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% |
m-bromobenzoic aldehyde
dimethyl 1-(1-diazo-2-oxopropyl)phosphonate
3-bromophenylacetylene
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 12h; | 95% |
With potassium carbonate In methanol at 20℃; | 84% |
3-bromophenylacetylene
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; |
3-bromophenylacetylene
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h; | 90% |
1-(3-Bromophenyl)ethanone
A
3-bromophenylacetylene
B
1-Brom-3-(1-chlorethenyl)benzol
Conditions | Yield |
---|---|
With pyridine; phosphorus pentachloride at 110℃; for 0.0583333h; microwave irradiation; | A 54% B 33 % Chromat. |
Conditions | Yield |
---|---|
With phosphorus pentachloride; sodium ethanolate 1) 35 deg C, 15 min, 2) 3 h, 110 deg C; Yield given. Multistep reaction; |
methanol
2-(3-bromophenyl)ethynyltrimethylsilane
A
3-bromophenylacetylene
Conditions | Yield |
---|---|
With potassium carbonate at 120 - 130℃; for 0.25h; microwave irradiation; |
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; |
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 |
3-Bromocinnamic acid
3-bromophenylacetylene
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 |
3-bromophenylacetylene
2-(3-bromophenyl)ethenylboronic acid
Conditions | Yield |
---|---|
With benzo[1,3,2]dioxaborole In tetrahydrofuran Heating; | 100% |
tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate
3-bromophenylacetylene
tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 75℃; for 0.5h; | 100% |
4-iodo-1-(2,2,2-trifluoroethyl)-1H-pyrazole
3-bromophenylacetylene
4-[(3-bromophenyl)ethynyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole
Conditions | Yield |
---|---|
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 20 - 80℃; for 1h; | 99% |
3-bromophenylacetylene
4-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile
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% |
3-bromophenylacetylene
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% |
2,2,3,3,3-pentafluoropropanoic anhydride
phenethyl azide
3-bromophenylacetylene
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% |
Conditions | Yield |
---|---|
With C36H29N2O2P; cobalt(II) diacetate tetrahydrate In ethanol at 30℃; for 20h; Schlenk technique; Glovebox; Inert atmosphere; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere; stereoselective reaction; | 99% |
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% |
3-bromophenylacetylene
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% |
3-bromophenylacetylene
1-bromopropylbenzene
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate; C55H70N3O2P; caesium carbonate In diethyl ether at 20℃; Sonogashira Cross-Coupling; Inert atmosphere; enantioselective reaction; | 96% |
3-bromophenylacetylene
methyl 4-[(tert-butoxycarbonyl)amino]but-2-ynoate
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% |
6-iodo-1,4-benzodioxane
3-bromophenylacetylene
6-[(3-bromophenyl)ethynyl]-2,3-dihydro-1,4-benzodioxine
Conditions | Yield |
---|---|
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 72h; | 94% |
3-bromophenylacetylene
3-cyclopentyl-2-iodo-3H-imidazo[4,5-b]pyridine
2-(2-(3-bromophenyl)ethynyl)-3-cyclopentyl-3H-imidazo[4,5-b]pyridine
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% |
3-bromophenylacetylene
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℃; |
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 12h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With [(1-phenylisoquinoline)2Ir(acetylacetonate)] In dichloromethane at 20℃; Irradiation; regioselective reaction; | 94% |
3-bromophenylacetylene
4-[(3-bromophenyl)ethynyl]-1H-pyrrole-2-carbaldehyde
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% |
Vinyl bromide
3-bromophenylacetylene
1-bromo-3-(but-3-en-1-ynyl)benzene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 93% |
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% |
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% |
3-bromophenylacetylene
4-amino-6,7-dimethoxyquinazoline
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% |
3-bromophenylacetylene
1-(difluoromethoxy)-4-iodobenzene
1-bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene
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% |
3-bromophenylacetylene
cyclopentanone
1-((3-bromophenyl)ethynyl)cyclopentanol
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% |
3-bromophenylacetylene
C8H4BrCl
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% |
3-bromophenylacetylene
[(p-methylphenyl)sulfonylmethyl]isonitrile
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide at 20℃; for 0.333333h; | 92% |
3-bromophenylacetylene
3-(tert-butyldiphenylsilyloxy)-1-propanal
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% |
2-chloro-N-(quinolin-8-yl)acetamide
dimethyl 2-fluoromalonate
3-bromophenylacetylene
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In tetrahydrofuran at 80℃; for 1.5h; Inert atmosphere; stereoselective reaction; | 92% |
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
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