3-Bromofuran supplier | CasNO.22037-28-1

Name
3-Bromofuran
EINECS 244-744-6
CAS No. 22037-28-1
Article Data8
CAS DataBase
Density 1.662 g/cm³
Solubility Soluble in chloroform, ethyl acetate. Insoluble in water.
Melting Point 131.5-132 °C
Formula C₄H₃BrO
Boiling Point 103 °C at 760 mmHg
Molecular Weight 146.971
Flash Point 3.3 °C
Transport Information UN 1993 3/PG 2
Appearance Colorless to light yellow liquid
Safety 16-23-24/25-37/39-26-33-29-7/9
Risk Codes 11-36/37/38
Molecular Structure
Hazard Symbols F, Xi
Synonyms Furan, 3-bromo-;
PSA 13.14000
LogP 2.04210

Synthetic route

: 32460-02-9
3,4-dibromofuran

: 22037-28-1
3-bromofurane

Conditions

Conditions	Yield
Stage #1: 3,4-dibromofuran With n-butyllithium In diethyl ether at -78℃; for 0.5h; Stage #2: With water In diethyl ether Further stages.;	55%
With water; tert.-butyl lithium; diisopropylamine 1.) Et2O, pentane, -78 deg C, 30 min, 2.) Et2O, pentane, from -78 deg C, 1 h to RT, 2 h; Yield given. Multistep reaction;

: (1R,2S,6R,7S)-8,9-Dibromo-4,10-dioxa-tricyclo[5.2.1.02,6]decane-3,5-dione

: 22037-28-1
3-bromofurane

Conditions

Conditions	Yield
With quinoline at 50 - 140℃; dehydrobromination/retro-Diels-Alder reaction;	34%

: 195619-38-6
(E)-2-bromo-2-butene-1,4-diol

: 22037-28-1
3-bromofurane

Conditions

Conditions	Yield
With sodium dichromate; sulfuric acid In water Heating;	10%

: 5458-08-2, 10035-20-8, 10035-21-9, 22155-05-1, 51371-59-6
trans-5,6-dibromo-7-oxabicyclo{2.2.1}heptane-2-exo,3-cis-dicarboxylic acid anhydride

: 22037-28-1
3-bromofurane

Conditions

Conditions	Yield
With potassium hydroxide

: 2-bromo-2-butene-1,4-diol

: 22037-28-1
3-bromofurane

Conditions

Conditions	Yield
With potassium dichromate; sulfuric acid In water; pentane Heating;

3-bromo-pyromucic acid: 3-bromo-pyromucic acid

: 22037-28-1
3-bromofurane

Conditions

Conditions	Yield
With calcium oxide

: 22037-28-1
3-bromofurane

: 155203-52-4
(5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one

: 259265-70-8
(4S,5R)-4,8-dimethyl-1-(3'-furyl)-5-hydroxy-6-nonen-1-one

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0666667h; Metallation; Stage #2: (5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 0.25h; Ring cleavage; alkylation;	98%

: 22037-28-1
3-bromofurane

: 55-21-0
benzamide

: 70150-83-3
N-(furan-3-yl)benzamide

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 110℃; for 24h;	98%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 24h;	98%

: 22037-28-1
3-bromofurane

: 271-63-6
7-Azaindole

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

Conditions

Conditions	Yield
Inert atmosphere;	98%

: 22037-28-1
3-bromofurane

: 161105-12-0
2-<(4aR,5R,6R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-1,5,6,8-tetramethyl-5-naphthyl>ethanal

: 3-<1-hydroxy-2-<(4aR,5R,6R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-1,5,6,8-tetramethyl-5-naphthyl>ethyl>furan

Conditions

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -70 deg C, 25 min;	97%

: 22037-28-1
3-bromofurane

: 4248-19-5
tert-butyl carbamate

: 56267-48-2
N-(3-furyl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 110℃; for 24h;	97%

: 22037-28-1
3-bromofurane

: 536-74-3
phenylacetylene

: 1043906-52-0
3-(phenylethynyl)furan

Conditions

Conditions	Yield
With Cu[9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene]I; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere;	96%
With pyrrolidine; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 120℃; for 7h; Heck alkynylation; Inert atmosphere;	100 %Chromat.

: 22037-28-1
3-bromofurane

: 4885-02-3
Dichloromethyl methyl ether

: 14757-78-9
3-bromofurfural

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 2.1h; Rieche Formylation;	96%

: 22037-28-1
3-bromofurane

: 434284-14-7
N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide

: 383159-58-8
1-(3-furyl)-2-[(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-trans-naphthyl]methylketone

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide In tetrahydrofuran; hexane at -78℃; for 1h;	95%

: 22037-28-1
3-bromofurane

: 111-88-6
Octanethiol

: 1114567-72-4
3-furyl octyl sulfide

Conditions

Conditions	Yield
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; caesium carbonate In 1,2-dimethoxyethane at 110℃; Inert atmosphere;	95%

: 22037-28-1
3-bromofurane

: 108-98-5
thiophenol

: 127459-19-2
3-furyl phenyl sulfide

Conditions

Conditions	Yield
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; lithium hexamethyldisilazane In 1,2-dimethoxyethane at 110℃; Inert atmosphere;	95%
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating;	75%

: 22037-28-1
3-bromofurane

: 1073-13-8
4,4-dimethylcyclohexenone

: 1263002-09-0
3-(4,4-dimethylcyclohexa-1,5-dienyl)furan

Conditions

Conditions	Yield
Stage #1: 4,4-dimethylcyclohexenone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 3-bromofurane In 1,4-dioxane at 110℃; Inert atmosphere;	95%

: 22037-28-1
3-bromofurane

: (1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalin-1-yl)-acetaldehyde

: 1-furan-3-yl-2-(1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalin-1-yl)-ethanol

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalin-1-yl)-acetaldehyde In tetrahydrofuran at -78℃; for 1.5h; Further stages.;	94%

: 22037-28-1
3-bromofurane

: 98-80-6
phenylboronic acid

: 13679-41-9
3-phenylfuran

Conditions

Conditions	Yield
With potassium phosphate; tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; palladium dichloride In o-xylene at 90℃; for 24h; Concentration; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	94%
With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; potassium carbonate In dichloromethane; toluene at 100℃; for 5h; Suzuki coupling; Reflux;	92%
With potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 90℃; for 20h; Suzuki coupling reaction;	91%

: 22037-28-1
3-bromofurane

: 100-58-3
phenylmagnesium bromide

: 13679-41-9
3-phenylfuran

Conditions

Conditions	Yield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Ambient temperature;	93%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 3.33333h; Inert atmosphere;	60%

: 22037-28-1
3-bromofurane

: 28987-79-3
m-tolylmagnesium bromide

: 80866-23-5
3-(3-methylphenyl)furan

Conditions

Conditions	Yield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Ambient temperature;	93%

: 22037-28-1
3-bromofurane

A: 110-00-9
furan

B: 6142-87-6
furan-3-d

Conditions

Conditions	Yield
With n-butyllithium; deuteromethanol In tetrahydrofuran; cyclohexane at -65℃;	A 6% B 93%

: 22037-28-1
3-bromofurane

: 470474-31-8
5-(2-bromo-ethyl)-1,1,4α-trimethyl-6-methylene-decahydro-naphthalene

: 61597-54-4
(+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: 5-(2-bromo-ethyl)-1,1,4α-trimethyl-6-methylene-decahydro-naphthalene In tetrahydrofuran; hexane at -78℃; for 2h; Further stages.;	93%
With n-butyllithium In tetrahydrofuran at -78℃;	93%

: 22037-28-1
3-bromofurane

: 1008-89-5
2-phenylpyridine

: 1042718-95-5
C19H13NO2

Conditions

Conditions	Yield
With potassium carbonate; triphenylphosphine; RuCl2(η6-C6H6) In 1-methyl-pyrrolidin-2-one at 120℃; for 20h;	93%

: 22037-28-1
3-bromofurane

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 1105713-64-1
C15H23NO5

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	93%

: 22037-28-1
3-bromofurane

: 76505-71-0
1,2-bis(2,2-diethoxyethyl) disulfide

: 594-19-4
tert.-butyl lithium

: 1173058-20-2
3-(2,2-diethoxy-ethylsulfanyl)furan

Conditions

Conditions	Yield
Stage #1: 3-bromofurane; tert.-butyl lithium In diethyl ether; pentane at -78℃; Inert atmosphere; Stage #2: 1,2-bis(2,2-diethoxyethyl) disulfide In diethyl ether; pentane at 20℃; Inert atmosphere;	93%

...Expand

: 22037-28-1
3-bromofurane

: 155203-52-4
(5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one

: 155203-53-5
(4R,5R)-4,8-dimethyl-1-(3'-furyl)-5-hydroxy-6-nonen-1-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	92.1%
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0666667h; Metallation; Stage #2: (5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 0.25h; Ring cleavage; alkylation;	92%

: 22037-28-1
3-bromofurane

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 14757-78-9
3-bromofurfural

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With lithium diisopropyl amide In 2-methyltetrahydrofuran at -45℃; for 0.5h; Vilsmeier-Haack reaction; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In 2-methyltetrahydrofuran at -40℃; for 0.333333h; Vilsmeier-Haack reaction; Inert atmosphere;	92%
With trichlorophosphate 1) room temperature, 1 h; 2) 80 deg C, 2 h;	86%
Stage #1: 3-bromofurane With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Stage #3: With phosphoric acid In tert-butyl methyl ether; water for 0.5h; Inert atmosphere; Cooling with ice; regioselective reaction;	84%

: 22037-28-1
3-bromofurane

: 3612-20-2
1-phenylmethyl-4-piperidone

: 1046478-47-0
1-benzyl-4-(furan-3-yl)-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
Stage #1: 1-phenylmethyl-4-piperidone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 3-bromofurane In 1,4-dioxane at 110℃; for 5h; Inert atmosphere;	92%

: 22037-28-1
3-bromofurane

: 882-33-7
diphenyldisulfane

: 127459-19-2
3-furyl phenyl sulfide

Conditions

Conditions	Yield
With tert.-butyl lithium In diethyl ether; pentane at 0 - 20℃; for 3.5h; Inert atmosphere;	91%
With n-butyllithium; diisopropylamine 1.) Et2O, hexane, -78 deg C, 30 min, 2.) Et2O, hexane, from -78 deg C, 1 h to RT, 2 h; Yield given. Multistep reaction;

: 22037-28-1
3-bromofurane

: 16(13->14)abeo-18a-homo-1,18-cyclo-ent-halima-5(10),14-dien-18-one

: 1,25-epoxy-4,9-cyclo-ent-isodysidiola-1,3(25),10,19-tetraen-4R-ol

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 16(13->14)abeo-18a-homo-1,18-cyclo-ent-halima-5(10),14-dien-18-one In tetrahydrofuran; hexane at -78℃; Further stages.;	91%

: 22037-28-1
3-bromofurane

: 292638-84-7
styrene

: 128587-62-2
3-styryl-furan

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 6H-dibenzo[d,f-1,3]diazepin-6-ylidene-5,7-dihydro-5,7-diphenylphosphanyl; sodium carbonate In N,N-dimethyl acetamide at 130℃; for 24h; Catalytic behavior; Heck Reaction; Schlenk technique; Inert atmosphere;	91%
With bis(η3-allyl-μ-chloropalladium(II)); 6H-dibenzo[d,f-1,3]diazepin-6-ylidene-5,7-dihydro-5,7-diphenylphosphanyl; sodium carbonate In N,N-dimethyl acetamide at 130℃; for 24h; Heck Reaction; Inert atmosphere; Schlenk technique;	91%
With NAP-Mg-Pd(0) In N,N-dimethyl-formamide at 130℃; for 8h; Reagent/catalyst; Solvent; Temperature; Heck Reaction;	83%
With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 140℃; for 20h; Heck reaction;	82%

: 22037-28-1
3-bromofurane

: 1692-25-7
3-pyridylboronic acid

: 55484-06-5
3-(furan-3-yl)-pyridine

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 110℃; for 20h; Suzuki Coupling; Inert atmosphere;	91%

: 22037-28-1
3-bromofurane

: 13139-86-1
4-methoxyphenyl magnesium bromide

: 20842-11-9
3-(4-methoxy-phenyl)-furan

Conditions

Conditions	Yield
With cobalt(II) chloride; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 20℃; for 1h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;	91%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 3.33333h; Inert atmosphere;	77%

: 22037-28-1
3-bromofurane

: 437703-37-2
methyl 2-ethylenedioxy-12-oxo-13,14,15,16-tetranor-ent-halim-5(10)-en-18-oate

: 437703-38-3
methyl 15,16-epoxy-2-ethylendioxy-12SR-hydroxy-5(10),13(16),14-ent-halimatrien-18-oate

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;	90%

: 22037-28-1
3-bromofurane

: 100-52-7
benzaldehyde

: 40358-49-4
α-phenyl-3-furanmethanol

Conditions

Conditions	Yield
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; Further stages.;	90%

3-Bromofuran Chemical Properties

Molecule structure of 3-Bromofuran (CAS NO.22037-28-1):

IUPAC Name: 3-Bromofuran
Molecular Weight: 146.97002 g/mol
Molecular Formula: C₄H₃BrO
Density: 1.662 g/cm³
Boiling Point: 103 °C at 760 mmHg
Flash Point: 3.3 °C
Index of Refraction: 1.505
Molar Refractivity: 26.24 cm³
Molar Volume: 88.4 cm³
Polarizability: 10.4×10^-24 cm³
Surface Tension: 32.9 dyne/cm
Enthalpy of Vaporization: 32.79 kJ/mol
Vapour Pressure: 38 mmHg at 25 °C
Storage Temp.: −20 °C
XLogP3: 2.2
H-Bond Acceptor: 1
Exact Mass: 145.936727
MonoIsotopic Mass: 145.936727
Topological Polar Surface Area: 13.1
Heavy Atom Count: 6
Complexity: 46.8
Canonical SMILES: C1=COC=C1Br
InChI: InChI=1S/C4H3BrO/c5-4-1-2-6-3-4/h1-3H
InChIKey: LXWLEQZDXOQZGW-UHFFFAOYSA-N
EINECS: 244-744-6
Product Categories of 3-Bromofuran (CAS NO.22037-28-1): HALIDE; Furans, Benzofurans & Dihydrobenzofurans; Halides; Furan&Benzofuran; Heterocyclic Compounds; Furans; Furans, Benzofurans & Dihydrobenzofurans; Heterocycles; Building Blocks; FuransHeterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks

3-Bromofuran Safety Profile

Hazard Codes: F, Irritant Xi
Risk Statements: 11-36/37/38
R11:Highly flammable.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-23-24/25-37/39-26-33-29-7/9
S16:Keep away from sources of ignition.
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S33:Take precautionary measures against static discharges.
S29:Do not empty into drains.
S7:Keep container tightly closed.
S9:Keep container in a well-ventilated place.
RIDADR: UN 1993 3/PG 2
WGK Germany: 3
F: 10
Hazard Note: Highly Flammable/Irritant
HazardClass: 3
PackingGroup: II

3-Bromofuran Specification

3-Bromofuran (CAS NO.22037-28-1) is also named as furan, 3-bromo- . It is colorless to light yellow liquid.

Product Name

3-Bromofuran

Synthetic route

3-Bromofuran Chemical Properties

3-Bromofuran Safety Profile

3-Bromofuran Specification

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