hexakis(methanidylidyneoxidanium) chromium

• ChemBase ID: 126560
• Molecular Formular: C6CrO6
• Molecular Mass: 220.0567
• Monoisotopic Mass: 219.90999522
• SMILES: [Cr].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-]
• Canonical SMILES: [O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[Cr]
• InChI: InChI=1S/6CO.Cr/c6*1-2
• InChIKey: KOTQLLUQLXWWDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hexakis(methanidylidyneoxidanium) chromium
• IUPAC Traditional name: hexakis(carbon monoxide) chromium
• Synonyms: Chromium(0) hexacarbonyl; Chromium carbonyl; Chromium hexacarbonyl; Hexacarbonylchromium; Chromium hexacarbonyl; Hexacarbonylchromium; 六羰基铬

Database IDs

• CAS Number: 13007-92-6
• EC Number: 235-852-4
• MDL Number: MFCD00010945
• PubChem SID: 24854484; 162220892
• PubChem CID: 25589; 518677
• CHEBI ID: 33031
• Chemspider ID: 23855
• Wikipedia Title: Chromium_hexacarbonyl

CALCULATED PROPERTIES

• Acid pKa: 15.189176
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -3.9616656
• LogD (pH = 7.4): -3.9616656
• Log P: -3.9616656
• Molar Refractivity: 26.2298 cm^3
• Polarizability: 2.2798557 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insoluble in water; soluble in ether, chloroform, tetrahydropyran (THP), methylene chloride
• Apperance: colorless crystals; Crystalline
• Melting Point: >150 °C (dec.)(lit.); 90°C; ca 152°C dec.
• Boiling Point: 210°C (decomp.)
• Flash Point: 210 °C
• Density: 1.77; 1.77 g/cm^3, solid; 1.77 g/mL at 25 °C(lit.)
• Vapor Pressure: 1 mmHg ( 36 °C)
• Vapor Density: 7.6 (vs air)

Safety Information

• Storage Warning: Light Sensitive
• RTECS: GB5075000
• European Hazard Symbols: Toxic (T); X; Harmful (Xn)
• UN Number: 3466; UN3466
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 20/22-44; 22; 5-22
• Safety Statements: 36-45; 53-36-45; 9-36-60
• TSCA Listed: 是
• EU Index: Not listed
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• Main Hazard: Toxic
• NFPA704:
  

  1

  2

  0
• LD50: 150 mg/kg (oral, mouse) ; 230 mg/kg (oral, rat)
• GHS Hazard statements: H301; H301-H331
• GHS Precautionary statements: P210-P280F-P304+P340-P310; P301 + P310
• RID/ADR: UN 3466 6.1/PG 3

Product Information

• Purity: 96%; 98%; 99%
• Grade: technical grade
• Linear Formula: Cr(CO)6

DETAILS

Sigma Aldrich - 241458

Application
Precursor to a prenylatedcarbene complex which promotes a net [5+5] cycloaddition of alkynylbenzaldehydes to give phenanthrenes.1
Packaging
10, 50 g in glass bottle

REFERENCES

• On heating with benzene derivatives readily forms (arene)Cr(CO)₃ complexes, which are often stable, crystalline solids: J. Chem. Soc., 551 (1959). Complex formation is retarded by the presence of electron-withdrawing or bulky substituents. The strongly electron-withdrawing nature of the Cr(CO)₃ group itself activates the aromatic system to metallation, nucleophilic attack, and can also activate side-chain substituents, e.g. to deprotonation. For examples of reactions, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 4, p. 2633.
• Reaction with organolithiums gives Fischer carbene complexes: Chem. Ber., 101, 954 (1968); Org. Synth. Coll., 8, 216 (1993). These react with alkynes to give ɑ-naphthol chromium tricarbonyl complexes (Dotz reaction): Angew. Chem. Int. Ed., 14, 644 (1975); 23, 587 (1984). For an example, see: Org. Synth. Coll., 9, 1 (1998):
  
• For discussion of the mechanism of the Dotz reaction, see: Organometallics, 14, 1492 (1998); 15, 2590 (1999).