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DBU

Product Name
DBU
CAS No.
6674-22-2
Chemical Name
DBU
Synonyms
DBU;2,3,4,6,7,8,9,10-OCTAHYDROPYRIMIDO[1,2-A]AZEPINE;Diazabicycloundecene;1,8-DIAZABICYCLO[5,4,0]-7-UNDECENE;1,5-DIAZABICYCLO(5,4,0)UNDEC-5-ENE;Polycat DBU;1,8-DiazabicycL;1,8-DIAZABICYCLO(5,4,0)UNDECENE-7;1,8-Diazabicyclo(5.4.0)undec-7-en;1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE (DBU)
CBNumber
CB6368038
Molecular Formula
C9H16N2
Formula Weight
152.24
MOL File
6674-22-2.mol
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DBU Property

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
Flash point:
>230 °F
storage temp. 
Store below +30°C.
solubility 
soluble
form 
Liquid
pka
13.28±0.20(Predicted)
color 
Clear colorless to light yellow
Odor
Unpleasant
PH Range
12.8 at 10 g/l at 20 °C
PH
12.8 (10g/l, H2O, 20℃)
explosive limit
1.1-6.5%(V)
Water Solubility 
soluble
Sensitive 
Air Sensitive
BRN 
508906
Stability:
Stable. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
InChIKey
GQHTUMJGOHRCHB-UHFFFAOYSA-N
CAS DataBase Reference
6674-22-2(CAS DataBase Reference)
NIST Chemistry Reference
1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2)
EPA Substance Registry System
Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2)
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Safety

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
F 
34
Autoignition Temperature
260 °C
TSCA 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29339930
Toxicity
LD50 orally in Rabbit: 215 - 681 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H290May be corrosive to metals

H301Toxic if swalloed

H314Causes severe skin burns and eye damage

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P234Keep only in original container.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.03282
Product name
1,8-Diazabicyclo[5.4.0]undec-7-ene
Purity
for synthesis
Packaging
25mL
Price
$35.9
Updated
2024/03/01
Sigma-Aldrich
Product number
8.03282
Product name
1,8-Diazabicyclo[5.4.0]undec-7-ene
Purity
for synthesis
Packaging
100mL
Price
$102
Updated
2024/03/01
Sigma-Aldrich
Product number
8.03282
Product name
1,8-Diazabicyclo[5.4.0]undec-7-ene
Purity
for synthesis
Packaging
2.5L
Price
$300
Updated
2024/03/01
Sigma-Aldrich
Product number
33482
Product name
1,8-Diazabicyclo[5.4.0]undec-7-ene
Purity
puriss., ≥99.0% (GC)
Packaging
50mL
Price
$71.7
Updated
2024/03/01
Sigma-Aldrich
Product number
33482
Product name
1,8-Diazabicyclo[5.4.0]undec-7-ene
Purity
puriss., ≥99.0% (GC)
Packaging
250ML
Price
$208
Updated
2024/03/01
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DBU Chemical Properties,Usage,Production

Description

DBU 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 Properties

Colorless to yellow liquid

Occurrence

Although 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. 

Uses

DBU may be used:

  2. as catalyst for carboxylic acid esterification with dimethyl carbonate
  4. in the synthesis of duocarmycin and CC-1065 analogs
  6. as catalyst in aza-Michael addition and Knovenegal condensation reaction
  8. 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)
  10. in a new synthesis of the ABCD ring system of Camptothecin
  12. 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.
  14. Used in a new synthesis of the ABCD ring system of Camptothecin.

Uses

DBU 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 Description

We 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 Explosibility

Non flammable

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%.

Purification Methods

Fractionally 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.]

DBU Preparation Products And Raw materials

Raw materials

Preparation Products

2-Oxetanone 4H-AMINO-6-BROMO-2,3-DIHYDROTHIOCHROMEN-1,1-DIOXIDE 5-Phenyl-1,3-oxazole-4-carboxylic acid Fmoc-8-amino-3,6-dioxaoctanoic acid 1-Isoquinolinecarbonitrile 5-AMINOINDOLE HYDROCHLORIDE Di-tert-butyl dicarbonate 4-CYANOSTYRENE 4-NITROSTYRENE 6-Nitroindole 5-PHENYL-1,3-OXAZOLE-4-CARBONYL CHLORIDE (1R,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID 6-Aminoindole 9-VINYLANTHRACENE METSULFURON METHYL
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View Lastest Price from DBU manufacturers

Jinan Finer Chemical Co., Ltd
Product
1,8-Diazabicyclo[5.4.0]undec-7-ene 6674-22-2
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
500mt
Release date
2022-01-25
ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Baloxavir Impurity 44
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
0.98
Supply Ability
10g
Release date
2024-04-09
ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Baloxavir Impurity 44
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
0.98
Supply Ability
10g
Release date
2024-04-09

6674-22-2, DBURelated Search:

Tosyl azide Hexamethylene Diisocyanate 1-NONENE DBU 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, COMPOUND WITH PHENOL (1:1) 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE, COMPOUND WITH P-TOLUENESULFONIC ACID (1:1) 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE HYDROTRIBROMIDE BENZYL-DBU-CHLORIDE 6-(DIBUTYLAMINO)-1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE PHTHALIMIDE 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE SALT 1,8-Diazabicyclo[5.4.0]undec-7-ene formaldehyde/phenol copolymer 8-Benzyl-1,8-diazabicyclo[5.4.0]undec-7-ene tetraphenylborate 1,8-Diazabicyclo[5.4.0]undec-7-ene, polymer-bound,DIAZABICYCLO[5.4.0]UNDEC-7-ENE, POLYMER-BOUND 1,8-DIAZABICYCLO[5.4.0] UNDEC-7-ENE (67.2.6) DBU(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 POLY&

  • 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
  • Pyrimido[1,2-a]azep
  • 1,8-Diazabicyclo[5.4.]undec-7-ene
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 98% 100GR
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 98% 25GR
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 98% 500GR
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 98% 5GR
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene,2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU
  • 8-Diazabicyclo[5.4.0]undec-7-ene (DBU)
  • Lupragen N700 (Diazabicycloundecene)
  • DBU 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 2,3,4,6,7,8,9,10-OctahydropyriMido[1,2-a]azepine
  • 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE FOR S
  • 1,8- twoazabicyclo[5.4.0] eleven carbon-7- ene
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene puriss., >=99.0% (GC)
  • 1,8-Diazabicyclo[5.4.0]-7-undecene, 98.0%(GC&T)
  • Is a
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene solution 1 M in ethyl acetate
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene solution
  • 1,5-Diaza(5,4,0)undec-5-ene
  • 1,5-Diazabicyclo[5.4.0]-5-undecene
  • 2,3,4,6,7,8,9,10-Octahydropyrimido(1,2-alpha)azepine
  • 2-a]azepine,2,3,4,6,7,8,9,10-octahydro-pyrimido[
  • 2-a]azepine,2,3,4,6,7,8,9,10-octahydro-Pyrimido[1
  • Diazabicycloundecene
  • Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro-
  • Pyrimido[1,2-a]azepine,2,3,4,6,7,8,9,10-octahydro-
  • 2,3,4,6,7,8,9,1-Octahydropyrimido[1,2-a]azepine
  • Diazabicycloundecene (DBU)
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 1 M in ethyl acetate, J&KSeal
  • 1,8-Diazabicyclo[5.4.0]undec-7-ene, 1 M in THF, J&KSeal
  • Baloxavir Impurity 44
  • 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine, DBU
  • 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE (DBU)
  • 1,8-diazabicyclo[5,4,0]-undecen-(7)
  • Dicyclo[5,4,0]-1,8-Diazole-7-Nonylene
  • 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-A]Aze
  • 1,8-Diazabicyclo[5,4,0]undec-7
  • 1,8-Diaza-7-bicyclo[5.4.0]undecene.
  • 1,8-Diazabicyclo(5.4.0)undec-7-en
  • 2,3,4,6,7,8,9,10-OCTAHYDROPYRIMIDO[1,2-A]AZEPINE
  • 2,3,4,6,7,8,9,10-OCTAHYDROPYRIMIDOL[1,2-A]AZEPINE
  • 2,3,4,6,7,8,9,10-OCTA-HYDRO-PYRIMIDOL[1,2-ALPHA]AZEPINE
  • DBU
  • LUPRAGEN(R) N 700
  • POLYCAT(R) 18
  • POLYCAT(R) 48
  • OCTAHYDROPYRIMIDO(1,2:A)AZEPINE
  • 1,8-DIAZABICYCLO [5.4.0] UNDEC-7-ENE (AKA) DBU
  • 1,8-Diazabicyclo5.4.0üundec-7-ene, 99%
  • 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU