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3001-72-7 - 1,5-Diazabicyclo[4.3.0]non-5-ene, 98% - DBN - A13437 - Alfa Aesar

A13437 1,5-Diazabicyclo[4.3.0]non-5-ene, 98%

CAS Number
3001-72-7
Synonyms
DBN

Size Price ($) Quantity Availability
5g 17.84
25g 63.14
100g 179.46
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1,5-Diazabicyclo[4.3.0]non-5-ene, 98%

MDL
MFCD00005554
EINECS
221-087-3

Chemical Properties

Formula
C7H12N2
Formula Weight
124.19
Boiling Point
95-98°/7mm
Flash Point
94°(201°F)
Density
1.042
Refractive Index
1.5200
Sensitivity
Air Sensitive & Hygroscopic
Solubility
Miscible with water.

Applications

1,5-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.

Notes

Air, light and moisture sensitive. Hygroscopic. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acid chlorides, acid anhydrides, oxidizing agents and chloroformates.

Literature 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).

Parviainen, A.; Wahlström, R.; Liimatainen, U.; Liitiä, T.; Rovio, S.; Helminen, J. K. J.; Hyväkkö, U.; King, A. W. T.; Suurnäkki, A.; Kilpeläinen, I. Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo[4.3.0]non-5-enium acetate: a batch simulation of the IONCELL-F process. RSC Adv. 2015, 5 (85), 69728-69737.

Barykina-Tassa, O. V.; Snider, B. B. Studies toward the synthesis of cinachyramine. An efficient route to 1,5-diazabicyclo[4.4.0]dec-5-enes. Tetrahedron Lett. 2015, 56 (23), 3151-3154.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2417
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2933.59
TSCA
No

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