2H,3H,4H,6H,7H,8H-pyrrolo[1,2-a]pyrimidine

• ChemBase ID: 89784
• Molecular Formular: C7H12N2
• Molecular Mass: 124.18358
• Monoisotopic Mass: 124.10004839
• SMILES: N1=C2N(CCC1)CCC2
• Canonical SMILES: C1CN=C2N(C1)CCC2
• InChI: InChI=1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2
• InChIKey: SGUVLZREKBPKCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2H,3H,4H,6H,7H,8H-pyrrolo[1,2-a]pyrimidine
• IUPAC Traditional name: DBN
• Synonyms: 2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine; DBN; 1,5-Diazabicyclo(4.3.0)non-5-ene; 1,5-Diazabicyclo[4.3.0]non-5-ene; 1,5-Diazabicyclo[4.3.0]non-5-ene 97%; 1,5-二氮杂双环[4.3.0]壬-5-烯; 1,5-二氮双环[4.3.0]壬-5-烯

Database IDs

• CAS Number: 3001-72-7
• EC Number: 221-087-3
• MDL Number: MFCD00005554
• Beilstein Number: 2417
• PubChem SID: 162076640; 24860252; 24848287
• PubChem CID: 76349
• Chemspider ID: 68826
• Wikipedia Title: 1,5-Diazabicyclo(4.3.0)non-5-ene

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.4970253
• LogD (pH = 7.4): -2.482047
• Log P: -0.08176086
• Molar Refractivity: 37.4028 cm^3
• Polarizability: 14.026786 Å^3
• Polar Surface Area: 15.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 95–98 °C at 7.5 mmHg; 95-98 °C/7.5 mmHg(lit.); 95-98°C/7.5mm; 95-98°C/7mm
• Flash Point: 201.2 °F; 94 °C; 94°C; 94°C(201°F)
• Density: 1.005; 1.005 g/cm3; 1.005 g/mL at 25 °C(lit.); 1.042
• Refractive Index: 1.519; 1.5200; n20/D 1.519(lit.); n20/D 1.521

Safety Information

• Storage Warning: Air Sensitive & Hygroscopic; Corrosive/Light Sensitive/Air Sensitive/Moisture Sensitive/Hygroscopic/Store under Argon
• European Hazard Symbols: Corrosive (C)
• UN Number: 3267; UN3267
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3267 8/PG 2

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C7H12N2

DETAILS

Sigma Aldrich - 136581

Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 33471

Other Notes
Amidine base used for dehydrohalogenation reactions to olefins1

REFERENCES

• The bicyclic amidines, DBN and DBU are strong organic bases initially introduced as reagents for dehydrohalogenation in vitamin A synthesis: Chem. Ber., 99, 2012 (1966).
• For use of DBN in the aldol condensation, see: J. Am. Chem. Soc., 90, 3245 (1968). For esterification of thermally unstable carboxylic acids with diethyl sulfate at ambient temperature, see: Synth. Commun., 6, 89 (1976). For use in the alkylation of thiols with dihalomethanes, see: Synthesis, 952 (1980). In refluxing xylene, DBN and DBU cleave hindered esters, e.g. mesitoates, by alkyl-oxygen cleavage: Tetrahedron Lett., 3987 (1972); J. Org. Chem., 38, 1223 (1973).