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

Base Information

• Chemical Name: 1,8-Diazabicyclo[5.4.0]undec-7-ene
• CAS No.: 6674-22-2
• Deprecated CAS: 31171-04-7,41015-70-7,51301-56-5,69722-76-5,78995-63-8,83329-50-4,1802659-41-1,2058348-68-6,2102590-64-5,857293-63-1,1380214-95-8,2254312-58-6,41015-70-7,51301-56-5,78995-63-8,83329-50-4
• Molecular Formula: C9H16N2
• Molecular Weight: 152.239
• Hs Code.: H16N2 MOL WT. 152.24
• European Community (EC) Number: 229-713-7
• NSC Number: 111184
• UNII: H1ILJ6IBUX
• DSSTox Substance ID: DTXSID2049424
• Nikkaji Number: J39.656G
• Wikipedia: 1,8-Diazabicyclo(5.4.0)undec-7-ene
• Wikidata: Q306166
• Metabolomics Workbench ID: 186947
• ChEMBL ID: CHEMBL1489129
• Mol file: 6674-22-2.mol

Synonyms:1,8-DBU;1,8-diaza-7-bicyclo(5.4.0)undecene;1,8-diazabicyclo(5.4.0)undec-7-ene

Chemical Property of 1,8-Diazabicyclo[5.4.0]undec-7-ene

Chemical Property:

• Appearance/Colour: Colorless to yellow liquid
• Vapor Pressure: 5.3 mm Hg ( 37.7 °C)
• Melting Point: -70 °C
• Refractive Index: n20/D 1.523
• Boiling Point: 274.6 °C at 760 mmHg
• PKA: 13.28±0.20(Predicted)
• Flash Point: 119.9 °C
• PSA: 15.60000
• Density: 1.12 g/cm³
• LogP: 1.03810
• Storage Temp.: Store at R.T.
• Sensitive.: Air Sensitive
• Solubility.: soluble
• Water Solubility.: soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.131348519
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

1,8-Diazabicyclo[5.4.0]undec-7-ene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,F
• Statements: 22-34-52/53-35-40-37-19-11-67
• Safety Statements: 26-36/37/39-45-61-27-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1CCC2=NCCCN2CC1
• 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.
• Uses: DBU may be used:as catalyst for carboxylic acid esterification with dimethyl carbonatein the synthesis of duocarmycin and CC-1065 analogsas catalyst in aza-Michael addition and Knovenegal condensation reactionas 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)in a new synthesis of the ABCD ring system of CamptothecinDBU 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.Used in a new synthesis of the ABCD ring system of Camptothecin. 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.

Technology Process of 1,8-Diazabicyclo[5.4.0]undec-7-ene

There total 38 articles about 1,8-Diazabicyclo[5.4.0]undec-7-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-1-phenyl-ethanol (107645-81-8) → 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2,83329-50-4) + acetophenone (98-86-2)

Guidance literature:

at 150 ℃; for 2h; Product distribution;

Reference yield: 85.0%

1,8-diazabicyclo<5.4.0>undec-7-ene hidrochloride (78204-84-9) → 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2,83329-50-4)

Guidance literature:

With tri-n-propylamine; sodium methylate; In methanol;

Reference yield: 85.0%

(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-diphenyl-methanol (107645-80-7) → benzophenone (119-61-9) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2,83329-50-4)

Guidance literature:

at 180 ℃; for 2h; Product distribution;

upstream raw materials:

methanol

(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-phenyl-methanol

1-(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-1-phenyl-ethanol

(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-diphenyl-methanol

Downstream raw materials:

(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-phenyl-methanol

10-Benzyl-2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine

(2,3,4,6,7,8,9,10-Octahydro-pyrimido[1,2-a]azepin-10-yl)-diphenyl-methanol

1,3,5-Trinitro-benzene; compound with 2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine

Refernces

• 1、 He, Ming-Hui,Xu, Rui-Xin,Chen, Guang-Xue,Zeng, Zhao-Hua,Yang, Jian-Wen. "A thioxanthone-based photocaged superbase for highly effective free radical photopolymerization". . p. 1445 - 1448. Retrieved 2014.
• 2、 An, Feng,Maji, Biplab,Min, Elizabeth,Ofial, Armin R.,Mayr, Herbert. "Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts". supporting information. p. 1526 - 1547. Retrieved 2020/02/04.
• 3、 -. "MANUFACTURING METHOD OF DIAZABICYCLO COMPOUND". Paragraph 0018; 0042; 0044; 0048. . Retrieved 2018/06/08.