Benzofuran

Benzofuran Basic information
Product Name:Benzofuran
Synonyms:1-BENZOFURAN;2,3-Benzofuran, GC 99%;Coumarone;Benzo[b]furan, 99+%;Benzobüfuran, 99+%;2,3-Benzofuran ,97%;Benzo[b]furan 98%;2,3-Benzofuran, 99.5%
CAS:271-89-6
MF:C8H6O
MW:118.14
EINECS:205-982-6
Product Categories:Pyridines;Furan&Benzofuran;Benzofurans;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
Mol File:271-89-6.mol
Benzofuran Structure
Benzofuran Chemical Properties
Melting point <-18℃
Boiling point 173-175 °C(lit.)
density 1.095 g/mL at 20 °C(lit.)
refractive index n20/D 1.567
Fp 133 °F
storage temp. 2-8°C
solubility soluble in Dichloromethane
pka33.2
form Crystalline Powder or Crystals
color Yellow to green to yellow-brown
Water Solubility insoluble
Merck 14,1088
BRN 107704
LogP2.670
CAS DataBase Reference271-89-6(CAS DataBase Reference)
IARC2B (Vol. 63) 1995
NIST Chemistry ReferenceBenzofuran(271-89-6)
EPA Substance Registry SystemBenzofuran (271-89-6)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 40-52-10
Safety Statements 36/37-16
RIDADR UN 1993 3/PG 3
WGK Germany 3
RTECS DF6423800
10-23
Hazard Note Irritant
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29329900
Hazardous Substances Data271-89-6(Hazardous Substances Data)
ToxicityIsolated from coal oil and used in the manufacture of coumarone-indene resin. This resin is used in paints, glue, etc. and is allowed in food packaging. Little is known about the toxicity of benzofuran to humans but acute toxicity in experimental animals involves liver and kidney failure. Chronic toxicity to animals involves damage to the liver, kidneys, lungs, and stomach. Lifetime administration (oral administration) caused cancer in both rats and mice.
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Benzofuran Usage And Synthesis
Chemical Properties2,3-Benzofuran is a colorless, sweet-smelling, oily liquid made by processing coal into coal oil. It may also be formed during other uses of coal or oil. 2,3-Benzofuran is not used for any commercial purposes, but the part of the coal oil that contains 2,3-benzofuran is made into a plastic called coumarone-indene resin. This resin resists corrosion and is used to make paints and varnishes. The resin also provides water resistance and is used in coatings on paper products and fabrics. It is used as an adhesive in food containers and some asphalt fl oor tiles. The resin has been approved for use in food packages and as a coating on citrus fruits. We do not know how often the resin is used or whether any 2,3-benzofuran in the coating or packaging gets into the food. 2,3-Benzofuran may enter the air, water, and soil during its manufacture, use, or storage at hazardous waste sites. Breathing contaminated air or touching the chemical in the workplace is the source of human exposure.
Usesmanufacture of coumarone-indene resins.
UsesAs an intermediate in the polymerization of coumarone-indene resins found in various corrosion-resistant coatings such as paints and varnishes; in water-resistant coatings for paper products and fabrics; in adhesives for use in food containers
UsesBenzo[b]furan is used in the manufacture of coumarone-indene resin. It has been used to make floor tiles and other products. It is also used as a coating on grapefruit, lemons, lirnes, oranges, tangelos and tangerines and in the production of COITosion-resistant paints and varnishes, in water-resistant coatings on paper products and fabrics and as adhesives in food containers.
DefinitionA bicyclic ring compound derived from coal tar naphtha, the parent substance of coumarone-indene resins.
Synthesis Reference(s)The Journal of Organic Chemistry, 44, p. 28, 1979 DOI: 10.1021/jo01315a008
General DescriptionClear oily yellow liquid with an aromatic odor.
Air & Water ReactionsHighly flammable. May be sensitive to prolonged exposure to air. Very slightly water soluble.
Reactivity ProfileBenzofuran slowly polymerizes on standing. Benzofuran may be sensitive to prolonged exposure to air. Benzofuran is polymerized by H2SO4.
HazardPossible carcinogen.
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition Benzofuran emits acrid and irritating smoke and fumes.
Health HazardRats and mice that ingested high levels of 2,3-benzofuran over a short time had liver and kidney damage. Those exposed over a long time to moderate levels had liver, kidney, lung, and stomach damage. In one study, the ability of animals to reproduce was not affected. We do not know if people will experience health effects similar to those seen in animals.
Fire HazardBenzofuran is combustible.
CarcinogenicityBenzofuran was not mutagenic in bacterial assays but did cause chromosomal aberrations and sister chromatid exchanges in cultured rodent cells.
Purification MethodsBenzofuran is steam distilled, dissolved in Et2O, washed with 5% aqueous NaOH, saturated NaCl, dried (Na2SO4), evaporated and redistilled. UV: max 245, 275, 282nm (log 4.08, 3.45, 3.48). The picrate has m 102-103o. [Burgstahler & Worden Org Synth Coll Vol V 251 1973, NMR: Black & Heffernan Aust J Chem 18 353 1965, Beilstein 17/2 V 3.]
Dibenzofuran 2-Methylcumarone TRIOXSALEN COUMESTROL FURFURYL ALCOHOL RESIN Psoralen 2-Butylbenzofuran Carbofuran KHELLIN Benzo[b]thien-2-ylboronic acid VISNAGIN 1-BENZOFURAN-2-CARBOXYLIC ACID 8-Methoxypsoralen Tetrahydrofuran Nitrofurantoin 1-BENZOFURAN-2-CARBALDEHYDE,1-BENZOFURAN-2-CARBOXALDEHYDE Furazolidone 5-Bromo-1-benzofuran

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