(E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate

Base Information

• Chemical Name: (E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate
• CAS No.: 146998-31-4
• Molecular Formula: C19H18N4O4
• Molecular Weight: 366.376
• Hs Code.: 29280000
• DSSTox Substance ID: DTXSID20400841
• Nikkaji Number: J1.365.533B
• Wikidata: Q27123087
• Mol file: 146998-31-4.mol

Synonyms:146998-31-4;DABCYL acid, SE;4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester;(E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate;DABCYL SE;4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER;dabcyl SE dye;Dabcyl, SE;2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate;1155356-49-2;(2,5-dioxopyrrolidin-1-yl) 4-[[4-(dimethylamino)phenyl]diazenyl]benzoate;Dabcyl-Nhs;2,5-Pyrrolidinedione, 1-[[4-[[4-(dimethylamino)phenyl]azo]benzoyl]oxy]-;N-Succinimidyl 4-[4-(Dimethylamino)phenylazo]benzoate;4-((4-(Dimethylamino)phenyl)azo)benzoic acid N-succinimidyl ester;DABCYL acid,SE;DABCYL SE, solid;DABCYL-N-succinimidyl ester;DABCYL N-Succinimidyl Ester;SCHEMBL608694;LCZC1520;CHEBI:52005;DTXSID20400841;IBOVDNBDQHYNJI-UHFFFAOYSA-N;HY-D1046;MFCD00467415;AKOS015900999;AKOS028108813;DABCYL-SE;AM84427;AS-11378;PD158032;CS-0100488;FT-0733519;S0857;C93422;F12219;A897949;J-008299;J-513156;Q27123087;N-Hydroxysuccinimide 4-[4-(dimethylamino)phenylazo]benzoate;4-(4-dimethylaminophenyl)diazenylbenzoic acid succinimidyl ester;4-((4-(Dimethylamino)phenyl)azo)benzoicacid N-su ccinimidyl ester;4-([4-(Dimethylamino)phenyl]azo)benzoic acid succinimidyl ester;4-(Dimethylamino)azobenzene-4'-carboxylic acid N-succinimidyl ester;4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester?;(E)-2,5-Dioxopyrrolidin-1-yl4-((4-(dimethylamino)phenyl)diazenyl)benzoate;1-[(4-{[4-(dimethylamino)phenyl]diazenyl}benzoyl)oxy]pyrrolidine-2,5-dione;2,5-dioxopyrrolidin-1-yl (E)-4-((4-(dimethylamino)phenyl)diazenyl)benzoate;1-[(4-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoyl)oxy]pyrrolidine-2,5-dione;4-((4-(dimethylamino)phenyl)az0)benzoic acid, Succinimidyl ester (DABCYL-SE);4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester, >=98.0% (HPLC)

Chemical Property of (E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 3.56E-12mmHg at 25°C
• Melting Point: 242 °C(dec.)
• Refractive Index: 1.632
• Boiling Point: 550.702 °C at 760 mmHg
• PKA: 3.28±0.10(Predicted)
• Flash Point: 286.855 °C
• PSA: 91.64000
• Density: 1.306 g/cm³
• LogP: 3.32670
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in DMSO.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 366.13280507
• Heavy Atom Count: 27
• Complexity: 575

Purity/Quality:

98% ^*data from raw suppliers

4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)N=NC2=CC=C(C=C2)C(=O)ON3C(=O)CCC3=O
• Uses: Non-Fluorescent probe for labeling proteins or peptides 4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester is a useful reagent (similar to MANCYL-SE) for labeling proteins or peptides through their amino-groups by forming stable peptide bonds. The succinimidyl ester is reactive with terminal amines or lysines of peptides and other nucleophiles for fluorescent studies of proteins. Its fluorescent properties (has a characteristic broad and intense visible absorption but has no fluorescence) make it an ideal long wavelength quencher and it has been utilized as an acceptor chromophore in FRET studies. It is also used for N-terminal modification of peptides in automated synthesis.

Technology Process of (E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate

There total 2 articles about (E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + p-methyl red (201858-51-7) → 4-((4-(dimethylamino)phenyl)azo)benzoic acid succinimidyl ester (146998-31-4,1155356-49-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 62.7%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + sodium 4-((4-(dimethylamino)phenyl)diazenyl)benzoate → 4-((4-(dimethylamino)phenyl)azo)benzoic acid succinimidyl ester (146998-31-4,1155356-49-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ja200808y

Reference yield: 100.0%

azidonorvaline + 4-((4-(dimethylamino)phenyl)azo)benzoic acid succinimidyl ester (146998-31-4,1155356-49-2) → C20H23N7O3 (1561749-40-3)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/c3ob42267d

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

p-methyl red

Downstream raw materials:

N^α-dabcyllysine

6-tert-butoxycarbonylamino-hexanoic acid 2-(tert-butyl-dimethyl-silanyloxy)-3-{[2-(3-{2-[2-(2-{2-[4-(4-dimethylamino-phenylazo)-benzoylamino]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionylamino)-ethoxy]-hydroxy-phosphoryloxy}-propyl ester

C₆₆H₈₀N₇O₅⁽¹⁺⁾*I^(1-)

C₆₈H₈₄N₇O₃⁽¹⁺⁾*I^(1-)

Refernces

• 1、 -. "ENZYME DETECTION COMPOUND AND MANUFACTURING METHOD OF THE COMPOUND". Paragraph 0039. . Retrieved 2018/02/27.
• 2、 Hu, Mingyu,Li, Lin,Wu, Hao,Su, Ying,Yang, Peng-Yu,Uttamchandani, Mahesh,Xu, Qing-Hua,Yao, Shao Q.. "Multicolor, one- and two-photon imaging of enzymatic activities in live cells with fluorescently quenched activity-based probes (qABPs)". supporting information; experimental part. p. 12009 - 12020. Retrieved 2011/09/21.