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{{short description|Chemical compound}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 456364861 | verifiedrevid = 477205579
| Name = 1,3-Propanedithiol | Name = 1,3-Propanedithiol
| ImageFile = H2pdt.png | ImageFile = 1,3-Propandithiol Structural Formula V1.svg
| ImageSize = 100px | ImageSize = 200px
| ImageName = 1,3-Propanedithiol | ImageName = 1,3-Propanedithiol
⚫ | ImageFile1 = 1,3-Propanedithiol-3D-balls.png
⚫ | IUPACName = Propane-1,3-dithiol
| OtherNames = 1,3-dimercaptopropane | ImageAlt1 = 1,3-Propanedithiol molecule
⚫ | PIN = Propane-1,3-dithiol
⚫ | Section1 = {{Chembox Identifiers
| OtherNames = 1,3-Dimercaptopropane
⚫ | SMILES = SCCCS
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SMILES = SCCCS
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 44864 | ChEBI = 44864
Line 17: Line 20:
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1235209 | ChEMBL = 1235209
| PubChem = 8013
| EC_number = 203-706-9
| UNNumber = 3336
| UNII = R4LUJ82U52
| InChI = 1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 | InChI = 1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2
| InChIKey = ZJLMKPKYJBQJNH-UHFFFAOYAS | InChIKey = ZJLMKPKYJBQJNH-UHFFFAOYAS
Line 25: Line 32:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109-80-8 | CASNo = 109-80-8
| RTECS = TZ2585500 | RTECS = TZ2585500
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=3|H=8|S=2 | C=3 | H=8 | S=2
| Appearance = Colorless liquid | Appearance = Colorless liquid
| Density = 1.078 g/cm³ | Density = 1.078 g/cm<sup>3</sup>
| Solubility = slight | Solubility = slight
| Solvent = solvents | Solvent = solvents
| SolubleOther = all organic solvents | SolubleOther = all organic solvents
| MeltingPtC = -79 | MeltingPtC = -79
| BoilingPtC = 169 | BoilingPtC = 169
| pKb = | pKb =
| RefractIndex = 1.539 | RefractIndex = 1.539
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| Dipole = 0 ] | Dipole = 0 ]
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| MainHazards = stench | MainHazards = stench
| FlashPt = 138 °F | FlashPtC = 138
| RPhrases = {{R36/37/38}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| SPhrases = {{S26}}
| HPhrases = {{H-phrases|302|315|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCpds = ]<br />]<br />] | OtherCompounds = ]<br />]<br />]
}} }}
}} }}
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==Use in organic synthesis== ==Use in organic synthesis==
1,3-Propanedithiol is mainly used for the ] of ]s and ]s via their reversible formation of ]s.<ref>{{cite encyclopedia 1,3-Propanedithiol is mainly used for the ] of ]s and ]s via their reversible formation of ]s.<ref>{{cite encyclopedia
| author = Conrow, R. E.; Le Huérou, Y. |author1=Conrow, R. E. |author2=Le Huérou, Y. | title = 1,3-Propanedithiol
⚫ | encyclopedia=Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette)
⚫ | title = 1,3-Propanedithiol
⚫ | year = 2004
⚫ | encyclopedia=Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette)
⚫ | publisher = J. Wiley & Sons, New York
⚫ | year = 2004
| doi = 10.1002/047084289X| hdl = 10261/236866
⚫ | publisher = J. Wiley & Sons, New York
|isbn=9780471936237 | hdl-access = free
⚫ | doi = 10.1002/047084289}}
⚫ }}
</ref> A prototypical ] is its formation of 1,3-dithiane from ].<ref>{{OrgSynth </ref> A prototypical ] is its formation of 1,3-dithiane from ].<ref>{{OrgSynth
| author = Corey, E. J.; Seebach, D. | author = Corey, E. J.
| author2 = Seebach, D.
| title = 1,3-Dithiane | title = 1,3-Dithiane
| year = 1988 | year = 1988
| collvol = 6 | collvol = 6
| collvolpages = 556 | collvolpages = 556
| prep = cv6p0556}}</ref> The reactivity of this dithiane illustrates the concept of ]. | prep = cv6p0556}}</ref> The reactivity of this dithiane illustrates the concept of ]. Alkylation gives thioethers, e.g. ].


The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.<ref>{{cite journal The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.<ref>{{cite journal
| author = Liu, Q.; Che, G. Yu, H.; Liu, Y.; Zhang, J. Zhang, Q.; Dong, D. |author1=Liu, Q. |author2=Che, G. |author3=Yu, H. |author4=Liu, Y. |author5=Zhang, J. |author6=Zhang, Q. |author7=Dong, D. | title = The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
⚫ | journal = ]
| title = The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
| year = 2003
⚫ | journal = ]
| year = 2003 | volume = 68
| volume = 68 | pages = 9148–9150
⚫ | doi = 10.1021/jo034702t
| pages = 9148–9150
| pmid = 14604400
| doi = 10.1021/jo034702t
| pmid = 14604400 | issue = 23}}</ref>

| issue = 23}}</ref>
1,3-Propanedithiol is used in the synthesis of ].


==Use in inorganic synthesis== ==Use in inorganic synthesis==
1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the diiron derivative:<ref>{{cite journal 1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative ] upon reaction with ]:<ref>{{cite journal
| author = Winter, A.; Zsolnai, L. and Huttner, G. |author1=Winter, A. |author2=Zsolnai, L. |author3=Huttner, G. | title = Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden
⚫ | journal = Zeitschrift für Naturforschung
| title = Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden
| year = 1982
⚫ | journal = Zeitschrift für Naturforschung
| year = 1982 | volume = 37b
| volume = 37b | pages = 1430–1436
| doi =10.1515/znb-1982-1113
| pages = 1430–1436
|s2cid=98749484 | doi-access =free}}
| doi =
⚫ }}
</ref> </ref>
:] + C<sub>3</sub>H<sub>6</sub>(SH)<sub>2</sub> → Fe<sub>2</sub>(S<sub>2</sub>C<sub>3</sub>H<sub>6</sub>)(CO)<sub>6</sub> + H<sub>2</sub> + ] + CO :Fe<sub>3</sub>(CO)<sub>12</sub> + C<sub>3</sub>H<sub>6</sub>(SH)<sub>2</sub> → Fe<sub>2</sub>(S<sub>2</sub>C<sub>3</sub>H<sub>6</sub>)(CO)<sub>6</sub> + H<sub>2</sub> + Fe(CO)<sub>5</sub> + CO


==Safety== ==Safety==
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{{reflist}} {{reflist}}


{{DEFAULTSORT:Propanedithiol, 1,3-}}
] ]
] ]
]

Latest revision as of 04:13, 13 August 2023

Chemical compound
1,3-Propanedithiol
1,3-Propanedithiol
1,3-Propanedithiol molecule
Names
Preferred IUPAC name Propane-1,3-dithiol
Other names 1,3-Dimercaptopropane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.371 Edit this at Wikidata
EC Number
  • 203-706-9
PubChem CID
RTECS number
  • TZ2585500
UNII
UN number 3336
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2Key: ZJLMKPKYJBQJNH-UHFFFAOYSA-N
  • InChI=1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2Key: ZJLMKPKYJBQJNH-UHFFFAOYAS
SMILES
  • SCCCS
Properties
Chemical formula C3H8S2
Molar mass 108.22 g·mol
Appearance Colorless liquid
Density 1.078 g/cm
Melting point −79 °C (−110 °F; 194 K)
Boiling point 169 °C (336 °F; 442 K)
Solubility in water slight
Solubility in solvents all organic solvents
Refractive index (nD) 1.539
Structure
Dipole moment 0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards stench
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 138 °C (280 °F; 411 K)
Related compounds
Related compounds 1,2-ethanedithiol
1,2-propanedithiol
lipoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.

Use in organic synthesis

1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. The reactivity of this dithiane illustrates the concept of umpolung. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane.

The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.

1,3-Propanedithiol is used in the synthesis of tiapamil.

Use in inorganic synthesis

1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:

Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO

Safety

The stench of 1,3-propanedithiol can be neutralized with bleach.

See also

References

  1. Conrow, R. E.; Le Huérou, Y. (2004). "1,3-Propanedithiol". Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette). J. Wiley & Sons, New York. doi:10.1002/047084289X. hdl:10261/236866. ISBN 9780471936237.
  2. Corey, E. J.; Seebach, D. (1988). "1,3-Dithiane". Organic Syntheses; Collected Volumes, vol. 6, p. 556.
  3. Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. (2003). "The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization". Journal of Organic Chemistry. 68 (23): 9148–9150. doi:10.1021/jo034702t. PMID 14604400.
  4. Winter, A.; Zsolnai, L.; Huttner, G. (1982). "Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden". Zeitschrift für Naturforschung. 37b: 1430–1436. doi:10.1515/znb-1982-1113. S2CID 98749484.
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