염화벤조일

Benzoyl chloride

HCID 7412CAS 98-88-4

기본 정보

표준 SMILES
O=C(Cl)c1ccccc1
InChIKey
PASDCCFISLVPSO-UHFFFAOYSA-N
분자식
C7H5ClO
평균 분자량
140.56 g/mol
단동위원소 질량
140.00289246

개요

Benzoyl chloride appears as a colorless fuming liquid with a pungent odor. Flash point 162 °F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.

이름 및 식별자

우선 이름
Benzoyl chloride
IUPAC
benzoyl chloride
현지명
염화벤조일
영어명
Benzoyl chloride
분자식
C7H5ClO
분자량
140.57

이름 및 동의어

BENZOYL CHLORIDE98-88-4Benzenecarbonyl chlorideBenzoic acid, chloridealpha-Chlorobenzaldehydebenzoic acid chlorideDTXSID9026631Benzaldehyde, alpha-chloro-VTY8706W36DTXCID106631CHEBI:82275RefChem:5591
이름 더 보기
염화벤조일벤조일클로라이드벤젠카르보닐클로라이드염화벤조일벤질 클로라이드벤젠카보닐 염화물벤조산 클로라이드BzClBasic Red 1BENZOYL CHLORIDE Extra PureB 0105BENZOXALONEBenzoylChlorideGr
202-710-8BenzoylchlorideBenzoylChloride-13C7Benzoyl Chloride-13C6MFCD00000653Benzaldehyde, .alpha.-chloro-benzoyl-carbonyl-13c chloridebenzoylchlorid

데이터베이스 식별자

CAS
98-88-4
PubChem CID
7412
DTXSID
DTXSID9026631
ChEMBL
CHEMBL2260719
ChEBI
CHEBI:82275
UNII
VTY8706W36
EC Number
202-710-8
Nikkaji
J3.987J

물성

구조 계산 물성

XLogP
2.9
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
9

실험 및 물리화학적 성질

Chemical Classes · 2건

Toxic Gases & Vapors -> Acid Halides

Carcinogens

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Odor · 3건

Penetrating odor

Fuming pungent

Pungent, aromatic

Density · 5건

1.211 at 77 °F (USCG, 1999) - Denser than water; will sink

1.2070 at 25 °C/4 °C

Relative density (water = 1): 1.21

1.211

1.22 @ 15°C

Color/Form · 4건

Liquid

Transparent, colorless liquid

Colorless, fuming liquid

Colorless to slightly yellow liquid

Solubility · 6건

Decomposes (NTP, 1992)

Decomposed by water, alcohol

Miscible with ethyl ether; soluble in benzene, carbon tetrachloride, carbon disulfide

Miscible with ether, benzene, carbon disulfide, oils

Soluble in ether and carbon disulfide

Solubility in water: reaction

물리화학적 성질

녹는점
-1 °C · -1 °C (lit.)
끓는 점
198 °C · 198 °C (lit.)
밀도
1.211 g/mL · 1.211 g/mL at 25 °C (lit.)
증기 밀도
4.88 · 4.88 (vs air)
증기압
1 mm · 1 mm Hg ( 32 °C)
굴절률
20 · n20/D 1.553(lit.)

화학적 성질

Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible. It is a liquid acyl chloride used as a benzoylating agent.

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Danger

H302 (97.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 6건

Chemical: Benzoyl chloride

Hazard Traits - Carcinogenicity

Benzoyl chloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoyl chloride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13134

Benzoyl 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.)

Other Safety InformationIMAP assessments - Benzoyl chloride: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 3건

Special Hazards of Combustion Products: Highly poisonous phosgene gas may be formed in fires.

· EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily.

Combustible. Many reactions may cause fire or explosion. Gives off irritating or toxic fumes (or gases) in a fire. Above 72 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2건

Flamable when exposed to heat or flame.

At fire temperatures the compound may react violently with water or steam.

Health Hazards · 2건

INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning. (USCG, 1999)

· CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:

Use alcohol-resistant foam, powder, carbon dioxide. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . Wear protective gloves when administering first aid.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Rest. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2건

· 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.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

First Aid · 2건

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:

Safe StorageSee Chemical Dangers. Separated from food and feedstuffs and incompatible materials. Dry. Well closed.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

독성 정보

Ecotoxicity Values · 4건

LC50; Species: Palaemonetes pugio (grass shrimp); Conditions: static, synthetic salt water of the following quality was used: 25 +/- 1 g/L salinity, 30,000-40,000 microsiemens/cm conductivity, pH 8.3-8.7, temperature= 22 +/- 1 °C; Concentration: 180 mg/L for 96 hr (95% confidence interval: 139.0-233.0 mg/L)

LC50; Species: Pimephales promelas (fathead minnow) length 3.2-4.2 cm; Conditions: freshwater, static, 22 °C, pH 7.2-7.9, hardness 40-48 mg/L CaCO3, alkalinity 30-35 mg/L CaCO3; Concentration: 42600 ug/L for 24 hr (95% confidence interval: 35400-57400 ug/L)

LC50; Species: Pimephales promelas (fathead minnow) length 3.2-4.2 cm; Conditions: freshwater, static, 22 °C, pH 7.2-7.9, hardness 40-48 mg/L CaCO3, alkalinity 30-35 mg/L CaCO3; Concentration: 34700 ug/L for 48 hr (95% confidence interval: 28500-45300 ug/L)

LC50; Species: Pimephales promelas (fathead minnow) length 3.2-4.2 cm; Conditions: freshwater, static, 22 °C, pH 7.2-7.9, hardness 40-48 mg/L CaCO3, alkalinity 30-35 mg/L CaCO3; Concentration: 34700 ug/L for 96 hr (95% confidence interval: 28500-45300 ug/L)

Environmental Fate · 3건

TERRESTRIAL FATE: Data concerning the hydrolysis of benzoyl chloride in soil are not available. However, the rate constant for the hydrolysis of benzoyl chloride in water is 4.2X10-2 sec-1 at 25 °C, corresponding to a hydrolysis half-life of 16 sec(1). The hydrolysis half-life is so short that the predominant terrestrial fate of benzoyl chloride is expected to be hydrolysis(SRC). In the absence of water, however, benzoyl chloride could form a variety of esters upon reaction with common soil constituents(SRC). Benzoyl chloride is not expected to adsorb to soils, biodegrade, photolyze, volatilize, or leach(SRC).

AQUATIC FATE: The hydrolysis rate constant for benzoyl chloride in water is 4.2X10-2 sec-1 at 25 °C, which corresponds to a half-life of 16 seconds(1). The products of the hydrolysis reaction are benzoic acid and hydrochloric acid(2). The rapid rate of hydrolysis suggests that hydrolysis is the major aquatic fate process for benzoyl chloride. Volatilization, photolysis, photooxidation, bioconcentration, biodegradation, and adsorption to sediments are not expected to be important processes in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzoyl chloride, which has a vapor pressure of 0.700 mm Hg at 25 deg(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzoyl 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 9 days(SRC), calculated from its rate constant of 1.8X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Benzoyl chloride exhibits an absorption maximum of 282.9 nm (Epsilon = 1752) and also absorption at 293.0 nm (Epsilon = 1108) in methyl cyclohexane(4). Benzoyl chloride in the vapor phase absorbs light from 225-292 nm, but only qualitative estimates of the absorption intensities (weak-strong) were given(4). This suggests that benzoyl chloride may be susceptible to direct photolysis by sunlight(SRC).(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Toxicity Summary · 1건

IDENTIFICATION AND USE: Benzoyl chloride is a transparent, colorless liquid, or slightly brown liquid with a penetrating odor. It is used for for acylation (introduction of benzoyl group into alcohols, phenols, and amines). It is also used in the manufacture of benzoyl peroxide and of dye intermediates, and in organic analysis for making benzoyl derivates for identification purposes. HUMAN STUDIES: Benzoyl chloride has a corrosive effects on the skin, eyes, and mucous membranes by inhalation. It can cause cough, labored breathing, nausea, and sore throat after inhalation. Redness and irritant pain on contact with the eye and skin. Burning sensation, nausea and vomiting upon ingestion. Three cases of lung cancer have been reported among workers engaged in production of benzoyl chloride. ANIMAL STUDIES: Benzoyl chloride was found to be corrosive to rabbit eyes. In male rats exposed to benzoyl chloride by inhalation signs of intoxication included inactivity, piloerection, unkempt fur, and difficulties in breathing up to 19 days post exposure in all rats. Rats that died during the test showed dark red colored lungs always with emphysema, some rats showed lung edema. Rats that survived showed no pathologic findings up to 0.708 mg/L. At higher concentrations lungs showed emphysema and were mottled, some showed enlarged adrenals. Benzoyl chloride was found to induce tumors in mice following inhalation exposure. Benzoyl chloride was positive in the bacterial gene mutation assay, preincubation method in Escherichia coli WP2uvrA/pKM101 with and without activation at concentrations up to 1000 ug/plate. Benzoyl chloride was not mutagenic in Salmonella typhimurium strains His g46, His c3076, His d3052, TA1535, TA1536, TA1537, TA98 or TA100, nor in Escherichia coli strains Wp2 and Wp2 uvra- with or without metabolic activation. Benzoyl chloride was weakly mutagenic to Salmonella strain TA98 in the absence of metabolic activation. ECOTOXICITY STUDIES: In a 96 hr lethality study with the Zebrafish (Brachydanio rerio) no toxicity was found at 7.5 mg/L and all the fish died at 10 mg/L. Benzoyl chloride reacted with water to give benzoic acid and hydrogen chloride, causing a decrease in pH to 5.2 in freshwater and 7.2 in salt water. However, the biological oxygen demand of the benzoic acid was a far more serious effect. In the saltwater test of grass shrimp this was believed to be the major cause of mortality since dissolved oxygen levels plunged below 1 mg/L in direct correspondence to initial benzoyl chloride concentration.

Ecotoxicity Excerpts · 3건

/AQUATIC SPECIES/ The minnows /(Pimephales promelas)/ were raised from controlled breeding stocks at the EPA Newton Fish Toxicology Station, Cincinnati, OH and were observed for a minimum of 14 days prior to testing. The fish were acclimated for 2 days in 100% test dlution water at 22 °C. Bioassay containers were filled with 12 liters of dilution water. Test substance was added in the form of a stock solution in deionized water. Five fish were placed in each of two duplicate aquaria (10 fish/concentration). At 24 hr intervals, fish were observed for survival, and water tested for dissolved oxygen and temperature. At the end of the 96 hr exposure period, pH and test substance concentration was measured by electron capture gas chromatography (benzene: 15% ether extraction). With concentration versus mortality results, 96 hr LC50 and 95% confidence limits were calculated by Probit, Moving average, or Binomial test (depending on the number of partial kills observed). Benzoyl chloride reacted with water to give benzoic acid and HCl, causing a decrease in pH to 5.2 in freshwater and 7.2 in salt water. However, the biological oxygen demand of the benzoic acid was a far more serious effect. ... /The LC50 was calculated at 34.1 mg/L;/ 95% confidence interval = 28.5-45.3 mg/L. Reconstituted soft water of the following quality was used: 40-48 mg/L hardness as CaC03; 30-35 mg/L alkalinity as CaC03; 120-160 uS/cm conductivity; pH 7.2 - 7.9; temperature = 22 +/- 1 °C.

/AQUATIC SPECIES/ In a 96 hr lethality study with the Zebrafish (Brachydanio rerio) no toxicity was found at 7.5 mg/L (LC0) and all the fish died at 10 mg/L. The geometric mean of the two values is 8.7 mg/L. Test conditions: ventillated test medium , static system, 10 animals/vessel. The test substance was weighed directly into the dillution water.

/AQUATIC SPECIES/ The grass shrimp /(Palaeomonetes pugio)/ were collected from wild poulations in an estuary near Galveston Bay, Texas and were observed for a minimum of 10 days prior to testing. Bioassay containers were filled with 12 liters of dilution water. Test substance was added in the form of a stock solution in deionized water. Five grass shrimp were placed in each of two duplicate aquaria (10 fish/concentration). At 24 hr intervals, grass shrimp were observed for survival, and water tested for dissolved oxygen and temperature. At the end of the 96 hr exposure period, pH and test substance concentration was measured by electron capture gas chromatography (benzene:15% ether extraction). With concentration versus mortality results, 96 hr LC50 and 95% confidence limits were calculated by Probit, Moving average, or Binomial test (depending on the number of partial kills observed). Benzoyl chloride reacted with water to give benzoic acid and HCl, causing a decrease in pH to 5.2 in freshwater and 7.2 in salt water. However, the biological oxygen demand of the benzoic acid was a far more serious effect. In the saltwater test of grass shrimp this was believed to be the major cause of mortality since dissolved oxygen levels plunged below 1 mg/L in direct correspondence to initial benzoyl chloride concentration.

규제 정보

Atmospheric Standards · 1건

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzoyl chloride is produced, as an intermediate or a final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1건

Benzoyl chloride is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
DM6600000
ridadr
UN 1736
독성
LD50 orally in Rabbit: 2460 mg/kg LD50 dermal Rabbit 790 mg/kg
HS 번호
29310095

화학 및 산업

약리 정보

Biological Half-LifeThe half-life of the labeled material /(benzoyl chloride)/ in the blood was 1.5 hours.
Metabolism/Metabolites · 2건

When 14C-labeled benzoyl chloride was applied to the dorsal musculature of a male Wistar rat through a small incision, only traces of radioactivity were found in the urine and feces. At 3 days post-application, most of the radioactivity remained at the site of application. The benzoyl chloride appeared to react mostly by acylation of nucleophilic groups and very little hydrolyzed to benzoic acid.

/After/ a single oral dose of labelled benzoyl chloride (9-13 mg/kg bw) administered to rats,/ ... over 90% of the metabolites in the urine were identified as benzoic acid and hippuric acid.

Absorption, Distribution and Excretion · 3건

The absorption and excretion of (14)C-benzoyl chloride was studied in male and female Holtzman albino rats. Following single oral doses of 9 to 13 mg/kg, benzoyl chloride was rapidly absorbed from the gastrointestinal tract and efficiently eliminated in the urine (90%) and feces (2%) within 48 hours. ... After 72 hours, the total radiocarbon residue in tissues was approximately 1.5% of the dose; fat liver, and kidneys contained the highest residue levels.

Elimination and distribution of (14)C-labeled benzoyl chloride in rats were very similar in many respects to that of benzoic acid.

Only a small amount of radioactivity was found in the urine and the feces after application of 10 uL labeled benzoyl chloride through a small incision on the dorsal musculature of male Wistar rats, measured over a period of 15 days. Organ distribution of radioactivity 3 days after application of 10 uL labeled benzoyl chloride through a small incision on the dorsal musculature of male Wistar rats: brain< heart< kidneys< lungs< spleen< skin/muscle.

용도 및 제조

Uses · 6건

Used in chemical production; [HSDB]

For acylation, i.e., introduction of benzoyl group into alcohols, phenols, and amines;. ... in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivates for identification purposes.

Analytical reagent.

The major industrial use of benzoyl chloride is in the production of benzoyl peroxide. Secondary uses include the formulation of herbicides and the production of drugs, plasticizers, and perfumes.

Chemical intermediate for benzoyl peroxide, a polymerization initiator; chloramben, an herbicide; dyes; Benzophenone, a perfume fixative; other benzoyl derivatives; fastness improver for dyed fibers or fabrics; cellulosic yarn treatment agent; chemical intermediate for benzoate plasticizers (former use), pharmaceuticals (former use)

Intermediate for stabilizers and pesticides

ImpuritiesMaximum Limits of Impurities: residue after ignition 0.005%; phosphorus compounds (as P) 0.002%; heavy metals (as Pb) 0.001%; iron (Fe) 0.001%.
U.S. Exports · 2건

(1977) No Data

(1982) No Data

U.S. Imports · 5건

(1977) 1.99X10+8 G (PRINCPL CUSTMS DISTS)

(1982) 9.24X10+8 G (PRINCPL CUSTMS DISTS)

(1975) 203,700 lb

(1976) 166,230 lb

For more U.S. Imports (Complete) data for Benzoyl chloride (8 total), please visit the HSDB record page.

U.S. Production · 4건

2023: 10,000,000 - <25,000,000 lb

(1977) AT LEAST 4.54X10+9 G

(1982) PROBABLY GREATER THAN 4.54X10+6 G

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzoyl chloride:

Consumption PatternsBenzoic peroxide, 57%; herbicides, 39%; dyes, 3%; and plasticizers and drugs, 1% (1977)
응용 분야 · 3건

개요벤조산의 산염화물. 자극적인 냄새가 나는 무색 액체로, 에테르에 녹고 물에서 분해된다.

용도벤조일화제(benzoyl化劑)로 널리 쓴다.

일반 설명Benzoyl chloride appears as a colorless fuming liquid with a pungent odor. Flash point 162 °F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.

제조 방법 · 1건

생산 방법Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:

공급사50 곳

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梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Syntechem Co.,Ltd[email protected]
추가 설명 · 1건

정의ChEBI: Benzoyl chloride is an acyl chloride consisting of benzene in which a hydrogen is replaced by an acyl chloride group. It is an important chemical intermediate for the manufacture of other chemicals, dyes, perfumes, herbicides and pharmaceuticals. It has a role as a carcinogenic agent. It is an acyl chloride and a member of benzenes. It is functionally related to a benzoic acid.

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