DBU

DBU Basic information
Product Name:DBU
Synonyms:1,5-DIAZABICYCLO(5,4,0)UNDEC-5-ENE;1,8-DIAZABICYCLO[5,4,0]-7-UNDECENE;1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE;1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE (1,5-5);1,8-DIAZABICYCLO(5,4,0)UNDECENE-7;1,8-DIAZEBICYCLO[5.4.0]UNDEC-7-ENE;1,8-Diazabicyclo[5.4.0]undecane-7-ene;1,8-Diazabicyclo(5 x 4 x 0)undec-7-ene
CAS:6674-22-2
MF:C9H16N2
MW:152.24
EINECS:229-713-7
Product Categories:pharmacetical;Pyridines;Other Reagents;Biochemistry;Reagents for Oligosaccharide Synthesis;Biochemics;OLED materials,pharm chemical,electronic;A clear, light yellow liquid of relatively low volatility. It has only a slight ammonia-like odor, is miscible with water and is soluble in most organic solvents.;pharmaceutical raw material;Organic intermediates;bc0001
Mol File:6674-22-2.mol
DBU Structure
DBU Chemical Properties
Melting point -70 °C
Boiling point 80-83 °C0.6 mm Hg(lit.)
density 1.019 g/mL at 20 °C(lit.)
vapor pressure 5.3 mm Hg ( 37.7 °C)
refractive index n20/D 1.523
Fp >230 °F
storage temp. Store below +30°C.
solubility soluble
form Liquid
pka13.28±0.20(Predicted)
color Clear colorless to light yellow
OdorUnpleasant
PH Range12.8 at 10 g/l at 20 °C
PH12.8 (10g/l, H2O, 20℃)
explosive limit1.1-6.5%(V)
Water Solubility soluble
Sensitive Air Sensitive
BRN 508906
Stability:Stable. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
InChIKeyGQHTUMJGOHRCHB-UHFFFAOYSA-N
CAS DataBase Reference6674-22-2(CAS DataBase Reference)
NIST Chemistry Reference1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2)
EPA Substance Registry SystemPyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2)
Safety Information
Hazard Codes C,F
Risk Statements 22-34-52/53-35-40-37-19-11-67
Safety Statements 26-36/37/39-45-61-27-16
RIDADR UN 3267 8/PG 2
WGK Germany 2
34
Autoignition Temperature260 °C
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29339930
ToxicityLD50 orally in Rabbit: 215 - 681 mg/kg
MSDS Information
ProviderLanguage
1,8-Diazabicyclo[5.4.0]undec-7-ene English
ACROS English
SigmaAldrich English
ALFA English
DBU Usage And Synthesis
DescriptionDBU is a bicyclic amidine base. It is non-nucleophilic, sterically hindered, tertiary amine base in organic chemistry. It is reported to be superior to amine catalyst in Baylis-Hillman reaction.It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.
Chemical PropertiesColorless to yellow liquid
OccurrenceAlthough all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.The biosynthesis of DBU has been proposed to begin with 1,6-hexanedial and 1,3-diaminopropane. 
UsesDBU may be used:
  1. as catalyst for carboxylic acid esterification with dimethyl carbonate
  2. in the synthesis of duocarmycin and CC-1065 analogs
  3. as catalyst in aza-Michael addition and Knovenegal condensation reaction
  4. as base for dehalogenation of halogenated Diels-Alder adducts and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3)
  5. in a new synthesis of the ABCD ring system of Camptothecin
  6. DBU may be used as an catalyst for the dissolution and activation of cellulose by a reversible reaction of its hydroxyl groups with carbon dioxide. This dissolved cellulose system can be derivatized to form cellulose mixed esters.
  7. Used in a new synthesis of the ABCD ring system of Camptothecin.
UsesDBU is used in organic synthesis as a catalyst, a complexing ligand, and a non-nucleophilic base. It is used as a protecting agent for the synthesis of cephalosporin and as a catalyst for polyurethane.
General DescriptionWe are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
Flammability and ExplosibilityNonflammable
Synthesis The synthesis of DBU is as follows:As a base, sodium hydroxide was used at a concentration of 25% by weight and 2.3 times molar equivalent. A stirrer was placed in a 100 mL screw tube, and 11.5 g (50 mmol) of DBU hydrochloride, 8.5 g of toluene and 18.5 g (116 mmol) of 25% sodium hydroxide aqueous solution were charged at room temperature. It was placed on a magnetic stirrer and mixed for 1 hour with stirring. The mixture was separated with a 100 mL separatory funnel to obtain 18.8 g of the upper layer containing DBU and 18.4 g of the lower layer of the aqueous layer. The upper layer portion was analyzed by gas chromatography and contained 31.9% by weight of DBU, and the yield was 6.0 g (39.4 mmol) in a yield of 78.8%.

synthesis of DBU

Purification MethodsFractionally distil DBU under vacuum. Also purify it by chromatography on Kieselgel and eluting with CHCl3/EtOH/25% aqueous NH3 (15:5:2) and checking by IR and MS. [Oediger et al. Chem Ber 99 2012 1962, Angew Chem, Int Ed Engl 6 76 1967, Guggisberg et al. Helv Chim Acta 61 1057 1978, Beilstein 23/5 V 271.]
Hexamethylene Diisocyanate Tosyl azide 1,8-Diazabicyclo[5.4.0]undec-7-ene formaldehyde/phenol copolymer 1,8-DIAZABICYCLO[5.4.0] UNDEC-7-ENE (67.2.6) PHTHALIMIDE 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE SALT 6-(DIBUTYLAMINO)-1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE (POLYCAT DBU CATALYST) 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE, COMPOUND WITH PHENOL (1:1) 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE HYDROTRIBROMIDE 1 8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE POLY& DBU(1,8-Diazabicyclo[5,4,0]-undec-7-ene) 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE, COMPOUND WITH 2-ETHYLHEXANOIC ACID (1:1),1,8-Diazabicyclo[5.4.0]undec-7-ene 2-ethylhexanoate 1,8-Diazabicyclo[5.4.0]undec-7-ene, polymer-bound,DIAZABICYCLO[5.4.0]UNDEC-7-ENE, POLYMER-BOUND 1-NONENE DBU 8-Benzyl-1,8-diazabicyclo[5.4.0]undec-7-ene tetraphenylborate BENZYL-DBU-CHLORIDE 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE, COMPOUND WITH P-TOLUENESULFONIC ACID (1:1)

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