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Butanoyl chloride

Butanoyl chloride structure

Butanoyl chloride 

structure
  • CAS No:

    141-75-3

  • Formula:

    C4H7ClO

  • Chemical Name:

    Butanoyl chloride

  • Synonyms:

    Butanoyl chloride;Butyryl chloride;Butyroyl chloride;n-Butyryl chloride;Butyric chloride;Butyric acid chloride;n-Butanoyl chloride;n-Butyroyl chloride;Butanoic acid chloride

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

It is a colorless to yellowish liquid with the molecular formula C₄H₇ClO. It has a strong pungent odor and is highly reactive with water, releasing hydrogen chloride. It has a boiling point of about 102°C and must be stored in an airtight container that is protected from moisture.

Butanoyl chloride Basic Attributes

106.55100

106.55

205-498-5

2XVM8E16IR

2353

DTXSID5024710

Colorless liquid

2915900090

Characteristics

17.07000

1.55190

Butyryl chloride appears as a clear colorless liquid with a sharp odor. Slightly denser than water. Flash point near 20°F. Severely irritates skin, eyes, and mucous membranes. Used to make other chemicals.

1.0263 g/cm3 @ Temp: 20.6 °C

-89 °C

101-102 °C

18ºC

1.4112-1.4132

Decomposes in water;Dissolves slowly with decomposition in alcohol; miscible with ether

Flammables area

32.9mmHg at 25°C

3.7 (vs air)

Pungent acid chloride odor

Fumes in air. Decomposes exothermically in water to give corrosive hydrochloric acid. Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of Hydrogen Chloride gas will be created in 0.47 minutes.|Slowly dissolves in water with decomposition and formation of a weakly acidic solution. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts.|Hydroxyl radical reaction rate constant = 3.9X10-12 cu cm/molec-sec at 25 °C (est)

Highly flammable. Fumes in air. Decomposes exothermically in water to give corrosive hydrochloric acid. Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of Hydrogen Chloride gas will be created in 0.47 minutes. Experimental details are in the following: "Development of the Table of Initial Isolation and Protective Distances for the 2008 Emergency Response Guidebook", ANL/DIS-09-2, D.F. Brown, H.M. Hartmann, W.A. Freeman, and W.D. Haney, Argonne National Laboratory, Argonne, Illinois, June 2009.

Acyl Halides, Sulfonyl Halides, and Chloroformates

Highly Flammable

BUTYRYL CHLORIDE slowly dissolves in water with decomposition and formation of a weakly acidic solution. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Corrosive to metals

Safety Information

II

3

UN 2353 3/PG 2

1

R11; R34

S16-S23-S26-S36-S45

C

Stable under recommended storage conditions.

P210-P280-P305 + P351 + P338-P310

H225-H314

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Alcohols, oxidizing agents, strong bases.

Special Hazards of Combustion Products: Emits toxic fumes of chlorine gas (USCG, 1999)|Flammable - 3rd degree, Reactive - 2nd degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P234, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P321, P330, P363, P370+P378, P390, P403+P233, P403+P235, P404, P405, and P501|Aggregated GHS information provided by 195 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P321, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 2353 datasheet. 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)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb with earth, sand or other non-combustible material and transfer to containers (except for Hydrazine). Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Approved respirator, chemical-resistant gloves, safety goggles, other protective clothing. (USCG, 1999)|Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Flammable ... .

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Use water spray to cool unopened containers.

Reacts with alcohol and water.|... Corrosive.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition. No smoking. Take measures to prevent the build up of electrostatic charge.|Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.|Table of Water-Reactive Materials Which Produce Toxic Gases.|/GUIDE 132 FLAMMABLE LIQUIDS - CORROSIVE/ Fire or Explosion: Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 132 FLAMMABLE LIQUIDS - CORROSIVE/ Health: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|For more DOT Emergency Guidelines (Complete) data for n-Butyryl chloride (10 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Butyryl chloride is included on the dangerous goods list.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. Butyryl chloride is included on the dangerous goods list.

Toxicity

IDENTIFICATION AND USE: n-Butyryl chloride is a colorless liquid. It is used in organic synthesis. HUMAN STUDIES: The chemical is toxic by ingestion and inhalation, and also a strong irritant. ANIMAL STUDIES: There are no data available.

n-Butyryl chloride's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). Butyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone(2). It is used as an acylation reagent and it is involved in the preparation of chromones and antiproliferative agents(2).

TERRESTRIAL FATE: n-Butyryl chloride decomposes in water to yield hydrochloric acid and butyric acid(1), therefore, leaching in soil and volatilization from moist soil for the parent compound are not expected to be important fate processes(SRC). n-Butyryl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 41.7 mm Hg at 25 °C(1).|AQUATIC FATE: n-Butyryl chloride decomposes exothermically in water to yield hydrochloric acid(1). This decomposition reaction will be the dominant fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyryl chloride, which has a vapor pressure of 41.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyryl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.1 days(SRC), calculated from its rate constant of 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). n-Butyryl chloride fumes in air and decomposes in water to yield hydrochloric acid and butyric acid(2); therefore, n-butyryl chloride vapor in air can react with moisture in air.

The rate constant for the vapor-phase reaction of n-butyryl chloride with photochemically-produced hydroxyl radicals has been estimated as 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). n-Butyryl chloride fumes in air(2). It decomposes exothermically in water to yield corrosive hydrochloric acid. Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of hydrogen chloride gas will be created in 0.47 minutes(2).

n-Butyryl chloride decomposes in water to yield hydrochloric acid(1), therefore, bioconcentration in aquatic organisms is not expected to be an important fate process(SRC).

n-Butyryl chloride decomposes in water to yield hydrochloric acid and butyric acid(1), therefore, leaching in soil is not expected to be an important fate process(SRC).

n-Butyryl chloride decomposes in water to yield hydrochloric acid adn butyric acid(1), therefore, volatilization of n-butyryl chloride from water or moist soil is not expected to be an important fate process(SRC). n-Butyryl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 41.7 mm Hg at 25 °C(1).

Occupational exposure to n-butyryl chloride may occur through inhalation and dermal contact with this compound at workplaces where n-butyryl chloride is produced or used. Available use data indicate that the general population is not exposed to n-butyryl chloride. (SRC)

Drug Information

Extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Inhalation may cause death as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

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 volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting. Thus, the risk of increasing the medical problems by inducing vomiting of a volatile corrosive chemical is very high. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations 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 0.9% saline (NS) 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. Activated charcoal is not effective ... . Do not attempt to neutralize, because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary. Start IV administration of D5W TKO. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/OTHER TOXICITY INFORMATION/ Toxic by ingestion and inhalation. Strong irritant to tissue.

Butanoyl chloride Use and Manufacturing

Methods of Manufacturing

Preparation from butyric acid.

Uses

Butyryl chloride (also known as n-Butyryl chloride, butanoyl chloride, or C-4 Acyl halide) is an organic compound with the chemical formula C4H7ClO. Butyryl chloride is liquid at room temperature, has a colorless to light yellowish appearance and has an extremely strong pungent odor. Butyryl chloride is soluble in almost all aprotic organic solvents, but it decomposes violently by heating and spontaneously decomposes when exposed to moist air or water to form pure hydrochloric acid gas. It also

Production

(1986) No Data

Butanoyl chloride: ACTIVE

Fire Hazards -> Flammable - 3rd degree, Reactive - 2nd degree

Computed Properties

Molecular Weight:106.55
XLogP3:1.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:106.0185425
Monoisotopic Mass:106.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:6
Complexity:51.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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