2-phenoxyacetyl chloride

• ChemBase ID: 149986
• Molecular Formular: C8H7ClO2
• Molecular Mass: 170.59298
• Monoisotopic Mass: 170.01345714
• SMILES: c1ccc(cc1)OCC(=O)Cl
• Canonical SMILES: ClC(=O)COc1ccccc1
• InChI: InChI=1S/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2
• InChIKey: PKUPAJQAJXVUEK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenoxyacetyl chloride
• IUPAC Traditional name: 2-phenoxyacetyl chloride
• Synonyms: Phenoxyacetyl chloride; 苯氧乙酰氯

Database IDs

• CAS Number: 701-99-5
• EC Number: 211-862-4
• MDL Number: MFCD00000726
• Beilstein Number: 607585
• PubChem SID: 24887217; 162244148; 24849768
• PubChem CID: 69703

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8268875
• LogD (pH = 7.4): 1.8268875
• Log P: 1.8268875
• Molar Refractivity: 42.4643 cm^3
• Polarizability: 16.647657 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 225-226 °C(lit.); 225-226°C
• Flash Point: 108 °C; 108°C(226°F); 226.4 °F
• Density: 1.235; 1.235 g/mL at 20 °C; 1.235 g/mL at 25 °C(lit.)
• Refractive Index: 1.5340; n20/D 1.534; n20/D 1.534(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3094
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-34; 14-34-36/37
• Safety Statements: 26-36/37/39-45; 8-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H318; H314-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P280-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 3265 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.

Product Information

• Purity: ≥97.0% (GC); 98%
• Grade: technical
• Linear Formula: C6H5OCH2COCl

DETAILS

Sigma Aldrich - 158623

Application
Reagent which generates phenyloxyketene for cycloaddition to imines leading to β-lactams.1,2
Packaging
10, 50, 250 g in glass bottle

REFERENCES

• Can be used to protect OH groups. The phenoxyacetate group is 50x more labile to aqueous ammonia than acetate: Tetrahedron Lett., 4273 (1968). It can also be cleaved with methanolic t-BuNH ₂ : Chem. Lett., 965 (1982).