146998-31-4

Basic information

• Product Name: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER
• Synonyms: DABCYL ACID, SE;DABCYL, SE;DABCYL SUCCINIMIDE ESTER;DABCYL-N-SUCCINIMIDYL ESTER;DABCYL-OSU;DABCYL-NHS;DABCYL N-HYDROXYSUCCINIMIDE ESTER;4-(DIMETHYLAMINO)AZOBENZENE-4'-CARBOXYLIC ACID N-SUCCINIMIDYL ESTER
• CAS NO: 146998-31-4
• Molecular Formula: C₁₉H₁₈N₄O₄
• Molecular Weight: 366.37
• Product Categories: Fluorescent Dyes
• Mol File: 146998-31-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 242 °C(dec.)
• Boiling Point: 550.702 °C at 760 mmHg
• Flash Point: 286.855 °C
• Appearance: white crystal powder
• Density: 1.306 g/cm³
• Vapor Pressure: 3.56E-12mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO.
• PKA: 3.28±0.10(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER(146998-31-4)
• EPA Substance Registry System: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER(146998-31-4)

Safety Data

• Safety Statements: 24/25
• RIDADR: 3234
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 146998-31-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 146998-31-4 differently. You can refer to the following data:
1. Non-Fluorescent probe for labeling proteins or peptides
2. 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.

InChI:InChI=1/C19H18N4O4/c1-22(2)16-9-7-15(8-10-16)21-20-14-5-3-13(4-6-14)19(26)27-23-17(24)11-12-18(23)25/h3-10H,11-12H2,1-2H3/b21-20+

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 201858-51-7 p-methyl red 

Downstream Products

• 1316832-39-9 (E)-allyl 9-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanamido)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oate 
• 1316833-14-3 tert-butyl (4S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(1-(4-((E)-(4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10,13-tetraoxo-8,14-dioxa-2,6,11-triazaheptadec-16-en-9-yl)phenyl)amino)-5-oxopentanoate 
• 1316832-42-4 (E)-9-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanamido)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oic acid 
• 1337555-71-1 9-(4((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-tert-butoxy-4-oxobutanamido)phenyl)-1-(4-((E)-(4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oic acid 
• 1316832-71-9 (E)-allyl 9-(4-(bis(2-nitrobenzyloxy)phosphoryloxy)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oate 
• 1316832-74-2 (E)-9-(4-(bis(2-nitrobenzyloxy)phosphoryloxy)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oic acid 
• 909729-58-4 C₁₇H₂₁N₅O 
• 146998-27-8 N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine 

Relevant articles and documents

Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics

The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans-cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO-linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.

TUNABLE FLUORESCENCE USING CLEAVABLE LINKERS

The invention relates to cleavable chemistry in general, and in particular, to tunable fluoresence using cleavable linkers present in fluorochrome-quencher conjugates.

Synthesis of dye-labeled lysine derivatives

The N(ε)-dabcyl-N(α)-(9-fluorenylmethoxy)-carbonyllysine was prepared by reaction of lysine-Cu2+ complex with the N-hydroxysuccinimide (HOSu) activated ester of [4-(4'-dimethylamino)phenylazo]benzoic acid (dabcyl acid) followed by treatment with EDTA and acylation with Fmoc-OSu, and the N(α)tert-butyloxycarbonyl-N(ε)-dabcyllysine was prepared by reaction of N(α)-tertbutyloxycarbonyllysine with dabcyl-OSu.