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HomeProduct name list3-Bromofuran

3-Bromofuran

  • CAS NO.:22037-28-1
  • Empirical Formula: C4H3BrO
  • Molecular Weight: 146.97
  • MDL number: MFCD00005347
  • EINECS: 244-744-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-05-18 08:51:53
3-Bromofuran Structural

What is 3-Bromofuran?

Chemical properties

3-Bromofuran is a colorless to light yellow liquid having a boiling point similar to that of water (102.5-102.6 °C), but with density significantly higher (1.6606 g/cm3 at 20 °C).It is colorless when it is pure; however, the color can be light yellow when minor impurities are present. It is usaually stablized by calcium carbonate. It was used in the preparation of 2-substituted 3-furfurals. It was also used in the synthesis of 5,6-dehydronorcantharidins. 3-bromofuran is one of the volatile metabolites discussed in studies for detecting and discriminating diseases of onion.

The Uses of 3-Bromofuran

3-Bromofuran is heterocyclic building block used in organic synthesis. 3-Bromofuran is one of the volatile metabolites discussed in studies for detecting and discriminating diseases of onion.

What are the applications of Application

3-Bromofuran is a synthesis reagent used in the preparation of various chemicals

Synthesis

3-Bromofuran was obtained in minor amounts in 1887 as a byproduct in a reaction of 3-bromofuroic acid with calcium hydroxide. About four decades later this compound was prepared deliberately and in higher yield. 3-bromofuran has been prepared from 3,4-dibromofuran via ortho-metalation with butyl lithium in good yield. An elegant synthesis of 3-bromofuran is due to Fechtel who prepared this compound via a Diels Alder-bromination-reverse Diels Alder sequence.

Purification Methods

Purify 3-bromofuran by two steam distillations and dry it over fresh CaO. It can be dried over Na metal (no obvious reaction) and fractionated. It is not very soluble in H2O but is soluble in organic solvents. When freshly distilled, it is a clear oil, but darkens on standing and eventually resinifies. It can be stored for long periods by covering the oil with an alkaline solution of hydroquinone and is redistilled when required. It forms a characteristic maleic anhydride adduct, m 131.5-132o. [Shepard et al. J Am Chem Soc 52 2083 1930, Huhes & Johnson J Am Chem Soc 53 737 1931, adduct: van Campen & Johnson J Am Chem Soc 55 430 1933, Beilstein 17/1 V 295.]

Properties of 3-Bromofuran

Melting point: 131.5-132 °C
Boiling point: 103 °C (lit.)
Density  1.635 g/mL at 25 °C (lit.)
refractive index  n20/D 1.496(lit.)
Flash point: 38 °F
storage temp.  -20°C
solubility  Chloroform, Ethyl Acetate
form  Liquid
color  Clear yellow to orange to brown
Water Solubility  Soluble in chloroform, ethyl acetate. Insoluble in water.
BRN  105337
InChI InChI=1S/C4H3BrO/c5-4-1-2-6-3-4/h1-3H
CAS DataBase Reference 22037-28-1(CAS DataBase Reference)
NIST Chemistry Reference Furan, 3-bromo-(22037-28-1)

Safety information for 3-Bromofuran

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
GHS Hazard Statements H225:Flammable liquids
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P240:Ground/bond container and receiving equipment.
P241:Use explosion-proof electrical/ventilating/lighting/…/equipment.
P242:Use only non-sparking tools.
P243:Take precautionary measures against static discharge.

Computed Descriptors for 3-Bromofuran

InChIKey LXWLEQZDXOQZGW-UHFFFAOYSA-N
SMILES O1C=CC(Br)=C1

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