57-09-0

Basic information

• Product Name: Hexadecyl trimethyl ammonium bromide
• Synonyms: N-CETYL-N,N,N-TRIMETHYLAMMONIUM BROMIDE;N,N,N-TRIMETHYLTETRADECYLAMMONIUM BROMIDE;N-HEXADECYL-N,N,N-TRIMETHYLAMMONIUM BROMIDE;N-HEXADECYLTRIMETHYLAMMONIUM BROMIDE;PALMITYLTRIMETHYLAMMONIUM BROMIDE;TIMTEC-BB SBB008910;TRIMETHYLHEXADECYL-AMMONIUM BROMIDE;1-Hexadecanaminium,N,N,N-trimethyl-,bromide
• CAS NO: 57-09-0
• Molecular Formula: Br*C₁₉H₄₂N
• Molecular Weight: 364.45
• EINECS: 200-311-3
• Product Categories: Organics;Ammonium Bromides (Quaternary);Biochemistry;Cationic Surfactants (for Biochemistry);Quaternary Ammonium Compounds;Surfactants (for Biochemistry);CETAB;Pharmaceutical raw materials
• Mol File: 57-09-0.mol
• Article Data: 37

Chemical Properties

• Melting Point: 248-251 °C(lit.)
• Flash Point: 244 °C
• Appearance: white/powder
• Density: 1.1107 (rough estimate)
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Store at RT.
• Solubility: H2O: 50 mg/mL
• Water Solubility: 13 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Protect from moisture.
• Merck: 14,2025
• BRN: 3598189
• CAS DataBase Reference: Hexadecyl trimethyl ammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Hexadecyl trimethyl ammonium bromide(57-09-0)
• EPA Substance Registry System: Hexadecyl trimethyl ammonium bromide(57-09-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-37/38-41-50-50/53-36/37/38-48/22
• Safety Statements: 26-39-61-37/39-60-36
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: BQ7875000
• F: 3
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 57-09-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder. Soluble in water, alcohol, and chloroform.

Uses

Different sources of media describe the Uses of 57-09-0 differently. You can refer to the following data:
1. antiinfectant
2. Hexadecyltrimethylammonium Bromide (CTAB) is a cationic surfactant used as a template in the synthesis of Mesoporous γ-Fe2O3.
3. A cationic detergent used in the isolation of high molecular weight DNA.
4. cetrimonium bromide is a quaternary ammonium salt that can prevent the proliferation of bacteria, fungi, and yeast in cosmetic preparation, while also act as an emulsifying agent.

Definition

ChEBI: The organic bromide salt that is the bromide salt of cetyltrimethylammonium; one of the components of the topical antiseptic cetrimide.

General Description

Hexadecyltrimethylammonium bromide is a titrant for the potentiometric titration of perchlorate with ionselective electrodes.

Biochem/physiol Actions

Hexadecyltrimethylammonium bromide also called cetyltrimethylammonium bromide (CTAB), is a cationic surfactant. CTAB is employed for extraction of DNA. CTAB method is efficient, cost and time effective for DNA extraction. CTAB is used as a shaping material and reducing agent for nanoparticle generation.

Purification Methods

Crystallise it from EtOH, EtOH/*benzene or from wet acetone after extracting twice with pet ether. Shake it with anhydrous diethyl ether, filter and dissolve it in a little hot MeOH. After cooling in the refrigerator, the precipitate is filtered off at room temperature and re-dissolved in MeOH. Anhydrous ether is added and, after warming to obtain a clear solution, it is cooled and the crystalline material is collected. [Dearden & Wooley J Phys Chem 91 2404 1987, Hakemi et al. J Am Chem Soc 91 120 1987, Beilstein 4 IV 819.]

InChI:InChI=1/C51H105N.BrH/c1-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49(4)52(50(5)47-44-41-38-35-32-29-26-23-20-17-14-11-8-2)51(6)48-45-42-39-36-33-30-27-24-21-18-15-12-9-3;/h49-51H,7-48H2,1-6H3;1H

Synthetic route

hexadecanyl bromide (112-82-3) + trimethylamine (75-50-3) → cetyltrimethylammonim bromide (57-09-0)

Conditions	Yield
With methanol
With ethanol
With ethanol at 115℃;

C19H42N(1+)*C10H7N4O9(1-) → 1,3,6,8-tetranitronaphthalene (28995-89-3) + cetyltrimethylammonim bromide (57-09-0)

Conditions	Yield
In 1,4-dioxane at 25℃; Equilibrium constant;

hexadecyltrimethylammonium cyanide (74784-26-2) → sodium cyanide (143-33-9) + cetyltrimethylammonim bromide (57-09-0)

Conditions	Yield
With sodium bromide In water at 20℃; Equilibrium constant;

4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium; (99023-50-4) → methyl orange (547-58-0) + cetyltrimethylammonim bromide (57-09-0)

Conditions	Yield
With sodium bromide at 19.9℃; Equilibrium constant; var. temps.;

ethyl bromide (74-96-4) + N,N-dimethylhexadecylamine (112-69-6) → cetyltrimethylammonim bromide (57-09-0)

2Br(1-)*C4H5N2(1-)*C19H42N(1+)*Zn(2+) → cetyltrimethylammonim bromide (57-09-0)

Conditions	Yield
In ethanol at 80℃; for 0.0833333h; Sonication;

cetyltrimethylammonim bromide (57-09-0) → cetyltrimethylammonium hydroxide (505-86-2)

Conditions	Yield
With Amberlyst A-26(OH-)form In methanol	100%
With Amberlite CG-400 resin
With Amberlite IRA-900 In methanol

trimethyl sulphoxonium + 4'-fluoro-2-(1H-1,2,4-triazol-1-yl)propiophenone hydrochloride + 1,1,1-trichloroethane (71-55-6) + cetyltrimethylammonim bromide (57-09-0) → 2-(4-fluorophenyl)-2-[1-(1H-1,2,4-triazol-1-yl)ethyl]oxirane

Conditions	Yield
With sodium hydroxide	99%

cetyltrimethylammonim bromide (57-09-0) → cetyltrimethylammonium tribromide

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; potassium bromide; molybdic acid In water at 0 - 20℃; for 0.916667 - 3.5h; Product distribution / selectivity;	98.86%

potassium dichromate + cetyltrimethylammonim bromide (57-09-0) → cetyl-trimethylammonium dichromate

Conditions	Yield
In H2O synthesized by treating K2Cr2O7 in aqueous solution of ammonium-compd.; isolated, washed with H2O, dried in vac., kept in a dark bottle inside adesiccator, elem. anal.;	98%

iron(III) chloride + cetyltrimethylammonim bromide (57-09-0) → cethyltrimethylammonium bromide

Conditions	Yield
In methanol at 20℃; for 12h; Inert atmosphere;	98%

cetyltrimethylammonim bromide (57-09-0) → cetyltrimethylammonium tribromide

Conditions	Yield
With bromine In water	97%
With dihydrogen peroxide; vanadia at 5℃; Yield given;

cetyltrimethylammonim bromide (57-09-0) → cetyl trimethylammonium tribromide (52752-51-9)

Conditions	Yield
With dihydrogen peroxide; sodium carbonate; potassium bromide In water at 20℃; for 0.0833333h;	96%
With 3-chloro-benzenecarboperoxoic acid; potassium bromide In water for 0.1h;	90%
With potassium peroxymonosulfate; sodium bromide In water for 1h;	90%

cetyltrimethylammonim bromide (57-09-0) → N,N,N-trimethylhexadecylammonium iodide (7192-88-3)

Conditions	Yield
With potassium iodide In water	95%

cetyltrimethylammonim bromide (57-09-0) → cetyltrimethylammonium peroxodisulphate

Conditions	Yield
With dipotassium peroxodisulfate In water	93%
With dipotassium peroxodisulfate In water at 20℃; for 0.333333h;	92%
With dipotassium peroxodisulfate In water

cetyltrimethylammonim bromide (57-09-0) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → N,N′,N′′,N′′′-hexadecyltrimethylammonium bis(trifluoromethylsulfonyl)imide (1031250-01-7)

Conditions	Yield
In water at 20℃; for 1h;	93%

potassium permanganate (7722-64-7) + cetyltrimethylammonim bromide (57-09-0) → cethyltrimethylammonium permanganate (73257-07-5)

Conditions	Yield
In H2O ammonium-compd. stirred with an equivalent amount of KMnO4 in H2O; separated, washed with H2O;	92%
In water pptn.; from lit. Int. J. Chem. Kinet. 27 (7) (1995) 627;
In water pptn. of an aq. soln. of cetyltrimethylammonium bromide with a satd. soln. of KMnO4; washed (cold water), dried for several hours under vac.;

potassium permanganate (7722-64-7) + sodium tungstate (VI) dihydrate (10213-10-2) + cetyltrimethylammonim bromide (57-09-0) + boric acid (11113-50-1) + manganese(II) acetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → 4C16H33(CH3)3N(1+)*2H(1+)*Mn(3+)*H2O*BW11O39(9-)*10H2O=[C16H33(CH3)3N]4H2[Mn(H2O)BW11O39]*10H2O

Conditions	Yield
In water; 1,2-dichloro-ethane Mn and W salts mixed in H2O, treated with H3BO3, treated dropwise with excess of hexadecyltrimethylammonium bromide in water with stirring at 80-85°C; washed(water), dried (vac.), elem. anal.;	92%

indigo 5,5'-disulfonic acid (483-20-5) + cetyltrimethylammonim bromide (57-09-0) → C16H8N2O8S2(2-)*2C19H42N(1+)

Conditions	Yield
In water at 80℃; for 2h;	92%

bismuth(III) nitrate + water (7732-18-5) + cetyltrimethylammonim bromide (57-09-0) + cetyltrimethylammonium chloride (112-02-7) → BiOCl0.8Br0.2

Conditions	Yield
With acetic acid at 20℃; for 0.5h;	91%

ammonium cerium (IV) nitrate (16774-21-3) + cetyltrimethylammonim bromide (57-09-0) → cetyltrimethylammonium cerium nitrate

Conditions	Yield
In H2O Ce-compd. in H2O added slowly to ammonium-compd. in H2O with continuous stirring, stirred for 30 min; filtered, washed with chilled H2O, dried in vac., kept in a dark bottle inside a desiccator, elem. anal.;	90%

potassium hexacyanoruthenate(II) + cetyltrimethylammonim bromide (57-09-0) → 4(CH3)3N(CH2)15CH3(1+)*Ru(CN)6(4-)=[(CH3)3N(CH2)15CH3]4[Ru(CN)6]

Conditions	Yield
In methanol pptn. on addn. of 4 equiv. ammonium salt to Ru-complex (stirring); water addn., stirring for 10 min, collection (filtration), washing (water, MeOH, ether), drying (vac.);	86%

potassium tetrachloroplatinate(II) (10025-99-7) + cetyltrimethylammonim bromide (57-09-0) → 2(CH3)3(C16H33)N(1+)*PtCl4(2-) = [(CH3)3(C16H33)N]2[PtCl4]

Conditions	Yield
In water at 20℃; for 6h;	86%

[1,3]-dioxolan-2-one (96-49-1) + 2,4-dihydroxybenzophenone (131-56-6) + cetyltrimethylammonim bromide (57-09-0) → 2-hydroxy-4-(2'-hydroxyethoxy)benzophenone (16909-78-7)

Conditions	Yield
In water	85%

1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) + neodymium trichloride (10024-93-8) → {C16H33(CH3)3N}(1+)*{NdO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NNdO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions

Yield

With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, lanthanide chloride is added, stirring for 2 h at room temp.; distilled water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;

85%

1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) + yttrium(III) chloride (10361-92-9) → {C16H33(CH3)3N}(1+)*{YO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NYO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions	Yield
With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, YCl3 is added, stirring for 2 h at room temp.; distilled water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;	85%

1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) + praseodymium(III) chloride (10361-79-2) → {C16H33(CH3)3N}(1+)*{PrO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NPrO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions

Yield

With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, lanthanide chloride is added, stirring for 2 h at room temp.; distilled water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;

85%

(RS)-2-(4-chloro-o-tolyloxy)propionic acid (93-65-2) + cetyltrimethylammonim bromide (57-09-0) → hexadecyltrimethylammonium (+/-)-2-(4-chloro-2-methylphenoxy)propionate (1354726-01-4)

Conditions	Yield
Stage #1: (RS)-2-(4-chloro-o-tolyloxy)propionic acid With sodium hydroxide In water at 49.84℃; Stage #2: cetyltrimethylammonim bromide In water for 2h;	85%

5,10-dihydroindeno[1,2-b]indole (3254-91-9) + cetyltrimethylammonim bromide (57-09-0) → 5-Methyl-5,10-dihydroindeno[1,2-b]indole (7428-85-5)

Conditions	Yield
With methyl iodide In sodium hydroxide; benzene	84%

1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) + lanthanum(III) chloride (10099-58-8) → {C16H33(CH3)3N}(1+)*{LaO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NLaO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions	Yield
With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, lanthanide chloride is added, stirring for 2 h at room temp.; distd. water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;	84%

dysprosium(III) trichloride (10025-74-8) + 1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) → {C16H33(CH3)3N}(1+)*{DyO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NDyO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions

Yield

With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, lanthanide chloride is added, stirring for 2 h at room temp.; distilled water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;

83%

1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) + gadolinium(III) chloride (10138-52-0) → {C16H33(CH3)3N}(1+)*{GdO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NGdO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions

Yield

With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, lanthanide chloride is added, stirring for 2 h at room temp.; distilled water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;

82%

1,5-bis-(1-phenyl-3-methyl-2-pyrazol-5-on-4-yl)-1,5-pentanedione (122835-10-3) + cetyltrimethylammonim bromide (57-09-0) + terbium(III) chloride (10042-88-3) → {C16H33(CH3)3N}(1+)*{TbO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4}(1-)=C16H33(CH3)3NTbO8(C6H5)4(CH3)4(CC3H6C)2(C3N2)4

Conditions

Yield

With NaOH In ethanol the pentadione-derivate and cetyltrimethyl ammonium bromide are dissolved in EtOH/NaOH and the pH of this soln. is adjusted to 8-9, lanthanide chloride is added, stirring for 2 h at room temp.; distilled water is added into the mother soln., the ppt. is centrifugally separated, the ppt. is washed with 50% EtOH and water, the product is dried at 50°C in a vac. dryer, elem. anal.;

82%

sodium molybdate dihydrate (7631-95-0) + cetyltrimethylammonim bromide (57-09-0) + oxalic acid dihydrate (6153-56-6) → C2MoO9(2-)*H2O*2C19H42N(1+)

Conditions	Yield
Stage #1: sodium molybdate dihydrate With sulfuric acid; dihydrogen peroxide In water pH=2; Stage #2: cetyltrimethylammonim bromide; oxalic acid dihydrate In water for 0.0833333h; pH=2; Cooling with ice;	82%

sodium molybdate dihydrate (7631-95-0) + dihydrogen peroxide (7722-84-1) + cetyltrimethylammonim bromide (57-09-0) + oxalic acid (144-62-7) → C2MoO9(2-)*2C19H42N(1+)

Conditions	Yield
Stage #1: sodium molybdate dihydrate; dihydrogen peroxide With sulfuric acid In water pH=2; Stage #2: cetyltrimethylammonim bromide; oxalic acid In water for 0.0833333h; pH=2; Cooling with ice;	82%

cetyltrimethylammonim bromide (57-09-0) → cetyltrimethylammonium hypochlorite (1346270-26-5)

Conditions	Yield
With sodium hypochlorite; chlorine In dichloromethane at 20℃;	81%

Upstream product

• 629-89-0 1-octadecyne 
• 3508-00-7 1-bromoheptadecane 
• 75-50-3 trimethylamine 
• 629-93-6 n-iodooctadecane 
• 872-05-9 1-Decene 
• 5557-31-3 9-octadecene 
• 112-88-9 octadec-1-ene 
• 112-82-3 hexadecanyl bromide 
• 114838-55-0 17-tetratriacontyne 
• 74-96-4 ethyl bromide 
• 112-69-6 N,N-dimethylhexadecylamine 
• 99023-50-4 4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium; 
• 74784-26-2 hexadecyltrimethylammonium cyanide 

Downstream Products

• 505-86-2 cetyltrimethylammonium hydroxide 
• 12582-61-5 μ-oxo-bis[α,β,γ,δ-tetraphenylporphinatoiron] 
• 7440-57-5 gold 
• 112-82-3 hexadecanyl bromide 
• 75-50-3 trimethylamine 
• 124-23-2 hexadecyltrimethylammonium stearate 
• 76-82-4 (4-Amino-3-methyl-phenyl)-bis-(4-amino-phenyl)-methanol 
• 467-63-0 crystal violet carbinol base 
• 630-98-8 brilliant green 
• 510-13-4 1,1-bis(4-dimethylaminophenyl)-1-phenyl-methanol 
• 38844-00-7 hexadecyltrimethylammonium dodecylsulfate 
• 100-42-5 styrene 
• 99023-50-4 4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium; 
• 74-83-9 methyl bromide 

Relevant articles and documents

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WAX COMPOSITIONS COMPRISING LINEAR OLEFIN DIMERS OR HODROGENATED VARIANTS THEREOF AND METHODS FOR PRODUCTION THEREOF

Wax compositions may be obtained by providing an olefinic feed comprising a first linear alpha olefin having m carbon atoms and a second linear alpha olefin having n carbon atoms, wherein m and n are independently selected integers each ranging from about 12 to about 100, and the olefinic feed optionally comprises one or more internal olefins and/or one or more branched olefins; contacting the olefinic feed with a metal carbene catalyst in a reactor; forming ethylene and a hydrocarbon substance comprising a linear olefin dimer comprising two carbon atoms less than a sum of m and n; removing the ethylene from the reactor while forming the linear olefin dimer; and isolating a wax composition comprising the linear olefin dimer, a hydrogenated reaction product thereof, or any combination thereof.

Odd-even effect and unusual behavior of dodecyl-substituted analogue observed in the crystal structure of alkyltrimethylammonium-[Ni(dmit) 2]- salts

A series of [Ni(dmit)2]- (dmit: 1,3-dithiole-2- thione-4,5-dithiolato) salts of alkyltrimethylammonium (Cn: n represents the alkyl chain length; n = 3 and 518) have been prepared and analyzed by X-ray structural analysis. All complex salts have been found to be composed of alternate sheets of [Ni(dmit)2]- anions and sheets of cations with a pronounced interdigitation of the alkyl chains. However, molecular arrangement differed between (C3)[Ni(dmit)2] and other (Cn)[Ni(dmit)2] (n = 518). Adjacent cations were aligned along the long axis of [Ni(dmit)2]- anion in C3 complex salt, while in others (C5-C18 complex salts), they were aligned toward the short axis. Such a difference in arrangement arose from correlativity between the lengths of the long axis of cation and anion, namely CLCA. Furthermore, relative orientation between the alkyl chain of cation and [Ni(dmit)2]- anion differed between the odd- and even-numbered cations for C10-C18. Whereas the plane of alkyl chain for odd-numbered cation was normal to the plane of [Ni(dmit)2]- anion, that of even-numbered cation was parallel. It was also found that C12 analog behaved like odd-numbered cations. However, in C12 salt, the end methyl group of the dodecyl group adopted unusual end-gauche conformation.