33008-06-9

Basic information

• Product Name: DANSYL HYDRAZINE
• Synonyms: 5-(DIMETHYLAMINO)-1-NAPHTHALENESULFONIC HYDRAZIDE;1-DIMETHYLAMINOPHTHALENE-5-SULPHONYL HYDRAZINE;5-Dimethylaminonaphthalene-1-sulfonyl hydrazine (dansyl hydrazine);Dansylhydrazine~5-Dimethylamino-1-naphthalenesulphonyl hydrazide;5-dimethylaminonaphthalene-1-sulphonohydrazide;DANSYLHYDRAZINE CRYSTALLINE;DANSYLHYDRAZINE, FOR FLUORESCENCE;5-Dimethylamino-1-naphthalenesulfonylhydrazide
• CAS NO: 33008-06-9
• Molecular Formula: C₁₂H₁₅N₃O₂S
• Molecular Weight: 265.33
• EINECS: 251-337-7
• Product Categories: Analytical Chemistry;Carbonyl Group Labeling Reagents for Fluorescence HPLC;Fluorescence Detection (HPLC Labeling Reagents);HPLC Labeling Reagents;Derivatization agents;Sulfonyl Hydrazides;Biochemicals and Reagents;Building Blocks;Chemical Synthesis;Luminescent Compounds/Detection;Organic Building Blocks;Sulfur Compounds
• Mol File: 33008-06-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 126-130 °C(lit.)
• Boiling Point: 450.8°Cat760mmHg
• Flash Point: 226.4°C
• Appearance: /
• Density: 1.331g/cm³
• Vapor Pressure: 2.57E-08mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble
• PKA: 9.31±0.40(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 2868662
• CAS DataBase Reference: DANSYL HYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: DANSYL HYDRAZINE(33008-06-9)
• EPA Substance Registry System: DANSYL HYDRAZINE(33008-06-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 33008-06-9(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

Different sources of media describe the Uses of 33008-06-9 differently. You can refer to the following data:
1. Dansylhydrazine (DH) is widely used as a fluorometric reagent for carbonyl compounds. Dansylated carbonyl molecules can be separated and identified by analytical techniques.
2. Dansylhydrazine can exhibit fluorescence, which can be used for the following:monitoring air pollution by detection of the hydrazones formed by acid-catalyzed derivatization of the carbonyl compoundsdetection of the separated glycoproteins via sodium dodecyl sulfate polyacrylamide gel electrophoresis(SDS-PAGE)

General Description

Dansylhydrazine (DNSH) is a fluorescent reagent which is commonly utilized for derivatization of carbonyl compounds.

InChI:InChI=1/C12H15N3O2S/c1-15(2)11-7-3-6-10-9(11)5-4-8-12(10)18(16,17)14-13/h3-8,14H,13H2,1-2H3

Upstream product

• 605-65-2 5-(dimethylamino)naphth-1-ylsulfonyl chloride 

Downstream Products

• 153120-73-1 Boc-Leu-NHNHDns 
• 1192881-08-5 2-(5-(dimethylamino)naphthalen-1-ylsulfonyl)-N-phenylhydrazinecarbothioamide 
• 153120-77-5 Boc-Ala-Ala-Trp-Phe-Leu-NHNHDns 
• 153120-76-4 Boc-Ala-Trp-Phe-Leu-NHNHDns 

Relevant articles and documents

Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation

Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.

Ratiometric Signaling of Hypochlorite by the Oxidative Cleavage of Sulfonhydrazide-Based Rhodamine-Dansyl Dyad

(Figure Presented). A reaction-based probe 1 for hypochlorite signaling was designed by the conjugation of two fluorophores, rhodamine and dansyl moieties, by the reaction of rhodamine B base with dansylhydrazine. Probe 1 exhibited pronounced hypochlorite-selective chromogenic and fluorescent signaling behavior over other oxidants used in practical applications, such as hydrogen peroxide, peracetic acid, and ammonium persulfate, as well as commonly encountered metal ions and anions. Signaling was attributed to the hypochlorite-induced oxidative cleavage of the sulfonhydrazide linkage of the probe. In particular, favorable ratiometric fluorescence signaling was possible by utilizing the emissions of the two fluorophores. A detection limit of 1.13 × 10-6 M (0.058 ppm) was estimated for the determination of hypochlorite. A paper-based test strip was prepared and was used as a semiquantitative indicator for the presence of hypochlorite in aqueous solutions. The probe was also successfully applied for the determination of hypochlorite in practical tap water samples.

N-arylsulfonyl hydrazones as inhibitors of IMP-1 metallo-β-lactamase

Members of a family of N-arylsulfonyl hydrazones have been identified as novel inhibitors of IMP-1, a metallo-β-lactamase of increasing prevalence. Structure-activity relationship studies have indicated a requirement for bulky aromatic substituents on each side of the sulfonyl hydrazone backbone for these compounds to serve as efficient inhibitors of IMP-1. Molecular modeling has provided insight into the structural basis for the anti-metallo-β-lactamase activity exhibited by this class of compounds.