Sodium tert-pentoxide solution 40% in toluene

• CAS: 14593-46-5
• Catalog Number: ACM14593465-1
• Category: Alkanes
• Molecular Weight: 110.13g/mol
• Molecular Formula: C5H11NaO
• Synonyms: 2-methyl-2-butanosodiumsalt;sodiumt-amylate,sta;sodiumt-amylate,sta,in;sodiumt-amylate,sta,inhexanes;sodiumt-amylate,sta,int-amylalcohol;sodiumt-amylate,sta,intetrahydrofuran;sodiumt-amylate,sta,intoluene;STA
• IUPAC Name: sodium;2-methylbutan-2-olate
• Canonical SMILES: CCC(C)(C)[O-].[Na+]
• InChI: InChI=1S/C5H11O.Na/c1-4-5(2,3)6;/h4H2,1-3H3;/q-1;+1
• InChI Key: CGRKYEALWSRNJS-UHFFFAOYSA-N
• Complexity: 43.3
• Covalently-Bonded Unit Count: 2
• EC Number: 238-639-4
• Exact Mass: 110.070759g/mol
• Formal Charge: 0
• Hazard Statements: H318
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Heavy Atom Count: 7
• Monoisotopic Mass: 110.070759g/mol
• RIDADR: NONH for all modes of transport
• Rotatable Bond Count: 1
• Symbol: GHS05
• UNII: 51Z39PY5Z8

Case Study

Organic Primary Cell Composed of Citric Acid and Sodium Tert-Amylate

Huang, Tao, et al. Journal of Electroanalytical Chemistry, 2022, 920, 116582.

An organic primary cell is reported, with sodium tert-amylate as the negative electrode and citric acid as the positive electrode. It is a novel all-organic electrochemical system.
Design of organic primary cell system
· Sodium tert-amylate negative electrode material: Through DFT calculation, it is found that the sodium oxygen bond binding energy on sodium tert-amylate is within the range of organic electrode materials (58kcal/mol), indicating that it is easy to release electrons and sodium ions. Sodium tert-amylate exists in a stable sodium state at room temperature and is suitable for preparing electrode materials for organic primary batteries. Sodium tert-amylate does not contain a conjugated structure, and its stability comes from the tert-butyl group.
· Citric acid positive electrode material: Sourced from lemons, citric acid is both eco-friendly and sustainable.
· Advantages: The use of organic materials for both electrodes simplifies waste management in comparison to that associated with inorganic primary cells.

Sodium Tert-Amyl Alcoholate for the Synthesis of Tetrahydropyrazolopyrazine Building Blocks

Shu, Lianhe, et al. Organic Process Research & Development, 2012, 16(11), 1870-1873.

The synthesis route for tetrahydropyrazolopyrazine building blocks involved preparing 5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamine from 5-nitro-2H-pyrazole-3-carboxylic acid through three steps which resulted in an 80% yield. The target product was synthesized by coupling the compound with 4-bromo-6-chloro-2-methyl-2H-pyridazin-3-one using sodium tert-amyl alcoholate and obtaining an 87% yield. The manufacturing process reached several hundred grams in scale successfully.
Coupling Reaction Under Transition Metal-Free Conditions
· The reaction between 5-Methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamine (7) and 1.0 equivalent of sodium tert-pentoxide occurred in THF at room temperature.
· Next, the reaction received a dropwise addition of 0.5 equivalent of pyridazinone 8 while maintaining the temperature below 35 °C. HPLC analysis after the consumption of 8 showed the formation of a nearly 1:1 mixture of compounds 7 and 9.
· The procedure continued by adding 0.5 equivalent of sodium tert-pentoxide together with a 0.25 equivalent of 8 through dropwise addition. The alternating additive pattern occurred two additional times with each cycle using 0.25 equivalents of sodium tert-pentoxide and 0.125 equivalents of compound 8 resulting in complete reaction as HPLC analysis confirmed.
· The reaction stopped when acetic acid and water were added. After filtration the compound 9 was produced as a white solid with an 87% yield. Compound 9 reached its highest dilution level at 12 volumes.