[ CAS No. 39028-27-8 ] {[proInfo.proName]}

Name: 39028-27-8|2,5-Dioxopyrrolidin-1-yl 2-iodoacetate|95%
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SKU: A553805
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Quality Control of [ 39028-27-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 39028-27-8 ]

SDS Specification

Alternatived Products of [ 39028-27-8 ]

Product Details of [ 39028-27-8 ]

CAS No. :	39028-27-8	MDL No. :	MFCD00058451
Formula :	C₆H₆INO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VRDGQQTWSGDXCU-UHFFFAOYSA-N
M.W :	283.02	Pubchem ID :	3299230
Synonyms :	SIA Crosslinker	Chemical Name :	2,5-Dioxopyrrolidin-1-yl 2-iodoacetate

Calculated chemistry of [ 39028-27-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.3
TPSA :	63.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	-0.09
Log Po/w (WLOGP) :	-0.35
Log Po/w (MLOGP) :	0.43
Log Po/w (SILICOS-IT) :	0.78
Consensus Log Po/w :	0.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.34
Solubility :	12.9 mg/ml ; 0.0457 mol/l
Class :	Very soluble
Log S (Ali) :	-0.8
Solubility :	45.4 mg/ml ; 0.16 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.14
Solubility :	20.3 mg/ml ; 0.0718 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.39

Safety of [ 39028-27-8 ]

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

Application In Synthesis of [ 39028-27-8 ]

* 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 [ 39028-27-8 ]
Downstream synthetic route of [ 39028-27-8 ]

[ 39028-27-8 ] Synthesis Path-Upstream 1~1

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

Yield	Reaction Conditions	Operation in experiment
30%	at 0 - 20℃; for 4 h;	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 β-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, 30percent yield). ¹H NMR (CDCl₃) δ ppm: 2.87 (2H, s), 3.96 (1H, s); 13C NMR (CDCl₃) δ ppm: −12.47 (1C, s) 25.85 (2C, s) 164.78 (1C, s) 168.78 (2C, s).

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 32, p. 7777 - 7791
[2] Patent: US2013/273581, 2013, A1, . Location in patent: Page/Page column 0092; 0111-0112; 0114
[3] Farmaco, 1992, vol. 47, # 11, p. 1367 - 1383

[ 39028-27-8 ] Synthesis Path-Downstream 1~85

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).

Reference： [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 ]

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

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

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

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

Reference： [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 ]

Reference： [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 ]

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

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

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

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