Conditions | Yield |
---|---|
With samarium In methanol at 45℃; for 6h; | 97% |
With triethylamine; phosphonic acid diethyl ester for 4h; Ambient temperature; | 96% |
With indium; ammonium chloride In ethanol; water for 16h; Heating; | 95% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; tetrabutylammomium bromide at 100℃; for 0.666667h; Hunsdiecker reaction; | 96% |
Conditions | Yield |
---|---|
With acetic acid; zinc In dichloromethane for 0.3h; Heating; E/Z ratio 55:45; | 95% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide In dichloromethane at 20℃; for 4h; | 95% |
With N-Bromosuccinimide; manganese (II) acetate tetrahydrate In water; acetonitrile at 20℃; | 92% |
With N,N-dimethyl-formamide; potassium bromide; trichlorophosphate In acetonitrile at 20℃; Reagent/catalyst; Sonication; | 75% |
(α,β-dibromohydrocinnamoyloxy)trimethylstannane
A
bromostyrene
Conditions | Yield |
---|---|
at 180℃; | A 85% B n/a |
Conditions | Yield |
---|---|
With potassium hydrogensulfate; hydroquinone In water at 150 - 185℃; | 84% |
Bromoform
benzaldehyde
A
bromostyrene
B
α,α-(dibromomethyl)phenylmethanol
Conditions | Yield |
---|---|
With 1,2-dimethoxyethane; titanium tetrachloride; magnesium In 1,2-dichloro-ethane at 0℃; for 3h; | A n/a B 80% |
Conditions | Yield |
---|---|
Stage #1: Cinnamic acid With triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: N-Bromosuccinimide In dichloromethane for 1h; | 73% |
2,2,2-tribromoethylbenzene
bromostyrene
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; chromium(III) bromide; iron In tetrahydrofuran at 4℃; for 16h; | 64% |
With sodium isopropanethiolate In methanol Heating; | 47% |
Conditions | Yield |
---|---|
With sodium hypochlorite; bromine In water; acetonitrile at 20℃; for 8h; | A 47% B 18% |
erythro-2,3-dibromo-3-phenylpropanol
A
bromostyrene
B
3-bromo-3-phenyl-2-propenol
(+/-)-threo-2-[bromo(phenyl)methyl]-oxirane
Conditions | Yield |
---|---|
With sodium hydroxide In benzene for 5h; Product distribution; Heating; var. reaction conditions, with and without use of phase transfer reagents; | A 13% B 20% C 22% |
Conditions | Yield |
---|---|
With sodium hydroxide lower-melting form; |
ethanol
erythro-2,3-dibromo-3-phenylpropanoic acid
potassium acetate
bromostyrene
Conditions | Yield |
---|---|
With water | |
With aqueous alkali | |
With ethanol; potassium acetate |
Conditions | Yield |
---|---|
With zinc |
2,3-dibromo-3-phenylpropanoic acid
N,N-dimethyl-aniline
benzene
A
styrene
B
bromostyrene
C
Cinnamic acid
2-bromo-1,4,11,12-tetrachloro-3-phenyl-1,2,3,4-tetrahydro-1,4-etheno-phenazine
A
bromostyrene
B
1,2,3,4-tetrachloro-phenazine
2,2,2-tribromo-1,3,2-benzodioxaphosphole
phenylacetaldehyde
A
1,1-dibromo-2-phenylethane
B
bromostyrene
Conditions | Yield |
---|---|
In dichloromethane for 2h; Ambient temperature; Yield given. Yields of byproduct given; |
(bromomethylene)triphenylphosphorane
benzaldehyde
A
bromostyrene
B
phenylacetylene
Conditions | Yield |
---|---|
THF; Yield given. Multistep reaction; |
1,1-dibromo-2-phenyl-2-(trimethylsiloxy)ethane
A
bromostyrene
B
(2-Bromo-1-phenyl-ethoxy)-trimethyl-silane
C
(E)/(Z)-β-Trimethylsiloxystyrene
Conditions | Yield |
---|---|
With hydrogenchloride; sec.-butyllithium 1.) THF, ether, pentane, -130 deg C, 4 h; 2.) CH3OH; Yield given. Multistep reaction. Yields of byproduct given; |
1,1-dibromo-2-phenyl-2-(trimethylsiloxy)ethane
A
bromostyrene
B
(E)/(Z)-β-Trimethylsiloxystyrene
Conditions | Yield |
---|---|
With hydrogenchloride; sec.-butyllithium 1.) THF, ether, pentane, -115 deg C, 4 h; 2.) CH3OH; Yield given. Multistep reaction. Yields of byproduct given; |
styrene
dimethyl sulfoxide
A
(+/-)-4-phenyl-[1,3]-dioxolane
B
phenylglyoxal hydrate
C
bromostyrene
D
2-Bromo-1-phenylethanol
E
acetophenone
F
(1,2-dibromoethyl)benzene
Conditions | Yield |
---|---|
With bromine Product distribution; Mechanism; 1) 15 deg C, 20 min; 2) rt, 1 h; 3) 80 deg C, 21 h; further reagent: HBr; | A n/a B 32 % Spectr. C n/a D n/a E n/a F n/a G n/a |
Conditions | Yield |
---|---|
Einwirkung auf zimtsaures Alkali; |
bromostyrene
Conditions | Yield |
---|---|
With sodium carbonate |
bromostyrene
Conditions | Yield |
---|---|
With water; bromine |
bromostyrene
Conditions | Yield |
---|---|
With sunlight lower-melting form; |
bromostyrene
Conditions | Yield |
---|---|
With sunlight higher-melting form; |
A
styrene
B
bromostyrene
Conditions | Yield |
---|---|
With ethanol; zinc |
(E)-3-phenylacrylic acid
water
A
bromostyrene
B
2-bromo-3-hydroxy-3-phenyl-propanoic acid
C
2-bromo-3-chloro-3-phenyl-propionic acid
Conditions | Yield |
---|---|
at 48℃; |
Conditions | Yield |
---|---|
With potassium tert-butylate | 100% |
With sodium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 1h; | 92% |
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 50℃; for 0.166667h; Schlenk technique; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; water In acetonitrile at 20℃; | 100% |
bromostyrene
1,3-bis(2,6-difluorophenyl)triazene
Conditions | Yield |
---|---|
With potassium hexafluorophosphate; tert-butylhypochlorite In dichloromethane at -78 - 20℃; Darkness; | 100% |
bromostyrene
4-methyl-N-(2-propenyl)benzenesulfonamide
(E)-N-allyl-N-styryl-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In tetrahydrofuran Schlenk technique; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Sonogashira Cross-Coupling; Inert atmosphere; Green chemistry; | 99% |
With iodo(4,5-bis(diphenylphosphano)-9,9-dimethylxanthene)copper(I); caesium carbonate In 1,4-dioxane at 135℃; for 24h; Inert atmosphere; | 98% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 25℃; for 12h; | 82% |
bromostyrene
(E)-3-((E)-1,3-diphenylallylidene)-5,5-dimethyl-1,2-oxaborolan-2-ol
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In 1,4-dioxane; water at 50℃; for 3h; Suzuki-Miyaura Coupling; | 99% |
Conditions | Yield |
---|---|
With N,N′-Bis(2-pyridylmethylidene)-1,2-trans-(R,R + S,S)-cyclohexanediamine; hydrogen; iron(II) chloride In tetrahydrofuran at -20 - 20℃; under 37503.8 Torr; for 18h; | 99% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 3h; regioselective reaction; | 99% |
bromostyrene
N-(diphenylmethylene)-1-(4-methoxyphenyl)methanamine
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 3h; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 6h; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 1.5h; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 1.5h; regioselective reaction; | 99% |
bromostyrene
1-(azidomethyl)-4-methoxybenzene
1-(4-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With piperidine; copper(II) oxide at 110℃; for 12h; | 99% |
bromostyrene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With N,N-diethylaniline; tetrakis(triethylphosphite)nickel(0) In N,N-dimethyl-formamide at 70℃; for 23h; | 98% |
at 140 - 160℃; Yield given; | |
With sodium hydroxide; trans-bromo(phenyl)bis(triphenylphosphine)palladium(II); cetyltributylphosphonium bromide; triphenylphosphine In toluene at 80℃; for 9h; | 80 % Chromat. |
Conditions | Yield |
---|---|
With sodium bromite; tributyltin chloride In dichloromethane; water Ambient temperature; | 98% |
3-(trifluoromethyl)pyrazole
bromostyrene
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In acetonitrile at 50℃; for 30h; | 98% |
Conditions | Yield |
---|---|
With iodo(4,5-bis(diphenylphosphano)-9,9-dimethylxanthene)copper(I); caesium carbonate In 1,4-dioxane at 135℃; for 24h; Inert atmosphere; | 98% |
With CuI(xantphos); caesium carbonate In N,N-dimethyl-formamide at 135℃; for 1h; Sonogashira type reaction; Inert atmosphere; Microwave irradiation; | 36% |
bromostyrene
4-methoxyphenylacetylen
(E)-1-methoxy-4-(4-phenylbutyl-3-en-1-yn-1-yl)benzene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine In water; dimethyl sulfoxide at 100℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere; | 98% |
bromostyrene
(E)-trimethyl(3-phenylallyl)silane
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 0.5h; Reagent/catalyst; Solvent; Time; Concentration; regioselective reaction; | 98% |
bromostyrene
sodium 4-methylbenzenesulfinate
1-methyl-4-[(E)-2-phenylethenesulfonyl]benzene
Conditions | Yield |
---|---|
With (1,2-dimethoxyethane)dichloronickel(II); C48H56IrN4(1+)*F6P(1-); 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With piperidine; copper(II) oxide at 110℃; for 12h; | 98% |
Conditions | Yield |
---|---|
With gallium(III) trichloride; 2,4-lutidine In 2-methyltetrahydrofuran; isopropyl alcohol at 85℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; | 97.6% |
Conditions | Yield |
---|---|
With triisopropanolamine; copper acetylacetonate; palladium(II) trifluoroacetate; 1-(2-ethoxyethyl)-3-methylimidazolium trifluoromethanesulfonimidide In N,N-dimethyl-formamide at 60℃; for 10h; Reagent/catalyst; Solvent; | 97.5% |
Conditions | Yield |
---|---|
With triisopropanolamine; copper acetylacetonate; palladium(II) trifluoroacetate; 1-(2-ethoxyethyl)-3-methylimidazolium trifluoromethanesulfonimidide In N,N-dimethyl-formamide at 80℃; for 6h; Reagent/catalyst; Solvent; | 97.4% |
Conditions | Yield |
---|---|
With triisopropanolamine; copper acetylacetonate; palladium(II) trifluoroacetate; 1-(2-ethoxyethyl)-3-methylimidazolium trifluoromethanesulfonimidide In N,N-dimethyl-formamide at 70℃; for 8h; Reagent/catalyst; Solvent; | 97.3% |
Conditions | Yield |
---|---|
Stage #1: oct-1-ene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 20℃; for 17h; Stage #2: bromostyrene With potassium phosphate; 2H(1+)*Cl4Pd(2-)*2H3N; poly[N-isopropylacrylamide-co-diphenyl(4'-styryl)phosphine] In tetrahydrofuran; 1,4-dioxane at 100℃; for 1.5h; Suzuki-Miyaura reaction; | 97% |
Conditions | Yield |
---|---|
Stage #1: bromostyrene With tert.-butyl lithium In diethyl ether; pentane at 25℃; for 0.5h; Stage #2: With indium(III) chloride In diethyl ether; pentane at 25℃; for 0.5h; Stage #3: ethyl iodoacetae With triethyl borane In diethyl ether; hexane; pentane at 25℃; for 14h; | 97% |
Stage #1: bromostyrene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 1h; Stage #2: With indium(III) chloride In tetrahydrofuran; diethyl ether; pentane at -78℃; for 1h; Stage #3: ethyl iodoacetae In tetrahydrofuran; diethyl ether; pentane at 20℃; Irradiation; Further stages.; | 83% |
Reported in EPA TSCA Inventory.
The β-Bromostyrene is an organic compound with the formula C8H7Br. The IUPAC name of this chemical is 2-bromoethenylbenzene. With the CAS registry number 103-64-0, it is also named as 1-Bromo-2-phenylethene. The product's category is Pharmaceutical Intermediates. Besides, it is clear yellowish to brown liquid, which should be stored in a cool and ventilated place. It is used as a fragrance intermediates.
Physical properties about β-Bromostyrene are: (1)ACD/LogP: 2.99; (2)ACD/LogD (pH 5.5): 2.99; (3)ACD/LogD (pH 7.4): 2.99; (4)ACD/BCF (pH 5.5): 110.05; (5)ACD/BCF (pH 7.4): 110.05; (6)ACD/KOC (pH 5.5): 1006.87; (7)ACD/KOC (pH 7.4): 1006.87; (8)#Freely Rotating Bonds: 1; (9)Index of Refraction: 1.63; (10)Molar Refractivity: 45.24 cm3; (11)Molar Volume: 127 cm3; (12)Polarizability: 17.93×10-24cm3; (13)Surface Tension: 41.5 dyne/cm; (14)Density: 1.44 g/cm3; (15)Flash Point: 101.7 °C; (16)Enthalpy of Vaporization: 43.87 kJ/mol; (17)Boiling Point: 220.9 °C at 760 mmHg; (18)Vapour Pressure: 0.164 mmHg at 25°C.
Preparation: this chemical can be prepared by β,β-dibromo-styrene. This reaction will need reagent HP(O)(OEt)2, Et3N. The reaction time is 4 hours at ambient temperature. The yield is about 96%.
Uses of β-Bromostyrene: it can be used to produce styrylsulfanyl-benzene at temperature of 135 °C. It will need reagent 1-methyl-2-pyrrolidone with reaction time of 2 hours. The yield is about 95%.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. When you are using it, wear suitable protective clothing and gloves, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: BrC=Cc1ccccc1
(2)InChI: InChI=1/C8H7Br/c9-7-6-8-4-2-1-3-5-8/h1-7H
(3)InChIKey: YMOONIIMQBGTDU-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C8H7Br/c9-7-6-8-4-2-1-3-5-8/h1-7H
(5)Std. InChIKey: YMOONIIMQBGTDU-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 1250mg/kg (1250mg/kg) | Food and Cosmetics Toxicology. Vol. 11, Pg. 1043, 1973. |
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