tert-Butyllithium

tert-Butyllithium Basic information
Product Name:tert-Butyllithium
Synonyms:TERT-BUTYLLITHIUM;T-BUTYLLITHIUM;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
CAS:594-19-4
MF:C4H9Li
MW:64.06
EINECS:209-831-5
Product Categories:metal alkyl
Mol File:594-19-4.mol
tert-Butyllithium Structure
tert-Butyllithium Chemical Properties
Boiling point 36-40 °C
density 0.69 g/mL at 20 °C
vapor density ~3 (vs air)
Fp 20 °F
storage temp. 2-8°C
form liquid
color slightly cloudy
Sensitive Air & Moisture Sensitive
BRN 3587204
Exposure limitsACGIH: 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)
InChIKeyBKDLGMUIXWPYGD-UHFFFAOYSA-N
CAS DataBase Reference594-19-4(CAS DataBase Reference)
EPA Substance Registry SystemLithium, (1,1-dimethylethyl)- (594-19-4)
Safety Information
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
3-10
TSCA Yes
HazardClass 4.3
PackingGroup I
HS Code 29319090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
tert-Butyllithium Usage And Synthesis
Descriptiontert-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 Propertiestert-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.
Applicationtert-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.
Preparationtert-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.
tert-Butyllithium Preparation Products And Raw materials
Preparation Products3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOL-4-AMINE-->(3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOL-4-YL)METHANOL-->ETHYL 3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE-->3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID-->3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBONITRILE-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBONITRILE-->(1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-YL)METHANAMINE-->3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE-->1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID-->(3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-YL)METHANAMINE-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBALDEHYDE-->(1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-YL)METHANOL-->3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-AMINE-->(3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-YL)METHANOL-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-AMINE-->ETHYL 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE-->ETHYL 1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID-->tert-Butyldimethylsilyl chloride-->2-METHOXY-3-PYRIDINECARBOXALDEHYDE-->4-BROMO-2-(TRIFLUOROMETHYL)-5-METHOXYPYRIDINE-->N-(6-FLUORO-3-FORMYLPYRIDIN-2-YL)PIVALAMIDE-->Di-tert-butylchlorophosphane-->Tri-tert-butylphosphine-->5-CHLORO-3-METHYLBENZO[B]THIOPHENE-2-SULFONAMIDE-->TERT-BUTYL 4-FORMYLPYRIDIN-3-YLCARBAMATE-->(3-BROMO-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->5-CHLORO-3-METHYLBENZO[B]THIOPHENE-2-SULFONYL CHLORIDE-->1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER-->Tri-tert-butylphosphine tetrafluoroborate-->Indole-4-boronic acid-->1-TERT-BUTYL-4-BROMO-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->5-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE-->3-Bromofuran-->ORNOPROSTIL
SEC-BUTYLLITHIUM ISOBUTYLLITHIUM LITHIUM METHOXIDE METHYLLITHIUM AS COMPLEX WITH LITHIUM Lithium hexamethyldisilazide tert-Butylsulfinyl chloride tert-Butylbenzene Di-tert-butyl disulfide tert-Butanesulfinamide n-Butyllithium TERT-BUTYLLITHIUM,15%SOLUTIONINPENTANE tert-Butyllithium LITHIUM N-PROPYLCYCLOPENTADIENIDE LITHIUM N-BUTYLCYCLOPENTADIENIDE LITHIUM TERT-BUTYLCYCLOPENTADIENIDE Ethyllithium ISOPROPYLLITHIUM Lithium

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