30383-01-8

Basic information

• Product Name: LithiuM thioethoxide
• Synonyms: LithiuM thioethoxide;Lithium ethanethiolate;Lithium ethyl sulfide;Lithium ethyl thiolate;Lithium ethylmercaptide
• CAS NO: 30383-01-8
• Molecular Formula: C₂H₅LiS
• Molecular Weight: 84.0665
• Mol File: 30383-01-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 316-333°C
• Appearance: /
• CAS DataBase Reference: LithiuM thioethoxide(CAS DataBase Reference)
• NIST Chemistry Reference: LithiuM thioethoxide(30383-01-8)
• EPA Substance Registry System: LithiuM thioethoxide(30383-01-8)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14-34
• Safety Statements: 16-26-36/37/39-43-45
• RIDADR: UN 3206 8(4.2) / PGII
• WGK Germany: 3
• Hazardous Substances Data: 30383-01-8(Hazardous Substances Data)

Usage

Description

Lithium thioethoxide, also known as Lithium ethanethiolate, is an organolithium compound with the chemical formula LiC2H5S. It is a colorless to pale yellow liquid that is highly reactive and sensitive to air and moisture. Its structure consists of a lithium atom bonded to a thiolate group (S-) and an ethyl group (C2H5). Due to its reactivity, it is commonly used in various chemical reactions and processes.

Uses

1. Used in Organic Synthesis:
Lithium thioethoxide is used as a reagent for the preparation of various organic compounds. Its strong nucleophilic properties allow it to participate in a wide range of reactions, such as nucleophilic substitution, addition, and elimination reactions.
2. Used in Microwave-Assisted Cleavage of Aryl Methyl Ethers:
Lithium thioethoxide is employed as a cleaving agent in the microwave-assisted cleavage of aryl methyl ethers. The reaction involves the nucleophilic attack of the lithium thioethoxide on the aryl methyl ether, leading to the cleavage of the ether bond and the formation of the corresponding aryl thiolate and methanol.
3. Used in the Synthesis of Triply Thiolate-Bridged Diiron Complexes:
Lithium thioethoxide is used as a building block in the synthesis of triply thiolate-bridged diiron complexes. These complexes are important in various fields, such as catalysis and bioinorganic chemistry, due to their unique electronic and structural properties.
4. Used in the Synthesis of (+)-Batzelladine A and (-)-Batzelladine D:
Lithium thioethoxide is utilized as a key intermediate in the synthesis of (+)-batzelladine A and (-)-batzelladine D, which are complex natural products with potential biological activities. The reactivity of lithium thioethoxide allows for the formation of the required thiolate bridges and the construction of the complex molecular framework.

Upstream product

• 75-08-1 ethanethiol 

Downstream Products

• 131393-75-4 (E)-2-ethylthio-1-nitroethylene 
• 132839-84-0 (E)-<2-(Ethylthio)ethenylphenyl>sulfon 
• 351209-70-6 2-trimethylsilanyl-ethanesulfonic acid {4-benzyloxy-6-benzyloxymethyl-5-[4,5-bis-benzyloxy-6-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-ethylsulfanyl-tetrahydro-pyran-3-yl}-amide 
• 521274-41-9 S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate 
• 902782-15-4 ethyl (2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-(2-(tert-butyldiphenylsiloxy)ethyl)-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynethioate 
• 169128-58-9 C₅H₅Fe(CO)[Sn(C₆H₅)3]C(C₆H₅)SC₂H₅ 
• 20890-79-3 (Z)-β-(ethylthio)styrene 
• 78840-01-4 1-phenyl-3-ethylthio-1-butenyl diphenyl phosphate 
• 63385-22-8 p-methyldithiobenzoic acid ethyl ester 
• 97270-43-4 lithium diphenyldithiophosphinate 
• 627-97-4 2-methyl-2-heptene 
• 27482-14-0 1-(ethylthio)-2-methylpropene 
• 138630-73-6 <3,4-dihydro-6-methoxy-2-phenyl-1-naphthalenyl>(4-hydroxyphenyl)methanone 
• 75-08-1 ethanethiol 

Relevant articles and documents

Erogorgiaene congeners and methods and intermediates useful in the preparation of same

Disclosed are compounds having the formula: wherein R21 is an alkyl, aryl, alkoxy, hydroxy, or amino group or a halogen atom; wherein R2 is hydrogen or an alkyl, aryl, alkoxy, or amino group; wherein R23 and R24 are independently selected from hydrogen, an alkyl, aryl, alkoxy, hydroxy, or amino group, and a halogen atom or wherein R23 and R24, taken together with the carbon atom to which they are bound, form a ring; wherein R25 is hydrogen, an alkyl, aryl, alkoxy, hydroxy, or O-silyl group or a halogen atom; wherein Z, taken together with the carbons to which it is bonded, forms a 5-12 membered ring; and wherein Y is an electron withdrawing group. These compounds can be used to prepare erogorgiaene congeners, such as erogorgiaene, pseudopterosin A, helioporin E, pseudopteroxazole, colombiasin A, elisapoterosin B, elisabethadione, p-benzoquinone natural products, ileabethin, sinulobtain B, sinulobtain C, and sinulobtain D.

Microwave-assisted cleavage of aryl methyl ethers with lithium thioethoxide (LiSEt)

Lithium thioethoxide (LiSEt), a white solid easily prepared from EtSH and n-BuLi in hexane, was identified as a highly efficient reagent for the cleavage (O-demethylation) of aryl methyl ethers, i.e. methyl-protected phenols. Of particular synthetic value are applications in the double deprotection of 1,2-dimethoxyarenes (to give catechols) and in the selective monodeprotection of di- and trimethoxyarenes. The thermal reactions, which are usually performed in DMF as a solvent, can be greatly accelerated through microwave irradiation. In this case, the monodemethylated products are usually formed in high (80-99%) yield within only 15 minutes.

Benzo [B] indeno [2,1-D] thiophene compounds, intermediates, processes, compositions and methods

The invention provides benzo[b]indenothiophene compounds of formula I I wherein, R1, R2, R3, R4, R5, and R6, are as defined in the specification, intermediates, formulations, and methods of inhibiting bone loss or bone resorption, particularly ost