ChemicalBook > CAS DataBase List > tert-Butyllithium

tert-Butyllithium

Product Name
tert-Butyllithium
CAS No.
594-19-4
Chemical Name
tert-Butyllithium
Synonyms
T-BULI;T-BUTYLLITHIUM;TERT-BUTYLLITHIUM;LITHIUM TERT-BUTYL;Copper - titanium (1:1);Nominally1.5Minn-Pentane;tert-Butyllithium solution;(1,1-Dimethylethyl)lithium;(1,1-dimethylethyl)-lithiu;T-BuLi1.7Msolutioninpentane
CBNumber
CB2229465
Molecular Formula
C4H9Li
Formula Weight
64.06
MOL File
594-19-4.mol
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tert-Butyllithium Property

Boiling point:
36-40 °C
Density 
0.69 g/mL at 20 °C
vapor density 
~3 (vs air)
Flash point:
20 °F
storage temp. 
2-8°C
form 
liquid
color 
slightly cloudy
Sensitive 
Air & Moisture Sensitive
BRN 
3587204
Exposure limits
ACGIH: TWA 1000 ppm
OSHA: TWA 1000 ppm(2950 mg/m3)
NIOSH: IDLH 1500 ppm; TWA 120 ppm(350 mg/m3); Ceiling 610 ppm(1800 mg/m3)
InChIKey
BKDLGMUIXWPYGD-UHFFFAOYSA-N
CAS DataBase Reference
594-19-4(CAS DataBase Reference)
EPA Substance Registry System
Lithium, (1,1-dimethylethyl)- (594-19-4)
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Safety

Hazard Codes 
F,C,N
Risk Statements 
11-15-17-34-51/53-65-66-67-50/53-38-14/15
Safety Statements 
26-36/37/39-43-45-62-61-16-33-9
RIDADR 
UN 3394 4.2/PG 1
WGK Germany 
1
F 
3-10
TSCA 
Yes
HazardClass 
4.3
PackingGroup 
I
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H250Catches fire spontaneously if exposed to air

H252Self-heating in large quantities; may catch fire

H260In contact with water releases flammable gases which may ignite spontaneously

H304May be fatal if swallowed and enters airways

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

H336May cause drowsiness or dizziness

H410Very toxic to aquatic life with long lasting effects

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P222Do not allow contact with air.

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P370+P378In case of fire: Use … for extinction.

P405Store locked up.

P422Store contents under …

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
186198
Product name
tert-Butyllithium solution
Purity
1.7M in pentane
Packaging
4x25ml
Price
$81.4
Updated
2024/03/01
Sigma-Aldrich
Product number
94439
Product name
tert-Butyllithium solution
Purity
1.6-3.2?M in heptane
Packaging
100mL
Price
$203
Updated
2024/03/01
Sigma-Aldrich
Product number
186198
Product name
tert-Butyllithium solution
Purity
1.7M in pentane
Packaging
8l
Price
$1490
Updated
2024/03/01
Alfa Aesar
Product number
044125
Product name
tert-Butyllithium
Purity
nominally 1.5M in n-pentane
Packaging
250ml
Price
$104
Updated
2021/12/16
Alfa Aesar
Product number
041251
Product name
tert-Butyllithium, nominally 1.5M in n-pentane
Purity
packaged under Argon in resealable ChemSeal? bottles
Packaging
50ml
Price
$27.5
Updated
2021/12/16
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tert-Butyllithium Chemical Properties,Usage,Production

Description

tert-Butyllithium solution (tert-BuLi) is an organolithium compound, used as a strong base in organic chemistry. It facilitates lithium-halogen exchange reaction and also can be employed in the deprotonation of C-H compounds and amines. it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory. Its synthesis was first reported by R. B. Woodward in 1941.

Chemical Properties

tert-Butyllithium is a colorless crystalline solid or colourless to pale yellow solution. It is more reactive than n- or sec-butyllithium and has similar properties. However, it is thermally stable. Dixon and co-workers have heated tert-Butyllithium to 100°C for 20 hr with little decomposition.

Uses

  • There are no commercial uses of t-butyllithium, but it is used as a polymerization initiator and as a metalating agent in the laboratory.
  • Alkylating and metalating agent. Reagent for the introduction of the tert-butyl group.
  • tert-Butyllithium (t-BuLi) is the most reactive of the commercially available organolithium reagents. It is supplied as a standard solution in hydrocarbon solvents, usually in a bottle sealed with a septum.

Preparation

tert-Butyllithium is not sold in large quantities. The industrial and laboratory preparations are the same: the reaction of t-butyl chloride with lithium metal in a hydrocarbon solvent. However, tert-Butyllithium is much more difficult to produce than the other isomeric butyllithium compounds and some special precautions must be taken to obtain good yields. Principally, the lithium metal must be finely divided and must contain several percent sodium. It has also been found that t-butyl alcohol in the butyl chloride is beneficial. The solvent of choice is pentane. Vigorous reflux is necessary for good yield since it apparently helps to remove lithium chloride from the surface of the metal, and pentane refluxes at about the optimum temperature. If hexane is used at the same temperature, a significantly lower yield is obtained.

Application

tert-Butyllithium solution can be used as a strong base in the synthesis of:
Alkyllithium derivatives form alkyl iodides and diiodoalkanes by halogen-lithium exchange reaction.
Inorganic polymer [(LiMo3Se3)n] from [(InMo3Se3)n] by reductive intercalation method.
Adducts of cinnamic acid (1,3- and 1,4-adducts) by reacting with C-C double of cinnamic acid.

tert-Butyllithium Preparation Products And Raw materials

Raw materials

Preparation Products

Indole-5-carboxaldehyde 3-Bromofuran ETHYL 3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE 3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID 1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBONITRILE (3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-YL)METHANOL 5-CHLORO-3-METHYLBENZO[B]THIOPHENE-2-SULFONAMIDE 1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER 3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-AMINE Di-tert-butylchlorophosphane Tri-tert-butylphosphine tetrafluoroborate 3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOL-4-AMINE ORNOPROSTIL TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE 1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBALDEHYDE (3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-YL)METHANAMINE 3-METHOXY-PYRIDINE-2-CARBALDEHYDE tert-Butyldimethylsilyl chloride 5-Acetylindole 1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID (3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOL-4-YL)METHANOL 3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBONITRILE 1-TERT-BUTYL-4-BROMO-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE Indole-4-boronic acid DI-TERT-BUTYLDICHLOROSILANE 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE (3-BROMO-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER 5-CHLORO-3-METHYLBENZO[B]THIOPHENE-2-SULFONYL CHLORIDE N-(6-FLUORO-3-FORMYLPYRIDIN-2-YL)PIVALAMIDE 4-BROMO-2-(TRIFLUOROMETHYL)-5-METHOXYPYRIDINE (1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-YL)METHANOL TERT-BUTYL 4-FORMYLPYRIDIN-3-YLCARBAMATE ETHYL 1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE 2-METHOXY-3-PYRIDINECARBOXALDEHYDE 5-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE 3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE Tri-tert-butylphosphine 1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-AMINE (1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-YL)METHANAMINE
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View Lastest Price from tert-Butyllithium manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
tert-Butyllithium 594-19-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
tert-Butyllithium 594-19-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09
Career Henan Chemical Co
Product
Tert-Butyllithium 594-19-4
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
Customized
Release date
2018-12-25

594-19-4, tert-ButyllithiumRelated Search:

LITHIUM METHOXIDE ISOBUTYLLITHIUM Lithium bis(trimethylsilyl)amide SEC-BUTYLLITHIUM tert-Butylbenzene n-Butyllithium tert-Butylsulfinyl chloride Lithium hexamethyldisilazide Di-tert-butyl disulfide tert-Butanesulfinamide METHYLLITHIUM AS COMPLEX WITH LITHIUM Ethyllithium Lithium Lithium hydride tert-Butyllithium Methyllithium LITHIUM TERT-BUTYLCYCLOPENTADIENIDE ISOPROPYLLITHIUM

  • tert-Butyllithium, nominally 1.5M in n-pentane, packaged under Argon in resealable ChemSeal^t bottle
  • ButyllithiuminpentaneMslightlycloudyliq
  • t-Butyllithium 16% in pentane (1-2M)
  • tert-Butyllithium solution
  • TERT-BUTYLLITHIUM SOLUTION, ~1.5 M IN PE NTANE
  • TERT-BUTYLLITHIUM SOLUTION IN HEPTANE
  • TERT-BUTYLLITHIUM, 1.7M SOLUTION IN PENT
  • Nominally1.5Minn-Pentane
  • packagedunderArgoninresealableChemSealbottles
  • tert-Butyllithium,nominally1.5Minn-pentane
  • TERT-BUTYLLITHIUM 1.7 M IN PENTANE
  • T-BuLi1.7Msolutioninpentane
  • tert-Butyllithium (ca. 16% in Pentane, ca. 1.6mol/L)
  • tert-Butyllithium,1.3M in pentane
  • (1,1-Dimethylethyl)lithium
  • (1,1-dimethylethyl)-Lithium
  • 1,1-Dimethyl-ethane-lithium
  • Lithium,(1,1-dimethylethyl)-
  • tert-Butyllithium, 1.9M solution in pentane, AcroSeal
  • tert-Butyllithium, 1.6M solution in pentane, AcroSeal
  • tert-ButyllithiuM, 1.6M solution in pentane, AcroSeal 800ML
  • tert-ButyllithiuM, 18% solution in heptane, AcroSeal
  • tert-ButyllithiuM, solution in pentane
  • tert-ButyllithiuM, 1.3 M solution in pentane
  • tert-ButyllithiuM, 1.3 M solution in pentane, J&KSeal
  • tert-ButyllithiuM, 1.3 M solution in Pentane, SpcSeal
  • tert-Butyllithium solution, 1.5M in n-pentane
  • TERT-BUTYLLITHIUM
  • T-BUTYLLITHIUM
  • T-BULI
  • tert-Butyllithium (ca. 18% in Pentane, ca. 1.9mol/L)
  • (1,1-dimethylethyl)-lithiu
  • tert-Butyllithium, 1.5M solution in pentane
  • tert-butyllithium, nominally 1.5m in n-pentane, packaged under argon in resealable chemseal
  • TERT-BUTYLLITHIUM 1.5M IN PENTANE
  • tert-Butyllithium, nominally 1.5M in n-pentane, packaged under Argon in resealable ChemSealTM bottles
  • tert-Butyllithium, nominally 1.5M in n-pentane, packaged under Argon in resealable ChemSeal bottles
  • Lithium-2-methyl-2-propanide, t-BuLi
  • TERT-BUTYLLITHIUM, 1.9M SOLUTION IN PENTANE
  • tert-Butyllithium1.6M solution in pentaneAcroSeal§3
  • tert-Butyllithium, nominally 1.5M in n-pentane, packaged under Argon in resealable ChemSeal^t bottles
  • LITHIUM TERT-BUTYL
  • LITHIUM-2-METHYL-2-PROPANIDE
  • tert-Butyllithium, 1.6M solution in pentane
  • Tert butyl lithium 1.3m n-pentane
  • tert-Butyllithium, 1.6 M solution in pentane, J&amp
  • tert-Butyllithium, for synthesis, 1.3 M in pentane, J&amp
  • tert-Butyllithium ISO 9001：2015 REACH
  • Copper - titanium (1:1)
  • C4H9Li TERT-BUTYLLITHIUM 594-19-4
  • tert-Butyllithium, 1.5M in n-pentane
  • 594-19-4
  • CH33CLi
  • Alkyl
  • Organolithium
  • Organometallic Reagents
  • metal alkyl