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P16621

Sigma-Aldrich

Phenylacetic acid

99%

Synonym(s):

α-Toluic acid, α-Tolylic acid, Benzeneacetic acid, PAA

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About This Item

Linear Formula:
C6H5CH2CO2H
CAS Number:
103-82-2
Molecular Weight:
136.15
Beilstein:
1099647
EC Number:
203-148-6
MDL number:
MFCD00004313
UNSPSC Code:
12352100
PubChem Substance ID:
24898234
NACRES:
NA.22

vapor density

~4 (vs air)

Quality Level

100

vapor pressure

1 mmHg ( 97 °C)

Assay

99%

form

crystals

bp

265 °C (lit.)

mp

76-78 °C (lit.)

density

1.081 g/mL at 25 °C (lit.)

SMILES string

OC(=O)Cc1ccccc1

InChI

1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

InChI key

WLJVXDMOQOGPHL-UHFFFAOYSA-N

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Application

  • Phenylacetic acid can be used to synthesize a variety of phenyl substituted compounds by Pd (II)-catalyzed C-H activation/aryl-aryl coupling reaction.
  • It can be employed in the preparation of Mn16 single-molecule magnets by reductive aggregation route.
  • It can be used as a precursor to synthesize chromones, isoflavones, and homoisoflavones.
  • It can also be used as a key precursor in the synthesis of emethallicin E and (−)-incarviatone A.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

269.6 °F - closed cup

Flash Point(C)

132 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ8433
STBJ2819
STBH5365
STBH3335
STBF1775V

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Versatile Pd (II)-Catalyzed C? H Activation/Aryl? Aryl Coupling of Benzoic and Phenyl Acetic Acids.
Wang D H, et al.
Journal of the American Chemical Society, 130(52), 17676-17677 (2008)
Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio) diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8, 8?-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents.
Nicolaou K C, et al.
Journal of the American Chemical Society, 134(41), 17320-17332 (2012)
Enantioselective Total Synthesis of (?)-Incarviatone A.
Hong B, et al.
Journal of the American Chemical Society, 137(37), 11946-11949 (2015)
A mild and efficient protocol to synthesize chromones, isoflavones, and homoisoflavones using the complex 2, 4, 6-trichloro-1, 3, 5-triazine/dimethylformamide.
Basha G M, et al.
Canadian Journal of Chemistry, 91(8), 763-768 (2013)
A Family of Mn16 Single-Molecule Magnets from a Reductive Aggregation Route.
King P, et al.
Inorganic Chemistry, 43(23), 7315-7323 (2004)
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