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n-Butyllithium
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Name

n-Butyllithium

 EINECS 203-698-7
CAS No. 109-72-8 Density 0.68 g/mL at 20 °C
PSA 0.00000 LogP 1.75410
Solubility vigorous reaction Melting Point -95 °C
Formula C4H9Li Boiling Point 80 °C
Molecular Weight 64.0565 Flash Point 10 °F
Transport Information UN 3399 4.3/PG 1 Appearance clear yellow solution
Safety 6-9-16-26-36/37/39-45-61-62-6A-46-43B-43-60-33-29-5 Risk Codes 14/15-17-34-48/20-51/53-62-65-67-63-35-11-15-50/53-66
Molecular Structure Molecular Structure of 109-72-8 (n-Butyllithium) Hazard Symbols FlammableF,CorrosiveC
Synonyms

1-Butyllithium;Butyllithium;n-Butyllithium in Hexanes (15%soln & 23%soln);

Article Data 69

n-Butyllithium Synthetic route

109-72-8

n-butyllithium

C5H4FeC5H3(CH(CH3)CH2CH(C5H5))(C(H)C12H8)

C5H4FeC5H3(CH(CH3)CH2CH(C5H4))(CC12H8)(2-)*2Li(1+)=C5H4FeC5H3(CHCH3CH2CHC5H4Li)(CLiC12H8)

Conditions
ConditionsYield
In toluene; pentane (Ar); 1.6 M n-BuLi in pentane was added at 0°C to soln. of ferrocene in toluene, stirred for 6 h at room temp.; filtered, washed with pentane, dried in vac., elem. anal.;93%
109-72-8

n-butyllithium

384378-22-7

(CH3)2Ge(C5(CH3)4H)(C5H5)

2Li(1+)*(CH3)2Ge(C5(CH3)4)(C5H4)(2-)=Li2[(CH3)2Ge(C5(CH3)4)(C5H4)]

Conditions
ConditionsYield
In diethyl ether under N2, Schlenk technique; mixing at -78°C (BuLi in hexane), mixt. was warmed to room temp. and stirred for 15 h; solvent was removed, ppt. was washed with hexane, dried under vac.; elem. anal.;92%
109-72-8

n-butyllithium

13292-87-0

dimethyl sulfide borane

A

lithium borohydride

B

82111-98-6

lithium [butyl(trihydrido)borate]

C

67335-72-2

LiHB(s-Bu)3

Conditions
ConditionsYield
In tetrahydrofuran; hexane; dichloromethane under dry N2, hexane soln. of BuLi cooled to -20°C, H3B-SMe2 added to vigorously stirred soln. within 60 min, 2 hours later all volatiles removed in vac.; material suspended in hexane, THF added to form soln., solvents removed, oily material dissolved in CH2Cl2, pentane added to separate LiBH4, repetition of procedure gave slightly purer product;A n/a
B 91%
C n/a
109-72-8

n-butyllithium

134939-44-9

bis(tetramethylcyclopentadienyl)dimethylgermanium

2Li(1+)*(CH3)2Ge(C5(CH3)4)2(2-)=Li2[(CH3)2Ge(C5(CH3)4)2]

Conditions
ConditionsYield
In diethyl ether under N2, Schlenk technique; mixing at -78°C (BuLi in hexane), mixt. was warmed to room temp. and stirred for 15 h; solvent was removed, ppt. was washed with hexane, dried under vac.; elem. anal.;91%
109-72-8

n-butyllithium

110-18-9

N,N,N,N,-tetramethylethylenediamine

1231953-83-5

trimethylamine borane

A

lithium borohydride

B

Li(tetramethylethylenediamine)BH3(benzyl)

Conditions
ConditionsYield
In hexane; toluene byproducts: (CH3)3N; under dry N2, hexane soln. of n-BuLi added to soln. of TMEDA in toluene, after 30 min added H3B-NMe3, heated for 1 h to reflux, soln. kept for 3 d at -25°C; elem. anal.;A 10%
B 90%
109-72-8

n-butyllithium

478038-85-6

(CH3)2Ge(C5(CH3)4H)(C5H4CH3)

2Li(1+)*(CH3)2Ge(C5(CH3)4)(C5H3CH3)(2-)=Li2[(CH3)2Ge(C5(CH3)4)(C5H3CH3)]

Conditions
ConditionsYield
In diethyl ether under N2, Schlenk technique; mixing at -78°C (BuLi in hexane), mixt. was warmed to room temp. and stirred for 15 h; solvent was removed, ppt. was washed with hexane, dried under vac.; elem. anal.;90%
7446-70-0

aluminium trichloride

109-72-8

n-butyllithium

443890-22-0

N-(2,6-bis(isopropyl)phenyl)-5-tert-butylpyrrolylaldimine

443890-21-9

[N-(2,6-bis(isopropyl)phenyl)-5-tert-butylpyrrolylaldiminato]aluminium(III) dichloride

Conditions
ConditionsYield
In toluene under N2, Schlenk techques; n-BuLi was added to the soln. of ligand at -35°C, mixt. was warmed to room temp., stirred for 2 h, soln. was cooled to -35°C again and added to suspn. of AlCl3 with stirring,mixt. stirred at room temp. for 36 h; mixt. was filtered, washed with toluene, filtrate was concd., cooled to -35°C; elem. anal.;88%
109-72-8

n-butyllithium

13292-87-0

dimethyl sulfide borane

A

lithium borohydride

B

82111-98-6

lithium [butyl(trihydrido)borate]

C

n-butylborane-dimethyl sulfide

D

15243-31-9

Li{B(n-C4H9)4}

Conditions
ConditionsYield
In tetrahydrofuran; hexane under dry N2, hexane soln. of n-BuLi cooled to -20°C, H3B-SMe2 added to vigorously stirred soln. within 4 h, resulting suspn. stirred overnight; filtered, detected by NMR;A 13%
B 87%
C n/a
D n/a
In hexane; dichloromethane; pentane under dry N2, hexane soln. of BuLi cooled to -20°C, H3B*SMe2 added to vigorously stirred soln. within 4 h, stirred overnight, solid filtered, solvent from filtrate removed; residue treated with 1:1 mixt. of CH2Cl2 and pentane, not isolated, detected in CH2Cl2-rich phase by NMR;
...Expand
109-72-8

n-butyllithium

519005-12-0, 439099-43-1

buta-1,3-dien-2-yltin trichloride

2244-38-4

buta-1,3-dien-2-yl-tributylstannane

Conditions
ConditionsYield
In not given86%
109-72-8

n-butyllithium

16390-61-7

1-phenyl-1,2-closo-C2B10H11

109-94-4

formic acid ethyl ester

16450-20-7

1-(CH(o-CB10H10CC6H5)OH)-2-(C6H5)-1.2-C2B10H10

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; benzene nitrogen atmosphere; ether soln. of formate addn. at 50 to 60°C to benzene soln. of Li-salt of carborane (obtained from carborane and BuLi), stirring (1 h), treating with aq. HCl, extracting with ether; extract drying over MgSO4 and evapn., residue recrystn. (hexane);85%

n-Butyllithium Chemical Properties

Empirical Formula: C4H9Li
Molecular Weight: 64.0553
Flashing point: 10 °F
Density: 0.68 g/mL at 20 °C
Boiling Point: 80 °C
Melting point: -95 °C
Storage tempreture: 2-8 °C
Water solubility: Vigorous reaction
Sensitive: Air & moisture sensitive
Appearance: Clear yellow solution
Structure of n-Butyllithium (CAS NO.109-72-8):
                       
IUPAC Name: Lithium butane
Canonical SMILES: [Li+].CCC[CH2-]
InChI: InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/q-1;+1
InChIKey: DLEDOFVPSDKWEF-UHFFFAOYSA-N
Product Category of n-Butyllithium (CAS NO.109-72-8): Organometallics;Alkyl Metals;Grignard Reagents & Alkyl Metals;Li (Lithium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds

n-Butyllithium Uses

 n-Butyllithium (CAS NO.109-72-8) is principally valued as a catalyst for the industrial polymerization of dienes, such as butadiene: C4H9Li + CH2=CH-CH=CH2 → C4H9-CH2-CH=CH-CH2Li  .
Isoprene can be polymerized stereospecifically in this way. Also of commercially importance is the use of butyllithium for the production of styrene-butadiene polymers. Even ethylene will insert into BuLi.

n-Butyllithium Production

The standard preparation for n-BuLi is reaction of bromobutane or chlorobutane with Li metal:
2 Li + C4H9X → C4H9Li + LiX
where X = Cl, Br

n-Butyllithium Safety Profile

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.

n-Butyllithium 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.

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