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109-80-8 - 1,3-Propanedithiol, 97% - Trimethylene mercaptan - A15261 - Alfa Aesar

A15261 1,3-Propanedithiol, 97%

Numéro CAS
109-80-8
Synonymes
Trimethylene mercaptan

Dimensions Prix ($) Quantité Disponibilité
5g 16,56
25g 49,95
100g 125,58
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1,3-Propanedithiol, 97%

MDL
MFCD00004904
EINECS
203-706-9

Propriétés chimiques

Formule
HS(CH2)3SH
Poids formulaire
108.23
Point de fusion
-79°
Point d'ébullition
168-170°
Point d'éclair
63°(145°F)
Densité
1.077
Indice de réfraction
1.5400
Solubilité
Slightly soluble in water. Miscible with alcohol, ether, chloroform, etherMiscible with alcohol, ether, chloroform and ether. Slightly miscible with water.

Applications

1,3-Propanedithiol is used as a reagent in the preparation of thioketals and thioacetals. It acts as a flavoring agent. It is used as a precursor in the synthesis of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds. It is involved in the preparation of diiron propanedithiolate hexacarbonyl by reacting reaction with triiron dodecacarbonyl. Further, it is used for the protection of aldehydes and ketones through their reversible formation of dithianes. In addition to this, it reacts with metal ions to form chelate rings.

Notes

Store in a cool place. Incompatible with bases, oxidizing agents, reducing agents and alkali metals.

Références bibliographiques

Precursor of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds. The protection step is catalyzed by Lewis acids, e.g. BF3 etherate: Tetrahedron Lett., 871 (1971), TiCl4: Tetrahedron Lett., 24, 1289 (1983), Aluminum trifluoromethanesulfonate, B20785, or Indium(III)­ trifluoromethanesulfonate, 40131. Diothioacetalization can be accomplished under neutral, solvent-free conditions using Lithium trifluoromethanesulfonate, 39322, as catalyst: Tetrahedron Lett., 40, 4055 (1999). For the preparation of monocyclic dithioacetals of ß-diketones at low temperature in the presence of BF3 etherate, see: Tetrahedron, 44, 2283 (1988).

Alternatively, 1,3-dithianes can be prepared by alkylation with reactive gem-dihalides under phase-transfer conditions: Liebigs Ann. Chem., 1589 (1982).

For deprotection methods and uses of 1,3-dithianes as acyl anion equivalents, see: 1,3-Dithiane, A10505.

Wang, L.; Li, R.; Feng, L.; Liu, J.; Gao, X.; Wang, W. Study on the interface electronic states of chemically modified ZnO nanowires. RSC Adv. 2015, 5 (119), 98130-98135.

Kuciński, K.; Pawlu?, P.; Marciniec, B.; Hreczycho, G. Highly Selective Hydrothiolation of Unsaturated Organosilicon Compounds Catalyzed by Scandium(III) Triflate. Chem. Eur. J. 2015, 21 (13), 4940-4943.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335-H227

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

Mentions de prudence: P210-P261-P280-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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. 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.

Autres références

Merck
14,7801
Beilstein
1071197
Classe de danger
9
Code tarifaire harmonisé
2930.90
TSCA
Yes
RTECS
TZ2585500

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