N-HEXYLLITHIUM Chemical Properties

Melting point:

69.00°C

Boiling point:

69 °C

Density 

0.708 g/mL at 25 °C

vapor pressure 

26.9-39.3hPa at 20-35℃

Flash point:

16 °F

storage temp. 

2-8°C

color 

yellow-brown

Sensitive 

Moisture Sensitive

BRN 

3600261

Stability:

Stable, but highly flammable. Reacts violently with water, releasing flammable gas. May spontaneously inflame in air. Moisture and air sensitive. Incompatible with water, alcohols, halocarbons.

InChI

InChI=1S/C6H13.Li/c1-3-5-6-4-2;/h1,3-6H2,2H3;

InChIKey

RMKNFFPDYCVCDI-UHFFFAOYSA-N

SMILES

C(CC[Li])CCC

EPA Substance Registry System

Lithium, hexyl- (21369-64-2)

Safety Information

Hazard Codes 

F,Xn,N,C

Risk Statements 

11-14/15-17-35-48/20-51/53-62-65-67

Safety Statements 

26-30-36/37/39-43-45-61-62-16-6

RIDADR 

UN 3394 4.2/PG 1

WGK Germany 

2

F 

10-23

TSCA 

TSCA listed

HazardClass 

4.3

PackingGroup 

I

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-HEXYLLITHIUM Usage And Synthesis

Description

n-Hexyllithium [21369-64-2], C6H13Li, Mr 92.11, r 0.766 g/cm3 is a pyrophoric colorless and viscous liquid in the neat state. It is commercially available as a 33 % solution in technical-grade hexane. Its reactivity resembles that of n-butyllithium and it can thus principally be used for the same applications. An advantage is that it does not form gaseous byproducts in deprotonation reactions and on hydrolysis, but liquid hexane instead.

Chemical Properties

often supplied as a deep yellow solution (ca 2M) in hexane. n-Hexyllithium is soluble at all concentrations in aliphatic and aromatic hydrocarbons and reacts exothermically with water and protic solvents.

Uses

n-Hexyllithium could be used as alkylating agent for various functional groups; metalating agent of aryl and heteroaryl ring systems; slightly less reactive than n-butyllithium.

Synthesis

Lithium n-hexyl preparation is as follows: argon protection, to the 500L reactor into the 250L white oil, 21kg lithium flakes, slow stirring temperature to 180 ??, stirring 0.5h, accelerate the stirring speed of the reactor to 130 rpm, 180 ?? stirring 1h, open the cooled to room temperature, pressure filtration to remove the white oil, n-hexane is transferred to the washing kettle, rinsed for 2-3 times, to obtain a relatively homogeneous lithium metal form (lithium sand). Under the protection of argon, add 20kg of n-hexane to 500L reactor, put in 7kg of lithium sand and 58g of L-proline under the condition of keeping argon released from the kettle, seal the lid and keep the positive pressure, open the venting valve to keep the pressure in balance, add 80kg of n-hexane to the reactor, slowly turn on the stirring; warm up the temperature to 55 ??, open the balancing valve, add 60kg of chlorinated n-hexane dropwise, and control the temperature of the reactor around 53-55 ??; control the reaction kettle temperature around 53-55 ??; control the reaction kettle. Control the temperature of reaction kettle at about 53-55??; control the speed of reaction kettle at 130 rpm. After dropping, start to keep warm, keep warm for about 8 hours, cool down to room temperature and stand, filter with a sand plate funnel, the reactor and the filtrate were washed with n-hexane, and the n-hexyl lithium product with a concentration of 1.9M was obtained as 233L (89% yield).

Precautions

n-Hexyllithium should be handled as n-Butyllithium; store in a cool, dry place in a tightly sealed container under an inert atmosphere.

N-HEXYLLITHIUM(21369-64-2)Related Product Information

• Methyllithium
• n-Butyllithium
• LITHIUM METHOXIDE
• ISOBUTYLLITHIUM
• tert-Butyllithium
• Lithium bis(trimethylsilyl)amide
• SEC-BUTYLLITHIUM
• Butyldi-1-adamantylphosphine
• Lithium chloride
• (TRIMETHYLSILYL)METHYLLITHIUM
• Lithium diisopropylamide
• Lithium hexamethyldisilazide
• Butylamine
• n-Butylboronic acid
• Heptanoyl chloride
• Hexane
• Valeric acid
• Ethyl Hexanoate