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Home > Encyclopedia > 3-(Chloromethyl)pyridine hydrochloride

3-(Chloromethyl)pyridine hydrochloride

3-(Chloromethyl)pyridine hydrochloride structure

3-(Chloromethyl)pyridine hydrochloride 

structure
  • CAS No:

    6959-48-4

  • Formula:

    C6H6ClN.ClH

  • Chemical Name:

    3-(Chloromethyl)pyridine hydrochloride

  • Synonyms:

    Pyridine,3-(chloromethyl)-,hydrochloride (1:1);Pyridine,3-(chloromethyl)-,hydrochloride;3-(Chloromethyl)pyridine hydrochloride;3-Pyridylmethyl chloride hydrochloride;3-(Chloromethyl)pyridine monohydrochloride;3-Picolyl chloride hydrochloride;(Pyridin-3-yl)methyl chloride hydrochloride;3-(Chloromethyl)pyridinium chloride

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

White to pale brown solid


3-(chloromethyl)pyridine hydrochloride appears as yellow powder or yellow-tan solid with an irritating odor. (NTP, 1992)


3-(chloromethyl)pyridine hydrochloride appears as yellow powder or yellow-tan solid with an irritating odor. (NTP, 1992)

3-(Chloromethyl)pyridine hydrochloride Basic Attributes

164.03

162.995560

3689156

230-150-4

BQA8FYP4YN

66482

2811

DTXSID6020309

29333999

Characteristics

12.9

2.62240

White to beige Crystalline Needles or Powder

137-143 °C

210°C at 760 mmHg

62ºC

H2O: >=10 g/100 mL at 19 ºC

Store at RT.

Oral-Rat  LD50: 316 mg/kg; Oral-Mouse LD50: 316 mg/kg

Combustible, decomposes toxic chloride, nitrogen oxide gas when burning

Hygroscopic. Water soluble.

Amines, Phosphines, and Pyridines

3-(CHLOROMETHYL)PYRIDINE HYDROCHLORIDE is incompatible with strong oxidizing agents and strong bases. (NTP, 1992)

Safety Information

8

2811

3

22-36/37/38-45-20/21/22-34

26-36-53-45-36/37/39

US7000000

Xn,C,T

Storeroom low temperature, ventilated, dry; fireproof; stored separately from oxidants, food ingredients

Corrosive

Stable under normal temperatures and pressures.

P280-P305 + P351 + P338-P310

H302-H314

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Bioassay of 3-(Chloromethyl)pyridine hydrochloride for Possible Carcinogenicity (1978) Technical Rpt Series No. 95 DHEW Pub No. (NIH) 78-1345, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501|Aggregated GHS information provided by 49 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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 store this material at ambient temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Pyridine and its derivatives cause local irritation on contact with the skin, mucous membranes and cornea. /Pyridine and its derivatives/

Toxicity

highly toxic

LD50 Rat oral 316 mg/kg|LD50 Mouse oral 316 mg/kg

A bioassay of 3-(chloromethyl)pyridine hydrochloride for possible carcinogenicity was conducted by administering the test chemical by gavage to Fischer 344 rats and B6C3F1 mice. Groups of 50 rats and 50 mice of each sex were administered 3-(chloromethyl)pyridine hydrochloride in a vehicle of distilled water three times/wk at one of the following doses, either 75 or 150 mg/kg body weight for the rats and either 100 or 200 mg/kg body weight for the mice. The low dose rats were dosed for 103 wk and the low dose mice for 102 wk. Because of early deaths in the high dose animals, the high dose rats were dosed for only 83 wk and the high dose mice for only 81 wk. Controls consisted of groups of 20 rats and 20 mice of each sex which were administered the vehicle only for 104 wk. All surviving rats and mice were /sacrificed/ at 104 wk. ... Under the conditions of this bioassay, 3-(chloromethyl)pyridine hydrochloride was carcinogenic in male Fischer 344 rats and B6C3F1 mice of both sexes, producing papillomas and carcinomas at the site of topical application, the stomach. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Equivocal; Male Mice: Positive; Female Mice: Positive.

Drug Information

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Symptoms of exposure to a similar compound include a burning sensation, coughing, wheezing, laryngitis shortness of breath, headache, nausea and vomiting. ACUTE/CHRONIC HAZARDS: This chemical is harmful if swallowed, inhaled or absorbed through the skin. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits 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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

3-(chloromethyl)pyridine

3-(Chloromethyl)pyridine hydrochloride Use and Manufacturing

Methods of Manufacturing

A 1000 mL four-neck bottle was placed in an ice water bath.Add 500g (content 99.5percent, After the moisture content of 0.02percent) 3-methylpyridine, Turn on the agitation, The dry hydrogen chloride gas (85g/h) is introduced under normal pressure.Water bath temperature control 0 ° C, Reacting in a dry anhydrous state, After all the white solid hydrochloride is formed, Stop stirring and continue to pass hydrogen chloride gas.The solid begins to dissolve, After introducing hydrogen chloride gas for 9 hours, 1265 g of liquid 3-methylpyridine hydrochloride was obtained (quantitative 3-methylpyridine content was39.53percent).Transfer the above hydrochloride to a 2000 mL four-necked flask and place in an oil bath.After the stirring is started and the temperature is raised to 125 ° C, the chlorine gas after drying is started.Ventilation speed 50g/h, After 8h, the gas phase detection result was 3-methylpyridine: 3-chloromethylpyridine = 45:52 (gas phase qualitative ratio), Stop the chlorine and cool down to 110 ° C, at this temperature, Distilled under reduced pressure at a pressure of -0.08 MPa, A total of 236 g of distillate was obtained.Is unreacted 3-methylpyridine, The quantitative 3-methylpyridine content is 98.2percent;The remaining bottom material is a light yellow solid.3-chloromethylpyridine hydrochloride, A total of 459.9g, The quantitative 3-chloromethylpyridine content is 73.88percent, The yield was calculated to be 93.26percent.Step B: Preparation of 3-(Chloromethyl)pyridine hydrochloride. Thionyl chloride (9.60 g, 80.6 mmol) was added dropwise to a stirred solution of (pyridin-3-yl)methanol (2.20 g, 20.1 mmol) in 30 ml of CHCl

Uses

Used as pharmaceutical intermediate

Production

(1977) NOT PRODUCED COMMERCIALLY IN USA|(1979) NOT PRODUCED COMMERCIALLY IN USA

VARIOUS TLC SYSTEMS FOR THE SEPARATION OF 2-, 3-, & 4-SUBSTITUTED PYRIDINES ARE DESCRIBED.|OSW Method 8270B. Determination Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique. Estimated quantitation limit=100 ug/l.|SFSAS_29. Extraction and Analysis of Organics in Biological Tissue. Capillary gas chromatography/mass spectrometry analysis. Limit of quantitation=2 mg/kg.

Computed Properties

Molecular Weight:164.03
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:162.9955546
Monoisotopic Mass:162.9955546
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:65.5
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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