Phenyl formate

Names
IUPAC name

Phenyl formate

Other names

* Formic acid phenyl ester[1]
* Methanoic acid phenyl ester
* Phenoxyformaldehyde[2]
* 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

| HCOOC

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]

Solubility in water

| 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]

Refractive index (nD)

| 1.511[4]
Hazards
Main hazards | Serious eye and respiratory irritation
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| HH302Script error: No such module "Preview warning".Category:GHS errors, HH315Script error: No such module "Preview warning".Category:GHS errors, HH319Script error: No such module "Preview warning".Category:GHS errors, HH335Script error: No such module "Preview warning".Category:GHS errors

GHS precautionary statements

| PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP264+P265Script error: No such module "Preview warning".Category:GHS errors, PP270Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP301+P317Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP305+P351+P338Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP330Script error: No such module "Preview warning".Category:GHS errors, PP332+P317Script error: No such module "Preview warning".Category:GHS errors, PP337+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP403+P233Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors
NFPA 704 (fire diamond)  |

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).

Infobox references

Phenyl formate is an organic compound with the formula HCOOC

5, 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.

## Contents

* 1 Synthesis
* 2 Uses
* 3 Reactions
* 4 References

## 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 + C

5OH → HCOOC

5 \+ H

## Uses

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

HCOOC

5 NR
3→ C

5OH + 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]

HCOOC

5 \+ NH
3 → HCONH
2 \+ C

5OH
HCOOC

5 \+ NH(CH

2 → HCON(CH

2 \+ C

5OH

## References

1. ↑ PubChem. "Phenyl formate". https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl-formate.
2. ↑ 2.0 2.1 2.2 2.3 cymitquimica.com. "CAS 1864-94-4: Phenyl formate". https://cymitquimica.com/cas/1864-94-4/.
3. ↑ 3.0 3.1 3.2 Sigma-Aldrich. "Phenyl formate". https://www.sigmaaldrich.com/GB/en/sds/sial/06556.
4. ↑ 4.00 4.01 4.02 4.03 4.04 4.05 4.06 4.07 4.08 4.09 4.10 4.11 BENCHCHEM. "Phenyl formate chemical properties and structure". https://pdf.benchchem.com/155/Phenyl_formate_chemical_properties_and_structure.pdf.
5. ↑ 5.0 5.1 5.2 Konishi, Hideyuki; Matsubara, Mika; Mori, Keisuke; Tokiwa, Takaki; Arulmozhiraja, Sundaram; Yamamoto, Yuta; Ishikawa, Yoshinobu; Hashimoto, Hiroshi et al. (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. https://advanced.onlinelibrary.wiley.com/doi/10.1002/adsc.201700751.
6. ↑ Chemical Book. "PHENYL FORMATE". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1364464.htm.
7. ↑ TCI. "Phenyl Formate". https://www.tcichemicals.com/CA/en/p/P2770.
8. ↑ Chemical Book. "PHENYL FORMATE synthesis". https://www.chemicalbook.com/synthesis/phenyl-formate.htm.
9. ↑ ThermoFisher. "Phenyl formate, 95%". https://www.thermofisher.com/order/catalog/product/L00289.14.

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*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency