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Lithium diisopropylamide

CAS No.
4111-54-0
Chemical Name:
Lithium diisopropylamide
Synonyms
LDA;Lithium salt;LITHIUM DIISOPROPYLAMINE;lithium,di(propan-2-yl)azanide;lithium diisopropylamide (LDA);ithium diisopropyL;DIIS;LDA THF COMPLEX;iisopropylamide;Kseal,reagent grade
CBNumber:
CB6677718
Molecular Formula:
C6H16LiN
Molecular Weight:
109.14
MDL Number:
MFCD00064449
MOL File:
4111-54-0.mol
MSDS File:
SDS
Last updated:2023-10-26 11:02:50

Lithium diisopropylamide Properties

Melting point decomposes [MER06]
Boiling point 65 °C
Density 0.864 g/mL at 25 °C (lit.)
vapor density >1 (vs air)
Flash point 91 °F
storage temp. 2-8°C
solubility soluble in ethyl ether; insoluble in hydrocarbon solvents
form liquid
color brown
Water Solubility decomposes
Sensitive Air & Moisture Sensitive
Merck 14,3196
BRN 3655042
CAS DataBase Reference 4111-54-0(CAS DataBase Reference)
FDA UNII OL028KIW1I
EPA Substance Registry System 2-Propanamine, N-(1-methylethyl)-, lithium salt (4111-54-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS05
Signal word  Danger
Hazard statements  H250-H314
Precautionary statements  P231+P232-P260-P280-P303+P361+P353-P305+P351+P338-P370+P378
Hazard Codes  C,N,F
Risk Statements  14-17-34-67-65-51/53-35-19-15-11-50/53-14/15-10-40-23/24/25-62-63-37-48/20
Safety Statements  26-36/37/39-43-45-60-61-62-8-16-23-33-27
RIDADR  UN 3399 4.3/PG 2
WGK Germany  3
1-10
TSCA  Yes
HazardClass  4.2
PackingGroup  I
HS Code  29211990

Lithium diisopropylamide price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 246611 Lithium diisopropylamide 97% 4111-54-0 25g $415 2024-03-01 Buy
Sigma-Aldrich 246611 Lithium diisopropylamide 97% 4111-54-0 100g $895 2024-03-01 Buy
TCI Chemical L0171 Lithium Diisopropylamide (ca. 20% in Tetrahydrofuran/Ethylbenzene/Heptane, ca. 1.5mol/L) 4111-54-0 100mL $60 2021-12-16 Buy
TCI Chemical L0171 Lithium Diisopropylamide (ca. 20% in Tetrahydrofuran/Ethylbenzene/Heptane, ca. 1.5mol/L) 4111-54-0 500mL $167 2021-12-16 Buy
Sigma-Aldrich 774766 Lithium diisopropylamide solution 1.0 M in THF/hexanes 4111-54-0 4x25ml $62.2 2024-03-01 Buy
Product number Packaging Price Buy
246611 25g $415 Buy
246611 100g $895 Buy
L0171 100mL $60 Buy
L0171 500mL $167 Buy
774766 4x25ml $62.2 Buy

Lithium diisopropylamide Chemical Properties,Uses,Production

Chemical Properties

Lithium diisopropylamide (LDA) is a white pyrophoric powder. Freshly prepared, it is soluble in hydrocarbons (in hexane about 10 %), but it tends to precipitate irreversibly from solution as a polymer on heating or prolonged storage. In ethers the solubility is much higher, but with the exception of tetrahydropyran, LDA is decomposed at a rate depending on the ether, concentration, and temperature.
Lithium diisopropylamide can be conveniently prepared from butyllithium and diisopropylamine or purchased as a 2 mol/L (25 %) solution in THF and a mixture of various hydrocarbons. Although LDA is unstable in pure THF (at room temperature a 25% solution loses about 1% of its activity per day), the commercially available compositions containing only a limited amount of THF are satisfactory stable for technical applications.

Chemical Properties

dark yellow to orange or dark red-brown solution. Lithium Diisopropylamide (LDA) [4111- 54-0], LiN(CH(CH3)2)2, Mr 107.14 is a white pyrophoric powder. Freshly prepared, it is soluble in hydrocarbons (in hexane about 10 %), but it tends to precipitate irreversibly from solution as a polymer on heating or prolonged storage. In ethers the solubility is much higher, but with the exception of tetrahydropyran, LDA is decomposed at a rate depending on the ether, concentration, and temperature.

Uses

pH adjuster in colognes and toilet waters. In organic synthesis, particularly, the lithium salt.

Uses

Lithium diisopropylamide is a sterically hindered nonnucleophilic strong base used for selective deprotonations, especially for the production of kinetic enolates (i.e., the thermodynamically less favored isomer) and (hetero-)aromatic carbanions. In the production of the serum lipid regulating agent Gemfibrozil one key intermediate is formed by quenching an ester enolate with 1-bromo-3-chloropropane.
Lithium diisopropylamide

Uses

Lithium diisopropylamide solution (LDA) can be used:

  • As an initiator in the anionic polymerization of D,L-lactide and methyl methacrylate.
  • To facilitate ester enolization.
  • To convert carboxylic acids to enediolate intermediates for preparing trifluoromethyl ketones.
  • In ortho-lithiation of arylsulfonyloxazolidinones to prepare N-substituted saccharin analogs.
  • To catalyze ortholithiation and Fries rearrangement of aryl carbamates.
  • As a promoter in the isomerization of allylic ethers to (Z)-propenyl ethers.

Synthesis

Lithium diisopropylamide has been synthesized by two classical routes. Th 1ost widely adopted route involves in situ formation by deprotonation of diisopropylamineby an alkyllithium reagent, such as butyllithium.Addition of a solutionof butyllithium (in hexane) to a stirred solution of diisopropylamine (freshly distilledfrom CaCl) in tetrahydrofuran directly gives the required solution of lithium diisopropylamide in tetrahydrofuran. This deprotonation process has been reported to be efficient over a wide temperature range (from -78°C to 25°C). The resulting solution of lithium diisopropylamide in tetrahydrofuran appears to be stable, and consequently canbe stored at room temperature for a short period without loss of basicity.
Lithium diisopropylamide can also be synthesized directly by addition of lithium todiisopropylamine.This approach gives better quality crystalline lithium diisopropylamide, especially if required for single-crystal X-raystructure determination, than the butyllithium route.The synthesis of lithium diiso-propylamide by in situ deprotonation of diisopropylamine in tetrahydrofuran by analkyllithium reagent is, however, the most commonly used method.Butyllithium isusually the alkyllithium of choice, but otheralkyllithiums have been used (e.g., MeLi)

General Description

This material is in a solution of THF/Hexanes (ca. 1:7 ratio, respectively)

Flammability and Explosibility

Spontaneously flammable in air (pyrophoric)

Purification Methods

It is purified by refluxing over Na wire or NaH for 30minutes and then distilled into a receiver under N2. Because of the low boiling point of the amine, a dispersion of NaH in mineral oil can be used directly in this purification without prior removal of the oil. It is HIGHLY FLAMMABLE, and is decomposed by air and moisture. [Wittig & Hesse Org Synth 50 69 1970, Beilstein 4 H 154, 4 I 369, 4 II 630, 4 III 274, 4 IV 510.]

Global( 386)Suppliers
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View Lastest Price from Lithium diisopropylamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Lithium diisopropylamide pictures 2023-08-23 Lithium diisopropylamide
4111-54-0
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Lithium diisopropylamide pictures 2023-03-06 Lithium diisopropylamide
4111-54-0
US $10.70 / Kg/Drum 10g 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
Lithium diisopropylamide pictures 2023-03-06 Lithium diisopropylamide
4111-54-0
US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
LITHIUM DIISOPROPYLAMIDE THF COMPLEX LITHIUM DIISOPROPYLAMIDE LDA THF COMPLEX DIISOPROPYLAMINOLITHIUM Lithium diisopropylamide solution n-(1-methylethyl)-2-propanaminlithiumsalt Lithium diisopropylamide, 2M solution in THF/n-heptane/ethylbenzene LITHIUMDIISOPROPYLAMIDE,2MSOLUTIONINTETRAHYDROFURAN/HEPTANE/ETHYLBENZENE Lithium dlisopropylamide LITHIUM DIISOPROPYLAMIDE, 10 WT. % SOLUT ION IN MINERAL OIL LITHIUM DIISOPROPYLAMIDE, 2.0M SOLUTION IN HEPTANE/THF/ETHYLBENZENE LITHIUM DIISOPROPYLAMIDE, 1.8M SOLUTION IN THF/HEPTANE/ETHYLBENZENE LITHIUM DIISOPROPYLAMIDE, 10 WT. % SUSPE NSION IN HEXANES Lithium diisopropylamide solution, ~2 M in THF/heptane/ethylbenzene LITHIUM DIISOPROPYLAMIDE, 2M SOLUTION IN THF/HEPTANE LITHIUM DIISOPROPYLAMIDE, 2M SOLUTION IN THF/N-HEPTANE LITHIUM DIISOPROPYLAMIDE, 2.0M SOLUTION IN THF/ETHYLBENZENE Lithium Diisopropylamide (25% in Tetrahydrofuran/Ethylbenzene/Heptane, ca. 2mol/L) LithiuM diisopropylaMide solution 2.0 M in THF LithiuM diisopropylaMid LithiuM diisopropylaMide solution 1.0 M in THF/hexanes LithiuM diisopropylaMide solution 1.8 M in THF/heptane/ethylbenzene LithiuM diisopropylaMide solution 2.0 M in THF/heptane/ethylbenzene LithiuM diisopropylaMide, 2.0 M solution in THF/n-heptane ethylbenzene, SpcSeal LithiuM diisopropylaMide, 2.0 M solution in THF/n-heptane/ethylbenzene (26%/28%/13%) LithiuM diisopropylaMide, 2.0 M solution in THF/n-heptane/ethylbenzene (26%/28%/13%), J&KSeal Lithium diisopropylamide, 2M in THF/heptane/ethylbenzene LithiuM diisopropylaMide solution 2.0 M in THF/heptane 2-Propanamine,N-(1-methylethyl)-,lithiumsalt Lithium diisopropylamide2M sol. in THF/n-heptane/ethylbenzeneAcroSeal§3 Diisopropyllithioamine N-Lithiobis(1-methylethyl)amine N-Lithio-N,N-diisopropylamine Lithium diisopropylamide,2M sol. in THF/n-heptane/ethylbenzene Lithium diisopropylamide, 2M sol. in THF/n-heptane/ethylbenzene, AcroSeal? Lithium diidopropylamide 2.0 M Lithium Diisopropylamide,2M solution in THF Lithium diisopropylamide [2M in THF/n-heptane/ethylbenzene] Lithium diisopropylamide solution,LDA Lithium diisopropyla iisopropylamide LithiuM DiisopropylaMide (LDA), 2M in THF/Heptane/Ethylbenzene LithiuM DiisopropylaMide (LDA), 2M in THF LithiuM DiisopropylaMide (ca. 20% in Tetrahydrofuran/Ethylbenzene/Heptane, ca. 1.5Mol/L) LithiuM diisopropylaMide, 2M in THF LithiuM DiisopropylaMide (LDA), 2M in THF/Hexane Lithium diisopropylamide, 2.0 M solution in THF/n-heptane/ethylbenzene (22%/35%/14%), J&KSeal DIIS Lithiodiisopropylamine Lithium diisopropylamide, 2.0 M solution in THF/n-heptane/ethylbenzene (22%/35%/14%), J& Kseal,reagent grade Lithium diisopropylamide ISO 9001:2015 REACH Lithiodiisopropylamide DISCONTINUED Lithium Diisopropylamide 2.0M In THF / 0.7M In MTBE Lithium dilsopropylamide LITHIUM DIISOPROPYLAMINE LDA lithium diisopropylamide (LDA)