Phenylacetic acid

Phenylacetic acid
Names
	Preferred IUPAC name Phenylacetic acid
	Systematic IUPAC name 2-Phenylethanoic acid
	Other names α-Toluic acid; Benzeneacetic acid; 2-Phenylacetic acid; β-Phenylacetic acid
Identifiers
CAS Number	103-82-2 ;
3D model (JSmol)	Interactive image;
3DMet	B02157;
Beilstein Reference	1099647
ChEBI	CHEBI:30745 ;
ChEMBL	ChEMBL1044 ;
ChemSpider	10181341 ;
DrugBank	DB09269;
ECHA InfoCard	100.002.862
EC Number	203-148-6;
Gmelin Reference	68976
KEGG	C07086;
PubChem CID	999;
RTECS number	AJ2430000;
UNII	ER5I1W795A ;
CompTox Dashboard (EPA)	DTXSID2021656 ;
	InChI InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) Key: WLJVXDMOQOGPHL-UHFFFAOYSA-N ; InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) Key: WLJVXDMOQOGPHL-UHFFFAOYAR;
	SMILES O=C(O)Cc1ccccc1;
Properties
Chemical formula	C8H8O2
Molar mass	136.15 g/mol
Appearance	white solid
Odor	honey-like
Density	1.0809 g/cm3
Melting point	76 to 77 °C (169 to 171 °F; 349 to 350 K)
Boiling point	265.5 °C (509.9 °F; 538.6 K)
Solubility in water	15 g/L
Acidity (pKa)	4.31 (H2O)
Magnetic susceptibility (χ)	-82.72·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H319
Precautionary statements	P264, P280, P305+P351+P338, P310, P337+P313
NFPA 704 (fire diamond)	2 1 0
Safety data sheet (SDS)	External MSDS
Legal status	BR: Class D1 (Drug precursors);
Related compounds
Related compounds	Benzoic acid, Phenylpropanoic acid, Cinnamic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Phenylacetic acid (conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China.^[3]

^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ "List of Regulated Drug Precursor Chemicals in China". Archived from the original on 17 August 2015. Retrieved 27 April 2015.

[CRC97-1] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

[2] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[3] "List of Regulated Drug Precursor Chemicals in China". Archived from the original on 17 August 2015. Retrieved 27 April 2015.

[1]

[2]

[3]

Names


Preferred IUPAC name Phenylacetic acid
Systematic IUPAC name 2-Phenylethanoic acid
Other names α-Toluic acid Benzeneacetic acid 2-Phenylacetic acid β-Phenylacetic acid
Identifiers
CAS Number	103-82-2^Y
3D model (JSmol)	Interactive image
3DMet	B02157
Beilstein Reference	1099647
ChEBI	CHEBI:30745^Y
ChEMBL	ChEMBL1044^Y
ChemSpider	10181341^Y
DrugBank	DB09269
ECHA InfoCard	100.002.862
EC Number	203-148-6
Gmelin Reference	68976
KEGG	C07086
PubChem CID	999
RTECS number	AJ2430000
UNII	ER5I1W795A^Y
CompTox Dashboard (EPA)	DTXSID2021656
InChI InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)^Y Key: WLJVXDMOQOGPHL-UHFFFAOYSA-N^Y InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) Key: WLJVXDMOQOGPHL-UHFFFAOYAR
SMILES O=C(O)Cc1ccccc1
Properties
Chemical formula	C₈H₈O₂
Molar mass	136.15 g/mol
Appearance	white solid
Odor	honey-like
Density	1.0809 g/cm³
Melting point	76 to 77 °C (169 to 171 °F; 349 to 350 K)
Boiling point	265.5 °C (509.9 °F; 538.6 K)
Solubility in water	15 g/L
Acidity (pK_a)	4.31 (H₂O)^[1]
Magnetic susceptibility (χ)	-82.72·10⁻⁶ cm³/mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H319
Precautionary statements	P264, P280, P305+P351+P338, P310, P337+P313
NFPA 704 (fire diamond)	2 1 0
Safety data sheet (SDS)	External MSDS
Legal status	BR: Class D1 (Drug precursors)^[2]
Related compounds
Related compounds	Benzoic acid, Phenylpropanoic acid, Cinnamic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references