56512-49-3

Basic information

• Product Name: DABSYL CHLORIDE
• Synonyms: 4-((4-(dimethylamino)phenyl)azo)-benzenesulfonylchlorid;4-[[4-(dimethylamino)phenyl]azo]-benzenesulfonylchlorid;4-n,n-dimethylaminoazobenzene-4’-sulfonylchloride;p-((p-(dimethylamino)phenyl)azo)-benzenesulfonylchlorid;4-DIMETHYLAMINOAZOBENZENE-4'-SULPHONYL CHLORIDE;4-DIMETHYLAMINOAZOBENZENE-4-SULPHONYL CHLORIDE;4-DIMETHYLAMINOAZOBENZENE-4'-SULFONYL CHLORIDE;4-DIMETHYLAMINOAZOBENZENE-4-SULFONYL-CHLORIDE
• CAS NO: 56512-49-3
• Molecular Formula: C₁₄H₁₄ClN₃O₂S
• Molecular Weight: 323.8
• EINECS: 260-235-1
• Product Categories: marker
• Mol File: 56512-49-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 185 °C (dec.)(lit.)
• Boiling Point: 483.6 °C at 760 mmHg
• Flash Point: 246.3 °C
• Appearance: Red crystalline powder
• Density: 1.29 g/cm³
• Storage Temp.: −20°C
• Solubility: DMF: soluble
• PKA: 3.27±0.10(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 3064095
• CAS DataBase Reference: DABSYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DABSYL CHLORIDE(56512-49-3)
• EPA Substance Registry System: DABSYL CHLORIDE(56512-49-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: DB8927800
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 56512-49-3(Hazardous Substances Data)

Usage

Chemical Properties

Dark red crystalline

Uses

For the qualitative and quantitative identification of amino acids and for the determination of N-terminal amino acids. Used in the determination of primary and secondary amines by HPLC.

General Description

Amino groups are common to many biological compounds and many amines used in pharmaceuticals. Most of these compounds show weak absorption in direct HPLC analysis with UV-VIS detection. However, strongly absorbing derivatives of amines can be easily detected by HPLC with high sensitivity even when present at low concentrations. Primary and secondary amino groups are usually derivatized as aromatic derivatives by nucleophilic substitution reactions using reagents such as arylsulfonyl chlorides.4-(Dimethylamino)azobenzene-4′-sulfonyl chloride, a well-known UV-labeling agent, is generally used for the derivatization of N-terminal amino acids, imidazole derivatives, polyamines, etc. prior to their chromatographic determination due to the former′s capacity to covalently bind to the substrates. Its derivatives typically absorb UV radiation between the range of 436-460 nm. This method of derivatization is regarded as superior compared to other methods owing to the simplicity of the procedure, high stability and reproducibility, best resolution of the analytes, etc.

Upstream product

• 502-02-3 methyl orange 
• 547-58-0 methyl orange 

Downstream Products

• 515-59-3 sulfamethylthiazole 
• 72720-22-0 Dimethyl-{4-[4-(piperidine-1-sulfonyl)-phenylazo]-phenyl}-amine 
• 72720-21-9 N,N-dimethyl-4-[2-[4-(1-piperazinylsulfonyl) phenyl]diazenyl]benzenamine 
• 72720-17-3 4-(4-Dimethylamino-phenylazo)-N-propyl-benzenesulfonamide 
• 146303-63-1 4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 3,4-dimethyl-phenyl ester 
• 146303-72-2 4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 2,4-dinitro-phenyl ester 
• 146303-69-7 4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid pentachlorophenyl ester 
• 146303-61-9 4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid p-tolyl ester 
• 72720-25-3 {[4-(4-Dimethylamino-phenylazo)-benzenesulfonyl]-methyl-amino}-acetic acid 
• 146303-67-5 4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 2,4-dibromo-phenyl ester 
• 146303-64-2 4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 2-chloro-phenyl ester 
• 146303-78-8 1,6-dihydroxynaphthalene didabsylate 
• 146303-79-9 1,8-dihydroxynaphthalene didabsylate 
• 146303-77-7 methyl 2,4-dihydroxybenzoate didabsylate ester acid 

Relevant articles and documents

A highly selective “Turn On” fluorescent probe based on FRET mechanism for hydrogen sulfide detection in living cells

A novel class of fluorescent “turn on” probe based on the fluorescence resonance energy transfer (FRET) approach was designed, and successfully synthesized for the detection of hydrogen sulfide (H2S) both in vitro and in vivo. This new H2S responsive fluorescent probe was developed based on the basis of the dabsyl and fluorescein FRET system. In the presence of H2S, a fluorescence enhancement was markedly observed mainly due to the inhibition of the FRET process. This probe could quantitatively measure the level of H2S with the detection limit of 0.02 μM. Cell imaging results demonstrated the potential applicability of a dabsylfluorescein probe for H2S detection in living cells.

PRODUCTION, PROPERTIES, AND MASS-SPECTROMETRIC INVESTIGATION OF THE DABSYLATES OF PHENOLS

The reaction of monohydric and dihydric phenols and phloroglucinol with 4'-(dimethylamino)azobenzene-4-sulfonyl chloride (dabsyl chloride) leads to the respective mono-, di-, and triabsylates of the phenols.Their structures were confirmed by IR, PMR, and mass spectrometry.A scheme is proposed for the dissociation of the phenol dabsylates under electron impact.The transformation of the phenols into the derivatives by reaction with dabsyl chloride is recommended for highly sensitive and selective determination of the individual phenols by high-performance liquid chromat ography with spectrophotometric detection and for spectrophotometric determination of total phenol content.