基本情報
- 標準SMILES
CCCC(=O)Cl- InChIKey
DVECBJCOGJRVPX-UHFFFAOYSA-N- 分子式
- C4H7ClO
- 平均分子量
- 106.55 g/mol
- 単同位体質量
- 106.01854252
概要
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.
名称と識別子
- 優先名称
- Butyryl chloride
- IUPAC
- butanoyl chloride
- 現地名
- ブチリルクロリド
- 英語名
- Butyryl chloride
- 分子式
- C4H7ClO
- 分子量
- 106.55
名称と別名
名称をさらに表示
データベース識別子
- CAS
141-75-3- PubChem CID
- 8855
- DTXSID
DTXSID5024710- ChEMBL
CHEMBL1300263- UNII
- 2XVM8E16IR
- EC Number
- 205-498-5
- Nikkaji
- J2.538K
物性
構造計算による物性
- XLogP
- 1.6
- 極性表面積
- 17.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 1
- 回転可能結合数
- 2
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 51.5
実験および物理化学的性質
Chemical Classes
Toxic Gases & Vapors -> Other Toxic Gases & Vapors
Flammable agents - 3rd degree
Odor
Pungent acid chloride odor
Sharp odor
Density
1.0277 at 68 °F (USCG, 1999) - Denser than water; will sink
1.0263 at 20.6 °C/4 °C
Solubility
Reaction (NTP, 1992)
Dissolves slowly with decomposition in water
Dissolves slowly with decomposition in alcohol; miscible with ether
Flash Point
71 °F (NTP, 1992)
18 °C (64 °F) - closed cup
Boiling Point
216 °F at 760 mmHg (NTP, 1992)
101-102 °C
Melting Point
-128 °F (NTP, 1992)
-89 °C
物理化学的性質
- 融点
- 89 °C · −89 °C(lit.)
- 沸点
- 102 °C · 102 °C(lit.)
- 比重(密度)
- 1.026 g/mL · 1.026 g/mL at 25 °C(lit.)
- 蒸気密度
- 3.7 · 3.7 (vs air)
- 蒸気圧
- 39 hPa · 39 hPa (20 °C)
- 屈折率
- 20 · n20/D 1.412(lit.)
- 闪点
- 71 °F · 71 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- エーテルと混和する。
- 外見
- 液体
- 色
- やや黄色く澄んでいる
- 臭い (Odor)
- 刺激臭
- 爆発限界(explosive limit)
- 2.5 · 2.5-7.3%(V)
- 水溶解度
- 分解する
- 凝固点
- -89 ℃ · -89℃
- Merck
- 14 · 14,1598
- BRN
- 605395 · 605395
- InChI
- 1S/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3
- InChIKey
- DVECBJCOGJRVPX-UHFFFAOYSA-N
- SMILES
- CCCC(Cl)=O
- LogP
- 0.51 at · 0.51 at 25℃
- CAS データベース
- 141 · 141-75-3(CAS DataBase Reference)
- NISTの化学物質情報
- Butanoyl chloride(141-75-3)
- EPAの化学物質情報
- Butanoyl chloride (141-75-3)
化学的性質
化学的特性Butyryl chloride is a colorless to light yellow liquid with a strong pungent odor. It undergoes vigorous hydrolysis with water; decomposes in water; soluble in almost aprotic organic solvents. It is used as an intermediate for organic synthesis for the preparation of pharmaceuticals, agrochemicals, dyes, cellulose esters, and peroxide compounds.
安全と法規制
GHS分類
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P234, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P390, P403+P233, P403+P235, P405, P406, and P501 (click each P-code to see the statement)
危険有害性情報
Regulatory Information
Chemical: Butanoyl chloride
Status: Active Update: 02-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5853
Butyryl chloride: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Emits toxic fumes of chlorine gas (USCG, 1999)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
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)
· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.
Hazards Summary
Evolves HCl when spilled in water; [ERG 2016] A strong irritant; [HSDB] A severe skin, eye, and mucous membrane irritant; Inhalation may cause chemical pneumonitis and pulmonary edema; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause edema and chemical pneumonitis; [MSDSonline]
Reactivity Profile
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].
安全と保護具
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
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.
General First Aid:
Firefighting Hazards
Reacts with alcohol and water.
... Corrosive.
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].
Fire Fighting Procedures
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.
Cleanup Methods
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.
Disposal Methods
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.
Preventive Measures
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.
Isolation and Evacuation
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Immediate precautionary measure
When spilled in water
When spilled in water
毒性情報
Environmental Fate
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.
Ongoing Test Status
EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of May 1, 2017: http://actor.epa.gov/dashboard/]
Artificial Pollution Sources
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).
Volatilization from Water/Soil
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).
Environmental Abiotic Degradation
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).
Probable Routes of Human Exposure
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)
Environmental Fate/Exposure Summary
n-Butyryl chloride's production and use in organic synthesis may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 41.7 mm Hg at 25 °C indicates n-butyryl chloride will exist solely as a vapor in the atmosphere. Vapor-phase n-butyryl chloride will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 4.1 days. n-Butyryl chloride fumes in air and can react with moisture in air. If released to soil, leaching in soil and volatilization from moist soil are not expected to be important fate processes because n-butyryl chloride reacts and decomposes in water. n-Butyryl chloride is expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, n-butyryl chloride decomposes exothermically to yield hydrochloric acid and butyric acid. This decomposition reaction will be the dominant fate process in water. 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)
安全データ
- F
- 13
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 2353
- hs_code
- 2915 90 70
- risk_code
- 11-34
- 化審法
- (2)-632
- 消防法
- 危-4-2-III
- hazard_code
- F,C
- safety_code
- 16-23-26-36-45
- hazard_class
- 3
- packing_group
- II
- 自然発火温度
- 280 °C
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2Eye Dam. 1Flam. Liq. 2Skin Corr. 1B
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 141-75-3(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used for organic synthesis; [HSDB]
Toxic Gas from Spilling Chemical in Water [Category: Other]
Organic synthesis.
応用分野
用途アシル化剤、重合触媒、有機合成用中間体
使用Butyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone. It is also used as an acylation reagent. Further, it is used in the preparation of peroxides such as benzoyl peroxide, benzophenone and t-butyl perbenzoate. In addition to this, it is involved in the preparation of chromones and antiproliferative agents. Butyryl chloride has been used to esterify wood meal dissolved in the ionic liquid, 1-butyl-3-methylimidazolium chloride.
一般的な説明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.
調製方法
製造方法Butyryl chloride is obtained by the reaction of butyric acid with thionyl chloride. Heat the thionyl chloride to reflux, add butyric acid dropwise over approximately 4 hours, reflux for another hour, then distill. Collect the fraction at 95–115°C, redistill once, and collect the fraction at 101–105°C to obtain the final product, with a yield of over 70%. Phosphorus trichloride can also be added to the reaction, yielding a 75% yield.
純化方法Check IR to see if there is a significant peak at 3000-3500 cm-1 (br) for OH. If OH is present then reflux with less than one mole equivalent of SOCl2 for 1hour and distil directly. The fraction boiling between 85-100o is then refractionated at atmospheric pressure. Keep all apparatus free from moisture and store the product in sealed glass ampoules under N2. LACHRYMATORY; handle in a good fume hood. [Hefferich & Schaeffer Org Synth Coll Vol I 147 1941, Beilstein 2 IV 803.]
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