2-Methylpropan-2-thiol
TBM · TERT-BUTYL MERCAPTAN · tert-Butylthiol · 2-Methylpropan-2-thiol · T-BUTYL MERCAPTAN · 2-Propanethiol, 2-methyl- · TERT-BUTANETHIOL · 2-Isobutanethiol
Identifikatoren & physikalische Daten
| CAS No. | 16528-55-5 |
|---|---|
| Summenformel | C4H10S |
| Durchschnittliche Molmasse | 90,19 g/mol |
| Monoisotopische Masse | 90,05032149 g/mol |
| SMILES | CC(C)(C)S |
| InChIKey | WMXCDAVJEZZYLT-UHFFFAOYSA-N |
| PubChem CID | 6387 |
| ChEMBL | CHEMBL3182458 |
| EC No. | 200-890-2 |
| DTXSID | DTXSID0026418 |
| Lokaler Name | 2-Methylpropan-2-thiol |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 25 |
| Geruch | Heavy skunk odorStrong offensive odor |
| Dichte | 0.8 (NFPA, 2010) - Less dense than waterwill float0.79426 at 25 °C/4 °CRelative density (water = 1): 0.800.8 g/mL at 25 °C(lit.) |
| Color/Form | Mobile liquidCOLORLESS LIQUID |
| Löslichkeit | Insoluble (NFPA, 2010)Slightly sol in watervery sol in alcohol, ether, liquid hydrogen sulfideVery soluble in acetonesoluble in carbon tetrachloride1.47g/l slightly solubleSlightly soluble in water |
| Flammpunkt | less than -20 °F (NFPA, 2010)<-20 °F (<-29 °C) (closed cup)-26 °C c.c.−12 °F |
| Siedepunkt | 149-153 °F at 760 mmHg (NFPA, 2010)63.7-64.2 °C64 °C62-65 °C(lit.) |
| Decomposition | The substance decomposes on burning producing toxic gases including sulfur oxides.When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of /sulfur oxides/. |
| Schmelzpunkt | -32 °F (ICSC, 2024)-0.5 °CHeat of fusion at melting point = 2.0782X10+7 J/kmol0 °C-1.1 °C |
| Dampfdichte | 3.1 (NFPA, 2010) - Heavier than airwill sink (Relative to Air)3.1 (Air= 1)Relative vapor density (air = 1): 3.13.1 (vs air) |
| Geruchsschwelle | Odor Threshold Low: 0.00081 [ppm]The Guide in the Emergency Response Guidebook is for "Butyl mercaptan." Odor threshold (100% recognition) from CHEMINFO0.000029ppm |
| Dampfdruck | 142.5 mmHg at 68 °F (ICSC, 2024)181.0 [mmHg]181 mm Hg at 25 °C /Extrapolated/Vapor pressure, kPa at 20 °C: 19.0303.5 mm Hg ( 37.7 °C) |
| Brechungsindex | Index of refraction: 1.41984 at 25 °C/Dn20/D 1.423(lit.) |
| Lagerbedingungen | Flammables area |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | pK1:11.22 (25°C,μ=0.1) |
| Farbe | Clear colorless |
| Geruch | sulfury |
| Merck | 14,1579 |
| BRN | 505947 |
| Henry-Konstante | 4.5×10-4 mol/(m3Pa) at 25℃, Plyasunova et al. (2004) |
| Dielektrizitätskonstante | 5.4800000000000004 |
| Stabilität | Stable. Flammable - note low flashpoint. Incompatible with strong oxidizing agents. |
| InChI | 1S/C4H10S/c1-4(2,3)5/h5H,1-3H3 |
| InChIKey | WMXCDAVJEZZYLT-UHFFFAOYSA-N |
| SMILES | CC(C)(C)S |
| LogP (Verteilungskoeffizient) | 2.206 (est) |
| CAS Datenbank | 75-66-1(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propanethiol, 2-methyl-(75-66-1) |
| EPA chemische Informationen | 2-Propanethiol, 2-methyl- (75-66-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (35.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]H304 (64.5%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]H317 (91.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (65%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H411 (27.2%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P210, P233, P240, P241, P242, P243, P261, P264+P265, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P333+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 691 reports by companies from 9 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. |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propanethiol, 2-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2-Propanethiol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanethiol, 2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 23-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21292-Propanethiol, 2-methyl-: HSNO Approval: HSR001102 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024) |
Anwendungen & Verwendung
Beschreibung
tert-Butylthiol, also known as 2-methyl propane-2-thiol, 2- methyl-2-propane thiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organo sulfur compound with the formula (CH3)3CSH. This thiol may have been used as a flavoring agent, as an odorant for natural gas (which is odorless), and also in a wide range of organic reactions.
Verwenden
2-Methyl-2-propanethiol was used in reaction of 2-methyl-2-propanethiol on Mo(110) using temperature programmed reaction, high resolution electron enegy loss and X-ray photoelectron spectroscopies. It was used in the synthesis of chain-transfer agents for reversible addition-fragmentation chain-transfer copolymerization of vinylidene chloride and methyl acrylate.
Herstellung & Synthese
synthetische
tert-Butyl thiol likely does not occur naturally, but at least one publication has listed it as a very minor component of cooked potatoes. The compound was first prepared in 1890 by Leonard Dobbin by the reaction of zinc sulfide and t-butyl chloride. The compound was later prepared in 1932 by the reaction of the Grignard reagent, t-BuMgCl, with sulfur to give the corresponding thiolate, followed by hydrolysis. This preparation is shown below: t-BuMgCl + S → t-BuSMgCl t-BuSMgCl + H2O → t-BuSH + Mg(OH)Cl It is currently prepared industrially by the reaction of isobutylene with hydrogen sulfide over a clay (silica alumina) catalyst.