4-Methoxybenzoyl chloride
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4-Methoxybenzoyl chloride
structure -
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CAS No:
100-07-2
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Formula:
C8H7ClO2
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Chemical Name:
4-Methoxybenzoyl chloride
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Synonyms:
Benzoyl chloride,4-methoxy-;p-Anisoyl chloride;4-Methoxybenzoyl chloride;p-Methoxybenzoyl chloride;Anisoyl chloride;p-Methoxybenzoic acid chloride;4-Methoxybenzoic acid chloride;4-Anisoyl chloride;Para-anisoyl chloride;NSC 86125;4-Methoxyphenylchloroform
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CAS No:
Description
4-METHOXYBENZOYL CHLORIDE is an amber-colored crystalline solid. Melting point 72°F. Corrosive to metals and skin. Vapors may cause serious burns to the eyes.
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.
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.
4-Methoxybenzoyl chloride Basic Attributes
170.59
170.59
471918
202-816-4
TV6DMQ9451
86125
1729
DTXSID9059204
Clear crystals or amber liquid
2918990090
Characteristics
26.3
1.52 (est)
Clear colorless to brown Liquid After Melting
1.261 g/cm3 @ Temp: 20 °C
24-25 °C
262-263 °C
190 °F
1.530
It reacts in water.soluble in ether and acetone. Very soluble in benzene. Slightly soluble in carbon tetrachloride.
2-8°C
0.014 mm Hg at 25 deg C (est)
Flammable; emit toxic hydrogen chloride gas in water
Sealed containers may explode because slow decomposition at room temperature may build up pressure.
Henry's Law constant = 7.8X10-6 atm-cu m/mol at 25 °C
Decomposed by water or alcohol.|/Anisoyl chloride/ can explode spontaneously at room temperature.|HEAT OF SOLN: (EST) 90 BTU/LB= 50 CAL/G= 2.1X10+5 J/KG|Hydroxyl radical reaction rate constant = 2.0X10-11 cu cm/molec-sec at 25 °C
Fumes in air. Reacts exothermically with water (including moisture in air or soil) to form hydrochloric acid and insoluble anisic acid [Merck 11th ed. 1989].
Acyl Halides, Sulfonyl Halides, and Chloroformates
Water-Reactive
ANISOYL 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].
-10,500 BTU/LB= -5,830 CAL/G= -244X10+5 J/KG (EST)
Safety Information
II
8
UN 1729 8/PG 2
1
14-34-67-65-63-48/20-11
26-36/37/39-45-62-16
CA0270000
C,F
The warehouse is ventilated, low temperature and dry; stored separately from alkali and oxidant
Explosive at room temperature
Stable, but reacts violently with water. Ensure no moisture enters the container in which this material is stored, to prevent pressure build-up. Incompatible with water, moisture, strong bases, strong oxidizing agents.
P280-P305 + P351 + P338-P310
H314
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.
/Anisoyl chloride/ can explode spontaneously at room temperature.|Self-reactive
Special Hazards of Combustion Products: Irritating hydrogen chloride fumes may be formed. (USCG, 1999)
|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 78 companies from 8 notifications to the ECHA C&L Inventory.
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: 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)
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: 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 damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)
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.
Sealed containers may explode because slow decomposition at room temperature may build up pressure.
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.
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.
/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.
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.|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.
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/|Vapors can cause serious eye burns.
Toxicity
p-Anisoyl chloride's production and use as an intermediate for dyes and medications(1) may result in its release to the environment through various waste streams(SRC).
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).
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).
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).
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).
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).
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).
Drug Information
Vapor irritates mucous membranes. Contact of liquid with eyes or skin causes severe irritation. Ingestion causes severe irritation of mouth and stomach. (USCG, 1999)
INHALATION: remove to fresh air. EYES: flush with water for at least 15 min.; get medical attention. SKIN: flush with water; wash well with soap and water. INGESTION: do NOT induce vomiting; give large amounts of water. (USCG, 1999)
/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.
4-Methoxybenzoyl chloride Use and Manufacturing
Prepared by p-methoxybenzoic acid with thionyl chloride.
4-Methoxybenzoyl Chloride is used in the synthesis of stilbene and dihydrostilbene derivatives as potential anti-cancer agents. It is also used in the synthesis of coumarin dimers with potential HIV-1 activity.
Benzoyl chloride, 4-methoxy-: ACTIVE
Computed Properties
Molecular Weight:170.59
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:170.0134572
Monoisotopic Mass:170.0134572
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:139
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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