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2,2-ジクロロアセトアルデヒド

Dichloroacetaldehyde

HCID 6576
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
79-02-7
標準SMILES
O=CC(Cl)Cl
InChIKey
NWQWQKUXRJYXFH-UHFFFAOYSA-N
分子式
C2H2Cl2O
平均分子量
112.94 g/mol
単同位体質量
111.94827004

概要

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

名称と識別子

優先名称
Dichloroacetaldehyde
IUPAC
2,2-dichloroacetaldehyde
現地名
2,2-ジクロロアセトアルデヒド
英語名
DICHLOROACETALDEHYDE
分子式
C2H2Cl2O
分子量
112.94

名称と別名

DICHLOROACETALDEHYDE2,2-Dichloroacetaldehyde79-02-7alpha,alpha-Dichloroacetaldehyde9GT3DHH725NSC-5207DTXSID3021560RefChem:133032DTXCID901560201-169-5Acetaldehyde, dichloro-Acetaldehyde, 2,2-dichloro-
名称をさらに表示
2,2-ジクロロアセトアルデヒド2,2-ジクロロエタナールジクロロアセトアルデヒドchloroaldehydeDichloroethanal2,2-DichloroethanalDichloroacetaldehyddichloro-2,2 acetaldehyde2,2-dichloro-acetaldehydeAcetaldehyde,2,2-dichloro-
CHCl2CHO.alpha.,.alpha.-DichloroacetaldehydeCCRIS 5387HSDB 5226NSC 5207EINECS 201-169-5BRN 1739030UNII-9GT3DHH725

データベース識別子

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

物性

構造計算による物性

XLogP
1.1
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
1
重原子数
5
形式電荷
0
複雑度
34.6

実験および物理化学的性質

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

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 · 2 件

SOL IN ALC

Soluble in water and common organic solvents.

Flash Point · 2 件

140 °F (NTP, 1992)

60 °C CC

Boiling Point · 2 件

190 °F at 760 mmHg (NTP, 1992)

89.2 °C

DecompositionWhen heated to decomp it emits toxic fumes of /hydrogen chloride/.
Melting Point · 2 件

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

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

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

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

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.

用途と製造

Uses · 5 件

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 · 3 件

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

関連反応

2 件
反応記録を作成
HRID 194663 の反応式
HRID 194663反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 352061 の反応式
HRID 352061反応物としてuspto-grants-2004_06

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Nikkaji
J35.925D

-58 °F (NTP, 1992)

-37.6 to -37.4 °C

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

物理化学的性質

融点
-50.15 °C · -50.15°C
沸点
90.55 °C · 90.55°C
比重(密度)
1.433 · 1.4330
屈折率
1.453 · 1.4530 (estimate)
Henry's Law Constant
4.7 · 4.7×10-1 mol/(m3Pa) at 25℃, Wang et al. (2017)
CAS データベース
79 · 79-02-7
EPAの化学物質情報
Dichloroacetaldehyde (79-02-7)

化学的性質

化学的特性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%)

安全と保護具

Fire Fighting · 1 件

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 · 1 件

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 · 1 件

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 · 1 件

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.

毒性情報

Environmental Fate · 3 件

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 · 1 件

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 · 2 件

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 · 1 件

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 · 1 件

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 · 4 件

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 · 1 件

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 · 1 件

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)

安全データ

tsca
TSCA listed
ridadr
1992
hazard_class
3.2
packing_group
III
有毒物質データの
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 · 2 件

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)

応用分野

一般的な説明Colorless liquid with a penetrating pungent odor.

上流・下流製品情報

上流原料

パラアルデヒド

下流製品

ビス(ジエチルアミノ)クロロホスフィンオキシドN-(2,2-ジクロロ-1-ヒドロキシエチル)-4-フルオロベンズアミドN-(2,2-ジクロロ-1-ヒドロキシエチル)-4-フルオロベンゼンアセトアミド

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