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P27127

Sigma-Aldrich

Phenylmercuric acetate

97%

Synonym(s):

Phenylmercury acetate, Mercury phenyl acetate

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About This Item

Linear Formula:
C6H5HgOCOCH3
CAS Number:
62-38-4
Molecular Weight:
336.74
Beilstein:
3662930
EC Number:
200-532-5
MDL number:
MFCD00008691
UNSPSC Code:
12352103
PubChem Substance ID:
24898353
NACRES:
NA.22

Assay

97%

form

powder

mp

148-151 °C (lit.)

SMILES string

CC(=O)O[Hg]c1ccccc1

InChI

1S/C6H5.C2H4O2.Hg/c1-2-4-6-5-3-1;1-2(3)4;/h1-5H;1H3,(H,3,4);/q;;+1/p-1

InChI key

XEBWQGVWTUSTLN-UHFFFAOYSA-M

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Application

Phenylmercuric acetate (PMA) can react with a palladium salt such as palladium acetate to form an arylpalladium salt in situ, which then reacts with primary or secondary allylic alcohols to produce 3-aryl aldehydes. It can also be used in the multi-step synthesis of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl thiol via Floyd′s pathway.

Signal Word

Danger

Hazard Statements

H300,H314,H372,H410

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B - STOT RE 1

Target Organs

Kidney,Central nervous system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The arylation of allylic alcohols with organopalladium compounds. A new synthesis of 3-aryl aldehydes and ketones.
Heck R F, et al.
Journal of the American Chemical Society, 90(20), 5526-5531 (1968)
Synthesis of aromatic and indole alpha-glucosinolates.
Vo Quan V, et al.
Carbohydrate Research, 455, 45-53 (2018)
Satu Lyyra et al.
Plant biotechnology journal, 5(2), 254-262 (2007-02-21)
Eastern cottonwood (Populus deltoides Bartr. ex Marsh.) trees were engineered to express merA (mercuric ion reductase) and merB (organomercury lyase) transgenes in order to be used for the phytoremediation of mercury-contaminated soils. Earlier studies with Arabidopsis thaliana and Nicotiana tabacum
S K Ghosh et al.
Journal of applied microbiology, 102(2), 375-383 (2007-01-24)
Mercury compounds are highly toxic to all types of living cells. Isolated yeast strains of Rhodotorula rubra showed high and low resistance pattern towards mercury and organomercurial compounds. To investigate the basis of differential sensitivity of these two types of
Harry J Beaulieu et al.
Journal of occupational and environmental hygiene, 5(6), 360-366 (2008-03-28)
Phenyl mercuric acetate (PMA) historically has been used as a catalyst in polyurethane systems. In the 1950s-1970s, PMA was used as a catalyst in the 3M Tartan brand polyurethane flexible floors that were installed commonly in school gymnasiums. Mercury vapor
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