Phenyl formate

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Phenyl formate
Phenyl formate molecule
Names
IUPAC name
Phenyl formate
Other names
  • Formic acid phenyl ester[1]
  • Methanoic acid phenyl ester
  • Phenoxyformaldehyde[2]
  • Phenyl methanoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 217-471-5
UNII
  • InChI=1S/C7H6O2/c8-6-9-7-4-2-1-3-5-7/h1-6H
    Key: GEOWCLRLLWTHDN-UHFFFAOYSA-N
  • C1=CC=C(C=C1)OC=O
Properties
HCOOC6H5
Molar mass 122.123 g·mol−1
Appearance Colorless liquid[2][3]
Odor Sweet, fruity[2]
Density 1.120 g/cm3 at 20 °C[3][4]
Boiling point
  • 165.2 °C (760 mmHg)[4]
  • 93-102 °C (90 mmHg)[5]
  • 62 °C (1 mmHg)[6]
  • 35 °C (0.1 mmHg)[7]
Practically immiscible with water (1.65 g/L)[4]
Solubility Soluble in ethanol, diethyl ether, benzene and oils.[4]
Solubility in methanol 1104.95 g/L[4]
Solubility in ethanol 1072.45 g/L[4]
Solubility in isopropanol 611.03 g/L[4]
Vapor pressure 2.49 mmHg[4]
1.511[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Serious eye and respiratory irritation
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 71 °C (160 °F; 344 K)[3]
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).
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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 NR3→ 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

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