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{{chembox {{chembox
|Watchedfields = changed
| verifiedrevid = 443339224 |verifiedrevid = 477204496
⚫ | Name = 1,2-Ethanedithiol
|Name = Ethane-1,2-dithiol
| ImageFile = Ethanedithiol.png
⚫ |ImageFile = Ethanedithiol.png
| ImageSize = 150px |ImageSize = 150px
| ImageName = 1,2-Ethanedithiol
| ImageFile1 = Ethane-1,2-dithiol-3D-balls.png |ImageName = Ethane-1,2-dithiol
|ImageFile1 = Ethane-1,2-dithiol-3D-balls.png
| ImageSize1 = 150px |ImageSize1 = 150px
| ImageName1 = Ball-and-stick model of ethane-1,2-dithiol |ImageName1 = Ball-and-stick model of ethane-1,2-dithiol
| ImageFile2 = Ethane-1,2-dithiol-3D-vdW.png |ImageFile2 = Ethane-1,2-dithiol-3D-vdW.png
| ImageSize2 = 150px |ImageSize2 = 150px
| ImageName2 = Space-filling model of ethane-1,2-dithiol |ImageName2 = Space-filling model of ethane-1,2-dithiol
| IUPACName = Ethane-1,2-dithiol |PIN = Ethane-1,2-dithiol
| OtherNames = Dimercaptoethane<br />1,2-Ethanedithiol |OtherNames = Dimercaptoethane<br />1,2-Ethanedithiol
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} |UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 92T634FLAR |UNII = 92T634FLAR
| SMILES = SCCS |SMILES = SCCS
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13865015 |ChemSpiderID = 13865015
|PubChem = 10902
⚫ | InChI = 1/C2H6S2/c3-1-2-4/h3-4H,1-2H2
|EC_number = 208-752-3
⚫ | InChIKey = VYMPLPIFKRHAAC-UHFFFAOYAA
⚫ |InChI = 1/C2H6S2/c3-1-2-4/h3-4H,1-2H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ |InChIKey = VYMPLPIFKRHAAC-UHFFFAOYAA
⚫ | StdInChI = 1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChI = 1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2
⚫ | StdInChIKey = VYMPLPIFKRHAAC-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChIKey = VYMPLPIFKRHAAC-UHFFFAOYSA-N
⚫ | CASNo = 540-63-6
|CASNo_Ref = {{cascite|correct|CAS}}
⚫ | RTECS = KI3325000
⚫ |CASNo = 540-63-6
⚫ }}
⚫ |RTECS = KI3325000
⚫ | Section2 = {{Chembox Properties
⚫ }}
| C=2|H=6|S=2
⚫ |Section2={{Chembox Properties
⚫ | Appearance = Colorless liquid
| Density = 1.123 g/cm³ | C=2 | H=6 | S=2
⚫ |Appearance = Colorless liquid
⚫ | Solubility = Slightly sol
|Density = 1.123 g/cm{{sup|3}}
⚫ | Solvent = other solvents
⚫ |Solubility = Slightly sol
⚫ | SolubleOther = Good solubility in<br />most organic solvents
⚫ |Solvent = other solvents
⚫ | MeltingPtC = -41
⚫ |SolubleOther = Good solubility in<br />most organic solvents
| BoilingPtC = 146
⚫ |MeltingPtC = -41
⚫ | Boiling_notes = 46 mmHg
| pKa = ~11 |BoilingPtC = 146
⚫ |BoilingPt_notes = 46 mmHg
| pKb =
|pKa = ≈11
| Viscosity =
| RefractIndex = 1.5589 (D-line, 25 °C) |RefractIndex = 1.5589 (D-line, 25 °C)
}} }}
| Section3 = {{Chembox Structure |Section7={{Chembox Hazards
⚫ |NFPA-H = 2
| Dipole =
⚫ |NFPA-F = 2
⚫ }}
|FlashPtC = 50
| Section7 = {{Chembox Hazards
|GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}
| ExternalMSDS =
|GHSSignalWord = Danger
| EUClass = Toxic ('''T''')
|HPhrases = {{H-phrases|226|301|302|310|312|319|330}}
⚫ | NFPA-H = 2
|PPhrases = {{P-phrases|210|233|240|241|242|243|260|262|264|270|271|280|284|301+310|301+312|302+350|302+352|303+361+353|304+340|305+351+338|310|312|320|321|322|330|337+313|361|363|370+378|403+233|403+235|405|501}}
⚫ | NFPA-F = 2
⚫ }}
| NFPA-R =
⚫ |Section8={{Chembox Related
| FlashPt = 50 °C
⚫ |OtherFunction_label = ]s
| RPhrases = {{R10}} {{R22}}
⚫ |OtherFunction = ]; ]; ]; ]; ]
| SPhrases = {{S16}}
}} }}
⚫ | Section8 = {{Chembox Related
⚫ | Function = ]s
⚫ | OtherFunctn = ]; ]; ]; ]
}}
}} }}


'''1,2-Ethanedithiol''' is a colorless liquid with the formula C<sub>2</sub>H<sub>4</sub>(SH)<sub>2</sub>. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in ] and an excellent ligand for metal ions. '''Ethane-1,2-dithiol''', also known as '''EDT''',<ref>{{Cite journal|last=Choi|first=H.|last2=Aldrich|first2=J.v.|date=1993-07-01|title=Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine|journal=International Journal of Peptide and Protein Research|language=en|volume=42|issue=1|pages=58–63|doi=10.1111/j.1399-3011.1993.tb00350.x|pmid=8103765|issn=1399-3011}}</ref> is a colorless ] with the ] ]{{sub|2}}]{{sub|4}}(]){{sub|2}}. It has a very characteristic odor which is compared by many people to rotten ]. It is a common building block in ] and an excellent ] for metal ions.


==Preparation== ==Preparation==
1,2-Ethanedithiol is commercially available. It can be prepared by the action of ] on ] followed by ].<ref>{{OrgSynth | author = Speziale, A. J. | title = Ethanedithiol | collvol = 4 | collvolpages = 401 | year = 1963 | prep = cv4p0401}}</ref> Ethane-1,2-dithiol is made commercially by the reaction of ] with aqueous ]. In the laboratory, it can also be prepared by the action of ] on ] followed by ].<ref>{{OrgSynth | author = Speziale, A. J. | title = Ethanedithiol | collvol = 4 | collvolpages = 401 | year = 1963 | prep = cv4p0401}}</ref>


==Applications== ==Applications==
This compound is widely used in organic chemistry because it reacts with ]s and ]s to give 1,3-]s, which are useful intermediates. As a 1,2-], this compound is widely used in organic chemistry because it reacts with ]s and ]s to give 1,3-]s, which are useful intermediates.
<ref>R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289}}</ref> <ref>R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289X}}</ref>


::C<sub>2</sub>H<sub>4</sub>(SH)<sub>2</sub> + RR'CO → C<sub>2</sub>H<sub>4</sub>S<sub>2</sub>CRR' + H<sub>2</sub>O ::C{{sub|2}}H{{sub|4}}(SH){{sub|2}} + RR'CO → C{{sub|2}}H{{sub|4}}S{{sub|2}}CRR' + H{{sub|2}}O


] ]


Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). ]s such as ] undergo analogous reactions to 1,3-]s and 1,3-]s. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated. Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). ]s such as ] undergo analogous reactions to 1,3-]s and 1,3-]s. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.

1,2-Ethanedithiol is commonly used as a scavenger in peptide cleavage synthesis.

== See also ==
*]


==References== ==References==
<references /> <references />


{{DEFAULTSORT:Ethanethiol, 1,2-}} {{DEFAULTSORT:Ethanedithiol, 1, 2-}}
] ]
] ]
] ]
]

] ]
]
]

Latest revision as of 02:15, 3 July 2024

Ethane-1,2-dithiol
Ethane-1,2-dithiol
Ball-and-stick model of ethane-1,2-dithiol
Space-filling model of ethane-1,2-dithiol
Names
Preferred IUPAC name Ethane-1,2-dithiol
Other names Dimercaptoethane
1,2-Ethanedithiol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.958 Edit this at Wikidata
EC Number
  • 208-752-3
PubChem CID
RTECS number
  • KI3325000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2Key: VYMPLPIFKRHAAC-UHFFFAOYSA-N
  • InChI=1/C2H6S2/c3-1-2-4/h3-4H,1-2H2Key: VYMPLPIFKRHAAC-UHFFFAOYAA
SMILES
  • SCCS
Properties
Chemical formula C2H6S2
Molar mass 94.19 g·mol
Appearance Colorless liquid
Density 1.123 g/cm
Melting point −41 °C (−42 °F; 232 K)
Boiling point 146 °C (295 °F; 419 K) 46 mmHg
Solubility in water Slightly sol
Solubility in other solvents Good solubility in
most organic solvents
Acidity (pKa) ≈11
Refractive index (nD) 1.5589 (D-line, 25 °C)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H226, H301, H302, H310, H312, H319, H330
Precautionary statements P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+P310, P301+P312, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
2 2
Flash point 50 °C (122 °F; 323 K)
Related compounds
Related thiols 1,1-Ethanedithiol; Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol
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

Ethane-1,2-dithiol, also known as EDT, is a colorless liquid with the formula C2H4(SH)2. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.

Preparation

Ethane-1,2-dithiol is made commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.

Applications

As a 1,2-dithiol, this compound is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates.

C2H4(SH)2 + RR'CO → C2H4S2CRR' + H2O
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using ethane-1,2-dithiol
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using ethane-1,2-dithiol

Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to 1,3-dioxolanes and 1,3-dioxanes. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.

1,2-Ethanedithiol is commonly used as a scavenger in peptide cleavage synthesis.

See also

References

  1. Choi, H.; Aldrich, J.v. (1993-07-01). "Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine". International Journal of Peptide and Protein Research. 42 (1): 58–63. doi:10.1111/j.1399-3011.1993.tb00350.x. ISSN 1399-3011. PMID 8103765.
  2. Speziale, A. J. (1963). "Ethanedithiol". Organic Syntheses; Collected Volumes, vol. 4, p. 401.
  3. R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X
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