Phenyl formate
Topic: Chemistry
From HandWiki - Reading time: 4 min
| |
| Names | |
|---|---|
| IUPAC name
Phenyl formate
| |
| Other names | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
| EC Number |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| HCOOC 6H 5 | |
| 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 | |
| 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 |
| 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 | |
| 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
6H
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.
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
6H
5OH → HCOOC
6H
5 + H
2O
Uses
Phenyl formate releases carbon monoxide and phenol under relatively mild conditions, often catalyzed by a weak base, like tertiary amines.[5]
- HCOOC
6H
5 C
6H
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
6H
5 + NH
3 → HCONH
2 + C
6H
5OH - HCOOC
6H
5 + NH(CH
3)
2 → HCON(CH
3)
2 + C
6H
5OH
References
- ↑ PubChem. "Phenyl formate". https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl-formate.
- ↑ 2.0 2.1 2.2 2.3 cymitquimica.com. "CAS 1864-94-4: Phenyl formate". https://cymitquimica.com/cas/1864-94-4/.
- ↑ 3.0 3.1 3.2 Sigma-Aldrich. "Phenyl formate". https://www.sigmaaldrich.com/GB/en/sds/sial/06556.
- ↑ 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.
- ↑ 5.0 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.
- ↑ Chemical Book. "PHENYL FORMATE". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1364464.htm.
- ↑ TCI. "Phenyl Formate". https://www.tcichemicals.com/CA/en/p/P2770.
- ↑ Chemical Book. "PHENYL FORMATE synthesis". https://www.chemicalbook.com/synthesis/phenyl-formate.htm.
- ↑ ThermoFisher. "Phenyl formate, 95%". https://www.thermofisher.com/order/catalog/product/L00289.14.
 |  |
EncycloReader
is supported by the 
KSF