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2127-03-9 - 2,2'-Dipyridyl disulfide, 98% - 2,2'-Dithiodipyridine - A11118 - Alfa Aesar

A11118 2,2'-Dipyridyl disulfide, 98%

CAS-Nummer
2127-03-9
Synonyme
2,2'-Dithiodipyridine

Größe Preis ($) Menge Verfügbarkeit
5g 52,37
25g 176,13
100g 555,17
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2,2'-Dipyridyl disulfide, 98%

MDL
MFCD00006287
EINECS
218-343-1

Chemische Eigenschaften

Formel
C10H8N2S2
Molmasse
220.32
Schmelzpunkt
56-59°
Flammpunkt
210°(410°F)
Löslichkeit
Soluble in water, benzene, tetrahydrofuran, dichloromethane, acetonitrile and dimethyformamide.

Anwendungen

2,2'-Dipyridyl disulfide is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides.

Bemerkungen

Incompatible with oxidizing agents and metals.

Literaturverweise

In combination with triphenylphosphine, acts as a peptide coupling reagent (see Appendix 6) in which water is removed by a mechanism whereby the phosphine is oxidized to the phosphine oxide and the disulfide reduced to the thiol: J. Am. Chem. Soc., 90, 4490 (1968); 91, 1554 (1969); Bull. Chem. Soc. Jpn., 43, 1271 (1970).

The technique has also been widely applied for macrolactonization, via high-dilution cyclization of the 2-pyridine thioester: J. Am. Chem. Soc., 96, 5614 (1974); 97, 653, 654, 2287 (1975). The cyclization step can be catalyzed by silver ion: Helv. Chim. Acta, 57, 2661 (1974). See, e.g.: Org. Synth. Coll., 7, 470 (1990).

In combination with tri-n-butylphosphine has been used for the activation of glycosides, e.g. in the formation of disaccarides: J. Am. Chem. Soc., 103, 4221 (1981); Tetrahedron, 47, 6435 (1991).

Moosun, S.; Laulloo, S. J.; Bhowon, M. G. Metal complexes of diaryl and 2, 2'-dipyridyl disulfides. J. Sulphur Chem. 2012, 33 (6), 661-691.

Bhasin, K. K.; Kumar, R.; Mehta, S. K.; Raghavaiah, P.; Jacob, C.; Klapotke, T. M. Synthesis and characterization of 5, 5'-dibromo-2, 2'-dipyridyl disulfide and some of its derivatives: X-ray structure of 5, 5'-dibromo-2, 2'-dipyridyl disulfide and bis (5-bromopyridine-2-ylthio) methane. Inorg. Chim. Acta 2009, 362 (7), 2386-2390.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
154629
Harmonized Tariff Code
2933.39
TSCA
Yes

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