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[ CAS No. 516-12-1 ]

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Chemical Structure| 516-12-1
Chemical Structure| 516-12-1
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Product Details of [ 516-12-1 ]

CAS No. :516-12-1 MDL No. :MFCD00005512
Formula : C4H4INO2 Boiling Point : 249.6±23.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :224.98 g/mol Pubchem ID :120273
Synonyms :

Safety of [ 516-12-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 516-12-1 ]

  • Upstream synthesis route of [ 516-12-1 ]
  • Downstream synthetic route of [ 516-12-1 ]

[ 516-12-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 123-56-8 ]
  • [ 516-12-1 ]
YieldReaction ConditionsOperation in experiment
99% With [bis(acetoxy)iodo]benzene; iodine In benzene at 20℃; for 15 h; Darkness [00172] A mixture of succinimide (1.0 g, 10.1 mmol), PhI(OAc)2 (1.95 g, 6.06 mmol), I2 (1.67 g, 6.57 mmol) and benzene (20 mL) was stirred for 15 h at rt and for 1 h at 0 to 5 °C. The precipitated solid was filtered, washed on the filter with cold benzene and dried in vacuo to give 2.2 g (99percent) of N-iodosuccinimide.
Reference: [1] Patent: WO2015/68159, 2015, A2, . Location in patent: Paragraph 00171-00172
[2] Journal of Organometallic Chemistry, 1983, vol. 255, # 3, p. 295 - 298
  • 2
  • [ 128-09-6 ]
  • [ 516-12-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 29, p. 6264 - 6268
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 18, p. 3119 - 3125
[3] Tetrahedron Letters, 1984, vol. 25, # 2, p. 233 - 236
[4] Journal of Organic Chemistry, 2007, vol. 72, # 8, p. 2978 - 2987
[5] Journal of Organic Chemistry, 2016, vol. 81, # 9, p. 3868 - 3876
  • 3
  • [ 128-08-5 ]
  • [ 516-12-1 ]
Reference: [1] Russian Journal of Organic Chemistry, 2001, vol. 37, # 10, p. 1503 - 1504
[2] Journal of the American Chemical Society, 2018, vol. 140, # 19, p. 6039 - 6043
[3] Russian Journal of Organic Chemistry, 2018, vol. 54, # 1, p. 131 - 138[4] Zh. Org. Khim., 2018, vol. 54, # 1, p. 131 - 138,8
  • 4
  • [ 123-56-8 ]
  • [ 7553-56-2 ]
  • [ 67-64-1 ]
  • [ 516-12-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1870, vol. Suppl.7, p. 119
  • 5
  • [ 516-12-1 ]
  • [ 3680-69-1 ]
  • [ 123148-78-7 ]
YieldReaction ConditionsOperation in experiment
86.9% at 20℃; Step 1:4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10percent solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6percent) of the title compound as off-white crystals. The mother liquid was evaporated up to volume and crystallized again from ethanol to give 2.47 g (12.3percent) of the target compound. The total yield is close to 100percent;Tm 212-214° C. (dec);UV λmax: 307, 266, 230, 227 nm (methanol);MS: 277.93 (M-H), 313 (M+Cl);1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H), 7.94 (s, 1H).
Reference: [1] Patent: US2009/48189, 2009, A1, . Location in patent: Page/Page column 36
  • 6
  • [ 516-12-1 ]
  • [ 1885-29-6 ]
  • [ 132131-24-9 ]
YieldReaction ConditionsOperation in experiment
73% at 20℃; for 18 h; N-iodosuccinimide (11.35 g, 50.4 mmol) was added in several portions at room temperature to a solution of anthranilonitrile (Aldrich, 5.87 g, 49.7 mmol) in DMF (80 mL) and stirred under N2 for 18 h. The reaction mixture was concentrated to [1/4] volume and diluted with [H20] (200 mL) and [CH2C12.] The phases were separated. The organic phase was washed with H2O, dried [(NA2SO4),] and concentrated in vacuo to give 14 g of dark liquid that was dissolved in hot ethanol and diluted with ca. 100 mL of hot H2O. The solution was cooled to room temperature overnight. The crystallized mixture was filtered and the pink mica-like sheets were washed with [H20] and dried in a vacuum oven at [40 C] to give 8. 85 g (73percent) of product; mp [76-78 C] : MS (EI) [INTO] (rel. intensity) 244 (M+, 99), 245 (12), 127 (9), 118 (9), 117 (72), 90 (75), 84 (11), 64 (14), 63 (42), 62 (13).
Reference: [1] Patent: WO2004/18461, 2004, A2, . Location in patent: Page 40-41
  • 7
  • [ 516-12-1 ]
  • [ 2380-63-4 ]
  • [ 151266-23-8 ]
YieldReaction ConditionsOperation in experiment
86% at 80℃; for 12 h; Pyrazolo [3,4-d] pyrimidin-4-amine (15.0 g, 111.1 mmol) was dissolved in DMF (150 mL) N-iodosuccinimide (37.5 g, 166. 6 mmol) was slowly added to the reaction mixture, and the reaction was stirred at 80 ° C for 12 h. stopWater (40 mL) was added to the reaction mixture, and the mixture was suction filtered. The solid was washed with water (80 mL), ethanol (60 mL) and dried to give to a yellow solid (24. 9 g, 86percent).
Reference: [1] Patent: CN105399756, 2016, A, . Location in patent: Paragraph 0155; 0165-0166
[2] Patent: CN105859728, 2016, A, . Location in patent: Paragraph 0073; 0074
  • 8
  • [ 516-12-1 ]
  • [ 873-74-5 ]
  • [ 33348-34-4 ]
Reference: [1] Patent: WO2009/78983, 2009, A1, . Location in patent: Page/Page column 80
  • 9
  • [ 274-76-0 ]
  • [ 516-12-1 ]
  • [ 307503-19-1 ]
YieldReaction ConditionsOperation in experiment
45.5% at 20℃; for 1 h; To thesolution of imidazo[1,2-a]pyridine (6.50 g, 0.055 mol) in 80mLof THF was added 1-iodopyrrolidine-2,5-dione (14.85 g,0.066 mol) slowly. The reaction mixture was stirred for 1 h atroom temperature and extracted by ethyl acetate. The organicphase was collected and the solvent was evaporated to affordthe yellow solid (6.10 g, 45.5percent).
Reference: [1] Chemistry Letters, 2017, vol. 46, # 6, p. 848 - 850
  • 10
  • [ 516-12-1 ]
  • [ 875781-17-2 ]
  • [ 875781-18-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 879 - 894
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