1,2-ジクロロプロパン

1,2-Dichloropropane

HCID 6564CAS 78-87-5

基本情報

標準SMILES
CC(Cl)CCl
InChIKey
KNKRKFALVUDBJE-UHFFFAOYSA-N
分子式
C3H6Cl2
平均分子量
112.98 g/mol
単同位体質量
111.98465555

概要

1,2-Dichloropropane is a colorless, flammable liquid with a chloroform-like odor. It is moderately soluble in water and readily evaporates into air. It does not occur naturally in the environment. 1,2-Dichloropropane production in the United States has declined over the past 20 years. It was used in the past as a soil fumigant, chemical intermediate and industrial solvent and was found in paint strippers, varnishes, and furniture finish removers. Most of these uses were discontinued. Today, almost all of the 1,2-dichloropropane is used as a chemical intermediate to make perchloroethylene and several other related chlorinated chemicals.

名称と識別子

優先名称
1,2-Dichloropropane
IUPAC
1,2-dichloropropane
現地名
1,2-ジクロロプロパン
英語名
1,2-Dichloropropane
分子式
C3H6Cl2
分子量
112.99

名称と別名

1,2-DICHLOROPROPANE78-87-5Propylene dichloridePropylene chloridePropane, 1,2-dichloro-DwuchloropropanBichlorure de propyleneRCRA waste number U083NCI-C55141alpha,beta-DichloropropaneDTXSID0020448ENT 15,406
名称をさらに表示
1,2-ジクロロプロパン水質分析用標準溶液 1,2-ジクロロプロパン (1mg/mL メタノール溶液)塩化プロピレン2,3-ジクロロプロパンプロピレンクロリド二塩化プロピレン1,2-ジクロロプロパン標準品1,2-ジクロロプロパン標準原液二塩化プロピレン標準品1,2ジクロロプロパン1,2-ジクロロプロパン (1mg/mLメタノール溶液) [水質分析用]プロピレンジクロリド1,2‐ジクロロプロパン1,2‐ジクロロプロパン CRM4038‐A1,2‐ジクロロプロパン標準品1,2‐ジクロロプロパン標準原液1,2-ジクロロプロパン STANDARD1,2-ジクロロプロパン Standard, 0.2 mg/mL in MeOH1,2-ジクロロプロパン Standard, 100 µg/mL in MeOH1,2-ジクロロプロパン Standard, 1000 µg/mL in MeOHDichloropropane1,2-DCP1,2-DichlorpropanDichloropropanesR270daent15,406CH3CHClCH2Cl
alpha,beta-Propylene dichlorideRRZ023OFWLNSC-1237DTXCID60448CHEBI:142468Dichloro-1,2-propaneRefChem:71870201-152-2

データベース識別子

CAS
78-87-5
PubChem CID
6564
DTXSID
DTXSID0020448
ChEMBL
CHEMBL44641
ChEBI
CHEBI:82163
UNII
RRZ023OFWL
EC Number
201-152-2
Nikkaji
J1.486I

物性

構造計算による物性

XLogP
1.8
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
1
重原子数
5

実験および物理化学的性質

Chemical Classes · 2 件

Hazardous Air Pollutants (HAPs)

Flammable agents - 3rd degree

SolventsSolvents -> Chlorinated Aliphatics
Pesticides · 4 件

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Volatile Organic Compound (VOC) (Pesticide/Volatile Organic Compound (VOC))

LogP · 2 件

log Kow = 1.98

2.02 (calculated)

Odor · 2 件

Sweet

Chloroform-like odor.

Density · 6 件

1.158 at 68 °F (USCG, 1999) - Denser than water; will sink

1.159 @ 25 °C/25 °C

Relative density (water = 1): 1.16

1.16

1.159 @25 °C

1.16

物理化学的性質

融点
100 °C · −100 °C(lit.)
沸点
95 · 95-96 °C(lit.)
比重(密度)
1.156 g/mL · 1.156 g/mL at 25 °C(lit.)
蒸気密度
3.89 · 3.89 (vs air)
蒸気圧
40 mm · 40 mm Hg ( 19.4 °C)
屈折率
20 · n20/D 1.439(lit.)

化学的性質

化学的特性colourless liquid

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P316, P317, P318, P321, P330, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Propane, 1,2-dichloro-

Hazard Traits - Carcinogenicity; Neurotoxicity; Respiratory Toxicity

Propane, 1,2-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 1,2-dichloro- 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)

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

2002/2076

Status: Active Update: 05-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/13586

Other Safety InformationIMAP assessments - Propane, 1,2-dichloro-: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 件

Special Hazards of Combustion Products: Toxic and irritating gases may be generated. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Heating will cause rise in pressure with risk of bursting. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire Potential · 2 件

DESPITE LOW FLASH POINT IT DOES NOT CATCH FIRE READILY IN INDUSTRIAL APPLICATIONS.

A flammable liquid and bery dangerous fire hazard when exposed to heat or flame.

Health Hazards · 2 件

Contact with skin or eyes may cause irriation. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Use powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap. Refer for medical attention .

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

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

Accidental Release Measures · 2 件

· 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 · 3 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.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Toxicological InformationCDC-ATSDR Toxicological Profile
Cancer Sites[in animals: liver & mammary gland tumors]
Interactions · 2 件

MALE RATS EXPOSED 4 HR TO VARIOUS CONCN TO TETRACHLOROETHYLENE SINGLY & IN COMBINATION WITH 1,2-DICHLOROPROPANE SHOWED MARKEDLY ELEVATED GLUTAMIC OXALACETIC TRANSAMINASE, GLUTAMIC PYRUVIC TRANSAMINASE & ORNITHINE CARBAMYL TRANSFERASE.

Weanling Wistar rats, fed for several weeks on low protein choline-deficient diets, were more susceptible to the effects of inhalation of 4660 mg 1,2-dichloropropane/cu m than rats on a control diet. This increased susceptibility could be corrected by dietary supplements of 1-methionine or 1-cysteine plus choline chloride.

Target Organs · 3 件

Developmental (effects while organs are developing), Hematological (Blood Forming), Hepatic (Liver), Neurological (Nervous System), Respiratory (From the Nose to the Lungs)

Respiratory

Eyes, skin, respiratory system, liver, kidneys, central nervous system

Ecotoxicity Values · 5 件

TLm Shrimp > 100 ppm/48 hr /Conditions of bioassay not specified/

LC50 Poecilia reticulata (guppy) 116 ppm/7 days /Conditions of bioassay not specified/

LC50 Lepomis macrochirus 320 ppm/96 hr; In fresh water at 23 °C, mild aeration applied after 24 hr

LC50 Menidia beryllina 240 ppm/96 hr; In synthetic seawater at 23 °C, mild aeration applied after 24 hr

For more Ecotoxicity Values (Complete) data for 1,2-DICHLOROPROPANE (8 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 47(2), indicates that 1,2-dichloropropane is expected to have very high mobility in soil(SRC). Volatilization of 1,2-dichloropropane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.82X10-3 atm-cu m/mole(3). The potential for volatilization of 1,2-dichloropropane from dry soil surfaces may exist(SRC) based upon a vapor pressure of 53.3 mm Hg(4). Biodegradation is not expected to be an important environmental fate process in soil given a BOD of 0% theoretical using the MITI test(5). In a closed system using fresh soil at 15 °C, a mean half-life of 52 days was measured for 1,2-dichloropropane(6).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 47(2), indicates that 1,2-dichloropropane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3), based upon a Henry's Law constant of 2.82X10-3 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hrs and 4 days, respectively(SRC). The hydrolytic half-life of 1,2-dichloropropane is expected to be 6 months to several years(5). According to a classification scheme(6), a BCF range of 0.5-6.9(7), suggests bioconcentration in aquatic organisms is low(SRC). Biodegradation is not expected to be an important environmental fate process in water given a 0% theoretical BOD using the MITI test(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-dichloropropane, which has a vapor pressure of 53.3 mm Hg at 25 deg(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2-dichloropropane 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 36 days(SRC), calculated from its rate constant of 4.42X10-13 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Vapor-phase photolysis under simulated sunlight did not occur after prolonged exposure(4).

法規制情報

RCRA Requirements · 1 件

U083; As stipulated in 40 CFR 261.33, when propylene dichloride, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 3 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Dichloropropane is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

Manufacturers and processors of 1,2-dichloropropane are required to conduct (1) Health effects testing incl (a) neurotoxicity testing, (b) mutagenic effects studies, (c) developmental toxicity testing, and (d) pharmacokinetic studies; (2) Environmental effects testing incl (a) mysid acute and chronic toxicity tests, (b) algal acute toxicity testing and (c) daphnid chronic toxicity testing under TSCA section 4.

FIFRA Requirements · 1 件

Propylene dichloride is exempted from the requirement of a tolerance when used as a solvent for formulations used before crop emerges from soil in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.

Atmospheric Standards · 2 件

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. Propylene dichloride is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 1,2-Dichloropropane is included on this list.

CERCLA Reportable Quantities · 1 件

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 1,000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 件

1,2-Dichloropropane 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.

安全データ

wgk
3
IDLA
400 ppm
tsca
TSCA listed
rtecs
TX9625000
ridadr
UN 1279
毒性
LD50 orally in rats: 1.19 ml/kg (Smyth)

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

... 1,2-DICHLOROPROPANE ... IS PARTLY METABOLIZED TO CO2, /UNCHANGED/ 1,2-DICHLOROPROPANE AS WELL AS CO2 METABOLIZED 1,2-DICHLOROPROPANE ARE EXCRETED /IN EXPIRED AIR/.

It has been shown that rat liver microsomes in vitro are capable of metabolizing 1,2-dichloropropane.

The metabolism of 1,2-dichloropropane and its proposed intermediate metabolite 1-chloro-2-hydroxypropane were studied. Sprague-Dawley rats received labeled dichloropropane in ip doses of 100 mg/kg, or by continuous oral dosing at 20 mg/kg per day for four days, while labeled 1-chloro-2-hydroxypropane was administered via ip injections at doses of 100 mg/kg. Urine was collected without fecal contamination for analysis via thin layer chromatography. During in vitro studies, a reaction was carried out in an oxidizing system using 1,2-dichloropropane as the substrate. ... The major urinary metabolite of 1,2-dichloropropane was N-acetyl-S-(hydroxypropyl)cysteine, with 2 minor metabolites, beta-chlorolactate and N-acetyl-S-(2,3-dihydroxypropyl)cysteine. Aside from N-acetyl-S-(2-hydroxypropyl)cysteine, a known urinary metabolite of 1-chloro-2-hydroxypropane, beta-chloroacetaldehyde and beta-chlorolactate were also identified as urinary 1-chloro-2-hydroxypropane metabolites ... /It was/ concluded that 1,2-dichloropropane oxidation to 1-chloro-2-hydroxypropane, ultimately resulting in the production of N-acetyl-S-(2-hydroxypropyl)cysteine, is suggested as the pathway of 1,2-dichloropropane metabolism in rats. The major detoxicating pathway of 1-chloro-2-hydroxypropane is epoxidation to 1,2-epoxypropane, which can either conjugate with glutathione or be hydrolyzed to propane-1,2-diol.

1,1-Dichloropropane & 1,2-dichloropropane are enzymatically dechlorinated by an enzyme located in hepatic microsomes. This system requires reduced nicotinamide adenine dinucleotide phosphate & oxygen, & is inducible by phenobarbital & benzpyrene, but not by methylcholanthrene. The optimum pH of the system is 8.2.

For more Metabolism/Metabolites (Complete) data for 1,2-DICHLOROPROPANE (6 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 3 件

Rats receiving single oral doses of 1,2-dichloro(1-(14)C)propane excreted about 50% in the urine & 5% in feces in 24 hr. There was little further excretion over the next 72 hr. A total of 19% of the dose was excreted as (14)CO2 & 23% as other volatile substances. At 96 hr, 5% remained in the carcass.

Male & female Fischer 344 rats were either exposed to atmospheres of 5, 50 or 100 ppm (23, 230 or 460 mg/cu m) of singly labeled 1,2-dichloro((14)C))propane for a 6 hr period or dosed orally once with 1 or 100 mg/kg bw or on 7 consecutive days with 1 mg/kg bw. During inhalation exposure, maximum blood concns were reached after 2 hr, the values being approx 0.06, 0.9 & 4.0 ug/g blood, respectively. Once exposure stopped, 1,2-dichloropropane was rapidly eliminated from blood. Analysis of expired air provided evidence for saturation of metab, the proportion of expired 1,2-dichloro((14)C)propane increasing with dose. For both gavage & inhalation admin, the principal routes of elimination were urine (37-65%) & expired air (18-40%), most of the radioactivity being eliminated within 24 hr, irrespective of the route or sex. Tissues, feces & the cage wash accounted for <11%, about 10% & about 4% of the dose, respectively.

Groups of 5 male Wistar rats (200 g) were admin ip, 0, 10, 25, 50, 100, 250, or 500 mg 1,2-dichloropropane (97%)/kg bw in 0.5 ml corn oil for 5 days (once daily) or for 4 wk (5 days/wk). Urinary mercapturic acid excretion was monitored. A significant incr in mercapturic acid excretion was observed at all dose levels, with no further incr during the treatment: at lower doses, a return to baseline values occurred within 48 hr of the end of the treatment. Mercapturic acid excretion at the end of wk 2, 3, & 4 was significantly lower than that observed at the end of the first wk.

用途と製造

Uses · 6 件

Propylene dichloride is used as a chemical intermediate in the production of chlorinated organic chemicals, as an industrial solvent, in ion exchange manufacture, in toluene diisocyanate production, in photographic film manufacture, for paper coating, and for petroleum catalyst regeneration.

Propylene dichloride is used as a solvent for many different purposes. [ACGIH] Used as a solvent in plastics, resins, fats & oils, metal degreasing, rubber processing, and dry cleaning; Used in past as a soil fumigant; [HSDB] Production of 1,2-dichloropropane in the USA decreased in the early 1980s since it was no longer used in paint strippers, furniture finishes, or as an insecticide. [IARC]

No longer available for agricultural use (insecticide and soil fumigant) and no longer available to consumers in paint strippers, varnish, and furniture finish; [ACGIH]

Metal Degreasing [Category: Clean]

For 1,2-Dichloropropane (USEPA/OPP Pesticide Code: 029002) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Livestock (in DD mixt); solvent in plastics, resins, and metals indust, int in rubber processing

ImpuritiesWATER-O.O5% MAX, OXYGEN COMPOUNDS-0.1% MAX
U.S. Production · 5 件

2023: 100,000,000 - <250,000,000 lb

(1972) 1.85X10+10 G (SALES)

(1975) 3.82X10+10 G

(1980) 3.50X10+10 g

(1988) NO DATA PROVIDED

Consumption Patterns · 1 件

(For agricultural uses) 50% used alone as an insecticide for stored grain; 48% in DD mixture as an insecticide on crops; 2% in DD mixture as an insecticide for livestock and in other agricultural applications (DD mixture consists of 1,3-dichloropropene, 3,3-dichloropropene, 1,2-dichloropropane, 2,3-dichloropropene, and related C3 chlorinated hydrocarbons) (1975) /SRP: D-D no longer in production/

Industry UsesIntermediate
Methods of Manufacturing · 3 件

Chlorination of propylene

From propyl chloride and antimony pentachloride

Action of chlorine on propylene

応用分野 · 5 件

解説1,2-ジクロロプロパン,プロパンの水素原子二つが塩素原子で置換された化合物。クロロホルム様の臭気をもつ。無色の液体。テトラクロロエチレンやトリクロロエチレンなどの原料のほか、金属洗浄剤、有機溶剤として利用される。化学式C3H6Cl2 二塩化プロピレン。

用途金属用洗浄剤,油脂?樹脂?ゴム?ワックス?アスファルト溶剤,ドライクリーニング用溶剤,四塩化炭素?テトラクロロエチレン合成原料

用途油脂の溶剤、ドライクリーニング、殺線虫剤の原料。

使用1,2-Dichloropropane is a byproduct in the production of epichlorohydrin (E582310), an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA cross-links.

一般的な説明Colorless watery liquid with a sweet odor. Sinks in water. Produces an irritating vapor.

調製方法

純化方法Distil the propane from CaH2. It has a limited shelf life. [Beilstein 1 IV 195.]

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関連反応

25 件

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