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318183

Sigma-Aldrich

Methyl sulfate sodium salt

Synonym(s):

Monomethyl ester sulfuric acid sodium salt, Sodium methyl sulfate

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About This Item

Linear Formula:
CH3OSO3Na
CAS Number:
Molecular Weight:
134.09
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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form

powder

impurities

<3% methanol
<5% water

mp

210 °C (lit.)

SMILES string

[Na+].COS([O-])(=O)=O

InChI

1S/CH4O4S.Na/c1-5-6(2,3)4;/h1H3,(H,2,3,4);/q;+1/p-1

InChI key

DZXBHDRHRFLQCJ-UHFFFAOYSA-M

Application

Methyl sulfate sodium salt can be used to synthesize:
  • Methylsulfate anion based 1,3,4-trialkyl-1,2,3-triazolium ionic liquids for use in Morita–Baylis–Hillman reaction.[1]
  • Anisole by reacting with phenol.[2]
  • Hydroxyanilino quinolines for use as RET kinase inhibitors.[3]

Reactant or reagent involved in:
  • Studying lamellar structure formation in hybrid nanomaterials created by miniemulsion
  • EPR studies of radical ions radiolytically generated from ionic liquids, used as a reference
  • Micellular studies specifically the rate-retarding effects on hydrolysis of substituted 1-benzoyl-1,2,4-triazoles and self-assembly / microstructure of mixed micelles

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The discovery of substituted 4-(3-hydroxyanilino)-quinolines as potent RET kinase inhibitors
Robinett R G, et al.
Bioorganic & Medicinal Chemistry Letters, 17(21), 5886-5893 (2007)
Synthesis of anisole from phenol and sodium methyl sulfate, a byproduct from synthesis of medicine intermediates
Guoping W, et al.
Petrochemical Technology, 45(11), 1337-1337 (2016)
Synthesis of new triazolium-based ionic liquids and their use in the Morita-Baylis-Hillman reaction
F Alioune, et al.
Tetrahedron Letters, 56(36), 5128-5131 (2015)
Richard Wolfenden et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(1), 83-86 (2006-12-22)
Alkyl sulfate monoesters are involved in cell signaling and structure. Alkyl sulfates are also present in many commercial detergents. Here, we show that monomethyl sulfate acts as an efficient alkylating agent in water, reacting spontaneously with oxygen nucleophiles >100-fold more
Bindhu V Karanam et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(10), 1061-1068 (2004-07-02)
MK-0767 [(+/-)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromethyl)phenyl]methyl]benzamide], a thiazolidinedione (TZD)-containing peroxisome proliferator-activated receptor agonist, is a rapidly interconverting racemate that possesses a chiral center at the five position of the TZD ring. M25 is a methyl sulfide metabolite generated from MK-0767 following CYP3A4-mediated TZD ring

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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