166667h; Stage #2: methylsulfanyl-acetone In dichloromethane at -65℃; for 1h; Stage #3: With triethylamine In dichloromethane at -65℃; 48.a Example 48; [3"2-BENZISOTHIAZOL-3-VL)-7-CHLORO-5-LLUORO-2W4-DIMETHVL-LH-INDOL-L-YLLACETIC ACID]; a) [7-CHLORO-5-FLUORO-24-DIMETHEL-3-METHYLTHIO-LH-INDOLE] A stirred solution of [2-CHLORO-4-FLUORO-5-METHYLANILINE] (1.655 g) in methylene chloride (100 ml) under nitrogen was treated at-65°C with a solution of tbutylhypochlorite (1.126 g) in methylene chloride (5 ml), stirred at-65 °C for 10 min, treated at-65°C with a solution of methylthioacetone [(1.] [080G)] in methylene chloride (5 ml) stirred at-65°C for 1 hour, treated at-65°C with triethylamine (1.05 g) and allowed to reach ambient temperature. The solution was washed, dried [(MGS04)] and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the sub-title compound (1.704 g). MS: APCI (-ve): 242 [M-H]- ['H] NMR (DMSO-d6) [6] 11.67 [(1H,] s), 7.07 [(1H,] d), 2.71 (3H, d), 2. [48] (3H, s), 2.19 (3H, s).
Stage #1: 2-chloro-4-fluoro-5-methylaniline With tert-butylhypochlorite In dichloromethane at -65℃; for 0.166667h; Nitrogen atmosphere; Stage #2: methylsulfanyl-acetone In dichloromethane at -65℃; for 1h; Nitrogen atmosphere; Stage #3: With triethylamine In dichloromethane at -65 - 20℃; 43.i Example 43; [3-R (4-CHLOROPHENYL) THIOL-5-FLUORO-24-DIMETHYL-LH-INDOLE-L-ACETIC] acid; [I) 7-CHLORO-5-FLUORO-2, 4-DIMETHYL-3-METHYLTHIO-LH-INDOLE] A stirred solution of 2-chloro-4-fluoro-5-methylaniline (1.65 g) in methylene chloride (100 ml) under nitrogen was treated [AT-65°C] with a solution [OF T-BUTYL] hypochlorite (1.13 g) in methylene chloride (5 ml), stirred [AT-65°C] for 10 min, treated [AT-65°C] with a solution of methylthioacetone (1. 080 g) in methylene chloride (5 ml) stirred [AT-65°C] for [1] hour, treated [AT-65°C] with triethylamine (1. 05 g) and allowed to reach ambient temperature. The solution was washed, dried [(MGS04)] and evaporated. The residue was purified by silica chromatography using 25% acetone in isohexane as eluent to give the title compound (1.7 g). MS: APCI- [M-H] 242 [1H NMR DMSO-D6] : [8] 11.67 [(1H,] s), 7.07 [(1H,] d), 2.71 (3H, d), 2. [48] (3H, s), 2.19 (3H, s).
  • 6
  • [ 124185-35-9 ]
  • [ 2042171-00-4 ]
  • [ 2042168-00-1 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 4-[(pyrazolo[1,5-a]pyrimidin-3-ylcarbonyl)amino]bicyclo[2.2.2]octane-1-carboxylic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-4-fluoro-5-methylaniline With pyridine In dichloromethane at 20℃; 118 N-{4-[(2-chloro-4-fluoro-5-methylphenyl)carbamoyl]bicyclo[2.2.2]oct-1-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide 1-Chlor-1-dimethylamino-2-methyl-1-propen (70.1 mg, 0.525 mmol) was added to a 4-[(pyrazolo[1 ,5-a]pyrim idin-3-ylcarbonyl)am ino]bicyclo[2.2.2]octane-1 -carboxylic acid (55.0 mg, 0.175 mmol,) in dichloromethane (3.3 ml) and the mixture was stirred at room temperature for 30 mi Pyridine (71 p1, 0.875 mmol) and 2-chloro-4-fluoro-5-methylaniline (55.8 mg, 0.350 mmol, GAS No. 1241 85-35-9)were added and the mixture was stirred over night at room temperature. For work-up the reaction mixture was concentrated and theresidue was purified by preparative HPLG (Method 8) to yield the title compound (55.5 mg,69% yield).LG-MS (Method 1): R = 1 .20 mm; MS (ESIpos) m/z = 456.3 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.32 (dd, 1H), 9.01 (5, 1H), 8.81 (dd, 1H), 8.53 (5,1H), 7.71 (5, 1H), 7.42 (d, 1H), 7.34 (d, 1H), 7.27 (dd, 1H), 2.21 (d, 3H), 2.09-1.90 (m, 12H).
  • 7
  • [ 124185-35-9 ]
  • [ 2042171-05-9 ]
  • [ 2042168-32-9 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: trans-4-[(pyrazolo[1,5-a]pyrimidin-3-ylcarbonyl)amino]cyclohexanecarboxylic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-4-fluoro-5-methylaniline With pyridine In dichloromethane at 20 - 40℃; 150 N-{trans-4-[(2-chloro-4-fluoro-5-methylphenyl)carbamoyl]cyclohexyl}pyrazolo[1,5-a]pyrimidine-3-carboxamide 1-Chlor-1-dimethylamino-2-methyl-1-propen (139 mg, 1.04 mmol) was added to a solution oftrans-4-[(pyrazolo[1 ,5-a]pyrim idin-3-ylcarbonyl)amino]cyclohexanecarboxylic acid (100 mg,0.347 mmol) in dichloromethane (6.6 ml) and the mixture was stirred at room temperature for30 mi Pyridine (140 p1, 1.7 mmol) and 2-chloro-4-fluoro-5-methylaniline (111 mg, 0.694mmol, GAS No. 124185-35-9) were added and the mixture was stirred over night at roomtemperature followed by 3 h at 400. For work-up, the reaction mixture was concentratedand the residue was stirred with dimethyl sulfoxide, the precipitated was collected by filtration, washed and dried to yield the title compound (119 mg, 78% yield).LG-MS (Method 2): R = 1 .09 mm; MS (ESIpos) m/z = 430.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.46 (br. s, 1H), 9.32 (dd, 1H), 8.82 (dd, 1H), 8.58(5, 1H), 7.79 (d, 1H), 7.48 (d, 1H), 7.41 (d, 1H), 7.31 -7.24 (m, 1H), 3.92-3.74 (m, 1H), 2.48-2.39 (m, 1H), 2.21 (d, 3H), 2.10-2.00 (m, 2H), 1.99-1.89 (m, 2H), 1.67-1.50 (m, 2H), 1.45-1.30 (m, 2H).
  • 8
  • [ 124185-35-9 ]
  • [ 2042170-50-1 ]
  • [ 2042170-74-9 ]
YieldReaction ConditionsOperation in experiment
445 mg Stage #1: trans-4-([4-(phenoxycarbonyl)-1H-imidazol-5-yl]carbonyl}amino)cyclohexanecarboxylic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-4-fluoro-5-methylaniline With pyridine In dichloromethane at 20℃; I25 phenyl 5-({trans-4-[(2-chloro-4-fluoro-5-methylphenyl)carbamoyl]cyclohexyl}carbamoyl)-1H-imidazole-4-carboxylate i-Chloro-N,N,2-trimethylprop-i -en-i-amine (748 mg, 5.60 mmol) was added to a solution of trans-4-([4-(phenoxycarbonyl)-i H-im idazol-5-yl]carbonyl}am ino)cyclohexanecarboxylic acid (i.00 g, 2.80 mmol) in dichloromethane (63 ml) and the mixture was stirred at room temperature for 30 mi Pyridine (0.68 ml, 8.4 mmol) and 2-chloro-4-fluoro-5-methylaniline(49i mg, 3.08 mmol, GAS No. i24i85-35-9) were added an the mixture was stirred over night at room temperature. For work-up, water was added, the mixture was extracted with ethyl acetate and the organic phase was washed with a saturated sodium bicarbonate solution and water. The organic phase was dired by filtration through a silicone filter and the filtrate was concentrated. The crude product was stirred with methanol. The precipitate wascollected by filtration, washed with methanol and dried to yield the title compound (445 mg, 32% yield).LG-MS (Method 6): R = i .i 8 mm; MS (ESIpos) m/z = 499.i [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = i3.57 (br. s., iH), 9.46-9.30 (m, 2H), 7.94 (5, iH),7.54-7.43 (m, 3H), 7.43-7.24 (m, 4H), 3.80-3.65 (m, iH), 2.44-2.35 (m, iH), 2.20 (d, 3H),2.06-i .82 (m, 4H), i.63-i.i9 (m, 4H).
  • 9
  • [ 124185-35-9 ]
  • [ CAS Unavailable ]
  • [ 2042172-90-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-chloro-4-fluoro-5-methylaniline With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -70℃; for 1h; Stage #2: ethyl 4-[tert-butyl(diphenyl)silyl]oxy}-1-(3-chloropropyl)cyclohexanecarboxylate In tetrahydrofuran at -78 - 20℃; for 121.008h; I149 9-[tert-butyl(diphenyl)silyl]oxy}-2-(2-chloro-4-fluoro-5-methylphenyl)-2-azaspiro[5.5]undecan-1-one (isomer 1) Lithium bis(trimethylsilyl)amide (46 ml, 1 .0 M in THE, 46 mmol) was added during 5 minutes drop wise to a solution of 2-chloro-4-fluoro-5-methylaniline (4.05 g, 25.4 mmol, CAS No1241 85-35-9) in tetrahydrofuran (250 ml) at 50% ethyl acetate) to give the title compound (6.69 g, based on 1H NMR predominantly, isomer 1, contains 2-chloro-4-fluoro-5-methylaniline as an impurity).1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 1.035 (1.68), 1.043 (16.00), 1.201 (1.36), 1.219(0.68), 2.016 (2.18), 2.119 (0.88), 2.124 (0.93), 2.248 (3.05), 2.251 (3.04), 7.332 (0.80),7.352 (0.81), 7.443 (2.42), 7.462 (2.66), 7.469 (2.00), 7.473 (1.17), 7.485 (2.50), 7.508(1.29), 7.616 (1.72), 7.618 (2.20), 7.620 (2.14), 7.622 (1.84), 7.635 (1.96), 7.638 (1.92),7.641 (1.10).
  • 10
  • [ 124185-35-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-chloro-4-fluoro-5-methylaniline With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: ethyl 4-[tert-butyl(diphenyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate In tetrahydrofuran at -78 - 20℃; for 97.992h; I136 8-[tert-butyl(diphenyl)silyl]oxy}-2-(2-chloro-4-fluoro-5-methylphenyl)-2-azaspiro[4.5]decan-1-one(mixture of cis-Itrans-isomers) Lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (42 ml, 1 M solution in tetrahyrofuran, 42 mmol, GAS No 4039-32-1) was added drop wise within 5 minutes to a solution of 2-chloro-4- fluoro-5-methylaniline (3.79 g, 23.2 mmol, GAS No 124185-35-9) in tetrahydrofuran (110 ml) at -78G. The mixture was stirred for 30 mm at that temperature. A solution of ethyl 4-[tert-butyl(diphenyl)silyl]oxy}-1 -(2-chloroethyl)cyclohexanecarboxylate (mixture of cis/trans isomers) (10.0 g, 21.1 mmol) in tetrahydrofuran (110 ml) was added and the mixture was stirred for 2 h at -78G. The mixture was warmed to room temperature and stirred for 4 d. For work-up, the reaction was added to a solution of water and sodium bicarbonate and the mixture was extracted with ethyl acetate (3x). The combined organic phases were washedwith sodium chloride, dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by flash chromatography (1 00 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 30% ethyl acetate) the product containing fractions were concentrated and were then purified a second time by flash chromatography (120 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 40% ethyl acetate to give the title compoundin 2 fractions: fraction 1(5.85 g, single isomer based on 1H NMR, isomer 1), fraction 2(1.21 g, single isomer based on 1H NMR, isomer 2).Fraction 1 (isomer 1):1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 7.65-7.58 (m, 4H), 7.52-7.34 (m, 8H), 3.96 (br s,1 H), 3.56 (t, 2H), 2.23 (d, 3H), 2.09 (td, 2H), 2.04-1 .99 (m, 2H), 1 .72-1 .59 (m, 2H), 1 .56-1 .45(m, 2H), 1.31 (m, 2H), 1.04 (5, 9H).Fraction 2 (isomer 2): 1H-NMR (400 MHz, DMSO-d6) 6 [ppm] = 7.66-7.59 (m, 4H), 7.50-7.41(m, 7H), 7.33 (d, 1H), 3.70-3.60 (m, 1H), 3.58-3.52 (m, 2H), 2.20 (d, 3H), 2.07 (t, 2H), 1.77(br dd, 2H), 1.58-1.33 (m, 6H), 1.02 (5, 9H).
Stage #1: 2-chloro-4-fluoro-5-methylaniline With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: ethyl 4-[tert-butyl(diphenyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate In tetrahydrofuran at -78 - 20℃; for 96h; 3 8-[tert-butyl(diphenyl)silyl]oxy}-2-(2-chloro-4-fluoro-5-methylphenyl)-2-azaspiro[4.5]decan-1-one (mixture of cis/trans-isomers) Lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (42 ml, 1 M solution in tetrahyrofuran, 42 mmol,CAS No 4039-32-1 ) was added drop wise within 5 minutes to a solution of 2-chloro-4-fluoro-5-methylaniline (3.79 g, 23.2 mmol, CAS No 124185-35-9) in tetrahydrofuran (1 10 ml) at -78. The mixture was stirred for 30 min at that temperature. A solution of ethyl 4-[tert-butyl(diphenyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate (mixture of cis/trans isomers) (10.0 g, 21 .1 mmol) in tetrahydrofuran (1 10 ml) was added and the mixture was stirred for 2 h at -78. The mixture was warmed to room temperatur e and stirred for 4 d. For work-up, the reaction was added to a solution of water and sodium bicarbonate and the mixture was extracted with ethyl acetate (3x). The combined organic phases were washed with sodium chloride, dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by flash chromatography (100 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 30% ethyl acetate) the product containing fractions were concentrated and were then purified a second time by flash chromatography (120 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 40% ethyl acetate to give the title compound in 2 fractions: fraction 1 (5.85 g, single isomer based on1H NMR, isomer 1 ), fraction 2 (1 .21 g, single isomer based on1H NMR, isomer 2).Fraction 1 (isomer 1 ):1H-NMR (400 MHz, DMSO-de): δ [ppm] = 7.65-7.58 (m, 4H), 7.52-7.34 (m, 8H), 3.96 (br s, 1H), 3.56 (t, 2H), 2.23 (d, 3H), 2.09 (td, 2H), 2.04-1 .99 (m, 2H), 1 .72-1 .59 (m, 2H), 1 .56-1 .45 (m, 2H), 1.31 (m, 2H), 1.04 (s, 9H).Fraction 2 (isomer 2):1H-NMR (400 MHz, DMSO-d6) δ [ppm] = 7.66-7.59 (m, 4H), 7.50-7.41 (m, 7H), 7.33 (d, 1H), 3.70-3.60 (m, 1H), 3.58-3.52 (m, 2H), 2.20 (d, 3H), 2.07 (t, 2H), 1 .77 (br dd, 2H), 1 .58-1.33 (m, 6H), 1.02 (s, 9H)
  • 11
  • [ 124185-35-9 ]
  • [ 2042172-77-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux
  • 12
  • [ 124185-35-9 ]
  • [ 2042172-78-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C
  • 13
  • [ 124185-35-9 ]
  • [ 2042172-79-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C
  • 14
  • [ 124185-35-9 ]
  • [ 2042172-80-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C
  • 15
  • [ 124185-35-9 ]
  • [ 2042172-81-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C
  • 16
  • [ 124185-35-9 ]
  • [ 2042169-47-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 20 °C
  • 17
  • [ 124185-35-9 ]
  • [ 2042169-48-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 20 °C
  • 18
  • [ 124185-35-9 ]
  • [ 2042169-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 20 °C
  • 19
  • [ 124185-35-9 ]
  • [ 2042169-70-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: tetrahydrofuran / 20 h / 20 °C
  • 20
  • [ 124185-35-9 ]
  • [ 2042169-71-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: tetrahydrofuran / 20 h / 20 °C
  • 21
  • [ 124185-35-9 ]
  • [ 2042169-72-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: tetrahydrofuran / 20 h / 20 °C
  • 22
  • [ 124185-35-9 ]
  • [ 2042169-73-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: ammonia / tetrahydrofuran / 91.92 h / 50 - 80 °C
  • 23
  • [ 124185-35-9 ]
  • [ 2042169-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: triethylamine / tetrahydrofuran / 20 h / 50 °C
  • 24
  • [ 124185-35-9 ]
  • [ 2042169-75-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: triethylamine / tetrahydrofuran / 91.92 h / 50 °C
  • 25
  • [ 124185-35-9 ]
  • [ 2042169-76-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: tetrahydrofuran / 21 h / 50 °C
  • 26
  • [ 124185-35-9 ]
  • [ 2042169-77-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: tetrahydrofuran / 21 h / 50 °C
  • 27
  • [ 124185-35-9 ]
  • [ 2042169-78-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: triethylamine / tetrahydrofuran / 91.92 h / 50 °C
  • 28
  • [ 124185-35-9 ]
  • [ 2042169-79-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: pyridine / tetrahydrofuran / 1.5 h / 130 - 170 °C / Microwave irradiation
  • 29
  • [ 124185-35-9 ]
  • [ 2042170-15-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 97.99 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Reflux 3.1: triethylamine / dichloromethane / 1 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 5.5 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; water / 17 h / 20 - 50 °C 6.1: triethylamine / tetrahydrofuran / 15 h / 20 °C 7.1: tetrahydrofuran / 20 h / 20 °C
  • 30
  • [ 124185-35-9 ]
  • [ 628736-92-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C
  • 31
  • [ 124185-35-9 ]
  • [ 628736-91-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C
  • 32
  • [ 124185-35-9 ]
  • [ 628736-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux
  • 33
  • [ 124185-35-9 ]
  • [ 628736-94-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water
  • 34
  • [ 124185-35-9 ]
  • [ 628736-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine / DMF (N,N-dimethyl-formamide)
  • 35
  • [ 124185-35-9 ]
  • [ 628736-97-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine
  • 36
  • [ 124185-35-9 ]
  • [ 628736-96-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine
  • 37
  • [ 124185-35-9 ]
  • [ 628736-99-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine
  • 38
  • [ 124185-35-9 ]
  • [ 628736-98-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine
  • 39
  • [ 124185-35-9 ]
  • [ 628736-95-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine
  • 40
  • [ 124185-35-9 ]
  • [ 628737-00-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert-butylhypochlorite / dichloromethane / 0.17 h / -65 °C / Nitrogen atmosphere 1.2: 1 h / -65 °C / Nitrogen atmosphere 1.3: -65 - 20 °C 2.1: thiosalicilyc acid; trifluoroacetic acid / 2 h / 60 °C 3.1: palladium 10% on activated carbon / ethanol; water / 0.02 h 3.2: 50 h / 40 °C 4.1: caesium carbonate / acetone / 2 h / Heating / reflux 5.1: lithium hydroxide / tetrahydrofuran; water 6.1: iodine
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