108995

Sigma-Aldrich

Methyl thioglycolate

95%

Synonym(s):
Methyl mercaptoacetate
Linear Formula:
HSCH2CO2CH3
CAS Number:
Molecular Weight:
106.14
Beilstein/REAXYS Number:
506259
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

reaction suitability

reaction type: Photocatalysis
reagent type: catalyst
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.)

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

Packaging

5, 100, 500 g in glass bottle

pictograms

FlameSkull and crossbones

signalword

Danger

hazcat

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 Germany

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

Certificate of Analysis

Certificate of Origin

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)
Sumati Murli et al.
Applied and environmental microbiology, 71(8), 4503-4509 (2005-08-09)
Chemobiosynthesis (J. R. Jacobsen, C. R. Hutchinson, D. E. Cane, and C. Khosla, Science 277:367-369, 1997) is an important route for the production of polyketide analogues and has been used extensively for the production of analogues of 6-deoxyerythronolide B (6-dEB)....
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...
Luca Bertini et al.
Dalton transactions (Cambridge, England : 2003), 40(30), 7704-7712 (2011-06-01)
Amavadin is an unusual octa-coordinated V(IV) complex isolated from Amanita muscaria mushrooms. The outer-sphere catalytic properties of such a complex toward several oxidation reactions are well known. Nevertheless, a remarkable example exists, in which the V(V) (d(0)) oxidized form of...

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