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Dansyl chloride, also known as 5-Dimethylaminonaphthalene-1-sulfonyl chloride (CAS 605-65-2), is a fluorogenic reagent that is widely used in the field of biochemistry and biophysical studies. It is non-fluorescent until it reacts with amines, forming Dansyl amides which exhibit environmentally sensitive fluorescence quantum yields, emission maxima, and large Stokes shifts. This unique property has made Dansyl chloride an important tool for various applications in research and analysis.

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  • 605-65-2 Structure
  • Basic information

    1. Product Name: Dansyl chloride
    2. Synonyms: 1-(dimethylamino)-5-naphthalenesulfonylchloride;1-chlorosulfonyl-5-dimethylaminonaphthalene;5-(dimethylamino)-1-naphthalenesulfonylchlorid;5-dimethylaminonaphthyl-5-sulfonylchloride;dansyl;dimethylaminonaphthalenesulfonylchloride;1-DIMETHYLAMINONOPHTHALENE-5-SULPHONYL CHLORIDE;1-DIMETHYLAMINO-NAPHTHALENE-5-SULFONYL CHLORIDE
    3. CAS NO:605-65-2
    4. Molecular Formula: C12H12ClNO2S
    5. Molecular Weight: 269.75
    6. EINECS: 210-092-6
    7. Product Categories: Amino Group Labeling Reagents for Fluorescence HPLC;Analytical Chemistry;Fluorescence Detection (HPLC Labeling Reagents);HPLC Labeling Reagents;Hydroxyl Group Labeling Reagents for Fluorescence HPLC;Amines;Aromatics;Fluorescent Labels & Indicators;Sulfur & Selenium Compounds;marker
    8. Mol File: 605-65-2.mol
  • Chemical Properties

    1. Melting Point: 72-74 °C(lit.)
    2. Boiling Point: 371.3 °C at 760 mmHg
    3. Flash Point: 178.4 °C
    4. Appearance: yellow to orange/powder and chunks
    5. Density: 1.1702 (rough estimate)
    6. Vapor Pressure: 1.04E-05mmHg at 25°C
    7. Refractive Index: 1.5630 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: acetone: 50 mg/mL
    10. PKA: 2.38±0.40(Predicted)
    11. Water Solubility: Soluble in dimethyl fluoride, acetone, chloroform, pyridine, benzene and dioxane. Insoluble in water.
    12. Sensitive: Moisture Sensitive
    13. Merck: 14,2814
    14. BRN: 2217205
    15. CAS DataBase Reference: Dansyl chloride(CAS DataBase Reference)
    16. NIST Chemistry Reference: Dansyl chloride(605-65-2)
    17. EPA Substance Registry System: Dansyl chloride(605-65-2)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34
    3. Safety Statements: 26-36/37/39-45-3
    4. RIDADR: UN 3261 8/PG 2
    5. WGK Germany: 3
    6. RTECS: QK3688000
    7. F: 10-21
    8. TSCA: Yes
    9. HazardClass: 8
    10. PackingGroup: III
    11. Hazardous Substances Data: 605-65-2(Hazardous Substances Data)

605-65-2 Usage

Uses

Used in Biochemistry and Biomedical Research:
Dansyl chloride is used as a reagent for fluorescent labeling of amines, amino acids, and proteins. This application is particularly useful for the detection and analysis of these biomolecules in various research and diagnostic settings.
Used in Chromatography:
Dansyl chloride is employed as a fluorogenic reagent for N-terminal derivatization of amino acids and peptides, which is essential for their detection by reverse phase high performance liquid chromatography (HPLC). This technique is widely used in the separation, identification, and quantification of these molecules.
Used in Column Chromatography and HPLC:
Dansyl chloride is utilized in column chromatography and HPLC for the fluorescent labeling of proteins, N-terminal amino acids, and peptides. This allows for the efficient separation and detection of these biomolecules, which is crucial for various analytical and preparative purposes.
Used in Synthesis of Derivatives:
Dansyl chloride acts as a precursor for the synthesis of other derivatives, such as dansyl amide. These derivatives can be used in various applications, including the development of new fluorescent probes and labels for biological research.

Biochem/physiol Actions

Dansyl chloride is a sulfonyl chloride compound. It is used to end tag amino groups of peptides and proteins. Dansyl chloride is used for derivatization of free amino acids and amines in neural samples and biological fluids. It is used to study fluorescent conjugates of albumin, protein conformational changes studies and active site characterization.

Safety Profile

Poison by intravenous route, When heated to decomposition it emits very toxic fumes of Cland NOx

Check Digit Verification of cas no

The CAS Registry Mumber 605-65-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 605-65:
(5*6)+(4*0)+(3*5)+(2*6)+(1*5)=62
62 % 10 = 2
So 605-65-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H12ClNO2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3

605-65-2 Well-known Company Product Price

  • Brand
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  • CAS number
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  • Alfa Aesar

  • (A13828)  Dansyl chloride, 97+%   

  • 605-65-2

  • 1g

  • 296.0CNY

  • Detail
  • Alfa Aesar

  • (A13828)  Dansyl chloride, 97+%   

  • 605-65-2

  • 5g

  • 1039.0CNY

  • Detail
  • Alfa Aesar

  • (A13828)  Dansyl chloride, 97+%   

  • 605-65-2

  • 25g

  • 4304.0CNY

  • Detail
  • Sigma

  • (39220)  Dansyl chloride  BioReagent, suitable for fluorescence, ≥99.0% (HPLC)

  • 605-65-2

  • 39220-1G-F

  • 869.31CNY

  • Detail
  • Sigma

  • (39220)  Dansyl chloride  BioReagent, suitable for fluorescence, ≥99.0% (HPLC)

  • 605-65-2

  • 39220-5G-F

  • 4,856.67CNY

  • Detail
  • Sigma

  • (39220)  Dansyl chloride  BioReagent, suitable for fluorescence, ≥99.0% (HPLC)

  • 605-65-2

  • 39220-50G-F

  • 16,976.70CNY

  • Detail
  • Sigma-Aldrich

  • (03641)  Dansyl chloride  for HPLC derivatization, ≥99.0% (HPLC)

  • 605-65-2

  • 03641-100MG

  • 236.34CNY

  • Detail
  • Sigma-Aldrich

  • (03641)  Dansyl chloride  for HPLC derivatization, ≥99.0% (HPLC)

  • 605-65-2

  • 03641-10X100MG

  • 2,132.91CNY

  • Detail

605-65-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name dansyl chloride

1.2 Other means of identification

Product number -
Other names Dansyl Chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:605-65-2 SDS

605-65-2Relevant articles and documents

Preparation method of 6-deuterated dansyl chloride

-

Paragraph 0076-0077; 0079, (2020/12/14)

The invention belongs to the technical field of isotope derivatization reagent preparation, and particularly relates to a preparation method of 6-deuterated dansyl chloride. According to the preparation method, 6-deuterated dansyl chloride can be prepared from reaction raw materials including 5-amino-1-naphthalene sulfonic acid, sodium hydride, deuterated methyl iodide, phosphorus oxychloride andphosphorus pentachloride. The preparation method has the advantages of easily available raw materials, low toxicity, few intermediate products and high yield.

Degradable conjugates from oxanorbornadiene reagents

Kislukhin, Alexander A.,Higginson, Cody J.,Hong, Vu P.,Finn

supporting information; experimental part, p. 6491 - 6497 (2012/05/07)

Oxanorbornadienedicarboxylate (OND) reagents were explored for purposes of binding and releasing drugs from serum albumins as representative macromolecular carriers. Being highly reactive Michael acceptors, ONDs form adducts with thiols and amines, which then undergo retro-Diels-Alder fragmentation. A study of more than 30 model adducts revealed a number of modifications that can be used to influence adduct stability. For the most reactive OND linkers, the labeling of the single available bovine serum albumin (BSA) cysteine residue was complete within minutes at a mid-micromolar concentration of reactants. While a selectivity of greater than 1000-fold for thiol over amine was observed with model amino acids, the labeling of protein amines with ONDs is fast enough to be practical, as demonstrated by the reaction with thiol-depleted BSA. The OND-amine adducts were found to be up to 15 times more stable than OND-thiol adducts, and to be sensitive to acid by virtue of a stereochemically dependent acceleration of cycloreversion. The release rate of fluorescent cargo from serum albumins was tuned by selecting the coupling partners: the available half-lives ranged from 40 min to 7 days at 37 °C. Such versatility of release profiles from protein carriers, controlled by the nature of the OND linkage, is a useful addition to the drug delivery toolbox.

A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4

Kim, Joong-Gon,Jang, Doo Ok

experimental part, p. 3049 - 3052 (2011/02/25)

Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement

Activatable probes and methods for in vivo gene detection

-

, (2008/06/13)

Probes for detecting a target polynucleotide are provided. One aspect provides a molecular beacon probe set wherein the donor molecular beacon comprises a quantum dot and an acceptor molecular beacon comprises at least one reporter. The probes optionally comprise a protein transduction domain, targeting signal, or a combination thereof. Methods for detecting target polynucleotides using the disclosed probes are also provided.

Dual resonance energy transfer nucleic acid probes

-

, (2008/06/13)

Dual nucleic acid probes with resonance energy transfer moieties are provided. In particular, fluorescent or luminescent resonance energy transfer moieties are provided on hairpin stem-loop molecular beacon probes that hybridize sufficiently near each other on a subject nucleic acid, e.g. mRNA, to generate an observable interaction. The invention also provides lanthanide chelate luminescent resonance energy transfer moieties on linear and stem-loop probes that hybridize sufficiently near each other on a subject nucleic acid to generate an observable interaction. The invention thereby provides detectable signals for rapid, specific and sensitive hybridization determination in vivo. The probes are used in methods of detection of nucleic acid target hybridization for the identification and quantification of tissue and cell-specific gene expression levels, including response to external stimuli, such as drug candidates, and genetic variations associated with disease, such as cancer.

Bispiperidines as antithrombotic agents

-

, (2008/06/13)

Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents

The 2-Dansylethoxycarbonyl (=2-{[5-dimethylamino)naphthalen-1-yl]sulfonyl}ethoxycarbonyl; Dnseoc) group for protection of the 5'-hydroxy function in oligodeoxyribonucleotide synthesis

Bergmann,Pfleiderer

, p. 203 - 215 (2007/10/02)

Use of the 2-dansylethoxycarbonyl (=2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl])ethoxycarbonyl; Dnseoc) group as an intermediate 5'-OH protecting group in oligodeoxyribonucleotide synthesis using the automated phosphoramidite approach is described in a model study to an alternative strategy in RNA synthesis.

ARYL-VINYLSULFONE--REAGENTIEN ZUM SCHUTZ UND NACHWEIS VON THIOLFUNKTIONEN

Horner, L.,Lindel, H.

, p. 1 - 8 (2007/10/02)

Aryl vinyl sulfones selectively react with thiol groups to acid-stable compounds which easily are cleaved by mild bases to thiol compounds.Ester and amide groups are not attacked under these conditions.Therefore, these compounds are good protecting groups or labels in peptide chemistry.The following aryl vinyl sulfones were investigated: phenyl vinyl sulfone 1, p-carbethoxyphenyl vinyl sulfone 15 and the fluorescent 5-dimethylaminonaphthyl 1-vinyl sulfone 5 and 5-methoxynaphthyl-1 vinyl sulfone 10.The last two compounds are very useful reagents for the quantitative determination of SH-groups in polypeptides such as enzymes.

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