1,3-dichloropropan-2-one

• ChemBase ID: 64746
• Molecular Formular: C3H4Cl2O
• Molecular Mass: 126.96926
• Monoisotopic Mass: 125.96392011
• SMILES: C(C(=O)CCl)Cl
• Canonical SMILES: ClCC(=O)CCl
• InChI: InChI=1S/C3H4Cl2O/c4-1-3(6)2-5/h1-2H2
• InChIKey: SUNMBRGCANLOEG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dichloropropan-2-one
• IUPAC Traditional name: 1,3-dichloroacetone
• Synonyms: Bis(chloromethyl) Ketone; NSC 8745; sym-Dichloroacetone; α,γ-Dichloroacetone; 1,3-Dichloroacetone; 1,3-DCA; 1,3-Dichloro-2-propanone; 1,3-Dichloroacetone solution; 1,3-Dichloroacetone (sym.); 1,3-Dichloro-2-propanone; α,α'-Dichloroacetone; Bis(chloromethyl) ketone; 1,3-dichloropropan-2-one; 1,3-Dichloroacetone; 1,3-二氯丙酮; 1,3-二氯-2-丙酮; 1,3-二氯丙酮 溶液; 1,3-二氯丙酮（对称）

Database IDs

• CAS Number: 534-07-6
• EC Number: 208-585-6
• MDL Number: MFCD00000937
• Beilstein Number: 605456
• Merck Index: 143052
• PubChem SID: 24861736; 162030485; 24846826; 24850245
• PubChem CID: 10793
• Chemspider ID: 21106513
• Wikipedia Title: Bis(chloromethyl)_ketone

CALCULATED PROPERTIES

• Acid pKa: 15.624696
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.1809675
• LogD (pH = 7.4): 1.1809675
• Log P: 1.1809675
• Molar Refractivity: 25.7012 cm^3
• Polarizability: 10.163034 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline
• Melting Point: 38-43 °C; 39-41 °C(lit.); 40-44°C; 43-45°C
• Boiling Point: 172-173°C; 173 °C(lit.); 173°C; 73 °C/733.4 mmHg(lit.)
• Flash Point: 11 °C; 192.2 °F; 51.8 °F; 89 °C; 89°C(193°F); 95°C(203°F)
• Density: 1.025 g/mL at 20 °C(lit.); 1.383; 1.383 g/mL at 25 °C(lit.); 1.3834^4^6
• Refractive Index: 1.4400
• Vapor Pressure: <0.1 mmHg ( 20 °C)
• Vapor Density: 4.38 (vs air)

Safety Information

• Storage Warning: IRRITANT
• RTECS: UC1430000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Highly toxic (T+)
• UN Number: 2649; 3286; UN2649
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 2; II
• Risk Statements: 11-24-26/28-34-68; 24-26/28-34-68; 24-26/28-34-68-50/53
• Safety Statements: 16-26-28-36/37/39-45; 26-28-36/37/39-45-60-61; 26-36/37/39-45; 4-9-20-26-27/28-36/37/39-45-60
• TSCA Listed: false; 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H300-H310-H314-H330-H336-H341; H300 +H310 + H330-H314-H341; H300-H310-H330-H314-H318-H341; H300-H310-H330-H314-H318-H341-H400-H410
• GHS Precautionary statements: P210-P260-P264-P280-P284-P301 + P310; P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P280-P305+P351+P338-P302+P352-P309-P310-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2649 6.1/PG 2; UN 3286 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; ≥95.0% (GC); 95+%; 96%; typically 99%
• Concentration: 50% in acetone (density determination)
• Grade: produced by Wacker; purum
• Linear Formula: ClCH2COCH2Cl

DETAILS

Sigma Aldrich - 168548

Packaging
10, 50 g in glass bottle

Sigma Aldrich - 10878

Other Notes
prices for bulk quantities on request

REFERENCES

• Successive reaction with a Grignard reagent and Li metal leads to 1-substituted cyclopropanols, which rearrange on thermolysis to ethyl ketones: Synthesis, 647 (1983):
  
• The cyclization can also be induced by ethyl radicals, generated from ethylmagnesium bromide and FeCl₃. This method is applicable only to 1-arylcyclopropanols: J. Org. Chem., 29, 2813 (1964); 43, 3602 (1978); Org. Synth. Coll., 5, 1058 (1973).
• Formation of the acetal followed by treatment with NaNH₂ provides a route to cyclopropenones: Tetrahedron, 48, 2045 (1992).