109-72-8 Usage
Chemical Description
n-butyllithium is an organolithium compound, and indene is an organic compound with a bicyclic structure.
Description
n-Butyllithium is a colorless or slightly yellow transparent liquid at room temperature, also available in powder form. It is a strong nucleophile in synthetic organic chemistry and is commonly used as a polymerization initiator, pharmaceutical intermediate, linking agent, alkylating agent, and catalyst. Due to its high reactivity and extreme solubility, even in its impurities, it is often considered a viscous liquid. It is soluble in many organic solvents, forms complex compounds with ethers, amines, and sulfides, and uses N-hexane as a solvent. However, it is spontaneously combustible when in contact with water.
Uses
Used in Pharmaceutical Industry:
n-Butyllithium is used as a pharmaceutical intermediate for the synthesis of anionic polymerization initiators, liquid crystal monomers, and as a catalyst in pesticide production.
Used in Rubber Industry:
n-Butyllithium is used as a polymerization initiator in the production of elastomers like polybutadiene and styrene-butadiene-styrene, which are versatile diene rubbers.
Used in Organic Syntheses:
n-Butyllithium is widely used in organic syntheses, especially for growing carbon chains. It is a staple laboratory product in reactions such as metallization, direct metallization, nucleophilic addition and substitution, and halogen-metal replacement.
Used in Fragrance and Liquid Crystal Materials Industries:
n-Butyllithium is utilized in the production of fragrances and liquid crystal materials due to its properties as a chemical product intermediate and catalyst.
Used in Laboratory Research:
n-Butyllithium is a common reagent in laboratory research for its strong nucleophilic properties and its ability to initiate various chemical reactions.
Identifying Procedures
N-Butyllithium must be calibrated through single titration as follows:
1) Titration solution: 1mol/L SEC butanol/dimethylbenzene solution (butanol and dimethylbenzene must be dried with an activated 5A molecular sieve)
2) Indicator: 2,2’-dipyridine
3) Solvent: dimethylbenzene (must be dried with an activated 5A molecular sieve).
4) Operation method: Under the protection of argon, add magneton, 20ml dimethylbenzene and a small amount of indicator into a 100ml 3-lipped bottle with a tipping plug. Then use a precisely marked 2ml injector to swiftly transfer 2ml N-Butyllithium into the bottle (the air in the injector must be replaced with argon, which must then be expelled when collecting the N-Butyllithium; fill and drain the injector in the N-Butyllithium multiple times to prevent any water or air from remaining in the injector). The system should turn a purplish red. Then, wash, dry, and rinse the same injector with titration solution 2-3 times (to prevent any change in the amount added) and titrate the solution until the system turns yellow, and cease titration.
5) Repeat titration once; if the percent error between the two times is within 2%, the result can be regarded as correct.
6) Titration result: titration solution (ml)/2 to obtain N-Butyllithium concentration.
Warnings and precautions
1) N-Butyllithium is extremely combustible when in contact with air; when measuring, the needle of the injector will eject sparks.
2) The entire process must be protected by argon for safety precaution.
3) If N-Butyllithium catches fire, it must be extinguished with sand, which must be placed within arm’s reach at all times.
When preparing and using N-Butyllithium, do not operate alone in case of emergency
Explosivity characteristics
May explode in combination with phenylethylene
Flammability characertistics
Combusts in air at a concentration abover 20%; combusts upon contact with water and carbon dioxide; flammable when in contact with heat and open flame.
Storage
Store in ventilated, cool and dry spaces; must be waterproof and carbon dioxide-proof.
Extinguisher
Dry powder
Preparation
Industrially, n-butyllithium is produced by the
reaction of n-butyl chloride with lithium metal dispersion in various hydrocarbon solvents.
Hexane is the most commonly used solvent. Up to one-half of the lithium is replaced with
sodium in order to lower the cost of the butyllithium and increase the reactivity of the dispersion.
The reaction is carried out below the boiling point of the solvent.The laboratory procedure is essentially the same except that pentane and diethyl ether
are two of the more popular solvents. The preparation runs smoothly in ether at lower
temperatures but the product must either be used immediately or kept refrigerated due to
the rapid cleavage of ether by n-butyllithium.
Flammability and Explosibility
The risk of fire or explosion on exposure of butyllithium solutions to the atmosphere
depends on the identity of the organolithium compound, the nature of the solvent,
the concentration of the solution, and the humidity. t-Butyllithium solutions are the
most pyrophoric and may ignite spontaneously on exposure to air. Dilute solutions
(1.6 M, 15% or less) of n-butyllithium in hydrocarbon solvents, although highly
flammable, have a low degree of pyrophoricity and do not spontaneously ignite.
Under normal laboratory conditions (25 °C, relative humidity of 70% or less),
solutions of -20% concentration will usually not ignite spontaneously on exposure to
air. More concentrated solutions of n-butyllithium (50 to 80%) are most dangerous
and will immediately ignite on exposure to air. Contact with water or moist materials
can lead to fires and explosions, and the butyllithiums also react violently with
oxygen.
storage
In
particular, butyllithium should be stored and handled in areas free of ignition
sources, and containers of butyllithium should be stored under an inert atmosphere.
Work with butyllithium should be conducted in a fume hood under an inert gas such
as nitrogen or argon. Safety glasses, impermeable gloves, and a fire-retardant
laboratory coat are required.
Incompatibilities
The butyllithiums are extremely reactive organometallic compounds. Violent
explosions occur on contact with water with ignition of the solvent and of the butane
produced. t-Butyllithium will ignite spontaneously in air. The butyllithiums ignite on
contact with water, carbon dioxide, and halogenated hydrocarbons. The
butyllithiums are incompatible with acids, halogenated hydrocarbons, alcohols, and
many other classes of organic compounds.
Waste Disposal
Excess butyllithium solution can be destroyed by dilution with hydrocarbon solvent to a concentration of
approximately 5 wt %, followed by gradual addition to water with vigorous stirring under an inert
atmosphere. Alternatively, the butyllithium solution can be slowly poured (transfer by cannula for s- or tbutyllithium)
into a plastic tub or other container of powdered dry ice.
The residues from the above procedures and excess butyllithium should be placed in an appropriate
container, clearly labeled, and handled according to your institution's waste disposal guidelines.
Check Digit Verification of cas no
The CAS Registry Mumber 109-72-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 109-72:
(5*1)+(4*0)+(3*9)+(2*7)+(1*2)=48
48 % 10 = 8
So 109-72-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3
109-72-8Relevant articles and documents
-
Tomboulian,Stehower
, p. 1509 (1968)
-
Eberly
, p. 1309,1310 (1961)
Ultrasounds in Organic Syntheses. 1. Effect on the Formation of Lithium Organometallic Reagents
Luche, Jean-Louis,Damiano, Jean-Claude
, p. 7926 - 7927 (1980)
-
Gilman,Schwebke
, p. 4115,4116 (1961)
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