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110-00-9

Basic Information
CAS No.: 110-00-9
Name: Furan
Article Data: 303
Cas Database
Molecular Structure:
Molecular Structure of 110-00-9 (Furan)
Formula: C4H4O
Molecular Weight: 68.0752
Synonyms: Divinyleneoxide;Furfuran;Oxacyclopentadiene;Oxole;Tetrole;
EINECS: 203-727-3
Density: 0.942 g/cm3
Melting Point: -85.6 °C
Boiling Point: 31.36 °C at 760 mmHg
Flash Point: -35 °C
Solubility: insoluble in water
Appearance: clear colorless liquid
Hazard Symbols: ToxicT, HighlyF+
Risk Codes: 45-12-19-20/22-38-48/22-52/53-68
Safety: 53-45-61
Transport Information: UN 2811 6.1/PG 2
PSA: 13.14000
LogP: 1.27960
Synthetic route
98-01-1

furfural

Conditions
ConditionsYield
With carbon dioxide; palladium/alumina at 145℃; under 45004.5 Torr; for 6.5h; Green chemistry;99%
With carbon dioxide; 5% Pd(II)/C(eggshell) at 250℃; under 112511 Torr; Supercritical conditions;98%
With palladium nanoparticles deposited on porous SBA-15 In cyclohexane at 150℃; for 24h; Molecular sieve;96%
82660-71-7

2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>

A

110-00-9

furan

B

5732-90-1

1-oxaspiro<4.4>non-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 130℃;A n/a
B 98%

[3-(1-Benzylamino-pentyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

A

110-00-9

furan

B

(Z)-4-Benzylamino-oct-2-en-1-ol

Conditions
ConditionsYield
at 120℃; for 0.25h; Irradiation;A n/a
B 98%

{3-[1-(4-Methoxy-benzylamino)-pentyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl}-methanol

A

110-00-9

furan

B

(Z)-4-(4-Methoxy-benzylamino)-oct-2-en-1-ol

Conditions
ConditionsYield
at 120℃; for 0.25h; Irradiation;A n/a
B 98%

[3-(1-Dibenzylamino-pentyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

A

110-00-9

furan

B

(Z)-4-Dibenzylamino-oct-2-en-1-ol

Conditions
ConditionsYield
at 140℃; for 0.166667h; Irradiation;A n/a
B 98%

{3-[4-Benzyloxy-1-(4-methoxy-benzylamino)-butyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl}-methanol

A

110-00-9

furan

B

(Z)-7-Benzyloxy-4-(4-methoxy-benzylamino)-hept-2-en-1-ol

Conditions
ConditionsYield
at 120℃; for 0.25h; Irradiation;A n/a
B 98%

[3-(4-Benzyloxy-1-dibenzylamino-butyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

A

110-00-9

furan

B

(Z)-7-Benzyloxy-4-dibenzylamino-hept-2-en-1-ol

Conditions
ConditionsYield
at 140℃; for 0.166667h; Irradiation;A n/a
B 98%
82660-72-8

2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>

A

110-00-9

furan

B

4435-19-2

1-oxa-spiro[4.5]dec-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 130℃; under 7 Torr;A n/a
B 97%
930-22-3

epoxybutene

A

1708-29-8

2,5-dihydrofuran

B

110-00-9

furan

C

123-73-9

trans-Crotonaldehyde

Conditions
ConditionsYield
tetra-n-heptylammonium iodide; tributyltin iodide In para-xylene at 109 - 117℃; for 0.75h;A 96.1%
B n/a
C n/a
25414-22-6

2-methoxyfuran

123-73-9

trans-Crotonaldehyde

dichloroacetic acid (DCA)

dichloroacetic acid (DCA)

346440-54-8

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one

Conditions
ConditionsYield
In diethyl ether; chloroform95%
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Chemistry

Molecular Structure:

Molecular Formula: C4H4O
Molecular Weight: 68.074
IUPAC Name: Furan
Synonyms of Furan (CAS NO.110-00-9): 1,4-Epoxy-1,3-butadiene ; 5-17-01-00291 (Beilstein Handbook Reference) ; AI3-24244 ; Axole ; BRN 0103221 ; CCRIS 3159 ; Divinylene oxide ; EINECS 203-727-3 ; Furfuran ; HSDB 89 ; NCI-C56202 ; Oxacyclopentadiene ; Oxole ; RCRA waste number U124 ; Tetrole ; Furan [UN2389] [Flammable liquid] ; UN2389
CAS NO: 110-00-9
Classification Code: Mutation data ; Reproductive Effect ; Tumor data
Melting point: -85.6 °C 
Index of Refraction: 1.427
Molar Refractivity: 18.55 cm3
Molar Volume: 72.2 cm3
Surface Tension: 24.8 dyne/cm
Density: 0.942 g/cm3
Enthalpy of Vaporization: 27.1 kJ/mol
Boiling Point: 31.4 °C at 760 mmHg
Vapour Pressure: 605 mmHg at 25°C
Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system  similar to benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.

History

  In 1780 by Carl Wilhelm Scheele, the first Furan (CAS NO.110-00-9) derivative to be described was 2-furoic acid. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limpricht in 1870, although he called it tetraphenol.

Uses

  Furan (CAS NO.110-00-9) is mainly used to produce large quantities of hot-box process core Binder.

Production

Furan can be obtained from FURFURAL by oxidation and decarboxylation of the resulting furan-2-carboxylic acid, the FURFURAL being derived by destructive distillation of corn cobs in the presence of SULFURIC ACID.
the Feist-Benary synthesis is the organic synthesis of classic furan.   
and there is a simple synthesis methods for furans is the reaction of 1,4-diketones with PHOSPHORUS PENTOXIDE  in the Paal-Knorr Synthesis. It is interesting that the Thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 140mg/kg (140mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: HEMORRHAGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926.
dog LDLo oral 234mg/kg (234mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: HEMORRHAGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926.
mouse LC50 inhalation 120mg/m3/1H (120mg/m3) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979.
mouse LD50 intraperitoneal 7mg/kg (7mg/kg)   American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979.
rabbit LDLo oral 234mg/kg (234mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: HEMORRHAGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926.
rat LC50 inhalation 3398ppm/1H (3398ppm) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Hazelton Laboratories, Reports. Vol. HLA468-102, Pg. 1987,
rat LD50 intraperitoneal 5200ug/kg (5.2mg/kg)   American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979.

Safety Profile

Hazard Codes of Furan (CAS NO.110-00-9): ToxicT,HighlyF+
Risk Statements: 45-12-19-20/22-38-48/22-52/53-68 
R45: May cause cancer. 
R12: Extremely flammable. 
R19: May form explosive peroxides. 
R20/22: Harmful by inhalation and if swallowed. 
R38: Irritating to skin. 
R48/22: Harmful: danger of serious damage to health by prolonged exposure if swallowed. 
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R68: Possible risk of irreversible effects.
Safety Statements: 53-45-61 
S53: Avoid exposure - obtain special instructions before use. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: OB3870000
F: 8-9-23
HazardClass: 3
PackingGroup: I

Specification

Behavior of Furan (CAS NO.110-00-9) is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran due to its aromaticity, .It is considerably more reactive than benzene in electrophilic substitution reactions, due to the electron-donating effects of the oxygen heteroatom. Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.