Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); hydrogen bromide In toluene at 0℃; for 2h; Reagent/catalyst; Solvent; | 92% |
A
1,5-dibromo-pentane
Conditions | Yield |
---|---|
With bromine In tetrahydrofuran under N2, stirred at room temp. for 10 min; solvent removed under reduced pressure, residue dissolved (CH2Cl2), chromy. (alumina, hexane, CH2Cl2); | A >90 B 91% |
Conditions | Yield |
---|---|
With hydrogen bromide In octane; water at 148 - 150℃; for 6h; Temperature; Dean-Stark; | 88% |
With sulfuric acid; water; hydrogen bromide | |
With hydrogen bromide | |
With hydrogen bromide at 80 - 90℃; | |
With 2,6-dimethylpyridine; carbon tetrabromide In N,N-dimethyl-formamide at 23 - 35℃; for 6h; UV-irradiation; | 96 %Spectr. |
Conditions | Yield |
---|---|
With hydrogen bromide In toluene for 9h; Substitution; Heating; | A n/a B 81% |
Conditions | Yield |
---|---|
With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine In dichloromethane at 20℃; for 0.15h; Appel Halogenation; | 80% |
With sulfuric acid; hydrogen bromide for 3h; Heating; | 79% |
With trimethylsilyl bromide; iodine(I) bromide for 2h; Heating; | 71% |
TETRAHYDROPYRANE
acetic anhydride
A
1,5-dibromo-pentane
B
5-bromo-1-pentanyl acetate
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With phosphorus pentabromide Destillation des Produkts unter vermindertem Druck; | |
With phosphorus pentabromide anschliessend Behandeln mit Wasser; | |
With bromine; phosphorus tribromide 1.) from 24 deg C to 34 deg C, 2.) reflux, 2 h; Yield given. Multistep reaction; | |
With phosphorus pentabromide anschliessend Behandeln mit Wasser; |
Conditions | Yield |
---|---|
beim Leiten von Bromdampf ueber die Schmelze; |
1,5-diphenoxypentane
1,5-dibromo-pentane
Conditions | Yield |
---|---|
With hydrogen bromide at 170℃; |
diethyl ether
pentamethylenebis(magnesium bromide)
2-bromoallyl bromide
A
1,5-dibromo-pentane
B
2,10-dibromo-undeca-1,10-diene
C
2-bromo-1-octene
Conditions | Yield |
---|---|
Produkt5: 2.15-Dibrom-hexadecadien-(1.15); |
Conditions | Yield |
---|---|
With dibenzoyl peroxide at 100℃; under 228007 - 257428 Torr; |
N-benzoylpiperidine
phosphorus pentabromide
A
1,5-dibromo-pentane
B
benzonitrile
Conditions | Yield |
---|---|
beim Destillieren des Reaktionsprodukts; | |
beim Destillieren des Reaktionsprodukts; |
1,5-dibromo-pentane
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid at 100℃; im Rohr; |
ethene
water
1,2-dibromomethane
dibenzoyl peroxide
A
1,5-dibromo-pentane
B
1,3-dibromo-propane
Conditions | Yield |
---|---|
at 100℃; under 228007 - 257428 Torr; |
Conditions | Yield |
---|---|
at 100℃; |
A
1,5-dibromo-pentane
B
1-bromo-5-chloropentane
Conditions | Yield |
---|---|
With sulfuric acid; hydrogen bromide |
1,5-diphenoxypentane
hydrogen bromide
1,5-dibromo-pentane
Conditions | Yield |
---|---|
at 170℃; im geschlossenen Rohr; |
A
1,5-dibromo-pentane
Conditions | Yield |
---|---|
at 160 - 190℃; under 25 - 30 Torr; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: concentrated sulfuric acid 2: sodium; alcohol 3: hydrogen bromide / 80 - 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitrous acid 2: hydrobromic acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium; alcohol 2: hydrogen bromide / 80 - 90 °C View Scheme |
A
1,5-dibromo-pentane
B
(trans)-(4-hydroxy-cyclohexyl)-carbamic acid benzyl ester
Conditions | Yield |
---|---|
With sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 80℃; for 1h; Inert atmosphere; | 100% |
With potassium carbonate In water at 120℃; for 0.333333h; microwave irradiation; | 96% |
With potassium carbonate In water at 120℃; for 0.333333h; microwave irradiation; | 96% |
1,5-dibromo-pentane
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
N-(4-Bromopentyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 100% |
1,5-dibromo-pentane
6-(3,4-difluorophenyl)-1,6-dihydro-5-methoxycarbonyl-2-methoxymethyl-4-methylpyrimidine
1-(5-bromopent-1-yl)-6-(3,4-difluorophenyl)-1,6-dihydro-5-methoxycarbonyl-2-methoxymethyl-4-methylpyrimidine
Conditions | Yield |
---|---|
Stage #1: 6-(3,4-difluorophenyl)-1,6-dihydro-5-methoxycarbonyl-2-methoxymethyl-4-methylpyrimidine With sodium hydride In tetrahydrofuran for 0.333333h; Metallation; Stage #2: 1,5-dibromo-pentane In tetrahydrofuran Alkylation; Heating; | 100% |
With NaH In tetrahydrofuran; mineral oil | |
With NaH In tetrahydrofuran; mineral oil |
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere; | 100% |
Stage #1: pyridine-2-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 1,5-dibromo-pentane In tetrahydrofuran at -78 - 20℃; for 10h; | 88% |
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere; | 74% |
In water; dimethyl sulfoxide; ethyl acetate; isopropyl alcohol | 72% |
Conditions | Yield |
---|---|
In tetrahydrofuran Br(CH2)5Br was added to Zn powder in THF in a sealed and evacuated glass apparatus, mixt. was stirred for 5 h at 65°C; detd. by titrn.; | 100% |
3-bromo-5-hydroxybenzoic acid ethyl ester
1,5-dibromo-pentane
Ethyl 3-bromo-5-[(5-bromopentyl)oxy]benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 100℃; | 100% |
In acetonitrile at 20℃; for 120h; | 93% |
In methanol at 0 - 55℃; for 64h; Inert atmosphere; | 90% |
1,5-dibromo-pentane
C18H20N2O
1-(3,4-dihydroquinolin-1(2H)-yl)-3-phenyl-2-(piperidin-1-yl)propan-1-one
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In acetonitrile for 17h; Reflux; | 100% |
1,5-dibromo-pentane
4-hydroxy-3-methoxybenzoic acid methyl ester
1',5'-bis<2-methoxy-(4-methoxycarbonyl)phenoxy>pentane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 3h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide for 3h; Inert atmosphere; | 7.92 g |
Conditions | Yield |
---|---|
In acetonitrile Solvent; Reflux; | 100% |
1,5-dibromo-pentane
diethyl malonate
tetraethyl heptane-1,1,7,7-tetracarboxylate
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With sodium ethanolate for 1h; Reflux; Industrial scale; Stage #2: 1,5-dibromo-pentane for 1h; Reflux; Industrial scale; | 100% |
Stage #1: diethyl malonate With sodium ethanolate In ethanol at 40℃; Inert atmosphere; Stage #2: 1,5-dibromo-pentane In ethanol at 55℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: gentitein With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.8% |
Stage #1: gentitein With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
Conditions | Yield |
---|---|
Stage #1: isogentisine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.7% |
Stage #1: isogentisine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
Conditions | Yield |
---|---|
Stage #1: 7-bromo-1,3-dihydroxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.6% |
Stage #1: 7-bromo-1,3-dihydroxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
1,5-dibromo-pentane
1,3-dihydroxyxanthone
1-hydroxy-3-(5-bromo-pentyloxy)-9H-xanthene-9-one
Conditions | Yield |
---|---|
Stage #1: 1,3-dihydroxyxanthone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.4% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; | 82% |
With potassium carbonate In acetone at 60℃; for 4h; Reflux; | 72.39% |
Conditions | Yield |
---|---|
Stage #1: 7-chloro-1,3-dihydroxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.2% |
Stage #1: 7-chloro-1,3-dihydroxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
Conditions | Yield |
---|---|
Stage #1: 1,3-dihydroxy-8-methoxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.2% |
Stage #1: 1,3-dihydroxy-8-methoxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
Conditions | Yield |
---|---|
Stage #1: 1,3-dihydroxy-6,7-dimethoxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.2% |
Stage #1: 1,3-dihydroxy-6,7-dimethoxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In chloroform for 15h; Reflux; | 99% |
With potassium carbonate In acetonitrile Reflux; | 77% |
Stage #1: 1,5-dibromo-pentane With potassium carbonate In acetonitrile at 100℃; Stage #2: piperidine at 100℃; | 67% |
1,5-dibromo-pentane
1,5-diazidopentane
Conditions | Yield |
---|---|
With sodium azide In water; N,N-dimethyl-formamide at 80℃; for 20h; | 99% |
With sodium azide In N,N-dimethyl-formamide at 60℃; for 10h; | 96% |
With sodium azide In water at 120 - 140℃; Microwave irradiation; | 94% |
Conditions | Yield |
---|---|
With 18-crown-6 ether In acetonitrile for 16h; Heating; | 99% |
In ethanol; water Heating; | 87% |
Conditions | Yield |
---|---|
In ethanol at 80℃; for 48h; | 99% |
In acetonitrile for 2.5h; Reflux; | 90% |
In ethanol for 48h; Reflux; | 83% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol | 99% |
With sodium hydroxide In ethanol | 99% |
Conditions | Yield |
---|---|
In ethyl acetate at 20 - 150℃; for 0.333333h; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran for 20h; Inert atmosphere; Reflux; | 99% |
With potassium carbonate In acetonitrile Reflux; | 93% |
Stage #1: p-cresol With sodium hydroxide In ethanol for 0.5h; Cooling with ice; Stage #2: 1,5-dibromo-pentane In ethanol Reflux; | 83.1% |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 48h; Inert atmosphere; Schlenk technique; | 99% |
1,5-dibromo-pentane
Conditions | Yield |
---|---|
In methanol at 55℃; for 144h; | 99% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at 0 - 20℃; for 5h; diastereoselective reaction; | 99% |
1,5-dibromo-pentane
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 4h; Inert atmosphere; Reflux; | 99% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 110℃; for 3h; Microwave irradiation; | 95% |
1,5-dibromo-pentane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1.5h; Inert atmosphere; | 99% |
IUPAC Name: 1,5-dibromopentane
Empirical Formula: C5H10Br2
Molecular Weight: 229.9409g/mol
EINECS: 203-849-7
Structure of 1,5-Dibromopentane (CAS NO.111-24-0):
Index of Refraction: 1.503
Molar Refractivity: 40.67 cm3
Molar Volume: 137.4 cm3
Polarizability: 16.12×10-24cm3
Surface Tension: 35.4 dyne/cm
Density: 1.673 g/cm3
Flash Point: 94.7 °C
Enthalpy of Vaporization: 44.22 kJ/mol
Melting Point: −34 °C(lit.)
Boiling Point: 224.5 °C at 760 mmHg
Vapour Pressure: 0.136 mmHg at 25°C
Water Solubility: insoluble
Product Categories: Organics;Miscellaneous;DIBROMOALKANE;Bromine Compounds;alpha,omega-Bifunctional Alkanes;alpha,omega-Dibromoalkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
Canonical SMILES: C(CCBr)CCBr
InChI: InChI=1S/C5H10Br2/c6-4-2-1-3-5-7/h1-5H2
InChIKey: IBODDUNKEPPBKW-UHFFFAOYSA-N
1,5-Dibromopentane (CAS NO.111-24-0) is used for synthetic organic intermediates
1. | mmo-sat 10 µmol/plate | MUREAV Mutation Research. 141 (1984),11. | ||
2. | dnr-esc 10 µL/disc | CNREA8 Cancer Research. 34 (1974),2576. |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Mutation data reported. When heated to decomposition it emits toxic fumes of Br−. See also n-PENTANE and BROMIDES.
The Hazard Codes of 1,5-DIBROMOPENTANE(111-24-0): Xi,Xn
HS Code:29033036
The Risk Statements information of 1,5-DIBROMOPENTANE(111-24-0):
22: Harmful if swallowed
36/38: Irritating to eyes and skin
The Safety Statements information of 1,5-DIBROMOPENTANE(111-24-0):
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37/39: Wear suitable gloves and eye/face protection
WGK Germany:3
RTECS:SA0320000
1,5-Dibromopentane , its cas register number is 111-24-0. It also can be called 4-01-00-00314 (Beilstein Handbook Reference) ; AI3-20307 ; CCRIS 8918 ; NSC 5373 ; Pentamethylene bromide ; Pentamethylene dibromide . 1,5-Dibromopentane (CAS NO.111-24-0) is a clear colorless to yellow-brownish liquid.
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