112-89-0

Basic information

• Product Name: 1-Bromooctadecane
• Synonyms: 1-BROMOOCTADECANE;STEARYL BROMIDE;OCTADECYL BROMIDE;N-OCTADECYL BROMIDE;1-bromo-octadecan;octadecane,1-bromo-;1-Bromooctodecane;N-OCTADECYL BROMIDE (STEARYL)
• CAS NO: 112-89-0
• Molecular Formula: C₁₈H₃₇Br
• Molecular Weight: 333.39
• EINECS: 204-013-4
• Product Categories: Alkyl Bromides;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes
• Mol File: 112-89-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 25-30 °C(lit.)
• Boiling Point: 214-216 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow/Low Melting Solid
• Density: 0.976 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.4E-05mmHg at 25°C
• Refractive Index: 1.462-1.464
• Storage Temp.: 2-8°C
• Water Solubility: insoluble
• BRN: 774145
• CAS DataBase Reference: 1-Bromooctadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromooctadecane(112-89-0)
• EPA Substance Registry System: 1-Bromooctadecane(112-89-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 112-89-0(Hazardous Substances Data)

Usage

Chemical Properties

colorless or light yellow liquid. soluble in ethanol, ether, ethyl acetate and petroleum ether, insoluble in water. Decomposes when exposed to light. It is used in organic synthesis.

Uses

1-Bromooctadecane is used in the preparation of shortened single-walled carbon nanotubes (s-SWCNTs). It is utilized to prepare octadecane in the presence of sodium borohydride as a catalyst. It is involved as a raw material for the preparation of dimethyldistearylammonium bromide, which is a bentonite modifier.

Preparation

1-Bromooctadecane is synthesized by the reaction of stearyl alcohol with hydrogen bromide. The alcohol is heated to 100°C, dry hydrogen bromide is introduced, and the reaction temperature is maintained at 100-120°C until the solution no longer absorbs hydrogen bromide. The bromide is layered, the organic phase is washed with concentrated sulfuric acid, the bromide after the acid solution is separated and mixed with an equal volume of 90% methanol, washed with ammonia to make the bromide alkaline, then washed with 90% methanol, and anhydrous Dry calcium chloride. Finally, vacuum distillation, collecting 209-211 ℃ (1.33kPa) fraction is 1-bromooctadecane, and the yield is 90%.

Purification Methods

Twice recrystallise bromooctadecane from the melt, then distil it under vacuum three times using the middle cut. Alternatively, wash the oil with aqueous Na2SO4, then conc H2SO4 (cool) and again with aqueous Na2SO4 and then fractionally distil it. [Meyer & Ried J Am Chem Soc 55 1574 1933, Hoffmann & Smyth J Am Chem Soc 72 171 1950, IR: LeFévre et al. Aust J Chem 12 743 1959, IR: Brini-Fritz Bull Soc Chim Fr 516 1957, Beilstein 1 IV 555.]

InChI:InChI=1/C18H37Br/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-18H2,1H3

Synthetic route

1-octadecanol (112-92-5) + 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (20244-61-5) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With triphenylphosphine In dichloromethane for 4h; Ambient temperature;	99%

1-(tert-butyldimethylsilyloxy)octadecan (65598-00-7) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; triphenylphosphine; calcium carbonate In 1,2-dichloro-ethane for 3.5h; Ambient temperature;	99%

2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (20244-61-5) + 2-(octadecyloxy)tetrahydro-2H-pyran (66938-10-1) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With triphenylphosphine In dichloromethane for 2h; Ambient temperature;	98%

1-octadecanol (112-92-5) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃;	97%
With Amberlite IRA 93 (PBr3 form) In diethyl ether for 6h; Ambient temperature;	96%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃;	96%

1-octadecanol, trimethylsilyl ether (18748-98-6) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; triphenylphosphine; calcium carbonate In tetrahydrofuran; acetonitrile for 3h; Ambient temperature;	97%

Triethyl-octadecyloxy-silane (65598-06-3) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; triphenylphosphine; calcium carbonate In tetrahydrofuran; acetonitrile for 2h; Ambient temperature;	92%

thiocarbonic acid O-(4-chloro-phenyl) ester O-octadecyl ester (62008-64-4) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With bromine

trifluoroacetate 1-octadecanol (79392-43-1) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With lithium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 3h; Heating; Yield given;

mercury (II)-salt of/the/ nonadecanoic acid → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With tetrachloromethane; bromine

1-octadecyl methanesulfonate (31081-59-1) → 1-Bromooctadecane (112-89-0)

Conditions	Yield
With sodium bromide

1-octadecanol (112-92-5) + alkali alkylate → 1-Bromooctadecane (112-89-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.25 h / Ambient temperature 2: LiBr / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / Heating View Scheme

N-palmitoyl-(L)-cysteine (67603-49-0) → 1-Bromooctadecane (112-89-0)

2,2'-iminobis[ethanol] (111-42-2) + 1-Bromooctadecane (112-89-0) → N,N-diethanolstearylamine (10213-78-2)

Conditions	Yield
In acetonitrile Heating;	100%
With potassium carbonate; potassium iodide In acetonitrile	100%
With potassium hydrogencarbonate; potassium iodide In acetonitrile for 3h; Heating / reflux;	100%
With 2-pentanol das Hydrobromid ensteht;

sodium trithiocarbonate (534-18-9) + 1-Bromooctadecane (112-89-0) → trithiocarbonic acid dioctadecyl ester

Conditions	Yield
Aliquat 336 at 70℃; for 3h;	100%

1-Bromooctadecane (112-89-0) + 2-hydroxynitrobenzene (88-75-5) → 1-nitro-2-octadecyloxy-benzene (86996-83-0)

Conditions	Yield
With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 20 - 80℃; Inert atmosphere;	100%
With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 20 - 80℃; Inert atmosphere;	100%
With sodium hydride In N,N-dimethyl-formamide 1.) 0 deg C, 1 h, 2.) reflux, 24 h;	60%
With potassium carbonate In acetone

methyl galloate (99-24-1) + 1-Bromooctadecane (112-89-0) → methyl [3,4,5-tris(n-octadecan-1-yloxy)]benzoate (188685-33-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;	100%
With potassium carbonate In dimethyl sulfoxide; toluene at 60℃; for 24h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;	98%

Methyl thioglycolate (2365-48-2) + 1-Bromooctadecane (112-89-0) → methyl 2-(octadecylthio)acetate (130614-27-6)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide; acetone at 20℃; for 48h;	100%
With potassium carbonate In dimethyl sulfoxide; acetone at 20℃; for 24h; Alkylation;	90%

2-chloro-3-hydroxypyridine (6636-78-8) + 1-Bromooctadecane (112-89-0) → 2-chloro-3-octadecyloxy-pyridine (905599-19-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 8h;	100%

(6-methoxyquinolin-4-yl)((1S,4S,5R)-5-vinylquinuclidin-2-yl)methanol (56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2) + 1-Bromooctadecane (112-89-0) → C38H61N2O2(1+)

Conditions	Yield
In acetonitrile for 24h; Heating;	100%

N,N-bis[3-(dimethylamino)propyl]-N',N'-dimethylpropane-1,3-diamine (33329-35-0) + 1-Bromooctadecane (112-89-0) → C69H147N4(3+)*3Br(1-)

Conditions	Yield
In acetonitrile for 24h; Reflux;	100%

1-Bromooctadecane (112-89-0) + Quinine (130-95-0) → C38H61N2O2(1+)*Br(1-)

Conditions	Yield
In acetonitrile for 26h; Reflux;	100%

1-methyl-1,3-dihydro-imidazole-2-thione (60-56-0) + 1-Bromooctadecane (112-89-0) → 1-Methyl-2-octadecylsulfanyl-1H-imidazole; hydrobromide (50968-67-7)

Conditions	Yield
In acetonitrile for 24h; Reflux;	100%

2-heptadecylimidazole (23328-87-2) + 1-Bromooctadecane (112-89-0) → 1-octadecyl-2-heptadecylimidazole

Conditions	Yield
With potassium hydroxide In toluene for 11h; Reflux;	99.4%

bis(2,5-dimethylpyrrolo)[3,4-d]tetrathiafulvalene (117860-14-7) + 1-Bromooctadecane (112-89-0) → 4,6,4',6'-Tetramethyl-5,5'-dioctadecyl-5H,5'H-[2,2']bi[[1,3]dithiolo[4,5-c]pyrrolylidene]

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1) room temperature, 5 min, 2) 20 min;	99%

1-Bromooctadecane (112-89-0) → n-octadecylphosphonic acid (4724-47-4)

Conditions	Yield
Stage #1: 1-Bromooctadecane With phosphoric acid; N,O-Bis(trimethylsilyl)trifluoroacetamide at 120℃; Stage #2: With water In methanol at 20℃; for 2h; Further stages.;	99%
Stage #1: 1-Bromooctadecane With potassium hydroxide semihydrate; phosphorus; cetyltrimethylammonim bromide In water; toluene at 70℃; for 6h; Inert atmosphere; Stage #2: With nitric acid In water at 100 - 110℃; for 2h; pH=4; Inert atmosphere;	20%
Multi-step reaction with 2 steps 1: hexane 2: concentrated aqueous HCl View Scheme
Multi-step reaction with 2 steps 1.1: 150 °C / Inert atmosphere; Schlenk technique 2.1: trimethylsilyl bromide / dichloromethane 2.2: 3 h View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide 2: trimethylsilyl bromide View Scheme

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-Bromooctadecane (112-89-0) → 1- octadecyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	99%
In acetonitrile at 20℃; for 24h;	88%
In acetone at 20 - 50℃; for 1.5h;	79%

1-methyl-1H-imidazole (616-47-7) + 1-Bromooctadecane (112-89-0) → 1-methyl-3-octadecyl-1H-imidazol-3-ium bromide (379231-56-8)

Conditions	Yield
In acetone at 85℃; for 15h; Schlenk technique; Inert atmosphere;	99%
In ethanol at 80℃; for 72h; Inert atmosphere;	84.2%
In tetrahydrofuran at 60℃; Schlenk technique;	22%

2-nitro-9H-fluorene (607-57-8) + 1-Bromooctadecane (112-89-0) → 2-nitro-9,9-di-(n-octadecyl)-9H-fluorene (1007602-87-0)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20 - 50℃;	99%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 1-Bromooctadecane (112-89-0) → C24H53N2(1+)*Br(1-) (171894-19-2)

Conditions	Yield
In acetone at 20℃; for 3h; Reflux;	99%
In acetone for 3h; Reflux;	99%
In methanol at 50℃; for 28h; Inert atmosphere;	91.5%

3-hydroxy-6-methylpicolinaldehyde (66497-42-5) + 1-Bromooctadecane (112-89-0) → 3-octadecyloxy-6-methylpicolinaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	99%

2-Formyl-3-hydroxypyridin (1849-55-4) + 1-Bromooctadecane (112-89-0) → 3-octadecyloxypicolinaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;	99%

9H-carbazole (86-74-8) + 1-Bromooctadecane (112-89-0) → 9-octadecyl-9H-carbazole

Conditions	Yield
With potassium hydroxide In acetone Reflux;	99%
With tetrabutylammomium bromide; sodium hydroxide
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;
With potassium hydroxide In N,N-dimethyl-formamide
With potassium hydroxide In N,N-dimethyl-formamide

methyl 3-aminopropanoate hydrochloride (3196-73-4) + 1-Bromooctadecane (112-89-0) → methyl N,N-dioctadecyl-3-aminopropanoate (943011-40-3)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 81℃; for 18h;	99%

ethyl orselinate (2524-37-0) + 1-Bromooctadecane (112-89-0) → ethyl 2-hydroxy-6-methyl-4-(octadecyloxy)benzoate

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone Reflux; Inert atmosphere;	99%

betaine (107-43-7) + 1-Bromooctadecane (112-89-0) → (2-octadecyloxy-2-oxoethyl)trimethylammonium bromide

Conditions	Yield
In acetonitrile at 80℃; for 72h;	99%
In acetonitrile at 80℃; Green chemistry;	88%

1-Bromooctadecane (112-89-0) + 2,4,6-tribromophenol (118-79-6) → 1,3,5-tribromo-2-octadecyloxybenzene (959685-14-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 17h;	98.5%

1-octadecyl-2-heptadecylimidazole + 1-Bromooctadecane (112-89-0) → 1,3-dioctadecyl-2-heptadecylimidazolium bromide

Conditions	Yield
at 120℃; for 4h;	98.2%

methyl 4-hydroxylbenzoate (99-76-3) + 1-Bromooctadecane (112-89-0) → methyl 4-(octadecyloxy)benzoate (40654-37-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere;	98%
With potassium carbonate In acetone for 24h; Heating;	94%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone Reflux; Inert atmosphere;	90%

4-cyanophenol (767-00-0) + 1-Bromooctadecane (112-89-0) → 4-(octadecyloxy)benzonitrile (139536-08-6)

Conditions	Yield
With potassium carbonate In acetone for 48h; Heating;	98%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 15h;	97%
With potassium carbonate In acetonitrile Reflux;	75%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h;	72%

rac-3-sulfanylpropane-1,2-diol (96-27-5) + 1-Bromooctadecane (112-89-0) → octadecylthio-1 propanediol-2,3 (7400-44-4)

Conditions	Yield
With potassium hydroxide In methanol for 48h; Ambient temperature;	98%
With potasse ethanolique In ethanol at 20℃; for 4h;	92%
With potassium hydroxide In hexane for 48h; Ambient temperature;

Upstream product

• 112-92-5 1-octadecanol 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 18748-98-6 1-octadecanol, trimethylsilyl ether 
• 67603-49-0 N-palmitoyl-(L)-cysteine 
• 31081-59-1 1-octadecyl methanesulfonate 
• 65598-00-7 1-(tert-butyldimethylsilyloxy)octadecan 
• 65598-06-3 Triethyl-octadecyloxy-silane 
• 66938-10-1 2-(octadecyloxy)tetrahydro-2H-pyran 
• 79392-43-1 trifluoroacetate 1-octadecanol 
• 62008-64-4 thiocarbonic acid O-(4-chloro-phenyl) ester O-octadecyl ester 

Downstream Products

• 40654-37-3 methyl 4-(octadecyloxy)benzoate 
• 3881-14-9 octadecyltriethylammonium bromide 
• 4445-06-1 octadecylcyclohexane 
• 123904-03-0 octacos-9-yne 
• 3700-67-2 dimethyldioctadecylammonium bromide 
• 62435-06-7 1-Ethoxy-octadecan 
• 765-27-5 icos-1-yne 
• 103167-74-4 (2,4-dichloro-phenyl)-octadecyl ether 
• 89290-68-6 1,3-bis-octadecyloxy-benzene 
• 16165-72-3 octadecylphosphonate de diethyle 
• 4445-07-2 octadecylbenzene 
• 630-06-8 hexatriacontane 
• 2500-88-1 dioctadecyl disulphide 
• 6140-87-0 octadecane-1-sulfonic acid 

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