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Lithium diisopropylamide

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Company Name: Beijing Cooperate Pharmaceutical Co.,Ltd
Tel: 010-60279497
Email: sales01@cooperate-pharm.com
Products Intro: Product Name:Lithium diisopropylamide
CAS:4111-54-0
Purity:98% Package:100G;1KG;5KG;10KG;25KG;50KG;100KG
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: 0371-55170693
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Products Intro: Product Name:4111-54-0
CAS:4111-54-0
Purity:0.99 Package:25KG,5KG;1KG;500G
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008615858145714
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Products Intro: Product Name:Lithium diisopropylamide
CAS:4111-54-0
Company Name: Shanghai Zheyan Biotech Co., Ltd.
Tel: 18017610038
Email: zheyansh@163.com
Products Intro: Product Name:Lithium diisopropylamide
CAS:4111-54-0
Purity:2.0 M in THF Package:100ml
Company Name: career henan chemical co
Tel: +86-371-86658258
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Products Intro: Product Name:Lithium diisopropylamide
CAS:4111-54-0
Purity:99% Package:1kg;1USD

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  • What is Lithium diisopropylamide?
  • Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula [(CH3)2CH]2NLi. It is us....
  • Feb 22,2021
Lithium diisopropylamide Basic information
Product Name:Lithium diisopropylamide
Synonyms:ithium diisopropyL;LITHIUM DIISOPROPYLAMIDE THF COMPLEX;LITHIUM DIISOPROPYLAMINE;LITHIUM DIISOPROPYLAMIDE;LDA THF COMPLEX;LDA;DIISOPROPYLAMINOLITHIUM;Lithium diisopropylamide solution
CAS:4111-54-0
MF:C6H16LiN
MW:109.14
EINECS:223-893-0
Product Categories:Classes of Metal Compounds;Organic-metal salt;Li (Lithium) Compounds;Typical Metal Compounds
Mol File:4111-54-0.mol
Lithium diisopropylamide Structure
Lithium diisopropylamide Chemical Properties
Melting point decomposes [MER06]
Boiling point 65 °C
density 0.864 g/mL at 25 °C (lit.)
vapor density >1 (vs air)
Fp 91 °F
storage temp. 2-8°C
form liquid
color brown
Water Solubility decomposes
Sensitive Air & Moisture Sensitive
Merck 14,3196
BRN 3655042
CAS DataBase Reference4111-54-0(CAS DataBase Reference)
EPA Substance Registry System2-Propanamine, N-(1-methylethyl)-, lithium salt (4111-54-0)
Safety Information
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
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Lithium diisopropylamide Usage And Synthesis
Chemical Propertiesdark yellow to orange or dark red-brown solution
Chemical PropertiesLithium 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.
UsesLithium 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.
UsespH adjuster in colognes and toilet waters. In organic synthesis, particularly, the lithium salt.
Chemical SynthesisLithium 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)
Purification MethodsIt 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.]
Tag:Lithium diisopropylamide(4111-54-0) Related Product Information
Isopropylamine Lithium diisopropylamide 1-Methyl-2-pyrrolidinone N,N'-Diisopropylcarbodiimide Lithium chloride Diisopropylamine N,N-Diisopropylethylamine Lithium oxide Lithium bis(trimethylsilyl)amide Lithium diisopropylamide mono(tetrahydrofuran) Lithium diisopropylamide mono(tetrahydrofuran) complex solution LITHIUM DIETHYLAMIDE LITHIUM TETRAMETHYLPIPERIDIDE LITHIUM DICYCLOHEXYLAMIDE LITHIUM DIMETHYLAMIDE Lithium Lithium amide DIISOPROPYL ZINC 1.0M SOLUTION IN TOLU&