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2-Ethylfuran is a clear colorless to yellow liquid with a smoky burnt odor. It has a warm, sweet scent when diluted and exhibits a coffee-like flavor (aroma). 2-Ethylfuran undergoes tetraphenylporphin-photosensitized oxygenation in non-polar aprotic solvents via (4+2)-cycloaddition of singlet oxygen to yield the corresponding monomeric unsaturated secondary ozonide.

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  • 3208-16-0 Structure
  • Basic information

    1. Product Name: 2-Ethylfuran
    2. Synonyms: ETHYLFURAN, 2-;FEMA 3673;a-ethylfuran;2-ETHYL OXOLE;2-ETHYLFURAN;2-ethyl-fura;Furan, alpha-ethyl-;2-ETHYLFURAN 99+%
    3. CAS NO:3208-16-0
    4. Molecular Formula: C6H8O
    5. Molecular Weight: 96.13
    6. EINECS: 221-714-0
    7. Product Categories: API intermediates;Furans;furnan Flavor;Alphabetical Listings;E-F;Flavors and Fragrances;Building Blocks;Heterocyclic Building Blocks
    8. Mol File: 3208-16-0.mol
  • Chemical Properties

    1. Melting Point: -62.8°C (estimate)
    2. Boiling Point: 92-93 °C768 mm Hg(lit.)
    3. Flash Point: 28 °F
    4. Appearance: clear colorless to yellow liquid
    5. Density: 0.912 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 53.9mmHg at 25°C
    7. Refractive Index: n20/D 1.439(lit.)
    8. Storage Temp.: 0-6°C
    9. Solubility: N/A
    10. Sensitive: Air Sensitive
    11. BRN: 105401
    12. CAS DataBase Reference: 2-Ethylfuran(CAS DataBase Reference)
    13. NIST Chemistry Reference: 2-Ethylfuran(3208-16-0)
    14. EPA Substance Registry System: 2-Ethylfuran(3208-16-0)
  • Safety Data

    1. Hazard Codes: F,Xi
    2. Statements: 11
    3. Safety Statements: 16-29-33-9
    4. RIDADR: UN 1993 3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: 3
    9. PackingGroup: II
    10. Hazardous Substances Data: 3208-16-0(Hazardous Substances Data)

3208-16-0 Usage

Uses

Used in Flavor and Fragrance Industry:
2-Ethylfuran is used as a flavoring agent for its warm, sweet, and coffee-like aroma, adding depth and complexity to various food and beverage products.
Used in Chemical Synthesis:
2-Ethylfuran is used as a chemical intermediate in the synthesis of various compounds, such as 4-oxo-(E)-2-hexenal, via ring-opening reactions using aqueous N-bromosuccinimide.
Used in Analytical Chemistry:
2-Ethylfuran is utilized in the investigation of gas phase products formed from the Cl atoms initiated reactions by in situ long-path FTIR absorption spectroscopy, providing valuable insights into the chemical behavior and properties of the compound.
Occurrence:
2-Ethylfuran is a naturally occurring compound found in a variety of food items and beverages, including tomato, coffee, peppermint and spearmint oil, Parmesan cheese, bell pepper, cooked egg, smoked fish, roasted chicken, cooked beef, cocoa, coffee, tea, pecans, filberts, and soybeans.

Preparation

By dehydration of furyl methyl carbinol followed by reduction.

Hazard

Flammable liquid.

Check Digit Verification of cas no

The CAS Registry Mumber 3208-16-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,0 and 8 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3208-16:
(6*3)+(5*2)+(4*0)+(3*8)+(2*1)+(1*6)=60
60 % 10 = 0
So 3208-16-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O/c1-2-6-4-3-5-7-6/h3-5H,2H2,1H3

3208-16-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
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  • Alfa Aesar

  • (A15520)  2-Ethylfuran, 98+%   

  • 3208-16-0

  • 5g

  • 259.0CNY

  • Detail
  • Alfa Aesar

  • (A15520)  2-Ethylfuran, 98+%   

  • 3208-16-0

  • 25g

  • 1222.0CNY

  • Detail
  • Alfa Aesar

  • (A15520)  2-Ethylfuran, 98+%   

  • 3208-16-0

  • 100g

  • 3908.0CNY

  • Detail
  • Aldrich

  • (186988)  2-Ethylfuran  97%

  • 3208-16-0

  • 186988-10G

  • 1,103.31CNY

  • Detail

3208-16-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Ethylfuran

1.2 Other means of identification

Product number -
Other names ETHYLFURAN,2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3208-16-0 SDS

3208-16-0Relevant articles and documents

Amino acid catalysis of 2-alkylfuran formation from lipid oxidation-derived α,β-unsaturated aldehydes

Adams, An,Bouckaert, Capucine,Van Lancker, Fien,De Meulenaer, Bruno,De Kimpe, Norbert

, p. 11058 - 11062 (2011)

The formation of 2-alkylfurans from the corresponding lipid-derived α,β-unsaturated aldehydes under dry-roasting conditions was investigated in detail. The addition of an amino acid to an α,β- unsaturated aldehyde drastically increased 2-alkylfuran formation. Peptides and proteins as well were able to catalyze 2-alkylfuran formation from the corresponding α,β-unsaturated aldehydes. Further investigation of 2-alkylfuran formation showed the need of oxidizing conditions and the involvement of radicals in the reaction. This way, the formation of 2-methylfuran from 2-pentenal, 2-ethylfuran from 2-hexenal, 2-propylfuran from 2-heptenal, 2-butylfuran from 2-octenal, 2-pentylfuran from 2-nonenal, and 2-hexylfuran from 2-decenal was shown. The impact of amino acids on 2-alkylfuran formation from lipid-derived α,β-unsaturated aldehydes represents an interesting example of the complex role of amino acids in the multitude of chemical reactions occurring during thermal processing of lipid-rich foods.

Direct Catalytic Conversion of Biomass-Derived Furan and Ethanol to Ethylbenzene

Teixeira, Ivo F.,Lo, Benedict T. W.,Kostetskyy, Pavlo,Ye, Lin,Tang, Chiu C.,Mpourmpakis, Giannis,Tsang, Shik Chi Edman

, p. 1843 - 1850 (2018/03/09)

Herein, we report a synthetic strategy to convert biomass-derived unsubstituted furan to aromatics at high selectivity, especially to ethylbenzene via alkylation/Diels-Alder cycloaddition using ethanol, while greatly reducing the formation of the main side product, benzofuran, over zeolite catalysts. Using synchrotron X-ray powder diffraction and first-principles calculations, it is shown that the above methodology favors the formation of aromatic products due to ready alkylation of furan by the first ethanol molecule, followed by Diels-Alder cycloaddition with ethylene derived from the second ethanol molecule on a Br?nsted acid site in a one-pot synthesis. This gives a double-promoting effect: an alkyl substituent(s) on furan creates steric hindrance to inhibit self-coupling to benzofuran while an alkylated furan (diene) undergoes a Diels-Alder reaction more favorably due to higher HOMO energy.

Production of p-Methylstyrene and p-Divinylbenzene from Furanic Compounds

Koehle, Maura,Sara?i, Erisa,Dauenhauer, Paul,Lobo, Raul F.

, p. 91 - 98 (2017/01/17)

A four-step catalytic process was developed to produce p-methylstyrene from methylfuran, a biomass-derived species. First, methylfuran was acylated over zeolite H-Beta with acetic anhydride. Second, the acetyl group was reduced to an ethyl group with hydrogen over copper chromite. Third, p-ethyltoluene was formed through Diels–Alder cycloaddition and dehydration of 2-ethyl-5-methyl-furan with ethylene over zeolite H-Beta. Dehydrogenation of p-ethyltoluene to yield p-methylstyrene completes the synthesis but was not investigated because it is a known process. The first two steps were accomplished in high yield (>88 %) and the Diels–Alder step resulted in a 67 % yield of p-ethyltoluene with a 99.5 % selectivity to the para isomer (final yield of 53.5 %). The methodology was also used for the preparation of p-divinylbenzene. It is shown that acylation of furans over H-Beta zeolites is a highly selective and high-yield reaction that could be used to produce other valuable molecules from biomass-derived furans.

Ex situ catalytic upgrading of lignocellulosic biomass components over vanadium contained H-MCM-41 catalysts

Kim, Beom-Sik,Jeong, Chang Seok,Kim, Ji Man,Park, Su Bin,Park, Sung Hoon,Jeon, Jong-Ki,Jung, Sang-Chul,Kim, Sang Chai,Park, Young-Kwon

, p. 184 - 191 (2016/03/08)

H-V-MCM-41 catalysts containing 5, 10, and 30 wt% of vanadium were synthesized and applied to the ex situ catalytic pyrolysis (CP) of three polymeric components of lignocellulosic biomass for the first time. Characterization of the catalysts was performed using N2 adsorption-desorption, XRD, FT-IR, and NH3-TPD. The results of XRD analysis showed that 5 wt% and 10 wt% H-V-MCM-41 catalysts maintained the mesoporous structure, whereas the mesoporous structure was destroyed in 30 wt% H-V-MCM-41 with considerable amount of small V2O5 crystalline outside the framework. NH3-TPD showed that H-V-MCM-41 has mostly weak acid sites and that 10 wt% H-V-MCM-41 had the largest quantity of acid sites due to framework vanadium. In the case of CP of cellulose using Py-GC/MS, 10 wt% H-V-MCM-41 showed the highest catalytic activity for the production of valuable furanic compounds such as furfural because of the enhanced deoxygenation over the acid sites formed on framework vanadium. In the case of CP of xylan as well, 10 wt% H-V-MCM-41 led to the largest yield of mono-aromatics. The production of acetic acid was also promoted by H-V-MCM-41 catalysts. The CP of lignin over H-V-MCM-41 catalysts promoted substantially the production of important feedstock chemicals for the petrochemical industry: phenolics and mono-aromatics.

Model studies on the pattern of volatiles generated in mixtures of amino acids, lipid-oxidation-derived aldehydes, and glucose

Adams, An,Kitryte, Vaida,Venskutonis, Rimantas,De Kimpe, Norbert

experimental part, p. 1449 - 1456 (2011/10/05)

The development of flavor and browning in thermally treated foods results mainly from the Maillard reaction and lipid degradation but also from the interactions between both reaction pathways. To study these interactions, we analyzed the volatile compounds resulting from model reactions of lysine or glycine with aldehydes originating from lipid oxidation [hexanal, (E)-2-hexenal, or (2E,4E)-decadienal] in the presence and absence of glucose. The main reaction products identified in these model mixtures were carbonyl compounds, resulting essentially from amino-acid-catalyzed aldol condensation reactions. Several 2-alkylfurans were detected as well. Only a few azaheterocyclic compounds were identified, in particular 5-butyl-2-propylpyridine from (E)-2-hexenal model systems and 2-pentylpyridine from (2E,4E)-decadienal model reactions. Although few reaction products were found resulting from the condensation of an amino acid with a lipid-derived aldehyde, the amino acid plays an important role in catalyzing the degradation and further reaction of these carbonyl compounds. These results suggest that amino-acid-induced degradations and further reactions of lipid oxidation products may be of considerable importance in thermally processed foods.

Preparation of unsymmetrical dialkyl acetylenedicarboxylates and related esters by enzymatic transesterification

Sultan, Nisrine,Thomas, Coralie,Blanco, Luis,Deloisy, Sandrine

body text, p. 3443 - 3446 (2011/06/27)

An unexpected highly selective mono-transesterification of symmetrical acetylenedicarboxylates with various alcohols occurred in the presence of Candida rugosa lipase. This reaction allows an efficient preparation of unsymmetrical acetylenedicarboxylates and related α,β-acetylenic esters.

(2E)-4-hydroxyalk-2-enals and 2-substituted furans as products of reactions of (2E)-4,4-dimethoxybut-2-enal with Grignard compounds

Garibyan,Ovanesyan,Makaryan,Petrosyan,Chobanyan

experimental part, p. 406 - 409 (2010/09/12)

Methods have been developed for the synthesis of (2E)-1,1-dimethoxyalk-2- en-4-ols and (2E)-4-hydroxyalk-2-enals by reaction of (2E)-4,4-dimethoxybut-2- enals and Grignard compounds. Thermal isomerization of (2E)-4-hydroxyalk-2-enals gave the corresponding 2-alkylfurans.

Polymer pyrolysis and oxidation studies in a continuous feed and flow reactor: Cellulose and polystyrene

Park, Byung-Ik,Bozzelli, Joseph W.,Booty, Michael R.,Bernhard, Mary J.,Mesuere, Karel,Pettigrew, Charles A.,Shi, Ji-Chun,Simonich, Staci L.

, p. 2584 - 2592 (2007/10/03)

A dual-zone, continuous feed tubular reactor is developed to assess the potential for formation of products from incomplete combustion in thermal oxidation of common polymers. Solid polymer (cellulose or polystyrene) is fed continuously into a volatilization oven where it fragments and vaporizes. The gas-phase polymer fragments flow directly into a second, main flow reactor to undergo further reaction. Temperatures in the main flow reactor are varied independently to observe conditions needed to convert the initial polymer fragments to CO2 and H2O. Combustion products are monitored at main reactor temperatures from 400 to 850 °C and at 2.0-s total residence time with four on-line GC/FIDs; polymer reaction products and intermediates are further identified by GC/MS analysis. Analysis of polymer decomposition fragments at 400 °C encompasses complex oxygenated and aromatic hydrocarbon species, which range from high-molecular-weight intermediates of ca. 300 amu, through intermediate mass ranges down to C1 and C2 hydrocarbons, CO, and CO2. Approximately 41 of these species are positively identified for cellulose and 52 for polystyrene. Products from thermal oxidation of cellulose and polystyrene are shown to achieve complete combustion to CO2 and H2O at a main reactor temperature of 850 °C under fuel-lean equivalence ratio and 2.0-s reaction time. A dual-zone, continuous feed tubular reactor is developed to assess the potential for formation of products from incomplete combustion in thermal oxidation of common polymers. Solid polymer (cellulose or polystyrene) is fed continuously into a volatilization oven where it fragments and vaporizes. The gas-phase polymer fragments flow directly into a second, main flow reactor to undergo further reaction. Temperatures in the main flow reactor are varied independently to observe conditions needed to convert the initial polymer fragments to CO2 and H2O. Combustion products are monitored at main reactor temperatures from 400 to 850°C and at 2.0-s total residence time with four on-line GC/FIDs; polymer reaction products and intermediates are further identified by GC/MS analysis. Analysis of polymer decomposition fragments at 400°C encompasses complex oxygenated and aromatic hydrocarbon species, which range from high-molecular-weight intermediates of ca. 300 amu, through intermediate mass ranges down to C1 and C2 hydrocarbons, CO, and CO2. Approximately 41 of these species are positively identified for cellulose and 52 for polystyrene. Products from thermal oxidation of cellulose and polystyrene are shown to achieve complete combustion to CO2 and H2O at a main reactor temperature of 850°C under fuel-lean equivalence ratio and 2.0-s reaction time.

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