phenyl chloroformate

• ChemBase ID: 92298
• Molecular Formular: C7H5ClO2
• Molecular Mass: 156.5664
• Monoisotopic Mass: 155.99780708
• SMILES: O(c1ccccc1)C(=O)Cl
• Canonical SMILES: ClC(=O)Oc1ccccc1
• InChI: InChI=1S/C7H5ClO2/c8-7(9)10-6-4-2-1-3-5-6/h1-5H
• InChIKey: AHWALFGBDFAJAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenyl chloroformate
• IUPAC Traditional name: phenyl chloroformate
• Synonyms: Chloroformic acid phenyl ester; Phenyl chloroformate; phenyl carbonochloridate; Phenyl carbonochloridoate; Phenyl chloroformate; PhenylchloroforMate; 苯基氯甲酸酯; 氯甲酸苯酯

Database IDs

• CAS Number: 1885-14-9
• EC Number: 217-547-8
• MDL Number: MFCD00000637
• Beilstein Number: 606778
• PubChem SID: 24853906; 24850214; 162078996; 24854276
• PubChem CID: 15891

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.5872335
• LogD (pH = 7.4): 2.5872335
• Log P: 2.5872335
• Molar Refractivity: 37.9034 cm^3
• Polarizability: 14.823205 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -25°C; -38°C
• Boiling Point: 188-189°C; 74-75 °C/13 mmHg(lit.); 74-75°C/13mm
• Flash Point: 156.2 °F; 69 °C; 69°C; 76°C(169°F)
• Density: 1.246; 1.248; 1.248 g/mL at 25 °C(lit.)
• Refractive Index: 1.511; 1.5110; n20/D 1.511; n20/D 1.511(lit.)
• Vapor Pressure: 1.22 psi ( 20 °C); 1.67 psi ( 55 °C)
• Vapor Density: 1 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive; Very Toxic/Corrosive/Lachrymatory/Moisture Sensitive/Keep Cold
• RTECS: FG3850000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2746; UN2746
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 22-26-34; 22-26-34-43
• Safety Statements: 26-28-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H330-H317-H314-H318-H227; H302-H314-H330
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; P260-P280-P284-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2746 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 95+%; 97%; 99%
• Grade: purum
• Linear Formula: ClCOOC6H5

DETAILS

Sigma Aldrich - 237906

Packaging
5, 100 g in glass bottle

Sigma Aldrich - 167525

Packaging
100 g in glass bottle

REFERENCES

• Precursor of phenyl mixed anhydrides, which can be used, e.g. in peptide coupling reactions.
• Also used in the cleavage of tertiary amines: J. Chem. Soc. (C), 2015 (1967); cf Ethyl chloroformate, L06311, and 1-Chloroethyl chloroformate, L14197. Review: Synthesis, 1 (1989).
• Reagent for dehydration of primary amides to nitriles under mild conditions: Indian J. Chem., 40B, 722 (2001).