1,5-Diazabicyclo(4.3.0)non-5-ene

HCID 76349
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Basic information

CAS
3001-72-7
Standard SMILES
C1CN=C2CCCN2C1
InChIKey
SGUVLZREKBPKCE-UHFFFAOYSA-N
Molecular formula
C7H12N2
Average molar mass
124.18 g/mol
Monoisotopic mass
124.10004839

Names & identifiers

Preferred name
1,5-Diazabicyclo(4.3.0)non-5-ene
IUPAC
2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine
English name
1,5-Diazabicyclo[4.3.0]non-5-ene
Molecular formula
C7H12N2
Molecular weight
124.18

Names & synonyms

3001-72-71,5-Diazabicyclo[4.3.0]non-5-ene2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine1,5-Diazabicyclo(4.3.0)non-5-ene978M4OL12QNSC-118106DTXSID101840872,3,4,6,7,8-hexahydropyrrolo(1,2-a)pyrimidineRefChem:417183diazabicyclo(4.3.0)nonenDTXCID20106578221-087-3
Show more names
DBN1,5-Diazabicyclo[4.3.0]non-5-ene,DBNDiazabicyclononene1,5-Diazabicyclonon-5-ene1,5-diazobicyclo[4.3.0]non-5-ene1,5-DiazabicycLo[4.3.0]non-5-eneDiazabicyclononene (DBN)
2H,3H,4H,6H,7H,8H-pyrrolo[1,2-a]pyrimidinePyrrolo[1,2-a]pyrimidine, 2,3,4,6,7,8-hexahydro-MFCD000055541,5-Diazabicyclo[4.3.0]-5-noneneUNII-978M4OL12QEINECS 221-087-31,5-diazabicyclo[4,3,0]non-5-eneNSC 118106

Database identifiers

CAS
3001-72-7
PubChem CID
76349
DTXSID
DTXSID10184087
ChEMBL
CHEMBL3303308
ChEBI
CHEBI:183972
UNII
978M4OL12Q
Nikkaji
J151.114I

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
15.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
9

Physicochemical properties

Boiling point
95 · 95-98 °C7.5 mm Hg(lit.)
Density
1.005 g/mL · 1.005 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.519(lit.)
Flash point
202 °F · 202 °F
storage temp.
30 °C · Store below +30°C.
solubility
soluble in Chloroform, Methanol

Safety & regulation

Hazard information

Regulatory Information · 2 items

Chemical: Pyrrolo[1,2-a]pyrimidine, 2,3,4,6,7,8-hexahydro-

1,5-Diazabicyclo(4.3.0)non-5-ene: Does not have an individual approval but may be used under an appropriate group standard

Regulatory information

Regulatory Information · 2 items

Chemical: Pyrrolo[1,2-a]pyrimidine, 2,3,4,6,7,8-hexahydro-

1,5-Diazabicyclo(4.3.0)non-5-ene: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
1-3-8-10
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
ridadr
UN 3267 8/PG 2
hs_code
29335995
risk_code
34

Chemistry & industry

Applications · 3 items

Description1,5-Diazabicyclo [4.3.0]non-5-ene is a amidine base used in organic synthesis. It is employed for dehydrohalogenation reactions as well as base-catalyzed rearrangements. It can also be used as the nucleophilic catalyst for the Friedel-Crafts acylation of pyrroles and indoles2. Further, it is used as a resin curing agent and polyurethane catalyst.

Uses1,5-Diazabicyclo[4.3.0]non-5-ene is employed for dehydrohalogenation reactions and base-catalyzed rearrangements in organic synthesis. It is an amidine base used in organic synthesis. Further, it is used as a resin curing agent and polyurethane catalyst.

Uses1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is an amidine base commonly used in the base-mediated eliminations, condensations, esterifications, isomerizations, carboxylations and carbonylations.It is used in the preparation of supertetrahedral chalcogenide clusters and single crystals of polymer-chalcogenide composites.It also acts as a catalyst for the regioselective Friedel-Crafts C-acylation of pyrroles.

Preparation methods · 1 item

Preparation1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) can be prepared by reacting valerate with acrylonitrile to generate N-acrylonitrile valerate, followed by reduction of the cyano group to an amino group, resulting in intramolecular dehydration cyclization.

Upstream & downstream products

Downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: 1,5-diazabicyclo[4.3.0]-non-5-ene is a pyrrolopyrimidine.

Related reactions

131 records
New reaction record

Compound notes

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