PRODUCT IDENTIFICATION

6674-22-2

2933.59.9590

SMILES

N1=C2N(CCCCC2)CCC1

CLASSIFICATION

Amine, Strong Base

PHYSICAL AND CHEMICAL PROPERTIES

1.018

260 C

112 C

GENERAL DESCRIPTION & EXTERNAL LINKS

DBU, tertiary amine compound, is used as a catalyst for polyurethane. It has strong catalyst effect for the reactions of alicyclic and aliphatic isocyanates which are less active than aromatic isocyanates. It is used as a dehydrohalogenation agent and a curing agent for epoxy. It is used as a protecting agent for the synthesis of cephalosprines. 2,2'-Diazabicyclo[2.2.2]octane (triethylene diamine) has similar applications. Recently DBU is used in fullerene purification in a form of mixture with trimethylbenzene. DBU reacts to C₇₀ and higher fullerenes but not to C₆₀ fullerenes. DBU is an amidine compound which has amidino functional group, -HN=CNH₂. As a prefix (amidino-). The prefix amido- is for the presence of the radical -NH₂ along with the radical CO. Diamidine is a molecule that has two amidine groups. Diminazene (CAS #: 536-71-0) is an example. Diminazene aceturate is used as  a veterinary antibacterial and antiprotozoal.

Amidines and guanidines, the compound NH=C(NH₂)₂, are strongly basic reagents. Bases activation of deprotonation is the first step in the synthesis. The strength of basicity, nucleophilicity, steric hindrance or solubility are the factors to select reagents for the best results in the chemical reactions such as alkylation, tautomerization, dehydrohalogenation, michael-addition, esterification, saponification, acylation, silylations, aldol-condensation, eliminations, and cyclization. The order of basicity strength of some amines are; TBD > MTBD > DBU > DBN > TMG > Quinuclidine > TMP, Pempidine > Triethylamine > TED > Tributylamine > Collidine > Lutidine

• TBD: 1,5,7-Triazabicyclo(4.4.0)dec-5-ene; 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a] pyrimidine, CAS #: 5807-14-7
• MTBD :7-Methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene;1,3,4,6,7,8-Hexahydro-1- methyl-2H-pyrimido [1,2-a]pyrimidine, CAS #: 84030-20-6
• DBU: 1,8-Diazabicyclo[5.4.0]undec-7-ene; 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a] azepine, CAS #: 6674-22-2
• DBN: 1,5-Diazabicyclo[4.3.0]non-5-ene, CAS #: 3001-72-7
• TMG: 1,1,3,3-Tetramethylguanidine; N,N,N',N'-Tetramethylguanidine, CAS #: 80-70-6
• Quinuclidine: 1-Azabicyclo[2.2.2]octane, CAS #: 100-76-5
• TMP: 2,2,6,6-Tetramethylpiperidine, CAS #: 768-66-1
• Pempidine: 1,2,2,6,6-Pentamethylpiperidine, CAS #: 79-55-0
• TED: 1,4-Diazabicyclo[2.2.2]octan; Triethylenediamine, CAS #: 280-57-9
• Collidine: Trimethylpyridine, CAS #: 108-75-8 (2,4,6- Isomer)
• Lutidine: Dimethylpyridine, CAS #: 108-48-5 (2,6- Isomer)

Wikipedia Linking: http://en.wikipedia.org/wiki/1,8-Diazabicycloundec-7-ene

http://www.sigmaaldrich.com
Halogenated Diels-Alder adducts were dehydrohalogenated with this base, and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto¡Çs reagent (CH₃Cu · BF₃). Used in a new synthesis of the ABCD ring system of Camptothecin.

Amidine base used for dehydrohalogenation reactions to olefins; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides; Alkylation and acylation of active methylene compounds.

APPEARANCE

99.0% min

COLOR, APHA

300 max