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Phenylacetic acid

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Identification
Molecular formula
C8H8O2
CAS number
103-82-2
IUPAC name
2-phenylacetic acid
State
State

At room temperature, phenylacetic acid is found in a solid state, typically forming crystalline structures or powder.

Melting point (Celsius)
76.00
Melting point (Kelvin)
349.15
Boiling point (Celsius)
265.00
Boiling point (Kelvin)
538.15
General information
Molecular weight
136.15g/mol
Molar mass
136.1480g/mol
Density
1.0807g/cm3
Appearence

Phenylacetic acid is a white crystalline solid. It tends to form colorless needles when crystallized from hot water. The compound has a penetrating and unpleasant odor, often described as honey-like or as possessing a floral odor.

Comment on solubility

Solubility of 2-phenylacetic acid

2-phenylacetic acid (C8H8O2) exhibits noteworthy solubility characteristics that are influenced by its structure and functional groups. This compound is primarily characterized as:

  • Soluble in organic solvents: 2-phenylacetic acid dissolves quite well in organic solvents such as ethanol, ether, and chloroform due to its hydrophobic aromatic side chain, which enhances its interactions with nonpolar environments.
  • Limited solubility in water: Although it has a carboxylic acid functional group that can form hydrogen bonds with water, the overall solubility in aqueous solutions is moderate. Its solubility in water is approximately 0.5 g/100 mL, which indicates a significant preference for organic solvents over water.

In summary, while 2-phenylacetic acid may not be highly soluble in water, its solubility in various organic solvents makes it a versatile compound in chemical processes. This behavior underscores the importance of considering both the polar and nonpolar characteristics of compounds in solubility assessments.

Interesting facts

Interesting Facts About 2-Phenylacetic Acid

2-Phenylacetic acid, often referred to as β-phenylacetic acid, is a fascinating compound with a variety of applications and interesting properties in the field of chemistry. Here are some key points that showcase its significance:

  • Natural Occurrence: This compound is not just a synthetic product; it can be found naturally in certain plant species, where it contributes to their aroma and flavor.
  • Role in Synthesis: 2-Phenylacetic acid serves as an important building block in the synthesis of various pharmaceutical products. It is used in the production of α-phenylacetamide, which is an intermediate in the synthesis of numerous drugs.
  • Flavoring Agent: With a subtle, sweet, and slightly floral scent, 2-phenylacetic acid is often utilized as a flavoring agent in the food industry, especially in confections and beverages.
  • Fragrance Component: Beyond its applications in foods, it is a component in perfumes and fragrances, where it imparts a pleasant aroma that can enhance the overall scent profile.
  • Biochemical Significance: It is noteworthy for its role in certain biological processes, particularly in the metabolism of certain amino acids, making it a subject of interest in biochemistry.
  • Analytical Chemistry: Researchers have utilized 2-phenylacetic acid in various analytical techniques to identify and quantify compounds in complex mixtures.

In addition to these points, the chemical structure of 2-phenylacetic acid includes both a carboxylic acid functional group and a phenyl group, which contributes to its unique reactivity and interaction with other molecules. The compound is a prime example of how organic chemistry can bridge the gap between natural occurrences and industrial applications.

As interesting as its uses are, it is also a reminder of the intricate relationships between chemistry, biology, and industry, highlighting the importance of molecular structure in determining a compound's functionality.

Synonyms
PHENYLACETIC ACID
2-Phenylacetic acid
Benzeneacetic acid
103-82-2
Phenylethanoic acid
Acetic acid, phenyl-
alpha-Toluic acid
Benzenacetic acid
phenylacetate
Benzylformic acid
Phenyllacetic acid
Benzylcarboxylic acid
Kyselina fenyloctova
Phenylacetic acid (natural)
omega-Phenylacetic acid
FEMA No. 2878
PHENYL ACETIC ACID
.alpha.-Toluic acid
Kyselina fenyloctova [Czech]
NSC 125718
CHEBI:30745
BRN 1099647
HSDB 5010
.omega.-Phenylacetic acid
AI3-08920
EINECS 203-148-6
UNII-ER5I1W795A
ER5I1W795A
DTXSID2021656
PHENYL-ACETIC ACID
MFCD00004313
NSC-125718
CHEMBL1044
DTXCID201656
EC 203-148-6
4-09-00-01614 (Beilstein Handbook Reference)
Benzeneacetate
NSC125718
2-phenylethanoate
NCGC00159477-02
1173020-54-6
51146-16-8
ASTUGENAL COMPONENT PHENYLACETIC ACID
17303-65-0
ANTINEOPLASTON AS 2-1 COMPONENT PHENYLACETIC ACID
ANTINEOPLASTON AS2-1 COMPONENT PHENYLACETIC ACID
CAS-103-82-2
TROPICAMIDE IMPURITY D (EP IMPURITY)
TROPICAMIDE IMPURITY D [EP IMPURITY]
BENZYLPENICILLIN SODIUM IMPURITY B (EP IMPURITY)
BENZYLPENICILLIN SODIUM IMPURITY B [EP IMPURITY]
BENZYLPENICILLIN POTASSIUM IMPURITY B (EP IMPURITY)
BENZYLPENICILLIN POTASSIUM IMPURITY B [EP IMPURITY]
PROCAINE BENZYLPENICILLIN IMPURITY E (EP IMPURITY)
PROCAINE BENZYLPENICILLIN IMPURITY E [EP IMPURITY]
Phenylethanoate
Phenylessigsaure
w-Phenylacetate
phenylactic acid
a-Toluate
a-Toluic acid
Benzeneacetiic acid
omega-Phenylacetate
organic white solid
w-Phenylacetic acid
Phenylacetate, XIX
Phenylacetic Acid-d7
2-phenyl-acetic acid
Phenylacetic acid, 99%
Phenyl-13C6-acetic acid
bmse000220
Epitope ID:116202
SCHEMBL1459
PHENYLACETIC ACID [MI]
PHENYLACETIC ACID [FCC]
PHENYLACETIC ACID [FHFI]
PHENYLACETIC ACID [HSDB]
BDBM16419
a-Tolylic acid;benzeneacetic acid
QCA53827
YWB02054
Phenylacetic acid_GurudeebanSatyavani
Tox21_113042
Tox21_200533
NSC139637
Phenylacetic acid, natural, >=99%
STK297835
Phenylacetic acid, analytical standard
AKOS000291351
Tox21_113042_1
DB09269
DL-0063
FP31793
NSC-139637
Phenylacetic acid, >=99%, FCC, FG
NCGC00159477-03
NCGC00159477-05
NCGC00258087-01
BP-11383
NCI60_000596
NCI60_002571
Phenylacetic acid, natural, >=99%, FG
DB-003759
DB-055176
NS00115879
Phenylacetic acid, plant cell culture tested
C07086
Q410842
8727557E-AA75-49E9-8E5A-7A2412D71888
BENZYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY B { EP IMPURITY]
InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10
203-148-6
Tropicamide impurity D (Phenylacetic acid - Drug Precursor), European Pharmacopoeia (EP) Reference Standard