2-(Trimethylsilyl)ethanethiol
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Grundinformationen
- CAS
18143-30-1- Standard-SMILES
C[Si](C)(C)CCS- InChIKey
BCOLNMGFOWHFNI-UHFFFAOYSA-N- Summenformel
- C5H14SSi
- Durchschnittliche Molmasse
- 134,32 g/mol
- Monoisotopische Masse
- 134,05854815
Namen und Bezeichner
- Bevorzugter Name
- 2-(Trimethylsilyl)ethanethiol
- IUPAC
- 2-trimethylsilylethanethiol
- Englischer Name
- (2-MERCAPTOETHYL)TRIMETHYLSILANE
- Summenformel
- C5H14SSi
- Molmasse
- 134.32
Namen und Synonyme
2-(Trimethylsilyl)ethanethiol18143-30-1DTXSID10171139RefChem:84910DTXCID5093630628-469-22-trimethylsilylethanethiol(2-Mercaptoethyl)trimethylsilaneEthanethiol, 2-(trimethylsilyl)-2-trimethylsilanyl-ethanethiol2-(trimethylsilyl)ethane-1-thiolMFCD00077888
Weitere Namen anzeigen
BESTETHYLTHIOTRIMETHYLSILANE 97%2-(trimethylsilyl)-ethanethio2-(trimethylsiliconalkaneyl)ethylthiol(2-Mercaptoethyl)trimethylsilane, BEST
BRN 17321264-04-00-03952 (Beilstein Handbook Reference)EN300-814248Silane, (2-mercaptoethyl)trimethyl-FT-0721903trimethylsilylethyl mercaptan2-Trimethylsilylethane thiolSCHEMBL190805
Datenbank-Bezeichner
- CAS
18143-30-1- PubChem CID
- 205521
- DTXSID
DTXSID10171139- EC Number
- 628-469-2
- Nikkaji
- J49.807F
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- Polarare Oberfläche (TPSA)
- 1 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 46
Physikochemische Eigenschaften
- Siedepunkt
- 144 · 144-146 °C(lit.)
- Dichte
- 0.839 g/mL · 0.839 g/mL at 25 °C(lit.)
- Brechungsindex
- 20 · n20/D 1.454(lit.)
- Flammpunkt
- 85 °F · 85 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 2 Cl2, · Soluble in MeOH, CH2Cl2, THF, and most organic solvents.
- pka
- 10.8 · 10.80±0.10(Predicted)
- Aggregatzustand
- liquid
- BRN
- 1732126 · 1732126
- InChI
- 1S/C5H14SSi/c1-7(2,3)5-4-6/h6H,4-5H2,1-3H3
- InChIKey
- BCOLNMGFOWHFNI-UHFFFAOYSA-N
- SMILES
- C[Si](C)(C)CCS
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Hazard Classes and CategoriesFlam. Liq. 3 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)
Sicherheitsdaten
- F
- 13
- wgk
- 3
- ridadr
- UN 1993 3/PG 3
- RTECS-Nr.
- KJ2621000
- risk_code
- 10-36/37/38
- Toxizität
- mouse,LD50,intraperitoneal,2500mg/kg (2500mg/kg),Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 229, Pg. 1011, 1976.
Chemie und Industrie
Anwendungen
Verwenden2-(Trimethylsilyl)ethanethiol is a reagent used as a monoprotected sulfide dianion equivalent for the two-step installation of a divalent sulfur atom into organic molecules. It participates in the reactions of Thiol Substitution Reactions, Source of Sulfur Acid Derivatives, etc.
Darstellung
synthetischeThe high commercial cost of 2-(trimethylsilyl)ethanethiol necessitates methods for its lab scale synthesis. The radical addition of thiolacetic acid to vinyltrimethylsilane occurs thermally to afford a 9:1 ratio of regioisomers, the 1- and 2-(trimethylsilyl)ethyl thiolesters of acetic acid (eq 1). Photochemical initiation may improve the ratio of regioisomers obtained. Purification of the thiolacetate by careful fractional distillation should be performed prior to conversion to the thiol in order to ensure high purity. The conversion to thiol is best performed with LAH3 or methanolic K2CO3, but ammonolysis may also be suitable. Saponification with KOH in water/ethanol is slightly less efficient. Direct radical addition of liquid H2S to vinyl trimethylsilane has been demonstrated, but the procedure is low-yielding and inconvenient.
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