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2,3-dihydrofuran
furan, 2,3-dihydro-

Supplier Sponsors

Name:2,3-dihydrofuran
CAS Number: 1191-99-7Picture of molecule3D/inchi
Other(deleted CASRN):27535-65-5
ECHA EINECS - REACH Pre-Reg:214-747-7
FDA UNII: 07M2EY3BG1
Nikkaji Web:J41.161B
Beilstein Number:0103168
MDL:MFCD00003205
XlogP3-AA:0.80 (est)
Molecular Weight:70.09102000
Formula:C4 H6 O
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 97.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.92700 @ 25.00 °C.
Refractive Index:1.42300 @ 20.00 °C.
Boiling Point: 54.00 to 55.00 °C. @ 760.00 mm Hg
Vapor Pressure:14.460000 mmHg @ 55.00 °C.
Flash Point: -4.00 °F. TCC ( -20.00 °C. )
logP (o/w): -0.034 (est)
Soluble in:
 alcohol
 water, 3.273e+004 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2,3-dihydrofuran 95%
EMD Millipore
For experimental / research use only.
2,3-Dihydrofuran
Penta International
2,3-DIHYDROFURAN
Santa Cruz Biotechnology
For experimental / research use only.
2,3-Dihydrofuran
Sigma-Aldrich: Aldrich
For experimental / research use only.
2,3-Dihydrofuran 99%
TCI AMERICA
For experimental / research use only.
2,3-Dihydrofuran >98.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 19 - May form explosive peroxides.
R 22 - Harmful if swallowed.
R 36 - Irritating to eyes.
S 01/02 - Keep locked up and out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 33 - Take precautionary measures against static discharge.
S 37/39 - Wear suitable gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for 2,3-dihydrofuran usage levels up to:
 not for fragrance use.
 
Recommendation for 2,3-dihydrofuran flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1191-99-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :70934
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1993
WGK Germany:3
2,3-dihydrofuran
Chemidplus:0001191997
 
References:
 2,3-dihydrofuran
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):70934
Pubchem (sid):135026234
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2932.19.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 wine
Search Picture
 
Synonyms:
2,3-DHF
2,3-dihydro-furan
 furan, 2,3-dihydro-
 

Articles:

PubMed:Palladium catalyzed heck arylation of 2,3-dihydrofuran-effect of the palladium precursor.
PubMed:Metabolic profiling framework for discovery of candidate diagnostic markers of malaria.
PubMed:Design, synthesis, and structure-activity relationships of dihydrofuran-2-one and dihydropyrrol-2-one derivatives as novel benzoxazin-3-one-based mineralocorticoid receptor antagonists.
PubMed:Organocatalyzed anion relay leading to functionalized 2,3-dihydrofurans.
PubMed:Libraries of bisdiazaphospholanes and optimization of rhodium-catalyzed enantioselective hydroformylation.
PubMed:Inner workings of a cinchona alkaloid catalyzed oxa-Michael cyclization: evidence for a concerted hydrogen-bond-network mechanism.
PubMed:Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran--effect of prolinate salts.
PubMed:Time resolved infrared spectroscopy: kinetic studies of weakly binding ligands in an iron-iron hydrogenase model compound.
PubMed:Phosphine-catalyzed domino reaction for the synthesis of conjugated 2,3-dihydrofurans from allenoates and Nazarov reagents.
PubMed:Highly selective asymmetric Rh-catalyzed hydroformylation of heterocyclic olefins.
PubMed:Bicunningines A and B, two new dimeric diterpenes from Cunninghamia lanceolata.
PubMed:Functionalized 2,3-dihydrofurans via palladium-catalyzed oxyarylation of α-allyl-β-ketoesters.
PubMed:Domino reactions consisting of heterocyclization and 1,2-migration-redox-neutral and oxidative transition-metal catalysis.
PubMed:BINAP versus BINAP(O) in asymmetric intermolecular Mizoroki-Heck reactions: substantial effects on selectivities.
PubMed:β-(Trifluoromethyl)vinyl sulfonium salts: preparation and reactions with active methylene and methenyl compounds.
PubMed:Formation mechanism of furfuryl sulfides from o-furfuryl dithiocarbonates: density functional theory study for aromatic [3,3]-sigmatropic rearrangement.
PubMed:Novel biodegradation pathways of cyclohexane by Rhodococcus sp. EC1.
PubMed:A cascade process for the synthesis of gem-difluoromethylene compounds.
PubMed:Mechanism of resistance to GS-9148 conferred by the Q151L mutation in HIV-1 reverse transcriptase.
PubMed:Phosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction.
PubMed:Facile domino access to chiral mono-, bi-, and tricyclic 2,3-dihydrofurans.
PubMed:Furan approach to vitamin D analogues. Synthesis of the A-ring of calcitriol and 1α-hydroxy-3-deoxyvitamin D(3).
PubMed:An integrated microreactor system for self-optimization of a Heck reaction: from micro- to mesoscale flow systems.
PubMed:Adsorption and reactivity of 2,3-dihydrofuran and 2,5-dihydrofuran on Pd(111): influence of the C=C position on the reactivity of cyclic ethers.
PubMed:Construction of 2,3-dihydrofuran cores through the [3+2] cycloaddition of gold alpha-carbonylcarbenoids with alkenes.
PubMed:Copper(II)-catalyzed highly diastereoselective three-component reactions of aryl diazoacetates with alcohols and chalcones: an easy access to furan derivatives.
PubMed:Efficient and highly selective method for the synthesis of benzo(naphtho)quinoline derivatives catalyzed by iodine.
PubMed:Cyclobutane amino acid analogues of furanomycin obtained by a formal [2 + 2] cycloaddition strategy promoted by methylaluminoxane.
PubMed:Diastereoselective synthesis of trans-2,3-dihydrofurans with pyridinium ylide assisted tandem reaction.
PubMed:Displacement kinetics of eta(2)-bound furan and 2,3-dihydrofuran from Mn and Cr centers: evidence for the partial dearomatization of the furan ligand.
PubMed:Unexpected Pd-catalyzed coupling, propargyl-allenyl isomerization and alder-ene reaction: facile synthesis of some not readily available 2,3-dihydrofuran derivatives.
PubMed:Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives.
PubMed:Vinylic C--H borylation of cyclic vinyl ethers with bis(pinacolato)diboron catalyzed by an Iridium(I)-dtbpy complex.
PubMed:Ring-enlargement of dimethylaminopropenoyl cyclopropanes: an efficient route to substituted 2,3-dihydrofurans.
PubMed:Pd-catalyzed sequential reactions via allene intermediate for the synthesis of polycyclic frameworks containing 2,3-dihydrofuran units.
PubMed:A gold(I)-catalyzed intramolecular reaction of propargylic/homopropargylic alcohols with oxirane.
PubMed:A dramatic switch of enantioselectivity in asymmetric heck reaction by benzylic substituents of ligands.
PubMed:Efficient synthesis of (3R,3aS,6aR)- hexahydrofuro[2,3-b]furan-3-ol from glycolaldehyde.
PubMed:Putative structure and characteristics of a red water-soluble pigment secreted by Penicillium marneffei.
PubMed:1-Oxo-5-hydroxytryptamine: a surprisingly potent agonist of the 5-HT3 (serotonin) receptor.
PubMed:Enantio- and regioselective heck-type reaction of arylboronic acids with 2,3-dihydrofuran.
PubMed:A metathesis-based approach to the synthesis of furans.
PubMed:Copper-catalyzed asymmetric [4+1] cycloadditions of enones with diazo compounds to form dihydrofurans.
PubMed:Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides.
PubMed:Kinetics of proton transfer from benzo[b]-2,3-dihydrofuran-2-one and benzo[b]-2,3-dihydrothiophene-2-one. Effect of anion aromaticity on intrinsic barriers.
PubMed:The reaction of phenyl radical with molecular oxygen: a G2M study of the potential energy surface.
PubMed:An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium-catalyzed multi-component domino reaction.
PubMed:Synthesis of 2,3-trans disubstituted tetrahydrofurans through sequential xanthate radical addition-substitution reactions.
PubMed:Iridium complex-catalyzed [2+2+2] cycloaddition of alpha,omega-diynes with monoynes and monoenes.
PubMed:An efficient carbonyl-alkene metathesis of bicyclic oxetanes: photoinduced electron transfer reduction of the Paternò-Büchi adducts from 2,3-dihydrofuran and aromatic aldehydes.
PubMed:Regio- and stereoselective homocoupling of gamma-arylated tert-propargyl alcohols with liberation of a ketone molecule and successive cyclization to produce fluorescent dihydrofuran derivatives.
PubMed:Regioselective synthesis of trisubstituted 2,3-dihydrofurans from donor-acceptor cyclopropanes or from reaction of the Corey ylide with alpha-sulfenyl-, alpha-sulfinyl-, or alpha-sulfonylenones.
PubMed:Short, enantioselective total synthesis of aflatoxin B2 using an asymmetric [3+2]-cycloaddition step.
PubMed:Kishner's reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran, a highly reactive ene in the ene reaction.
PubMed:First successful application of diphosphite ligands in the asymmetric hydroformylation of dihydrofurans.
PubMed:Inhibition of diethyl ether degradation in Rhodococcus sp. strain DEE5151 by glutaraldehyde and ethyl vinyl ether.
PubMed:Substantial (2)h-magnetic isotope effects on the diastereoselectivity of triplet photocycloaddition reactions.
PubMed:Zirconium-mediated coupling reactions of amines and enol or allyl ethers: synthesis of allyl- and homoallylamines.
PubMed:Asymmetric dearomatization of the furan ring promoted by conjugate organolithium addition to (menthyloxy)(3-furyl)carbene complexes of chromium.
PubMed:Asymmetric synthesis of oxygen heterocycles via Pd-catalyzed dynamic kinetic asymmetric transformations: application to nucleosides.
PubMed:Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement.
PubMed:Domino reactions of 4,5-dicyanopyridazine with dihydroheterocycles: synthetic and mechanistic features.
PubMed:Synthesis and antiviral activity of novel erythrofuranosyl imidazo[1,2-a]pyridine C-nucleosides constructed via palladium coupling of iodoimidazo[1,2-a]pyridines and dihydrofuran.
PubMed:Uncatalyzed [4 + 2] cycloadditions of 3-nitrocoumarins with vinyl ethers in solventless conditions. A new entry to chromene derivatives.
PubMed:Asymmetric synthesis of anti-homopropargylic alcohols from aldehydes and chiral sulfonimidoyl substituted bis(allyl)titanium complexes through generation and elimination of novel chiral alkylidenecarbene (dimethylamino)sulfoxonium ylides.
PubMed:Germination inhibitory constituents from Erigeron annuus.
PubMed:Comparison of oxygen and sulfur effects on keto-enol chemistry in benzolactone systems: benzo[b]-2,3-dihydrofuran-2-one and -2-thione and benzo[b]-2,3-dihydrothiophene-2-one and -2-thione.
PubMed:InCl(3)-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water: a highly efficient synthesis of new 1,2,3,4-tetrahydroquinoline derivatives.
PubMed:Pectenotoxin-2 synthetic studies. 1. Alkoxide precoordination to [Rh(NBD)(DIPHOS-4)]BF(4) allows directed hydrogenation of a 2,3-dihydrofuran-3-ol without competing furan production.
PubMed:Photo- and radiation-chemical formation and electrophilic and electron transfer reactivities of enolether radical cations in aqueous solution.
PubMed:Highly Enantioselective Intermolecular Cu(I)-Catalyzed Cyclopropanation of Cyclic Enol Ethers. Asymmetric Total Synthesis of (+)-Quebrachamine.
PubMed:Carbonylation of Alkynyl Epoxides: Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives.
PubMed:Methanol addition to dihapto-coordinated rhenium complexes of furan.
PubMed:Spin-directed stereoselectivity of carbonyl-alkene photocycloadditions
PubMed:Synthesis, resolution, and applications of 2, 2'-bis(diphenylphosphino)-3,3'- binaphtho[2,1-b]furan.
PubMed:Quinone approaches toward the synthesis of aflatoxin B(2).
PubMed:Reactivity of Cl-P(+)-Cl toward cyclic organic ethers.
PubMed:Synthesis and biological investigations of 1-(tetrahydropyran-2'-yl)- and 1-(tetrahydrofuran-2'-yl)benzimidazoles and 1/2-(tetrahydropyran-2'-yl)- and 1/2-(tetrahydrofuran-2'-yl)benzotriazoles.
PubMed:2-Methyl-3-oxo-4-phenyl-2,3-dihydrofuran-2-yl acetate: a fluorogenic reagent for detection and analysis of primary amines.
PubMed:Asymmetric Hydroformylation of Heterocyclic Olefins Catalyzed by Chiral Phosphine-Phosphite-Rh(I) Complexes.
PubMed:The Millimeter-Wave Spectrum of 2,3-Dihydrofuran
PubMed:Reactions of alpha-acetoxy-N-nitrosopyrrolidine and alpha-acetoxy-N-nitrosopiperidine with deoxyguanosine: formation of N2-tetrahydrofuranyl and N2-tetrahydropyranyl adducts.
PubMed:Novel synthesis of cholesterol analogs: condensation of pregnenolone with dihydropyran or dihydrofuran.
PubMed:Toxicity of alkyldihydrofurans to metabolically active organs in the mouse.
PubMed:Identification of the n-heptane metabolites in rat and human urine.
PubMed:Methodological investigations on the determination of n-hexane metabolites in urine.
PubMed:Synthesis and pharmacological activity of some 2,3-dihydrofuran-2,3-dione derivatives.
PubMed:Synthesis and biological activities of ftorafur metabolites. 3'- and 4'-hydroxyftorafur.
PubMed:The synthesis of amino acids from 2,3-dihydrofuran DL-ornithine, DL-proline, and DL-alpha-amino-delta-hydroxyvaleric acid.
 
Notes:
None found
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