Oxole is the simplest oxygen containing five membered heterocyclic compound, with the chemical formula CfourHfourO[1]It is a colorless liquid existing in pine tar and has a smell similar to chloroform. It is insoluble in water and soluble in organic solvents.When its steam meets pine chips wetted by hydrochloric acid, it turns green, which is called pine wood reaction, and can be used to identify the presence of furan.It has anesthetic and weak irritant effects and is extremely flammable.Inhalation may cause headache, dizziness, nausea and respiratory failure.Furan ring is aromatic and can occurHalogenation、nitrification、sulfonationetc.Electrophilic substitution reaction, mainly used for organic synthesis or as solvent.
On October 27, 2017, the list of carcinogens released by the International Agency for Research on Cancer of the World Health Organization (WHO) was preliminarily sorted out for reference, and furan was included in the list of Category 2B carcinogens.[2]
Solubility: insoluble in water, soluble in acetone, benzene, soluble in ethanol, ether and other organic solvents[3]
chemical property
Because a pair of lone pairs of electrons of the oxygen atom in its molecule forms a large π bond in the conjugate orbital plane, there are 6 electrons in the conjugate plane, which conforms to 4n+2 structure, so furan hasAromaticity。Aromaticity makes furan "easy to replace but difficult to add".The other pair of lone electrons of oxygen extends outward.The oxygen atom itself conforms to sptwoHybridization.
Due to the presence of aromatic rings, the chemical behavior of furans is not very similar to other unsaturated heterocycles.
The oxygen in the aromatic ring has an electron donating effect, so the electrophilic substitution activity of furan is stronger than that of benzene.Resonance theoryThe study of furan found that the electron cloud density on the furan ring was high, which supported the theory of electrophilic reactivity.
Mainly used for makingpyrrole、thiophene、TetrahydrofuranEtc.After etherification and reduction of furan, 2,5-dimethoxydihydrofuran is obtained. After hydrolysis, 2-hydroxy-1,4-butanedialdehyde is generated, which can be used for synthesisAnisodamineProduction.When 2,5-dimethoxytetrahydrofuran is obtained by etherification, reduction and catalytic hydrogenation of furan, it will be hydrolyzed to form succinal, which is another alkaloidatropineRaw materials.
security information
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Safety terminology
S45：In case of accident or if you feel unwell, seek medical advice immediately (show the lable where possible).
In case of an accident or feeling unwell, seek medical advice immediately (show the label if possible).
S53：Avoid exposure - obtain special instructions before use.
Avoid contact and obtain special instructions before use.
S61：Avoid release to the environment. Refer to special instructions/Safety data sheets.
Avoid releasing into the environment, refer to special instructions/safety receipt instructions.
Risk terminology
R12：Extremely flammable.
Extremely flammable.
R19：May form explosive peroxides.
Explosive peroxides may be generated.
R20/22：Harmful by inhalation and if swallowed.
Harmful by inhalation and if swallowed.
R38：Irritating to skin.
Irritating to skin.
R45：May cause cancer.
May cause cancer.
R48/22：Harmful : danger of serious damage to health by prolonged exposure if swallowed.
Harmful: danger of serious damage to health if swallowed and exposed for a long time.
R52/53：Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
It is harmful to aquatic organisms and may cause long-term adverse effects in the aquatic environment.
