Conditions | Yield |
---|---|
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -78 - 20℃; for 12h; Darkness; chemoselective reaction; | 97% |
With sulfuric acid; hydrogen bromide | |
With hydrogen bromide folgendes Erhitzen; |
Conditions | Yield |
---|---|
With hydrogen bromide In toluene for 13h; Substitution; Heating; | A n/a B 79% |
With hydrogen bromide In toluene for 24h; Heating; | A 1% B 69% |
O-6-oxohexyl dimethylcarbamothioate
A
1 ,6-dibromohexane
B
6-bromohexanal
Conditions | Yield |
---|---|
With 4-(bromomethylene)morpholin-4-ium bromide In dichloromethane at 0℃; for 1h; Inert atmosphere; | A 5% B 75% |
O-6-hydroxyhexyl dimethylcarbamothioate
A
1 ,6-dibromohexane
B
1-bromo-6-hexanol
C
C7H13BrO2
D
6-bromohexyl dimethylthiocarbamate
Conditions | Yield |
---|---|
With 4-(bromomethylene)morpholin-4-ium bromide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; | A 18% B 13% C 10% D 59% |
O-6-hydroxyhexyl dimethylcarbamothioate
A
1 ,6-dibromohexane
B
1-bromo-6-hexanol
C
6-bromohexyl dimethylthiocarbamate
Conditions | Yield |
---|---|
With 4-(bromomethylene)morpholin-4-ium bromide In dichloromethane at 0℃; for 24h; Inert atmosphere; | A 44% B 4% C 50% |
bis(trichloromethyl) carbonate
acrylic acid methyl ester
6-azido-hexylamine
1 ,6-dibromohexane
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane | 40% |
O-6-(tetrahydro-2H-pyran-2-yloxy)hexyl dimethylcarbamothioate
A
1 ,6-dibromohexane
B
2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran
C
1-bromo-6-hexanol
D
C7H13BrO2
Conditions | Yield |
---|---|
With 4-(bromomethylene)morpholin-4-ium bromide In dichloromethane at 0℃; for 1.5h; Inert atmosphere; | A 5% B 14% C 27% D 23% |
O-6-(tert-butyldimethylsiloxy)hexyl dimethylcarbamothioate
A
1 ,6-dibromohexane
B
1-bromo-6-hexanol
C
tert-butyldimethylsilanol
D
(6-bromohexyloxy)-tert-butyldimethylsilane
Conditions | Yield |
---|---|
With 4-(bromomethylene)morpholin-4-ium bromide In dichloromethane at 0℃; for 2h; Inert atmosphere; | A 10% B 21% C 13% D 26% |
Conditions | Yield |
---|---|
With hydrogen bromide at -78℃; Irradiation.mit UV-Licht; |
1,3-dibromo-propane
A
1 ,6-dibromohexane
B
propene
C
cyclopropane
Conditions | Yield |
---|---|
unter Luminescenz; |
1 ,6-dibromohexane
Conditions | Yield |
---|---|
With hydrogen bromide at 120℃; |
1 ,6-dibromohexane
Conditions | Yield |
---|---|
With phosphorus pentabromide nachfolgende Destillation des Reaktionsproduktes unter 20 mm Druck; |
1 ,6-dibromohexane
Conditions | Yield |
---|---|
With hydrogen bromide at 150℃; |
1 ,6-dibromohexane
Conditions | Yield |
---|---|
With hydrogen bromide at 150 - 160℃; |
1 ,6-dibromohexane
Conditions | Yield |
---|---|
With phosphorus pentabromide |
Conditions | Yield |
---|---|
at 120 - 130℃; |
Conditions | Yield |
---|---|
at -78℃; UV-Strahlen.Irradiation; |
1,6-bis-(6-hydroxy-hexyloxy)-hexane
hydrogen bromide
1 ,6-dibromohexane
Conditions | Yield |
---|---|
at 100℃; |
bis-(6-bromo-hexyl)-ether
1 ,6-dibromohexane
Conditions | Yield |
---|---|
at 125 - 126℃; im Rohr; |
1,6-hexanediol
hydrogen bromide
A
1 ,6-dibromohexane
B
bis-(6-bromo-hexyl)-ether
Conditions | Yield |
---|---|
at 195℃; |
N,N'-dibenzoylhexane-1,6-diamine
phosphorus pentabromide
1 ,6-dibromohexane
Conditions | Yield |
---|---|
nachfolgend Destillation unter vermindertem Druck; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: durch Reduktion 2: hydrogen bromide / 120 - 130 °C View Scheme |
A
1 ,6-dibromohexane
B
(trans)-(4-hydroxy-cyclohexyl)-carbamic acid benzyl ester
1 ,6-dibromohexane
dimethyl amine
N,N,N',N'-tetramethylhexamethylenediamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 24h; | 100% |
In chloroform at 20℃; for 24h; | 100% |
With sodium carbonate In ethanol; water for 24h; Heating; | 98% |
1 ,6-dibromohexane
trimethylphosphane
(6-Bromhexyl)trimethylphosphoniumbromid
Conditions | Yield |
---|---|
In toluene for 72h; Ambient temperature; | 100% |
1 ,6-dibromohexane
3-(4-bromophenyl)benzo[d]isoxazol-6-ol
6-(6-bromohexyloxy)-3-(4-bromophenyl)benzo[d]isoxazole
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 65℃; for 18h; | 100% |
1 ,6-dibromohexane
(4-bromophenyl)(4-hydroxy-2-methylsulfanylphenyl)methanone
[4-[6-(bromo)hexyloxy]-2-methylsulfanylphenyl](4-bromophenyl)methanone
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 100% |
Conditions | Yield |
---|---|
In ethanol at 100℃; for 24h; | 100% |
1 ,6-dibromohexane
1-azido-6-bromohexane
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 100% |
With sodium azide In water; N,N-dimethyl-formamide at 60℃; for 28h; | 98% |
With sodium azide In water; N,N-dimethyl-formamide at 60℃; for 24h; | 80% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 75℃; | 100% |
Conditions | Yield |
---|---|
In acetone at 40℃; for 24h; | 99.9% |
Conditions | Yield |
---|---|
Stage #1: isogentisine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.8% |
Stage #1: isogentisine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1 ,6-dibromohexane 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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.6% |
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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 99.4% |
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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
1 ,6-dibromohexane
1,6-diazidohexane
Conditions | Yield |
---|---|
With sodium azide In water; N,N-dimethyl-formamide at 80℃; for 20h; | 99% |
With sodium azide; potassium iodide In water; N,N-dimethyl-formamide at 90℃; for 120h; | 99% |
With sodium azide In water; N,N-dimethyl-formamide at 80℃; for 22h; | 98% |
1 ,6-dibromohexane
4-Hydroxyacetophenone
1,1'-<1,6-hexanediylbis(oxy-4,1-phenylene)>bisethanone
Conditions | Yield |
---|---|
Stage #1: 4-Hydroxyacetophenone With potassium hydroxide In ethanol at 50 - 60℃; for 0.25h; Stage #2: 1 ,6-dibromohexane In ethanol for 18h; Reflux; | 99% |
With potassium carbonate In acetone for 18h; Reflux; | 89% |
With Aliquat 336; potassium carbonate; potassium iodide In acetone Heating; | 88% |
1 ,6-dibromohexane
N,N-dimethylhexadecylamine
1,6-bis(N-hexadecyl-N,N-dimethylammonium)hexane dibromide
Conditions | Yield |
---|---|
In ethanol at 80℃; for 48h; | 99% |
In acetonitrile at 82℃; for 48h; Menshutkin Reaction; | 97% |
In ethanol at 80℃; for 48h; Reflux; | 83% |
Conditions | Yield |
---|---|
In acetonitrile for 0.35h; Microwave irradiation; | 99% |
With potassium carbonate; potassium iodide at 100℃; for 2h; microwave irradiation; | 97% |
With potassium carbonate; potassium iodide In acetonitrile Heating; |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol Heating; | 99% |
Conditions | Yield |
---|---|
99% | |
99% |
Conditions | Yield |
---|---|
In acetonitrile at 82℃; for 48h; Menshutkin Reaction; | 99% |
In ethanol at 80℃; for 48h; | 80% |
In ethanol Reflux; |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 48h; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With triethylamine In ethanol at 60℃; for 72h; | 99% |
Conditions | Yield |
---|---|
In diethyl ether at 40℃; for 12h; Temperature; | 99% |
1 ,6-dibromohexane
methyl-4,5-dihydro-1H-imidazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; for 1h; | 99% |
at 20 - 100℃; for 3.33333h; | 68% |
Conditions | Yield |
---|---|
In acetonitrile at 82℃; for 48h; Menshutkin Reaction; | 99% |
In acetonitrile at 60℃; for 24h; | 92% |
1 ,6-dibromohexane
1,3-dihydroxyxanthone
1-hydroxy-3-(6-bromo-hexyloxy)-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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 98.7% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; | 80% |
With potassium carbonate In acetone for 24h; Reflux; | 51% |
With potassium carbonate In acetone for 24h; Reflux; | 51% |
Stage #1: 1,3-dihydroxyxanthone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
Conditions | Yield |
---|---|
Stage #1: gentitein With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 98.6% |
Stage #1: gentitein With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1 ,6-dibromohexane 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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 98.6% |
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 ,6-dibromohexane 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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 20h; | 98.6% |
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 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 12.5h; |
1-Methylpyrrolidine
1 ,6-dibromohexane
1,6-bis(N-methylpyrrolidinium)hexane bromide
Conditions | Yield |
---|---|
for 24h; Reflux; | 98% |
In acetone at 20℃; | |
In methanol at 20℃; for 96h; | |
With ethanol |
pyridine
1 ,6-dibromohexane
[1,1'-(hexane-1,6-diyl)bis(pyridinium)] dibromide
Conditions | Yield |
---|---|
for 24h; Heating; | 98% |
In acetonitrile at 70℃; for 24h; | 93% |
In acetonitrile Reflux; | 88% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone at 65℃; | 98% |
With potassium carbonate; potassium iodide In acetone at 60℃; for 72h; | 96% |
With potassium carbonate; potassium iodide In acetone at 65℃; Inert atmosphere; | 95.2% |
Molecular Structure of 1,6-Dibromohexane (CAS NO.629-03-8):
IUPAC Name: 1,6-dibromohexane
Empirical Formula: C6H12Br2
Molecular Weight: 243.9675
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 5
Polar Surface Area: 0 Å2
Index of Refraction: 1.5
Molar Refractivity: 45.3 cm3
Molar Volume: 153.9 cm3
Surface Tension: 35.2 dyne/cm
Density: 1.584 g/cm3
Flash Point: 110.8 °C
Enthalpy of Vaporization: 46.17 kJ/mol
Boiling Point: 244.1 °C at 760 mmHg
Vapour Pressure: 0.0483 mmHg at 25°C
EINECS: 211-067-2
Melting point: −2-2.5 °C(lit.)
Product Categories: Industrial/Fine Chemicals; Dibromoalkane; Bromine Compounds; alpha,omega-Bifunctional Alkanes; alpha,omega-Dibromoalkanes; Monofunctional & alpha,omega-Bifunctional Alkanes
1. | skn-rbt 500 mg MLD | FCTOD7 Food and Chemical Toxicology. 20 (1982),563. | ||
2. | eye-rbt 100 mg MLD | FCTOD7 Food and Chemical Toxicology. 20 (1982),573. | ||
3. | eye-rbt 100 mg/30S rns MLD | FCTOD7 Food and Chemical Toxicology. 20 (1982),573. | ||
4. | mmo-sat 10 µmol/plate | MUREAV Mutation Research. 141 (1984),11. | ||
5. | ipr-mus LD50:270 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 14 (1964),668. |
Reported in EPA TSCA Inventory.
Poison by intraperitoneal route. A skin and eye irritant. Mutation data reported. When heated to decomposition it emits very toxic fumes of Br−. See also BROMIDES.
Hazard Codes: T,N,C
Risk Statements: 25-51/53
R25 :Toxic if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 36-45-61
S36:Wear suitable protective clothing.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
RTECS: MO1515000
HazardClass: 9
PackingGroup; III
HS Code: 29033036
1,6-Dibromohexane , with CAS number of 629-03-8, can be called Hexamethylene dibromide ; 1,6-Dibromo-n-hexane ; a,w-Dibromohexane . It is a colourless or pale yellow liquid. 1,6-Dibromohexane (CAS NO.629-03-8) can be used as intermediates in organic synthesis, or for the production of lowering blood pressure drug-Rokko bromide .
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