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561762

Sigma-Aldrich

4-Thioanisolemagnesium bromide solution

0.5 M in THF

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About This Item

Linear Formula:
H3CSC6H4MgBr
CAS Number:
18620-04-7
Molecular Weight:
227.40
MDL number:
MFCD00672010
UNSPSC Code:
12352103
PubChem Substance ID:
24879970
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C

density

0.965 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CSc1ccc([Mg]Br)cc1

InChI

1S/C7H7S.BrH.Mg/c1-8-7-5-3-2-4-6-7;;/h3-6H,1H3;1H;/q;;+1/p-1

InChI key

SSVQCUSLJVVRCA-UHFFFAOYSA-M

Application

4-Thioanisolemagnesium bromide can be used to prepare:
  • 3,3-Ethylenedioxy-5a-hydroxy-11b-[4-(thiomethoxy)phenyl]-estr-9-en-17-one, a key intermediate for the synthesis of mifepristone analogs.[1]
  • (1S)-1,4-Anhydro-2,3,5,6-tetra-O-benzyl-1-C-[4-chloro-3-(4-methylthiobenzyl)-phenyl]-D-glucitol, a key intermediate for the synthesis of aryl D-glucofuranosides as potent hSGLT2 and hSGLT1 inhibitors.[2]

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F

Flash Point(C)

-17 °C

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.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

561762-VAR:
561762-50ML:4548173170121
561762-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR2604
SHBF7887V
SHBF0511V
SHBC8103V
37396EM

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Weiqin Jiang et al.
Steroids, 71(11-12), 949-954 (2006-08-29)
A novel series of steroidal compounds were designed and synthesized with various phosphorus-containing groups on the 17beta-side chain as progesterone receptor antagonists. The structure-activity relationships of these compounds are discussed. Selected compounds were tested in an rat progesterone-sensitive assay. Some
Tzung-Sheng Lin et al.
Bioorganic & medicinal chemistry, 21(21), 6282-6291 (2013-09-28)
Novel C-aryl-d-glucofuranosides were synthesized and evaluated for their capacity to inhibit human sodium-dependent glucose co-transporter 2 (hSGLT2) and hSGLT1. Compound 21q demonstrated the best in vitro inhibitory activity against SGLT2 in this series (EC50=0.62μM).

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