benzene-1,2-dicarbonyl dichloride

• ChemBase ID: 147529
• Molecular Formular: C8H4Cl2O2
• Molecular Mass: 203.02216
• Monoisotopic Mass: 201.95883473
• SMILES: c1ccc(c(c1)C(=O)Cl)C(=O)Cl
• Canonical SMILES: ClC(=O)c1ccccc1C(=O)Cl
• InChI: InChI=1S/C8H4Cl2O2/c9-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H
• InChIKey: FYXKZNLBZKRYSS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzene-1,2-dicarbonyl dichloride
• IUPAC Traditional name: phthaloyl chloride
• Synonyms: Phthaloyl dichloride; Phthaloyl chloride; Benzene-1,2-dicarbonyl chloride; Phthaloyl chloride; 邻苯二甲酰氯; 酞酰氯; 临苯二甲酰氯

Database IDs

• CAS Number: 88-95-9
• EC Number: 201-869-0
• MDL Number: MFCD00000666
• Beilstein Number: 608200
• Merck Index: 147375
• PubChem SID: 24887504; 24898487; 162241717
• PubChem CID: 6955

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.3550708
• LogD (pH = 7.4): 2.3550708
• Log P: 2.3550708
• Molar Refractivity: 48.2874 cm^3
• Polarizability: 17.937393 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 12°C; 6-12 °C(lit.)
• Boiling Point: 269-271 °C(lit.); 276°C
• Flash Point: 113 °C; 151°C(304°F); 235.4 °F
• Density: 1.409; 1.409 g/mL at 25 °C(lit.)
• Refractive Index: 1.5680; n20/D 1.568; n20/D 1.568(lit.)
• Vapor Pressure: 30 mmHg ( 47 °C)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-23-26-36/37/39-45-60; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; 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

Product Information

• Purity: ≥90%; 90%; 94%
• Grade: technical
• Impurities: ~8% anhydride
• Linear Formula: C6H4-1,2-(COCl)2

DETAILS

Sigma Aldrich - P40409

Packaging
100, 500 g in Sure/Seal™

Sigma Aldrich - 79830

General description
equilibrium mixture (phthaloyl chloride ~80% and pseudochloride ~10%) both components show equal chemical behaviour

REFERENCES

• Can be used for the preparation of volatile acid chlorides from the acids by exchange and distillation of the product from the reaction medium; see, e.g.: Org. Synth. Coll., 3, 422 (1955). For a one step conversion of ethyl esters to the corresponding acid chlorides, with loss of ethyl chloride, see: J. Org. Chem., 44, 2291 (1979).
• Acts as a trap for the nitrite ion in the fluorodenitration of aromatic substrates with Potassium fluoride, 14130: Chem. Lett., 2213 (1989); J. Org. Chem., 56, 6406 (1991).