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tert-Butyllithium

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Name

tert-Butyllithium

EINECS 209-831-5
CAS No. 594-19-4 Density 0.69 g/mL at 20 °C
PSA 0.00000 LogP 1.75410
Solubility Soluble in n-pentane, soluble in solvents such as hydrocarbon and ethers Melting Point N/A
Formula C4H9Li Boiling Point 36-40 °C
Molecular Weight 64.0565 Flash Point 20 °F
Transport Information UN 3394 4.2/PG 1 Appearance colourless to pale yellow solution
Safety 26-36/37/39-43-45-62-61-16-33 Risk Codes 11-15-17-34-65-66-67-50/53-38
Molecular Structure Molecular Structure of 594-19-4 (TERT-BUTYLLITHIUM) Hazard Symbols FlammableF,CorrosiveC,DangerousN
Synonyms

Lithium,tert-butyl- (6CI,8CI);(1,1-Dimethylethyl)lithium;t-Butyllithium;tBuLi;(2-Methyl-2-propanyl)lithium;

Article Data 16

tert-Butyllithium Synthetic route

507-20-0

tertiary butyl chloride

594-19-4

tert.-butyl lithium

Conditions
ConditionsYield
With lithium In pentane at 20℃; for 2.4h; Product distribution / selectivity;35%
With lithium In cyclohexane at 40℃; for 4h; Product distribution / selectivity;12.7%
With lithium; Petroleum ether
With diethyl ether; lithium
With lithium; pentane
109-72-8, 29786-93-4

n-butyllithium

116178-96-2

1-((R)-Methanesulfinyl)-hex-1-yne

594-19-4

tert.-butyl lithium

Conditions
ConditionsYield
In pentane at -78℃; for 3h; Yield given. Title compound not separated from byproducts;
507-20-0

tertiary butyl chloride

lithium

lithium

petroleum ether

petroleum ether

594-19-4

tert.-butyl lithium

507-20-0

tertiary butyl chloride

7439-93-2

lithium

594-19-4

tert.-butyl lithium

Conditions
ConditionsYield
In tetrahydrofuran at -78℃;
75-54-7

Dichloromethylsilane

594-19-4

tert.-butyl lithium

41879-33-8

tert-butylmethylsilyl chloride

Conditions
ConditionsYield
In hexane at -5℃;100%
In pentane at 0 - 20℃; Inert atmosphere;90%
In pentane at -30 - 20℃; for 24h; Inert atmosphere;87%
In diethyl ether
Inert atmosphere;
2401-73-2

1,1,3,3-tetramethyl-1,3-dichlorodisiloxane

594-19-4

tert.-butyl lithium

67875-55-2

1,3-bis(1,1-dimethylethyl)-1,1,3,3-tetramethyldisiloxane

Conditions
ConditionsYield
In diethyl ether; pentane at -78℃; for 3h;100%
18187-17-2

2-trimethylsilanyl-acrylic acid

594-19-4

tert.-butyl lithium

1115-16-8

4,4-dimethyl-2-(trimethylsilyl)pentanoic acid

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h;100%
3582-71-6

1,5-dichlorohexamethyltrisiloxane

594-19-4

tert.-butyl lithium

1,5-di-t-butylhexamethyltrisiloxane

Conditions
ConditionsYield
In diethyl ether at -78℃; for 3h;100%
594-19-4

tert.-butyl lithium

33403-21-3

3,3-ethylendioxy-5α,10α-epoxy-17α-(trimethylsilyloxy)-estr-9(11)-en-17β-carbonitrile

68027-04-3

3,3-ethylenedioxy-11β-t-butyl-5-hydroxy-17-trimethylsilyloxy-5α-estr-9-ene-17β-carbonitrile

Conditions
ConditionsYield
With dimethylsulfide; copper(I) bromide In tetrahydrofuran; hexane 1) -40 deg C, 30 min, 2) -25 deg C, overnight;100%
594-19-4

tert.-butyl lithium

tert-Butyl-dimethyl-((1S,2S,3S,4S,5R)-1,2,4-trimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-yloxy)-silane

(1R,2S,5R,6R,7S)-2-tert-Butyl-6-(tert-butyl-dimethyl-silanyloxy)-4,5,7-trimethyl-cyclohept-3-enol

Conditions
ConditionsYield
In diethyl ether; hexane at 0℃;100%

tert-Butyllithium Specification

The tert-Butyllithium, with the CAS registry number 594-19-4, is also known as (1,1-Dimethylethyl)lithium. It belongs to the product category of Metal Alkyl. Its EINECS number is 209-831-5. This chemical's molecular formula is C4H9Li and molecular weight is 64.06. What's more, its systematic name is (2-Methyl-2-propanyl)lithium. As an organometallic compound, it has applications in organic synthesis since it is a sufficiently strong base to deprotonate many carbon acids, including benzene. tert-Butyllithium is readily available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory. tert-Butyllithium is a pyrophoric substance, and it is sensitive to air and water. This chemical can be prepared by halogenated tertiary butane and lithium metal. This reaction will need solvent 1-bromopentane. It is used as catalyst in the catalytic reaction of pharmaceutical intermediates, liquid crystal monomer and organic pesticides.

Uses of tert-Butyllithium: it can be used to produce 1-furan-2-yl-2,2-dimethyl-propan-1-ol at the temperature of 0 °C. It will need solvents diethyl ether, hexane with the reaction time of 1 hour. The yield is about 75%.

tert-Butyllithium can be used to produce 1-furan-2-yl-2,2-dimethyl-propan-1-ol at the temperature of 0 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable and is spontaneously flammable in air, so you should keep it away from sources of ignition - No smoking. If contact with water, it will liberate extremely flammable gases. This substance can cause burns and is irritating to skin. Moreover, its vapours may cause drowsiness and dizziness, and repeated exposure may cause skin dryness or cracking.This chemical is very toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. What's more, it is harmful as it may cause lung damage if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. You should take precautionary measures against static discharges. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). In case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water). You must avoid releasing it to the environment just refering to special instructions/safety data sheet. If swallowed, it will not induce vomiting, but you need to seek medical advice immediately and show this container or label.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C)[Li]
(2)Std. InChI: InChI=1S/C4H9.Li/c1-4(2)3;/h1-3H3;
(3)Std. InChIKey: BKDLGMUIXWPYGD-UHFFFAOYSA-N

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