基本情報
- 標準SMILES
COc1ccc(C(=O)Cl)cc1- InChIKey
MXMOTZIXVICDSD-UHFFFAOYSA-N- 分子式
- C8H7ClO2
- 平均分子量
- 170.59 g/mol
- 単同位体質量
- 170.01345714
概要
4-methoxybenzoyl chloride appears as an amber-colored crystalline solid. Melting point 72 °F. Corrosive to metals and skin. Vapors may cause serious burns to the eyes.
名称と識別子
- 優先名称
- p-Anisoyl chloride
- IUPAC
- 4-methoxybenzoyl chloride
- 現地名
- 4-メトキシベンゾイルクロリド
- 英語名
- 4-Methoxybenzoyl chloride
- 分子式
- C8H7ClO2
- 分子量
- 170.59
名称と別名
名称をさらに表示
データベース識別子
- CAS
100-07-2、1300-64-7- PubChem CID
- 7477
- DTXSID
DTXSID9059204- UNII
- TV6DMQ9451
- EC Number
- 202-816-4
- Nikkaji
- J28.748B
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 2
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 139
実験および物理化学的性質
Chemical Classes
Toxic Gases & Vapors -> Acid Halides
Corrosives
Density
1.26 at 68 °F (USCG, 1999) - Denser than water; will sink
1.261 g/cu cm at 20 °C
Boiling Point
504 °F at 760 mmHg (USCG, 1999)
262-263 °C
Melting Point
72 °F (USCG, 1999)
22 °C
Physical Description
4-methoxybenzoyl chloride appears as an amber-colored crystalline solid. Melting point 72 °F. Corrosive to metals and skin. Vapors may cause serious burns to the eyes.
Clear solid or amber liquid; [Hawley] Liquid or low melting solid; [MSDSonline]
物理化学的性質
- 融点
- 22 °C · 22 °C(lit.)
- 沸点
- 262 · 262-263 °C(lit.)
- 比重(密度)
- 1.26 g/mL · 1.260 g/mL at 20 °C(lit.)
- 蒸気圧
- 1.853 Pa · 1.853Pa at 25℃
- 屈折率
- 20 · n20/D 1.581(lit.)
- 闪点
- 190 °F · 190 °F
- 貯蔵温度
- 2 · 2-8°C
- 外見
- 融解後の液体
- 色
- 無色透明~褐色
- 臭い (Odor)
- 鋭い、貫く。
- 水溶解度
- 水中で反応します。
- Merck
- 14 · 14,673
- BRN
- 471918 · 471918
- Henry's Law Constant
- 1.3 · 1.3×100 mol/(m3Pa) at 25℃, HSDB (2015)
- 安定性
- 安定ですが、水と激しく反応します。圧力の蓄積を防ぐために、材料が保管されている容器に湿気が入らないようにしてください。水、湿気、強塩基、強酸化剤とは相容れない。
- InChI
- 1S/C8H7ClO2/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3
- InChIKey
- MXMOTZIXVICDSD-UHFFFAOYSA-N
- SMILES
- COc1ccc(cc1)C(Cl)=O
- LogP
- 1.52 · 1.52
- CAS データベース
- 100 · 100-07-2(CAS DataBase Reference)
- NISTの化学物質情報
- 4 · 4-Methoxybenzoic acid chloride(100-07-2)
- EPAの化学物質情報
- 4 · Benzoyl chloride, 4-methoxy- (100-07-2)
化学的性質
化学的特性p-Anisoyl chloride, also known as 4-methoxybenzoyl chloride, is an amber-colored crystalline solid with a melting point of 72 °F. It is corrosive to metals and skin. Its vapors may cause serious burns to the eyes. It decomposes upon contact with water or alcohols but is soluble in acetone and benzene. Storage in sealed containers may cause explosion due to pressure build-up from decomposition; it must be stored at low temperatures (5°C).
安全と法規制
GHS分類
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 79 reports by companies from 9 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Chemical: Benzoyl chloride, 4-methoxy-
Status: Active Update: 08-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19721
4-Methoxybenzoyl 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: Irritating hydrogen chloride fumes may be formed. (USCG, 1999)
· Combustible material: may burn but does not ignite readily.
Health Hazards
Vapor irritates mucous membranes. Contact of liquid with eyes or skin causes severe irritation. Ingestion causes severe irritation of mouth and stomach. (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
Decomposed by water; Corrosive to tissue; Explosion risk from Sealed containers due to pressure from decomposition at room temperature; [Hawley] May cause serious burns to eyes; Releases hydrochloric acid by hydrolysis; Emergency treatment: acids; [HSDB] Reacts with moisture forming hydrochloric acid; [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
4-METHOXYBENZOYL CHLORIDE reacts exothermically with bases, including amines. Incompatible with water, strong oxidizing agents, alcohols. Sealed containers held at room temperature may explode, due to slow decomposition that builds up pressure. This situation is more dangerous with heat. May react vigorously or explosively with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
DOT Emergency Guidelines
/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
For more DOT Emergency Guidelines (Complete) data for P-ANISOYL CHLORIDE (8 total), please visit the HSDB record page.
DOT Hazard Classification
Anisoyl chloride
UN1729
Class 8 Corrosive material (49 eCFR § 173.136)
PG II: the degree of danger presented by the material is medium
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
INHALATION: remove to fresh air.
General First Aid:
Fire Fighting Procedures
If material on fire or involved in fire: Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Preventive Measures
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contacted with the material anticipated, wear appropriate chemical protective clothing.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
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.
Isolation and Evacuation
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Immediate precautionary measure
Personal Protective Equipment (PPE)
Goggles and face shield; plastic gloves; protective clothing. (USCG, 1999)
Goggles and face shield; plastic gloves; protective clothing.
Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective gloves, boots and goggles.
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a structure estimation method(2), indicates that p-anisoyl chloride is expected to have very high mobility in soil(SRC). Volatilization of p-anisoyl chloride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). p-Anisoyl chloride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.014 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a structure estimation method(2), indicates that p-anisoyl chloride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.8X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 and 50 days, respectively (SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 1.52(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). p-anisoyl chloride is decomposed in water(8), but the rate of this reaction is not known(SRC). However, the hydrolysis half-life of benzoyl chloride, a structural analog, is on the order of several minutes(9), suggesting that p-anisoyl chloride will undergo rapid hydrolysis in the environment(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-anisoyl chloride, which has an estimated vapor pressure of 0.014 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-anisoyl 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 19 hours(SRC), calculated from its rate constant of 2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). p-Anisoyl chloride absorbs light greater than 290 nm and may be subject to direct photolysis in the environment; however, the rate of this potential reaction is unknown(SRC).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for p-anisoyl chloride can be estimated to be 37(SRC). According to a classification scheme(2), this estimated Koc value suggests that p-anisoyl chloride is expected to have very high mobility in soil(SRC).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Symptomatology (...ingestion or skin contact): 1) corrosion of mucous membranes of mouth, throat...esophagus, with...pain and dysphagia. Necrotic areas...grayish white but soon...blackish discoloration...and sometimes shrunken or wrinkled texture. /Acid/
/SIGNS AND SYMPTOMS/ Symptomatology.../ingestion/: 2. Epigastric pain...may be associated with nausea & vomiting...intense thirst. 3. Circulatory collapse...clammy skin, weak & rapid pulse, shallow resp...scanty urine. ...shock is often...cause of death. 4. Asphyxial death due to glottic edema. /Acid/
/SIGNS AND SYMPTOMS/ Symptomatology.../ingestion/: 5. Ulceration of all membranes and tissues with which acid comes in contact. Ulcerated areas often perforate, leading to mediastinitis and peritonitis. 6. Late esophageal, gastric and pyloric strictures and stenosis...may require...surgical repair, should be anticipated. /Acid/
/SIGNS AND SYMPTOMS/ Symptomatology: 6. ...permanent scars may...appear in cornea, skin and oropharynx. 7. Uncorrected circulatory collapse of several hr...may lead to renal failure and ischemic lesions in liver and heart. /Acid/
For more Human Toxicity Excerpts (Complete) data for P-ANISOYL CHLORIDE (7 total), please visit the HSDB record page.
Environmental Bioconcentration
An estimated BCF of 3 was calculated for p-anisoyl chloride(SRC), using an estimated log Kow of 1.52(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for p-anisoyl chloride is estimated as 7.8X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that p-anisoyl chloride is expected to volatilize from water surfaces(2). However, the hydrolysis half-life of benzoyl chloride, a structural analog, is on the order of several minutes(3), suggesting that p-anisoyl chloride will undergo rapid hydrolysis in the environment. Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 50 days(SRC). p-Anisoyl chloride's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). p-Anisoyl chloride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.014 mm Hg(SRC), determined from a fragment constant method(3).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of p-anisoyl chloride with photochemically-produced hydroxyl radicals has been estimated as 2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 19 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). p-Anisoyl chloride absorbs light greater than 290 nm and may be subject to direct photolysis in the environment; however, the rate of this potential reaction is unknown(SRC). p-Anisoyl chloride is decomposed in water(2), but the rate of this reaction is not known(SRC). However, the hydrolysis half-life of benzoyl chloride, a structural analog, is on the order of several minutes(3), suggesting that p-anisoyl chloride will undergo rapid hydrolysis in the environment(SRC).
Probable Routes of Human Exposure
NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,354 workers (276 of these are female) are potentially exposed to p-anisoyl chloride in the US(1). Occupational exposure to p-anisoyl chloride may occur through inhalation and dermal contact with this compound at workplaces where p-anisoyl chloride is produced or used(SRC).
Environmental Fate/Exposure Summary
p-Anisoyl chloride's production and use as an intermediate for dyes and medications may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 0.014 mm Hg at 25 °C indicates p-anisoyl chloride will exist solely as a vapor in the ambient atmosphere. Vapor-phase p-anisoyl 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 19 hours. p-Anisoyl chloride absorbs light greater than 290 nm and may be susceptible to direct photolysis; however, the rate of this reaction is not known. If released to soil, p-anisoyl chloride is expected to have very high mobility based upon an estimated Koc of 37. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 7.8X10-6 atm-cu m/mole. p-Anisoyl chloride is not expected to volatilize from dry soil surfaces based on its estimated vapor pressure. No biodegradation data were located for anisoyl chloride. If released into water, p-anisoyl chloride is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 4 and 50 days, respectively. p-Anisoyl chloride is decomposed in water, but the rate of this reaction is unpublished. However, the hydrolysis half-life of benzoyl chloride, a structural analog, is on the order of several minutes, suggesting that p-anisoyl chloride will undergo rapid hydrolysis in the environment. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to p-anisoyl chloride may occur through inhalation and dermal contact with this compound at workplaces where p-anisoyl chloride is produced or used. (SRC)
安全データ
- F
- 10-21
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- CA0270000
- ridadr
- UN 1729
- hs_code
- 29163990
- risk_code
- 14-34-67-65-63-48/20-11
- 化審法
- (3)-1684
- 消防法
- 危-4-3-III
- hazard_code
- C,F
- safety_code
- 26-36/37/39-45-62-16
- hazard_class
- 8
- packing_group
- II
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- ストレージクラス
- 8A - Combustible corrosive hazardous materials
- 有毒物質データの
- 100-07-2(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used as intermediate for dyes and medicines; [Hawley]
Intermediate for dyes and medicines
応用分野
用途有機合成用原料。
一般的な説明4-Methoxybenzoyl chloride is one of the reactive acylating agents that can react with carboxylic acids, alcohols and amines to yield respective carboxylic anhydrides, esters and amides. 4-methoxybenzoyl chloride reacts with potassium thiocyanate to yield isothiocyanate derivative via nucleophilic addition-elimination mechanism.
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