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6674-22-2 molecular structure
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2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine

ChemBase ID: 67496
Molecular Formular: C9H16N2
Molecular Mass: 152.23674
Monoisotopic Mass: 152.13134852
SMILES and InChIs

SMILES:
N12CCCCCC1=NCCC2
Canonical SMILES:
C1CCN2C(=NCCC2)CC1
InChI:
InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2
InChIKey:
GQHTUMJGOHRCHB-UHFFFAOYSA-N

Cite this record

CBID:67496 http://www.chembase.cn/molecule-67496.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine
IUPAC Traditional name
1,8-diazabicycloundec-7-ene
Synonyms
1,8-Diazabicyclo[5.4.0]undec-7-ene
2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine
DBU
DBU,Diazabicycloundecene
1,8-Diazabicycloundec-7-ene
2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
DBU solution
1,8-Diazabicyclo[5.4.0]undec-7-ene solution
2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine
1,8-Diazabicyclo[5.4.0]undec-7-ene
1,8-Diazabicyclo-[5,4,0]undec-7-ene
DBU
DBU 溶液
1,8-二氮杂双环[5.4.0]十一碳-7-烯 溶液
2,3,4,6,7,8,9,10-八氢嘧啶并[1,2-a]氮杂卓
1,8-二氮双环[5.4.0]十一-7-烯
1,8-二氮杂双环[5.4.0]十一碳-7-烯
CAS Number
6674-22-2
EC Number
229-713-7
MDL Number
MFCD00006930
Beilstein Number
508906
PubChem SID
24860258
162033231
24860259
24848373
PubChem CID
81184
Chemspider ID
73246
Wikipedia Title
1,8-Diazabicycloundec-7-ene

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -1.607904  LogD (pH = 7.4) -1.5941415 
Log P 0.80737644  Molar Refractivity 46.6048 cm3
Polarizability 17.711895 Å3 Polar Surface Area 15.6 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
Colorless liquid expand Show data source
Melting Point
-70°C expand Show data source
-70°C expand Show data source
Boiling Point
115 °C/11 mmHg(lit.) expand Show data source
261°C expand Show data source
80-83 °C (0.6 mmHg), 261 °C (1 atm) expand Show data source
80-83 °C/0.6 mmHg(lit.) expand Show data source
80-83°C expand Show data source
Flash Point
0 °F expand Show data source
116 °C expand Show data source
116°C expand Show data source
116°C(240°F) expand Show data source
119.9°C expand Show data source
-18 °C expand Show data source
240.8 °F expand Show data source
25 °F expand Show data source
-4 °C expand Show data source
Density
0.899 g/mL at 25 °C expand Show data source
0.908 g/mL at 25 °C expand Show data source
1.018 expand Show data source
1.018 g/mL at 25 °C(lit.) expand Show data source
1.018 g/mL liquid expand Show data source
1.019 g/mL at 20 °C(lit.) expand Show data source
1.020 expand Show data source
Refractive Index
1.5220 expand Show data source
n20/D 1.395 expand Show data source
n20/D 1.425 expand Show data source
n20/D 1.522-1.524(lit.) expand Show data source
n20/D 1.523 expand Show data source
Vapor Pressure
5.3 mmHg ( 37.7 °C) expand Show data source
Hydrophobicity(logP)
1.142 expand Show data source
pKa
~12 (value for protonated form, pKa of a free base is ~24 -> C-H bond dissociation) expand Show data source
pKb
? (basicity) expand Show data source
Storage Warning
Air Sensitive expand Show data source
Corrosive/Air Sensitive/Store under Argon expand Show data source
IRRITANT expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
Flammable Flammable (F) expand Show data source
X expand Show data source
UN Number
2924 expand Show data source
3267 expand Show data source
UN3267 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
8 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Risk Statements
11-19-34-37 expand Show data source
11-34-66-67 expand Show data source
22-34-52/53 expand Show data source
R22 R34 expand Show data source
Safety Statements
16-26-33-36/37/39-45 expand Show data source
16-29-33-36/37/39-45 expand Show data source
26-36/37/39-45 expand Show data source
26-36/37/39-45-60-61 expand Show data source
S24 S25 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H290-H301-H314-H412 expand Show data source
H301-H314-H318-H402-H412 expand Show data source
GHS Precautionary statements
P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A expand Show data source
P273-P280-P301 + P310-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2924 3/PG 2 expand Show data source
UN 3267 8/PG 2 expand Show data source
Purity
≥98.0% (GC) expand Show data source
≥99.0% (GC) expand Show data source
95% expand Show data source
95+% expand Show data source
98% expand Show data source
99% expand Show data source
Concentration
1 M in ethyl acetate expand Show data source
1 M in THF expand Show data source
Grade
puriss. expand Show data source
purum expand Show data source
Empirical Formula (Hill Notation)
C9H16N2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia
Sigma Aldrich - 139009 external link
Application
Halogenated Diels-Alder adducts were dehydrohalogenated with this base, and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3).2
Used in a new synthesis of the ABCD ring system of Camptothecin.
Features and Benefits
Strong hindered amine base.
Packaging
25, 100, 500 g in glass bottle
Citation
An application review.1
Sigma Aldrich - 714860 external link
Packaging
100 mL in Sure/Seal™
Sigma Aldrich - 714852 external link
Packaging
100 mL in Sure/Seal™
Sigma Aldrich - 33482 external link
Other Notes
Amidine base used for dehydrohalogenation reactions to olefins1; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides2,3; Alkylation and acylation of active methylene compounds4

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).
  • • For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).
  • • Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
  • • Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).
  • • Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).
  • • Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).
  • • For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenylphosphonic azide, A12124.
  • • DBU forms hydrogen-bonded complexes with carboxylic acids, which can be alkylated in good yield by alkyl bromides or iodides, in a simple esterification procedure: Bull. Chem. Soc. Jpn., 51, 2401 (1978).
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PATENTS

PATENTS

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INTERNET

INTERNET

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