2-Ethynylfuran supplier | CasNO.18649-64-4

Name
3-ETHYNYL-2-HYDROXY-PHENOL
EINECS
CAS No. 18649-64-4
Article Data17
CAS DataBase
Density 1.03 g/cm³
Solubility
Melting Point
Formula C₆H₄O
Boiling Point 106.32 °C at 760 mmHg
Molecular Weight 92.0972
Flash Point 12.171 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-ETHYNYL-2-HYDROXY-PHENOL;3-ETHYNYL-BENZENE-1,2,DIOL;Furan, 2-ethynyl-;2-Ethynylfur
PSA 13.14000
LogP 1.26090

Synthetic route

: 40231-01-4
(furan-2-ylethynyl)-trimethylsilane

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 18h; Cooling with ice; Inert atmosphere;	98.9%
With potassium carbonate In methanol at 20℃; for 18h; Inert atmosphere;

: 100074-10-0
2,2-dibromovinyl-2-furan

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
Stage #1: 2,2-dibromovinyl-2-furan With methyllithium In diethyl ether at -78 - 20℃; Stage #2: With water; ammonium chloride In diethyl ether	47%
With methyllithium; hydrogen cation 1.) ether, a.) -78 deg C, 1 h; b.) up to RT; c.) RT, 1 h; 2.) ether; Yield given. Multistep reaction;
With n-butyllithium In hexane at -78 - 20℃; for 5h;

: 26480-96-6
α-(2-furoyl)-α-(ethoxycarbonyl)methylenetriphenylphosphorane

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
at 750℃; under 0.1 - 1 Torr;	40%

: 1487-18-9
(furan-2-yl)ethylene

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With diethyl ether; bromine at -20℃; Behandeln des Reaktionsprodukts mit aethanol. Kalilauge;

: 539-47-9
3-(fur-2-yl)crotonic acid

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With bromine Erwaermen der erhaltenen 2,3-Dibrom-3-<2>furyl-propionsaeure mit wss. Alkalilauge;

: 98-01-1
furfural

: 27491-70-9, 28447-24-7, 25411-73-8
dimethyl diazomethylphosphonate

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With potassium tert-butylate 1.) THF, -78 deg C, 5 min, 2.) 8 h; Yield given. Multistep reaction;

: 178173-83-6
4-Furan-2-yl-2-methyl-but-3-yn-2-ol

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With potassium hydroxide In paraffin under 1 Torr; for 0.5h; Heating; Yield given;

: 54829-48-0
2-iodofuran

: 4301-14-8
acetylenemagnesium bromide

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); zinc dibromide In tetrahydrofuran at 22 - 23℃; for 1h;	92 % Chromat.

α-bromo-α--ethylene: α-bromo-α--ethylene

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With potassium hydroxide

β-bromo-α--ethylene: β-bromo-α--ethylene

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With potassium hydroxide

: 527-69-5
2-furancarbonyl chloride

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / Et3N / toluene / 3 h / Ambient temperature 2: 40 percent / 750 °C / 0.1 - 1 Torr View Scheme

: 98-01-1
furfural

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) triphenylphosphine (PPh3), Zn dust / 1.) CH2Cl2, RT, 38 h; 2.) CH2Cl2, a.) 0 deg C; b.) RT, 6 h 2: 1.) 2.3M methyllithium, 2.) H(1+) / 1.) ether, a.) -78 deg C, 1 h; b.) up to RT; c.) RT, 1 h; 2.) ether View Scheme
Multi-step reaction with 2 steps 1.1: triphenylphosphine; zinc / dichloromethane / 24 h / 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: triphenylphosphine; zinc / dichloromethane / 41 h / 20 °C 1.2: 6 h / 20 °C 2.1: methyllithium / diethyl ether / -78 - 20 °C View Scheme

: 98-01-1
furfural

: 21047-57-4
diethyl (1-diazo-2-oxopropyl)phosphonate

: 18649-64-4
2-ethynylfuran

Conditions

Conditions	Yield
With caesium carbonate In ethanol at 0℃;

: 81959-36-6
2-(2-bromovinyl)furan

A: 18649-64-4
2-ethynylfuran

B: 138572-96-0
(E)-2-(2-bromoethenyl)furan

Conditions

Conditions	Yield
With sodium hydroxide In isopropyl alcohol for 1.5h; Reflux;	A n/a B 2.51 g

: 18649-64-4
2-ethynylfuran

: 4-methoxy-2-trifluoroacetyl-aniline ring propyl formate

: C16H10F3NO4

Conditions

Conditions	Yield
With piperidine; (1R,2R)-3-(tert-butyldimethylsilyloxy)-2-(N-pyrrolidinyl)-1-nitrophenyl-1-propanol; zinc(II) tosylate In n-heptane; benzene at 25℃; Reflux;	95%

: 18649-64-4
2-ethynylfuran

: 103-72-0
phenyl isothiocyanate

: 71535-50-7
N-tosyl-2-benzylaziridine

: 5-benzyl-3-(furan-2-ylmethylene)-N-phenyl-4-tosylthiomorpholin-2-imine

Conditions

Conditions	Yield
With copper(l) iodide; 1,1,1,3',3',3'-hexafluoro-propanol at 25 - 60℃; for 14h; Molecular sieve; regioselective reaction;	93%

...Expand

: 18649-64-4
2-ethynylfuran

: 71535-50-7
N-tosyl-2-benzylaziridine

: 4-benzyl-2-[furan-2-ylmethylene]-3-tosylthiazolidine

Conditions

Conditions	Yield
Stage #1: 2-ethynylfuran With sulfur; copper diacetate; sodium L-ascorbate In water; tert-butyl alcohol at 25℃; for 0.5h; Stage #2: N-tosyl-2-benzylaziridine In water; tert-butyl alcohol at 80℃; for 22h; regioselective reaction;	92%

: 18649-64-4
2-ethynylfuran

: 100074-11-1
1,4-di(furan-2-yl)buta-1,3-diyne

Conditions

Conditions	Yield
With triethylamine; chloroacetone; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene Ambient temperature;	90%
With 1,10-Phenanthroline; tetrabutylammonium dichloroaurate(I); [bis(acetoxy)iodo]benzene In acetonitrile at 50℃;	90%
With oxygen; copper(l) chloride In pyridine at 20 - 40℃;
With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(l) chloride In acetone

: 18649-64-4
2-ethynylfuran

: 98-88-4
benzoyl chloride

: 142354-42-5
1-(furan-2-yl)-3-phenylpropynone

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine at 50℃; for 6h; Inert atmosphere; Schlenk technique;	90%

: 18649-64-4
2-ethynylfuran

: 2739-97-1
pyridine-2-acetonitrile

: 124-38-9
carbon dioxide

: C14H8N2O2

Conditions

Conditions	Yield
Stage #1: 2-ethynylfuran; carbon dioxide With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	90%

...Expand

: 18649-64-4
2-ethynylfuran

: 75-15-0
carbon disulfide

: 71535-50-7
N-tosyl-2-benzylaziridine

: 5-benzyl-3-(furan-2-ylmethylene)-4-tosylthiomorpholine-2-thione

Conditions

Conditions	Yield
Stage #1: 2-ethynylfuran With N-ethyl-N,N-diisopropylamine; silver(I) iodide In N,N-dimethyl-formamide at 25℃; for 0.5h; Schlenk technique; Molecular sieve; Inert atmosphere; Stage #2: carbon disulfide; N-tosyl-2-benzylaziridine In N,N-dimethyl-formamide at 70℃; for 16h; Schlenk technique; Molecular sieve; Inert atmosphere;	90%

...Expand

: 18649-64-4
2-ethynylfuran

: 622-79-7
benzyl azide

: 1-benzyl-4-(2-furanyl)-1,2,3-triazole

Conditions

Conditions	Yield
With copper(l) iodide at 20℃; for 0.5h;	90%

: 18649-64-4
2-ethynylfuran

: 100-39-0
benzyl bromide

: 1-benzyl-4-(2-furanyl)-1,2,3-triazole

Conditions

Conditions	Yield
With copper(l) iodide; sodium azide at 20℃; for 0.5h;	90%

: 18649-64-4
2-ethynylfuran

: 109-77-3
malononitrile

: 693-13-0
diisopropyl-carbodiimide

: (4Z,5Z)-2-amino-4-(furan-2-ylmethylene)-1-isopropyl-5-(isopropylimino)-4,5-dihydro-1H-pyrrole-3-carbonitrile

Conditions

Conditions	Yield
Stage #1: 2-ethynylfuran; diisopropyl-carbodiimide With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetra-n-butylphosphonium acetate In acetonitrile at 25℃; for 0.5h; Molecular sieve; Inert atmosphere; Stage #2: malononitrile In acetonitrile at 80℃; for 16h; Inert atmosphere; Molecular sieve;	89%

...Expand

: 18649-64-4
2-ethynylfuran

: 762-42-5
dimethyl acetylenedicarboxylate

: 693-13-0
diisopropyl-carbodiimide

: dimethyl 4‑(furan‑2‑yl)‑1‑isopropyl‑6‑(isopropylimino)‑1,6‑dihydropyridine‑2,3‑dicarboxylate

Conditions

Conditions	Yield
Stage #1: 2-ethynylfuran; diisopropyl-carbodiimide With copper(l) iodide; tetra-n-butylphosphonium acetate In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: dimethyl acetylenedicarboxylate In tetrahydrofuran at 25℃; for 16h; Schlenk technique; Inert atmosphere;	89%

...Expand

: 18649-64-4
2-ethynylfuran

: 251549-57-2
2-benzenesulfonylamino-3-iodo-5-methylthiopyridine

: 2-(furan-2-yl)-5-methylthio-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In 1,4-dioxane at 60℃; for 1h;	85%

: 18649-64-4
2-ethynylfuran

: 122-60-1
Phenyl glycidyl ether

: 103-72-0
phenyl isothiocyanate

: 2-(furan-2-ylmethylene)-6-(phenoxymethyl)-N-phenyl-1,4-oxathian-3-imine

Conditions

Conditions	Yield
Stage #1: 2-ethynylfuran; Phenyl glycidyl ether With silver carbonate In 1,4-dioxane at 25℃; for 0.5h; Stage #2: phenyl isothiocyanate In 1,4-dioxane at 55℃; for 18h; regioselective reaction;	84%

...Expand

: 18649-64-4
2-ethynylfuran

: (1S,2R,3S,4R,5S)-4-(2-azido-6-(methylamino)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

: C20H21N9O4

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In water; tert-butyl alcohol at 20℃;	81%

: 18649-64-4
2-ethynylfuran

: 103-71-9
phenyl isocyanate

: 4-(furan-2-yl)-3-phenylthiazol-2(3H)-one

Conditions

Conditions	Yield
With N-methylcyclohexylamine; potassium tert-butylate; sulfur; copper(l) chloride In N,N-dimethyl-formamide at 55℃; for 16h; Molecular sieve; Inert atmosphere;	81%

: 18649-64-4
2-ethynylfuran

: 1192-62-7
1-(2-furyl)-1-ethanone

Conditions

Conditions	Yield
With Perfluorooctanesulfonic acid; C8AgF17O3S*H2O In water at 100℃; for 8h; Darkness; regioselective reaction;	80%
With silver tetrafluoroborate; water In acetic acid at 110℃; for 10h; regioselective reaction;	76%

: 18649-64-4
2-ethynylfuran

: (E)-2,2,2-trifluoro-N-(4-methoxyphenyl)acetimidoyl chloride

: 4-methoxy-N-[(2Z)-1,1,1-trifluoro-4-(furan-2-yl)but-3-yn-2-ylidene]aniline

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; potassium iodide In acetonitrile at 60℃; for 16h; Inert atmosphere;	79%

: 18649-64-4
2-ethynylfuran

: 67-68-5
dimethyl sulfoxide

: 95-68-1
2,4-Xylidine

: 4-furan-2-yl-6,8-dimethyl-quinoline

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver(I) triflimide at 120℃; for 8h; regioselective reaction;	79%

...Expand

: 18649-64-4
2-ethynylfuran

: 591-50-4
iodobenzene

: 35133-77-8
2-(2-phenylethynyl)furan

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide Ambient temperature;	78%

: 18649-64-4
2-ethynylfuran

: 118-48-9
isatoic anhydride

: 26059-84-7
2-(furan-2-yl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
With copper(l) iodide; ammonium acetate In neat (no solvent) at 120℃; for 4h;	77%

: 18649-64-4
2-ethynylfuran

: 15109-94-1
1-(2-furyl)-2-bromoethanone

Conditions

Conditions	Yield
With N,N'-ethylenethiourea; 1,3-dibromo-5,5-dimethylhydantoin; water In acetone at 45℃;	77%

: 18649-64-4
2-ethynylfuran

: 12082-03-0
tricarbonyl(η6-chlorobenzene)chromium

: 185459-42-1
tricarbonyl[η(6)-(2-furylethynyl)benzene]chromium(0)

Conditions

Conditions	Yield
With NEt3; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran (argon); addn. of the alkyne in THF to the Cr complex, NEt3 and the catalysts at room temp. over 1 h, reflux (4 h); addn. of Et2O, filtration, evapn., chromy. (basic alumina; Et2O/pentane), recrystn. (Et2O/pentane); elem. anal.;	76%

: 18649-64-4
2-ethynylfuran

: 17357-25-4
2,2‐dibromo‐1‐(furan‐2‐yl)ethan‐1‐one

Conditions

Conditions	Yield
With N,N'-ethylenethiourea; 1,3-dibromo-5,5-dimethylhydantoin; water at 20℃;	76%

: 18649-64-4
2-ethynylfuran

: 753-90-2
trifluoroethylamine

: 5-(furan-2-yl)-3-(trifluoromethyl)isoxazole

Conditions

Conditions	Yield
With copper(l) iodide; tert.-butylnitrite; acetic acid; zinc dibromide In chloroform at 20℃; for 24h; Schlenk technique; Inert atmosphere;	76%

: 584-12-3
2-bromofuran

: 18649-64-4
2-ethynylfuran

: 65406-81-7
1,2-di(furan-2-yl)ethyne

Conditions

Conditions	Yield
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide heteroarylation; Heating;	75%

: 18649-64-4
2-ethynylfuran

: 1655-07-8
ethyl 2-oxocyclohexane carboxylate

: ethyl (Z)-2-(2-furanyl)-4-oxo-1-cyclooctenecarboxylate

Conditions

Conditions	Yield
With (Re(CO)3(THF)Br)2 In toluene at 80℃; for 24h; Molecular sieve;	74%

: 18649-64-4
2-ethynylfuran

: 1188381-70-5
C10H10O2S2

: 1188381-83-0
2-(furan-2-yl)-4-methyl-5-(phenylsulfonylmethyl)thiophene

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride In toluene at 50℃; for 12h; Inert atmosphere;	73%

: 18649-64-4
2-ethynylfuran

: 75-15-0
carbon disulfide

: 122-60-1
Phenyl glycidyl ether

: 2-((furan-2-yl)methylene)-6-(phenoxymethyl)-1,4-oxathiane-3-thione

Conditions

Conditions	Yield
With copper diacetate; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine In water; tert-butyl alcohol at 0 - 23℃; for 8h;	73%

...Expand

: 18649-64-4
2-ethynylfuran

: 368-39-8
triethyloxonium fluoroborate

: 199620-14-9, 13007-92-6
chromium(0) hexacarbonyl

: pentacarbonyl[ethoxy(2-furylethynyl)carbene]chromium(0)

Conditions

Conditions	Yield
With n-BuLi In diethyl ether; hexane n-BuLi in hexane was added to soln. 2-ethynylfuran in Et2O at -78°C, 50 min at -78°C, warmed for 15 min, added at 0°C to Cr(CO)6 in Et2O, warmed to r.t., 1 h, THF was added, overnight, cooled to -78°C, Et3OBF4, 1 h at r.t.; soln. was concd., filtered, and evapd. in vacuo, residue was purified bychromy. on silica; elem. anal.;	72%

...Expand

2-Ethynylfuran Specification

The IUPAC name of this chemical is 2-Ethynylfuran. With the CAS registry number 18649-64-4, it is also named as Furan,2-ethynyl-. In addition, the molecular formula is C₆H₄O and the molecular weight is 92.10. It should be stored in a cool and dry place.

Physical properties about 2-Ethynylfuran are: (1)ACD/LogP: 1.56; (2)ACD/LogD (pH 5.5): 1.56; (3)ACD/LogD (pH 7.4): 1.56; (4)ACD/BCF (pH 5.5): 9.05; (5)ACD/BCF (pH 7.4): 9.05; (6)ACD/KOC (pH 5.5): 168.38; (7)ACD/KOC (pH 7.4): 168.38; (8)#H bond acceptors: 1; (9)Polar Surface Area: 13.14 Å²; (10)Index of Refraction: 1.5; (11)Molar Refractivity: 26.29 cm³; (12)Molar Volume: 89.3 cm³; (13)Polarizability: 10.42 ×10^-24cm³; (14)Surface Tension: 35.6 dyne/cm; (15)Density: 1.03 g/cm³; (16)Flash Point: 12.2 °C; (17)Enthalpy of Vaporization: 33.09 kJ/mol; (18)Boiling Point: 106.3 °C at 760 mmHg; (19)Vapour Pressure: 33.1 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: C#Cc1occc1
(2)InChI: InChI=1/C6H4O/c1-2-6-4-3-5-7-6/h1,3-5H
(3)InChIKey: CTVCBOZMKFQEAP-UHFFFAOYAB

Product Name

3-ETHYNYL-2-HYDROXY-PHENOL

Synthetic route

2-Ethynylfuran Specification

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