137203-34-0

Basic information

• Product Name: Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum)
• Synonyms: Bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct;Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum);Bis(trimethylaluminum)-DABCO(R) adduct;DABAL-Me3;DABAL-trimethylaluminum;Triethylenediaminine bis(trimethylaluminum);Bis(trimethylaluminium)-1,4-diazabicyclo-[2.2.2]octane adduct (DABAL-Me3)
• CAS NO: 137203-34-0
• Molecular Formula: C₁₂H₃₀Al₂N₂
• Molecular Weight: 256.343076
• Product Categories: DABAL - Me3;Greener Alternatives and Technologies;Greener Alternatives: Reagents;Chemical Synthesis;Organoaluminum;Organometallic Reagents
• Mol File: 137203-34-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: >250 °C
• Flash Point: 23°C (73°F)
• Appearance: /
• Storage Temp.: Hygroscopic, Room Temperature, Under inert atmosphere
• Solubility: Benzene (Slightly), DMSO (Slightly)
• Stability: Hygroscopic, Moisture Sensitive, Unstable in Aqueous Solution
• CAS DataBase Reference: Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum)(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum)(137203-34-0)
• EPA Substance Registry System: Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum)(137203-34-0)

Safety Data

• Hazard Codes: F,Xn
• Statements: 14-15-22-36/37/38
• Safety Statements: 16-26-43
• RIDADR: UN 3395 4.3/PG 1
• WGK Germany: 3
• Hazardous Substances Data: 137203-34-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 137203-34-0 differently. You can refer to the following data:
1. Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum) is a non-pyrophoric alternative to trimethylaluminum for use in numerous reactions including methylations of aldehydes and imines, methylations of aryl and vinyl halides, conjugate addition to enones, and amide bond formation.1
2. DABAL-Me3: An Air Stable "Methyl Anion"

General Description

Product is air and moisture sensitive. Handle and store under a dry, inert atmosphere.

InChI:InChI=1/C6H12N2.6CH3.2Al/c1-2-8-5-3-7(1)4-6-8;;;;;;;;/h1-6H2;6*1H3;;/rC6H12N2.2C3H9Al/c1-2-8-5-3-7(1)4-6-8;2*1-4(2)3/h1-6H2;2*1-3H3

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 75-24-1 trimethylaluminum 

Downstream Products

• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 99493-93-3 (S)-1-(4-trifluoromethylphenyl)ethanol 
• 1737-26-4 (R)-1-[4-(trifluoromethyl)phenyl]ethan-1-ol 
• 536-50-5 (S)-1-(4-Methylphenyl)ethanol 
• 42070-92-8 (R)-1-(4-methylphenyl)ethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 99-99-0 1-methyl-4-nitrobenzene 
• 104-93-8 p-methylanizole 
• 91-57-6 2-Methylnaphthalene 
• 578-58-5 2-methylmethoxybenzene 
• 108-38-3 m-xylene 

Relevant articles and documents

Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins

Natural products form attractive leads for the development of chemical probes and drugs. The antibacterial lipopeptide Brabantamide A contains an unusual enol cyclocarbamate and we used this scaffold as inspiration for the synthesis of a panel of enol cyclocarbamate containing compounds. By equipping the scaffold with different groups, we identified structural features that are essential for antibacterial activity. Some of the derivatives block incorporation of hydroxycoumarin carboxylic acid-amino d-alanine into the newly synthesized peptidoglycan. Activity-based protein-profiling experiments revealed that the enol carbamates inhibit a specific subset of penicillin-binding proteins in B. subtilis and S. pneumoniae.

Remarkably stable (Me3Al)2·DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes

(Chemical Equation Presented) Weigh it out in air! The DABAL reagent (Me3Al)2·(DABCO) (DABCO = 1,4-diazabicyclo[2.2.2] octane) can be easily handled under normal laboratory conditions. Furthermore, chiral secondary alcohols can be efficiently prepared from prochiral aldehydes (see scheme; TOF = turnover frequency) by using either DABAL or AIR3 reagents (R = Me, Et). Thus, DABAL can be used as an efficient, convenient alternative to the Schumann-Blum reagent.