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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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

108995-500G:
108995-VAR:
108995-5G:
108995-100G:
108995-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4119
STBJ5810
BCBC0358
STBD9917V
STBD6331V

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Sigma-Aldrich

556912

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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
M A Napier et al.
Molecular pharmacology, 23(2), 500-510 (1983-03-01)
The site responsible for the mercaptan (or borohydride)-stimulated DNA scission activity of neocarzinostatin chromophore (NCS-Chrom) is located in the central C12-subunit of the molecule. This has been determined by studies of the characteristic spectral properties of the chromophore and its
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)
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