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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

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4119
STBJ5810
BCBC0358
STBD9917V
STBD6331V

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Sigma-Aldrich

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W A LaMarr et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(1), 102-107 (1998-02-21)
DNA superhelical tension, an important feature of genomic organization, is known to affect the interactions of intercalating molecules with DNA. However, the effect of torsional tension on nonintercalative DNA-binding chemicals has received less attention. We demonstrate here that the enediyne
M K Vadnere et al.
Journal of medicinal chemistry, 29(9), 1714-1720 (1986-09-01)
The reaction of methyl mercaptoacetate (5) with phenyl-p-benzoquinone (6) or 5-p-benzoquinonyl-3',5'-di-O-acetyl-2'-deoxyuridine (10) resulted in the formation of the three possible adducts to the quinone rings of 6 and 10; an additional product in the reaction with 10 was the unsubstituted
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
O D Hensens et al.
The Journal of antibiotics, 42(5), 761-768 (1989-05-01)
The structures of mercaptan and sodium borohydride reaction products of neocarzinostatin chromophore A (NCS Chrom A) are compared. Implications on the mechanism of activation of NCS are discussed.
D J Creighton et al.
Biochemistry, 27(19), 7376-7384 (1988-09-20)
A quantitative kinetic model for the glutathione-dependent conversion of methylglyoxal to D-lactate in mammalian erythrocytes has been formulated, on the basis of the measured or calculated rate and equilibrium constants associated with (a) the hydration of methylglyoxal, (b) the specific
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