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

Uses

Used in Antimicrobial Applications:
Hexadecyl trimethyl ammonium bromide is used as an anti-infectant agent for preventing the proliferation of bacteria, fungi, and yeast. It is particularly effective in cosmetic preparations, where it also serves as an emulsifying agent.
Used in Chemical Synthesis:
In the field of chemical synthesis, Hexadecyl trimethyl ammonium bromide is used as a template in the synthesis of Mesoporous γ-Fe2O3, a type of nanomaterial with potential applications in various industries.
Used in Biotechnology:
Hexadecyl trimethyl ammonium bromide is used as a cationic detergent in the isolation of high molecular weight DNA. Its surfactant properties help in the separation and purification of DNA from other cellular components.
Used in Pharmaceutical Industry:
As a component of the topical antiseptic cetrimide, Hexadecyl trimethyl ammonium bromide is used in the pharmaceutical industry for its antimicrobial properties, providing a broad-spectrum of activity against various microorganisms.
Used in Analytical Chemistry:
In analytical chemistry, Hexadecyl trimethyl ammonium bromide is used as a titrant for the potentiometric titration of perchlorate with ion-selective electrodes, allowing for accurate and precise measurements in various applications.

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

• 112-82-3 hexadecanyl bromide 
• 75-50-3 trimethylamine 
• 3508-00-7 1-bromoheptadecane 
• 629-93-6 n-iodooctadecane 
• 872-05-9 1-Decene 
• 5557-31-3 9-octadecene 
• 112-88-9 octadec-1-ene 
• 629-89-0 1-octadecyne 
• 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

• 72-55-9 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene 
• 505-86-2 cetyltrimethylammonium hydroxide 
• 76-82-4 (4-Amino-3-methyl-phenyl)-bis-(4-amino-phenyl)-methanol 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 16909-78-7 2-hydroxy-4-(2'-hydroxyethoxy)benzophenone 
• 25912-16-7 3-(1-pyrrolidinyl)phenol 
• 2610-16-4 cetyltrimethylammonium picrate 
• 112-82-3 hexadecanyl bromide 
• 75-50-3 trimethylamine 
• 7787-57-7 bismuth oxobromide 
• 124-23-2 hexadecyltrimethylammonium stearate 
• 138-32-9 hexadecyltrimethylammonium p-toluenesulfonate 
• 1354726-01-4 hexadecyltrimethylammonium (+/-)-2-(4-chloro-2-methylphenoxy)propionate 
• 210884-05-2 C₁₈H₁₄NO₃^(1-)*C₁₉H₄₂N⁽¹⁺⁾ 

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Method for activating denatured protein

A method for activating a denatured protein, includes the steps of: adding a detergent to the denatured protein to allow a protein-detergent complex to be formed; and adding high-molecular weight amylose to the protein-detergent complex so that the high-molecular weight amylose removes the detergent.

Ion-exchange resins, their preparation and uses

An ion-exchange resin stabilized against shrinkage, the resin being loaded with at least one amphiphilic ion in the absence of sodium cations. Also a process for removing iodide compounds from a liquid carboxylic acid and/or carboxylic acid anhydride obtained from the Group VIII noble metal catalysed, alkyl iodide co-catalysed carbonylation of alcohols and/or their reactive derivatives by contacting the liquid carboxylic acid and/or carboxylic acid anhydride with the ion-exchange resin stabilized against shrinkage as aforesaid, the ion-exchange resin being loaded with one or more of the metals silver, palladium or mercury.

Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth

The present invention discloses compositions containing lecithin and/or bactericidal compounds, and hydrophobic materials which form, upon application to dental surfaces, adhesive, protective and bacteria-inhibiting barriers.

Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth

The present invention discloses compositions containing a transfer agent and/or bactericidal compounds, and hydrophobic materials which form, upon application to dental surfaces, adhesive, protective and bacteria-inhibiting barriers.

Method for virus inactivation in the presence of polyalkylene glycol as well as the pharmaceutical preparation obtained therewith

The invention relates to a pharmaceutical preparation comprising a plasma protein wherein said preparation is free of infectious agents as well as essentially free of denaturation products and is obtainable by a method that encompasses the following steps: a) addition of a polyether and a chaotropic agent to a solution comprising the plasma protein, optional lyophilization of the solution; b) inactivation of infectious agents in the presence of the polyether by a physio-chemical or chemical treatment, and c) removal of the polyether and the chaotropic agent.