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1,8-Diazabicyclo[5.4.0]undec-7-ene CAS 6674-22-2

Molecular Formula: C9H16N2

Formula Weight: 152.24

ZSpharmac: 1,8-Diazabicyclo[5.4.0]undec-7-ene Supplement

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Product Name: 1,8-Diazabicyclo[5.4.0]undec-7-ene
CAS No: 6674-22-2
Purity: 99%

Basic Info

Product Name:1,8-Diazabicyclo[5.4.0]undec-7-ene
Other Names:1,8-Diazabicyclo[5.4.0]-7-undecene
CAS:6674-22-2
Place of Origin:Shandong, China
Brand Name:ZSpharmac
Type:Organic Intermediate
Appearance:Clear Colorless to Light Yellow Liquid
EINECS No.:229-713-7
Storage:Store Below +30°C.
Provide:1,8-Diazabicyclo[5.4.0]undec-7-ene MSDS;
1,8-Diazabicyclo[5.4.0]undec-7-ene COA

What is 1,8-Diazabicyclo[5.4.0]undec-7-ene?

As a kind of organic strong base with unique structure, 1,8-Diazabicyclo[5.4.0]undec-7-ene has been used in many synthetic reactions, showing the catalytic effect that other strong bases are difficult to play.It can be predicted that with the deepening of people’s understanding of 1,8-Diazabicyclo[5.4.0]undec-7-ene, 1,8-Diazabicyclo[5.4.0]undec-7-ene will have a wide range of uses in the research of improving existing synthesis techniques, developing new organic synthesis methods, and synthesizing new products.

1,8-Diazabicyclo[5.4.0]undec-7-ene 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
PH12.8 (10g/l, H2O, 20℃)
PH Range12.8 at 10 g/l at 20 °C
explosive limit1.1-6.5%(V)
Water Solubility soluble

 

1,8-Diazabicyclo[5.4.0]undec-7-ene Uses

  1. 1,8-Diazabicyclo[5.4.0]undec-7-ene is a catalyst for the production of polyurethane and other chemicals, such as the reaction of ammonia and dichloroethane in its presence to form piperazine, which is an excellent catalyst. Dehydrating agent, epoxy resin hardener, rust inhibitor, and advanced corrosion inhibitor can be formulated. Accelerator for resin curing, especially for the outer sealing resin of integrated circuits and electronic parts; dehalogenation reaction, dimerization and trimer dehalogenation reaction; desulfonic acid and denitric acid reaction during polymerization.
  2. 1,8-Diazabicyclo[5.4.0]undec-7-ene amidine base for dehydrohalogenation to form alkenes; more important applications such as esterification of carboxylic acids with alkyl halides; reactive methylene compounds alkylation and acylation.
  3. 1,8-Diazabicyclo [5.4.0] undec-7-ene is utilized in the manufacture of cephalosporin semi-synthetic antibiotics, and also in the preparation of deacidification representatives, corrosion inhibitors, as well as advanced rust inhibitors.

1,8-Diazabicyclo[5.4.0]undec-7-ene Catalyzes CDI-Activated Amination Reactions

This paper reports that 1,8-Diazabicyclo[5.4.0]undec-7-ene has the function of catalyzing the amination reaction of acylimidazole compounds. Especially for the traditionally inactive, electron-deficient aniline compounds, DBU has obvious advantages in terms of safety and dosage compared with catalysts commonly used in the past, such as 1-hydroxybenzotriazole (HOBt).
N,N’-Carbonyldiimidazole (CDI) is commonly used in the synthesis of amide compounds from carboxylic acids and amines. In a one-pot reaction, usually activated by CDI, the carboxylic acid and CDI (1) are first stirred until the activated intermediate acylimidazole compound (2) is formed, followed by the addition of the amine to give the product (Scheme 1). Only harmless by-products—carbon dioxide and imidazole are produced in this process, which is an effective method for synthesizing amide compounds, especially widely used in the pharmaceutical industry.
Acyl imidazole compounds are generally more stable and easier to handle than the corresponding acyl chloride compounds, but due to their lower activity, a catalyst is usually added to react with sterically hindered carboxylic acids, amines, or weakly nucleophilic amines. Increase the reaction rate. Among them, the most commonly used catalyst is 1-hydroxybenzotriazole (HOBt, 3), which has considerable stability for improving the reaction rate, but due to its large amount in the reaction, it is easy to decompose and even has the danger of explosion, and it is not easy to transport, thus limiting its application. In recent years, some new catalysts have been studied and used (Figure 1), such as 2-hydroxy-5-nitropyridine (NO2-HOPyr, 4) and imidazole hydrochloride (Im.HCl, 5), compared with HOBt, They have the advantages of less dosage, easy operation and stability.
Traditionally, 1,8-Diazabicyclo[5.4.0]undec-7-ene has been considered as a non-nucleophilic base, but it is more effective in Baylis-Hillman reactions than conventional catalysts such as 1,4-diazacyclo[2,2,2]octane (DABOC) and 4 -Dimethylaminopyridine (DMAP) exhibits stronger nucleophilicity, and can react carboxylic acid with dimethyl carbonate to generate methyl ester compounds. Furthermore, amidines are also used to catalyze the acylation of acetic anhydride with secondary phenethyl alcohol. Based on the above findings and the authors’ experience, they envisage the use of 1,8-Diazabicyclo[5.4.0]undec-7-ene in catalyzing amination reactions that are usually slower after CDI activation.
It can be seen from the table that in the presence of 1,8-Diazabicyclo[5.4.0]undec-7-ene, the acylation reaction rate of traditionally inactive, electron-deficient aniline compounds can be greatly improved, and the yield of the reaction is also greatly improved. The possible mechanism of the reaction is:

In summary, 1,8-Diazabicyclo[5.4.0]undec-7-ene is a safe and efficient catalyst for the amination of acyl imidazoles. For aliphatic amines or anilines, its catalytic acceleration effect is comparable to other known catalysts, especially for electron-deficient aniline compounds. Better than NO2-HOPyr and Im﹒ HCl. Although the stronger basicity of 1,8-Diazabicyclo[5.4.0]undec-7-ene can affect some substrates, it can still serve as a useful complement to existing catalysts.

Alkaline Effect on Undi-2 in 2,1-Diazobic [3.1.0] Undesi-2-N

In organic synthesis, 1,8-Diazabicyclo[5.4.0]undec-7-ene, as a special base, has a wide range of practicability and applicability. If an organic base such as TEA, DIPEA, etc. does not react or the reaction is not good, we will subconsciously think or try another base. 1,8-Diazabicyclo[5.4.0]undec-7-ene is usually one of the options at this time. In our impression, DBU is an organic strong base that can be used almost without any disadvantages. It has no nucleophilicity, stable structure, large steric hindrance, good catalytic effect, and no special incompatibility with solvents. Many reactions have been applied, these are generally no problem, but these understandings are not comprehensive. Regarding the alkalinity of DBU and its analogs, how strong is the alkalinity and why it is so strong, I believe that many small partners are still unclear. In acetonitrile, the pKa of triethylamine is 18.8, while the pKa of DBU and its analogs is between 23.4 and 26.0, and the pKa in other solvents is shown in the figure below. There are three main reasons why they are so strong: 1. The imine nitrogen atom in the molecular structure is SP2 hybridized; 2. The stability of its conjugate acid is stronger; The alkyl group of electrons increases the electron density of the SP2 hybridized nitrogen atom. Regarding the non-nucleophilicity of DBU and its analogs, which is often touted, this is only applicable under certain conditions, relative to anionic amide and alkoxide bases. In many cases, for example: primary halogenated hydrocarbons, benzyl halogenated hydrocarbons, chlorophosphates, acid chlorides, etc. have strong nucleophilicity, and the nucleophilicity of DBU and its analogs is higher than that of DMAP and PPh3 . Regarding the stability of DBU and its analogs, in fact, they are relatively easy to undergo ring-opening hydrolysis in water. For the mechanism of their hydrolysis, scientists have proposed two possible ways, but there is not enough data to prove that their rationality is superior to another. one. For route A, its hydrolysis first yields the primary amine, which can then react with the electrophile. In route B, the amidine interacts reversibly with the electrophile to produce a cationic intermediate, which then reacts with a solvent when the reaction is quenched with a small amount of water or water. Route A is estimated when large amounts of water are present, and route B is estimated under strictly anhydrous conditions and/or when certain electrophiles are present. In the literature (Org.Process Res.Dev.2019,23,9,1860-1871), the author used DBU in one step of the synthesis process of MK-3682, and accidentally obtained impurity 9. The author studied in detail The effects of moisture and temperature on the degradation of DBU were studied, and it was concluded that the more moisture and the higher the temperature, the faster and more DBU degraded.

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ZhiShang Chemical is owned by ZhiShang Group is a professional new-type chemicals enterprise combined into research and development, production and sales .

The company’s competitive product is pharmaceutical raw materials and intermediates (especially carbohydrate derivatives Series), In recent years, the company has made a major breakthrough in food and feed additives, plant extraction, industrial chemicals industry .

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