139-07-1

Basic information

• Product Name: 1227
• Synonyms: c12-alkylbenzyldimethylammonium chloride;DIMETHYLBENZYLLAURYLAMMONIUM CHLORIDE;DODECYL DIMETHYL BENZYL AMMONIUM CHLORIDE;BENZYLDODECYLDIMETHYLAMMONIUM CHLORIDE;BENZYLDIMETHYLDODECYLAMMONIUM CHLORIDE;LAURYLDIMETHYLBENZYL AMMONIUM CHLORIDE;n-dodecyl-n,n-dimethyl-benzenemethanaminium chloride;Benzenemethanaminium,N-dodecyl-N,N-dimethyl-,chloride
• CAS NO: 139-07-1
• Molecular Formula: C₂₁H₃₈N*Cl
• Molecular Weight: 339.99
• EINECS: 205-351-5
• Product Categories: Organics;Biocide;Water Ttreatment Chemicals;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Bactericide and Algicide;API Intermediate
• Mol File: 139-07-1.mol

Chemical Properties

• Melting Point: ~60 °C
• Boiling Point: 162.7℃[at 101 325 Pa]
• Appearance: Pale yellow transparent liquid
• Density: 1.03[at 20℃]
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Store below +30°C.
• Solubility: 866g/L in organic solvents at 20 ℃
• Water Solubility: 2g/L at 20℃
• BRN: 3921689
• CAS DataBase Reference: 1227(CAS DataBase Reference)
• NIST Chemistry Reference: 1227(139-07-1)
• EPA Substance Registry System: 1227(139-07-1)

Safety Data

• Hazard Codes: C,N
• Statements: 21/22-34-50-50/53
• Safety Statements: 36/37/39-45-61-60-26
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 2
• RTECS: BO6821500
• F: 3-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 139-07-1(Hazardous Substances Data)

Usage

Uses

Used in Antimicrobial Applications:
1227 is used as an antimicrobial agent for its effectiveness against various microorganisms, including the Gram-negative bacterium Pseudomonas fluorescens. Its cationic nature allows it to disrupt bacterial cell membranes, leading to cell death and preventing the growth of harmful microorganisms.
Used in Corrosion Inhibition:
1227 is used as a corrosion inhibitor, leveraging its cationic properties to form a protective layer on metal surfaces, thereby preventing corrosion and extending the life of materials in various industrial applications.
Used as a Synergist in Pesticides:
1227 is used as a synergist to enhance the toxicity of the pesticide indoxacarb against various pests. By combining 1227 with other pesticides, it increases their effectiveness and helps in controlling pest populations more efficiently.
Used in Thermal Degradation Studies:
1227 serves as a model for benzyltrialkylammonium salts to study the thermal degradation pathway of benzyl QACs. This research contributes to the understanding of the stability and degradation mechanisms of these compounds, which is crucial for their safe and effective use in various applications.
Used in Pharmaceutical Applications:
1227 is used in the treatment of various infectious diseases, such as herpes, pseudomonas, staph, and hepatitis. Its antimicrobial properties make it a valuable component in the development of pharmaceutical formulations to combat these diseases.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C21H38N.ClH/c1-4-5-6-7-8-9-10-11-12-16-19-22(2,3)20-21-17-14-13-15-18-21;/h13-15,17-18H,4-12,16,19-20H2,1-3H3;1H/q+1;/p-1

Synthetic route

N,N-dimethylaminododecane (112-18-5) + benzyl chloride (100-44-7) → zephirol (139-07-1)

Conditions	Yield
In acetone at 40℃; for 3h; Temperature; Solvent; Large scale;	92.5%
In acetone at 50℃; for 5h; Temperature; Autoclave; Large scale;	91.5%
In water at 60 - 65℃; for 0.3h;	80%

N,N'-dimethylbenzylamine (103-83-3) + 1-chlorododecane (112-52-7) → zephirol (139-07-1)

Conditions	Yield
In ethanol at 80℃; for 28h;	35.3%
In ethanol at 80℃; for 28h;	35.3%
With ethanol

1-dodecyl alcohol (112-53-8) + P2O5 → zephirol (139-07-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc chloride, hydrogen chloride / 13 h / 140 °C 2: H2O / 16 h / 140 - 150 °C 3: H2O / 4 h / 60 - 65 °C View Scheme

1-chlorododecane (112-52-7) → zephirol (139-07-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 16 h / 140 - 150 °C 2: H2O / 4 h / 60 - 65 °C View Scheme

1-dodecylbromide (143-15-7) + copper (I)-benzenethiolate → zephirol (139-07-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol 2: H2O View Scheme

N,N-dimethylaminododecane (112-18-5) + N,N-dimethyl-n-tetradecylamine (112-75-4) + benzyl chloride (100-44-7) → zephirol (139-07-1) + benzyldimethyltetradecylammonium chloride (139-08-2)

Conditions	Yield
at 40 - 90℃; for 25h;
Stage #1: N,N-dimethylaminododecane; N,N-dimethyl-n-tetradecylamine; benzyl chloride In water at 40 - 80℃; Stage #2: at 80 - 90℃; for 2.5h;

1-dodecylbromide (143-15-7) → zephirol (139-07-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; benzene / 20 h / 20 - 25 °C / 760.05 Torr 2: water / 0.3 h / 60 - 65 °C View Scheme
Multi-step reaction with 2 steps 1: water; benzene / 20 h / 20 - 25 °C 2: water / 0.3 h / 60 - 65 °C View Scheme

ethylene glycol mono-n-dodecyl ether (4536-30-5) → zephirol (139-07-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; phosphorus tribromide / 2 h / -10 - 25 °C 2: water; benzene / 20 h / 20 - 25 °C 3: water / 0.3 h / 60 - 65 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine; phosphorus tribromide / 2 h / -10 - 25 °C 2: sodium hydroxide / water; benzene / 20 h / 20 - 25 °C / 760.05 Torr 3: water / 0.3 h / 60 - 65 °C View Scheme

zephirol (139-07-1) + rac-Potassium mandelate (84864-61-9) → benzyldimethyldodecylammonium mandelate (1287759-37-8)

Conditions	Yield
In water at 60℃; for 6h;	99%

zephirol (139-07-1) → N,N-Dimethyl-N-sulfobenzyl-N-dodecylammonium (65180-40-7)

Conditions	Yield
With chlorosulfonic acid at 50℃; under 1500.15 Torr; for 14h; Temperature; Large scale;	98.74%
With sulfur trioxide In 1,2-dichloro-ethane at 40 - 55℃; for 3h; Temperature; Large scale;	98.22%

1,2,3-Benzotriazole (95-14-7) + zephirol (139-07-1) → benzyldimethyldodecylammonium benzotriazole

Conditions	Yield
With sodium hydroxide In water at 70℃; Heating;	96%

sodium bis(2-ethylhexyl)-sulfosuccinate + zephirol (139-07-1) → benzyldimethyldodecylammonium di-(2-ethylhexyl)sulfosuccinic acid

Conditions	Yield
In water; acetone at 25℃; for 168h; Inert atmosphere;	95%

zephirol (139-07-1) + 2-chloro-3-nitro-5-trifluoromethylbenzene (121-17-5) → 2-nitro-4-trifluoromethylphenol (400-99-7)

Conditions	Yield
With sodium hydroxide In hydrogenchloride; methanol	91%

sodium molybdate dihydrate (7631-95-0) + dihydrogen peroxide (7722-84-1) + oxalic acid (144-62-7) + zephirol (139-07-1) → C2MoO9(2-)*2C21H38N(1+)

Conditions	Yield
Stage #1: sodium molybdate dihydrate; dihydrogen peroxide With sulfuric acid In water pH=2; Stage #2: oxalic acid; zephirol In water for 0.0833333h; pH=2; Cooling with ice;	85%

zephirol (139-07-1) + benzenesulfonyl chloride (1939-99-7) → phenylmethylsulphonyl fluoride (329-98-6)

Conditions	Yield
With potassium fluoride In dichloromethane; water	77%

zephirol (139-07-1) → Benzyl Thiosulphate

Conditions	Yield
	48%

zephirol (139-07-1) → carbon dioxide (124-38-9)

Conditions	Yield
With oxygen; titanium(IV) oxide In water Rate constant; Mechanism; Irradiation; on the surface of admixed TiO2, various reaction times;

1,1,1-trichloro-2,2-bis-(o-chlorophenyl)ethane (6734-84-5) + zephirol (139-07-1) → 1,1-bis(chlorophenyl)-2,2-dichloroethylene (3328-98-1)

Conditions	Yield
With sodium hydroxide In water; chlorobenzene
With sulfuric acid In water

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate (6289-46-9) + zephirol (139-07-1) + 4-chloro-aniline (106-47-8) → 2,5-di(4-chloro-anilino)terephthalic acid (41680-76-6)

Conditions	Yield
With hydrogenchloride In methanol; water; acetic acid

m-nitrobenzaldehyde dimethylacetal (3395-79-7) + zephirol (139-07-1) → 3-nitro-benzaldehyde (99-61-6)

3-(1'-cyclohexenyl)-2-methylbenzaldehyde + zephirol (139-07-1) + 2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropane-1-carboxylic acid chloride (59952-40-8, 55710-82-2, 60269-51-4, 61914-49-6, 68198-95-8, 68198-96-9, 73952-09-7, 121313-43-7) → 3-(2',2'-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid-[3-(1'-cyclohexenyl)-2-methyl-α-cyanobenzyl]-ester

Conditions	Yield
In water

2,4-dichlorophenoxyethyl bromide + zephirol (139-07-1) + 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-1-ethanol (58905-18-3) → 1-(2,4-dichlorophenyl)-1-(2,4-dichlorophenoxyethoxy)-2-(1,2,4-triazol-1-yl)-1-ethanol

Conditions	Yield
With sodium hydroxide In diethyl ether; toluene

2-methoxy-phenylamine (90-04-0) + zephirol (139-07-1) + 1,2-dichloro-ethane (107-06-2) → 3-methoxybenzenesulphochloride

Conditions	Yield
With CuCl2; sulfur dioxide; dihydrogen peroxide

4,4'-isopropylidenedicyclohexanol (13804-54-1, 13804-57-4, 13804-58-5, 80-04-6) + zephirol (139-07-1) + 3-chloroprop-1-ene (107-05-1) → perhydrobisphenol A diallyl ether (81866-55-9)

Conditions	Yield
With sodium hydroxide In water; toluene

N-(1-chloroethyl)-pyrazole hydrochloride + 2-ethyl-6-methyl-chloroacetanilide + zephirol (139-07-1) → 2-ethyl-6-methyl-N-(pyrazol-1-yl-eth-1-yl)-chloroacetanilide

Conditions	Yield
With sodium hydroxide In dichloromethane; water

zephirol (139-07-1) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) + 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (55219-65-3, 70585-35-2, 70585-37-4, 82200-72-4, 89482-17-7, 89497-63-2, 89497-64-3, 89497-65-4, 89497-66-5) + naphthalene-1,5-disulfonate (81-04-9) → 2-(4-chlorobenzyloxy)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butane naphthalene-1,5-disulphonate

Conditions	Yield
In acetone; toluene

zephirol (139-07-1) + benzyldimethyltetradecylammonium chloride (139-08-2) + sodium cyclamate (139-05-9) → C21H38N(1+)*C6H12NO3S(1-) + C23H42N(1+)*C6H12NO3S(1-)

Conditions	Yield
In water at 20℃; for 24h; Overall yield = 92 %;

sodium dodecyl-sulfate (151-21-3) + zephirol (139-07-1) → benzyldimethyldodecylammonium dodecylsulfate

Conditions	Yield
In water

sodium tetraphenyl borate (143-66-8) + zephirol (139-07-1) → benzyldimethyldodecylammonium tetraphenylborate

Conditions	Yield
In water

Upstream product

• 112-18-5 N,N-dimethylaminododecane 
• 100-44-7 benzyl chloride 
• 103-83-3 N,N'-dimethylbenzylamine 
• 112-52-7 1-chlorododecane 
• 4536-30-5 ethylene glycol mono-n-dodecyl ether 
• 143-15-7 1-dodecylbromide 
• 112-75-4 N,N-dimethyl-n-tetradecylamine 
• 112-53-8 1-dodecyl alcohol 

Downstream Products

• 3328-98-1 1,1-bis(chlorophenyl)-2,2-dichloroethylene 
• 41680-76-6 2,5-di(4-chloro-anilino)terephthalic acid 
• 99-61-6 3-nitro-benzaldehyde 
• 81866-55-9 perhydrobisphenol A diallyl ether 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 400-99-7 2-nitro-4-trifluoromethylphenol 
• 65180-40-7 N,N-Dimethyl-N-sulfobenzyl-N-dodecylammonium 
• 1287759-37-8 benzyldimethyldodecylammonium mandelate 
• 1427515-38-5 bis(benzyldimethyldodecylazaniumyl)tetrachloroplatinumdiuide 

Relevant articles and documents

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The invention discloses a benzalkonium chloride preparation method, which comprises: (1) carrying out a salt formation reaction on a fatty alkyl dimethyl tertiary amine and benzyl chloride in an organic solvent at a temperature of 30-70 DEG C to obtain fatty alkyl dimethyl benzyl ammonium chloride, wherein the fatty alkyl is dodecyl, tetradecyl or hexadecyl, and the organic solvent is one or a plurality of materials selected from methanol, ethanol, n-propanol, isopropanol, acetone and acetonitrile; and (2) in an organic solvent, crystallizing the mixture containing two or three fatty alkyl dimethyl benzyl ammonium chlorides prepared in the step (1). According to the present invention, the preparation method has advantages of simple process and high yield, wherein the yield can achieve morethan 90%; the content of the related substance is low, and the purity is high, and can achieve more than 99%; the water content is low; and the product has good appearance and simple post-treatment effect, can meet the requirements of various pharmacopoeia, and is suitable for the industrial production of pharmaceutical-grade benzalkonium chloride.

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The invention relates to a synthetic method of aryl sulphobetaine in a solvent-free system. The method comprises the steps that alkyl dimethyl tertiary amine and benzyl chloride which are close to the stoichiometric ratio react to synthetize alkyl dimethyl benzyl ammonium chloride at a low temperature, under high-speed stirring of a planetary stirrer and dilution of dry air in the solvent-free system, alkyl dimethyl benzyl ammonium chloride is added into chlorosulfonic acid close to the stoichiometric ratio step by step for a reaction, and alkyl dimethyl benzyl sulphobetaine is obtained. According to the method, no solvent is needed, the production cost is low, a small amount of residual chlorosulfonic acid obtained after a solvent-free reaction can be recycled through high-speed centrifugation, and the yield of alkyl dimethyl benzyl sulphobetaine can reach 98% or above.

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