28274-57-9

Basic information

• Product Name: METHANESELENINIC ACID
• Synonyms: METHYLSELENINIC ACID;METHANESELENINIC ACID;methylselenic acid;NSC 243621;NSC 244776;Methaneseleninic acid 95%;Methaneseleninic acid(6CI,8CI,9CI)
• CAS NO: 28274-57-9
• Molecular Formula: CH₄O₂Se
• Molecular Weight: 127
• Mol File: 28274-57-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 128-132 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 12700mmHg at 25°C
• CAS DataBase Reference: METHANESELENINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: METHANESELENINIC ACID(28274-57-9)
• EPA Substance Registry System: METHANESELENINIC ACID(28274-57-9)

Safety Data

• Hazard Codes: T,N
• Statements: 23/25-33-34-50/53
• Safety Statements: 26-28-45-60-61-36/37/39-20/21
• RIDADR: UN 2928 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 28274-57-9(Hazardous Substances Data)

Usage

Uses

Methaneseleninic acid may be employed as a ligand in the preparation of lanthanide complexes. It may also be used in the synthesis of a 12-membered macrocycle [(p-MeO-C6H4)2Te(μ-O)-(μ-MeSeO2)(μ4-Cl)]2 by reacting with bis(p-methoxyphenyl)tellurium dichloride.

Definition

ChEBI: An organoselenium compound that is seleninic acid in which the hydrogen attached to selenium is replaced by a methyl group.

General Description

Methaneseleninic acid is an oxidizing agent useful in organic synthesis. It is formed as major product during the oxidations of γ-glutamyl-Se-methylselenocysteine and Se-methylselenocysteine.

InChI:InChI=1/CH4O2Se/c1-4(2)3/h1H3,(H,2,3)

Upstream product

• 593-79-3 dimethylselenide 
• 7101-31-7 dimethyl diselenide 
• 7697-37-2 nitric acid 

Downstream Products

• 593-79-3 dimethylselenide 
• 7101-31-7 dimethyl diselenide 
• 50-00-0 formaldehyd 
• 7446-08-4 selenium(IV) oxide 

Relevant articles and documents

Methylseleninic acid, a potent growth inhibitor of synchronized mouse mammary epithelial tumor cells in vitro

Selenium compounds have been shown to be effective chemopreventive agents in several animal models and in cultured cells in vitro. It has been proposed that compounds able to generate monomethyl Se have an increased potential to inhibit cell growth. To test this hypothesis, methylseleninic acid (MSeA) and other compounds that could generate methylselenol rapidly were compared with Se compounds that do not generate monomethyl Se, using a well-characterized synchronized TM6 mouse mammary epithelial tumor model in vitro. MSeA at a low micromolar concentration inhibited TM6 growth after 10- to 15-min treatment times. Cells resumed growth after 24 hr but remained sensitive to the fresh addition of monomethyl Se-generators. Dimethyl selenide (DMSe), a putative metabolite of methylselenol, was inactive. Cells treated with 5 μM MSeA were arrested in G1. The effects of 5 μM MSeA on gene expression were evaluated using the Atlas mouse cDNA expression array. A 10-min exposure with MSeA caused a 2- to 3-fold change in the expression of three genes: laminin receptor 1 (decreased), integrin beta (decreased), and Egr-1 (increased). The results provide experimental support for the hypothesis that monomethylated forms of Se are the critical effector molecules in Se-mediated growth inhibition in vitro.

Oxidation of Organic Diselenides with Hydrogen Peroxide to Alkane- and Areneseleninic Acids and Selenium-Containing Heterocycles

A convenient way is reported for the oxidation of organic diselenides 1,3 to organoseleninic acids 2,4 which were isolated and identified as pure compounds.Some ortho-substituted phenyl diselenides 3d-f underwent oxidative cyclization, and the selenium-co