Conditions | Yield |
---|---|
With hydrogen bromide; oxygen at 20 - 23℃; under 1551.49 - 1603.2 Torr; for 4.5h; | A 97.8% B 1.57% |
Conditions | Yield |
---|---|
With 2AlBr3*CBr4; bromine at -20℃; for 3h; | 96% |
With antimony pentafluoride; 1,2-dibromomethane 1.) -78 deg C, 2 h, 2.) RT, 24 h; | 64% |
With 2AlBr3*CBr4; bromine In various solvent(s) at -20℃; for 3h; | 48 % Turnov. |
Conditions | Yield |
---|---|
With carbon tetrabromide; sodium bromide In N,N-dimethyl-formamide for 3h; Catalytic behavior; Irradiation; | 93% |
With tetralin; bromine ueber mehrere Stufen; | |
With sulfuric acid; potassium bromide |
triisopropyl phosphite
para-bromoacetophenone
A
diisopropyl [4-(acetyl)phenyl]phosphonate
B
isopropyl bromide
Conditions | Yield |
---|---|
With nickel dichloride at 180 - 190℃; for 0.0833333h; | A 91% B n/a |
di-isopropyl ether
carbon monoxide
4-Methylbenzyl bromide
A
isopropyl 2-p-tolylacetate
B
isopropyl bromide
Conditions | Yield |
---|---|
1,5-hexadienerhodium(I)-chloride dimer; potassium iodide at 75 - 90℃; under 735.5 Torr; overnight or in n-heptane; | A 78% B n/a |
{(η5-C5Me5)Os(CO)(PMe2Ph)i-Pr}
bromine
A
{(η5-C5Me5)Os(CO)(PMe2Ph)Br}
B
propene
C
isopropyl bromide
Conditions | Yield |
---|---|
In dichloromethane-d2 (N2); electrophilic cleavage reaction by addn. of bromine to a soln. of Cp*Os(CO)(PMe2Ph)i-Pr in CD2Cl2;; not isolated, detected by NMR;; | A 77% B 9% C 50% |
{(η5-C5Me5)Os(CO)2i-Pr}
A
{(η5-C5Me5)Os(CO)2Br}
B
isopropylmercury (1+); bromide
C
isopropyl bromide
Conditions | Yield |
---|---|
In dichloromethane-d2 (N2); electrophilic cleavage reaction by addn. of HgBr2 to a soln. of Cp*Os(CO)2i-Pr in CD2Cl2;; not isolated, detected by NMR;; | A 77% B 61% C 11% |
triisopropyl phosphite
1-(3-Bromophenyl)ethanone
A
(3-Acetyl-phenyl)-phosphonic acid diisopropyl ester
B
isopropyl bromide
Conditions | Yield |
---|---|
With nickel dichloride at 180 - 190℃; for 0.0833333h; | A 76% B n/a |
{(η5-C5Me5)Os(CO)2i-Pr}
bromine
A
{(η5-C5Me5)Os(CO)2Br}
B
propene
C
isopropyl bromide
Conditions | Yield |
---|---|
In dichloromethane-d2 (N2); electrophilic cleavage reaction by addn. of bromine to a soln. of Cp*Os(CO)2i-Pr in CD2Cl2;; not isolated, detected by NMR;; | A 75% B 6% C 39% |
2-isopropyl-2-boraadamantane
A
2-bromo-2-boraadamantane
D
hydrogen bromide
E
isopropyl bromide
Conditions | Yield |
---|---|
With ethanol; bromine In dichloromethane Irradiation (UV/VIS); under Ar, to soln. of educt in CH2Cl2 added soln. of Br2 in CH2Cl2 in portions during 1 h at -10°C under pressure of 170-200 mmHg with irrdn. with 200 W bulb, stirred for 30 min at -10°C, heated under vac. to 17°C; concd. in vac., cooled to -70°C, ethanol added, evapd. in vac. without heating; GLC anal. of products after oxidative hydrolysis; | A n/a B n/a C n/a D 73% E 4% |
With ethanol; bromine In dichloromethane under Ar in the dark, to soln. of educt in CH2Cl2 added soln. of Br2 inCH2Cl2 in portions during 5.5 h at -10°C under pressure of 170-200 mmHg, stirred for 30 min at -10°C, heated under vac. to 17°C; concd. in vac., cooled to -70°C, ethanol added, evapd. in vac. without heating; GLC anal. of products after oxidative hydrolysis; | A n/a B n/a C n/a D 14% E 65% |
With ethanol; bromine In dichloromethane under Ar, to soln. of educt in CH2Cl2 added soln. of Br2 in CH2Cl2 in portions during 2.5 h at -10°C under pressure of 170-200 mmHg, stirred for 30 min at -10°C, heated under vac. to 17°C; concd. in vac., cooled to -70°C, ethanol added, evapd. in vac. without heating; GLC anal. of products after oxidative hydrolysis; | A n/a B n/a C n/a D 23% E 38% |
triisopropyl phosphite
1,3-chlorobromopropane
A
O,O-diisopropyl (3-chloropropyl)phosphonate
B
isopropyl bromide
Conditions | Yield |
---|---|
at 135 - 140℃; for 3h; Arbuzov rearrangement; | A 28% B 68% |
1-bromo-4-methoxy-benzene
triisopropyl phosphite
A
diisopropyl (4-methoxyphenyl)phosphonate
B
isopropyl bromide
Conditions | Yield |
---|---|
With nickel dichloride at 185 - 195℃; for 0.0833333h; | A 67% B n/a |
bromobenzene
triisopropyl phosphite
A
diisopropyl phenylphosphonate
B
isopropyl bromide
Conditions | Yield |
---|---|
With nickel dichloride at 185 - 195℃; for 0.0833333h; | A 65.5% B n/a |
diethyl phenylphosphonite
1,3-chlorobromopropane
A
isopropyl bromide
B
ethyl (3-chloropropyl)phenylphosphinate
Conditions | Yield |
---|---|
at 135 - 140℃; for 3h; Arbuzov rearrangement; | A n/a B 62% |
triisopropyl phosphite
2-bromoanisole
A
(2-Methoxy-phenyl)-phosphonic acid diisopropyl ester
B
isopropyl bromide
Conditions | Yield |
---|---|
With nickel dichloride at 190 - 200℃; for 0.0833333h; | A 61% B n/a |
nickel dichloride at 190 - 200℃; |
triisopropyl phosphite
4-bromo-benzaldehyde
A
4-(diisopropoxyphosphoryl)benzaldehyde
B
isopropyl bromide
Conditions | Yield |
---|---|
With nickel dichloride at 170 - 180℃; for 0.0833333h; | A 54% B n/a |
Conditions | Yield |
---|---|
at 250 - 270℃; Equilibrium constant; | |
at 250 - 270℃; Equilibrium constant; die Umlagerung wird durch Sauerstoff, HBr, HgBr2, Tetraaethylammoniumbromid und Dibutylamin beschleunigt; | |
lagert sich im UV-Licht teilweise um; |
Conditions | Yield |
---|---|
With bromine | |
With hydrogen bromide | |
With pyridine; tributyltin bromide at 125℃; Thermodynamic data; Equilibrium constant; Δ G; | 49 % Chromat. |
propene
isopropyl bromide
Conditions | Yield |
---|---|
With hydrogen bromide bei Ausschluss von Luft und Zusatz von Oxydationsverzoegern wie Diphenylamin oder Thiokresol; | |
With tetrachloromethane; hydrogen bromide | |
With hydrogen bromide; iron(III) chloride im Dunkeln; |
Conditions | Yield |
---|---|
With hydrogen iodide at 150℃; |
propane
A
1,2-Dibromopropane
B
propyl bromide
C
1,3-dibromo-propane
D
isopropyl bromide
Conditions | Yield |
---|---|
at 300 - 330℃; Bromierung; weitere Produkte: 2.2-Dibrom-propan, Tribrompropan und Tetrabrompropan; |
Conditions | Yield |
---|---|
With bromine at 300 - 330℃; | |
With Bromoform; 1,2-dibromomethane In nitrogen at 525℃; for 0.0166667h; |
bromo-triphenyl-methane
isopropyl-diphenyl-phosphine oxide
B
isopropyl bromide
Conditions | Yield |
---|---|
at 100 - 200℃; |
bromo-triphenyl-methane
isopropyl diphenylphosphinite
B
isopropyl bromide
Conditions | Yield |
---|---|
at 100 - 200℃; |
Conditions | Yield |
---|---|
With bromine |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In acetone at 50℃; Kinetics; other reaction partners, other solvents, other temperatures; |
Conditions | Yield |
---|---|
With bromine at 24.9℃; Kinetics; other temperatures; |
propene
A
2-bromo-2-methylpentane
B
propyl bromide
C
isopropyl bromide
Conditions | Yield |
---|---|
With hydrogen bromide at -78℃; for 96h; Product distribution; | A 34 % Chromat. B 0.5 % Chromat. C 45 % Chromat. |
With hydrogen bromide at -78℃; for 96h; | A 34 % Chromat. B 0.5 % Chromat. C 45 % Chromat. |
Conditions | Yield |
---|---|
With tributyltin bromide In pyridine at 50℃; Thermodynamic data; Equilibrium constant; other temperatures, Δ G; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; | 90% |
In acetone | 88% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 55℃; for 11h; Inert atmosphere; | 100% |
4-Bromophenylacetonitrile
isopropyl bromide
2-(4-bromophenyl)-3-methylbutanenitrile
Conditions | Yield |
---|---|
Stage #1: 4-Bromophenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: isopropyl bromide In N,N-dimethyl-formamide; mineral oil for 16h; Inert atmosphere; Heating; | 100% |
Stage #1: 4-Bromophenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.25h; Stage #2: isopropyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; | |
Stage #1: 4-Bromophenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: isopropyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; | 21.3 g |
Stage #1: 4-Bromophenylacetonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: isopropyl bromide In tetrahydrofuran for 16h; Inert atmosphere; | |
With sodium hydride |
Conditions | Yield |
---|---|
100% | |
With potassium carbonate In N,N-dimethyl-formamide at 18℃; for 19h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 1,2-dimethoxyethane at 20℃; for 12h; Inert atmosphere; | 100% |
With indium iodide In dichloromethane at 20℃; for 1h; | 80% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 3h; Heating; | 78% |
With triphenylphosphine; 1-pentyl-3-methylimidazolium bromide at 75℃; for 6h; | 72% |
6-hydroxy-7-methoxy-1-tetralone
isopropyl bromide
6-isopropoxy-7-methoxy-1-tetralone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Heating; | 100% |
sodium 4-methylbenzenesulfonothioate
isopropyl bromide
4-Methylbenzolthiosulfonsaeure-S-isopropylester
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 100% |
With Amberlyst A-26 (Cl(1-) form) 1.) H2O, r.t., 18 h; 2.) benzene, reflux, 25 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at 65℃; for 6h; | 100% |
With potassium hydroxide 1.) DMSO, 2.) 50 - 60 deg C, 1 h; Yield given. Multistep reaction; | |
With potassium hydroxide 1) DMSO, 20 deg C, 2) DMSO, 50-60 deg C, 1.0 h; Yield given. Multistep reaction; |
(E)-3-phenylpropenal
phenyllithium
isopropyl bromide
(+/-)-4-methyl-1,3-diphenylpentan-1-one
Conditions | Yield |
---|---|
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at 20℃; for 7h; Stage #2: isopropyl bromide In tetrahydrofuran Further stages.; | 100% |
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at 20℃; for 7h; Addition; Stage #2: isopropyl bromide In tetrahydrofuran at 20℃; Alkylation; | 100 % Chromat. |
Conditions | Yield |
---|---|
Stage #1: ethanethiol With sodium tetrahydroborate; sodium hydroxide In water at 5℃; Inert atmosphere; Stage #2: isopropyl bromide; tetrabutylammomium bromide In water at 50℃; Inert atmosphere; | 100% |
With potassium hydroxide In ethanol for 0.5h; Heating; | 51% |
3-methoxy-2-hydroxybenzaldehyde
isopropyl bromide
2-isopropoxy-3-methoxy-benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃; Industry scale; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 110℃; | 99% |
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With tetrabutylammomium bromide; potassium carbonate In acetone at 20℃; for 0.25h; Stage #2: isopropyl bromide In acetone at 20℃; for 24h; | 96% |
6-Pentadecylsalicylic Acid
isopropyl bromide
isopropyl-2-isopropoxy-6-pentadecylbenzoate
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In 4-methyl-2-pentanone for 24h; Reflux; | 100% |
With potassium carbonate In various solvent(s) for 36h; Heating; | |
With benzyltri(n-butyl)ammonium chloride; potassium carbonate In 4-methyl-2-pentanone for 8h; Heating / reflux; | |
With benzyltri(n-butyl)ammonium chloride; potassium carbonate In 4-methyl-2-pentanone for 8h; Heating / reflux; |
3-phenylsalicylic acid
isopropyl bromide
2-isopropoxy-biphenyl-3-carboxylic acid isopropyl ester
Conditions | Yield |
---|---|
With potassium carbonate at 50℃; for 12h; | 100% |
o-hydroxyacetophenone
isopropyl bromide
1-(2-(1-methylethoxy)phenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; | 94% |
With potassium carbonate; potassium iodide In acetone Heating; | 91% |
isopropyl bromide
2,3-dimercaptobenzoic acid methyl ester
2,3-bis-isopropylsulfanyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With lithium methanolate In methanol for 20h; Heating; | 100% |
4-bromoguaiacol
isopropyl bromide
4-bromo-1-isopropoxy-2-methoxy-benzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 90℃; | 100% |
With potassium carbonate In dimethyl sulfoxide at 20 - 55℃; for 2h; | 94% |
With potassium carbonate In dimethyl sulfoxide at 55℃; for 2h; | 84% |
ethyl 5-bromo-4-hydroxy-3-methylbenzofuran-2-carboxylate
isopropyl bromide
ethyl 5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 12h; | 100% |
5-bromo-4-hydroxy-3-methoxybenzaldehyde
isopropyl bromide
3-bromo-4-isopropyloxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; | 100% |
2,2'-dihydroxybiphenyl-3,3'-dicarboxylic acid bisdiethyl amide
isopropyl bromide
2,2'-diisopropoxy-biphenyl-3,3'-dicarboxylic acid bis-diethylamide
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 72h; Inert atmosphere; Reflux; | 100% |
With potassium carbonate In acetone for 72h; Inert atmosphere; Reflux; | 100% |
With potassium carbonate In acetone at 85℃; for 72h; Sealed tube; | 94.7% |
With sodium hydride In N,N-dimethyl-formamide at 60℃; | 80% |
5,6-dihydroxy-indan-1-one
isopropyl bromide
5,6-diisopropoxyindan-1-one
Conditions | Yield |
---|---|
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 8h; | 100% |
5-hydroxy-2,3-dihydro-1H-indene-1-one
isopropyl bromide
5-isopropoxyindan-1-one
Conditions | Yield |
---|---|
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; | 100% |
methyl 4-hydroxybenzofuran-2-carboxylate
isopropyl bromide
methyl 4-isopropoxy-1-benzofuran-2-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; | 100% |
5-chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester
isopropyl bromide
5-chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; | 100% |
2-(3,5-dichloro-2-hydroxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester
isopropyl bromide
2-(3,5-dichloro-2-isopropoxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 110℃; for 2.5h; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Reflux; | 100% |
With potassium carbonate In acetonitrile at 20℃; for 24h; Reflux; | 87% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2.5h; | 58% |
With potassium carbonate In acetonitrile at 80℃; for 16h; | 47% |
1-vinylimidazole
isopropyl bromide
1-vinyl-3-isopropylimidazolium bromide
Conditions | Yield |
---|---|
for 16h; Reflux; | 100% |
2-(4-bromo-phenyl)-5-hydroxy-benzofuran-3-carboxylic acid ethyl ester
isopropyl bromide
ethyl 2-(4-bromophenyl)-5-isopropoxybenzofuran-3-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 60℃; for 4h; | 100% |
Stage #1: 2-(4-bromo-phenyl)-5-hydroxy-benzofuran-3-carboxylic acid ethyl ester With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 0.333333h; Stage #2: isopropyl bromide In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
With potassium carbonate In acetonitrile for 2h; Reflux; | 72% |
With potassium carbonate In acetone for 18h; Inert atmosphere; Reflux; |
Reported in EPA TSCA Inventory.
DOT Classification: 3; Label: Flammable Liquid
2-Bromopropane (CAS NO.75-26-3) is may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine, or with phosphorus tribromide.
1. Introduction of 2-Bromopropane
2-Bromopropane, its cas register number is 75-26-3. It also can be called Isopropyl bromide; Propane, 2-bromo-; 2-Isothiocyanatopropane. It is a colourless liquid.
2-Bromopropane is a colorless liquid. It is used for introducing the isopropyl functional group in organic synthesis.
2. Properties of 2-Bromopropane
XLogP3-AA: 1.8
EINECS: 200-855-1
Melting Point: -89 °C
Surface Tension: 23.1 dyne/cm
Density: 1.342 g/cm3
Flash Point: 19.4 °C
Enthalpy of Vaporization: 28.33 kJ/mol
Boiling Point: 60.6 °C at 760 mmHg
Vapour Pressure: 205 mmHg at 25°C
Refractive index: n20/D 1.425(lit.)
Storage temp.: Flammables area
Water Solubility: 0.3 g/100 mL
Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
Product Categories: Organics
3. Toxicity of 2-Bromopropane
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LC50 | inhalation | 36gm/m3 (36000mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(4), Pg. 55, 1974. | |
mouse | LC50 | inhalation | 31171ppm/4H (31171ppm) | BEHAVIORAL: AGGRESSION | Industrial Health. Vol. 34, Pg. 403, 1996. |
mouse | LD50 | intraperitoneal | 4837mg/kg (4837mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(12), Pg. 52, 1976. |
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