What is Sodium tert-Butoxide CAS 865-48-5?

Sodium tert-Butoxide, also called sodium tert-butylate or NaOtBu, is a strong, sterically hindered alkoxide base with the formula C4H9NaO, molecular weight 96.10 g/mol, and EC number 212-741-9. It is supplied as a white to off-white hygroscopic powder or as a solution in compatible solvents, and it is widely used in organic synthesis.

Why is Sodium tert-Butoxide preferred over sodium hydride in some pharmaceutical reactions?

Sodium tert-Butoxide is a strong base with bulky tert-butoxide groups, so it can promote deprotonation and coupling steps while being less likely to participate as a nucleophile. In selected pharmaceutical oxygen alkylation or palladium-catalyzed reactions, it can offer a more controlled and safer alternative to sodium hydride because the base is available as a stable powder or solution and can avoid the vigorous hydrogen evolution associated with hydride reagents.

Can NaOtBu be freely substituted by potassium or lithium tert-butoxide?

No. Sodium, potassium, and lithium tert-butoxides are not freely interchangeable because the alkali-metal counterion affects aggregation, solubility, base strength, and reaction selectivity. The correct tert-butoxide should be chosen for the specific solvent system, substrate, and catalytic cycle rather than replacing NaOtBu on a molar basis.

What are the main applications of Sodium tert-Butoxide?

Sodium tert-Butoxide is used for deprotonation, elimination, condensation, rearrangement, and ring-opening reactions. It is especially important in pharmaceutical and fine chemical synthesis, agrochemical intermediates, polymerization or isomerization catalysis, and palladium-catalyzed C-N or C-C coupling such as Buchwald-Hartwig amination.

Why does Sodium tert-Butoxide require dry, air-sensitive handling?

NaOtBu is hygroscopic and reacts vigorously with water, acids, and moisture to form tert-butanol and sodium hydroxide. It should therefore be handled under dry conditions or inert gas, kept away from humidity, and used promptly after opening sealed containers.

How should Sodium tert-Butoxide be stored and supplied?

Store it in tightly sealed, moisture-resistant containers in a cool, dry, well-ventilated area, away from water, acids, oxidizers, heat, and open flames. Solid grades are commonly supplied in sealed drums or air-sensitive containers, while solution grades may be supplied in THF, tert-butanol, or another compatible solvent system to maintain stability during transport and storage.

Sodium tert-Butoxide CAS 865-48-5

Sodium tert-Butoxide is positioned in industrial supply as a highly reactive alkoxide base, commonly used in organic synthesis, condensation reactions, and deprotonation processes. It is valued for its strong basicity and relatively low nucleophilicity, making it suitable for elimination reactions and selective transformations in fine chemical and pharmaceutical intermediate production.

In commercial supply, it is typically provided either as a moisture-sensitive solid powder or as a solution in compatible solvents such as tert-butanol. Due to its high reactivity toward moisture and air, it is handled under controlled conditions and used as a processing reagent rather than a direct formulation ingredient. Standard packaging is available with appropriate moisture protection, along with COA, TDS, and SDS documentation for industrial use.

CAS: 865-48-5
Synonyms: Sodium tert-butylate; Sodium t-butoxide; NaOtBu
Einecs: 212-741-9
Molecular Formula: C₄H₉NaO
Grade: Typically supplied for industrial synthesis and reagent use
Package: Available in sealed, moisture-protected packaging; packaging format depends on solid or solution supply form and order requirements

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Product Description

1 Physicochemical Properties

2 Typical Applications

3 Packaging

4 Storage

Physicochemical Properties

Item	Description
Appearance	White to off-white powder or solid
Odor	Characteristic odor
Solubility	Soluble in alcohols such as tert-butanol; reacts with water
Melting Point	Approx. 180–190°C (decomposition)
Reactivity	Strong base; reacts vigorously with water and acids
Moisture Sensitivity	Highly hygroscopic and moisture sensitive
Handling Characteristics	Air-sensitive; requires dry handling conditions

Typical Applications

Organic synthesis: Used as a strong base in elimination, condensation, and deprotonation reactions.
Pharmaceutical and fine chemical intermediates: Applied in reaction steps requiring controlled base strength and selectivity.
Polymer and specialty chemical processing: Used as a catalyst or initiator in certain polymerization systems.
Transesterification and alkoxide reactions: Acts as a reagent in ester exchange and related transformations.

Use conditions should be carefully evaluated due to its strong reactivity and moisture sensitivity.

For related alkoxide base pages used in organic synthesis, compare Potassium tert-Butoxide and Sodium Methoxide.

Packaging

Sodium tert-Butoxide is supplied in tightly sealed, moisture-resistant containers to protect against air and humidity exposure. Common packaging formats include lined drums, sealed metal containers, or specialized containers for air-sensitive chemicals.

For solution grades, it may be supplied in drums or IBC containers compatible with the solvent system. Packaging is designed to maintain product stability during storage and transportation, with bulk supply arrangements available based on order requirements.

Storage

Store in a cool, dry, and well-ventilated area under inert or low-moisture conditions where possible. Keep containers tightly closed and protected from air and humidity.

Avoid contact with water, acids, and oxidizing agents. Maintain strict moisture control during storage and handling.

FAQ - Technical & Supply Chain

Q:
What is Sodium tert-Butoxide CAS 865-48-5?

A: Sodium tert-Butoxide, also called sodium tert-butylate or NaOtBu, is a strong, sterically hindered alkoxide base with the formula C4H9NaO, molecular weight 96.10 g/mol, and EC number 212-741-9. It is supplied as a white to off-white hygroscopic powder or as a solution in compatible solvents, and it is widely used in organic synthesis.
Q:
Why is Sodium tert-Butoxide preferred over sodium hydride in some pharmaceutical reactions?

A: Sodium tert-Butoxide is a strong base with bulky tert-butoxide groups, so it can promote deprotonation and coupling steps while being less likely to participate as a nucleophile. In selected pharmaceutical oxygen alkylation or palladium-catalyzed reactions, it can offer a more controlled and safer alternative to sodium hydride because the base is available as a stable powder or solution and can avoid the vigorous hydrogen evolution associated with hydride reagents.
Q:
Can NaOtBu be freely substituted by potassium or lithium tert-butoxide?

A: No. Sodium, potassium, and lithium tert-butoxides are not freely interchangeable because the alkali-metal counterion affects aggregation, solubility, base strength, and reaction selectivity. The correct tert-butoxide should be chosen for the specific solvent system, substrate, and catalytic cycle rather than replacing NaOtBu on a molar basis.
Q:
What are the main applications of Sodium tert-Butoxide?

A: Sodium tert-Butoxide is used for deprotonation, elimination, condensation, rearrangement, and ring-opening reactions. It is especially important in pharmaceutical and fine chemical synthesis, agrochemical intermediates, polymerization or isomerization catalysis, and palladium-catalyzed C-N or C-C coupling such as Buchwald-Hartwig amination.
Q:
Why does Sodium tert-Butoxide require dry, air-sensitive handling?

A: NaOtBu is hygroscopic and reacts vigorously with water, acids, and moisture to form tert-butanol and sodium hydroxide. It should therefore be handled under dry conditions or inert gas, kept away from humidity, and used promptly after opening sealed containers.
Q:
How should Sodium tert-Butoxide be stored and supplied?

A: Store it in tightly sealed, moisture-resistant containers in a cool, dry, well-ventilated area, away from water, acids, oxidizers, heat, and open flames. Solid grades are commonly supplied in sealed drums or air-sensitive containers, while solution grades may be supplied in THF, tert-butanol, or another compatible solvent system to maintain stability during transport and storage.

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