Sodium methanethiolate

Base Information

• Chemical Name: Sodium methanethiolate
• CAS No.: 5188-07-8
• Deprecated CAS: 88905-59-3,1163726-60-0,1860886-54-9,2412885-58-4
• Molecular Formula: CH3NaS
• Molecular Weight: 71.0985
• Hs Code.: 29309090
• European Community (EC) Number: 225-969-9
• UNII: LB29JWW8H7
• DSSTox Substance ID: DTXSID7027592
• Nikkaji Number: J60.721E
• Wikipedia: Sodium_methanethiolate
• Wikidata: Q6553913
• Mol file: 5188-07-8.mol

Synonyms:Sodium thiomethoxide;Sodium methanethiolate;5188-07-8;Methanethiol sodium salt;Sodium thiomethylate;sodium methyl mercaptide;Methanethiol, sodium salt;sodiummethanethiolate;sodium;methanethiolate;LB29JWW8H7;CCRIS 9102;EINECS 225-969-9;Sodium Methanethiolate (95per cent);sodiumthiomethoxide;MFCD00174316;sodiumthiomethylate;methylsulfanylsodium;sodium methanthiolat;sodium metanethiolate;sodium methanthiolate;Methylsulfanyl sodium;sodium methylsulfanide;sodium thio-methoxide;(methylsulfanyl)sodium;sodium methan-ethiolate;sodium methane-thiolate;UNII-LB29JWW8H7;DTXSID7027592;RMBAVIFYHOYIFM-UHFFFAOYSA-M;Methanethiol, sodium salt (1:1);AKOS015840121;BP-12550;LS-188343;FT-0674621;M0096;E80403;EC 225-969-9;Q-201721;Q6553913

Chemical Property of Sodium methanethiolate

Chemical Property:

• Appearance/Colour: very faint yellowish red clear liquid
• Vapor Pressure: 29hPa at 25℃
• Melting Point: -123oC
• Flash Point: 27°C
• PSA: 0.00000
• Density: 1.12[at 20℃]
• LogP: 0.16310
• Storage Temp.: Flammables area
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 69.98531555
• Heavy Atom Count: 3
• Complexity: 4.8

Purity/Quality:

99%, ^*data from raw suppliers

Sodium Methanethiolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F
• Hazard Codes: C,F
• Statements: 31-34-20/21/22-11-35-25-10
• Safety Statements: 26-36/37/39-45-16

MSDS Files:

Useful:

• Chemical Classes: Metals -> Organic Compounds, Metal Salts
• Canonical SMILES: C[S-].[Na+]
• 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. Used to prepare a C-21 thioether of methyl 16-prednisolonecarboxylate by mesylate displacement.

Technology Process of Sodium methanethiolate

There total 15 articles about Sodium methanethiolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.9%

methyl O-methyldithiocarbonate (19708-81-7) + ethylamine (75-04-7,85404-22-4) → N-ethyl O-methyl thiocarbamate (65351-53-3) + sodium thiomethoxide (5188-07-8)

Guidance literature:

at 45 - 55 ℃; under 400 Torr;

Reference yield: 98.5%

S-methyl N-ethylthiocarbamate (39076-43-2) → N-Ethylurea (625-52-5) + sodium thiomethoxide (5188-07-8)

Guidance literature:

With ammonia; In water; at 60 ℃; for 4h;

Reference yield: 51.0%

Dimethyldisulphide (624-92-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → sodium 1,2,3,4,5-pentakis(methylmercapto)cyclopentadienide + sodium thiomethoxide (5188-07-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 72h; Ambient temperature;

DOI:10.1021/ja00409a044

upstream raw materials:

methylthiol

sodium ethanolate

Dimethyldisulphide

cyclopenta-1,3-diene

Downstream raw materials:

4-(methylthio)butanoic acid

1-(methylthio)propan-2-ol

4-thiomethyl-6-methylpyrimidine

(-)-(7S)-allocolchicine

Refernces

Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement

10.1021/ol051411t

The study presents the total synthesis of serofendic acids A and B, which are neuroprotective agents with complex structures featuring nine stereocenters and an atisane framework. The key strategic element of the synthesis involves a novel tin-free homoallyl-homoallyl radical rearrangement for constructing the bicyclo[2.2.2]octane ring system. Various chemicals were used in the study, including sodium thiomethoxide for the Michael reaction, Barton-McCombie deoxygenation protocol for promoting the rearrangement, and Taber's technique for radical generation under tin-free conditions. Other chemicals mentioned include NaBH4, (imid)2CdS, Bu3SnH, AIBN, toluene, PPh3, DEAD, NBSH, THF, TsNHNH2, NaBH3CN, ZnCl2, and benzeneseleninic anhydride, among others. These chemicals served various purposes in the synthesis process, such as reducing agents, catalysts, and reagents for specific reactions, ultimately leading to the successful synthesis of serofendic acids A and B.

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