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디클로로아세탈디히드

Dichloroacetaldehyde

HCID 6576
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
79-02-7
표준 SMILES
O=CC(Cl)Cl
InChIKey
NWQWQKUXRJYXFH-UHFFFAOYSA-N
분자식
C2H2Cl2O
평균 분자량
112.94 g/mol
단동위원소 질량
111.94827004

개요

Dichloroacetaldehyde is a colorless liquid with a penetrating pungent odor. (NTP, 1992)

이름 및 식별자

우선 이름
Dichloroacetaldehyde
IUPAC
2,2-dichloroacetaldehyde
현지명
디클로로아세탈디히드
영어명
DICHLOROACETALDEHYDE
분자식
C2H2Cl2O
분자량
112.94

이름 및 동의어

DICHLOROACETALDEHYDE2,2-Dichloroacetaldehyde79-02-7alpha,alpha-Dichloroacetaldehyde9GT3DHH725NSC-5207DTXSID3021560RefChem:133032DTXCID901560201-169-5Acetaldehyde, dichloro-Acetaldehyde, 2,2-dichloro-
이름 더 보기
디클로로아세탈디히드chloroaldehydeDichloroethanal2,2-DichloroethanalDichloroacetaldehyddichloro-2,2 acetaldehyde2,2-dichloro-acetaldehydeAcetaldehyde,2,2-dichloro-
CHCl2CHO.alpha.,.alpha.-DichloroacetaldehydeCCRIS 5387HSDB 5226NSC 5207EINECS 201-169-5BRN 1739030UNII-9GT3DHH725

데이터베이스 식별자

CAS
79-02-7
PubChem CID
6576
DTXSID
DTXSID3021560
ChEBI
CHEBI:34214
UNII
9GT3DHH725
EC Number
201-169-5
Nikkaji
J35.925D

물성

구조 계산 물성

XLogP
1.1
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
5
형식 전하
0
복잡도
34.6

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Aldehydes
SpringerMaterials PropertiesOptical coefficient
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
OdorPENETRATING PUNGENT ODOR
Density · 3건

1.436 at 77 °F (NTP, 1992) - Denser than water; will sink

1.436 @ 25 °C

Density: 1.4113 g/ cu cm @ 25 °C

Color/FormCOLORLESS LIQ
Solubility · 2건

SOL IN ALC

Soluble in water and common organic solvents.

Flash Point · 2건

140 °F (NTP, 1992)

60 °C CC

Boiling Point · 2건

190 °F at 760 mmHg (NTP, 1992)

89.2 °C

DecompositionWhen heated to decomp it emits toxic fumes of /hydrogen chloride/.
Melting Point

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Danger

H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationChemical: Acetaldehyde, dichloro-
DOT LabelFlammable Liquid
Fire HazardsThis compound is combustible. (NTP, 1992)
Fire Potential · 2건

MODERATE FIRE HAZARD

Combustible

Health HazardsSYMPTOMS: Symptoms of exposure to this compound include local irritation of eyes, nose, and mucous membranes.
Hazards SummaryA strong skin irritant; [Hawley] Highly flammable and polymerizable; An eye, nose, and mucous membrane irritant; [CAMEO]
Reactive GroupAldehydes
Special ReportsRamel C et al; An Evaluation of the Genetic Toxicity of Dichlorvos; Mutat Res 76 (3): 297-309 (1980)
Reactivity AlertsHighly Flammable

화학 및 산업

약리 정보

Metabolism/Metabolites · 5건

DICHLOROACETALDEHYDE IS A PRESUMED METABOLITE OF THE INSECTICIDES, DICHLORVOS & TRICHLORFON.

Mice were injected with dichloroacetaldehyde hydrate (8 mg, ipr). Analysis of the 24 hr urinary metabolites did not reveal any chlorinated compounds apart from traces of dichloroacetic acid. This acid was present as 1% of the applied dose.

In mammals, chloroacetaldehydes are rapidly reduced to chloroethanols and/or oxidized to chloroacetic acids. /Chloroacetaldehydes/

Dichloroacetaldehyde is a metabolite of vinylidene chloride.

cis- and trans-1,2-Dichloroethylene are metabolized, in part, to dichloroacetaldehyde.

용도 및 제조

Uses · 5건

Used to make insecticides and plastics; A presumed metabolic product from dichlorvos and trichlorfon; A waste product in pulp bleaching; [HSDB]

Pulp and Paper Processing [Category: Industry]

MFR OF INSECTICIDES

Used in the manufacture of plastics.

The most important current use of dichloroacetaldehyde and its acetals is in the synthesis of the diuretic trichlormethiazid and the cytostic mitotane 1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane.

ImpuritiesCrude product contained: 4% CCl3CHO, 1% ClCH2CHO /From table/
U.S. ProductionIn 1977, the estimated US production of dichloroacetaldehyde was between 10 million and 50 million lb. /From table/
Methods of Manufacturing · 3건

By chlorination of acetaldehyde or paraldehyde /a trimer of acetaldehyde/ in the presence of a chlorination catalyst with subsequent distillation.

Reaction of acetaldehyde with chlorine at 70-80 °C

The most important industrial production process is the chlorination of acetaldehyde or paraldehyde. Hypochlorination of 1,2-dichloroethylene yields pure dichloroacetaldehyde.

Formulations/Preparations

관련 반응

2건
반응 기록 만들기
HRID 194663 반응식
HRID 194663반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 352061 반응식
HRID 352061반응물로uspto-grants-2004_06

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
· 2건

-58 °F (NTP, 1992)

-37.6 to -37.4 °C

Vapor Density3.9 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

물리화학적 성질

녹는점
-50.15 °C · -50.15°C
끓는 점
90.55 °C · 90.55°C
밀도
1.433 · 1.4330
굴절률
1.453 · 1.4530 (estimate)
Henry's Law Constant
4.7 · 4.7×10-1 mol/(m3Pa) at 25℃, Wang et al. (2017)
EPA
Dichloroacetaldehyde (79-02-7)

화학적 성질

Dichloroacetaldehyde [79-02-7], 2,2-dichloroethanal, CHCl2CHO, Mr112.94, was first obtained in 1868 by F. Paterno by distillation of dichlorodiethyl acetal [619-33-0], CHCl2CH(OC2H5 )2, with sulfuric acid.

Reactivity ProfileDICHLOROACETALDEHYDE polymerizes on standing or in the presence of acid. This compound reacts with acids, oxidizers. (NTP, 1992)
Air and Water ReactionsHighly flammable.
Hazard Classes and CategoriesAcute Tox. 3 (50%)

안전 및 보호

Fire Fighting · 1건

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

First Aid · 1건

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.

Fire Fighting ProceduresTo fight fire, use water, foam, carbon dioxide, dry chemical.
Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear an impervious full-body suit equipped with an air line respirator or a self-contained breathing apparatus.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.3(SRC), determined from a structure estimation method(2), indicates that dichloroacetaldehyde is expected to have very high mobility in soil(SRC). Volatilization of dichloroacetaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.42X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of dichloroacetaldehyde from dry soil surfaces may exist(SRC) based upon its vapor pressure of 55.4 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.3(SRC), determined from a structure estimation method(2), indicates that dichloroacetaldehyde would not be expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.42X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 4.7 and 38 days, respectively(SRC), using an estimation method(3). According to a classification scheme(5), an estimated BCF of 3.2(3,SRC), from an estimated log Kow(6,SRC) suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichloroacetaldehyde, which has a vapor pressure of 55.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dichloroacetaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is 7.0 days(SRC) from its rate constant of 2.3X10-12 cu cm/molecule-sec(3).

Effluent ConcentrationsDichloroacetaldehyde is produced in pulp mill bleaching operations and has been identified in pulp mill effluents(1).
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dichloroacetaldehyde can be estimated to be 4.3(SRC). According to a classification scheme(2), this estimated Koc value suggests that dichloroacetaldehyde is expected to have very high mobility in soil.

Human Toxicity ExcerptsTOXIC BY INGESTION & INHALATION ...
Artificial Pollution Sources · 2건

If chloroacetaldehydes are released during manufacture or use, they are probably released as air emissions and in discharged water. /Di- and tri-chloroacetaldehydes/

Dichloroacetaldehyde's production and use as a chemical intermediate(1) and its formation during the pulp bleaching process(2) may result in its release to the environment through various waste streams(SRC).

Environmental Bioconcentration · 1건

An estimated BCF of 3.2 was calculated for dichloroacetaldehyde(SRC), using an estimated log Kow of 0.27(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1건

The Henry's Law constant for dichloroacetaldehyde is estimated as 8.42X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dichloroacetaldehyde is expected to volatilize from water surfaces(2). 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 4.7 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 38 days(SRC). Dichloroacetaldehyde's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of dichloroacetaldehyde from dry soil surfaces may exist(SRC) based upon its vapor pressure of 55.4 mm Hg at 25 °C(3).

Non-Human Toxicity Excerpts · 4건

DICHLOROACETALDEHYDE, A PRESUMED METABOLITE OF DICHLORVOS & TRICHLORFON, IS MUTAGENIC IN SALMONELLA/MICROSOME TEST. ITS MUTAGENIC POTENCY IS HIGHER THAN DICHLORVOS. THE BACTERIAL MUTAGENICITY TEST MAY ONLY (OR MAINLY) DETECT EFFECT OF METHYLATION BY DICHLORVOS.

DICHLOROACETALDEHYDE SHOWS IN DOMINANT LETHAL TEST IN MICE AT EQUIMOLAR DOSAGE (1.6 MMOL/KG) A MUTAGENIC ACTIVITY COMPARABLE WITH THAT OF TRICHLORFON. IT CANNOT BE RULED OUT THAT THE GENETIC EFFECTS OF THIS PESTICIDE MAY BE DUE TO ACTION OF ITS DEGRADATION PRODUCTS.

2,2-DICHLOROACETALDEHYDE WAS WEAKLY MUTAGENIC IN SALMONELLA TYPHIMURIUM TA100 WITH OR WITHOUT S-9 MIX.

Dichloroacetaldehyde was negative for unscheduled DNA synthesis in human epithelial-like cells whereas both dichlorvos and trichlorfon showed a dose-response effect.

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of dichloroacetaldehyde with photochemically-produced hydroxyl radicals is 2.3X10+12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of 7.0 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). Dichloroacetaldehyde contains an alkyl chloride group which is potentially hydrolyzable(2). No information is available on its hydrolysis rate. Dichloroacetaldehyde is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum.

Probable Routes of Human ExposureDichloroacetaldehyde is toxic by ingestion or inhalation.
Environmental Fate/Exposure Summary · 1건

Dichloroacetaldehyde's production and use as a chemical intermediate and its formation during the pulp bleaching process may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 55.4 mm Hg at 25 °C indicates dichloroacetaldehyde will exist solely as a vapor in the ambient atmosphere. Vapor-phase dichloroacetaldehyde will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is 7.0 days. If released to soil, dichloroacetaldehyde is expected to have very high mobility based upon an estimated Koc of 4.3. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 8.42X10-6 atm-cu m/mole. Dichloroacetaldehyde may potentially volatilize from dry soil surfaces based upon its estimated vapor pressure of 59 mm Hg at 25 °C. If released into water, dichloroacetaldehyde is not expected to adsorb to suspended solids and sediment in the water column based upon its 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 4.7 days and 38 days, respectively. An estimated BCF of 3.2 suggests that the potential for bioconcentration in aquatic organisms is low. Occupational exposure to dichloroacetaldehyde may occur through inhalation and dermal contact with this compound at workplaces where dichloroacetaldehyde is produced or used. (SRC)

안전 데이터

tsca
TSCA listed
ridadr
1992
포장분류
III
위험 등급
3.2
유해 물질 데이터
79-02-7(Hazardous Substances Data)
Solid hydrate (minimum 82% anhydrous product); aqueous solution (minimum 65% anhydrous product)
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information · 2건

Acetaldehyde, 2,2-dichloro-: ACTIVE

High yields are obtained in the chlorination of acetaldehyde or paraldehyde in the presence of antimony trichloride (83% yield) or phosphorous acid (>90%yield)

응용 분야

일반 설명Colorless liquid with a penetrating pungent odor.

상·하류 제품 정보

상류 원료

파라알데히드

하류 제품

비스(디에틸아미노)인산염N-(2,2-디클로로-1-히드록시에틸)-4-플루오로벤즈아미드N-(2,2-디클로로-1-히드록시에틸)-4-플루오로벤젠아세트아미드

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