n-Butyllithium supplier | CasNO.109-72-8

Name
n-Butyllithium
EINECS 203-698-7
CAS No. 109-72-8
Article Data69
CAS DataBase
Density 0.68 g/mL at 20 °C
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
Hazard Symbols F,C
Synonyms 1-Butyllithium;Butyllithium;n-Butyllithium in Hexanes (15%soln & 23%soln);
PSA 0.00000
LogP 1.75410

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
In not given	86%

: 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

Conditions	Yield
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%

...Expand

: 109-72-8
n-butyllithium

: 60-29-7
diethyl ether

: 443890-22-0
N-(2,6-bis(isopropyl)phenyl)-5-tert-butylpyrrolylaldimine

: 13499-05-3
hafnium tetrachloride

: 610270-20-7
[Hf(5-tert-butyl-2-[(2,6-diisopropylphenyl)aldimino]pyrrolyl)Cl2(μ-Cl)2Li(OEt2)2]

Conditions

Conditions	Yield
In diethyl ether 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 HfCl4 with stirring,mixt. stirred at room temp. for 20 h; mixt. was filtered, washed with Et2O, ether filtrate was concd., cooled to -35°C; elem. anal.;	85%

...Expand

: 109-72-8
n-butyllithium

: 4181-91-3
(R)-(-)-benzyl-α-d chloride

: 688-73-3
tri-n-butyl-tin hydride

: 108-18-9
diisopropylamine

: 84369-11-9
(S)-(-)-(.alfa.-deuteriobenzyl)tributyltin

Conditions

Conditions	Yield
In tetrahydrofuran; hexane to THF soln. of (i-Pr)2NH at 0°C added hexane soln. of BuLi, stirred at 0°C for 30 min, Bu3SnH added, stirred at 0°C for 30 min, soln. added to THF soln. of (R)-PhCHDCl at 0°C over 30 min, mixt. kept at 0°C for 5 h; added water, mixt. extd. with ether, sepd., washed with water and brine, extract dried with MgSO4, concd., chromd.;	84%

...Expand

: 109-72-8
n-butyllithium

: 1231953-83-5
trimethylamine borane

A: lithium borohydride

B: 82111-98-6
lithium [butyl(trihydrido)borate]

C: 84280-42-2
lithium [(dimethylamino)methyl]trihydroborate

D: 84280-43-3
lithium benzyltrihydroborate

Conditions

Conditions	Yield
In hexane; toluene under dry N2, refluxing for 30 min;	A 4% B 80% C 4% D 2%
In hexane; toluene under dry N2, refluxing for 2 d;	A 15% B 64% C 15% D 6%

...Expand

: 109-72-8
n-butyllithium

: borane tetrahydrofuran

A: lithium borohydride

B: 84280-32-0
lithium di-n-butylborohydride

C: 67335-72-2
LiHB(s-Bu)3

D: 15243-31-9
Li{B(n-C4H9)4}

Conditions

Conditions	Yield
In tetrahydrofuran; hexane under dry N2, soln. of BH3 in THF cooled to -78°C, hexane soln. of n-BuLi added with stirring, mixt. allowed to warm to -30°C within 1 h; not isolated, detected by NMR;	A 77% B 3% C 13% D 7%

...Expand

: 109-72-8
n-butyllithium

: 13292-87-0
dimethyl sulfide borane

A: lithium borohydride

B: 82111-98-6
lithium [butyl(trihydrido)borate]

C: 15243-31-9
Li{B(n-C4H9)4}

Conditions

Conditions	Yield
In hexane under dry N2, hexane soln. of n-BuLi cooled to -10°C, H3B-SMe2 added with stirring for few minutes, after 20 min all volatile material stripped in vac.; residue dissolved in THF, not isolated, detected by NMR;	A 18% B 77% C 5%
In hexane under dry N2, hexane soln. of n-BuLi added over period of 10 min to H3B-SMe2 with stirring; residue dissolved in minimum THF, not isolated, detected by NMR;	A 44% B 41% C 15%

...Expand

: 109-72-8
n-butyllithium

: (2S, 5R, 7S, 8R, 2E, 4E)-tricarbonyliron[(η4-2-5)-8-(tert-butoxycarbonylamino)-7-methoxynona-2,4-dienal]

: 21406-61-1
pentyltriphenylphosphonium bromide

: (2R, 3S, 5R, 8S, 5E, 7E, 9Z)-tricarbonyliron[(η4-5-8)-2-(tert-butoxycarbonylamino)-3-methoxytetradodeca-5,7,9-triene]

Conditions

Conditions	Yield
In hexane; toluene (N2 atmosphere); addn. of BuLi to susp. of C5H11PPh3Br (stirring, 0°C), addn. of soln. of Fe complex (after 5 min, -78°C), stirring (-78°C, 30 min, 0°C, 30 min), addn. of H2O (0°C),extraction (EtOAc), drying (MgSO4); evapn. (in vacuo), chromatography (SiO2 hexane/EtOAc);	73%

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: 109-72-8
n-butyllithium

C20H8N4(BCl)2(C6H4CH3)4*(n)C6H5CH3 n:0.5-1;: C20H8N4(BCl)2(C6H4CH3)4*(n)C6H5CH3 n:0.5-1;

: anti-C20H8N4(BC4H9)2(C6H4CH3)4

Conditions

Conditions	Yield
In hexane byproducts: LiCl, toluene; C4H9Li soln. added to suspn. of C20H8N4(BCl)2(C6H5CH3)4*(n)C6H5CH3 in hexane (-78 °C), warmed up to room temp., stirred (16 h); ppt. filtered, washed with hexane, extd. with CH2Cl2; detd. by MAS, UV, (1)H NMR, (11)B NMR;	71%

: iron(II) chloride tetrahydrate

: 109-72-8
n-butyllithium

: 100-44-7
benzyl chloride

: 17534-15-5
1,2-benzenedithiole

: 116089-38-4
2-(Benzylthio)thiophenol

Conditions

Conditions	Yield
With hydrogenchloride; carbon monoxide In tetrahydrofuran under N2; reaction of dithiol and BuLi at -78 °C; addn. of Fe-salt at room temp.; CO introduced for 2h; benzyl chloride added; stirring for 1h at room temp.; evapn.; excess of benzyl chloride removed by hexane; HCl and THF added; refluxed for 2h;; evapn.; treatment with H2O/CCl4; organic layer dried (Na2SO4), filtered and evapd.; distn. (180-220 °C, vacuum); elem. anal.;;	70%

Yield

With hydrogenchloride; carbon monoxide In tetrahydrofuran under N2; reaction of dithiol and BuLi at -78 °C; addn. of Fe-salt at room temp.; CO introduced for 2h; benzyl chloride added; stirring for 1h at room temp.; evapn.; excess of benzyl chloride removed by hexane; HCl and THF added; refluxed for 2h;; evapn.; treatment with H2O/CCl4; organic layer dried (Na2SO4), filtered and evapd.; distn. (180-220 °C, vacuum); elem. anal.;;

70%

...Expand

: 109-72-8
n-butyllithium

: 53268-50-1
chloro(trifluoromethyl)disulfane

: 1-Trifluoromethyldisulfanyl-butane

Conditions

Conditions	Yield
	68%
	68%

: 109-72-8
n-butyllithium

: 131498-79-8
1-trimethylsiloxy-3,7,10-trimethylgermatrane

: 1067-42-1
tetrabutylgermanium

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: LiOSi(CH3)3; a suspn. of germatrane in THF was treated with an excess of n-BuLi in n-hexane at room temp. for 4 h; evap., filtered;	65%

: 1271-86-9
N,N-dimethylaminomethylferrocene

: 109-72-8
n-butyllithium

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 162762-18-7, 212901-69-4, 174225-69-5
2-(N,N-dimethylaminomethyl)ferrocenecarboxaldehyde

Conditions

Conditions	Yield
In not given addn. of LiBu (1 equiv., room temp.), stirring (24 h), addn. of DMF (-78°C), stirring (4 h, room temp.), hydrolysis; extn. (Et2O), chromy. (alumina, Et2O/pentane 1:2); elem. anal.;	62%

...Expand

: 109-72-8
n-butyllithium

: 70559-35-2
1-bromogermatrane

: 1067-42-1
tetrabutylgermanium

Conditions

Conditions	Yield
In tetrahydrofuran a suspn. of germatrane in THF was treated with an excess of n-BuLi in n-hexane at room temp. for 4 h;	61%

: 109-72-8
n-butyllithium

: 1231953-83-5
trimethylamine borane

: lithium borohydride

Conditions

Conditions	Yield
In hexane under dry N2, refluxing for 20 h;	60%

: 26743-81-7
tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)

: 109-72-8
n-butyllithium

: 115-09-3
methylmercury(II) chloride

: Mo(CO)4((C6H5)2PCH(HgCH3)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Mo-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

: 16743-46-7
tetracarbonyl-bis(diphenylphosphino)methane-chromium(0)

: 109-72-8
n-butyllithium

: 115-09-3
methylmercury(II) chloride

: Cr(CO)4((C6H5)2PCH(HgCH3)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Cr-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

: 109-72-8
n-butyllithium

: 41830-14-2
tetracarbonyl-bis(diphenylphosphino)methane-tungsten(0)

: 115-09-3
methylmercury(II) chloride

: W(CO)4((C6H5)2PCH(HgCH3)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of W-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

: 26743-81-7
tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)

: 109-72-8
n-butyllithium

: 107-27-7
ethylmercury(II) chloride

: Mo(CO)4((C6H5)2PCH(HgCH2CH3)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Mo-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

: 16743-46-7
tetracarbonyl-bis(diphenylphosphino)methane-chromium(0)

: 109-72-8
n-butyllithium

: 107-27-7
ethylmercury(II) chloride

: Cr(CO)4((C6H5)2PCH(HgCH2CH3)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Cr-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

: 109-72-8
n-butyllithium

: 41830-14-2
tetracarbonyl-bis(diphenylphosphino)methane-tungsten(0)

: 107-27-7
ethylmercury(II) chloride

: W(CO)4((C6H5)2PCH(HgCH2CH3)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of W-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

: 26743-81-7
tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)

: 109-72-8
n-butyllithium

: 100-56-1
phenylmercury(II) chloride

: Mo(CO)4((C6H5)2PCH(HgC6H5)P(C6H5)2)

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Mo-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

...Expand

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: F, Corrosive C, Dangerous N
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.

Product Name

n-Butyllithium

Synthetic route

n-Butyllithium Chemical Properties

n-Butyllithium Uses

n-Butyllithium Production

n-Butyllithium Safety Profile

n-Butyllithium Specification

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