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111-83-1 Usage

Chemical Properties

clear colourless to yellow-brown liquid. insoluble in water, miscible with ethanol and ether.

Uses

1-Bromooctane is used in organic synthesis. It is also used as an extraction solvent in the determination of volatile organic compounds present in water samples. Further, it is used in the preparation of quaternary ammonium chloride-modified poly(propylenimine) dendrimers.

Preparation

1-Bromooctane is prepared by reacting octanol with hydrobromic acid. After the sodium bromide was completely dissolved with sulfuric acid, n-octanol was added, heated to reflux for 7-8 hours, cooled and diluted with water, the organic phase was separated, washed with water, concentrated sulfuric acid, water, and 10% sodium carbonate solution in turn, and washed with anhydrous sulfuric acid. Sodium dry. Distillation of 196-200°C, or 91-93°C (2.93kPa) fraction, is the finished product of 1-bromooctane. The yield is over 90%.

Synthesis Reference(s)

Chemistry Letters, 6, p. 1117, 1977Journal of the American Chemical Society, 96, p. 8115, 1974 DOI: 10.1021/ja00833a048Tetrahedron Letters, 28, p. 4445, 1987 DOI: 10.1016/S0040-4039(00)96534-1

Purification Methods

Shake the bromide with H2SO4, wash it with water, dry with K2CO3 and fractionally distil it. [Beilstein 1 IV 422.]

Check Digit Verification of cas no

The CAS Registry Mumber 111-83-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 111-83:
(5*1)+(4*1)+(3*1)+(2*8)+(1*3)=31
31 % 10 = 1
So 111-83-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H17Br/c1-2-3-4-5-6-7-8-9/h2-8H2,1H3

111-83-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A14722)  1-Bromooctane, 98+%   

  • 111-83-1

  • 250g

  • 142.0CNY

  • Detail
  • Alfa Aesar

  • (A14722)  1-Bromooctane, 98+%   

  • 111-83-1

  • 1000g

  • 447.0CNY

  • Detail
  • Alfa Aesar

  • (A14722)  1-Bromooctane, 98+%   

  • 111-83-1

  • 5000g

  • 2040.0CNY

  • Detail
  • Aldrich

  • (152951)  1-Bromooctane  99%

  • 111-83-1

  • 152951-100G

  • 253.89CNY

  • Detail
  • Aldrich

  • (152951)  1-Bromooctane  99%

  • 111-83-1

  • 152951-500G

  • 779.22CNY

  • Detail

111-83-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Bromooctane

1.2 Other means of identification

Product number -
Other names 1-BROMO OCTANE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:111-83-1 SDS

111-83-1Synthetic route

1-Fluoro-octane
463-11-6

1-Fluoro-octane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With dibromobis(cyclopentadienyl)titanium(IV); triisobutylaluminum; 1,2-dibromomethane In hexane at 20℃; for 24h; Reagent/catalyst;99%
With hydrogen bromide; cetyltributylphosphonium bromide at 130℃; for 8.5h;86%
With magnesium bromide In diethyl ether at 25℃; for 10h;41 % Chromat.
With aluminum tri-bromide In chlorobenzene at 20℃; for 1h;
octanol
111-87-5

octanol

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With carbon tetrabromide; polystyrene-supported triphenylphosphine In chloroform at 20℃; for 0.333333h;98%
With sulfuric acid; hydrogen bromide In water at 60℃; Temperature; Flow reactor; Green chemistry;98%
With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate; bromine at 80℃; for 2h;96%
C14H35N3PS(1+)
103514-65-4

C14H35N3PS(1+)

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With bromide In N,N-dimethyl-formamide96%
n-octyl methanesulfonate
16156-52-8

n-octyl methanesulfonate

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With potassium bromide; O3Si(CH2)3P(C4H9)3Br; silica gel In carbon dioxide; water at 70℃; under 97509.8 Torr; for 5h;95%
With potassium bromide; tributylphosphonium salts bonded to .. In water; toluene at 60℃; Rate constant; variation of catalists;
With 2-hexadecyl-1,3-bis-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)propane; sodium bromide In toluene at 50℃; Rate constant; also with KBr; further phase-transfer catalysts;
oct-1-ene
111-66-0

oct-1-ene

A

1-bromo-octane
111-83-1

1-bromo-octane

B

2-bromooctane
557-35-7, 60251-57-2

2-bromooctane

Conditions
ConditionsYield
With hydrogen bromide In hexane at 24.9℃; for 48h; Mechanism; Product distribution; other reagent concentrations and other reaction temperatures;A 95%
B 5%
With borane; bromine; sodium methylate 1.) THF, 0 deg C, 2.) 0 deg C, 3.) MeOH, 0 deg C; Yield given. Multistep reaction;
1-octyl p-toluenesulfonate
3386-35-4

1-octyl p-toluenesulfonate

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 50℃; for 5h; Inert atmosphere; Green chemistry;93%
With lithium bromide
methoxymethyl octyl ether
88738-43-6

methoxymethyl octyl ether

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With phosphotungstic acid; tetrabutylammomium bromide at 130 - 142℃; for 0.0333333h; Microwave irradiation; Ionic liquid; chemoselective reaction;91%
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0666667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;82%
1-methoxyoctane
929-56-6

1-methoxyoctane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With hydrogen bromide; phosphorus tribromide at 125℃; for 0.666667h;90%
1-Chlorooctane
111-85-3

1-Chlorooctane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h;89%
With pyridine; tributyltin bromide at 100℃; Thermodynamic data; Equilibrium constant; Δ G;
With lithium bromide; tetrahexylammonium bromide In water at 98℃; for 72h; various metal halide salts; bromine-chloride exchange;
ethoxymethyl octyl ether
796965-95-2

ethoxymethyl octyl ether

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With phosphotungstic acid; tetrabutylammomium bromide at 130 - 142℃; for 0.0333333h; Microwave irradiation; Ionic liquid; chemoselective reaction;89%
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0666667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;83%
1-Iodooctane
629-27-6

1-Iodooctane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With iodobenzene dibromide In dichloromethane for 1h; Ambient temperature;85%
With pyridine; tributyltin bromide at 100℃; Thermodynamic data; Equilibrium constant; Δ G;36 % Spectr.
With n-hexylzirconocene chloride; [nickel(II) (4,4'-di-tert-butyl-2,2'-bipyridine)(bromide)2]; tetrabutylammonium p-toluenesulfonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;
trimethyl(oct-1-yloxy)silane
14246-16-3

trimethyl(oct-1-yloxy)silane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With trimethylsilyl bromide; iodine(I) bromide for 6h; Heating;85%
1-methoxy-4-octyloxymethyl benzene
54384-75-7

1-methoxy-4-octyloxymethyl benzene

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 30℃; for 2.5h;85%
1,3-Diisopropyl-2-octyl-isourea
52770-75-9

1,3-Diisopropyl-2-octyl-isourea

A

1,3-diisopropylurea
4128-37-4

1,3-diisopropylurea

B

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; tetrabutylammomium bromide In chloroform at 65℃; for 7.5h;A n/a
B 83%
oct-1-ene
111-66-0

oct-1-ene

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
Stage #1: oct-1-ene With dibenzoyl peroxide at 30℃; for 0.5h;
Stage #2: With hydrogen bromide at 20℃; for 0.5h; Temperature;
82.2%
With hydrogenchloride; borane; chloroamine-T; sodium bromide 1.) 0 deg C, 1 h, THF, 2.) 0 deg C, 15 min, H2O, THF; Yield given. Multistep reaction;
With hydrogen bromide In hexane at -78.1℃; for 48h; Yield given;
Multi-step reaction with 2 steps
1: bis(1,5-cyclooctadiene)diiridium(I) dichloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere; Glovebox
2: benzenesulfonyl bromide; trimethylsilyl trifluoromethanesulfonate; 2-methoxybenzo[d][1,3,2]dioxaborole / dichloromethane; benzene; methanol / 16 h / 70 °C / Inert atmosphere
View Scheme
5,6,8,9-tetrahydro-14-octyl-7-phenyldibenzoacridinium bromide
76207-90-4

5,6,8,9-tetrahydro-14-octyl-7-phenyldibenzoacridinium bromide

A

5,6,8,9-tetrahydro-7-phenyldibenzolacridine
57366-68-4

5,6,8,9-tetrahydro-7-phenyldibenzolacridine

B

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With acetonitrile 1.) reflux, 4 h, 2.) 0 deg C, 6 h;A n/a
B 80%
octanol
111-87-5

octanol

A

di(n-octyl)phosphite
1809-14-9

di(n-octyl)phosphite

B

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With phosphorus tribromide In diethyl ether at 0 - 25℃; for 6h;A 12.2%
B 77.3%
Octanethiol
111-88-6

Octanethiol

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 12h;75%
4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane
66217-56-9

4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; 2-methoxybenzo[d][1,3,2]dioxaborole; benzenesulfonyl bromide In methanol; dichloromethane; benzene at 70℃; for 16h; Inert atmosphere;66%
1-methoxyoctane
929-56-6

1-methoxyoctane

A

1-bromo-octane
111-83-1

1-bromo-octane

B

mono-1-methylheptyl phosphonate
35103-75-4

mono-1-methylheptyl phosphonate

Conditions
ConditionsYield
With hydrogen bromide; phosphorus tribromide at 50℃; for 0.666667h;A 15%
B 50%
4-hydroxybutyl octyl sulfoxide
7333-16-6

4-hydroxybutyl octyl sulfoxide

A

1-bromo-octane
111-83-1

1-bromo-octane

B

4-Bromo-1-butanol
33036-62-3

4-Bromo-1-butanol

C

octyl cyclobutyl sulfonium bromide

octyl cyclobutyl sulfonium bromide

D

4-bromobutyl octyl sulfone
80623-45-6

4-bromobutyl octyl sulfone

Conditions
ConditionsYield
With bromine In acetonitrile at -25℃; for 2h; Further byproducts given;A n/a
B n/a
C 24%
D 46%
1-(methylethoxy)octane
68975-45-1

1-(methylethoxy)octane

A

1-bromo-octane
111-83-1

1-bromo-octane

B

mono-1-methylheptyl phosphonate
35103-75-4

mono-1-methylheptyl phosphonate

Conditions
ConditionsYield
With hydrogen bromide; phosphorus tribromide at 80℃; for 0.666667h;A 45%
B 9%
4-hydroxybutyl octyl sulfoxide
7333-16-6

4-hydroxybutyl octyl sulfoxide

A

1-bromo-octane
111-83-1

1-bromo-octane

B

4-Bromo-1-butanol
33036-62-3

4-Bromo-1-butanol

C

4-hydroxybutanesulfinyl bromide

4-hydroxybutanesulfinyl bromide

D

octanesulfinyl bromide

octanesulfinyl bromide

E

octane-1-sulfonyl bromide

octane-1-sulfonyl bromide

F

octyl cyclobutyl sulfonium bromide

octyl cyclobutyl sulfonium bromide

Conditions
ConditionsYield
With bromine In acetonitrile at -25℃; for 2h; Product distribution;A n/a
B n/a
C n/a
D n/a
E n/a
F 24%
n-octylsilatrane
67007-46-9

n-octylsilatrane

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane for 78h; Ambient temperature;15%
oct-1-ene
111-66-0

oct-1-ene

isopropyl bromide
75-26-3

isopropyl bromide

A

cis-2-octene
7642-04-8

cis-2-octene

B

trans-2-Octene
13389-42-9

trans-2-Octene

C

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
mit UV-Licht.Irradiation;
n-octyl methanesulfonate
16156-52-8

n-octyl methanesulfonate

tetraoctyl ammonium bromide
14866-33-2

tetraoctyl ammonium bromide

A

1-bromo-octane
111-83-1

1-bromo-octane

B

tetraoctylammonium methanesulfonate
70098-05-4

tetraoctylammonium methanesulfonate

Conditions
ConditionsYield
In chlorobenzene at 60℃; Rate constant;
In water; chlorobenzene at 60℃; Kinetics;
n-octyl methanesulfonate
16156-52-8

n-octyl methanesulfonate

3-Tetradecyl-4,10,15-trioxa-1,7-diaza-bicyclo[5.5.5]heptadecane; hydrobromide
92958-33-3

3-Tetradecyl-4,10,15-trioxa-1,7-diaza-bicyclo[5.5.5]heptadecane; hydrobromide

A

1-bromo-octane
111-83-1

1-bromo-octane

B

3-Tetradecyl-4,10,15-trioxa-1,7-diaza-bicyclo[5.5.5]heptadecane; compound with methanesulfonic acid
80322-81-2

3-Tetradecyl-4,10,15-trioxa-1,7-diaza-bicyclo[5.5.5]heptadecane; compound with methanesulfonic acid

Conditions
ConditionsYield
In chlorobenzene at 60℃; Rate constant;
n-octyl methanesulfonate
16156-52-8

n-octyl methanesulfonate

A

1-bromo-octane
111-83-1

1-bromo-octane

B

di-n-octyl ether
629-82-3

di-n-octyl ether

C

potassium mesylate
2386-56-3

potassium mesylate

Conditions
ConditionsYield
With potassium bromide; perhydrodibenzo-18-crown-6 In potassium hydroxide; chlorobenzene at 60℃; for 1h;A 94.4 % Chromat.
B 3 % Chromat.
C n/a
n-octyl methanesulfonate
16156-52-8

n-octyl methanesulfonate

A

1-bromo-octane
111-83-1

1-bromo-octane

B

potassium mesylate
2386-56-3

potassium mesylate

Conditions
ConditionsYield
With potassium bromide In water; benzene at 45℃; gaschromatographic determination of formation of octyl bromide in dependence on time, addition of various quaternary onium salts; also with solvent CHCl3/H2O; two phase system and homogeneous system;
With potassium bromide; (C16H33)Bu3P(1+)*Br(1-) In water; chlorobenzene at 60℃; Rate constant; other quaternary ammonium or phosphonium;
With potassium bromide; (C8H17)4N(1+)*Br(1-) In water; chlorobenzene at 35℃; Rate constant; other solvents;
octanol
111-87-5

octanol

dimethylamino-2,N,N' diphenyl-1,3 diazaphospholane-1,3,2
81106-32-3

dimethylamino-2,N,N' diphenyl-1,3 diazaphospholane-1,3,2

1-bromo-octane
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With bromine 1.) toluene, 85 deg C, 18 h 12.) CH2Cl2, 0 deg C; Yield given. Multistep reaction;
thiophene
188290-36-0

thiophene

1-bromo-octane
111-83-1

1-bromo-octane

2-octylthiophene
880-36-4

2-octylthiophene

Conditions
ConditionsYield
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 0.25h; Inert atmosphere;
Stage #2: 1-bromo-octane In tetrahydrofuran; hexane at -80 - 20℃;
Stage #3: With water In tetrahydrofuran; hexane
100%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: 1-bromo-octane In tetrahydrofuran; hexane at -78 - 20℃;
95%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
Stage #2: 1-bromo-octane In tetrahydrofuran; hexane for 4h; Inert atmosphere; Reflux;
84.6%
1-bromo-octane
111-83-1

1-bromo-octane

potassium thioacyanate
333-20-0

potassium thioacyanate

octyl thiocyanate
19942-78-0

octyl thiocyanate

Conditions
ConditionsYield
C(CH2S(=O)C6H13)4 at 100℃; for 0.5h;100%
With silica gel at 80℃; for 8h;97%
With 2-methylsulfinylpyridine In xylene at 100℃; for 40h;96%
1-bromo-octane
111-83-1

1-bromo-octane

sodium phenoxide
139-02-6

sodium phenoxide

octyloxybenzene
1818-07-1

octyloxybenzene

Conditions
ConditionsYield
poly<1-hydroxyethylene-co-1-(2-ethylsulf In 1,4-dioxane at 75℃; for 23h; Product distribution; Rate constant; other catalysts;100%
Sucrose-ethyleneoxide adducts In toluene at 110℃; for 8h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis;100%
dodecyldimethylsulfonium methyl sulfate In water at 40℃; for 6h;25%
1-bromo-octane
111-83-1

1-bromo-octane

potassium cyanide
151-50-8

potassium cyanide

nonanonitrile
2243-27-8

nonanonitrile

Conditions
ConditionsYield
Sucrose-ethyleneoxide adducts In acetonitrile at 83℃; for 24h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O;100%
tetraoctyl ammonium bromide In water; toluene at 90℃; for 24h; Product distribution; other phase-transfer catalysts, time;99%
tetraoctyl ammonium bromide In water; toluene at 90℃; for 24h;99%
1-bromo-octane
111-83-1

1-bromo-octane

1-Iodooctane
629-27-6

1-Iodooctane

Conditions
ConditionsYield
With potassium iodide; Sucrose-ethyleneoxide adducts In toluene at 110℃; for 24h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O;100%
With potassium iodide; polymeric crown ethers In water; toluene at 79.9℃; for 5h; Product distribution; catalysts with other crown-ether groups; or NaI, other reaction times;98%
With potassium iodide; tetraoctyl ammonium bromide In water; toluene at 90℃; for 24h;97%
1-bromo-octane
111-83-1

1-bromo-octane

1-azidooctane
7438-05-3

1-azidooctane

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 12h;100%
With sodium azide In water; acetone Reflux;100%
With sodium azide In methanol at 20℃; for 24h;100%
1-bromo-octane
111-83-1

1-bromo-octane

triphenylphosphine
603-35-0

triphenylphosphine

n-octyltriphenylphosphoniumbromide
42036-78-2

n-octyltriphenylphosphoniumbromide

Conditions
ConditionsYield
In chlorobenzene for 48h; Heating;100%
In toluene Reflux;100%
In o-xylene Heating;98.7%
S,S-dimethyl dithiocarbonate
868-84-8

S,S-dimethyl dithiocarbonate

1-bromo-octane
111-83-1

1-bromo-octane

methyl octyl sulfide
3698-95-1

methyl octyl sulfide

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;100%
4-bromo-phenol
106-41-2

4-bromo-phenol

1-bromo-octane
111-83-1

1-bromo-octane

1-bromo-4-octyloxybenzene
96693-05-9

1-bromo-4-octyloxybenzene

Conditions
ConditionsYield
With potassium carbonate Williamson's etherification;100%
With potassium carbonate In acetone for 43h; Heating;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere;96%
1-bromo-octane
111-83-1

1-bromo-octane

S,S-diethyl dithiocarbonate
623-80-3

S,S-diethyl dithiocarbonate

ethyl octyl sulfide
3698-94-0

ethyl octyl sulfide

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide for 0.5h; Heating;100%
1-bromo-octane
111-83-1

1-bromo-octane

S,S'-di-n-butyl dithiocarbonate
55716-09-1

S,S'-di-n-butyl dithiocarbonate

1-butyl 1-octyl sulphide
16900-07-5

1-butyl 1-octyl sulphide

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide for 1.5h; Heating;100%
1-bromo-octane
111-83-1

1-bromo-octane

S,S-dioctyl dithiocarbonate
69422-58-8

S,S-dioctyl dithiocarbonate

di-n-octyl sulfide
2690-08-6

di-n-octyl sulfide

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide for 3h; Heating;100%
1-bromo-octane
111-83-1

1-bromo-octane

potassium acetate
127-08-2

potassium acetate

n-octyl acetate
112-14-1

n-octyl acetate

Conditions
ConditionsYield
Sucrose-ethyleneoxide adducts In acetonitrile at 83℃; for 24h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O;100%
With aluminum oxide at 196℃; for 0.0333333h; Irradiation; other long chain halides;99%
With aluminum oxide at 196℃; for 0.0333333h; Irradiation;99%
1-bromo-octane
111-83-1

1-bromo-octane

sodium trithiocarbonate
534-18-9

sodium trithiocarbonate

dioctyl trithiocarbonate
89622-57-1

dioctyl trithiocarbonate

Conditions
ConditionsYield
Aliquat 336 at 70℃; for 1.5h;100%
1-bromo-octane
111-83-1

1-bromo-octane

3-(4-hydroxy-2-nitrophenyl)pyridine
119289-79-1

3-(4-hydroxy-2-nitrophenyl)pyridine

3-(2-nitro-4-n-octyloxyphenyl)pyridine
158461-43-9

3-(2-nitro-4-n-octyloxyphenyl)pyridine

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 1h;100%
1-bromo-octane
111-83-1

1-bromo-octane

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

3-(n-Octyloxy)benzaldehyde
24083-12-3

3-(n-Octyloxy)benzaldehyde

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;100%
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h;90%
1-bromo-octane
111-83-1

1-bromo-octane

1-indene
95-13-6

1-indene

3-octylindene
43130-63-8

3-octylindene

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 0.5h; Irradiation;100%
1-bromo-octane
111-83-1

1-bromo-octane

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

4-octylamino-benzoic acid ethyl ester
55791-74-7

4-octylamino-benzoic acid ethyl ester

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 125℃; for 10h; Addition;100%
In N,N,N,N,N,N-hexamethylphosphoric triamide at 125℃; for 24h;65%
1-bromo-octane
111-83-1

1-bromo-octane

methyl iodide
74-88-4

methyl iodide

1-methoxyoctane
929-56-6

1-methoxyoctane

Conditions
ConditionsYield
With aluminum oxide; potassium fluoride; potassium hydroxide In acetonitrile at 20℃; for 2h; Product distribution; effect of various catalyst and solvents;100%
With potassium hydroxide; Aliquat 336 at 20℃; for 2h;100%
1-bromo-octane
111-83-1

1-bromo-octane

diphenyl-phosphinic acid
1707-03-5

diphenyl-phosphinic acid

octyl phenyl(phenyl)phosphinate
3389-73-9

octyl phenyl(phenyl)phosphinate

Conditions
ConditionsYield
With potassium carbonate at 140℃; for 10h;100%
With caesium carbonate In acetonitrile at 100℃; for 12h; Inert atmosphere;93%
1-bromo-octane
111-83-1

1-bromo-octane

5,17,29-tri-tert-butyl-37,39,41-trihydroxy-38,40,42-trimethoxycalix[6]arene
156747-01-2

5,17,29-tri-tert-butyl-37,39,41-trihydroxy-38,40,42-trimethoxycalix[6]arene

5,17,29-tris(1,1-dimethylethyl)-37,39,41-trimethoxy-38,40,42-tris-(n-octyloxy)calix[6]carene

5,17,29-tris(1,1-dimethylethyl)-37,39,41-trimethoxy-38,40,42-tris-(n-octyloxy)calix[6]carene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;100%
picoline
108-89-4

picoline

1-bromo-octane
111-83-1

1-bromo-octane

1-(n-octyl)-4-methylpyridinium bromide

1-(n-octyl)-4-methylpyridinium bromide

Conditions
ConditionsYield
Darkness;100%
Darkness;100%
In acetonitrile at 70℃;97%
1-bromo-octane
111-83-1

1-bromo-octane

1-carbomethoxy-3,5-dihydroxybenzene
2150-44-9

1-carbomethoxy-3,5-dihydroxybenzene

methyl 3,5-bis(octyloxy)benzoate
87963-84-6

methyl 3,5-bis(octyloxy)benzoate

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetone for 60h; Etherification; Heating;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;98%
With adogen 464; potassium carbonate In acetone Heating;96%
1-bromo-octane
111-83-1

1-bromo-octane

methyl salicylate
119-36-8

methyl salicylate

2-octyloxybenzoic acid methyl ester
255062-85-2

2-octyloxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In methanol; N,N-dimethyl-formamide at 100℃; for 72h;100%
With potassium carbonate In acetonitrile at 85℃; Sealed tube; Inert atmosphere;100%
With sodium methylate In methanol for 48h; Alkylation; Heating;79%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h;71%
With sodium hydroxide In acetonitrile at 20℃; for 24h; Reagent/catalyst;76 g
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-bromo-octane
111-83-1

1-bromo-octane

1-octyl-3-methyl-imidazolium bromide

1-octyl-3-methyl-imidazolium bromide

Conditions
ConditionsYield
In neat (no solvent) at 60℃; for 24h; Inert atmosphere;100%
In neat (no solvent) for 5h; Sonication; Reflux;98%
at 80℃; for 72h;97%
1-bromo-octane
111-83-1

1-bromo-octane

4-(dimethylamino)-1-octylpyridinium bromide

4-(dimethylamino)-1-octylpyridinium bromide

Conditions
ConditionsYield
In acetonitrile for 15h; Heating;100%
In acetone for 9h; Heating;50%
In ethyl acetate at 70℃; for 48h;
1-bromo-octane
111-83-1

1-bromo-octane

3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

2-undecynyltetrahydro-2H-pyran-2-yl ether
88517-99-1

2-undecynyltetrahydro-2H-pyran-2-yl ether

Conditions
ConditionsYield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃;
Stage #2: 1-bromo-octane In tetrahydrofuran
100%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20℃; for 15h;
Stage #2: 1-bromo-octane In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20℃; for 29h;
82%
With n-butyllithium In tetrahydrofuran
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere;
Stage #2: 1-bromo-octane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 20℃; Inert atmosphere;
1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

1-bromo-octane
111-83-1

1-bromo-octane

1‐octyl‐1,4‐diazabicyclo[2.2.2]octan‐1‐ium bromide

1‐octyl‐1,4‐diazabicyclo[2.2.2]octan‐1‐ium bromide

Conditions
ConditionsYield
In dichloromethane for 12h; Reflux;100%
In tetrahydrofuran at 60℃; for 24h;95%
In ethyl acetate at 20℃; for 24h;91%
1-bromo-octane
111-83-1

1-bromo-octane

9H-carbazole
86-74-8

9H-carbazole

9-octylcarbazole
4041-19-4

9-octylcarbazole

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 120℃;100%
With sodium hydroxide; triethylamine hydrochloride In water; dimethyl sulfoxide at 80℃; for 8h;97.4%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 24h; Inert atmosphere; Reflux;96%
3,6-dibromo-9H-carbazole
6825-20-3

3,6-dibromo-9H-carbazole

1-bromo-octane
111-83-1

1-bromo-octane

3,6-dibromo-9-octyl-9H-carbazole
79554-93-1

3,6-dibromo-9-octyl-9H-carbazole

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 120℃;100%
With tetrabutylammomium bromide; potassium hydroxide In acetone for 6h; Reflux;95%
With tetrabutylammomium bromide; potassium hydroxide In water; toluene for 24h; Heating;95%

111-83-1Related news

Short CommunicationCatalytic reduction of 1-Bromooctane (cas 111-83-1) by nickel(I) salen electrogenerated at a mercury cathode in dimethylformamide08/21/2019

Cyclic voltammetry, controlled-potential electrolysis, and double-potential-step chronocoulometry have been used to characterize the catalytic reduction of 1-bromooctane by nickel(I) salen electrogenerated at a mercury cathode in dimethylformamide containing tetramethylammonium tetrafluoroborate...detailed

111-83-1Relevant articles and documents

Influence of Spacer Chains and Percentage Ring Substitution on Phase-transfer Catalytic Activity of Phosphonium Salts Bonded to Polystyrene Matrix

Anelli, Pier Lucio,Montanari, Fernando,Quici, Silvio

, p. 1827 - 1830 (1983)

In nucleophilic aliphatic substitutions carried out under liquid-liquid phase-transfer conditions, the catalytic activity of tributylphosphonium groups directly bonded to a polystyrene matrix through a methylene bridge decreases by about one order of magnitude on passing from 10 to 69percent ring substitution; log kobs. is linearly related to the loading of the catalytic sites.When tributylphosphonium groups are bonded to the polymer matrix by a linear spacer chain of 13 atoms for 10-30percent ring substitution, kobs. increases 1.7-3.1 times with respect to directly bonded catalysts.However, for spaced catalysts with 60percent ring substitution, the observed rate increase is 4.1-10-fold.This behaviour is explained by the combination of two opposing effects: (i) a polarity increase at the catalytic site by increasing percentage ring substitution leading to a decrease of nucleophilic activity of the anions; (ii)a polarity decrease at the catalytic site by insertion of spacer chains, due to the intrinsic lipophilicity of the alkyl chains as well as the more even distribution of catalytic sites within the polymer matrix.The reactivities of the catalysts, all prepared from chloromethylated polystyrene (200-400 mesh), are independent of the size of particles separated by sieves.

-

Landini,Montanari

, p. 879 (1974)

-

Silicon polypodands: A new class of efficient solid-liquid phase-transfer catalysts

Maia, Angelamaria,Landini, Dario,Leska, Boguslawa,Schroeder, Grzegorz

, p. 10111 - 10115 (2004)

Silicon polypodands 1-7 were found to be powerful complexing agents of alkali metal salts, even in low polarity media (chlorobenzene) and hence very efficient phase-transfer catalysts. Their catalytic activity was measured in typical anion-promoted reactions under solid-liquid phase-transfer catalysis (SL-PTC) conditions. It is mainly determined by the complexing ability of the ligand, increasing with the number of silicon atoms and binding sites. Comparison with traditional phase-transfer catalysts showed that these polypodands are better catalysts not only than open-chain PEG400Me2 and TRIDENT, but even than more sophisticated macrocyclic polyethers such as DCH18C6.

Novel Synthesis of Long-Chain Primary Alkyl Compounds

Gibson, Thomas,Tulich, Linda

, p. 1821 - 1823 (1981)

A method has been developed for the efficient laboratory-scale synthesis of long-chain compounds involving the metathesis of α-olefins to long-chain internal olefins, followed by hydrozirconation.The latter process gives the terminally substituted zirconium alkyl exclusively, which can be converted to a wide variety of functional groups.This paper deals exclusively with the formation of long-chain primary iodides.

Phase-Transfer Reactions Catalyzed by Lipophilic Cryptands and Dicyclohexano-18-crown-6: Dehydrating Effect of Concentrated Aqueous Alkaline Solutions

Landini, Dario,Maia, Angelamaria,Montanari, Fernando

, p. 2917 - 2923 (1984)

A study of how the concentration of aqueous KOH affects the hydration and hence the reactivity of anions (Cl-, Br-, I-, SCN-, N3-) in aliphatic nucleophilic substitutions catalyzed by lipophilic cryptand (1a) and dicyclohexano-18-crown-6 (DCH18C6) (2) under phase-transfer conditions is reported.A comparison with the same reactions performed in classical liquid-liquid PTC and homogeneous anhydrous conditions is also included.Unlike quaternary onium salts, even at the highest KOH concentrations (53percent; ie., conditions in which aH2O ca. 0), water in the presence of 1a is not completely removed.Residual hydration depends on the nature of the anion and is the highest for anions with localized and/or less polarizable charge, such as Cl-, Br-, and N3-.As a consequence, rate constants noticeably increase in comparison with those found under conventional PTC conditions but do not reach those of anhydrous solutions.The different behavior of cryptates and quaternary salts is discussed on the basis of the different topology of the two systems.Behavior of crown ethers is in between that of quaternary salts and cryptates, since residual hydration in the presence of 53percent aqueous KOH is lower than that of cryptates, whereas anionic reactivity becomes practically identical with that found under anhydrous conditions.

Synthesis of isoprenoid chain-contained chemical probes for an investigation of molecular interactions by using quartz crystal microbalance

Liu, Wujun,Zhang, Yixin,Hou, Shuhua,Zhao, Zongbao Kent

, p. 6208 - 6210 (2013)

Five probes including four that contained isoprenoid chain were synthesized. These probes were assembled onto the gold-coated quartz crystal chips for analysis of their interactions with four yeast proteins by using the quartz crystal microbalance technology. Results showed that 3-phosphoglycerate phosphokinase and triosephosphate isomerase had clear interactions with certain probes, while glutathione reductase and phosphoglucose isomerase gave much lower interaction signals. It also suggested that 3-phosphoglycerate phosphokinase had two sites interacting with the probe attached with a geranyl moiety. Further molecule simulation experiments provided supportive information on these intermolecular interactions. Together, our data suggested that there are hydrophobic interactions, with relatively good selectivity, between isoprenoid chain and proteins.

Crown ethers as phase-transfer catalysts. A comparison of an ionic activation in aqueous-organic two-phase systems and in low polarity anhydrous solutions by perhydrodibenzo-18-crown-6, lipophilic quaternary salts, cryptands

Landini, Dario,Maia, Angelamaria,Montanari, Fernando,Pirisi, Filippo M.

, p. 46 - 51 (1980)

Anion-promoted nucleophilic substitutions carried out in aqueous-organic two-phase systems in the presence of catalytic amounts of perhydrodibenzo-18- crown-6 follow the classic mechanism of phase-transfer catalysis. The observed pseudo-first-order rate constants are linearly related to the concentration of complexed crown ether in the organic phase. The narrow reactivity range and the sequence found in the reaction between n-octyl methane-sulphonate and a homogeneous series of anions in the PhCl-H2O two-phase system (N 3- > I- ~ Br- > CN - > Cl- > SCN-) remain largely unaltered in anhydrous PhCl. From this point of view complexed crown ethers differ substantially from lipophilic quaternary salts and cryptates. Indeed, removal of the hydration sphere of the anions in going from two-phase to anhydrous conditions is balanced by a larger cation-anion interaction, resulting in a very small variation of anion reactivity. This indicates that, unlike cryptates, complexed crown ethers can hardly be considered as a source of 'naked anions.' A comparison is also reported among lipophilic crown ethers, quaternary salts, and cryptands as phase-transfer catalysts.

Laudini et al.

, p. 112 (1977)

-

Kamm,Marvel

, (1920)

-

A synthesis of (±) methyl n tetradeca trans 2,4,5 trienoate, an allenic ester produced by the male dried bean beetle Acanthoscelides obtectus (Say)

Kocienski,Cernigliaro,Feldstein

, p. 353 - 355 (1977)

-

A new type of B-podand catalysts for solid-liquid phase transfer reactions

?eska, Bogus?awa,Pankiewicz, Rados?aw,Schroeder, Grzegorz,Maia, Angelamaria

, p. 5673 - 5676 (2006)

Boron podands 1-4 (B-podands) were studied as strong complexing agents of alkali metal cations and very powerful catalysts in typical anion promoted reactions under solid-liquid conditions, even in chlorobenzene and acetonitrile. The results were comparable with the catalytic activity of classical phase transfer catalysts: crown ethers, polyethylene glycols (PEG) and previously studied Si-podands.

Silicon polypodands: Powerful metal cation complexing agents and solid-liquid phase-transfer catalysts of new generation

Maia, Angelamaria,Landini, Dario,Leska, Boguslawa,Schroeder, Grzegorz

, p. 4149 - 4151 (2003)

Silicon polypodands 5-7 are found to be powerful complexing agents of alkali metal salts in low polarity solvents and very efficient catalysts in anion-promoted reactions under solid-liquid PTC conditions. The catalytic activity is comparable with that of the cyclic polyether PHDB18C6 8.

Method for continuously synthesizing bromo-n-octane in micro-reactor

-

Paragraph 0017-0037, (2020/01/14)

The invention discloses a method for continuously synthesizing bromo-n-octane in a micro-reactor. According to the method, n-octyl alcohol is used as a raw material, hydrobromic acid is used as a bromination reagent, and concentrated sulfuric acid is used as a catalyst to synthesize 1-bromo-n-octane in a microreactor. Because the width and depth of micro-channels in the reactor are small and rangefrom dozens of microns to hundreds of microns, the diffusion distance among reactants is greatly shortened, the mass transfer speed is high, and the reactants can be fully mixed and reacted in a short time in the flowing process. According to the method, microreactor technology is introduced into synthesis of bromo-n-octane, n-octyl alcohol is used as an initial raw material, hydrobromic acid isused as a bromination reagent, and concentrated sulfuric acid is used as a catalyst, so that continuous preparation of 1-bromo-n-octane is realized, the reaction operation is simple, the selectivity and yield of the product are relatively high, and the method has a wide industrial development prospect.

Synthesis of Branched Biolubricant Base Oil from Oleic Acid

Chen, Shuang,Wu, Tingting,Zhao, Chen

, p. 5516 - 5522 (2020/09/07)

The mature manufacturing of synthetic lubricants (poly-α-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.

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