Sodium thiomethoxide Chemical Properties

Density 

1.12[at 20℃]

vapor pressure 

29hPa at 25℃

Flash point:

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

InChI

InChI=1S/CH4S.Na/c1-2;/h2H,1H3;/q;+1/p-1

InChIKey

RMBAVIFYHOYIFM-UHFFFAOYSA-M

SMILES

CS[Na]

LogP

-2.33 at 20℃

CAS DataBase Reference

5188-07-8(CAS DataBase Reference)

EPA Substance Registry System

Methanethiol, 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

F 

1-34-10-13

HazardClass 

4.3

PackingGroup 

II

HS Code 

29309090

MSDS

• Language:English Provider:Sodium thiomethoxide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Sodium thiomethoxide Usage And Synthesis

Description

Sodium 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 Properties

Very faint yellowish red clear liquid

Uses

Used to prepare a C-21 thioether of methyl 16-prednisolonecarboxylate by mesylate displacement.

Uses

Sodium 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 Profile

Sodium 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 Methods

Dissolve 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.]

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