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Lithium diisopropylamide
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Name

Lithium diisopropylamide

 EINECS 223-893-0
CAS No. 4111-54-0 Density 0.79
PSA 3.24000 LogP 1.56950
Solubility Decomposes in water Melting Point 38-42ºC
Formula C6H15 N . Li Boiling Point 83.9 °C at 760 mmHg
Molecular Weight 107.125 Flash Point -18 ºC
Transport Information UN 3393 Appearance dark yellow to orange or dark red-brown solution
Safety S16;S26;S36/37/39;S45;S60;S61;S8 Risk Codes R11;R14;R15;R19;R35;R51/53;R65;R67   
Molecular Structure Molecular Structure of 4111-54-0 (Lithium diisopropylamide) Hazard Symbols
Synonyms

2-Propanamine,N-(1-methylethyl)-, lithium salt (9CI); Diisopropylamine, lithium salt (8CI);Lithium, (diisopropylamino)- (7CI); (Diisopropylamino)lithium; LDA; LDA(reagent); Lithiodiisopropylamine; Lithium diisopropylamide; Lithiumdiisopropylamine; N-(1-Methylethyl)-2-propanamine lithium salt;N-Lithiodiisopropylamide

Article Data 190

Lithium diisopropylamide Synthetic route

108-18-9

diisopropylamine

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
With styrene; lithium In tetrahydrofuran at -5 - 35℃; Solvent; Inert atmosphere;97.6%
With styrene; lithium In diethyl ether for 2h; Heating;95%
With n-butyllithium In pentane at 0 - 20℃; for 1.33333h;71%
108-89-4

picoline

60-29-7

diethyl ether

116332-54-8

4-fluoro-N-methoxy-N-methylbenzamide

A

152121-20-5

2-(4-Cyanophenyl)-4-(4-fluorophenyl)-1-N-hydroxy-5-(4-pyridyl)imidazole

B

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
In diisopropylamineA 72%
B n/a
With n-butyllithium In diisopropylamineA 72%
B n/a
1749-29-7

2-pyridylmethyllithium

108-18-9

diisopropylamine

A

109-06-8

α-picoline

B

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant;
109-72-8, 29786-93-4

n-butyllithium

108-18-9

diisopropylamine

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
With tetramethylsilane In tetrahydrofuran; hexane at -73℃; for 0.0333333h;100 % Spectr.
In tetrahydrofuran; hexane at -78℃; for 0.25h;
In tetrahydrofuran; hexane
110-18-9

N,N,N,N,-tetramethylethylenediamine

108-18-9

diisopropylamine

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
With n-butyllithium In hexane at 0℃;
38227-87-1

2,2,6,6-tetramethylpiperidinyl-lithium

108-18-9

diisopropylamine

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
In tetrahydrofuran at -47℃; Thermodynamic data; Rate constant; ΔG(excit.);
In tetrahydrofuran at -47℃; Thermodynamic data; Equilibrium constant; Rate constant; ΔG(excit.);
881-42-5

diphenylmethyllithium

108-18-9

diisopropylamine

A

101-81-5

Diphenylmethane

B

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; Equilibrium constant;
99631-63-7

C5H7Li

108-18-9

diisopropylamine

A

4111-54-0

lithium diisopropyl amide

B

78-79-5

isoprene

Conditions
ConditionsYield
In tetrahydrofuran at -70℃; Equilibrium constant;
38227-84-8, 84602-07-3, 84602-08-4

Li(cis-2,6-dimethylpiperidine(-1H))

108-18-9

diisopropylamine

A

766-17-6, 1218906-26-3

(2R,6S)-2,6-dimethylpiperidine

B

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
In tetrahydrofuran at -65℃; Thermodynamic data; Rate constant; ΔG(excit.);
In tetrahydrofuran at -65℃; Thermodynamic data; Equilibrium constant; Rate constant; ΔG(excit.);
68695-92-1

(4,4'-Dimethyldiphenylmethyl)lithium

108-18-9

diisopropylamine

A

4957-14-6

4,4'-dimethyldiphenylmethane

B

4111-54-0

lithium diisopropyl amide

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; Equilibrium constant;

Lithium diisopropylamide Chemical Properties


IUPAC Name: Lithium di(propan-2-yl)azanide
Molecular Formula: C6H14LiN
Molecular Weight: 107.12306 g/mol
EINECS: 223-893-0
Classification Code: TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]
Melting Point:
storage temperature: 2-8 °C
Water Solubility: decomposes
Density: 0.79 g/cm3
Flash Point: 91 °F
Enthalpy of Vaporization: 30.4 kJ/mol
Boiling Point: 83.9 °C at 760 mmHg
Vapour Pressure of Lithium diisopropylamide (CAS NO.4111-54-0): 74 mmHg at 25 °C

Lithium diisopropylamide Uses

 Lithium diisopropylamide (CAS NO.4111-54-0) is a strong base used in organic chemistry for the deprotonation of weakly acidic compounds. It is most widely used even though KDA is more effective.

Lithium diisopropylamide Production

 Lithium diisopropylamide (CAS NO.4111-54-0) is commonly formed by treating a cooled (0 to -78 °C) tetrahydrofuran (THF) solution of diisopropylamine with n-butyllithium.

Lithium diisopropylamide Safety Profile

Hazard Codes: CorrosiveC,DangerousN,FlammableF
Risk Statements: 14-17-34-67-65-51/53-35-19-15-11-50/53-14/15-10-40-23/24/25 
R14 :Reacts violently with water. 
R17:Spontaneously flammable in air. 
R34:Causes burns.
R67:Vapours may cause drowsiness and dizziness.
R65:Harmful: may cause lung damage if swallowed. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R35:Causes severe burns. 
R19:May form explosive peroxides.
R15:Contact with water liberates extremely flammable gases.
R11:Highly flammable. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R14 :Reacts violently with water. 
R10:Flammable. 
R40:Limited evidence of a carcinogenic effect. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-43-45-60-61-62-8-16-23-33-27 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S43:In case of fire use ... (there follows the type of fire-fighting equipment to be used.) 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S60:This material and its container must be disposed of as hazardous waste.
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. 
S8:Keep container dry. 
S16:Keep away from sources of ignition.
S23:Do not breathe vapour. 
S33:Take precautionary measures against static discharges. 
S27:Take off immediately all contaminated clothing.
RIDADR: UN 3399 4.3/PG 2
WGK Germany of Lithium diisopropylamide (CAS NO.4111-54-0): 3

Lithium diisopropylamide Standards and Recommendations

THF,wt%: 22
Heptane,wt%: 29
Ethylbenzene,wt%: 13

Lithium diisopropylamide Specification

  Lithium diisopropylamide (CAS NO.4111-54-0), its Synonyms are 2-Propanamine, N-(1-methylethyl)-, lithium salt ; 2-Propanamine, N-(1-methylethyl)-, lithium salt (1:1) . It is dark yellow to orange or dark red-brown solution.

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