SODIUM tert-AMYLOXIDE

PRODUCT IDENTIFICATION

CAS NO. 14593-46-5

SODIUM tert-AMYLOXIDE

EINECS NO. 238-639-4
FORMULA CH3CH2C(CH3)2ONa
MOL WT. 110.13
H.S. CODE  
TOXICITY  
SYNONYMS sodium 2-methyl-2-butanoxide; sodium (2-methyl-2-butoxide);
2-Butanol, 2-methyl, sodium salt; sodium 1,1-dimethyl-1-propoxide; sodium tert-amylate; sodium tert-pentoxide; 2-Butanol, 2-methyl-, sodium salt; sodium 2-methylbutan-2-olate; Sodium tert-pentoxide;
SMILES
 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE Colourless to pale yellow liquid (25% in toluene)
MELTING POINT  
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER Reactive
AUTOIGNITION

 

pH  
VAPOR DENSITY  
NFPA RATINGS  
REFRACTIVE INDEX  
FLASH POINT

 

STABILITY Corrosive, flammable

GENERAL DESCRIPTION & APPLICATIONS

Alkoxide (also called alcoholate ) is the conjugate bases of corresponding alcohol. They contain negatively charged oxygen atom, found as intermediaries in various reactions. Alkoxide is a strong reducing agent. The term alkoxide is for a compound formed from alcohol by replacing the hydrogen of the hydroxy group by a monovalent metal. Metal alkoxides are versatile reagents favoring the chemical reaction of condensation, esterification, alkoxylation and etherification, Claisen condensation, Wolf-Kishner reduction and Stobbe reaction are examples. They are used in wide range of applications in organic synthesis; Agrochemicals; Pharmaceuticals, colorants and aroma chemicals. They are used in manufacturing detergents and biodiesel. They also act as catalysts in polymerization and isomerizations.

  • Alkylation
  • Base catalyzed reaction
  • Cleaning
  • Condensation
  • Dehalogenenation
  • Deprotonations
  • Elimination reaction
  • Enolate formation
  • Isomerization reaction
  • Polymer application
  • Selective metalation
  • Super base application
  • Transesterfication
  • Inorganic superbases are typically salts with highly charged, small negative ions, e.g. lithium nitride, which has extreme negative charge density and so is highly attracted to acids, like the aqueous hydronium ion. Alkali and earth alkali metal hydrides (sodium hydride, calcium hydride) are superbases.

    The base strength can be varied with choice of solvent and the structure of the alcohol. In the dimethyl sulfoxide (DMSO), the ion aggregates are solvated thus increasing the basicity. Alkyl groups in steric bulk of the tertiary alcohol make the alcoholate a stronger base compared to primary alcoholates and hydroxides and influence the speed, selectivity, and specificity. Generally primary alcoholate is soluble in the alcohol from which they are derived only.  But sec-, and tert- alcoholates are soluble in ethers. Furthermore tert- alcoholates have high solubility in the hydrocarbons. In organic synthesis, higher solubility of tertiary alcoholates can generate " Schlosser base (or Lochmann-Schlosser base)" in combination with an alkyl lithium to. The Schlosser base is a commonly used superbase. Butyllithium exists as four-, or six-membered clusters, which are kinetically slow to react. The tertiary alcoholate (butoxide) serves to complex the lithium ion, which breaks the butyllithium clusters. This makes the butyllithium kinetically more reactive. Other such systems are collectively called harpoon bases.

    Alcoholate

    CAS RN

    Sodium Methylate 124-41-4
    Sodium Ethylate 141-52-6
    Sodium n-Propylate 6819-41-6
    Sodium Isopropylate 683-60-3
    Sodium n-Butylate 2372-45-4
    Sodium tert-Butylate 865-48-5
    Sodium tert-Amylate 14593-46-5
    Sodium n-Hexylate 19779-06-7
    Sodium mentholate 19321-38-1
    Potassium Methylate 865-33-8
    Potassium Propylate 16872-93-8
    Potassium Isopropylate 6831-82-9
    Potassium Butylate 589-39-9
    Potassium n-Butylate 3999-70-0
    Potassium tert-Butylate 865-47-4
    Potassium tert-Amylate 41233-93-6
    Potassium-3,7-Dimethyl-3-Octylate 263148-42-1
    SALES SPECIFICATION

    APPEARANCE

    Colourless to pale yellow liquid
    CONTENT

    25%

    TRANSPORTATION
    PACKING  
    HAZARD CLASS 4.2 (Packaging Group: II)
    UN NO. 3206
    OTHER INFORMATION
    Hazard Symbols: C F, Risk Phrases: 11-14-35, Safety Phrases: 6-22-33-36/37/39-7/8