hexachloropropan-2-one

• ChemBase ID: 104829
• Molecular Formular: C3Cl6O
• Molecular Mass: 264.7495
• Monoisotopic Mass: 261.8080307
• SMILES: ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
• Canonical SMILES: O=C(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
• InChI: InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9
• InChIKey: DOJXGHGHTWFZHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hexachloropropan-2-one
• IUPAC Traditional name: hexachloroacetone
• Synonyms: Hexachloroacetone; Hexachloro-2-propanone; HEXACHLORO-2-PROPANONE; HEXACHLOROACETONE PRACTICAL GRADE; perchloroacetone; HCA; Hexachloroacetone; Hexachloro-2-propanone; Hexachloroacetone; 六氯丙酮; 六氯-2-丙酮; 六氯丙酮

Database IDs

• CAS Number: 116-16-5
• EC Number: 204-129-5
• MDL Number: MFCD00000796
• Beilstein Number: 1707475
• PubChem SID: 24846842; 24895685; 162093054
• PubChem CID: 8303
• Chemspider ID: 13873693
• KEGG ID: C19122
• Wikipedia Title: Hexachloroacetone

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.6110566
• LogD (pH = 7.4): 3.6110566
• Log P: 3.6110566
• Molar Refractivity: 47.224 cm^3
• Polarizability: 18.095913 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -2°C; -2°C; -6--2 °C(lit.)
• Boiling Point: 203-205°C; 204°C; 66-70 °C/6 mmHg(lit.)
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.444 g/cm^3; 1.74 g/ml; 1.743 g/mL at 25 °C(lit.); 1.748
• Refractive Index: 1.5115; n20/D 1.511; n20/D 1.511(lit.)

Safety Information

• RTECS: UC2100000
• European Hazard Symbols: Nature polluting (N); X; Harmful (Xn)
• UN Number: 2661; UN2661
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22-51/53
• Safety Statements: 24/25-61
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H411
• GHS Precautionary statements: P273; P273-P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2661 6.1/PG 3

Product Information

• Purity: ≥98.0% (GC); ≥99.0% (GC); 98%; 99%
• Grade: PRACTICAL; produced by Wacker; purum
• Linear Formula: CCl3COCCl3

DETAILS

MP Biomedicals - 02157343

(Hexachloroacetone)
Purity: 98%
1 ml = approx. 1.74 g

MP Biomedicals - 05213580

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 10894

Other Notes
prices for bulk quantities on request
Packaging
1 kg in glass bottle

Sigma Aldrich - H5308

Packaging
250 g in glass bottle
Application
Reagent used for the conversion of nucleoside-3′-phosphonates to the corresponding phosphates1 and for the polymerization of vinyl compounds.2

Sigma Aldrich - 52080

Other Notes
High boiling substitute for CCl4 in the regio- and stereoselective preparation of allylic chlorides from allylic alcohol with triphenylphosphine1,2; Reagent for the chlorination of enamines3

REFERENCES

• In combination with triphenylphosphine, converts primary and secondary allylic alcohols to their chlorides without isomerization: Tetrahedron Lett., 2999 (1977). Tertiary allylic alcohols do undergo allylic rearrangement to give the less substituted chloride: J. Org. Chem., 44, 359 (1979), but cyclopropyl carbinols are converted to their chlorides without rearrangement: J. Org. Chem., 49, 431 (1984). The method is also applicable to the mild conversion of carboxylic acids to acid chlorides: Tetrahedron Lett., 38, 6489 (1997); see also Trichloroacetonitrile, A10565.
• Reagent for protection of amino groups as their N-trichloroacetyl derivatives under neutral conditions: J. Org. Chem., 35, 2423 (1970); Org. Synth. Coll., 5, 1074 (1973). The group can be cleaved with NaBH₄ in ethanol: Chem. Ber., 103, 2437 (1970).
• With strong base, e.g. alkoxide, is a source of dichlorocarbene. For a review, see: Org. React., 13, 55 (1963).