Phenyl formate

Phenyl formate
Names
	IUPAC name Phenyl formate
	Other names Formic acid phenyl ester; Methanoic acid phenyl ester; Phenoxyformaldehyde; Phenyl methanoate;
Identifiers
CAS Number	1864-94-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL366050;
ChemSpider	67201;
EC Number	217-471-5;
PubChem CID	74626;
UNII	V4EL38P3VW;
CompTox Dashboard (EPA)	DTXSID30171898;
	InChI InChI=1S/C7H6O2/c8-6-9-7-4-2-1-3-5-7/h1-6H Key: GEOWCLRLLWTHDN-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)OC=O;
Properties
Chemical formula	HCOOC6H5
Molar mass	122.123 g·mol−1
Appearance	Colorless liquid
Odor	Sweet, fruity
Density	1.120 g/cm3 at 20 °C
Boiling point	165.2 °C (760 mmHg); 93-102 °C (90 mmHg); 62 °C (1 mmHg); 35 °C (0.1 mmHg);
Solubility in water	Practically immiscible with water (1.65 g/L)
Solubility	Soluble in ethanol, diethyl ether, benzene and oils.
Solubility in methanol	1104.95 g/L
Solubility in ethanol	1072.45 g/L
Solubility in isopropanol	611.03 g/L
Vapor pressure	2.49 mmHg
Refractive index (nD)	1.511
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Serious eye and respiratory irritation
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	71 °C (160 °F; 344 K)
Related compounds
Related compounds	Phenyl acetate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phenyl formate is an organic compound with the formula HCOOC₆H₅, often abbreviated as HCOOPh, where Ph stands for phenyl. It is a colorless liquid with a characteristic sweet, fruity odor. It is the phenyl ester of formic acid.

Synthesis

Phenyl formate is synthesized by the esterification reaction between formic acid and phenol at 105 °C for 4 hours, in toluene as a solvent, using an acid as a catalyst such as p-toluenesulfonic acid.^[8]^[4]

HCOOH + C₆H₅OH → HCOOC₆H₅ + H₂O

Uses

Phenyl formate releases carbon monoxide and phenol under relatively mild conditions, often catalyzed by a weak base, like tertiary amines.^[5]

HCOOC₆H₅ C₆H₅OH + CO

This property of phenyl formate avoids the necessity of direct usage of carbon monoxide and the hazards of high toxicity and flammability associated with it.^[4]

The chemical control of the rate of carbon monoxide generation is the key to the development of the external carbon monoxide-free palladium-catalyzed phenoxycarbonylation of haloarenes at room temperature. Because of the mild reaction conditions and wide range of substrates, the phenoxycarbonylation makes a general, safe, and practical method to synthesize arenecarboxylic acid esters.^[5]

Phenyl formate is used as a flavoring agent in the food industry.^[2] It is also used for the formylation of amines.^[9]

Reactions

The reaction of phenyl formate with ammonia, primary and secondary amines (known as aminolysis) results in the formation of formamides and phenol.^[4]

HCOOC₆H₅ + NH₃ → HCONH₂ + C₆H₅OH

HCOOC₆H₅ + NH(CH₃)₂ → HCON(CH₃)₂ + C₆H₅OH

References

^ PubChem. "Phenyl formate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-03-17.
^ ^a ^b ^c ^d cymitquimica.com. "CAS 1864-94-4: Phenyl formate". cymitquimica.com. Retrieved 2026-03-17.
^ ^a ^b ^c Sigma-Aldrich. "Phenyl formate". www.sigmaaldrich.com. Retrieved 2026-03-17.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l BENCHCHEM. "Phenyl formate chemical properties and structure" (PDF). pdf.benchchem.com. Retrieved 2026-03-17.
^ ^a ^b ^c Konishi, Hideyuki; Matsubara, Mika; Mori, Keisuke; Tokiwa, Takaki; Arulmozhiraja, Sundaram; Yamamoto, Yuta; Ishikawa, Yoshinobu; Hashimoto, Hiroshi; Shigeta, Yasuteru; Tokiwa, Hiroaki; Manabe, Kei (2017). "Mechanistic Insight into Weak Base-Catalyzed Generation of Carbon Monoxide from Phenyl Formate and itItspplication to Catalytic Carbonylation at Room Temperature without Use of External Carbon Monoxide Gas". Advanced Synthesis & Catalysis. 359 (20): 3592–3601. doi:10.1002/adsc.201700751.
^ Chemical Book. "PHENYL FORMATE". www.chemicalbook.com. Retrieved 2026-03-17.
^ TCI. "Phenyl Formate". www.tcichemicals.com. Retrieved 2026-03-17.
^ Chemical Book. "PHENYL FORMATE synthesis". www.chemicalbook.com. Retrieved 2026-03-17.
^ ThermoFisher. "Phenyl formate, 95%". www.thermofisher.com. Retrieved 2026-03-17.

[pubchem-1] PubChem. "Phenyl formate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-03-17.

[cymitquimica-2] ymitquimica.com. "CAS 1864-94-4: Phenyl formate". cymitquimica.com. Retrieved 2026-03-17.

[sigmaaldrich-3] Sigma-Aldrich. "Phenyl formate". www.sigmaaldrich.com. Retrieved 2026-03-17.

[benchchem-4] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l BENCHCHEM. "Phenyl formate chemical properties and structure" (PDF). pdf.benchchem.com. Retrieved 2026-03-17.

[wiley-5] Konishi, Hideyuki; Matsubara, Mika; Mori, Keisuke; Tokiwa, Takaki; Arulmozhiraja, Sundaram; Yamamoto, Yuta; Ishikawa, Yoshinobu; Hashimoto, Hiroshi; Shigeta, Yasuteru; Tokiwa, Hiroaki; Manabe, Kei (2017). "Mechanistic Insight into Weak Base-Catalyzed Generation of Carbon Monoxide from Phenyl Formate and itItspplication to Catalytic Carbonylation at Room Temperature without Use of External Carbon Monoxide Gas". Advanced Synthesis & Catalysis. 359 (20): 3592–3601. doi:10.1002/adsc.201700751.

[chemicalbook-6] Chemical Book. "PHENYL FORMATE". www.chemicalbook.com. Retrieved 2026-03-17.

[tcichemicals-7] TCI. "Phenyl Formate". www.tcichemicals.com. Retrieved 2026-03-17.

[chemicalbook-synthesis-8] Chemical Book. "PHENYL FORMATE synthesis". www.chemicalbook.com. Retrieved 2026-03-17.

[thermofisher-9] ThermoFisher. "Phenyl formate, 95%". www.thermofisher.com. Retrieved 2026-03-17.

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