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Lithium triisobutylhydroborate, also known as lithium tri sec butyl borohydride, is an organic metal compound that typically appears as a colorless to pale yellow liquid, miscible with tetrahydrofuran, and sensitive to moisture. It is used as a reducing agent in organic synthesis, especially in the fields of pharmaceuticals, fragrances, pesticides, dyes, and fine organic synthesis. It is a representative of the Selectride family, with the advantages of good solubility and lower price, making it more widely used and also suitable for industrial production. Therefore, the storage container should be kept sealed, stored in a cool, dry place, and ensure good ventilation or exhaust devices in the workspace. Due to its sensitivity to moisture, contact with moisture should be avoided.

Additional information of chemical compound:
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Chemical Formula |
C12H28BLi |
|
Exact Mass |
190.24 |
|
Molecular Weight |
190.11 |
|
m/z |
190.24(100.0%),189.25(24.8%),191.25(9.7%),189.24(8.2%), 191.25 (3.2%), 190.25 (3.2%), 188.25 (2.0%) |
|
Elemental Analysis |
C, 75.82; H, 14.85; B, 5.69; Li, 3.65 |
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Lithium triisobutylhydroborate, with its huge steric hindrance constructed by three sec butyl groups and precise metering characteristics of a single negative hydrogen ion, has opened up an exclusive pathway in the chemical industry for "reducing only the reduced bond".
Organic synthesis:
This is the most core and irreplaceable usage map, covering almost all high-end scenarios of fine chemical synthesis.
1. Non enantioselective reduction of ketons
This is its signature move. The huge steric hindrance of the three sec butyl groups allows them to preferentially attack the ketone groups with smaller steric hindrance, while turning a blind eye to functioal groups such as cyanide, ketal, aldehyde, and silicon ether. When there is a chiral group in the ortho position of a ketone, the reduction reaction has extremely high stereoselectivity - it can accurately generate only one mirror isomer.
In steroid hormone synthesis, it can selectively reduce specific ketone groups to hydroxyl groups, completely avoiding side reactions.
2. 1,4-Conjugated Addition Reduction of α, β - Unsaturated Ketons
For ketide substrates, 1,4-conjugated addition reduction can be achieved to generate ketons or alcohols. More intricately, the ketone group in the linear substrate is selectively reduced to alcohol, while the double bond in the cyclic substrate is preferentially reduced. When isolated ketons coexist with α, β - unsaturated ketons in the same molecule, a limited amount of reagents can be used to reduce only isolated ketons while leaving unsaturated ketons "unscathed".
3. Low temperature conjugated carbonyl reduction
Many reduction reactions require high-temperature driving, but maintain high activity even at extremely low temperatures of -78 ℃. This is crucial for the synthesis of thermosensitive molecules - it can effectively reduce conjugated carbonyl compounds in ice water baths or even lower temperatures without damaging other fragile functioal groups in the molecule.
4. Reduction of ester groups to hemiacetals
With appropriate dosage and conditions, ester groups can be reduced to hemiacetals.
Under these reaction conditions, the azide functioal group can surprisingly remain unaffected - this "selectivity" can be considered a textbook level operation in synthetic chemistry.
5. Selective reduction of acrylonitrile derivatives outside the ring
Selective reduction of conjugated double bonds and iodides of acrylonitrile derivatives outside the ring provides a unique tool for fine regulation of complex molecules containing cyanide and iodine groups.
6. Reduction of haloalkanes
Lithium triisobutylhydroborate can be used for reducing halogenated alkanes and provides an irreplaceable selective pathway in multi-step synthesis that requires the retention of other functioal groups.

Medical synthesis:
The position in drug synthesis can be called a "behind the scenes hero", directly related to the production of multiple heavyweight drugs.
1. Synthesis of Intermediate for Anticancer Drug Paclitaxel
In the key intermediate synthesis of anticancer drug paclitaxel, the ketone reduction reaction used in the core step has a yield of over 95%. This high yield implies significant cost advantages and procedure stability in multi-step synthesis.
2. Synthesis of antidepressant paroxetine
Paroxetine is one of the best-selling SSRI antidepressants worldwide. In its synthesis, high stereoselectivity is utilized to achieve asymmetric reduction by binding with chiral ligands.
Efficiently synthesizing a single configuration of active product - the two mirror isomers of the drug may have vastly different physiological activities, while ensuring only the "right one" is generated.
3. Total synthesis of Overnman alkaloids
In the classic total synthesis of Overnman alkaloids, ketone reduction is one of the key steps, fully demonstrating its indispensable role in the synthesis of complex natural products.
4. Opioid Drug Chemistry
In the deprotection reaction of N-methoxycarbonyl opioid like substances replacing N-non opioid substances, it plays a special role as a de symmetric reagent, and this application is directly related to the development and production of analgesic drugs.
5. Pharmaceutical intermediates and high value-added chemicals
In broader pharmaceutical research and development, participate in the construction of various drug molecules to reduce carbonyl groups in drug molecules, thereby improving the biological activity and stability of drugs. Cangzhou Lingang Xingchen Chemical and other enterprises have supplied it to major pharmaceutical companies, providing customized synthesis services from gram to ton levels.
Spice Industry:
L-Selectride also shines brightly in the spice industry. The key component of rose aroma, citronellol, is prepared through its selective reduction of precursors. Due to its precise recognition ability of functioal groups, it can achieve target reduction without damaging other sensitive groups in spice molecules, which is crucial for controlling the quality of spices. The perfumers use it more in the preparation of "sea brand" (ocean, coast, sea breeze, etc.) essence and other "modern" fantasy essence. The famous brand perfume emerging in the past decade is more or less full of flavor.
Materials Science:
1. High performance composite stuff
By compounding with stuff such as metal oxides and carbon nanotubes, composite stuff with excellent performance in conductivity, mechanical strength, and thermal stability can be prepared. These stuff can be used to prepare high-performance battery electrode stuff and aerospace stuff.
2. Positive electrode stuff for lithium-ion batteries
It can be used as an additive in the preparation of positive electrode stuff for lithium-ion batteries, improving the electrochemical performance and stability of the stuff, and directly enhancing the charging and discharging efficiency of the battery.
3. Semiconductor thin film growth
In chemical vapor deposition (CVD) or physical vapor deposition (PVD) procedures, it can be used as a pre-treatment agent on the substrate surface to remove surface oxides and impurities, promoting the growth of high-quality thin films. At the same time, it can also serve as a chemical precursor, providing metal boron atoms for depositing boride thin films (such as silicon boride SiB ₓ).
4. Integrated circuit manufacturing
In integrated circuit manufacturing, it can serve as a reagent in certain procedures, participate in specific chemical reactions, or improve the preparation procedure.
At the same time, it can also be used as an impurity treatment agent to remove impurity elements such as oxygen, water vapor, and nitrogen, improving the purity and performance of semiconductor stuffs.
5. Synthesis of Liquid Crystal Molecules
In the synthesis of liquid crystal molecules, precise control of the degree of reduction of functioal groups directly determines stuff properties, and is the key tool to achieve such precise control.
6. Internal stress regulation
In the manufacturing procedure of semiconductor devices, it can be used to control and regulate the internal stress of crystals, which is crucial for the integrity of crystals and device performance.
In the field of new energy
1. Solar cells
In the preparation of solar cell stuffs, lithium triisobutylhydroborate can be used to regulate the band structure and photoelectric properties of the stuffs, thereby improving the photoelectric conversion efficiency.
2. Electrolyte for lithium-ion batteries
L-Selectride can be used as an additive in lithium-ion electrolytes to improve the conductivity and ion migration rate of the electrolyte, thereby enhancing the battery's charge and discharge performance and cycle life.

3. Research on hydrogen storage stuffs
Due to its high hydrogen capacity, it is often blended or compounded with metal hydrides for research and development of high-capacity hydrogen storage stuffs, which has strategic significance for the future of hydrogen energy economy.
4. Fuel cells and supercapacitors
In new energy devices such as fuel cells and supercapacitors, significant application potential has also been demonstrated.
Pesticides and Fine Chemicals:
In the field of pesticides, it helps to synthesize pesticide active ingredients with efficient insecticidal and herbicidal functions. In the field of fine chemicals, it is widely used for the selective reduction of multifuntional molecules and is an indispensable reagent in the production of high value-added chemicals. The products of Cangzhou Lingang Xingchen Chemical and other enterprises have been widely used in major pesticide enterprises, chemical enterprises, and dye enterprises.
Catalyst and Hydrogen Source:
1. Catalytic reaction
Can catalyze carbene production reactions and carbonyl compound addition reactions; Used as a reduction catalyst for unsaturated compounds to promote the progress of reactions.
2. Laboratory hydrogen source
It can be used as a hydrogen source in the laboratory to provide the required hydrogen gas for reactions such as reduction and dehydrogenation.
3. Synthesis of deuterated compounds
Deuterated analogues can be prepared for isotope labeling studies, providing key tools for drug metabolism research and reaction mechanism exploration.
Tobacco and Electroplating:
1. Tobacco industry
In tobacco proceduring, it is used to modulate special aromas and enhance the sensory quality of tobacco products.
2. Electroplating brightener
It can be used as a brightener in electroplating procedure to improve the glossiness and uniformity of metal coatings, and has certain applications in electronic component manufacturing.
Asymmetric racemization reaction:
In the reactions of diesters, dehalogenated monocyclic pyrimidines, rearranged 5-trimethylsilyltripain, and deprotected N-methyloxycarbonyl substituted opioid like substances, it is an efficient asymmetric racemic reagent. It can accurately convert racemic compounds into chiral products of a single configuration - which is highly valuable in chiral drug synthesis, as a pair of mirror isomers often mean the world difference between "good medicine" and "poison".
From anti-cancer drugs to rose perfume, from lithium batteries to semiconductor chips, from hydrogen storage stuffs to pesticide synthesis, from chiral catalysts to hydrogen sources, lithium triisobutylhydroborate is used in nine fields, and is truly the "king of cross-border". Its value lies not in its ability to 'restore' something, but in its ability to selectively restore something. When there may be more than a dozen reducible functioal groups on a molecule, it can act like an experienced surgeon, precisely "cutting" only at the target location - this is the irreplaceable use magic bestowed upon it by steric hindrance.
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