Lithium diisopropylamide

한글명:Lithium diisopropylamide

카스 번호4111-54-0

상품명:Lithium diisopropylamide

CBNumberCB6677718

분자식C6H16LiN

포뮬러 무게109.14

MOL 파일4111-54-0.mol

화학적 성질

녹는점	decomposes [MER06]
끓는 점	65 °C
밀도	0.864 g/mL at 25 °C (lit.)
증기 밀도	>1 (vs air)
인화점	91 °F
저장 조건	2-8°C
용해도	soluble in ethyl ether; insoluble in hydrocarbon solvents
물리적 상태	액체
색상	갈색
수용성	물에서 분해되다
감도	Air & Moisture Sensitive
Merck	14,3196
BRN	3655042
CAS 데이터베이스	4111-54-0(CAS DataBase Reference)
EPA	2-Propanamine, N-(1-methylethyl)-, lithium salt (4111-54-0)

위험 및 안전 성명

위험품 표기	C,N,F
위험 카페고리 넘버	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
안전지침서	26-36/37/39-43-45-60-61-62-8-16-23-33-27
유엔번호(UN No.)	UN 3399 4.3/PG 2
WGK 독일	3
F 고인화성물질	1-10
TSCA	Yes
위험 등급	4.2
포장분류	I
HS 번호	29211990

그림문자(GHS)

Lithium diisopropylamide 화학적 특성, 용도, 생산

화학적 성질
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.
용도
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.
일반 설명
This material is in a solution of THF/Hexanes (ca. 1:7 ratio, respectively)
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.]

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