1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE

PRODUCT IDENTIFICATION

CAS NO.

6674-22-2

1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE

EINECS NO. 229-713-7
FORMULA C9H16N2
MOL WT. 152.24
H.S. CODE

2933.59.9590

TOXICITY  
SYNONYMS DBU; 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine;
2,3,4,6,7,8,9,10-Octahydropyrimido(1,2-alpha)azepine; 1,8-Diazabicyclo[5.4.0]undec-7-en (German); 1,8-diazabiciclo[5.4.0]undec-7-eno; 1,8-diazabicyclo[5.4.0]undéc-7-ene;

SMILES

N1=C2N(CCCCC2)CCC1

CLASSIFICATION

Amine, Strong Base

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE light yellow liquid
MELTING POINT -78 C
BOILING POINT 100 C
SPECIFIC GRAVITY

1.018

SOLUBILITY IN WATER soluble (4920 mg/l at 25 C)
AUTOIGNITION

260 C

pKa (Dissociation Constant at 20 C)
log Pow 1.38 (Octanol-water)
VAPOR PRESSURE 0.055 (mmHg at 25 C)
HENRY'S LAW 1.93E-06 (atm-m3/mole at 25 C)
OH RATE 3.56E-11 (cm3/molecule-sec at 25 C Atmospheric )
pH  
VAPOR DENSITY  
NFPA RATINGS Health: 3; Flammability: 1; Reactivity: 0
FLASH POINT

112 C

STABILITY Stable under orginary conditions

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 (CH
3Cu · 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.

SALES SPECIFICATION

APPEARANCE

light yellow liquid
ASSAY (G.C)

99.0% min

COLOR, APHA

300 max

MOISTURE (K.F) 0.5% max
TRANSPORTATION
PACKING 200kgs in Drum
HAZARD CLASS 8
UN NO. 1760
OTHER INFORMATION
Hazard Symbols: C, Risk Phrases: 22/34, Safety Phrases: 24/25