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108995

Sigma-Aldrich

Methyl thioglycolate

95%

Sinónimos:

Methyl mercaptoacetate

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About This Item

Fórmula lineal:
HSCH2CO2CH3
Número de CAS:
2365-48-2
Peso molecular:
106.14
Beilstein:
506259
Número CE:
219-121-7
Número MDL:
MFCD00004873
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24846848
NACRES:
NA.22
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Nivel de calidad

200

Ensayo

95%

idoneidad de la reacción

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

índice de refracción

n20/D 1.466 (lit.)

bp

42-43 °C/10 mmHg (lit.)

densidad

1.187 g/mL at 25 °C (lit.)

grupo funcional

ester
thiol

cadena SMILES

COC(=O)CS

InChI

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

Clave InChI

MKIJJIMOAABWGF-UHFFFAOYSA-N

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Descripción general

Methyl thioglycolate reacts with nonprotein component of the antitumor antibiotic neocarzinostatin to form 1:1 adduct[1]. It reacts with isothiocyanate to form Rhodanine[2].

Aplicación

Methyl thioglycolate was used in the preparation of:
  • 3-carbomethoxy-4- oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene[3]
  • methyl thioglycolate and aminoethanethiol conjugated gold nanorods[4].
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)

Pictogramas

FlameSkull and crossbones
GHS02,GHS06

Palabra de señalización

Danger

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

132.8 °F - closed cup

Punto de inflamabilidad (°C)

56 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
STBK4119
STBJ5810
BCBC0358
STBD9917V
STBD6331V

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Isooctyl 3-mercaptopropionate ≥99%

Sigma-Aldrich

556912

Isooctyl 3-mercaptopropionate

Z Mester et al.
Rapid communications in mass spectrometry : RCM, 13(5), 350-353 (1999-04-21)
A gas chromatography/mass spectrometry (GC/MS) method has been developed to determine two methylated arsenic species in human urine samples. The yield of derivatization for dimethylarsinic acid (DMA) and monomethylarsonic acid (MMA) using thioglycol methylate (TGM) was measured. The detection limit
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)
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.
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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