2127-10-8

Basic information

• Product Name: 2,2'-DITHIOBIS(5-NITROPYRIDINE)
• Synonyms: DTNP;BIS(5-NITRO-2-PYRIDYL) DISULFIDE;2,2'-DITHIOBIS(5-NITROPYRIDINE);2,2’-dithiobis(5-nitro-pyridin;1,2-Bis(5-nitropyridin-2-yl)disulfane;Bis(5-nitro-2-pyridyl) disulfide, DTNP;5-nitro-2-(5-nitropyridin-2-yl)disulfanylpyridine;5-nitro-2-(5-nitropyridin-2-yl)disulfanyl-pyridine
• CAS NO: 2127-10-8
• Molecular Formula: C₁₀H₆N₄O₄S₂
• Molecular Weight: 310.31
• EINECS: 218-344-7
• Product Categories: blocks;Pyridines
• Mol File: 2127-10-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 155-157 °C(lit.)
• Boiling Point: 139°C (rough estimate)
• Flash Point: 264.8°C
• Appearance: /
• Density: 1.6508 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store at RT.
• PKA: -2.88±0.29(Predicted)
• BRN: 305413
• CAS DataBase Reference: 2,2'-DITHIOBIS(5-NITROPYRIDINE)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DITHIOBIS(5-NITROPYRIDINE)(2127-10-8)
• EPA Substance Registry System: 2,2'-DITHIOBIS(5-NITROPYRIDINE)(2127-10-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36/37/39
• WGK Germany: 3
• RTECS: UT2964000
• Hazardous Substances Data: 2127-10-8(Hazardous Substances Data)

Usage

Description

2,2'-Dithiobis(5-nitropyridine), also known as an aromatic disulphide, is a chemical compound that possesses unique properties due to its disulphide bond and nitro groups. It is widely utilized in various applications across different industries, particularly in the field of biochemistry and pharmaceuticals.

Uses

Used in Biochemical Research:
2,2'-Dithiobis(5-nitropyridine) is used as a cysteine-activating reagent for studying the Nuclear Magnetic Resonance (NMR) of G protein-coupled receptors. This application aids in the deprotection assays for protected selenocysteine-containing peptides, which is crucial for understanding the structure and function of these receptors.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2'-Dithiobis(5-nitropyridine) serves as a reagent for deprotecting p-methoxybenzyl groups and acetamidomethyl groups from the side-chains of cysteine and selenocysteine. This process is essential for the synthesis and development of various therapeutic agents, as it allows for the proper functionalization and modification of these molecules.
Additionally, 2,2'-Dithiobis(5-nitropyridine) is employed to remove the p-methoxybenzyl protecting group from cysteine and selenocysteine side-chains. This step is vital in the synthesis of peptides and proteins, ensuring that the desired functional groups are accessible for further modification or interaction with other molecules.

Upstream product

• 2127-09-5 2-mercapto-5-nitropyridine 
• 4548-45-2 2-chloro-5-nitropyridine 
• 5418-51-9 5-nitro-2-hydroxypyridine 
• 456-24-6 2-Fluoro-5-nitropyridine 

Downstream Products

• 27885-56-9 5-amino-2-thiolpyridine 
• 174467-01-7 9-[(2R,3S,4S,5R)-3-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(5-nitro-pyridin-2-yldisulfanyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one 
• 195967-03-4 3'-deoxy-5'-O-dimethoxytrityl-3'-S-(5-nitropyridyl-2-disulfanyl)thymidine 
• 174467-02-8 9-<5-O-(monomethoxytrityl)-3-deoxy-3-S-(5-nitropyridyl-2-disulfanyl)-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>hypoxanthine 
• 174485-82-6 5-nitro-pyridine-2-sulfonyl chloride 
• 1052111-32-6 5-(5-nitropyridin-2-yldithio)-1-phenyl-1H-tetrazole 
• 947509-70-8 Br^(1-)*C₂₇H₂₆N₂O₂PS₂⁽¹⁺⁾ 
• 129690-37-5 tin(5-nitropyridine-2-thiolate)3(phenylselenolate) 
• 129690-36-4 tin(5-nitropyridine-2-thiolate)2(phenylselenolate)2 
• 129715-55-5 tin(5-nitropyridine-2-thiolate)(phenylselenolate)3 

Relevant articles and documents

Silver-induced self-immolative Cl-F exchange fluorination of arylsulfur chlorotetrafluorides: Synthesis of arylsulfur pentafluorides

A novel strategy for the synthesis of arylsulfur pentafluorides by silver carbonate-induced Cl-F exchange fluorination of arylsulfur chlorotetrafluorides is reported. This fluorination does not require any exogenous fluoride sources. Rather, the reaction proceeds via the self-immolation of the substrate Ar-SF4Cl.

NOVEL PEPTIDE COMPOUND

A novel compound of the formula (1): wherein X is a tyrosine residue or a methionine residue; Y and Z each are a single bond or the like; R1 is a hydrogen atom or the like; R2 is a hydroxy group or the like; R3 is a hydrogen atom, alkyl group, amino group or the like; R4 is a hydrogen atom, alkyl group, carboxy group or the like; m is 1 or 2; and n is an integer of 0 to 2, with the proviso that when n is 0, R3 is a hydrogen atom or an alkyl group, or a pharmaceutically acceptable salt thereof, and its use in cancer immunotherapy.

Base-protected nucleotide analogs with protected thiol groups

The present invention is directed to protected thiol analogs of pyrimidine bases for syntheses of DNA and RNA by chemical or enzymatic methods. The subject analogs include reagents suitable for DNA or RNA synthesis via phosphoramidite, H-phosphonate or phosphotriester chemistry as well a reagents suitable for use by RNA and DNA polymerase, including thermostable polymerases employed by PCR or other nucleic acid amplification techniques. The nucleotide analogs synthesized by methods of this invention can thus be incorporated into oligonucleotides or polynucleotides, deprotected and derivatized with a functional group. In some cases the protecting groups are themselves antigenic and may be left on the oligonucleotides or polynucleotides for detection with antibodies. A method of synthesizing oligonucleotides with a functional group using the subject nucleotide analogs is also provided.