DIETHYLALUMINUM CYANIDE SOLUTION

Base Information

• Chemical Name: DIETHYLALUMINUM CYANIDE SOLUTION
• CAS No.: 5804-85-3
• Molecular Formula: C5H10 Al N
• Molecular Weight: 111.123
• European Community (EC) Number: 227-359-8
• DSSTox Substance ID: DTXSID301046472
• Wikidata: Q5275147
• Wikipedia: Diethylaluminium_cyanide
• Mol file: 5804-85-3.mol

Synonyms:Aluminum,(cyano-C)diethyl-; Aluminum, cyanodiethyl- (7CI,8CI); Cyanodiethylalane;Cyanodiethylaluminum; Diethylaluminum cyanide

Chemical Property of DIETHYLALUMINUM CYANIDE SOLUTION

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 23.79000
• Density: g/cm³
• LogP: 2.03508
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 111.0628627
• Heavy Atom Count: 7
• Complexity: 77.3

Purity/Quality:

98%Min ^*data from raw suppliers

Diethylaluminum cyanide solution 1.0M in toluene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T+,N
• Hazard Codes: F,T+,N
• Statements: 11-26/27/28-32-38-48/20-50/53-63-65-67
• Safety Statements: 36/37-45-60-61-62-28-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC[Al](CC)C#N
• Uses: DIETHYLALUMINUM CYANIDE SOLUTION Reagents used to hydrocyanate side chain ketones directed by aryl sulfinyl groups.1

Technology Process of DIETHYLALUMINUM CYANIDE SOLUTION

There total 1 articles about DIETHYLALUMINUM CYANIDE SOLUTION which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ diethylaluminium cyanide (5804-85-3)

Guidance literature:

DOI:10.1016/S0022-328X(00)87664-0 DOI:10.1039/j19700002675 DOI:10.1016/S0040-4039(00)76271-X DOI:10.1021/ja00768a038

Reference yield: 96.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + diethylaluminium cyanide (5804-85-3) → isophoronenitrile (7027-11-4)

Guidance literature:

In hexane; toluene; at 15 - 20 ℃; for 5h;

Reference yield: 85.0%

isoquinoline (119-65-3) + diethylaluminium cyanide (5804-85-3) + benzoyl chloride (98-88-4) → 2-benzoyl-1-cyano-1,2-dihydroisoquinoline (844-25-7,55839-33-3)

Guidance literature:

In dichloromethane; toluene; Product distribution; various ratios of reactants and reaction times; other heterocyclic bases and acid halides;

Downstream raw materials:

3-trimethylsiloxy-2-cyclohexene-1-carbonitrile

1,5,5-Trimethyl-3-trimethylsilanyloxy-cyclohex-2-enecarbonitrile

6,6-Dimethyl-3-trimethylsilanyloxy-cyclohex-2-enecarbonitrile

3-cyano-2-cyclohexenone

Refernces

A New General Method To Obtain Chiral 2-Alkylglycidyl Acid Derivatives: Synthesis of Methyl (R)-(+)-Palmoxirate

10.1021/jo00082a008

The research focuses on developing a new general method for synthesizing optically pure 2-alkylglycidic acid derivatives, specifically targeting the synthesis of (R)-(+)-palmoxirate, a potent hypoglycemic agent. The study utilizes a sequence involving the asymmetric hydrocyanation of ketones with α-sulfinyl ketones and Et2AlCN to obtain diastereomerically pure cyanohydrins, which are then transformed into 2-alkylglycidic acid derivatives through hydrolysis and treatment with Me30+BF4- and NaHCO3. The process yields high enantioselectivity (ee >97%) and has been successfully applied to synthesize the optically pure (R)-(+)-palmoxirate, offering a more efficient method compared to previous chemical and enzymatic approaches. Key chemicals used in the process include Et2AlCN, Me30+BF4-, NaHCO3, and various α-sulfinyl ketones and cyanohydrins. The study concludes that this method can be extended to prepare other structurally similar compounds and is currently being used for the synthesis of trisubstituted oxiranes.