Benzethonium chloride
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Benzethonium chloride
structure -
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CAS No:
121-54-0
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Formula:
C27H42NO2.Cl
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Chemical Name:
Benzethonium chloride
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Synonyms:
Benzenemethanaminium,N,N-dimethyl-N-[2-[2-[4-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]-,chloride (1:1);Ammonium,benzyldimethyl[2-[2-[p-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]-,chloride;Benzenemethanaminium,N,N-dimethyl-N-[2-[2-[4-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]-,chloride;Benzethonium chloride;Benzetonium chloride;Benzyldimethyl[2-[2-[p-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]ammonium chloride;BZT;Diapp;Anti-Germ 77;Hyamine 1622;p-tert-Octylphenoxyethoxyethyldimethylbenzylammonium chloride;Phemeride;Phemerol chloride;Polymine D;Quatrachlor;Phemerol;Benzyldimethyl[2-[2-[4-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]ammonium chloride;(Diisobutylphenoxyethoxyethyl)dimethylbenzylammonium chloride;Phemithyn;Solamin;[2-[2-(4-Diisobutylphenoxy)ethoxy]ethyl]dimethylbenzylammonium chloride;Antiseptol;MED 81;N-Benzyl-N,N-dimethyl-N-(4-[1,1,3,3-tetramethylbutyl]phenoxyethoxyethyl)ammonium chloride;Antiseptol (quaternary compound);Bencetonium chloride;Benzethionium chloride;LonzaGuard;2-[2-[p-(Diisobutyl)phenoxy]ethoxy]ethyldimethylbenzylammonium chloride;Bian Suo Lv An;Hyamine 1622M;39362-38-4;324034-09-5
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CAS No:
Description
Benzethonium chloride inhibit human recombinant α7 and α4β2 neuronal nicotinic acetylcholine receptors in Xenopus oocytes.
Benzethonium chloride appears as odorless white crystals or powder with a very bitter taste. A 1% solution in water is slightly alkaline to litmus. (NTP, 1992)|COLOURLESS OR WHITE HYGROSCOPIC SOLID IN VARIOUS FORMS.
Benzethonium chloride appears as odorless white crystals or powder with a very bitter taste. A 1% solution in water is slightly alkaline to litmus. (NTP, 1992)|Benzethonium chloride is a (synthetic) quaternary ammonium salt that is benzyldimethylamine in which the nitrogen is quaternised by a 2-{2-[p-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl group, with chloride as the counter-ion. An antiseptic and disinfectant, it is active against a broad spectrum of bacteria, fungi, moulds and viruses. It has a role as an antiseptic drug, a disinfectant, an antibacterial agent, an antiviral agent and an antifungal agent. It is a quaternary ammonium salt, a chloride salt and an aromatic ether.|Bactericidal cationic quaternary ammonium surfactant used as a topical anti-infective agent. It is an ingredient in medicaments, deodorants, mouthwashes, etc., and is used to disinfect apparatus, etc., in the food processing and pharmaceutical industries, in surgery, and also as a preservative. The compound is toxic orally as a result of neuromuscular blockade.
Benzethonium chloride Basic Attributes
448.08
447.290405
3898548
204-479-9
PH41D05744
0387
755908|20200
DTXSID6023810
COLORLESS CRYSTALS
D - Dermatologicals
29239000
Characteristics
18.5
4.0
White Liquid
0.998 g/mL at 20 °C
164-166 °C
INDEX OF REFRACTION: 1.5101 @ 25 °C/D; INDEX OF REFRACTION FALLS ON REPETITION|INDEX OF REFRACTION: 1.560 (ALPHA), 1.565 (BETA), 1.589 (GAMMA)
H2O: 1-5 g/100 mL at 18 ºC
Store at +15°C to +25°C.
Oral-rat LD50: 368 mg/kg; Oral-Mouse LD50: 338 mg/kg
Combustible; burning produces toxic nitrogen oxides, ammonia and chloride fumes
MILD ODOR
VERY BITTER TASTE
PH OF 1% AQ SOLN IS BETWEEN 4.8 & 5.5
210.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
SPLINTERS SLIGHTLY @ 120 °C|OPTIC SIGN + ; AXIAL ANGLE 2V= 48 DEG; MOST FRAGMENTS DO NOT EXTINGUISH COMPLETELY|HYDROPHILIC PART OF MOLECULE IS POSITIVE RATHER THAN NEGATIVE; DETERGENTS RELEASE ANION (CL- OR BR-) /CATIONIC DETERGENTS/|MINERAL ACIDS & MANY SALT SOLN PPT BENZETHONIUM CHLORIDE FROM SOLN MORE CONCN THAN 2% AS OIL WHICH CRYSTALLIZES ON DRYING|For more Other Experimental Properties (Complete) data for BENZETHONIUM CHLORIDE (7 total), please visit the HSDB record page.
Hygroscopic. May be sensitive to prolonged exposure to air. Water soluble.
Ethers
BENZETHONIUM CHLORIDE is incompatible with strong oxidizing agents. Incompatible with soap and anionic detergents. Can react with nitrates. Sensitive to light. Acids cause it to precipitate from aqueous solutions of >2% concentration. Stable for two weeks at temperatures up to 140 F, (NTP, 1992).
Safety Information
III
8
UN1759
2
22-37/38-41-36-36/37/38-20/21/22-50/53-34-52/53
26-36/39-24/25-36/37/39-61-45
BO7175000
Xn,N,C
Ventilated, low temperature and dry; stored separately from food materials in warehouse
Stability Stable, but hygroscopic. Incompatible with strong oxidizing agents, soap, anionic detergents, nitrates, acids. Light sensitive.
P273-P280-P301 + P310-P305 + P351 + P338-P310-P501
H301-H314-H410
INCOMPATIBILITIES: INCOMPATIBLE WITH & INACTIVATED BY SOAPS, ANIONIC DETERGENTS, ORGANIC MATERIAL, & NITRATES.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
HECHT A; STANDARDS FOR NONPRESCRIPTION GERM KILLERS. FDA CONSUM 12(JUL-AUG) 15 (1978). THE FOOD AND DRUG ADMINISTRATION'S TENTATIVE STANDARDS FOR A VARIETY OF OVER-THE-COUNTER DRUGS THAT ARE USED TO KILL GERMS ON THE SKIN ARE DISCUSSED INCL THE INGREDIENT BENZETHONIUM CHLORIDE WHICH HAS BEEN FOUND SAFE & EFFECTIVE.
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H301 (74.45%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P273, P280, P301+P310, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 279 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, and P501
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. RECOMMENDED GLOVE MATERIALS: Permeation test results for handling the neat (undiluted) chemical. If this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, replace them at once. Glove Type Model Number Thickness Bkthru Time Butyl rubber North B-174 0.64 mm 480 min. Latex Ackwell 0.18 mm 480 min. Neoprene Edmont 29-870 0.48 mm 480 min. Polyvinyl Edmont 34-100 0.20 mm 480 min. chloride Permeation Test Results of Diluted Chemical in 95% ethanol: The breakthrough times of the diluted chemical at three different concentrations are given for each glove type. If a solution of this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, replace them at once Glove Type Model Number 100 mg/mL 1.2 mg/mL 0.03 mg/mL Neoprene Edmont 29-870 480 min. Unknown 480 min. PVC Edmont 34-100 480 min. 480 min. 480 min. Unknown North 480 min. 480 min. 480 min. Silvershield (NTP, 1992)|Wear skin protection. Hot conditions may necessitate use of self-contained breathing apparatus.
Alcohol foam, carbon dioxide, dry chemical, water fog /Hyamine cmpd/
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Separated from food and feedstuffs. Store in an area without drain or sewer access. Dry.
The substance is corrosive to the eyes. The substance is irritating to the skin.
Repeated or prolonged contact with skin may cause dermatitis.
NO open flames.
Use ventilation (not if powder).
Protective gloves.
Wear safety goggles.
Toxicity
highly toxic
... Male and female F344/N rats and B6C3FI mice were topically administered benzethonium chloride (greater than 98% pure) for ... 2 yr. ... 2 YEAR STUDY IN RATS: Groups of 60 male and 60 female F344/N rats were topically administered 0, 0.15, 0.5, or 1.5 mg benzethonium chloride/kg body weight 5 days/wk for 103 wk. ... 2 YEAR STUDY IN MICE: Groups of 60 male and 60 female B6C3F1 mice were topically administered 0, 0.15, 0.5, or 1.5 mg benzethonium chloride/kg body weight 5 days/wk for 103 wk. Doses were administered in ethanol, and dose volumes were adjusted weekly according to the average body weights of the groups. ... CONCLUSIONS: Under the conditions of these 2 yr dermal studies, there was no evidence of carcinogenic activity of benzethonium chloride in male or female F344/N rats receiving 0.15, 0.5, or 1.5 mg/kg. There was no evidence of carcinogenic activit,v in male or female B6C3F1 mice receiving 0.15, 0.5, or 1.5 mg/kg.|Benzethonium chloride was prepared in 95% ethanol, which also served as the vehicle. A 0.5% solution of 1-fluoro-2,4-dinitrobenzene ... was used as the positive control. In the primary irritancy studies, a 10% concentration of benzethonium chloride was not significantly irritating, therefore, 20% was chosen as the challenge concentration. For the hypersensitivity test, /female/ B6C3F1 mice were divided into 7 treatment groups of 8 mice/group and administered the test compound at the concentrations shown in Table 1. The irritancy response was determined by monitoring the extravasation of 125I-bovine serum albumin into the testing area. The contact hypersensitivity response was determined by monitoring the infiltration of 125I- iododeoxyuridine labeled cells into the challenge site. ... There were no treatment-related effects on survival or body weights. The Hypersensitivity Index (HI) values obtained with benzethonium chloride sensitization at 1%, 3%, and 10% were not significantly different from the baseline control value. The positive control group (6) produced a statistically significant hypersensitivity response at a sensitizing and challenge concentration of 0.5% 1-fluoro-2,4-dinitrobenzene. ... Under these experimental conditions, no statistically significant group or dose-dependent contact hypersensitivity responses to benzethonium chloride were observed in mice by dermal exposure.
Drug Information
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)
PERCUTANEOUS ABSORPTION IS PROBABLY INSIGNIFICANT. /BENZALKONIUM CHLORIDE/
SYMPTOMS: Symptoms of exposure to this compound may include vomiting, collapse, convulsions and coma. Other symptoms may include corrosion or injury to the mucous membranes. It may cause nausea, esophageal damage and necrosis, hypotension and death. It may also cause dyspnea, cyanosis, paralysis of respiratory muscles possibly leading to asphyxia, and central nervous system depression (possibly with convulsions or preceded by excitement). It has depolarizing muscle relaxant properties. It can cause irritation to the skin, eyes, mucous membranes and upper respiratory tract. Intravenous or intrauterine administration may cause hemolysis. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by ingestion. It is also harmful by inhalation or skin absorption. It is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. When heated to decomposition this chemical emits very toxic fumes of carbon monoxide, carbon dioxide, nitrogen oxides and hydrogen chloride gas. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
... USED AS SPERMATOCIDES ... CAN CAUSE VAGINAL IRRITATION, WITH BURNING SENSATIONS & ITCHING.|FATAL DOSE BY INGESTION IS EST TO BE 1-3 G. AT LEAST 3 FATALITIES HAVE OCCURRED FROM ACCIDENTAL INGESTION. /CATIONIC DETERGENTS/|Ingestion may cause vomiting, collapse, convulsions, coma.|Highly toxic by ingestion; 1 gram may be fatal.
Bencetonium Chloride
The substance can be absorbed into the body through the skin and by ingestion.
Redness. Pain.
Redness. Blurred vision. Pain. Severe burns.
Benzethonium chloride Use and Manufacturing
P-(1, 1, 3, 3-tetramethylbutyl)phenoxyethoxyethyl dimethylamine is prepared from p(diisobutyl)phenol, dichlorodiethyl ether and dimethylamine, and Warm it with benzyl chloride in benzene for 2h to evaporate benzene to obtain benzethonium chloride.
In cosmetics as preservative; cationic surfactant.As disinfectant in dairies and food industries.Clinical reagent for determination of protein in CSF; pharmaceutic aid (preservative).
< 25,000 lb
Aqueous solution, crystals, ethanol/water solution.|V-TERGENT 8X, DETERGENT- DEODORANT; COMPOSITION: BENZETHONIUM CHLORIDE 1.6%; ISOPROPYL ALC 13.5%. APPLICATIONS: WIDELY USEFUL DETERGENT & DEODORANT. LIQUEFIES PUS & FATTY EXUDATES.|BENZETHONIUM CHLORIDE, USP (PHEMEROL CHLORIDE), AVAIL AS 0.133 & 3% SOLN, 0.2% TINCTURE, & 0.2% VAGINAL FOAM.|GRADE: NATIONAL FORMULARY.
Benzenemethanaminium, N,N-dimethyl-N-[2-[2-[4-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]-, chloride (1:1): ACTIVE|THE CATIONIC DETERGENTS...SUCH AS BENZETHONIUM CHLORIDE...ARE SYNTHETIC DERIVATIVES OF AMMONIUM CHLORIDE.|A COMBINATION OF CATIONIC GERMICIDE & ANIONIC POLYMER FOR SORPTION ONTO THE TOOTH SURFACE INHIBITING CALCULUS OR PLAQUE FORMATION. BENZETHONIUM CHLORIDE IS AN INGREDIENT IN THE MOUTHWASH FORMULATION.|IT IS OF ONLY LIMITED VALUE IN TREATMENT OF FUNGUS INFECTIONS.|WHEN APPLIED TO SKIN, THEY TEND TO FORM A FILM UNDER WHICH BACTERIA MAY REMAIN VIABLE; INNER SURFACE OF FILM HAS LOW BACTERICIDAL POWER WHEREAS OUTER SURFACE IS STRONGLY BACTERICIDAL. THEY DO NOT KILL SPORES. ... ACTION IS RATHER SLOW WHEN COMPARED TO THAT OF IODINE. /QUATERNARY AMMONIUM COMPD/|For more General Manufacturing Information (Complete) data for BENZETHONIUM CHLORIDE (13 total), please visit the HSDB record page.
THIS SPECTROPHOTOMETRIC METHOD SHOWED GOOD RESULTS @ CONCN OF 0-300 UG/ML & IN THE PRESENCE OF SEVERAL DRUGS.|SPECTROPHOTOMETRIC METHOD WAS DEVELOPED TO DETECT TRACE AMT OF BENZETHONIUM, WHICH WAS EXTRACTED WITH NITROBENZENE FROM AN AQ ALKALINE SOLN. /BENZETHONIUM/|USING GLASS CAPILLARY GC AND ION-PAIR REVERSED-PHASE HPLC, BENZETHONIUM CHLORIDE AND ITS CRESOL ANALOGUE WERE EFFECTIVELY RESOLVED AND QUANTIFIED.|SURFACTANT QUATERNARY AMMONIUM SALTS ALONE OR IN PHARMACEUTICAL PREPNS, INCLUDING BENZYLTHONIUM CHLORIDE WERE DETD BY POTENTIOMETRIC TITRATION OF AQ SOLN.|For more Analytic Laboratory Methods (Complete) data for BENZETHONIUM CHLORIDE (7 total), please visit the HSDB record page.
Cosmetics -> Preservative
Computed Properties
Molecular Weight:448.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:12
Exact Mass:447.2904073
Monoisotopic Mass:447.2904073
Topological Polar Surface Area:18.5
Heavy Atom Count:31
Complexity:466
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Benzethonium chloride is a quaternary ammonium compound with broad-spectrum antimicrobial activity. It acts by disrupting the cell membrane of microorganisms, leading to their death. It is effective against Gram-positive and Gram-negative bacteria, fungi, and enveloped viruses. It is commonly used as a disinfectant for skin, mucous membranes, and surfaces due to its low irritation profile. It also serves as a preservative in pharmaceutical and cosmetic formulations.
Registered Holders
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Organo Sintesis,S.A.de C.V.
Active
Japan
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Jiangsu Southeast NanoMaterials Co., Ltd.
Inactive
China
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ROHM AND HAAS CO
Inactive
United States
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