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Conditions | Yield |
---|---|
With bis(2,2'-bipyridyl) copper(II) permanganate In acetone for 0.1h; Ambient temperature; | 100% |
With 4 A molecular sieve; tetrabutylammonium perchlorate; Ru-Cu-Al-hydrotalcite In toluene at 60℃; for 3h; | 100% |
With potassium carbonate In toluene at 70℃; for 2.5h; Reagent/catalyst; | 100% |
Conditions | Yield |
---|---|
In diethyl ether for 1h; Product distribution; Irradiation; photochemical debromination was investigated; | 100% |
furfural
Conditions | Yield |
---|---|
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde; | 100% |
Conditions | Yield |
---|---|
With sulphated zirconia In acetonitrile at 60℃; for 2h; Microwave irradiation; | 100% |
With Montmorillonite K10 In dichloromethane for 0.333333h; Heating; | 98% |
With water; Sulfate; titanium(IV) oxide In dichloromethane for 0.0833333h; Deacetylation; Heating; | 97% |
2-(1,3-dithian-2-yl)furan
furfural
Conditions | Yield |
---|---|
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 1h; Micellar solution; | 100% |
With indium(III) trifluoride; water In acetonitrile for 3.5h; Reflux; chemoselective reaction; | 93% |
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.75h; | 90% |
With eosin y In water; acetonitrile at 20℃; for 4h; Irradiation; | 82% |
With ammonium iodide; dihydrogen peroxide; sodium dodecyl-sulfate In water at 20℃; for 0.333333h; micellar medium; |
furfural tosylhydrazone
furfural
Conditions | Yield |
---|---|
With Cr-MCM-41 zeolite on silica gel for 0.1h; microwave irradiation; | 98% |
With benzeneseleninic anhydride In tetrahydrofuran at 40 - 50℃; for 2h; | 88% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 2h; Oxidation; oxidative cleavage; | 80% |
Conditions | Yield |
---|---|
With sulfonated graphitic carbon nitride In water at 100℃; for 0.5h; Solvent; Temperature; | 96% |
With Sulfonated graphene at 150℃; for 0.666667h; Temperature; Sealed tube; | 96% |
With hydrogenchloride; 5-methyl-dihydro-furan-2-one In water at 224.84℃; under 28443.9 Torr; for 0.0375h; Kinetics; Temperature; Reagent/catalyst; Concentration; Flow reactor; | 93% |
Conditions | Yield |
---|---|
With Montmorillonite K 10; water In acetone for 0.5h; Heating; | 96% |
With aluminum oxide; Oxone for 0.03h; Hydrolysis; Microwave irradiation; | 93% |
With iron(III) chloride hexahydrate; acetaldehyde In dichloromethane at 20℃; for 0.25h; | 90% |
Conditions | Yield |
---|---|
With water; Dess-Martin periodane In dichloromethane at 5℃; for 0.333333h; | 95% |
With silica gel; iron(III) chloride for 0.0133333h; microwave irradiation; | 92% |
With bis(pyridine)silver(I) permanganate In dichloromethane for 0.0833333h; Ambient temperature; | 90% |
2-(Iodomethyl)tetrahydrofuran
furfural
Conditions | Yield |
---|---|
With oxygen; kieselguhr; copper(l) chloride In hexane for 2h; Oxidation; Heating; | 93% |
In 1832, the German chemist Johann Wolfgang D?bereiner ,first isolated furfural ,he formed a very small quantity of it as a byproduct of formic acid synthesis.
In 1840, the Scottish chemist John Stenhouse found that the same chemical could be produced by distilling a wide variety of crop materials, including bran, corn, oats, and sawdust, with aqueous sulfuric acid, and he determined that this chemical had an empirical formula of C5H4O2.
In 1901, the German chemist Carl Harries deduced furfural's structure.
NTP Carcinogenesis Studies (gavage); Clear Evidence: mouse NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NTP-TR-382,90, . , Some Evidence: rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NTP-TR-382 ,1990. . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
OSHA PEL: TWA 2 ppm (skin)
ACGIH TLV: TWA 2 ppm (skin); Animal Carcinogen: BEI: 200 mg/g creatinine of total furoic acid in urine at end of shift
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification: 3; Label: Flammable Liquid
For occupational chemical analysis use OSHA: #ID-72 or NIOSH: Furfural, 2529.
Furfural is an heterocyclic aldehyde, with the ring structure shown at right. Its chemical formula is OC4H3CHO. It is a colorless oily liquid with the odor of almonds, but upon exposure to air samples quickly become yellow. With the CAS NO. 98-01-1, Furfural dissolves readily in most polar organic solvents, but is only slightly soluble in either water or alkanes. When heated above 250 °C, furfural decomposes into furan and carbon monoxide, sometimes explosively.
Physical properties Furfural are:
(1)ACD/LogP: 0.731; (2)ACD/LogD (pH 5.5): 0.73; (3)ACD/LogD (pH 7.4): 0.73; (4)ACD/BCF (pH 5.5): 2.12; (5)ACD/BCF (pH 7.4): 2.12; (6)ACD/KOC (pH 5.5): 59.53; (7)ACD/KOC (pH 7.4): 59.53; (8)#H bond acceptors:2; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.515; (11)Molar Refractivity: 25.305 cm3; (12)Molar Volume: 83.894 cm3; (13)Polarizability: 10.032 10-24cm3; (14)Surface Tension: 36.5740013122559 dyne/cm; (15)Density: 1.145 g/cm3; (16)Flash Point: 58.333 °C; (17)Enthalpy of Vaporization: 39.837 kJ/mol; (18)Boiling Point: 161.799 °C at 760 mmHg; (19)Vapour Pressure: 2.23399996757507 mmHg at 25°C
Preparation of Furfural:
Many plant materials contain the polysaccharide hemicellulose, a polymer of sugars containing five carbon atoms each. When heated with sulfuric acid, hemicellulose undergoes hydrolysis to yield these sugars, principally xylose. Under the same conditions of heat and acid, xylose and other five carbon sugars undergo dehydration, losing three water molecules to become furfural:
C5H10O5 → C5H4O2 + 3 H2O
Uses of Furfural:
Furfural is used as a solvent in petrochemical refining to extract dienes ( used to make synthetic rubber) from other hydrocarbons . Furfural also can be used either by themselves or in together with phenol, acetone, or urea to make solid resins. It is also used as a chemical intermediate in the production of the solvents furan and tetrahydrofuran.
Safety information of Furfural:
When you are using this chemical, please be cautious about it as the following:(1)In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; (2)Wear suitable protective clothing, gloves and eye/face protection; (3)In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); (4)Keep locked up and out of the reach of children;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H;
(2)InChIKey=HYBBIBNJHNGZAN-UHFFFAOYSA-N;
(3)Smilesc1(ccco1)C=O;
The toxiciy data of Furfural is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LC50 | inhalation | 370ppm/6H (370ppm) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 279, 1969. | |
dog | LD50 | intravenous | 250mg/kg (250mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
dog | LD50 | oral | 950mg/kg (950mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: ATAXIA | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 279, 1969. |
dog | LD50 | subcutaneous | 214mg/kg (214mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
frog | LDLo | parenteral | 23gm/kg (23000mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 21, Pg. 65, 1923. | |
guinea pig | LD50 | oral | 541mg/kg (541mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" BLOOD: HEMORRHAGE | Hygiene and Sanitation Vol. 32(5), Pg. 158, 1967. |
guinea pig | LDLo | subcutaneous | 100mg/kg (100mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
human | TCLo | inhalation | 310ug/m3 (.31mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 26(6), Pg. 3, 1961. | |
mouse | LCLo | inhalation | 370ppm/6H (370ppm) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 279, 1969. | |
mouse | LD50 | intraperitoneal | 102mg/kg (102mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
mouse | LD50 | intravenous | 152mg/kg (152mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
mouse | LD50 | oral | 400mg/kg (400mg/kg) | Biochemical Journal. Vol. 34, Pg. 1196, 1940. | |
mouse | LD50 | subcutaneous | 119mg/kg (119mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
rabbit | LD50 | intramuscular | 78mg/kg (78mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
rabbit | LDLo | oral | 800mg/kg (800mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Pharmacology and Experimental Therapeutics. Vol. 21, Pg. 65, 1923. |
rabbit | LDLo | skin | 620mg/kg (620mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
rabbit | LDLo | subcutaneous | 500mg/kg (500mg/kg) | Hygiene and Sanitation Vol. 32(5), Pg. 158, 1967. | |
rat | LC50 | inhalation | 175ppm/6H (175ppm) | American Industrial Hygiene Association Journal. Vol. 50, Pg. A359, 1989. | |
rat | LC50 | inhalation | 175ppm/6H (175ppm) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | American Industrial Hygiene Association Journal. Vol. 50, Pg. A359, 1989. |
rat | LD50 | intraperitoneal | 20mg/kg (20mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 759, 1978. | |
rat | LD50 | oral | 65mg/kg (65mg/kg) | Bromatologia i Chemia Toksykologiczna. Vol. 13, Pg. 371, 1980. | |
rat | LD50 | subcutaneous | 148mg/kg (148mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 279, 1969. |