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Sodium thiomethoxide

Sodium thiomethoxide structure

CAS No:
5188-07-8
Formula:
CH3NaS
Chemical Name:
Sodium thiomethoxide
Synonyms:
Sodium thiomethoxide solution;METHANETHIOL SODIUM SALT;SODIUM METHYL SULFIDE;SODIUM THIOMETHOXIDE;Sodium thiomethoxyde;SODIUM THIOMETHOXIDE, 21 VOL. % SOLN IN WATER, A PRODUCT OF ELF ATOCHEM (SMM);1-Methanethiolsodiumsalt;Sodium thiomethoxide, pure, 95%
Categories:
Organic Chemistry > Organometalate

Description

Very faint yellowish red clear liquid

Liquid

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.

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 Basic Attributes

Molecular Weight：

70.09

Exact Mass：

69.985

BRN：

3592983

EC Number：

225-969-9

UNII：

LB29JWW8H7

TSCA：

TSCA listed

DSSTox ID：

DTXSID7027592

Color/Form：

White to off-white

HScode：

29309090

Characteristics

PSA：

XLogP3：

0.16310

Appearance：

White to off-white Powder

Density：

1.12[at 20℃]

Melting Point：

-123ºC

Flash Point：

27°C

Water Solubility：

soluble

Storage Conditions：

Flammables area

Vapor Pressure：

29hPa at 25℃

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.

Critical Temperature & Pressure：

Air and moisture sensitive. Store under inert gas. Sensitive to carbon dioxide Exposure to moisture.

Safety Information

Packing level：

Hazard category：

4.3

Transport codes：

UN 3263 8/PG 3

wgk germany：

hazard class code：

C,F

safety instructions：

26-36/37/39-45-16

Marks：

C,F

Precautionary statement(s)：

P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, P501

Hazard Statements：

31-34-20/21/22-11-35-25-10

RIDADR：

UN 3263 8/PG 3

GHS Classification：

|Danger|H226 (18.46%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 65 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Sodium thiomethoxide Use and Manufacturing

Uses

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.

Intermediates

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

Manufacturing Info：

Pesticide, fertilizer, and other agricultural chemical manufacturing|Methanethiol, sodium salt (1:1): ACTIVE

Computed Properties

Molecular Weight:70.09
Hydrogen Bond Acceptor Count:1
Exact Mass:69.98531555
Monoisotopic Mass:69.98531555
Topological Polar Surface Area:1
Heavy Atom Count:3
Complexity:4.8
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Material

Dimethylacetamide

Sodium hydroxide

Dimethyl disulfide

Ethanol

Ethylamine

Downstream Products

Acetaldehyde, 2-(methylthio)-, oxime

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CAS No.: 5188-07-8

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