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2,2'-Dipyridyldisulfide: Difference between revisions

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Revision as of 11:17, 11 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 15:33, 15 May 2024 edit undoMarbletan (talk | contribs)Extended confirmed users5,564 editsmNo edit summary 
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{{orphan|date=December 2008}}
{{chembox {{chembox
| verifiedrevid = 413095043
| Name = 2,2'-Dipyridyldisulfide | Name = 2,2′-Dipyridyldisulfide
| ImageFile = 2,2'-Dipyridyldisulfide.svg | ImageFile = 2,2'-Dipyridyldisulfide.svg
| ImageAlt = Skeletal formula of DPS
<!-- | ImageSize = 188px -->
| IUPACName = 2,2'-Dipyridyldisulfide | ImageFile1 = 2,2'-Dipyridyldisulfide-3D-spacefill.png
| ImageAlt1 = Space-filling model of the DPS molecule
| OtherNames = 2,2'-Dipyridyldisulphide<br />Aldrithiol-2
| PIN = 2,2′-Disulfanediyldipyridine
| OtherNames = 1,2-Di(pyridin-2-yl)disulfane (not recommended)<br />2,2′-Dipyridyldisulfide<br />2,2′-Dipyridyldisulphide<br />Aldrithiol-2
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 58603 | ChemSpiderID = 58603
| InChI = 1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H | InChI = 1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
| InChIKey = HAXFWIACAGNFHA-UHFFFAOYAJ | InChIKey = HAXFWIACAGNFHA-UHFFFAOYAJ
| SMILES1 = c1ccnc(c1)SSc2ccccn2 | SMILES1 = c1ccnc(c1)SSc2ccccn2
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEBI = 143170
| ChEMBL = 118678
| PubChem = 65093
| EC_number = 218-343-1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H | StdInChI = 1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HAXFWIACAGNFHA-UHFFFAOYSA-N | StdInChIKey = HAXFWIACAGNFHA-UHFFFAOYSA-N
| CASNo = 2127-03-9 | CASNo = 2127-03-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L6X912UPBU
| SMILES = S(Sc1ncccc1)c2ncccc2 | SMILES = S(Sc1ncccc1)c2ncccc2
}} }}
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| Formula = |C=10|H=8|N=2|S=2 | Formula = |C=10|H=8|N=2|S=2
| MolarMass = | MolarMass =
| MeltingPtCL= 56 | MeltingPtC = 56 to 58
| MeltingPtCH = 58
}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| MainHazards = Irritant ('''Xi''') | MainHazards = Irritant ('''Xi''')
| RPhrases = {{R36/37/38}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| SPhrases = {{S36/37/39}}
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}} }}
}} }}
'''2,2'-Dipyridyldisulfide''', sometimes known as DPS, is used for preparing thiols<ref>{{cite journal | author = Futaki S. and Kitagawa K. | title = Peptide-Unit Assembling Using Disulfide Cross-Linking - a New Approach for Construction of Protein Models | year = 1994 | journal = ] | volume = 35 | issue = 8 | pages = 1267–1270 | doi=10.1016/0040-4039(94)88040-9}}</ref><ref>{{cite journal | journal = ] | title = Special Reagents for Thiol Groups | volume = 4 | issue = 3 | pages = 33–46}}</ref> and activating or protecting ] with ] in the following reaction.<ref>{{cite journal | journal = ] | author = Thalmann A., Oertle K. and Gerlach H | title = Synthesis of ricinelaidic acid lactone| volume = 7 | pages = 470}}</ref> '''2,2′-Dipyridyldisulfide''', sometimes known as DPS, is used for preparing thiols<ref>{{cite journal | author = Futaki S. and Kitagawa K. | title = Peptide-Unit Assembling Using Disulfide Cross-Linking - a New Approach for Construction of Protein Models | year = 1994 | journal = ] | volume = 35 | issue = 8 | pages = 1267–1270 | doi=10.1016/0040-4039(94)88040-9}}</ref><ref>{{cite journal | journal = ] | title = Special Reagents for Thiol Groups | volume = 4 | issue = 3 | pages = 33–46}}</ref> and activating ] for ]s, as in the following reaction:<ref>{{cite journal | journal = ] | author = Thalmann A., Oertle K. and Gerlach H | title = Ricinelaidic acid lactone| year = 1985 | volume = 7 | pages = 470 |doi= 10.15227/orgsyn.063.0192}}</ref>
] :]


==Uses== ==Uses==


It is also used in molecular biology as an ], for example to oxidise free thiols to form disulfide bonds in proteins. It is also used in molecular biology as an ], for example to oxidise free ]s to form ]s in proteins.


==References== ==References==
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{{DEFAULTSORT:Dipyridyldisulfide, 2,2'-}} {{DEFAULTSORT:Dipyridyldisulfide, 2,2'-}}
] ]
] ]
] ]


Latest revision as of 15:33, 15 May 2024

2,2′-Dipyridyldisulfide
Skeletal formula of DPS
Space-filling model of the DPS molecule
Names
Preferred IUPAC name 2,2′-Disulfanediyldipyridine
Other names 1,2-Di(pyridin-2-yl)disulfane (not recommended)
2,2′-Dipyridyldisulfide
2,2′-Dipyridyldisulphide
Aldrithiol-2
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.676 Edit this at Wikidata
EC Number
  • 218-343-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8HKey: HAXFWIACAGNFHA-UHFFFAOYSA-N
  • InChI=1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8HKey: HAXFWIACAGNFHA-UHFFFAOYAJ
SMILES
  • S(Sc1ncccc1)c2ncccc2
  • c1ccnc(c1)SSc2ccccn2
Properties
Chemical formula C10H8N2S2
Molar mass 220.31 g·mol
Melting point 56 to 58 °C (133 to 136 °F; 329 to 331 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant (Xi)
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2,2′-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols and activating carboxylic acid for coupling reactions, as in the following reaction:

Uses

It is also used in molecular biology as an oxidising agent, for example to oxidise free thiols to form disulfide bonds in proteins.

References

  1. Futaki S. and Kitagawa K. (1994). "Peptide-Unit Assembling Using Disulfide Cross-Linking - a New Approach for Construction of Protein Models". Tetrahedron Lett. 35 (8): 1267–1270. doi:10.1016/0040-4039(94)88040-9.
  2. "Special Reagents for Thiol Groups". Aldrichimica Acta. 4 (3): 33–46.
  3. Thalmann A., Oertle K. and Gerlach H (1985). "Ricinelaidic acid lactone". Org. Synth. 7: 470. doi:10.15227/orgsyn.063.0192.


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