| Identification | More | [Name]
Lead tetraacetate | [CAS]
546-67-8 | [Synonyms]
LEAD(+4)ACETATE
LEAD ACETATE
LEAD(IV) ACETATE
LEAD(IV) ACETATE GM
LEAD(IV) TETRAACETATE
LEAD TETRAACETATE
LTA
PB(ACAC)4
Acetic acid, lead(4+) salt
Aceticacid,lead(4+)salt
aceticacid,lead(4++)salt
leadacetate(pb(o2c2h3)4)
leadacetate(pb(oac)4)
leadtetracetate
plumbicacetate
Tetrakis(acetyloxy)plumbane
tetra-leadacetat
Pb(acac)4
Lead(IV) acetate (5-10% acetic acid)
Leadacetateaceticacidwhitetolightbrownxtl | [EINECS(EC#)]
208-908-0 | [Molecular Formula]
C8H12O8Pb-2 | [MDL Number]
MFCD00008693 | [Molecular Weight]
443.38 | [MOL File]
546-67-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White solid | [Melting point ]
175-180 °C
| [Boiling point ]
118.1°C | [density ]
2,28 g/cm3 | [storage temp. ]
0-6°C | [form ]
Crystalline Powder | [color ]
White to light orange-pink | [Specific Gravity]
2.28 | [Stability:]
Stable. Moisture sensitive. Incompatible with water, most metals. | [Water Solubility ]
Decomposition | [Hydrolytic Sensitivity]
7: reacts slowly with moisture/water | [Sensitive ]
Moisture Sensitive | [Merck ]
14,5423 | [BRN ]
3595640 | [InChIKey]
JEHCHYAKAXDFKV-UHFFFAOYSA-J | [CAS DataBase Reference]
546-67-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Lead tetraacetate(546-67-8) | [EPA Substance Registry System]
546-67-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,O | [Risk Statements ]
R61:May cause harm to the unborn child.
R8:Contact with combustible material may cause fire.
R20/22:Harmful by inhalation and if swallowed .
R33:Danger of cumulative effects.
R35:Causes severe burns.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R62:Possible risk of impaired fertility. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S17:Keep away from combustible material . | [RIDADR ]
UN 2923 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
AI5300000
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29152900 | [Hazardous Substances Data]
546-67-8(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
Faintly pink wet crystals with an odor of vinegar. | [Reactivity Profile]
Organometallics are strongly reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents. Often reactive with water to generate toxic or flammable gases. Generally highly toxic. Often react on contact with tissues to give toxic products. | [Air & Water Reactions]
Unstable in air. Reacts with water to form brown lead dioxide and acetic acid [Merck 11th ed. 1989]. | [Health Hazard]
Early symptoms of lead intoxication by ingestion are most commonly gastrointestinal disorders, colic, constipation, etc.; weakness, which may go on to paralysis chiefly of the extensor muscles of the wrists and less often of the ankles, is noticeable in the most serious cases. Ingestion of a large amount causes local irritation of the alimentary tract; pain, leg cramps, muscle weakness, paresthesias, depression, coma, and death may follow in 1 or 2 days. Contact causes severe irritation of eyes and can burn skin. | [Fire Hazard]
Behavior in Fire: Can increase the intensity of a fire when in contact with combustible material. Cool containers with plenty of water. | [Description]
Lead (IV) acetate or lead tetraacetate is a chemical compound with chemical formula Pb(C2H3O2)4 and is a lead salt of acetic acid. It is commercially available often stabilized with acetic acid. | [Chemical Properties]
Lead tetraacetate (plumbic acetate), Pb(C2H3O2)4, is a colorless, monoclinic crystalline solid that is soluble in chloroform and in hot acetic acid, but decomposes in cold water and in ethyl alcohol. Lead tetraacetate can be prepared by adding warm, water-free, glacial acetate acid to red lead, Pb3O4, and subsequent cooling. The salt decomposes with the addition of water to give PbO2, but the yield can be improved by passing in chlorine gas. Lead tetraacetate is available in laboratory quantities as colorless to faintly pink crystals stored in glacial acetic acid. | [Chemical Properties]
White solid | [Application]
Lead tetraacetate is a strong oxidizing agent, a source of acetyloxy groups and a general reagent for the introduction of lead into organolead compounds. Some of its many uses in organic chemistry :
Acetoxylation of benzylic, allylic and α-oxygen ether C-H bonds, for example the photochemical conversion of dioxane to 1,4- dioxene through the 2-acetoxy-1,4-dioxane intermediate and the conversion of α-pinene to verbenone
* Oxidation of hydrazones to diazo compounds for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane * Aziridine formation, for example the reaction of Naminophthalimide and stilbene
* Cleavage of 1,2-diols to the corresponding aldehydes or ketones often replacing ozonolysis, for instance the oxidation of di-nbutyl d-tartrate to n-butyl glyoxylate
* Reaction with alkenes to γ-lactones
* Oxidation of alcohols carrying a δ-proton to cyclic ethers.
* Oxidative cleavage of certain allyl alcohols in conjunction with ozone. | [Definition]
ChEBI: An acetate salt with formula Pb(OAc)4. It is used as a selective oxidising agent in organic synthesis. | [Safety]
Lead (IV) acetate may be fatal if ingested, inhaled, or absorbed through skin. It causes irritation to skin, eyes, and respiratory tract. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system. |
| Questions And Answer | Back Directory | [Physical Properties]
Colorless monoclinic crystals; turns pink; unstable in air; density 2.228 g/cm3 at 17°C; melts at 175°C; decomposes in cold water and ethanol; soluble in chloroform, benzene, nitrobenzene, and hot glacial acetic acid; also soluble in concentrated hydrochloric acid.
| [Uses]
Lead tetraacetate is used as a highly selective oxidizing agent in organic synthesis. This includes oxidation of glycols into aldehydes, preparation of cyclohexyl acetate, production of oxalic acid, and in structural analysis of sugars.
| [Preparation]
Lead tetraacetate is prepared by dissolving lead tetroxide in warm glacial acetic acid followed by cooling. On cooling, the tetraacetate crystallizes out while lead acetate remains in the solution:
Pb3O4 + 8CH3COOH→Pb(CH3COO)4 + 2Pb(CH3COO)2 + 4H2O
Yield is improved by adding chlorine gas to the mixture. Alternatively, the compound may be prepared by adding a mixture of glacial acetic acid and acetic anhydride to lead tetroxide and heating the solution gently. Acetic anhydride converts the water formed in the reaction into acetic acid, thus preventing hydrolysis of the product lead tetraacetate.
| [Reactions]
Lead tetraacetate, on treatment with water, hydrolyzes to lead dioxide and acetic acid:
Pb(CH3COO)4 + 2H2O → PbO2 + 4CH3COOH
Lead tetraacetate is a selective oxidizing agent causing oxidative cleavage of polyhydroxy compounds. It cleaves compounds that have hydroxyl groups on adjacent carbon atoms, breaking the carbon-carbon bonds to form carbonyl compounds, such as aldehydes, ketones or acids. The reaction is carried out in organic solvents. A typical example is as follows:
OH—CH2—CH2—OH + Pb(CH3COO)4 → 2CH2O + Pb(CH3COO)2 + 2CH3COOH
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