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[ CAS No. 847727-21-3 ]

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2D
Chemical Structure| 847727-21-3
Chemical Structure| 847727-21-3
Structure of 847727-21-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 847727-21-3 ]

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Related Doc. of [ 847727-21-3 ]

SDS

Product Details of [ 847727-21-3 ]

CAS No. :847727-21-3MDL No. :MFCD11044980
Formula :C9H5ClINBoiling Point :354.8±22.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :CLABEFPWOLGBAP-UHFFFAOYSA-N
M.W :289.50Pubchem ID :53438635
Synonyms :

Computed Properties of [ 847727-21-3 ]

TPSA : 12.9 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 847727-21-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 847727-21-3 ]

  • Upstream synthesis route of [ 847727-21-3 ]
  • Downstream synthetic route of [ 847727-21-3 ]

[ 847727-21-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 611-33-6 ]
  • [ 847727-21-3 ]
YieldReaction ConditionsOperation in experiment
69% With N-iodo-succinimide In acetic acid at 70℃; for 18.00 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 18.00 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 23.00 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 23.00 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 23.00 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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