[ CAS No. 516-12-1 ]

Name: 516-12-1|1-Iodopyrrolidine-2,5-dione|98%
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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 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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;T_m212-214° C. (dec);UV λ_max: 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 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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

[ 516-12-1 ] Synthesis Path-Downstream 1~25

1
[ 123-56-8 ]
[ 516-12-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [bis(acetoxy)iodo]benzene; iodine; In benzene; at 20℃; for 15h;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,p. 295 - 298

2
[ 128-09-6 ]
[ 516-12-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6264 - 6268
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 3119 - 3125
[3]Tetrahedron Letters,1984,vol. 25,p. 233 - 236
[4]Journal of Organic Chemistry,2007,vol. 72,p. 2978 - 2987
[5]Journal of Organic Chemistry,2016,vol. 81,p. 3868 - 3876

3
[ 516-12-1 ]
[ 82621-86-1 ]

Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 6576 - 6584
[2]Journal of the American Chemical Society,1985,vol. 107,p. 6584 - 6589

4
[ 516-12-1 ]
[ 22347-71-3 ]
[ 354-38-1 ]
Acetic acid (2R,5R,6R)-6-(2,5-dioxo-pyrrolidin-1-yl)-5-iodo-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]
Acetic acid (2R,5S,6S)-5-iodo-6-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]
Acetic acid (2S,5S,6S)-5-iodo-6-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 2653 - 2656

5
[ 516-12-1 ]
[ 26510-52-1 ]
2-iodo-3-oxo-3-pyridin-2-yl-propionic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 623 - 626

6
[ 516-12-1 ]
2-carbomethoxy-3-(4-tributyltinphenyl)-8-oxabicyclo[3.2.1]-2-octene [ No CAS ]
[ 192461-00-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; at 20℃; for 1h;	EXAMPLE 13 2-Carbomethoxy-3-(4-iodophenyl)-8-oxabicyclo(3.2.1)-2-octene. 2-Carbomethoxy-3-(4-tributyltinphenyl)-8-oxabicyclo(3.2.1)-2-octene (206 mg, 0.39 mmol) in THF (anhydrous, 5 ML) was degassed by bubbling N2 for 10 min. N-Iodo-succinimide (96 mg, 0.43 mmol) was added.. The reaction mixture was stirred at room temperature for 1 h and concentrated to dryness.. The residue was dissolved in ether (10 ML), washed with saturated NaHCO3 and brine.. The dried (MgSo4) ether layer was concentrated to dryness.. The residue was purified by flash chromatography and preparative TLC to afford 128 mg (90percent) of 2-carbomethoxy-3-(4-iodophenyl)-8-oxabicyclo(3.2.1)-2-octene as a pale yellow viscous oil. 1H NMR (CDCl3, 100 MHz): delta 6.75-7.80 (q, 4H), 5.00 (bm, 1H), 4.64 (t, 1H), 3.54 (s, 3H), 2.95 (dd, 1H), 1.55-2.40 (m, 5H).
128 mg (90%)	In tetrahydrofuran;	Example 13 2-Carbomethoxy-3-(4-iodophenyl)-8-oxabicyclo(3.2.1)-2-octene 2-Carbomethoxy-3-(4-tributyltinphenyl)-8-oxabicyclo(3.2.1)-2-octene (206 mg, 0.39 mmol) in THF (anhydrous, 5 mL) was degassed by bubbling N2 for 10 min. N-Iodo-succinimide (96 mg, 0.43 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and concentrated to dryness. The residue was dissolved in ether (10 mL), washed with saturated NaHCO3 and brine. The dried (MgSO4) ether layer was concentrated to dryness. The residue was purified by flash chromatography and preparative TLC to afford 128 mg (90percent) of 2-carbomethoxy-3-(4-iodophenyl)-8-oxabicyclo(3.2.1)-2-octene as a pale yellow viscous oil. 1 H NMR (CDCl3, 100 MHz): delta 6.75-7.80 (q, 4H), 5.00 (bm, 1H) 4.64 (t, 1H), 3.54 (s, 3H), 2.95 (dd, 1H), 1.55-2.40 (m, 5H).

Reference： [1]Patent: US6353105,2002,B1 .Location in patent: Page column 19
[2]Patent: US5948933,1999,A

7
[ 516-12-1 ]
2β-carbomethoxy-3α-(4-tributyltinphenyl)-8-oxabicyclo[3.2.1]octane [ No CAS ]
2β-carbomethoxy-3α-(4-iodophenyl)-8-oxabicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran; at 20℃; for 0.5h;	EXAMPLE 16 2beta-Carbomethoxy-3alpha-(4-iodophenyl)-8-oxabicyclo(3.2.1)octane. 2beta-Carbomethoxy-3alpha-(4-tributyltinphenyl)-8-oxabicyclo(3.2.1)octane (147 mg, 0.275 mmol) and THF (3 ML) was degassed for 10 min. N-Iodosuccinimide (63 mg, 0.28 mmol) was added.. The reaction mixture was stirred at room temperature for 30 min.. After concentration to dryness, the residue was dissolved in ether (50 ML) and washed with saturated NaHCO3, H2O and brine.. The dry (Na2SO4) ether layer was concentrated to dryness.. The residue was purified by flash chromatography to afford 87 mg (85percent) of 2beta-carbomethoxy-3alpha-(4-iodophenyl)-8-oxabicyclo(3.2.1)octane as a white solid, mp. 124-126° C. 1H NMR (CDCl3, 100 MHz): delta 6.8-7.7 (q, 4H), 4.3-4.7 (bd, 2H), 3.6 (s, 3H), 3.2 (dt, 1H), 1.1-2.6 (m, 7H).
87 mg (85%)	In tetrahydrofuran;	Example 16 2beta-Carbomethoxy-3alpha-(4-iodophenyl)-8-oxabicyclo(3.2.1)octane 2beta-Carbomethoxy-3alpha-(4-tributyltinphenyl)-8-oxabicyclo(3.2.1)octane (147 mg, 0.275 mmol) and THF (3 mL) was degassed for 10 min. N-Iodosuccinimide (63 mg, 0.28 mmol) was added. The reaction mixture was stirred at room temperature for 30 min. After concentration to dryness, the residue was dissolved in ether (50 mL) and washed with saturated NaHCO3, H2 O and brine. The dry (Na2 SO4) ether layer was concentrated to dryness. The residue was purified by flash chromatography to afford 87 mg (85percent) of 2beta-carbomethoxy-3alpha-(4-iodophenyl)-8-oxabicyclo(3.2.1)octane as a white solid, mp. 124-126° C. 1 H NMR (CDCl3, 100 MHz): delta 6.8-7.7 (q, 4H), 4.3-4.7 (bd, 2H), 3.6 (s, 3H), 3.2 (dt, 1H), 1.1-2.6 (m, 7H).

Reference： [1]Patent: US6353105,2002,B1 .Location in patent: Page column 20
[2]Patent: US5948933,1999,A

8
[ 516-12-1 ]
[ 1885-29-6 ]
[ 132131-24-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	In DMF (N,N-dimethyl-formamide); at 20℃; for 18h;	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 (73%) 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

9
[ 516-12-1 ]
[ 120068-79-3 ]
[ 188539-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	PREPARATION 1 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole N-Iodosuccinimide (3.52 g) was added in portions, over 5 minutes, to a stirred solution of <strong>[120068-79-3]5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole</strong> (EP-A-0295117; 5.0 g) in acetonitrile (60 ml) at room temperature. After being stirred for 1 hour, the reaction mixture was evaporated under reduced pressure to provide the required crude product (8.2 g) which, despite containing succinimide, may be used without further purification. If desired, purification may be effected by partitioning the crude product between dichloromethane and water, separating and drying (MgSO4) the organic phase and evaporating it under reduced pressure, then triturating the resulting yellow solid with hexane to give the title compound as a white solid, m.p. 213 C. (decomp.).
	In acetonitrile;	Preparation 1 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole N-Iodosuccinimide (3.52 g) was added in portions, over 5 minutes, to a stirred solution of <strong>[120068-79-3]5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole</strong> (EP-A-0295117; 5.0 g) in acetonitrile (60 ml) at room temperature. After being stirred for 1 hour, the reaction mixture was evaporated under reduced pressure to provide the required crude product (8.2 g) which, despite containing succinimide, may be used without further purification. If desired, purification may be effected by partitioning the crude product between dichloromethane and water, separating and drying (MgSO4) the organic phase and evaporating it under reduced pressure, then triturating the resulting yellow solid with hexane to give the title compound as a white solid, m.p. 213 C. (decomp.).

Reference： [1]Patent: US6019986,2000,A
[2]Patent: US6075043,2000,A

10
[ 516-12-1 ]
1-(triisopropylsilyl)-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]
3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In tetrahydrofuran;	N-Iodosuccinimide (653 mg, 2.9 mmol) was added to a stirred solution of 2-methoxycarbonyl-1-triisopropylsilylpyrrole (815 g, 2.9 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred at room temperature for two days. The solvent was then removed in vacuo and the oily residue suspended in hexanes (50 mL) with vigorous stirring. The insoluble solid was removed by filtration and the filtrate concentrated in vacuo. Purification of the residue by column chromatography using hexanes gave 3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole (1.044 g, 88percent) as a white crystalline solid, mp 81-83° C.: 1 H NMR (CDCl3) delta 7.18 (d, 1H, J=1 5 Hz), 7.09 (d, 1H, J=1.5 Hz), 379 (s, 3H), 1.74 (sept, 3H, J=7.6 Hz), 1.11 (d, 18H, J=7.6 Hz). Anal. Calcd for C15 H26 INO2 Si: C, 44.23; H, 6.43; N, 3.44. Found: C, 44.00; H, 6.53; N, 3.43.

Reference： [1]Patent: US6066639,2000,A

11
[ 516-12-1 ]
phenyl BODIPY [ No CAS ]
[ 1083009-44-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	In dichloromethane; at 25℃; for 0.5h;	General procedure: <strong>[516-12-1]NIS</strong> (4 eq.) was added to a solution of correspondent BODIPY (C andE) (1 eq.) in CH2Cl2. The mixture was stirred 25 min at room temperaturebased on the TLC analysis. The residue obtained after the removalof the solvent by rotary evaporation was extracted with EtOAcand washed with saturated solution of2Sa2qOu3e(o3u×s 2N0aml),and water (3×30 ml), then dried over anhydrous Na2SO4 and evaporatedin vacuo. The crude material obtained was further purifiedthrough column chromatography on silica gel using hexane/CH2Cl2(1:1) as the eluent to obtain the derivatives 3a and 3c.2.3.1.1. 3a). Yield 93%, 182 mg. 1H NMR (400 MHz, CHCl3-d) 4/ppm=7.54-7.50 (m, 3H), 7.26-7.23 (m, 2H), 2.65 (s, 6H), 1.38 (s,6H). 13C NMR (100 MHz, CHCl3-d) 4/ppm=156.9, 145.5, 141.5,134.9, 131.4, 129.7, 129.6, 127.9, 85.8, 17.1, 16.2. MS (EI): m/zcalcd for [C19H17BF2I2N2]+: 575.97; found: 576.10. Anal. Calcd forC19H17BF2I2N2: C, 39.62; H, 2.98; N, 4.86%. Found: C, 39.58; H, 2.96;N, 4.81%.

Reference： [1]Dyes and Pigments,2019,vol. 171
[2]Chemical Communications,2008,p. 4777 - 4779
[3]Organic and Biomolecular Chemistry,2011,vol. 9,p. 8141 - 8146
[4]ChemPlusChem,2018,vol. 83,p. 339 - 347
[5]New Journal of Chemistry,2019,vol. 43,p. 16829 - 16834

12
[ 516-12-1 ]
[ 3680-69-1 ]
[ 123148-78-7 ]

Yield	Reaction Conditions	Operation in experiment
86.9%	In N,N-dimethyl-formamide; at 20℃;	Step 1:4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and <strong>[516-12-1]N-iodosuccinimide</strong> (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 lambdamax: 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

13
[ 516-12-1 ]
[ 16740-98-0 ]
[ 1316849-01-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	In acetonitrile; at 20℃; for 12h;Inert atmosphere; Darkness;	Compound 13 (4.56 g, 24.2 mmol) under argon cover in a brown glass flask was dissolved in anhydrous acetonitrile (100 mL), treated with <strong>[516-12-1]N-iodosuccinimide</strong> (10.6 g, 48 mmol) and stirred for 12 h at room temperature. The solvent was evaporated, the raw material dissolved in ethyl acetate, the solution washed with aqueous sodium sulfite solution, dried over sodium sulfate and purified on silica gel with toluene/ethyl acetate 3:1 to give 3 as a colorless syrup. Yield 8.9 g (89percent); inlMMLBox 52 (c 1.34, CHCl3).1H NMR (400 MHz,CDCl3): delta = 2.64 (s, 4H, imide), 3.37, 3.40, 3.47 (each s, each 3H, OCH3), 3.36 (dd, 1H, J2,3 = 3.0, J3,4 = 2.5 Hz, H-3), 3.58 and 3.73 (each dd, each 1H, J5,6 = 10.0, J5,6' = 6.0, J6,6' = 12.0 Hz, H-6, H-6'), 3.67 (dd, 1H, J3,4 = 2.5, J4,5 = 2.0 Hz, H-4), 4.33 (ddd, 1H, J4,5 = 2.0, J5,6 = 10.0, J5,6' = 6.0 Hz, H-5), 5.22 (d, 1H, J1,2 = 11.5 Hz, H-1).13C NMR (100 MHz, CDCl3): delta = 27.55 (2C, CH2, imide), 28.19 (C-2), 55.51, 55.79, 56.45 (3C, OCH3), 61.41 (CH2, C-6), 67.56, 73.81, 74.94 (C-3, C-4, C-5), 79.99 (C-1), 177.36 (2C, q, imide CO).Anal. Calcd for C13H20 INO6 (413.2): C, 37.79; H, 4.88; N, 3.39. Found: C, 37.65; H, 4.81; N, 3.28.

Reference： [1]Carbohydrate Research,2011,vol. 346,p. 1546 - 1550

14
[ 516-12-1 ]
ethyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside [ No CAS ]
[ 1320337-28-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	In dichloromethane; at 0℃; for 0.416667h;Molecular sieve;	N-Iodosuccinamide (1.2 mmol) and molecular sieves 4 A were added to a stirred solution of 1 (1 mmol) in CH2Cl2, stirred for 25 min at 0 °C, diluted with CH2Cl2, washed with aq Na2S2O3 (5percent) solution, brine, concentrated in vacuo and purified by column chromatography (SiO2).Yield: 84percent. Rf = 0.5 (35percent EtOAc/pet. ether). 1H NMR (CDCl3, 400 MHz) delta 6.11 (d, J = 10.2 Hz, 1H), 5.78 (d, J = 10.2 Hz, 1H), 5.73 (m, 1H), 5.46 (s, 1H) 4.33 (m, 1H), 4.25-4.15 (m, 2H), 2.15 (s, 3H), 2.08 (s, 3H), 2.77-2.73 (band, 4H); 13C NMR (CDCl3, 100 MHz) delta 176.9, 175.4, 170.2, 129.3, 128.8, 126.7, 125.9, 89.8, 74.7, 70.8, 62.5, 29.5, 28.0, 20.9, 20.8. HR-MS: m/z calcd for C14H17O7N 334.0903 [M+Na]+. Found: 334.0911.

Reference： [1]Carbohydrate Research,2011,vol. 346,p. 1569 - 1575

15
[ 516-12-1 ]
phenyl BODIPY [ No CAS ]
[ 1296869-56-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	In dichloromethane;	N-Iodosuccinimide (<strong>[516-12-1]NIS</strong>) (300 mg, 1.33 mmol) was dissolved in 30 mL anhydrous CH2Cl2, then the solution was added dropwise into the solution of compound 1 (429.0 mg, 1.33 mmol) in CH2Cl2. After the reaction was completed, water (50 mL) was added, then the organic layer was extracted by CH2Cl2, the organic phase was evaporated to dry under vacuum. The crude material was purified by silica gel column chromatography (eluent: CH2Cl2/petroleum = 1/2). A red solid was collected after purification. (419.0 mg, yield: 70percent). 1H NMR (300 MHz, CDCl3): delta 7.49 - 7.51 (m, 3H), 7.25 - 7.27 (m, 2H, overlapped with CDCl3), 6.04 (s, 1H), 2.64 (s, 3H), 2.57 (s, 3H), 1.38 (s, 6H).

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 8141 - 8146
[2]Chemistry - A European Journal,2013,vol. 19,p. 17472 - 17482
[3]Chinese Chemical Letters,2017,vol. 28,p. 875 - 880
[4]Dalton Transactions,2013,vol. 42,p. 14374 - 14379
[5]Australian Journal of Chemistry,2020
[6]Dalton Transactions,2015,vol. 44,p. 4032 - 4045
[7]Chemistry - A European Journal,2015,vol. 21,p. 13201 - 13205

16
[ 516-12-1 ]
[ 4532-25-6 ]
[ 908267-60-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2793 - 2800

17
[ 516-12-1 ]
(S)-3-(imidazo[1,2-b]pyridazin-6-ylaminomethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]
(S)-2-[(3-iodo-imidazo[1,2-b]pyridazin-6-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.6 g	With sodium metabisulfite; In water; N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	<strong>[516-12-1]N-iodosuccinimide</strong> [516-12-1] (1.1 g, 4. 7 mmol) was added to an ambient temperaturesolution of (S)-3-(imidazo[1,2-b]pyridazin-6-ylaminomethyl)-pyrrolidine-1-carboxylic acid tert-butylester (1.4 g, 4.3 mmol) in DMF (43 ml) and allowed to stir under N2 blanket overnight then poured30 into a stirred aqueous solution of 5percent (wjv) sodium meta bisulfite precipitate product and the twophase mixture extracted with ethyl acetate. The extract was dried (CaS04), evaporated, andrecrystallized from chilled ethyl acetate to yield 0.6 g of (S)-2-[(3-iodo-imidazo[1,2-b]pyridazin-6-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a white powder, mp. 138-139°C. 1HNMR (400 MHz, DMSO-d6) 8 ppm 1.37 (br. s., 8 H) 1.79 (dd, J=9.98, 5.18 Hz, 1 H) 1.84-1.92 (m, 2H) 1.97 (br. s., 1 H) 3.23- 3.40 (m, 4 H) 3.42 - 3.53 (m, 1 H) 4.01 (br. s., 1 H) 6.69 (d, J=9.60 Hz, 1H) 7.09 (t, J=5.94 Hz, 1 H) 7.47 (s, 1 H) 7.64 (d, J=9.60 Hz, 1 H). 13C NMR (100 MHz, DMSO-d6) 8ppm 22.35, 23.20, 28.11, 28.54, 43.21, 45.99, 46.35, 56.25, 70.08, 78.32, 112.67, 125.09,136.22, 137.90, 154.42.

Reference： [1]Patent: WO2013/134219,2013,A1 .Location in patent: Page/Page column 107; 108

18
[ 637-69-4 ]
[ 516-12-1 ]
[ 1528729-29-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	at 45℃; for 2h;Molecular sieve; Inert atmosphere;	General procedure: The olefin (1.86 mmol) was mixed in freshly distilledpropionitrile (4.0 mL) and kept under an inert N2 atmosphere. 4 A molecularsieves (0.01 g) were added to maintain anhydrous conditions. The amide(5.58 mmol) was added to the flask and the reaction mixture was heated to45 C until it became homogenous. This was followed by the addition of Niodosuccinimide(3.72 mmol) and the flask subsequently covered withaluminum foil. The reaction mixture was stirred at 45 C for 2 h andmonitored using TLC until complete disappearance of the starting materialwas detected. The reaction was quenched with deionized water and the crudemixture diluted in DCM (50 mL). The mixture was washed with a saturatedsolution of Na2S2O3 (100 mL) and deionized water (3 100 mL). The organiclayer was dried with MgSO4 and the solvent removed in vacuo.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 448 - 452

19
[ 516-12-1 ]
[ 942588-55-8 ]
[ 1548823-41-1 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 972 - 975

20
[ 516-12-1 ]
[ 1073711-40-6 ]
[ 1548823-54-6 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 972 - 975

21
[ 516-12-1 ]
[ 2380-63-4 ]
[ 151266-23-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	In N,N-dimethyl-formamide; at 80℃; for 12h;	Pyrazolo [3,4-d] pyrimidin-4-amine (15.0 g, 111.1 mmol) was dissolved in DMF (150 mL) <strong>[516-12-1]N-iodosuccinimide</strong> (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).
	In N,N-dimethyl-formamide; at 80℃;	To 1L to reaction bottle 40.54g (0.3mol) intermediate 1, DMF360mL, at the same time adding N-iodo succinimide 101.24g (0.45mol), system temperature to 80 °C reaction 22-24h, TLC central control, raw material the reaction is complete. Added to system 360 ml water quenching reaction, in this system a large number of brown solid precipitated. Filtering, to obtain ponders the cake 64.37g crude brown solid, yield: 82.2percent, HPLC: 95.9percent.

Reference： [1]Patent: CN105399756,2016,A .Location in patent: Paragraph 0155; 0165-0166
[2]Patent: CN105859728,2016,A .Location in patent: Paragraph 0073; 0074

22
[ 516-12-1 ]
[ 60290-21-3 ]
4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In N,N-dimethyl-formamide; at 0 - 20℃; for 18h;	Step 1. Synthesis of 4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine (C6) N-Iodosuccinimide (1.3 g, 5.8 mmol) was added to a 0 C. solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> (0.60 g, 3.9 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at room temperature for 18 hours, whereupon it was concentrated in vacuo. Purification via silica gel chromatography (0% to 50% ethyl acetate in petroleum ether) afforded the product as a yellow solid. Yield: 900 mg, 3.2 mmol, 82%. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=5.5 Hz, 1H), 7.42 (d, J=2.5 Hz, 1H), 7.34 (d, J=5.8 Hz, 1H).

Reference： [1]Patent: US2014/128374,2014,A1 .Location in patent: Paragraph 0330; 0331

23
[ 516-12-1 ]
[ 540-38-5 ]
(4aR,7R,8S,8aR)-7-(benzyloxy)-8-fluoro-6-(4-iodophenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With trifluorormethanesulfonic acid; In dichloromethane; ethyl acetate;	Step I: (4aR,7R,8S,8aR)-7-(benzyloxy)-8-fluoro-6-(4-iodophenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine To a cold (-40° C.) solution of INTERMEDIATE M2 (140 mg, 0.3094 mmol) and 4-iodophenol (109 mg, 0.495 mmol) in CH2Cl2 (4.5 mL) is added 1-iodopyrrolidine-2,5-dione (111 mg, 0.495 mmol) and trifluoromethanesulfonic acid (4 muL, 0.0460 mmol). The reaction mixture is stirred 1 h at -40° C. and 16 h at RT. The resulting mixture is partitioned between saturated NaHCO3 (4 ml) and CH2Cl2 (8 ml). The organic extract is dried (Na2SO4), filtered, evaporated to dryness and purified on Biotage? SNAP silica cartridge (10 g) using EtOAc (0percent to 20percent in 10 CV) in Hex as eluent to afford the titled compound (100 mg, 0.178 mmol, 57percent). LC-MS: m/z=563.39 (M+H)+.

Reference： [1]Patent: US2014/274930,2014,A1 .Location in patent: Page/Page column

24
[ 516-12-1 ]
[ 37900-81-5 ]
5-chloro-2-iodo-4-(trifluoromethyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic acid; at 20℃; for 48h;	A mixture of <strong>[37900-81-5]3-chloro-4-(trifluoromethyl)phenol</strong> (3.00 g, 15.3 mmol) and N-iodosuccinimide (95percent, 3.61 g, 15.2 mmol) in acetic acid (10 mL) was stirred for 5 minutes, whereupon sulfuric acid (18 M, 0.25 mL, 4.5 mmol) was added. After the reaction mixture had been stirred at room temperature for 2 days, it was partitioned between diethyl ether and water. The organic layer was washed with water and with 2 M aqueous sodium thiosulfate solution, then treated with activated carbon and dried over magnesium sulfate. The mixture was filtered through a pad of diatomaceous earth and silica gel, and the filtrate was concentrated in vacuo to afford an oil (4.9 g) containing product, acetic acid, and solvent. This material was taken into the following step without additional purification. GCMS m/z 322.0 [M+]. 1H NMR (400 MHz, CDCl3), product peaks only: delta 7.95 (s, 1H), 7.12 (s, 1H).

Reference： [1]Patent: US2016/222007,2016,A1 .Location in patent: Paragraph 0361; 0362

25
[ 61825-94-3 ]
[ 516-12-1 ]
trans-[Pt(trans-(1R, 2R)-1,2-cyclohexanediammine)(oxalate)(C₄H₄NO₂)l] [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 1706 - 1712

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[ CAS No. 516-12-1 ]

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

[ 516-12-1 ] Synthesis Path-Downstream 1~25

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