2-Furonitrile: Difference between revisions

{{Orphan|date=January 2012}}

| IUPACName = furan-2-carbonitrile

| Section1 = {{Chembox Identifiers

| CASNo = 617-90-3

| PubChem = 69245

| ChemSpiderID = 62458

| SMILES = N#Cc1occc1

| InChI = 1/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H

| InChIKey = YXDXXGXWFJCXEB-UHFFFAOYAE

| StdInChI = 1S/C5H3NO/c6-4-5-2-1-3-7-5/h1-3H

| StdInChIKey = YXDXXGXWFJCXEB-UHFFFAOYSA-N

| Section2 = {{Chembox Properties

| C = 5 | H = 3 | N = 1 | O = 1

| Appearance = colorless to light yellow

| Density = 1.0650 @20 °C

| MeltingPt =

| BoilingPt = 147 °C

| Solubility =

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt = 95 °F

| Autoignition =

'''2-Furonitrile''' is a colorless to light yellow liquid furan derivative having a boiling point of 147 °C at atmospheric pressure<ref>{{cite journal | author = Patrice Capdevielle | title = Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles | journal = Synthesis | volume = 6 | pages = 451–452 | year = 1989 |last2 = Lavigne | first2 = Andre | last3 = Maumy | first3 = Michel}}</ref> and with a density somewhat higher than that of water (1.0650 g/ml at 20 °C).<ref>{{cite journal | author = P. A. Pavlov | title = Synthesis of 5-substituted furannitriles and their reaction with hydrazine | journal = Khimiya Geterotsiklicheskikh Soedinenii | volume = 2 | pages = 181–186 | year = 1986 |last2 = Kul'nevich | first2 = V. G. }}</ref>

2-Furonitrile has been prepared in high yield and conversion from the vapor phase reaction of [[furfural]] and [[ammonia]] over bismuth molybdate catalyst. The reactants are fed in separate streams, in the presence of air and steam over the catalyst bed at 440-480 °C<ref>Thomas J. Jennings, “Process for preparing furonitrile”, US Patent 3,260,731 (1966)</ref>

Additionally, furfural has been converted to 2-furonitrile by a number of reagents, including [[hydrazoic acid]]-[[perchloric acid]], [[hypervalent iodine]] (III) and [[n-bromosuccinimide]].<ref>{{cite journal | author = P. A. Pavlov | title = Synthesis of 5-substituted furannitriles and their reaction with hydrazine | journal = Khimiya Geterotsiklicheskikh Soedinenii | volume = 2 | pages = 181–186 | year = 1986 |last2 = Kul'nevich | first2 = V. G. }}</ref><ref>{{cite journal | author = Chenjie Zhu | title = Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent | journal = Synthesis | volume = 24| pages = 4235–4241| year = 2010 |last2 = Sun | first2 = Chengguo | last3 = Wei | first3 = Yunyang }}</ref> Thus, 2-furonitrile has been prepared in good yield by treating [[furfural]] with a mixture of [[hydrazoic acid]] [[HN3]] and [[perchloric acid]] in the presence of magnesium perchlorate in the [[benzene]] solution at 35 °C.<ref>{{cite journal | author = P. A. Pavlov | title = Synthesis of 5-substituted furannitriles and their reaction with hydrazine | journal = Khimiya Geterotsiklicheskikh Soedinenii | volume = 2 | pages = 181–186 | year = 1986 |last2 = Kul'nevich | first2 = V. G. }}</ref><ref>{{cite journal | author = B. Bandgar | title = Organic reactions in water. Transformation of aldehydes to nitriles using NBS under mild conditions | journal = Synthetic Communications | volume = 36 | pages = 1347–1352 | year = 2006 |last2 = Makone | first2 = S. | issue = 10}}</ref> Similarly, a [[hypervalent iodine]] (III) reagent was used, as oxidant, together with ammonium acetate, as the nitrogen source, to provide 2-furonitrile in aqueous acetonitrile at 80 °C in 90% yield.<ref>{{cite journal | author = Chenjie Zhu | title = Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent | journal = Synthesis | volume = 24| pages = 4235–4241| year = 2010 |last2 = Sun | first2 = Chengguo | last3 = Wei | first3 = Yunyang }}</ref> Selective conversion of furfural to 2-furonitrile was achieved under mild conditions in aqueous ammonium hydroxide solution employing n-bromosuccinimide (NBS) at ice bath temperatures.<ref>{{cite journal | author = B. Bandgar | title = Organic reactions in water. Transformation of aldehydes to nitriles using NBS under mild conditions | journal = Synthetic Communications | volume = 36 | pages = 1347–1352 | year = 2006 |last2 = Makone | first2 = S. | issue = 10}}</ref>

2-Furonitrile has also been prepared from other [[furan]] derivatives, including furfural aldoxime and furoic acid amide. Thus, a laboratory-scale synthesis of 2-furonitrile has been described employing the dehydration of 2-furoic acid amide or oxime via [[flash vacuum pyrolysis]] over molecular sieves in the gas phase.<ref>{{cite journal | author = Jacqueline A. Campbell | title = Laboratory-scale synthesis of nitriles by catalyzed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions | journal = Synthesis | volume = 20| pages = 3179–3184| year = 2007 |last2 = McDougald | first2 = Graham | last3 = McNab | first3 = Hamish}}</ref> Additionally, the dehydration of furfural aldoxime to 2-furonitrile has been accomplished in high yield employing thionyl chloride-benzotriazole<ref>{{cite journal | author = Sachin S. Chaudhari | title = Thionyl chloride-benzotriazole: an efficient system for transformation of aldoximes to nitriles | journal = Synthetic Communications | volume = 29 | pages = 1741–1745| year = 1999 |last2 = Akamanchi | first2 = Krishnacharya G. | issue = 10}}</ref> or triphenylphosphine-iodine reagents.<ref>{{cite journal | author = A. Narsaiah | title = Triphenylphosphine-iodine. An efficient reagent system for the synthesis of nitriles from aldoximes | journal = Synthetic Communications | volume = 36 | pages = 137–140 | year = 2006 |last2 = Sreenu | first2 = D. | last3 = Nagaiah | first3 = K. | issue = 2}}</ref>

2-Furonitrile has been suggested as a useful extractive distillation solvent and as a sweetening agent. It has about thirty times the sweetening power of sucrose.<ref>Thomas J. Jennings, “Process for preparing furonitrile”, US Patent 3,260,731 (1966)</ref> 2-Furonitrile is also useful as an intermediate in pharmaceutical and fine chemical synthesis.

Thus, 2-furonitrile was used in the synthesis of adenosine A2a receptor antagonists (including drugs for the treatment of Parkinson's disease),<ref>J. Kent Barbay, et. al., “Preparation of methylene amines of thieno[2,3-d]pyrimidine and their use as adenosine A2a receptor antagonists”, PCT Int. Appl. (2010), WO 2010045006 A1 20100422 (2010)</ref> antiviral agents<ref>Michele M Cudahy, et. al., “Preparation of 4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide antiviral agents”, PCT Int. Appl. (2003), WO 2003059911 A2 20030724 (2003)</ref> and cardiotonic agents<ref>Chau Ting. Huang, et. al., “Preparation of N-hydroxy-5-phenyl-2-furancarboximidamides as cardiotonic agents”, Eur. Pat. Appl., EP 321431 A1 19890621 (1989).</ref>

[[Category:Furans]]