Sodium tert-pentoxide

Base Information

• Chemical Name: Sodium tert-pentoxide
• CAS No.: 14593-46-5
• Deprecated CAS: 120380-11-2
• Molecular Formula: C5H11NaO
• Molecular Weight: 110.132
• Hs Code.: 29051990
• European Community (EC) Number: 238-639-4
• UNII: 51Z39PY5Z8
• DSSTox Substance ID: DTXSID4044583
• Nikkaji Number: J241.320E
• Wikidata: Q27260933
• Mol file: 14593-46-5.mol

Synonyms:Sodiumtert-amylate.;tert-Amyl alcoholsodium salt;2-Butanol,2-methyl-, sodium salt (9CI);Sodium, tert-pentyloxide (6CI,7CI);tert-Pentylalcohol, sodium salt (8CI);Sodium 1,1-dimethylpropoxide;Sodium 2-methyl-2-butoxide;

Chemical Property of Sodium tert-pentoxide

Chemical Property:

• Appearance/Colour: Cream or light tan powder
• Vapor Pressure: 19.2mmHg at 25°C
• Melting Point: 200 °C
• Refractive Index: n20/D1.415
• Boiling Point: 113.1 °C at 760 mmHg
• Flash Point: 36.7 °C
• PSA: 23.06000
• Density: 0.904 g/mL at 25 °C
• LogP: 1.60550
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 110.07075925
• Heavy Atom Count: 7
• Complexity: 43.3

Purity/Quality:

40% ^*data from raw suppliers

Sodium tert pentoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-14/15-35-14-40-37-19-67-65-48/20-63
• Safety Statements: 6-22-33-36/37/39-7/8-45-43C-26-16-43-62

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)[O-].[Na+]
• Uses: Sodium tert-pentyloxide is a effective base for the alkylation of ketones.

Technology Process of Sodium tert-pentoxide

There total 3 articles about Sodium tert-pentoxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.6%

tert-Amyl alcohol (75-85-4) → sodium tert-pentoxide (14593-46-5)

Guidance literature:

With sodium; In n-heptane; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1039/c8dt01545g

Reference yield:

tert-Amyl alcohol (75-85-4) + FeCl3*6H2O → sodium tert-pentoxide (14593-46-5)

Guidance literature:

With sodium; In tert-butyl alcohol;

Reference yield:

→ sodium tert-pentoxide (14593-46-5)

Guidance literature:

upstream raw materials:

tert-Amyl alcohol

Downstream raw materials:

Thiophene-2,5-dicarboxylic acid

cyclohexa-1,3-diene

(+)-(R)-methoxyphenylethane

(E)-ethyl 5-phenylpent-4-enoate

Refernces

Synthesis of 5 acetoxy 9 oxotridecanolactone. A model for erythronolide B

10.1016/S0040-4039(01)91879-9

The study details the synthesis of 5-acetoxy-9-oxotridecanolactone as a model for erythronolide B, the aglycone of erythromycin B. The researchers aimed to develop a route to 5-acetoxy-13-hydroxy-9-oxotridecanoic acid, with the intention of lactonization at the final stage of macrolide synthesis. The synthesis involved assembling a thirteen-carbon backbone from two cyclopentanoid and one propanoid unit. Key steps included alkylation of the potassio salt of cyclopentanone carboxylic ester with 1,3-dibromopropane, decarboxylation with HBr, Baeyer-Villiger oxidation using CF3CO3H, and further alkylation and decarboxylation steps. The study also involved protecting and unmasking the cyclopentanone carbonyl group, reduction of an ester group with LiAlH4, and oxidation with Collins' reagent. The final lactonization was achieved using p-toluenesulfonyl chloride and Et3N, or alternatively, 1,1'-carbonyldiimidazole and sodium t-amylate. The synthetic route demonstrated potential applicability to erythronolide and other macrolide systems.

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