3'-Bromophenyl acetylene supplier

Name
1-BROMO-3-ETHYNYL-BENZENE
EINECS
CAS No. 766-81-4
Article Data27
CAS DataBase
Density 1.5 g/cm³
Solubility
Melting Point
Formula C₈H₅Br
Boiling Point 211.8 °C at 760 mmHg
Molecular Weight 181.032
Flash Point 85.7 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 3'-Bromophenylacetylene;1-Bromo-3-ethynylbenzene;Benzene, 1-bromo-3-ethynyl-;
PSA 0.00000
LogP 2.43040

Synthetic route

: 3989-13-7
2-(3-bromophenyl)ethynyltrimethylsilane

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
With methanol; potassium carbonate for 0.5h;	98%
With ethanol; caesium carbonate In dichloromethane at 20℃; for 4h; Inert atmosphere;	93.9%
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 2h;	92%

: 3132-99-8
m-bromobenzoic aldehyde

: 90965-06-3
dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 12h;	95%
With potassium carbonate In methanol at 20℃;	84%

: 1-bromo-3-(2',2'-dibromovinyl)benzene

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; water; triphenylphosphine In tetrahydrofuran at 80℃; for 2.5h; Corey-Fuchs Alkyne Synthesis; Sealed tube;	91%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25 - 30℃; for 16h;	83%
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere;
Stage #1: 1-bromo-3-(2',2'-dibromovinyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: With methanol In tetrahydrofuran for 1h;

: C9H7Br3O2

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h;	90%

: 2142-63-4
1-(3-Bromophenyl)ethanone

A: 766-81-4
3-bromophenylacetylene

B: 138857-35-9
1-Brom-3-(1-chlorethenyl)benzol

Conditions

Conditions	Yield
With pyridine; phosphorus pentachloride at 110℃; for 0.0583333h; microwave irradiation;	A 54% B 33 % Chromat.

: 2142-63-4
1-(3-Bromophenyl)ethanone

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
With phosphorus pentachloride; sodium ethanolate 1) 35 deg C, 15 min, 2) 3 h, 110 deg C; Yield given. Multistep reaction;

: 67-56-1
methanol

: 3989-13-7
2-(3-bromophenyl)ethynyltrimethylsilane

A: 766-81-4
3-bromophenylacetylene

B: 1-bromo-3-(2-methoxy-vinyl)benzene

Conditions

Conditions	Yield
With potassium carbonate at 120 - 130℃; for 0.25h; microwave irradiation;

...Expand

: 591-18-4
1-Bromo-3-iodobenzene

: 1066-54-2
trimethylsilylacetylene

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
Stage #1: 1-Bromo-3-iodobenzene; trimethylsilylacetylene With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; Stage #2: With methanol; water; potassium carbonate In tetrahydrofuran at 20℃;
With potassium carbonate In methanol; acetonitrile at 40℃; Sonogashira Cross-Coupling; chemoselective reaction;

: 591-18-4
1-Bromo-3-iodobenzene

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(PPh3)2Cl2; CuI; Et3N / 3 h / 20 °C 2: Pd(PPh3)2Cl2TBAF / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: sodium methylate; potassium carbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: palladium on copper / Inert atmosphere 2: potassium carbonate; methanol / Inert atmosphere View Scheme

: 14473-91-7
3-Bromocinnamic acid

: 766-81-4
3-bromophenylacetylene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 20 - 60 °C / Irradiation; Bromination 2: potassium carbonate / dimethyl sulfoxide / 12 h / 115 °C View Scheme

: 766-81-4
3-bromophenylacetylene

: 943341-66-0
2-(3-bromophenyl)ethenylboronic acid

Conditions

Conditions	Yield
With benzo[1,3,2]dioxaborole In tetrahydrofuran Heating;	100%

: 914942-88-4
tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate

: 766-81-4
3-bromophenylacetylene

: 914943-95-6
tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 75℃; for 0.5h;	100%

: 918483-35-9
4-iodo-1-(2,2,2-trifluoroethyl)-1H-pyrazole

: 766-81-4
3-bromophenylacetylene

: 918483-50-8
4-[(3-bromophenyl)ethynyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole

Conditions

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 20 - 80℃; for 1h;	99%

: 766-81-4
3-bromophenylacetylene

: 918487-97-5
4-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile

Conditions

Conditions	Yield
Stage #1: 4-iodopyrrole-2-carbonitrile With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide for 0.166667h; Stage #2: 3-bromophenylacetylene In N,N-dimethyl-formamide at 20℃;	99%

: 766-81-4
3-bromophenylacetylene

: 1-bromo-3-(iodoethynyl)benzene

Conditions

Conditions	Yield
With N-iodo-succinimide In acetone at 20℃; for 3h;	99%
With aluminum oxide; N-iodo-succinimide In acetonitrile at 80℃; for 1h; Molecular sieve;	99%
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;	98%
With N-chlorobenzenesulfonamide; potassium iodide In acetonitrile at 20℃; for 2h;	96%

: 356-42-3
2,2,3,3,3-pentafluoropropanoic anhydride

: 6926-44-9
phenethyl azide

: 766-81-4
3-bromophenylacetylene

: 6-(3-bromophenyl) - 3-(pentafluoroethyl)-4-phenylethyl-1,2,4-triazin-5(4H)-one

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran; hexane at 30℃; for 15h; Inert atmosphere;	99%
With copper(l) iodide; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran; hexane at 30℃; for 15h; Sealed tube; Glovebox; Inert atmosphere;	99%

...Expand

: 766-81-4
3-bromophenylacetylene

: 91-56-5
indole-2,3-dione

: (S)-3-((3-bromophenyl)ethynyl)-3-hydroxyindolin-2-one

Conditions

Conditions	Yield
With C36H29N2O2P; cobalt(II) diacetate tetrahydrate In ethanol at 30℃; for 20h; Schlenk technique; Glovebox; Inert atmosphere; enantioselective reaction;	99%

: 7648-30-8
ethyl 2,2-difluoro-2-iodoacetate

: 766-81-4
3-bromophenylacetylene

: ethyl 4-(3-bromophenyl)-2,2-difluoro-4-iodobut-3-enoate

Conditions

Conditions	Yield
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%

: 124-38-9
carbon dioxide

: 766-81-4
3-bromophenylacetylene

: 29835-28-7
3-(3-bromophenyl)propiolic acid

Conditions

Conditions	Yield
With {(N,N'-cyclohexane-1,2-diylbis((4-(tert-butyl)benzoyl)amide))Nd[N(SiMe3)2](tetrahydrofuran)}2; caesium carbonate In dimethyl sulfoxide at 40℃; under 760.051 Torr; for 24h; Schlenk technique;	97%
With C76H124N6Nd2O6Si4; caesium carbonate In dimethyl sulfoxide at 40℃; under 760.051 Torr; for 24h; Inert atmosphere;	97%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; under 750.075 Torr; for 12h;	82%
With sodium acetate; tetraoctyl ammonium bromide; copper(I) bromide In acetonitrile at 25℃; under 11251.1 Torr; for 16h; Inert atmosphere;	78%
With {[Cu4(μ3-OH)2(atrz)2(SIP)2]•4H2O}n; caesium carbonate In N,N-dimethyl-formamide at 100℃; under 2250.23 Torr; for 16h; Autoclave;	77%

: 766-81-4
3-bromophenylacetylene

: 7-fluoro-4H-thiochromen-4-one

: (S)-2-((3-bromophenyl)ethynyl)-7-fluorothiochroman-4-one

Conditions

Conditions	Yield
With copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; C36H20F10NO2P; N-ethyl-N,N-diisopropylamine In toluene at 0℃; for 1h; Inert atmosphere; enantioselective reaction;	97%

: 766-81-4
3-bromophenylacetylene

: 2114-36-5, 101308-38-7
1-bromopropylbenzene

: (R)-1-bromo-3-(3-phenylpent-1-yn-1-yl)benzene

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate; C55H70N3O2P; caesium carbonate In diethyl ether at 20℃; Sonogashira Cross-Coupling; Inert atmosphere; enantioselective reaction;	96%

: 766-81-4
3-bromophenylacetylene

: 163852-55-9
methyl 4-[(tert-butoxycarbonyl)amino]but-2-ynoate

: C18H20BrNO4

Conditions

Conditions	Yield
Stage #1: methyl-4,N(tert-butoxycarbonyl)amino,but-2-ynoate With palladium diacetate; tris(2,6-dimethoxyphenyl)phosphine In toluene at 20℃; for 0.166667h; Stage #2: 3-bromophenylacetylene In toluene at 20℃; for 6h;	95%

: 57744-67-9
6-iodo-1,4-benzodioxane

: 766-81-4
3-bromophenylacetylene

: 1035267-43-6
6-[(3-bromophenyl)ethynyl]-2,3-dihydro-1,4-benzodioxine

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 72h;	94%

: 766-81-4
3-bromophenylacetylene

: 1359973-18-4
3-cyclopentyl-2-iodo-3H-imidazo[4,5-b]pyridine

: 1397718-26-1
2-(2-(3-bromophenyl)ethynyl)-3-cyclopentyl-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Stage #1: 3-bromophenylacetylene; 3-cyclopentyl-2-iodo-3H-imidazo[4,5-b]pyridine With tetrabutylammonium acetate In 1-methyl-pyrrolidin-2-one at 20℃; for 0.15h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With (bis(tricyclohexyl)phosphine)palladium(II) dichloride In 1-methyl-pyrrolidin-2-one at 110℃; Sonogashira Cross-Coupling; Inert atmosphere; Microwave irradiation;	94%

: 766-81-4
3-bromophenylacetylene

: 1-bromo-3-(bromoethynyl)benzene

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetone at 20℃; for 3h;	94%
With N-chlorobenzenesulfonamide; sodium bromide In water; acetonitrile at 70℃; for 24h;	93%
With N-Bromosuccinimide; silver nitrate In acetone at 20℃;

: 455-13-0
4-Iodobenzotrifluoride

: 766-81-4
3-bromophenylacetylene

: 1-bromo-3-(2-(4-(trifluoromethyl)phenyl)ethynyl)benzene

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 12h; Inert atmosphere;	94%

: 766-81-4
3-bromophenylacetylene

: 622-79-7
benzyl azide

: 1-benzyl-4-(3-bromophenyl)-1H-1,2,3-triazole

Conditions

Conditions	Yield
With [(1-phenylisoquinoline)2Ir(acetylacetonate)] In dichloromethane at 20℃; Irradiation; regioselective reaction;	94%

: 766-81-4
3-bromophenylacetylene

: 918488-00-3
4-[(3-bromophenyl)ethynyl]-1H-pyrrole-2-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 4-iodo-1H-pyrrole-2-carbaldhehyde With triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 3-bromophenylacetylene With triethylamine; copper(l) iodide In N,N-dimethyl-formamide for 2h;	93%

: 593-60-2
Vinyl bromide

: 766-81-4
3-bromophenylacetylene

: 1369534-03-1
1-bromo-3-(but-3-en-1-ynyl)benzene

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	93%

: 766-81-4
3-bromophenylacetylene

: 2142-63-4
1-(3-Bromophenyl)ethanone

Conditions

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) In methanol; water at 110℃; for 6h; Schlenk technique; regioselective reaction;	93%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6h;	93%
With tropylium tetrafluoroborate; water; acetic acid at 130℃; for 48h; Inert atmosphere;	64%

: 60-35-5
acetamide

: 766-81-4
3-bromophenylacetylene

: 70933-58-3
N-(3-ethynylphenyl)acetamide

Conditions

Conditions	Yield
With potassium phosphate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; palladium diacetate In water; tert-butyl alcohol at 110℃; for 4.5h; Inert atmosphere;	93%

: 766-81-4
3-bromophenylacetylene

: 21575-13-3
4-amino-6,7-dimethoxyquinazoline

: N-(3-ethynylphenyl)-6,7-dimethoxyquinazolin-4-amine

Conditions

Conditions	Yield
With potassium phosphate; 1-butyl-3-methylimidazolium aminoethanic acid salt In N,N-dimethyl acetamide at 80℃; for 2h; Reagent/catalyst;	92.54%

: 766-81-4
3-bromophenylacetylene

: 128140-82-9
1-(difluoromethoxy)-4-iodobenzene

: 1065169-09-6
1-bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 4h; Product distribution / selectivity; Heating;	92%
With triethylamine; dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide for 4h; Product distribution / selectivity; Heating;	92%

: 766-81-4
3-bromophenylacetylene

: 120-92-3
cyclopentanone

: 1403824-61-2
1-((3-bromophenyl)ethynyl)cyclopentanol

Conditions

Conditions	Yield
Stage #1: 3-bromophenylacetylene With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: cyclopentanone In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	92%

: 766-81-4
3-bromophenylacetylene

: 1551103-06-0
C8H4BrCl

Conditions

Conditions	Yield
With N-chloro-succinimide; potassium carbonate; silver carbonate In propan-1-ol at 50℃; for 6h; Sealed tube; Inert atmosphere; Green chemistry;	92%

: 766-81-4
3-bromophenylacetylene

: 38622-91-2, 36635-61-7
[(p-methylphenyl)sulfonylmethyl]isonitrile

: (E)-1-(1-iodo-2-p-toluenesulfonylvinyl)-3-bromobenzene

Conditions

Conditions	Yield
With iodine In dimethyl sulfoxide at 20℃; for 0.333333h;	92%

: 766-81-4
3-bromophenylacetylene

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 1-(3-bromophenyl)-5-((tert-butyldiphenylsilyl)oxy)pent-1-yn-3-ol

Conditions

Conditions	Yield
Stage #1: 3-bromophenylacetylene With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 0.25h; Stage #2: 3-(tert-butyldiphenylsilyloxy)-1-propanal In tetrahydrofuran at -78 - 20℃; for 12h;	92%

: 32889-11-5
2-chloro-N-(quinolin-8-yl)acetamide

: 344-14-9
dimethyl 2-fluoromalonate

: 766-81-4
3-bromophenylacetylene

: (E)-dimethyl 2-(1-(3-bromophenyl)-4-oxo-4-(quinolin-8-ylamino)but-1-en-2-yl)-2-fluoromalonate

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In tetrahydrofuran at 80℃; for 1.5h; Inert atmosphere; stereoselective reaction;	92%

...Expand

3'-Bromophenyl acetylene Specification

The systematic name of 3'-Bromophenyl acetylene is 1-bromo-3-ethynylbenzene. With the CAS registry number 766-81-4, it is also named as Benzene, 1-bromo-3-ethynyl-. The product's category is Aromatic Halides (substituted). In addition, its molecular formula is C₈H₅Br and molecular weight is 181.03.

The other characteristics of 3'-Bromophenyl acetylene can be summarized as: (1)ACD/LogP: 3.17; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.17; (4)ACD/LogD (pH 7.4): 3.17; (5)ACD/BCF (pH 5.5): 151.53; (6)ACD/BCF (pH 7.4): 151.53; (7)ACD/KOC (pH 5.5): 1265.94; (8)ACD/KOC (pH 7.4): 1265.94; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.604; (13)Molar Refractivity: 41.53 cm³; (14)Molar Volume: 120.6 cm³; (15)Polarizability: 16.46×10^-24cm³; (16)Surface Tension: 46 dyne/cm; (17)Density: 1.5 g/cm³; (18)Flash Point: 85.7 °C; (19)Enthalpy of Vaporization: 42.98 kJ/mol; (20)Boiling Point: 211.8 °C at 760 mmHg; (21)Vapour Pressure: 0.261 mmHg at 25 °C.

Uses of 3'-Bromophenyl acetylene: it can be used to produce 1-bromo-3-(1-bromo-vinyl)-benzene.

This reaction needs NEt₄Br and CH₂Cl₂. The yield is 73 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: Brc1cc(C#C)ccc1
(2)InChI: InChI=1/C8H5Br/c1-2-7-4-3-5-8(9)6-7/h1,3-6H
(3)InChIKey: TZDXNFAAJNEYIO-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C8H5Br/c1-2-7-4-3-5-8(9)6-7/h1,3-6H
(5)Std. InChIKey: TZDXNFAAJNEYIO-UHFFFAOYSA-N

Product Name

1-BROMO-3-ETHYNYL-BENZENE

Synthetic route

3'-Bromophenyl acetylene Specification

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