Name | lithium diisopropylamide |
Synonyms | LDA LDA THF COMPLEX ithium diisopropyL DIISOPROPYLAMINOLITHIUM LITHIUM DIISOPROPYLAMIDE LITHIUM DIISOPROPYLAMINE lithium diisopropylamide Lithium diisopropylazanide Lithium diisopropylamide solution lithium bis(1-methylethyl)azanide LITHIUM DIISOPROPYLAMIDE THF COMPLEX |
CAS | 4111-54-0 |
EINECS | 223-893-0 |
InChI | InChI=1/C6H15N.Li/c1-5(2)7-6(3)4;/h5-7H,1-4H3;/q;+1 |
Molecular Formula | C6H16LiN |
Molar Mass | 109.14 |
Density | 0.864 g/mL at 25 °C (lit.) |
Melting Point | decomposes [MER06] |
Boling Point | 65°C |
Flash Point | 91°F |
Water Solubility | decomposes |
Vapor Density | >1 (vs air) |
Appearance | liquid |
Color | brown |
Merck | 14,3196 |
BRN | 3655042 |
Storage Condition | 2-8°C |
Sensitive | Air & Moisture Sensitive |
Risk Codes | R14 - Reacts violently with water R17 - Spontaneously flammable in air R34 - Causes burns R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R35 - Causes severe burns R19 - May form explosive peroxides R15 - Contact with water liberates extremely flammable gases R11 - Highly Flammable R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R14/15 - R10 - Flammable R40 - Limited evidence of a carcinogenic effect R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R62 - Possible risk of impaired fertility R63 - Possible risk of harm to the unborn child R37 - Irritating to the respiratory system R48/20 - |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.) S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S8 - Keep container dry. S16 - Keep away from sources of ignition. S23 - Do not breathe vapour. S33 - Take precautionary measures against static discharges. S27 - Take off immediately all contaminated clothing. |
UN IDs | UN 3399 4.3/PG 2 |
WGK Germany | 3 |
FLUKA BRAND F CODES | 1-10 |
TSCA | Yes |
HS Code | 29211990 |
Hazard Class | 4.2 |
Packing Group | I |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Application | Lithium diisopropylamide is usually used as a base in organic chemistry to deprotonate hydrocarbons. Lithium diisopropylamide is widely used because it is soluble in non-polar organic solvents. Lithium diisopropylamide is a very widely used non-nucleophilic strong base reagent in organic synthesis. pKa = 35.7 in tetrahydrofuran. In the field of synthetic chemistry, it is often used as a base to deprotonate hydrocarbons, and sometimes used to generate carbanions and enol anions. |
Preparation of lithium diisopropylamide | It can be prepared by the reaction of metal lithium with diisopropylamine, or by the reaction of diisopropylamine with butyl lithium or methyl lithium. The normal color is similar to that of n-butyl lithium solution. It is very light yellow and transparent. If butyl lithium is impure or moisture and oxygen enter during the preparation process, it will oxidize and decompose into lithium oxides or other things, which will produce precipitation and discoloration. |
Uses | Lithium diisopropylamide is widely used in metallized alkaline reagents, and it is also used in large sterically hindered non-nucleophilic strong alkali reagents, etc. Very famous large sterically hindered strong alkali, used to form carbanion. Lithium diisopropylamide is widely used in metallized alkaline reagents, and it is also used in non-nucleophilic strong alkali reagents with large steric hindrance. |