Dansyl chloride

Base Information

• Chemical Name: Dansyl chloride
• CAS No.: 605-65-2
• Deprecated CAS: 558479-38-2
• Molecular Formula: C12H12ClNO2S
• Molecular Weight: 269.752
• Hs Code.: 29214980
• European Community (EC) Number: 210-092-6
• NSC Number: 83616
• UNII: QMU9166TJ4
• DSSTox Substance ID: DTXSID2060543
• Nikkaji Number: J6.823C
• Wikipedia: Dansyl_chloride
• Wikidata: Q409512
• Metabolomics Workbench ID: 57962
• Mol file: 605-65-2.mol

Synonyms:5-(dimethylamino)naphthalene-1-sulfonylchloride;5-(N,N-dimethylamino)naphthalene-1-sulfonyl chloride;dansyl chloride;dansyl chloride, 3H-labeled;dansylchloride;DNS-Cl

Chemical Property of Dansyl chloride

Chemical Property:

• Appearance/Colour: yellow to orange-yellow crystalline powder
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Melting Point: 70-73 °C(lit.)
• Refractive Index: 1.636
• Boiling Point: 371.3 °C at 760 mmHg
• PKA: 2.38±0.40(Predicted)
• Flash Point: 178.4 °C
• PSA: 45.76000
• Density: 1.361 g/cm³
• LogP: 3.91410
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: acetone: 50 mg/mL
• Water Solubility.: Soluble in dimethyl fluoride, acetone, chloroform, pyridine, benzene and dioxane. Insoluble in water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 269.0277275
• Heavy Atom Count: 17
• Complexity: 363

Purity/Quality:

99.0% ^*data from raw suppliers

Dansyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-3

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthalenes
• Canonical SMILES: CN(C)C1=CC=CC2=C1C=CC=C2S(=O)(=O)Cl
• Uses: Dansyl chloride or 5-Dimethylaminonaphthalene-1-sulfonyl chloride (CAS 605-65-2) is a fluorogenic reagent used for protein, N-terminal amino acid and peptide detection by reverse phase high performance liquid chromatography (HPLC). It is also used to determine the degree of labeling in chymotrypsin and ovalbumin. It acts as a precursor for the synthesis of other derivatives like dansyl amide. Dansyl chloride is non-fluorescent until it reacts with amines. The resulting Dansyl amides have environmentally sensitive fluorescence quantum yields and emission maxima along with large Stokes shifts. This environment-sensitive fluorescence property has made Dansyl chloride an important tool for biophysical studies. Reagent for fluorescent labelling of amines, amino acids and proteins. A fluorogenic reagent for N-terminal derivatization of amino acids and peptides and detection by reverse phase HPLC. In fluorescent labelling, column chromatography, HPLC. Dansyl chloride is a fluorogenic reagent used for protein, N-terminal amino acid and peptide detection by reverse phase high performance liquid chromatography (HPLC). It is also used to determine the degree of labeling in chymotrypsin and ovalbumin. It acts as a precursor for the synthesis of other derivatives like dansyl amide.

Technology Process of Dansyl chloride

There total 4 articles about Dansyl chloride 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: 80.0%

dansyl acid (4272-77-9) → 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2)

Guidance literature:

With phosphorus pentachloride; for 2h;

Reference yield: 73.0%

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

Guidance literature:

Reference yield:

1-aminonaphthalene-5-sulfonic acid (84-89-9) → 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaHCO₃ / H₂O / 0.5 h / 80 °C

2: 75 percent / PCl₃ / 2 h / 60 °C

With sodium hydrogencarbonate; phosphorus trichloride; In water;

DOI:10.1002/hlca.19940770123

upstream raw materials:

dansyl acid

1-aminonaphthalene-5-sulfonic acid

trimethylphosphane

Downstream raw materials:

dansylamide

(S)-3-hydroxy-2-phenyl-propionic acid 9-(5-dimethylamino-naphthalene-1-sulfonyl)-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.0^2,4]non-7t-yl ester

(S)-3-acetoxy-2-phenyl-propionic acid 9-(5-dimethylamino-naphthalene-1-sulfonyl)-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.0^2,4]non-7t-yl ester

BMS-182874

Refernces

• 1、 -. "Preparation method of 6-deuterated dansyl chloride". Paragraph 0076-0077; 0079. . Retrieved 2020/12/14.
• 2、 Kim, Joong-Gon,Jang, Doo Ok. "A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4". experimental part. p. 3049 - 3052. Retrieved 2011/02/25.