Synthesis of n-Butyllithium

Preparation of n-Butyllithium (n-BuLi · LiBr)

Preparation of n-Butyllithium

Preparation of n-Butyllithium

18 g (2.57 mol) lithium containing 1-3 % of sodium are flattened with a hammer to 1.5 mm thickness and subsequently cut into the flask (chips of 2 x 10 x 1.5 mm) containing 800 ml DRY diethyl ether. The ether is cooled to – 25° and the air purged with dry nitrogen or argon (2 l/min during 1-2 min). In the dropping funnel 172.7 g, (1.1 mol), of n-butyl bromide are placed and 10 g are added in one portion. After a few minutes a turbidity appears and a distinct rise of the temperature occurs. When, after about 10 min, the reaction has subsided, the remainder of the n-butyl bromide is added slowly dropwise over 1 hour period, while keeping the temperature of the mixture between -15 and -20°C. The black coating disappears almost entirely from the lithium metal which has a bright silver-like color. After the addition is complete, stirring is continued at -15°C for an additional hour. The temperature is then allowed to rise to 0° and the glow on the metal gradually disappears. The obtained solution is ten poured into the storage flask, which previously has been filled with inert gas (it is not necessary to filter off the lithium chips). During filtration under inert atmosphere a fast stream (2 to 3 l/min) nitrogen or argon is passed through the reaction flask to protect the solution against attack by oxygen. Diethyl ether is added to bring the solution to a volume of 1 litre. After gentle shaking or swirling (homogenization), the titer is  determined: this is usually close to 1 molar corresponding to a yield of 90 %.

n-Butyllithium can also be prepared from lithium chips and butyl chloride in ether, by a procedure analogous to that described above. The reaction is conveniently carried out at temperatures around + 20°C. The lithium chloride does not form a soluble complex with n-butyllithium, but precipitates, so that the supernatant solution contains little salt. After decanting the clear solution through glass-wool (to remove the excess of lithium), the salt is rinsed 3 to 5 times with small amounts of ether. These ethereal solutions are decanted and added to the main solution. Yields of at least 80 % are obtained.

Preparative Polar Organometallic Chemistry; Vol 1; by L. Brandsma, H. D. Verkruijsse; Springer-Verlag Berlin Heidelberg; 17-18; 1987

IUPAC Name

lithium;butane

InChI

InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/q-1;+1

InChI Key

DLEDOFVPSDKWEF-UHFFFAOYSA-N

Canonical SMILES

[Li+].CCC[CH2-]

MeSH Synonyms

bu-Li, butyllithium

Depositor-Supplied Synonyms

N-butyllithium, BUTYLLITHIUM, 109-72-8, Lithium, butyl-, Butyl lithium, n-BuLi, lithium butane, n-Butyl lithium, BuLi, Lithium-1-butanide, Butyllithium solution, lithium(1+) ion butan-1-ide, butyilithium, butyl-lithium, n-butyllithiurn, n- butyllithium, n-butyl-lithium, 1-butyllithium, 1-lithiobutane, LiBu, normal-butyllithium, normal-butyl lithium, lithium butan-1-ide, n-Butyllithium solution, AC1L1UDX, U – Chromosorb® W, UNII-09W9A6B8ZC, KSC175G2B, 20159_ALDRICH, 20164_ALDRICH, 09W9A6B8ZC, 186171_ALDRICH, 230707_ALDRICH, 230715_ALDRICH, 302104_ALDRICH, 302120_ALDRICH, Jsp000761, 20159_FLUKA, 20164_FLUKA, CHEBI:51469, CTK0H5320, MolPort-001-788-019, MZRVEZGGRBJDDB-UHFFFAOYSA-N, Butyl lithium; Lithium-1-butanide, 1.6 M N-Butyl lithium in hexanes, EBD25912, EINECS 203-698-7, ANW-16085, MFCD00009414, AKOS000121343, AKOS015915366, RP18271, RTR-002081, AN-42956, LP067012, OR012018, SC-16375, n-Butyllithium, 2.5M solution in hexanes, AB1002417, KB-301869, TR-002081, B0396, FT-0082506, FT-0650696, A802078, I14-6496, 3B3-020424, 52948-61-5

Removed Synonyms

nBuLi, CID61028, CID6093364, 594-19-4, 68855-54-9, NBL

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