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Safety Information

108995

Sigma-Aldrich

Methyl thioglycolate

95%

Synonym(s):

Methyl mercaptoacetate

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About This Item

Linear Formula:
HSCH2CO2CH3
CAS Number:
2365-48-2
Molecular Weight:
106.14
Beilstein:
506259
EC Number:
219-121-7
MDL number:
MFCD00004873
UNSPSC Code:
12352100
PubChem Substance ID:
24846848
NACRES:
NA.22

Quality Level

200

Assay

95%

reaction suitability

reagent type: ligand
reaction type: [1,2]-Wittig Rearrangement

refractive index

n20/D 1.466 (lit.)

bp

42-43 °C/10 mmHg (lit.)

density

1.187 g/mL at 25 °C (lit.)

functional group

ester
thiol

SMILES string

COC(=O)CS

InChI

1S/C3H6O2S/c1-5-3(4)2-6/h6H,2H2,1H3

InChI key

MKIJJIMOAABWGF-UHFFFAOYSA-N

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General description

Methyl thioglycolate reacts with nonprotein component of the antitumor antibiotic neocarzinostatin to form 1:1 adduct. It reacts with isothiocyanate to form Rhodanine.

Application

Methyl thioglycolate was used in the preparation of:
  • 3-carbomethoxy-4- oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene
  • methyl thioglycolate and aminoethanethiol conjugated gold nanorods.
Thiol Organocatalyst used in conjunction with visible light photocatalysis to affect the direct arylation of benzylic ether C-H bonds

A General Strategy for Organocatalytic Activation of C–H Bonds via Photoredox Catalysis: Direct Arylation of Benzylic Ethers

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

132.8 °F - closed cup

Flash Point(C)

56 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4119
STBJ5810
BCBC0358
STBD9917V
STBD6331V

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T Kusakabe et al.
Biochemistry, 34(31), 9944-9950 (1995-08-08)
A double-stranded DNA cleavage mechanism by a novel enediyne type antitumor antibiotic, dynemicin A, has been investigated through sequence-dependent strand breakage of a series of duplexes containing a single nucleotide gap. We found that (1) dynemicin A breaks specifically at
An improved procedure for the preparation of 3-carbometfaoxy-4-oxotetrahydrothiopyran, 2-and 4-carbomethoxy-3-oxotetrahydrothiophene.
Liu HJ and Ngooi TK.
Canadian Journal of Chemistry, 60(4), 437-439 (1982)
Stereochemical assignment of neocarzinostatin chromophore. Structures of neocarzinostatin chromophore-methyl thioglycolate adducts.
Myers AG, et al.
Journal of the American Chemical Society, 110(21), 7212-7214 (1988)
Z Mester et al.
Rapid communications in mass spectrometry : RCM, 13(5), 350-353 (1999-04-21)
A gas chromatography/mass spectrometry (GC/MS) method has been developed to determine two methylated arsenic species in human urine samples. The yield of derivatization for dimethylarsinic acid (DMA) and monomethylarsonic acid (MMA) using thioglycol methylate (TGM) was measured. The detection limit
Y Sugiura et al.
Biochemistry, 30(12), 2989-2992 (1991-03-26)
The reaction products of methyl thioglycolate with dynemicin A, dynemicin H and dynemicin S, were isolated by HPLC purification and identified spectroscopically. The major product, dynemicin H (C30H23NO9), was determined to be a C-8 hydrogen analogue of dynemicins L and
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