diisobutylaluminium hydride CAS 1191-15-7, diisobutylaluminium hydride, CAS 1191-15-7
Diisobutylaluminium-Hydride-CAS-1191-15-7 Selective reduction: By regulating the temperature (-78°C to 70°C), highly selective reduction of functional groups can be achieved.
1191-15-7
C8H19Al
142.22
214-729-9
CAS | 1191-15-7 |
Molecular formula | C8H19Al |
Molecular weight | 142.22 |
EIENCS | 214-729-9 |
Form | Solution |
Melting point | -70 °C |
boling point | 65 °C |
Density | 1.23 g/mL at 25 °C |
Solubility | Miscible with organic solvents. |
PKA | / |
Color | Clear |
Storage temp | 2-8°C |
Restoration characteristics:
Selective reduction: By regulating the temperature (-78°C to 70°C), highly selective reduction of functional groups can be achieved.
Ester/lactone → Aldehyde/hemiacetal (low temperature, partial reduction);
Nitrile → aldehyde (hydrolyzed by imine intermediate)
Ketone/carboxylic acid → Alcohol (completely reduced).
Hydroalumination reaction: It undergoes cis-addition with alkynes to form an alkenyl aluminum intermediate, which is used in subsequent halogenation, carbonylation and other derivative reactions.
Stability and Danger:
Highly flammable (flash point 40°F/4°C), reacts violently with water to release hydrogen gas;
Strong corrosiveness: Can cause severe skin burns and eye damage (GHS label: ⚠️ Hazard, H314);
Air sensitive: It should be operated without water or oxygen and stored in an inert gas environment (such as argon).
Organic synthesis reducing agent
Partial reduction of esters/lactones: Converting esters to aldehydes at low temperatures (superior to the traditional reduction-oxidation route);
The reduction of nitriles to aldehydes: A key step in the synthesis of drug intermediates (such as the anti-cancer drug eribrine mesylate);
Epoxy isomerization: generating allyl alcohol compounds.
Industrial Catalysis and Materials
Polymer catalyst: Promotes the synthesis of polyolefins;
Synthesis of fine chemicals: such as citronellol and polyenal fragrances.
Drug research and development
It is used in the coupling reaction of antiviral drugs (such as Paxlovid intermediates) and anti-cancer drugs (eribrine).
Protective measures:
Operating requirements: Wear chemical protective gloves, goggles and a gas mask in the fume hood.
Leakage treatment: Adsorb with sand and soil. Do not rinse with water (to avoid hydrogen explosion).
Post-processing steps (refer to the standard process) :
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1. Dilute the ether and cool to 0°C;
2. Slowly add 0.04 times the volume of water;
3. Add 0.04 times the volume of 15% NaOH solution;
4. Heat to room temperature and stir for 15 minutes;
5. Filtration and desalination (anhydrous MgSO₄ as an auxiliary).
Storage conditions:
Store in a light-proof sealed container at -20°C to 8°C (argon gas protection is recommended).
Keep away from oxidants, acids and humid environments.