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Merck
CN

108995

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24846848
EC Number:
219-121-7
Beilstein/REAXYS Number:
506259
MDL number:
MFCD00004873
Assay:
95%

Key Documents

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InChI key

MKIJJIMOAABWGF-UHFFFAOYSA-N

InChI

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

SMILES string

COC(=O)CS

assay

95%

reaction suitability

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

Quality Level

200

bp

42-43 °C/10 mmHg (lit.)

density

1.187 g/mL at 25 °C (lit.)

functional group

ester, thiol

Related Categories

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

signalword

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

3 - Flammable liquids

wgk

WGK 1

flash_point_f

132.8 °F - closed cup

flash_point_c

56 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6226
STBK4119
STBJ5810
BCBC0358
STBD9917V

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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
Samantha Seng et al.
Physical chemistry chemical physics : PCCP, 20(29), 19416-19423 (2018-06-28)
Understanding the formation and transformation of sulphur-rich particles is of prime importance since they contribute to the global atmospheric sulphur budget. In this work, we performed a series of experiments on a photoactive organosulphur compound namely, methyl thioglycolate, as a
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)
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
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