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Merck
CN

149845

Thallium(I) ethoxide

Synonym(s):

Ethanol thallium salt, Ethyl alcohol thallium(I) salt, Thallium monoethoxide, Thallous ethoxide

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About This Item

Linear Formula:
TlOC2H5
CAS Number:
20398-06-5
Molecular Weight:
249.44
NACRES:
NA.22
PubChem Substance ID:
24848978
UNSPSC Code:
12352300
EC Number:
243-786-2
MDL number:
MFCD00009072

Key Documents

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form

liquid

InChI key

DZFYOYRNBGNPJW-UHFFFAOYSA-N

InChI

1S/C2H5O.Tl/c1-2-3;/h2H2,1H3;/q-1;+1

SMILES string

CCO[Tl]

reaction suitability

core: thallium
reagent type: catalyst

refractive index

n20/D 1.676 (lit.)

density

3.522 g/mL at 25 °C (lit.)

storage temp.

2-8°C

Quality Level

100

Application

With HCl, reduces a variety of functional groups; stereoselective allylation of carbonyl compounds; in situ generation of tin enolates for directed aldol reactions.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Chronic 2 - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBH9291
STBH2339
STBG6179
STBF0618V
STBF0382V

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S A Frank et al.
Organic letters, 2(17), 2691-2694 (2000-09-16)
[reaction: see text]Thallium(I) ethoxide promotes Suzuki cross couplings for a range of vinyl- and arylboronic acids with vinyl and aryl halide partners in good to excellent yields. This reagent offers distinct advantages over thallium(I) hydroxide in terms of commercial availability
Andrews, P. C.; Peatt, A. C.; Raston, C. L.
Tetrahedron Letters, 43, 7541-7541 (2002)
Yann Sarazin et al.
Journal of the American Chemical Society, 129(4), 881-894 (2007-01-25)
The reaction of thallium ethoxide with [H(OEt2)2][H2N{B(C6F5)3}2] in diethyl ether afforded [Tl(OEt2)3][H2N{B(C6F5)3}2] (2a), [Tl(OEt2)4][H2N{B(C6F5)3}2] (2b), or [Tl(OEt2)2][H2N{B(C6F5)3}2].CH2Cl2 (2c), depending on the reaction conditions. The dication in the hydrolysis product [Tl4(mu3-OH)2][H2N{B(C6F5)3}2]2.4CH2Cl2 consists of two bridging and two terminal Tl+ ions bound
Chan, T. H.; Li, C. J.; Wei, Z. Y.,
Journal of the Chemical Society. Chemical Communications, 505-505 (1990)
Michel J Kohl et al.
Steroids, 67(1), 71-75 (2001-12-01)
Conjugation of haptens through ether linkages avoids leakage problems in immunoassays, but this procedure is not easily applied to most steroids that bear low reacting hydroxyls. A new technique allowing the ether coupling of biologically active steroids with conjugating arms
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