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Merck

108995

Sigma-Aldrich

Methylthioglycolat

95%

Synonym(e):

Methyl-thioglykolat

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About This Item

Lineare Formel:
HSCH2CO2CH3
CAS-Nummer:
Molekulargewicht:
106.14
Beilstein:
506259
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

95%

Eignung der Reaktion

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

Brechungsindex

n20/D 1.466 (lit.)

bp

42-43 °C/10 mmHg (lit.)

Dichte

1.187 g/mL at 25 °C (lit.)

Funktionelle Gruppe

ester
thiol

SMILES String

COC(=O)CS

InChI

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

InChIKey

MKIJJIMOAABWGF-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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)

Piktogramme

FlameSkull and crossbones

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 1

Flammpunkt (°F)

132.8 °F - closed cup

Flammpunkt (°C)

56 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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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
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.
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)
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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