Tert-butyllithium CAS 594-19-4
Hexahydrophthalic Anhydride CAS 85-42-7
02/12/2024
Dichlorodimethylsilane CAS 75-78-5
25/11/2024
Base Info:
Name: Tert-butyllithium
CAS: 594-19-4
Purity: 99.5%min
MOQ: 1KG
Directory Guidance on Tert-butyllithium
Product Paramete
| CAS No: | 294-19-4 |
| Name: | Tert-butyllithium |
| EINECS: | 209-831-5 |
| Formula | C4H9Li |
| Weight | 64.06 |
| Brand Name | Look Chemical |
| Place of Origin | China |
| Other Names: | T-butyllithium; Tert-butyl lithium |
| Type: | Organic raw materials; Synthetic intermediates |
| Product Model: | LC-294-19-4 |
| Shelf Life | 3 Years |
| Usage | Used as a lithiation reagent |
| Form | Liquid |
What is Tert-butyllithium?
The chemical properties of organic lithium compounds are similar to those of alkyl magnesium halides, but they are more active and can react with metal halides, carbonyl-containing substances, halogenated hydrocarbons, and compounds containing active hydrogen. Commonly used organic lithium compounds include butyl lithium and phenyl lithium, among which butyl lithium is mainly used to remove active hydrogen from organic compounds. Butyl lithium includes n-butyl lithium and tert-butyllithium. Compared with n-butyl lithium, tert-butyllithium has stronger alkalinity and can remove hydrogen from many hydrogen carbonates, including α-position hydrogen benzene of ethers, so it can be used in many areas where n-butyl lithium is not applicable.
Tert-butyllithium t-C4H9Li, colorless crystalline solid. Similar to n-butyl lithium, but more active. It is thermally stable and rarely decomposes even when heated at 100°C for 20 hours. It is prepared by reacting tert-butyl chloride (containing tert-butyl alcohol) with sodium-containing lithium at reflux temperature in n-pentane. It is used as a polymerization initiator and metallizing agent in the laboratory. Butyl lithium, also known as t-butyl lithium, is an organic lithium compound and a super base in organic synthesis. It exists in the form of clusters and can remove hydrogen from many hydrogen carbonates, including benzene. Tert-butyllithium is highly flammable and can spontaneously combust in the air. It must be protected by dry nitrogen when stored and must be used very carefully.
At present, n-butyllithium can be prepared on a large scale in industry, while tert-butyllithium can only be prepared on a small scale in the laboratory because it is too active and the raw materials are relatively more stable. When it is scaled up to an industrial scale, the reaction is often difficult to initiate, the success rate is low, and the target product cannot be obtained. Due to the huge amount of tert-butyllithium used in basic research and industrial production and its irreplaceability, how to achieve large-scale production of tert-butyllithium has become an urgent problem to be solved.
Physical Properties
Specification
Product Nature
Specification
| Item | Specification |
| Product Name | tert-Butyllithium |
| CAS No. | 594-19-4 |
| Appearance | Colorless to white liquid |
| Shelf Life | 2 years |
| Packing | 1kg/bag,25kg/bag or as your requirements |
Product Nature
- Density: 0.69 g/mL at 20 °C
- Boiling point: 36-40 °C
- Fp: 20 °F
- Vapor density: ~3 (vs air)
- Storage temp: 2-8°C
- Sensitive: Air & Moisture Sensitive
Tert-butyllithium Packaging
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Tert-butyllithium Uses
Tert-butyllithium is mainly used as a lithiation agent, halogen-lithium exchange agent, cyclization agent and strong base to prepare various types of organic compounds. For example:
- Tert-butyllithium can be used to prepare other organic lithium compounds such as aryl lithium, trialkyl borohydride, vinyl lithium, α-alkyl benzene sulfide, β-alkyl enamine, etc. through halogen-metal exchange reaction. It is used as a polymerization initiator and metallizing agent in the laboratory. Tert-butyllithium has stronger alkalinity and metallization activity and weaker nucleophilicity than n-butyllithium and isobutyl lithium, so it can be used for deprotonation lithiation of hydrocarbon substrates with weaker proton acidity. Generally, simple alkanes remain inert to tert-butyllithium, but react with tert-butyllithium in solvents containing heteroatoms such as THF. When the substrate is a compound containing heteroatoms such as oxygen, nitrogen, and sulfur, the use of tert-butyllithium as a deprotonation agent can achieve high regioselectivity. For example, the reaction of vinyl ether or cyclic ether with tert-butyllithium is a simple method for preparing α-lithiated vinyl ether.
- Tert-butyllithium is similar to other alkyl lithium reagents. It also has an ortho-lithiation effect on the lithiation reaction of aromatic compounds containing heteroatom substituents. In lithium-halide exchange reactions, tert-butyl lithium has greater advantages than n-butyllithium and isobutyl lithium due to its weaker nucleophilicity. Among them, the lithium-iodine exchange reaction is the most complete and effective. For example, it first reacts with 6-iodo-1-hexene at low temperature to undergo lithium-iodine exchange, and then the temperature is raised to undergo a highly stereoselective and regioselective 5-exocyclization reaction, which is then attacked by an electrophilic reagent to obtain a functionalized product. Similar isomerization reactions can also be used to prepare polycyclic compounds.
Applications of Tert-butyllithium
Tert-butyllithium can be used as an alkylation agent, debromination agent, organic synthesis, and important lithium reagent for carbonyl compounds. It can be used to prepare other organic lithium compounds such as aryl lithium, trialkyl borohydride, vinyl lithium, etc. through halogen-metal exchange reaction. It is also an initiator for polymerization reaction by reducing the alkyl group to the alkyl group under mild conditions. Compared with n-butyl lithium and isobutyl lithium, tert-butyllithium has stronger basicity and metalation activity and weaker nucleophilicity, so it can be used for deprotonation lithiation reaction of hydrocarbon substrates with weaker proton acidity.
Generally, simple alkanes can still remain inert to tert-butyllithium, but they will react with tert-butyllithium for heteroatom-containing solvents such as THF. When the substrate is a compound containing heteroatoms such as oxygen, nitrogen, and sulfur, the use of tert-butyllithium as a deprotonation agent can obtain high regioselectivity. Application examples are as follows:
- Used as a catalyst to prepare a 2-chloro-5-(trifluoromethyl)benzoic acid
Using parachlorotrifluorotoluene and tertiary amine compounds (such as tetramethylethylenediamine or N,N-diisopropylethylamine) as raw materials, 2-chloro-5-(trifluoromethyl)benzene lithium salt is formed under the action of strong base tert-butyl lithium, and the lithium salt reacts with solid carbon dioxide to obtain 2-chloro-5-(trifluoromethyl)benzoic acid. The reaction route has easy-to-obtain raw materials, high yield, simple process, simplified purification process, shortened production cycle, and is conducive to industrial production. - As a raw material for sealing materials
The sealing material, calculated by mass, includes the following components: 200-250 parts of silicone rubber, 250-300 parts of fluororesin, 100-150 parts of vulcanized rubber, 150-200 parts of EPDM rubber, 10-15 parts of sodium stearoyl lactylate, 10-12 parts of titanium dioxide, 5-8 parts of potassium hydroxide, 12-15 parts of magnesium hydroxide, 8-10 parts of acrylic anhydride, 6-8 parts of phenyl isocyanate, 10-15 parts of dimethyl fumarate, 5-8 parts of dibenzoyl peroxide, 6-8 parts of tert-butyl lithium, 7-8 parts of silicon nitride, and 5-10 parts of silicon powder. The sealing material has high mechanical strength, low friction coefficient (0.20-0.22), strong wear resistance, and long service life under high temperature (can work at 200°C) and high pressure (can withstand a pressure of 400MPa) working conditions.
The Correct Way to Use Tert-butyllithium
Organic metal reagents are commonly used reagents in laboratories. They can provide active intermediates such as carbon anions, free radicals and carbenes, such as Grignard reagents and organic lithium reagents. They are sensitive to air and water and are prone to spontaneous combustion. The most “famous” of them is tert-butyllithium (tert-Butyllithium). It is extremely alkaline and has a strong ability to extract hydrogen, but at the same time it can react violently and burn rapidly when it meets water and oxygen. If you are not careful, it can trigger a laboratory accident. It is one of the most dangerous reagents in the laboratory.
The recommended method here is to use positive pressure and negative pressure methods, but you must also take good protection. It is recommended that you use double needle transfer. Positive pressure method, insert the needle below the liquid level of tert-butyllithium, slowly pass inert gas such as N2 into the reagent bottle, slowly pressurize, and when the reagent in the constant pressure dropping funnel is about to reach the pre-marked scale, pull out the needle on the side of the reagent bottle (during this operation, the reactor cannot be sealed, remember, generally add an inert gas balloon). Negative pressure method, insert the needle below the liquid level of tert-butyllithium, seal the reactor and draw negative pressure, add an inert gas balloon to the tert-butyl lithium reagent bottle to balance the pressure.
Be cautious when using butyl lithium to avoid leakage. One more thing to say is that you should not treat n-butyl lithium and tert-butyl lithium the same. Tert-butyllithium is much more dangerous, so you really have to use it with caution. When it comes to butyl lithium reactions, make sure to stay away from water sources, organic reagents and flammable gases, and keep the table dry and tidy. Before operation, make sure that the entire system, including the reaction container, needle, double-ended needle hose, etc., is free of water and oxygen. When operating the experiment, wear anti-corrosion gloves, fireproof lab coats, goggles, and prepare fire blankets or sand nearby.
Product Data
1. Certificate Of Analysis (COA)
2. Material Safety Data Sheet (MSDS)
3. Route of synthesis (ROS)
4. Method of Aanlysis (MOA)
5. Nuclear Magnetic Resonance (NMR)
6. Packing pictures and loading video before loading
7. Free Sample
8. Factory audit
Tert-butyllithium Manufacturer & Supplier
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Loading and Transportation
1. ≤50kg, Express delivery recommended, usually called as DDU service;
2. ≤500kg, Air shipping recommended, usually called as FOB, CFR, or CIF service;
3. >500kg, sea shipping recommended, usually called as FOB, CFR, or CIF service;
4. For high value products, please select air shipping and express delivery for safe.
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Related References
- Sun Yu; Zhang Chuntao; Ji Fengyuan. A method for preparing 2-chloro-5-(trifluoromethyl)benzoic acid. CN201210525388.8
- WikiPedia