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108995

Sigma-Aldrich

Methyl thioglycolate

95%

Synonyme(s) :

Methyl mercaptoacetate

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About This Item

Formule linéaire :
HSCH2CO2CH3
Numéro CAS:
2365-48-2
Poids moléculaire :
106.14
Numéro Beilstein :
506259
Numéro CE :
219-121-7
Numéro MDL:
MFCD00004873
Code UNSPSC :
12352100
ID de substance PubChem :
24846848
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

95%

Pertinence de la réaction

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

Indice de réfraction

n20/D 1.466 (lit.)

Point d'ébullition

42-43 °C/10 mmHg (lit.)

Densité

1.187 g/mL at 25 °C (lit.)

Chaîne SMILES 

COC(=O)CS

InChI

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

Clé InChI

MKIJJIMOAABWGF-UHFFFAOYSA-N

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Description générale

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)

Pictogrammes

FlameSkull and crossbones
GHS02,GHS06

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

132.8 °F - closed cup

Point d'éclair (°C)

56 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Isooctyl 3-mercaptopropionate ≥99%

Sigma-Aldrich

556912

Isooctyl 3-mercaptopropionate

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
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
Yuling Xiao et al.
Theranostics, 2(8), 757-768 (2012-08-24)
A multifunctional gold nanorod (GNR)-based nanoplatform for targeted anticancer drug delivery and positron emission tomography (PET) imaging of tumors was developed and characterized. An anti-cancer drug (i.e., doxorubicin (DOX)) was covalently conjugated onto PEGylated (PEG: polyethylene glycol) GNR nanocarriers via
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