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Quality Control of N-Succinimidyl iodoacetate Purity: 95% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Details of N-Succinimidyl iodoacetate

CAS No. :	39028-27-8
Formula :	C₆H₆INO₄
M.W :	283.02
SMILES Code :	O=C(ON1C(CCC1=O)=O)CI
Synonyms :	SIA Crosslinker; Iodoacetic acid N-hydroxysuccinimide ester
MDL No. :	MFCD00058451
InChI Key :	VRDGQQTWSGDXCU-UHFFFAOYSA-N
Pubchem ID :	3299230

Safety of N-Succinimidyl iodoacetate

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of N-Succinimidyl iodoacetate

* 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 [ 39028-27-8 ]

[ 39028-27-8 ] Synthesis Path-Downstream 1~35

1
[ 6066-82-6 ]
[ 64-69-7 ]
[ 39028-27-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With diisopropyl-carbodiimide; In ethyl acetate; at 20℃; for 24h;Sealed tube;	A 100-mL flask sealed with a sleeve stopper was charged with N- hydroxysuccinimide (1.15 g, 10 mmol) and iodoacetic acid (1.86 g, 10 mmol). 50 mL of ethyl acetate was added and diisopropylcarbodiimide (1.55 mL, 10 mmol) was added dropwise.The reaction was left stirring at room temperature for 24 h. The mixture was then filtered, the precipitate was washed with a minimum amount of ethyl acetate and dried in vacuo. The solids were dissolved in -50 mL of boiling isopropanol and the solution was transferred into a beaker to initiate crystallization. The crystals were filtered, washed with isopropanol and dried in vacuo to give 1.72 g (60%) of pure product as white crystals. The compound is indefinitely stable at -20 C and should be stored at this temperature. 'H NMR (500 MHz, CDCb) d 4.02 (s, 2H), 2.95 - 2.85 (m, 4H).
30%	With dicyclohexyl-carbodiimide; at 0 - 20℃; for 4h;	On a solution of N-hydroxysuccinimide (12.6 mmol) and dicyclohexylcarbodiimide (20.3 mmol) at 0 C., corresponding acid (6 mmol) was added and allowed to react for 4 hours at room temperature. In the case of compound VIa, a solution of maleic anhydride (10 mmol) and beta-alanine was added in N,N-dimethylformamide, which has been previously made react for 1 hour. After 4 hours, mixture was evaporated at reduced pressure and the crude was dissolved in dichloromethane and washed with water. Organic extracts were dried with anhydrous magnesium sulfate, filtered and evaporated to dryness. Resulting residue was recrystallized to give desired compound. [0112] Using this methodology, and corresponding acid, the following compounds were prepared: Succinimidyl iodoacetate (VIb, 30% yield). 1H NMR (CDCl3) delta ppm: 2.87 (2H, s), 3.96 (1H, s); 13C NMR (CDCl3) delta ppm: -12.47 (1C, s) 25.85 (2C, s) 164.78 (1C, s) 168.78 (2C, s).

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 7777 - 7791.
[2]Patent: WO2019/168654,2019,A2 .Location in patent: Paragraph 00232; 00234.
[3]Patent: US2013/273581,2013,A1 .Location in patent: Page/Page column 0092; 0111-0112; 0114.
[4]Il Farmaco,1992,vol. 47,p. 1367 - 1383.

2
[ 39028-27-8 ]
[ 76387-70-7 ]
[ 129365-01-1 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2755 - 2759.

3
[ 39028-27-8 ]
[ 72198-35-7 ]
[ 74252-23-6 ]

References: [1]Liebigs Annalen der Chemie,1980,p. 416 - 424.

4
[ 39028-27-8 ]
[ 142182-02-3 ]
[ 142182-11-4 ]

References: [1]Il Farmaco,1991,vol. 46,p. 1497 - 1516.

5
[ 39028-27-8 ]
[ 79677-63-7 ]
1-(N-benzyloxycarbonyl-3-iodo-L-tyrosyl)-2-iodoacetylhydrazine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 297 - 311.

6
[ 39028-27-8 ]
[ 13724-90-8 ]
3-<(2''-iodoacetoamido)ethylthio>-rifamycin [ No CAS ]

References: [1]Il Farmaco,1992,vol. 47,p. 1367 - 1383.

7
[ 39028-27-8 ]
[ 87876-22-0 ]
[ 87876-25-3 ]

References: [1]Liebigs Annalen der Chemie,1983,vol. NO. 9,p. 1533 - 1540.

8
[ 39028-27-8 ]
[ 81035-22-5 ]
[ 81034-80-2 ]