Available from stock

Dansyl chloride

SKU: D0043

Category: Amino Acids, Peptides, Proteins

Synonyms: 5-(Dimethylamino)naphthalene-1-sulfonyl chloride , DNSC , DNS chloride , DNSCl , NSC 83616; 605-65-2
CAS-Number: C₁₂H₁₂ClNO₂S
Molecular Formula: 269.75
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: Yellow to orange powder
Identity: 1H-NMR

Properties

Solvents: DMF, acetone, chloroform, pyridine, benzene or dioxane, water (insoluble), DMSO solutions (unstable)
Melting Point: 72-74 °C (lit.)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H314
Precautionary statements: P280-P305 + P351 + P338-P310
GHS Symbol: GHS05
Signal word: Danger
RIDADR: UN3261 8
Transportation: Packing Group II

Description: Dansyl chloride is a fluorogenic probe that reacts with primary amino groups in both aliphatic and aromatic amines to produce stable blue- or blue-green-fluorescent sulfonamide adducts. It is used for protein sequencing and N-terminal amino acid and peptide analysis by reverse phase high performance liquid chromatography (HPLC). It can also be used to label hydroxyl and carboxylic acid functional groups. 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, in combination with their ability to accept energy (as in fluorescence resonance energy transfer) from the amino acid tryptophan, has made Dansyl chloride an important tool for biophysical studies. It is particularly useful for preparing fluorescent drug or ligand analogs that are expected to bind to hydrophobic sites in proteins or membranes or other biological receptors. Dansyl protein conjugates have fluorescence lifetimes of 10-20 nanoseconds. Spectral Date in DMF: Excitation/Emission ~333nm/515nm. Dansyl chloride is unstable in dimethyl sulfoxide, which should never be used to prepare solutions of the reagent. Dansyl chloride is one of the simplest sulfonamide derivatives, so it commonly serves as a starting reagent for the production of other derivatives.
Smiles: CN(C)C1=C(C=CC=C2S(=O)(Cl)=O)C2=CC=C1
InChi Key: XPDXVDYUQZHFPV-UHFFFAOYSA-N
References: (1) R.E. Boyle, J. Org. Chem. 31, 3880 (1966) , (2) R.F. Chen, Anal. Biochem. 25, 412 (1968) , (3) T. Kinoshita, et al., Chem. Pharm. Bull. 22, 2413 (1974) , (4) A.F. Sikorski & R.B. Daczynska, Biochim. Biophys. Acta 690, 302 (1982) , (5) R.F. Chen & C.H. Scott, Anal. Lett. 18, 393 (1985) , (6) J.M. Walker, Methods Mol. Biol. 32, 321 (1994) , (7) K.J. Hunter, Methods Mol. Biol. 79, 119 (1998) , (8) H. Yamada, et al., Biol. Pharm. Bull. 21, 778 (1998) , (9) T. Takeuchi, J. Chromatogr. Lib. 70, 229 (2005) , (10) T. Santa, Biomed. Chromatogr. 25, 1 (2011)

Dansyl chloride is a fluorogenic probe that reacts with primary amino groups in both aliphatic and aromatic amines to produce stable blue- or blue-green-fluorescent sulfonamide adducts. It is used for protein sequencing and N-terminal amino acid and peptide analysis by reverse phase high performance liquid chromatography (HPLC). It can also be used to label hydroxyl and carboxylic acid functional groups. 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, in combination with their ability to accept energy (as in fluorescence resonance energy transfer) from the amino acid tryptophan, has made Dansyl chloride an important tool for biophysical studies. It is particularly useful for preparing fluorescent drug or ligand analogs that are expected to bind to hydrophobic sites in proteins or membranes or other biological receptors. Dansyl protein conjugates have fluorescence lifetimes of 10-20 nanoseconds. Spectral Date in DMF: Excitation/Emission ~333nm/515nm. Dansyl chloride is unstable in dimethyl sulfoxide, which should never be used to prepare solutions of the reagent. Dansyl chloride is one of the simplest sulfonamide derivatives, so it commonly serves as a starting reagent for the production of other derivatives.

SKU: D0043 Category: Amino Acids, Peptides, Proteins

Additional information

Additional information

Synonyms	5-(Dimethylamino)naphthalene-1-sulfonyl chloride, DNSC, DNS chloride, DNSCl, NSC 83616
Purity	≥98% (HPLC)
Appearance	Yellow to orange powder
CAS-Number	605-65-2
Molecular Formula	C12H12ClNO2S
Molecular Weight	269.75
Identity	1H-NMR
Solvents	DMF, acetone, chloroform, pyridine, benzene or dioxane, water (insoluble), DMSO solutions (unstable)
Melting Point	72-74 °C (lit.)
Smiles	CN(C)C1=C(C=CC=C2S(=O)(Cl)=O)C2=CC=C1
InChi Key	XPDXVDYUQZHFPV-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H314
Precautionary statements	P280-P305 + P351 + P338-P310
GHS Symbol	GHS05
Signal word	Danger
RIDADR	UN3261 8
Transportation	Packing Group II
References	(1) R.E. Boyle, J. Org. Chem. 31, 3880 (1966), (2) R.F. Chen, Anal. Biochem. 25, 412 (1968), (3) T. Kinoshita, et al., Chem. Pharm. Bull. 22, 2413 (1974), (4) A.F. Sikorski & R.B. Daczynska, Biochim. Biophys. Acta 690, 302 (1982), (5) R.F. Chen & C.H. Scott, Anal. Lett. 18, 393 (1985), (6) J.M. Walker, Methods Mol. Biol. 32, 321 (1994), (7) K.J. Hunter, Methods Mol. Biol. 79, 119 (1998), (8) H. Yamada, et al., Biol. Pharm. Bull. 21, 778 (1998), (9) T. Takeuchi, J. Chromatogr. Lib. 70, 229 (2005), (10) T. Santa, Biomed. Chromatogr. 25, 1 (2011)
Quantity	1 g, 5 g, Bulk