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Sodium thiomethoxide

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CAS:5188-07-8
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  • CAS:5188-07-8
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Sodium thiomethoxide Basic information
Product Name:Sodium thiomethoxide
Synonyms:SODIUM METHYL SULFIDE;SODIUM THIOMETHOXIDE;Sodium thiomethoxyde;1-Methanethiolsodiumsalt;Sodium methanethiol;Sodium thiomethoxide, pure, 95%;Sodium thiomethoxide, Methanethiol sodium salt;METHYL MERCAPTAN SODIUM SALT: 15% IN WATER
CAS:5188-07-8
MF:CH3NaS
MW:70.09
EINECS:225-969-9
Product Categories:Classes of Metal Compounds;Na (Sodium) Compounds (excluding simple sodium salts);Typical Metal Compounds;API;Aliphatics;Sulfur & Selenium Compounds;YP00036
Mol File:5188-07-8.mol
Sodium thiomethoxide Structure
Sodium thiomethoxide Chemical Properties
density 1.12[at 20℃]
vapor pressure 29hPa at 25℃
Fp 27°C
storage temp. Flammables area
solubility soluble in Water
form Powder
color White to off-white
Water Solubility soluble
Merck 14,5956
BRN 3592983
InChIInChI=1S/CH4S.Na/c1-2;/h2H,1H3;/q;+1/p-1
InChIKeyRMBAVIFYHOYIFM-UHFFFAOYSA-M
SMILESCS[Na]
LogP-2.33 at 20℃
CAS DataBase Reference5188-07-8(CAS DataBase Reference)
EPA Substance Registry SystemMethanethiol, sodium salt (5188-07-8)
Safety Information
Hazard Codes C,F
Risk Statements 31-34-20/21/22-11-35-25-10
Safety Statements 26-36/37/39-45-16
RIDADR UN 3263 8/PG 3
WGK Germany 3
1-34-10-13
HazardClass 4.3
PackingGroup II
HS Code 29309090
MSDS Information
ProviderLanguage
Sodium thiomethoxide English
SigmaAldrich English
ACROS English
Sodium thiomethoxide Usage And Synthesis
DescriptionSodium methanethiolate or sodium thiomethoxide (CH3SNa, MeSNa) is the sodium conjugate base of methanethiol. This compound is commercially available as a white solid. Sodium Methanethiolate is used as a nucleophile in organic synthesis. This compound is also being used as a reagent to synthesize thiol-based suberoylanilide hydroxamic acid (SAHA) analogues, compounds that act as potent histone deacetylase inhibitors. It reacts with trifluoroacetic acid and water to produce the active form of sodium trifluoroacetate. The reaction mechanism is likely due to the formation of a bicyclic heterocycle that has been shown to be effective against a number of bacteria.
Chemical PropertiesVery faint yellowish red clear liquid
UsesUsed to prepare a C-21 thioether of methyl 16-prednisolonecarboxylate by mesylate displacement.
UsesSodium thiomethoxide is a strong nucleophile used for the synthesis of methyl aryl sulfides from halo-arenes. Alkanethiolates are efficient reagents for SN2 dealkylation of esters and aryl ethers.
Reactivity ProfileSodium thiomethoxide is a powerful nucleophile that can be used to prepare methylthioether and other organic compounds like ethyl bromide. Its hydrolysis in moist air produces methanethiol, which has a low odor threshold and a noxious fecal smell.
Purification MethodsDissolve the salt (10g) in EtOH (10mL) and add Et2O (100mL). Cool and collect the precipitate, wash it with Et2O and dry it in a vacuum. It is a white powder which is very soluble in EtOH and H2O. [Billmann & Jensen Bull Soc Chim Fr 3 2318 1936, Beilstein 1 III 1212.]
Tag:Sodium thiomethoxide(5188-07-8) Related Product Information
SODIUM TETRATHIONATE DIHYDRATE Sodium tetraborate decahydrate Sodium triacetoxyborohydride Sodium sulfide Sodium thiocyanate Sodium sulfate Sodium sulfite Sodium thiosulfate Sulfamic acid monosodium salt Sodium trimetaphosphate Sodium xylenesulfonate Sodium tetrafluoroborate Sodium tungstate Sodium stearate Sodium tert-pentoxide Sodium tripolyphosphate Sodium taurocholate Sodium thiosulfate pentahydrate Methyl Mercaptan Sodium Salt Sodium Methyl Mercaptide