n-Butyl lithium

HCID 61028

Basic information

CAS
109-72-8
Standard SMILES
[CH2-]CCC.[Li+]
InChIKey
DLEDOFVPSDKWEF-UHFFFAOYSA-N
Molecular formula
C4H9Li
Average molar mass
64.1 g/mol

Overview

Butyllithium is an alkyllithium compound.

Names & identifiers

Preferred name
n-Butyl lithium
IUPAC
lithium butane
English name
n-Butyllithium
Molecular formula
C4H9Li
Molecular weight
64.06

Names & synonyms

lithium;butanen-Butyl lithiumC4H9LiLiBun-butyllitiumMFCD00009414BuLibutyilithiumbutyllitiumUNII-09W9A6B8ZCbutyl-lithiumn-butyllithiurn
Show more names
N-BULIBUTYLLITHIUMLithiumn-butylButyllithium solutionn-ButyllithiuM(BULI)ButyllithiuminhexaneMn-BuLi, Lithium-1-butaniden-Butyllithium, 1.6M solution in hexanesbutyl-lithiu
n-butyllithumn-Buyllithiumn- butyllithiumn-butyl-lithiumnButLi1-butyllithiumn-buty lithiumn-butyl lithum

Database identifiers

CAS
109-72-8
PubChem CID
61028
ChEBI
CHEBI:51469
UNII
09W9A6B8ZC
Nikkaji
J370K

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
5

Physicochemical properties

Melting point
-95 °C · -95 °C
Boiling point
80 °C · 80 °C
Density
0.68 g/mL · 0.68 g/mL at 20 °C
vapor pressure
163 hPa · 163 hPa ( 20 °C)
Flash point
10 °F · 10 °F
storage temp.
2 · 2-8°C

Safety & regulation

Hazard information

CSL Reaction Information · 6 items

CSL00127

Perfluorethyllithium + Phosphorus Trichloride,Phosphorus + N-BUTYLLITHIUM + CHLOROPENTAFLUOROETHANE

Avoid temperatures below -90 C

Substitution

Several times in our laboratory, we have experienced a violent decomposition of the ethereal C2F5Cl/n-BuLi solution after the addition of just a few drops of (R)nPCl3=n. In each of these cases, the metal-halogen exchange temperature was maintained below -90 C. We believe that this problem is due to a buildup of starting reagents at low temperatures.

C&EN

Safety data

F
3-10
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 3399 4.3/PG 1
hs_code
29319090

Chemistry & industry

Applications · 3 items

UsesN-Butyllithium solution is mostly used as a pharmaceutical intermediate to synthesize anionic polymerization initiator. It is also used to produce rubber (such as integral rubber SIBR, which is the most versatile diene rubber to date), fragrance, liquid crystal materials, and other industries. It is a chemical product intermediate, linking agent, alkylating agent, and polymerization catalyst. As a catalyst, N-Butyllithium is widely used as a pharmaceutical intermediate, liquid crystal monomer, and pesticide production catalyst. N-Butyllithium is also widely used in organic syntheses, especially in growing carbon chains, and it is a staple laboratory product in reactions such as: 1) Metallization reaction: R-H + n-Butyl-Li → R-Li + Butane, in which the produced lithium alkyl can react with many substances. 2) Direct metallization: the aromatic compound that connects the substitute reacts with N-Butyllithium, and lithium metal can be attached to the aromatic compound. 3) Nucleophilic addition and substitution reaction. 4) Halogen-metal replacement.

Usesn-Butyllithium is used as a polymerization initiator in the production of elastomers like polybutadiene and styrene- butadiene- styrene. As a strong base, it is utilized in the synthesis of organic compounds. It undergoes thermal decomposition to prepare 1-butene.

Usesn-Butyllithium is a strong nucleophile in the synthetic organic chemistry. It is also used as an initiator in the polymerization process.

Preparation methods · 1 item

PreparationIndustrially, 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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
商丘市华康众邦生物科技有限公司13011705167

Additional notes

DefinitionChEBI: Butyllithium is an alkyllithium compound.

Related reactions

205 records

Compound notes

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