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Home> Encyclopedia >   /  Catalysts  /  Pharmaceutical Intermediates  /  Organic Intermediate
n-Butyllithium structure
n-Butyllithium structure

n-Butyllithium

Iupac Name:lithium;butane
CAS No.: 109-72-8
Molecular Weight:64.056
Modify Date.: 2022-11-29 12:21
Introduction: N-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. View more+
1. Names and Identifiers
1.1 Name
n-Butyllithium
1.2 Synonyms

1-Butyllithium butyl-lithiu Butyllithium Butyllithium solution ButyllithiuminhexaneM Lithium, butyl- LITHIUM-1-BUTANIDE LITHIUMBUTYL Lithiumn-butyl N-BULI N-BUTYLLITHIUM

1.3 CAS No.
109-72-8
1.4 CID
61028
1.5 EINECS(EC#)
203-698-7
1.6 Molecular Formula
C4H9Li (isomer)
1.7 Inchi
InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/q-1;+1
1.8 InChkey
DLEDOFVPSDKWEF-UHFFFAOYSA-N
1.9 Canonical Smiles
[Li+].CCC[CH2-]
1.10 Isomers Smiles
[Li+].CCC[CH2-]
2. Properties
3.1 Density
0.68 g/mL at 20 °C
3.1 Melting point
80 °C
3.1 Boiling point
80 °C
3.1 Flash Point
10 °F
3.1 Precise Quality
64.08640
3.1 PSA
0.00000
3.1 logP
1.75410
3.1 Solubility
Miscible with diethyl ether and cyclohexane.
3.2 Appearance
Liquid
3.3 Storage
Store in ventilated, cool and dry spaces; must be waterproof and carbon dioxide-proof.
3.4 Color/Form
yellow
3.5 Odor
Odor of the solvent
3.6 Water Solubility
H2O: vigorous reaction
3.7 Stability
Stable under normal temperatures and pressures.
3.8 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 158 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 47 of 158 companies. For more detailed information, please visit ECHA C&L website

Of the 8 notification(s) provided by 111 of 158 companies with hazard statement code(s):

H250 (100%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids; Pyrophoric solids]
H260 (70.27%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances And Mixtures Which, In Contact With Water, Emit Flammable Gases]
H302 (31.53%): Harmful if swallowed [Warning Acute toxicity, oral]
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H317 (31.53%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (31.53%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P210, P222, P223, P231+P232, P260, P261, P264, P270, P272, P280, P301+P312, P301+P330+P331, P302+P334, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P335+P334, P363, P370+P378, P402+P404, P405, P422, and P501
4.2 Usage
N-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.
4.3 Waste Disposal
Excess butyllithium solution can be destroyed by dilution with hydrocarbon solvent to a concentration ofapproximately 5 wt %, followed by gradual addition to water with vigorous stirring under an inertatmosphere. 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 appropriatecontainer, clearly labeled, and handled according to your institution's waste disposal guidelines. n-Butyllithium Preparation Products And Raw materials Preparation Products
4. Safety and Handling
5.1 Hazard Codes
F; C
5.1 Risk Statements
R11;R14/15;R17;R35;R48/20;R63;R65;R67
5.1 Safety Statements
S16;S26;S36/37/39;S43;S45;S46;S62;S6
5.1 Packing Group
I
5.1 Hazard Class
4.3
5.1 Hazard Declaration
H225-H250-H261-H304-H314-H336-H410
5.1 RIDADR
UN 2445
5.1 Caution Statement
P210-P222-P231 + P232-P261-P273-P422
5.1 Incompatibilities
The butyllithiums are extremely reactive organometallic compounds. Violentexplosions occur on contact with water with ignition of the solvent and of the butaneproduced. t-Butyllithium will ignite spontaneously in air. The butyllithiums ignite oncontact with water, carbon dioxide, and halogenated hydrocarbons. Thebutyllithiums are incompatible with acids, halogenated hydrocarbons, alcohols, andmany other classes of organic compounds.
5.2 WGK Germany
3
5.2 Safety

S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. Probably very toxic. Solutions of greater than 20% will ignite spontaneously in air. Ignites on contact with water or CO2. May cause potentially explosive polymerization of styrene. Extremely flammable. To fight fire, use dry chemical; see special instructions of manufacturer. See also LITHIUM COMPOUNDS and BUTYLLITHIUM.
Hazard Codes:?FlammableF,CorrosiveC,DangerousN
Risk Statements: 14/15-17-34-48/20-51/53-62-65-67-63-35-11-15-50/53-66
R11:Highly flammable.?
R14 :Reacts violently with water.?
R15:Contact with water liberates extremely flammable gases.?
R17:Spontaneously flammable in air.?
R20:Harmful by inhalation.?
R35:Causes severe burns.?
R48:Danger of serious damage to health by prolonged exposure.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R62:Risk of impaired fertility.?
R65:Harmful: may cause lung damage if swallowed.?
R67:Vapours may cause drowsiness and dizziness.?
R66:Repeated exposure may cause skin dryness or cracking.?
Safety Statements: 6-9-16-26-36/37/39-45-61-62-6A-46-43B-43-60-33-29-5
S9:Keep container in a well-ventilated place.?
S16:Keep away from sources of ignition.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S33:Take precautionary measures against static discharges.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S43:In case of fire use ... (there follows the type of fire-fighting equipment to be used.)?
S46:If swallowed, seek medical advice immediately and show this container or label.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S62:If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.

5.3 Sensitive
Air & Moisture Sensitive
5.4 Specification

?n-Butyllithium , its cas register number is 109-72-8. It also can be called Lithium, butyl- ; and Butyllithium . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product:?Do not induce vomiting. Get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, n-Butyllithium (CAS NO.109-72-8)?is air sensitive, moisture sensitive, and?light sensitive, and reacts violently with water. It?contacts with water liberates highly flammable gases., acids, alcohols, carbon dioxide, oxygen, hydrogen, organic halides, and you must not take it with incompatible materials, ignition sources, exposure to air, exposure to moist air or water, direct sunlight..? And also prevent it to broken down into hazardous decomposition products:?Carbon monoxide, carbon dioxide, butane, lithium oxide.

5.5 Toxicity
There is little toxicity data available for thebutyllithiums; for data on ether and hydrocarbonsolvents, see the appropriate LCSSs.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Pyrophoric liquids, Category 1

Substances and mixtures, which in contact with water, emit flammable gases, Category 1

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H250 Catches fire spontaneously if exposed to air

H260 In contact with water releases flammable gases which may ignite spontaneously

H314 Causes severe skin burns and eye damage

Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P222 Do not allow contact with air.

P231+P232 Handle and store contents under inert gas/.... Protect from moisture.

P233 Keep container tightly closed.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P223 Do not allow contact with water.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P264 Wash ... thoroughly after handling.

Response

P302+P334 IF ON SKIN: Immerse in cool water [or wrap in wet bandages].

P370+P378 In case of fire: Use ... to extinguish.

P302+P335+P334 IF ON SKIN: Brush off loose particles from skin. Immerse in cool water [or wrap in wet bandages].

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/…

P321 Specific treatment (see ... on this label).

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Storage

P402+P404 Store in a dry place. Store in a closed container.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Usage
N-butyl lithium solution is mainly used for pharmaceutical intermediates of organic synthesis of anionic polymerization initiator and also used in synthetic rubber, essence and liquid. Commercial importance is the use of butyl lithium for the production of styrene-butadiene polymers.
8.1 Usage
n-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.
8.2 Fire Hazards
Flammable - 4th degree, Reactive - 2nd degree
8.3 Mesh Entry Terms
bu-Li|n-BuLi
8.4 Manufacturing Info
All other basic organic chemical manufacturing|Lithium, butyl-: ACTIVE
8.5 Use Classification
Fire Hazards -> Flammable - 4th degree, Reactive - 2nd degree
9. Computational chemical data
  • Molecular Weight: 64.056g/mol
  • Molecular Formula: C4H9Li
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 64.08642872
  • Monoisotopic Mass: 64.08642872
  • Complexity: 7.6
  • Rotatable Bond Count: 1
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Topological Polar Surface Area: 0
  • Heavy Atom Count: 5
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 2
  • CACTVS Substructure Key Fingerprint: AAADcchgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGAAAAAAACACAAAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
  • Description n-Butyllithium (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organi...
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