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[ CAS No. 611-33-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 611-33-6
Chemical Structure| 611-33-6
Chemical Structure| 611-33-6
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Product Details of [ 611-33-6 ]

CAS No. :611-33-6 MDL No. :MFCD00047618
Formula : C9H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :RUSMDMDNFUYZTM-UHFFFAOYSA-N
M.W : 163.60 Pubchem ID :69139
Synonyms :

Calculated chemistry of [ 611-33-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.75
TPSA : 12.89 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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 2.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.141 mg/ml ; 0.000862 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.724 mg/ml ; 0.00443 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.31
Solubility : 0.00807 mg/ml ; 0.0000493 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 611-33-6 ]

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 [ 611-33-6 ]

* 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.

  • Upstream synthesis route of [ 611-33-6 ]
  • Downstream synthetic route of [ 611-33-6 ]

[ 611-33-6 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 4470-83-1 ]
  • [ 611-33-6 ]
YieldReaction ConditionsOperation in experiment
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 6 h; Inert atmosphere General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 molpercent), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
  • 2
  • [ 95-51-2 ]
  • [ 56-81-5 ]
  • [ 611-33-6 ]
YieldReaction ConditionsOperation in experiment
70% Microwave irradiation General procedure: A mixture of aromatic amine (1.0 mmol), glycerol (3.0 mmol), and Brönsted acidic ionic liquid BAIL (1.5 mmol) in a closed glass vial was heated using a GE model JE635WW microwave oven, at full power (920W) in five 20 s pulses giving 5 s cooling time between the pulses. Then cooled reaction mixture was diluted with water (30 mL), basified with 0.5 M aqueous sodium hydroxide and steam distilled. The distillate was extracted with methylene chloride (3X 6 mL). Combined organic layer was dried and chromatographed on silica, eluting with methylene chloride gave corresponding quinolines.
Reference: [1] Organic Letters, 2011, vol. 13, # 15, p. 4024 - 4027
[2] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3319 - 3321
[3] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
[4] Bulletin de la Societe Chimique de France, 1930, vol. <4> 47, p. 749
[5] Journal of the Chemical Society, 1943, p. 419
[6] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 140
[7] Ing. Chimiste Bruessel, 1936, vol. 20, p. 204,207
  • 3
  • [ 90562-36-0 ]
  • [ 611-33-6 ]
YieldReaction ConditionsOperation in experiment
72% With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen In N,N-dimethyl-formamide for 15 h; General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for 1H and 100 MHz for 13C, using CDCl3 as solvent with TMS as the internal standard. Thin-layer chromatography was performed on silica gel 60 F254 (Sinopharm) thin-layer chromatography plates using petroleum ether/ethyl acetate (10:1 v/v) as the mobile phase.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[2] Tetrahedron, 1996, vol. 52, # 10, p. 3705 - 3718
[3] ChemCatChem, 2017, vol. 9, # 13, p. 2463 - 2466
  • 4
  • [ 95-51-2 ]
  • [ 504-63-2 ]
  • [ 611-33-6 ]
YieldReaction ConditionsOperation in experiment
57% at 150℃; for 8 h; Inert atmosphere; Sealed tube General procedure: An ampule was charged with 0.02 mmol of FeCl3·6H2O, 2 mmol of aniline, 4 mmol of carbon tetrachloride, and 8 mmol 1,3-propanediol under argon. The sealed ampule was placed into a pressure reactor, which was hermetically closed and heated at 150°C for 8 h with continuous stirring. After the reaction completion, the reactor was cooled to room temperature, the ampule was opened, the reaction mixture was poured in hydrochloric acid. The aqueous layer was separated, neutralized with 10percent sodium hydroxide solution, and extracted with methylenechloride. The organic layer was filtered, the solvent was distilled off, and the residue was distilled in a vacuum. Physicochemical characteristics and spectral data of the obtained compounds 2a–2l corresponded to the literature data.
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
[3] Journal of Organic Chemistry, 1987, vol. 52, # 9, p. 1673 - 1680
  • 5
  • [ 3054-95-3 ]
  • [ 95-51-2 ]
  • [ 611-33-6 ]
YieldReaction ConditionsOperation in experiment
32.1 %Chromat. With Ni-modified Beta zeolite In neat (no solvent) for 0.0833333 h; Microwave irradiation; Reflux; Green chemistry General procedure: General procedure for synthesis of quinolines from anilines and ADA was carried out in Panasonic NN-K5541JF microwave oven reactor equipping a magnetic stirring device. The typical procedures were as follows: ADA (1mmol), excessive anilines (4mmol) and solid catalyst were charged into a round-bottom ask; and then, the mixtures was placed into microwave reactor. The reaction was conducted by continuous microwave irradiation for 1–40 min under refluxing and stirring condition. Finally, the resulting products were determined by GC–MS of Varian Saturn 2200/ CP-3800 gas chromatography–mass spectrometry equipped with two CP8944 capillary columns (VF-5,30m×0.25mm×0.25 μm).
Reference: [1] Catalysis Communications, 2018, vol. 115, p. 21 - 25
  • 6
  • [ 137-04-2 ]
  • [ 56-81-5 ]
  • [ 611-33-6 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 38, p. 9042 - 9051
  • 7
  • [ 154519-62-7 ]
  • [ 611-33-6 ]
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782
  • 8
  • [ 42606-39-3 ]
  • [ 1338952-12-7 ]
  • [ 1338952-14-9 ]
  • [ 611-33-6 ]
Reference: [1] ChemMedChem, 2011, vol. 6, # 10, p. 1872 - 1883
  • 9
  • [ 1074-06-2 ]
  • [ 611-33-6 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 10, p. 3705 - 3718
  • 10
  • [ 176097-81-7 ]
  • [ 611-33-6 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 10, p. 3705 - 3718
  • 11
  • [ 3900-89-8 ]
  • [ 611-33-6 ]
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782
  • 12
  • [ 95-51-2 ]
  • [ 611-33-6 ]
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782
  • 13
  • [ 611-33-6 ]
  • [ 4470-83-1 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 38, p. 9042 - 9051
  • 14
  • [ 611-33-6 ]
  • [ 90562-36-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 6, p. 933 - 940
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3216 - 3220[3] Angew. Chem., 2017, vol. 129, # 12, p. 3264 - 3268,5
[4] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 1981 - 1985
[5] Chemical Communications, 2018, vol. 54, # 62, p. 8622 - 8625
[6] Chemistry - A European Journal, 2016, vol. 22, # 48, p. 17151 - 17155
[7] Patent: WO2005/821, 2005, A1, . Location in patent: Page 58-59
[8] Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9419 - 9422
[9] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
  • 15
  • [ 611-33-6 ]
  • [ 607742-69-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3884 - 3890
  • 16
  • [ 611-33-6 ]
  • [ 847727-21-3 ]
YieldReaction ConditionsOperation in experiment
69% With N-iodo-succinimide In acetic acid at 70℃; for 18 h; N-LODOSUCCINIMIDE (67.9 g, 0.30 MMOL) was added in portions to a stirred solution of 8- chloroquinoline (49 g, 0.30 MMOL) (J. Org. CHEM., 1987,52, 1673-80) in acetic acid (300 ml) at 70 °C under argon. The mixture was heated to 70 °C for 18 h and then CONCENTRATED IN VACUO. The residue was redissolved in DICHLOROMETHANE (600 ml) and the solution was washed successively with 10percent aqueous sodium thiosulfate solution (2 x 300 ML) and 10percent aqueous sodium hydrogen carbonate solution (2 x 300 ML), dried (MGS04) and CONCENTRATED IN VACUO to a solid. The solid was recrystallised from ethyl acetate to afford the title compound (D1) as a yellow solid (42 g, 0.145 mol, 48percent). The residue from recrystallisation was purified by chromatography over silica gel eluting with a toluene/acetone gradient to afford a second crop of the product (18 g, total yield 69percent). SH (CDC13) 7.49 (1H, t, J = 8. 1HZ), 7.65 (1H, dd, J = 1.4Hz, 8.3Hz), 7.85 (1H, dd, J = 1.3Hz, 7.4Hz), 8.57 (1H, d, J = 2. 1 Hz), 9.15 (1 H, D J = 2. 1 HZ). Mass Spectrum: C9H5CIIN requires 289,291 ; found 290,292 (MH+)
69%
Stage #1: With N-iodo-succinimide In acetic acid at 70℃; for 18 h;
Stage #2: With sodium hydrogencarbonate In water
Description 1 8-CHLORO-3-IODOQUINOLINE (D1) N-lodosuccinimide (67.9 g, 0.30 MMOL) was added in portions to a stirred solution of 8- CHLOROQUINOLINE (49 g, 0.30 MMOL) (J. Org. Chem. , 1987,52, 1673-80) in acetic acid (300 ml) at 70 °C under argon. The mixture was heated to 70 °C for 18 h and then concentrated in vacuo. The residue was REDISSOLVED in dichloromethane (600 ml) and the solution was washed successively with 10percent aqueous sodium thiosulfate solution (2 x 300 ml) and 10percent aqueous sodium hydrogen carbonate solution (2 x 300 ML), dried (MGS04) and concentrated in vacuo to a solid. The solid was recrystallised from ethyl acetate to afford the title compound (D1) as a yellow solid (42 g, 0.145 mol, 48percent). The residue from recrystallisation was purified by chromatography over silica gel eluting with a TOLUENE/ACETONE gradient to afford a second crop of the product (18 g, total yield 69percent).
45% at 40 - 65℃; for 23 h; Description 10; 8-Chloro-3-iodoquinoline (D10); N-lodosuccinimide (206.3g, 0.92mol) was added portionwise over 1 h to a stirred solution of 8-chloroquinoline (15Og, 0.92mol) in acetic acid (750ml) at 4O0C. The reaction temperature was then increased to 650C and this was maintained for 18h after which another portion of N-iodosuccinimide (61.9g, 0.28mmol) was added. After a further 4h at this temperature, the mixture was cooled to ambient temperature and evaporated in vacuo to an oil. The oil was dissolved in dichloromethane (600ml) and the solution was washed with saturated sodium thiosulfate solution (2 x 400ml), dried (MgSO4) and EPO <DP n="31"/>concentrated in vacuo to a solid (28Og). The solid was recrystallized from ethyl acetate (300ml) to afford the title compound (D10) as a yellow solid (8Og). Concentration of the corresponding filtrate gave a second crop of title compound (3Og, total yield 45percent). Mass Spectrum C9H5 CIIN requires 289; found 290 (MH+).
45% at 40 - 65℃; for 23 h; Description 3; 8-Chloro-3-iodoquinoline (D3); N-lodosuccinimide (206.3 g, 0.92 mol) was added portionwise over 1 h to a stirred solution of 8-chloroquinoline (150 g, 0.92 mol) in acetic acid (750 ml) at 40°C. The reaction temperature was then increased to 65°C and this was maintained for 18 h after which another portion of N-iodosuccinimide (61.9 g, 0.28 mmol) was added. After a further 4 h at this temperature, the mixture was cooled to ambient temperature and evaporated in vacuo to an oil. The oil was dissolved in dichloromethane (600 ml) and the solution was washed with saturated sodium thiosulfate solution (2 x 400 ml), dried (MgS04) and concentrated in vacuo to a solid (280 g). The solid was recrystallized from ethyl acetate (300 ml) to afford the title compound (D3) as a yellow solid (80 g). Concentration of the corresponding filtrate gave a second crop of title compound (30 g, total yield 45percent). MS: m/z (M+H)@ C9H5CIIN requires 289,291; found 290,292 (MH+).
45% With N-iodo-succinimide In acetic acid at 40 - 65℃; for 23 h; N-Iodosuccinimide (206 3g, 0 92mol) was added portionwise over Ih to a stirred solution of 8-chloroquinoline (15Og, 0 92mol) in acetic acid (750ml) at 400C The reaction temperature was then increased to 650C and this was maintained for 18h after which another portion of N- iodosuccinimide (61 9g, 0 28mmol) was added After a further 4h at this temperature, the mixture was cooled to ambient temperature and evaporated in vacuo to an oil The oil was dissolved in dichloromethane (600ml) and the solution was washed with saturated sodium thiosulfate solution (2 x 400ml), dried (MgSO/i) and concentrated in vacuo to a solid (28Og). The solid was recrystallized from ethyl acetate (300ml) to afford the title compound as a yellow solid (80g). Concentration of the corresponding filtrate gave a second crop of title compound (30g, total yield 45percent). Mass Spectrum C9H5 ClIN requires 289, found 290 (MH+).

Reference: [1] Organic Letters, 2015, vol. 17, # 18, p. 4408 - 4411
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3884 - 3890
[3] Patent: WO2005/21530, 2005, A1, . Location in patent: Page/Page column 12
[4] Patent: WO2005/30724, 2005, A1, . Location in patent: Page/Page column 10-11
[5] Patent: WO2007/39219, 2007, A1, . Location in patent: Page/Page column 29-30
[6] Patent: WO2005/113539, 2005, A1, . Location in patent: Page/Page column 11
[7] Patent: WO2008/116816, 2008, A1, . Location in patent: Page/Page column 190
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 38, p. 10204 - 10208[9] Angew. Chem., 2014, vol. 126, # 38, p. 10368 - 10372,5
[10] Chemical Science, 2018, vol. 9, # 12, p. 3186 - 3191
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