Lithium diisopropylamide supplier

Name
Lithium diisopropylamide
EINECS 223-893-0
CAS No. 4111-54-0
Article Data190
CAS DataBase
Density 0.79
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
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
PSA 3.24000
LogP 1.56950

Synthetic route

: 108-18-9
diisopropylamine

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
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

Conditions	Yield
In diisopropylamine	A 72% B n/a
With n-butyllithium In diisopropylamine	A 72% B n/a

...Expand

: 1749-29-7
2-pyridylmethyllithium

: 108-18-9
diisopropylamine

A: 109-06-8
α-picoline

B: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant;

...Expand

: 109-72-8, 29786-93-4
n-butyllithium

: 108-18-9
diisopropylamine

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In tetrahydrofuran at -47℃; Thermodynamic data; Rate constant; ΔG(excit.);
In tetrahydrofuran at -47℃; Thermodynamic data; Equilibrium constant; Rate constant; ΔG(excit.);

...Expand

: 881-42-5
diphenylmethyllithium

: 108-18-9
diisopropylamine

A: 101-81-5
Diphenylmethane

B: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In tetrahydrofuran at 30℃; Equilibrium constant;

...Expand

: 99631-63-7
C5H7Li

: 108-18-9
diisopropylamine

A: 4111-54-0
lithium diisopropyl amide

B: 78-79-5
isoprene

Conditions

Conditions	Yield
In tetrahydrofuran at -70℃; Equilibrium constant;

...Expand

: 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

Conditions	Yield
In tetrahydrofuran at -65℃; Thermodynamic data; Rate constant; ΔG(excit.);
In tetrahydrofuran at -65℃; Thermodynamic data; Equilibrium constant; Rate constant; ΔG(excit.);

...Expand

: 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

Conditions	Yield
In tetrahydrofuran at 30℃; Equilibrium constant;

...Expand

: 110426-35-2
C21H27Li

: 108-18-9
diisopropylamine

A: 19099-48-0
1,1-bis(4-t-butylphenyl)methane

B: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In tetrahydrofuran at 30℃; Equilibrium constant;

...Expand

: 849585-22-4
LACTIC ACID

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran

: 109-72-8, 29786-93-4
n-butyllithium

: 7087-68-5
N-ethyl-N,N-diisopropylamine

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In hexane
In tetrahydrofuran; hexane at -78 - 0℃; for 0.333333 - 0.566667h; Product distribution / selectivity;
In tetrahydrofuran at -70 - -5℃;

: 109-72-8, 29786-93-4
n-butyllithium

: 75-31-0
isopropylamine

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In hexane at 0℃;
In tetrahydrofuran; hexane at 0℃; for 0.166667h; Product distribution / selectivity;
In tetrahydrofuran; hexanes at 0℃; Product distribution / selectivity;

: 17715-69-4
1-Bromo-2,4-dimethoxybenzene

: 105-53-3
diethyl malonate

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
With n-butyllithium; NaH; nitrogen In tetrahydrofuran

: 39931-77-6
pyridin-3-yl-acetic acid ethyl ester

: 4-(dimethylamino)pyridinium tribromide

: ammonium chloride

A: 347186-70-3
bromo-pyridin-3-yl-acetic acid ethyl ester

B: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran

...Expand

: 39931-77-6
pyridin-3-yl-acetic acid ethyl ester

: 4-(dimethylamino)pyridinium tribromide

A: 347186-70-3
bromo-pyridin-3-yl-acetic acid ethyl ester

B: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
With n-butyllithium; chloro-trimethyl-silane; diisopropylamine In tetrahydrofuran

...Expand

: 62094-47-7
cis dioxolanone

: 108-18-9
diisopropylamine

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane

5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxy aldehyde: 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxy aldehyde

: 4-chloro-1-(diethoxyphosphorylmethyl)-2-fluorobenzene

A: 5-[5-[(E)-2-(4-chlorophenyl)-2-fluorovinyl]-2-thienyl]-1-methyl-3-trifluoromethyl-1H-pyrazole

B: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In tetrahydrofuran

...Expand

: methyl 3-(5-benzyloxyindolyl)propanoate

: 107-08-4
1-iodo-propane

: 4111-54-0
lithium diisopropyl amide

Conditions

Conditions	Yield
In tetrahydrofuran

: 100938-86-1
2-(2,4,6-tri-tert-butylphenyl)phosphaacetylene

: 4111-54-0
lithium diisopropyl amide

: 74-88-4
methyl iodide

: 736135-44-7, 943220-13-1
1-diisopropylamino-3-methyl-1,3-diphosphacyclobutane-2,4-diyl

Conditions

Conditions	Yield
Stage #1: 2-(2,4,6-tri-tert-butylphenyl)phosphaacetylene; lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 1.25h; Stage #2: methyl iodide In tetrahydrofuran	100%

...Expand

: CH3OBC13H18

: 4111-54-0
lithium diisopropyl amide

: Li(1+)*CH3OBC13H17(1-)=Li[CH3OBC13H17]

Conditions

Conditions	Yield
In tetrahydrofuran; hexane N2-atmosphere; stirring (room temp., 80 h), evapn.; extg. (hexane), filtering, evapn. (vac.);	100%

: 162147-89-9
1--1-cyclopentanol

: 4111-54-0
lithium diisopropyl amide

A: 66633-64-5
benzenesulfinic acid diisopropylamide

B: 822-87-7
2-Chlorocyclohexanone

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h;	A 99% B 30%

...Expand

: 109-77-3
malononitrile

: (Z)-N-(3-(dimethylamino)-2-(trifluoromethyl)allylidene)-N-methylmethanaminium chloride salt

: 4111-54-0
lithium diisopropyl amide

: diisopropylammonium 1,1,5,5-tetracyano-3-trifluoromethyl-1,3-pentadienide

Conditions

Conditions	Yield
Stage #1: malononitrile; lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: (Z)-N-(3-(dimethylamino)-2-(trifluoromethyl)allylidene)-N-methylmethanaminium chloride salt In tetrahydrofuran; hexane at 20℃; for 3h;	99%

...Expand

: 4282-40-0
1-Iodoheptane

: 1631-73-8
trimethylstannane

: 4111-54-0
lithium diisopropyl amide

A: 142-82-5
n-heptane

B: 661-69-8
hexamethyldistannane

C: 1068-71-9
diisopropyl(trimethylstannyl)amine

Conditions

Conditions	Yield
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (1.0 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 99% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.8 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 98% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.6 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 94% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.4 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 84% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.2 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 74% B 0% C n/a

...Expand

: 223565-68-2
1,1,5,5-tetra(tert-butyl)-hexamethyl-1,5-distanna-2,3,4-trisilapentane

: 4111-54-0
lithium diisopropyl amide

: 339048-86-1
1,5-dilithio-1,1,5,5-tetra(tert-butyl)-hexamethyl-1,5-distanna-2,3,4-trisilapentane

Conditions

Conditions	Yield
In tetrahydrofuran; hexane byproducts: HN(Pr-i)2; 2 equiv. of Li-amide compd. in 1:1 THF was added dropwise to a cooled (0°C) soln. (THF-hexane(1:1)) of Sn-compd., stirring for 1 h at th is temp.; temp. may be varied between -30 and 0 °C, under Ar or N2; detected by NMR;	99%

: 1,1'-bis-benzyloxy-4,4'-diisopropyl-1,6,1',6'-tetrahydro-[2,2']biborininyl

: 4111-54-0
lithium diisopropyl amide

: 2Li(1+)*((CH3)2CHC5H3BOCH2C6H5)2(2-)=Li2((CH3)2CHC5H3BOCH2C6H5)2

Conditions

Conditions	Yield
In tetrahydrofuran addn. of LDA in THF to a soln. diborabiphenyl derivative in THF at room temp. under stiring, stirring for 1 h at room temp.; removal of volatiles under vac.,;	99%

: 1631-73-8
trimethylstannane

: 4111-54-0
lithium diisopropyl amide

A: 1333-74-0
hydrogen

B: 661-69-8
hexamethyldistannane

Conditions

Conditions	Yield
With O In cyclohexane byproducts: i-Pr2NH; LDA (1.88 mmol) in C6H12 placed in Schlenk tube at 0°C under Ar, TMTH (3.76 mmol) added, stirred for 30 min, hydrolysis; Sn2Me6 detected by GC;	A 98% B 93%
In diethyl ether; cyclohexane byproducts: i-Pr2NH; TMTH in Et2O cooled to 0°C under Ar, LDA in cyclohexane (1.6 M) added via syringe, stirred for 60 min at room temp., hydrolysis;	A 95% B 90%
In diethyl ether byproducts: i-Pr2NH; LDA (1.88 mmol) in C6H12 placed in Schlenk tube at 0°C under Ar, TMTH (3.76 mmol) added, stirred for 30 min, hydrolysis; Sn2Me6 detected by GC;	A 93% B 83%

...Expand

: 162732-80-1
10-dicyclohexylsulfamoyl-D-isobornyl (E)-7-bromohept-2-enoate

: 4111-54-0
lithium diisopropyl amide

: 10-dicyclohexylsulfamoyl-D-isobornyl 7-bromo-3<(1-methylethyl)amino>heptanoate

Conditions

Conditions	Yield
In tetrahydrofuran at -72 - -68℃; for 1.83333h;	97%

: 1631-73-8
trimethylstannane

: 2695-47-8
6-Bromo-1-hexene

: 4111-54-0
lithium diisopropyl amide

A: 592-41-6
1-hexene

B: 96-37-7
methyl-cyclopentane

C: 661-69-8
hexamethyldistannane

Conditions

Conditions	Yield
In diethyl ether; cyclohexane to 6-bromo-1-hexene (1.04 mmol) and 2 equiv. of Me3SnH in Et2O at 0°C added LDA (1.04 mmol, in cyclohexane) under Ar, react. time 20 min, quenched with water; analyzed by GLPC;	A 77% B 16% C 97%
In diethyl ether; cyclohexane to 6-bromo-1-hexene (1.04 mmol) and 1 equiv. of Me3SnH in Et2O at 0°C added LDA (1.04 mmol, in cyclohexane) under Ar, react. time 20 min, quenched with water; analyzed by GLPC;	A 41% B 18% C 86%
In hexane; cyclohexane to 6-bromo-1-hexene (1.04 mmol) and 2 equiv. of Me3SnH in hexane at 0°C added LDA (1.04 mmol, in cyclohexane) under Ar, react. time 20 min, quenched with water; analyzed by GLPC;	A 76% B 18% C 27%
In hexane; cyclohexane to 6-bromo-1-hexene (1.04 mmol) and 1 equiv. of Me3SnH in hexane at 0°C added LDA (1.04 mmol, in cyclohexane) under Ar, react. time 20 min, quenched with water; analyzed by GLPC;	A 45% B 32% C 48%

...Expand

: 111-83-1
1-bromo-octane

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

: 4111-54-0
lithium diisopropyl amide

A: 111-65-9
octane

B: 813-19-4
bis(tri-n-butyltin)

Conditions

Conditions	Yield
In hexane; cyclohexane to 1-bromooctane (1 mmol) and Bu3SnH (1 mmol) in hexane at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 97% B 0%

...Expand

: C5H25B22N2(1-)*C3H9N*H(1+)

: 4111-54-0
lithium diisopropyl amide

: C5H24B22LiN2(2-)*2Li(1+)

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Schlenk technique;	97%

: 337529-91-6
bis(1-methyl-1H-imidazol-3-yl)dihydroboronium iodide

: 4111-54-0
lithium diisopropyl amide

: Li(1+)*CH3C3H2N2BH2C3H2N2CH3(1-)=LiCH3C3H2N2BH2C3H2N2CH3

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	96%

: ferrocenyl triflate

: 4111-54-0
lithium diisopropyl amide

: lithium 2-(trifluoromethylsulfonyl)ferrocenolate

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 2 - 78℃; for 0.333333h; Inert atmosphere; Schlenk technique;	96%

: 422-04-8
pentafluoropropionitrile

: 1080-32-6
O,O-diethyl benzylphosphonate

: 4111-54-0
lithium diisopropyl amide

: diisopropylamine 2-ethoxy-2-oxo-3-phenyl-4,6-bis(pentafluoroethyl)-2,5-dihydro-1,5,2-diazaphosphinine adduct

Conditions

Conditions	Yield
Stage #1: O,O-diethyl benzylphosphonate; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1h; Stage #2: pentafluoropropionitrile In tetrahydrofuran at 20℃; for 15h;	95%

...Expand

: 111-83-1
1-bromo-octane

: 1631-73-8
trimethylstannane

: 4111-54-0
lithium diisopropyl amide

A: 111-65-9
octane

B: 661-69-8
hexamethyldistannane

Conditions

Conditions	Yield
In diethyl ether; cyclohexane to 1-bromooctane (1 mmol) and TMTH (1 mmol) in Et2O at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 54% B 95%
With p-benzoquinone In hexane; cyclohexane to 1-bromooctane (1 mmol), TMTH (1 mmol), and benzoquinone (10 mol%) in hexane at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 91% B 5%
With meta-dinitrobenzene; p-benzoquinone In hexane; cyclohexane to 1-bromooctane (1 mmol), TMTH (1 mmol), benzoquinone (10 mol%), and m-dinitrobenzene (5 mol%) in hexane at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 83% B 2%
In hexane; cyclohexane to 1-bromooctane (1 mmol) and TMTH (1 mmol) in hexane at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 70% B 50%

...Expand

: 127-19-5
N,N-dimethyl acetamide

: 1529-47-1
chlorotrimethylgermane

: 4111-54-0
lithium diisopropyl amide

: 123347-42-2
N,N-dimethyl(trimethylgermyl)acetamide

Conditions

Conditions	Yield
In tetrahydrofuran; hexane (Ar or N2); dropwise addn. of N,N-dimethylacetamide to a soln. of LDA at -78 °C; after 1 h stirring dropwise addn. of GeCl(CH3)3 and addnl. stirring for 2 h at the same temp.; quenching (satd. aq. NH4Cl); extn. (benzene); drying (MgSO4) of the organic layer; concn.; distn.;	95%

...Expand

: 2633-75-2
ethylzinc chloride

: 4111-54-0
lithium diisopropyl amide

: 109930-69-0
N-(ethylzinc) diisopropylamine

Conditions

Conditions	Yield
In diethyl ether byproducts: LiCl; ether soln. of EtZnCl was added to a suspn. of i-Pr2NLi in ether over 2 min under N2, stirred for 15 min; filtered, evapd., residue was dissolved in pentane, filtered, evapd; elem. anal.;	95%

: 220696-16-2
N,N-diethyl-1-amino-1,2-dihydro-1-boratanaphthalene

: 220696-18-4
N,N-diethyl-1-amino-1,4-dihydro-1-boratanaphthalene

: 4111-54-0
lithium diisopropyl amide

: lithium N,N-diethyl-1-amino-1-boratanaphthalene

Conditions

Conditions	Yield
In diethyl ether N2-atmosphere; addn. of LDA (1.1 equiv.) to mixt. of boratanaphthalenes at -78°C, stirring (2 h at -78°C, 10 h at 25°C); evapn., washing (pentane), drying;	95%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 1365272-12-3
3',5'-difluoro-[1,1'-biphenyl]-4-carbonitrile

: 4111-54-0
lithium diisopropyl amide

: 1381940-52-8
C22H29F2NOSi

Conditions

Conditions	Yield
at -68℃; Inert atmosphere;	95%

...Expand

: 4111-54-0
lithium diisopropyl amide

: C6H14N3O(1-)*Li(1+)

Conditions

Conditions	Yield
With dinitrogen monoxide In tetrahydrofuran for 4h;	95%
With dinitrogen monoxide In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h;

: 78782-17-9
4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane

: 4111-54-0
lithium diisopropyl amide

: bis((4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)lithium

Conditions

Conditions	Yield
In tetrahydrofuran; hexane at -25 - 20℃; for 1.33333h; Inert atmosphere; Glovebox;	95%

: 4282-40-0
1-Iodoheptane

: 1631-73-8
trimethylstannane

: 4111-54-0
lithium diisopropyl amide

A: 142-82-5
n-heptane

B: 661-69-8
hexamethyldistannane

Conditions

Conditions	Yield
In hexane; cyclohexane to 1-iodoheptane (1 mmol) and TMTH (1 mmol) in hexane at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 94% B 0%
In diethyl ether; cyclohexane to 1-iodoheptane (1 mmol) and TMTH (1 mmol) in Et2O at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC;	A 78% B 26%

...Expand

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

: 4111-54-0
lithium diisopropyl amide

A: 1333-74-0
hydrogen

B: 813-19-4
bis(tri-n-butyltin)

Conditions

Conditions	Yield
In diethyl ether; cyclohexane byproducts: i-Pr2NH; Bu3SnH in Et2O cooled to 0°C under Ar, LDA in cyclohexane (1.6 M) added via syringe, stirred for 60 min at room temp., hydrolysis;	A 90% B 94%

...Expand

: 1271-55-2
acetylferrocene

: 814-49-3
diethyl chlorophosphate

: 4111-54-0
lithium diisopropyl amide

: 1271-47-2
ferroceneacetylene

Conditions

Conditions	Yield
With water In tetrahydrofuran inert atmosphere; addn. of LDA in THF at -78°C to soln. of Fe-complex; reaction for 1 h; addn. of phosphate; reaction for 1 h; mixt. raised to room temp.; addn. of LDA in THF at -78°C; warmed to room temp.; hydrolysis at 0°C;; extn. of organic layer with CH2Cl2; dried over MgSO4; evapn.; purifn. of oil by flash chromy. (pentane-ether 2:1); crystn. of first yellow fraction (0°C, pentane); elem. anal.;	94%

Yield

With water In tetrahydrofuran inert atmosphere; addn. of LDA in THF at -78°C to soln. of Fe-complex; reaction for 1 h; addn. of phosphate; reaction for 1 h; mixt. raised to room temp.; addn. of LDA in THF at -78°C; warmed to room temp.; hydrolysis at 0°C;; extn. of organic layer with CH2Cl2; dried over MgSO4; evapn.; purifn. of oil by flash chromy. (pentane-ether 2:1); crystn. of first yellow fraction (0°C, pentane); elem. anal.;

94%

...Expand

: 77310-69-1
(CO)4WCC6H4CH3(NHCH2CHCH2)

: 4111-54-0
lithium diisopropyl amide

: 90245-85-5
cis-tetracarbonyl[((Z)-η2-N-allyl-N-methylamino)(p-tolyl)carbene]tungsten(0)

Conditions

Conditions	Yield
With CH3I In tetrahydrofuran a soln. of lithium diisopropylamide in THF was added to soln. of W-complex in THF at -72°C, soln. was warmed to room temp., cooled back to -72°C and CH3I was added, soln. was warmed to room temp. underN2; preparative TLC (silica gel, CH2Cl2-hexane) gave solid ppt.;	94%

: (CO)4Re(η2-C(Me)C(CO2Me)C(OEt))

: 21050-13-5
bis(triphenylphosphine)iminium chloride

: 4111-54-0
lithium diisopropyl amide

: 724461-50-1
(Ph3P)2N[(CO)4Re(η2-C(=CH2)C(CO2Me)C(OEt))]

Conditions

Conditions	Yield
In tetrahydrofuran; hexane (Ar); addn. of a soln. of lithium compd. in hexane to a soln. of rheniumcomplex in THF at -78°C, stirring for 1 h at -78°C, addn. of PPNCl, stirring and warming to room temp.; filtration, concn., addn. of hexane, cooling to 0°C, sepn., washing ppt. with hexane, drying for 24 h in vac.;	94%

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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: Corrosive C, Dangerous N,F
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.

Product Name

Lithium diisopropylamide

Synthetic route

Lithium diisopropylamide Chemical Properties

Lithium diisopropylamide Uses

Lithium diisopropylamide Production

Lithium diisopropylamide Safety Profile

Lithium diisopropylamide Standards and Recommendations

Lithium diisopropylamide Specification

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