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
Show more names
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
- Formal charge
- 0
- Complexity
- 7.6
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
- solubility
- Miscible with diethyl ether and cyclohexane.
- form
- liquid
- color
- yellow
- Specific Gravity
- 0.695 · 0.695
- Odor
- Odor of the solvent
- explosive limit
- 1.2 · 1.2-7.8% (v/v)
- Water Solubility
- vigorous reaction
- Sensitive
- Air & Moisture Sensitive
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- BRN
- 1209227 · 1209227
- InChI
- 1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;
- InChIKey
- MZRVEZGGRBJDDB-UHFFFAOYSA-N
- SMILES
- [Li]CCCC
- LogP
- 1.25 · 1.25-2.31
- FDA 21 CFR
- 177.26 · 177.2600
- Indirect Additives used in Food Contact Substances
- BUTYLLITHIUM
- CAS DataBase Reference
- 109 · 109-72-8(CAS DataBase Reference)
- FDA UNII
- 9 W9A6B8ZC · 09W9A6B8ZC
- NIST Chemistry Reference
- Butyl lithium(109-72-8)
- EPA Substance Registry System
- Lithium, butyl- (109-72-8)
- UNSPSC Code
- 12352142 · 12352142
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 314 · H314-H361-H372-H336-H304-H411-H225-H250-H260
- Precautionary statements
- 501 · P501-P223-P273-P222-P270-P202-P240-P231+P232-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P335+P334-P391-P308+P313-P303+P361+P353-P302+P334-P301+P310-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P233-P422-P402+P404-P403+P235-P405
- target organs
- Central nervous system
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,C,N
- Risk Statements
- 14 · 14/15-17-34-48/20-51/53-62-65-67-63-35-11-15-50/53-66
- Safety Statements
- 6 · 6-9-16-26-36/37/39-45-61-62-6A-46-43B-43-60-33-29-5
- RIDADR
- 3399 · UN 3399 4.3/PG 1
- WGK Germany
- 3 · 3
- F
- 3 · 3-10
- Autoignition Temperature
- 240 °C · 240°C
- TSCA
- TSCA listed
- HazardClass
- 4.3 · 4.3
- PackingGroup
- I
- HS Code
- 29319090 · 29319090
- Storage Class
- 4.2 · 4.2 - Pyrophoric and self-heating hazardous materials
- Hazard Classifications
- 2 Asp · Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Pyr. Liq. 1Skin Corr. 1BSTOT SE 3Water-react 1
- Toxicity
- There is little toxicity data available for the butyllithiums; for data on ether and hydrocarbon solvents, see the appropriate LCSSs.
- REACH Registrations
- Active
- Excepted Quantities
- Forbidden
Safety & regulation
Hazard information
CSL Reaction Information
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
- Toxicity
- There is little toxicity data available for the butyllithiums; for data on ether and hydrocarbon solvents, see the appropriate LCSSs.
- risk_code
- 14/15-17-34-48/20-51/53-62-65-67-63-35-11-15-50/53-66
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS08,GHS09
- hazard_code
- F,C,N
- safety_code
- 6-9-16-26-36/37/39-45-61-62-6A-46-43B-43-60-33-29-5
- hazard_class
- 4.3
- Storage Class
- 4.2 - Pyrophoric and self-heating hazardous materials
- packing_group
- I
- target organs
- Central nervous system
- Hazard statements
- H314-H361-H372-H336-H304-H411-H225-H250-H260
- Excepted Quantities
- Forbidden
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Pyr. Liq. 1Skin Corr. 1BSTOT SE 3Water-react 1
- Autoignition Temperature
- 240°C
- Precautionary statements
- P501-P223-P273-P222-P270-P202-P240-P231+P232-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P335+P334-P391-P308+P313-P303+P361+P353-P302+P334-P301+P310-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P233-P422-P402+P404-P403+P235-P405
Chemistry & industry
Applications
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Butyllithium is an alkyllithium compound.
Related reactions
Compound notes
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