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2-クロロプロピオン酸

2-Chloropropionic acid

HCID 11734
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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
28554-00-9
標準SMILES
CC(Cl)C(=O)O
InChIKey
GAWAYYRQGQZKCR-UHFFFAOYSA-N
分子式
C3H5ClO2
平均分子量
108.52 g/mol
単同位体質量
107.99780708

概要

2-Chloropropionic Acid can cause male reproductive toxicity according to an independent committee of scientific and health experts.

名称と識別子

優先名称
2-Chloropropionic acid
IUPAC
2-chloropropanoic acid
現地名
2-クロロプロピオン酸
英語名
2-Chloropropionic acid
分子式
C3H5ClO2
分子量
108.52

名称と別名

2-Chloropropionic acid2-CHLOROPROPANOIC ACID598-78-7Propanoic acid, 2-chloro-Propionic acid, 2-chloro-alpha-Chloropropionic acidDTXSID0021545alpha-Monochloropropionic acidPropionic acid, alpha-chloro-ADV1WUE1NBNSC-173DTXCID301545
名称をさらに表示
2-クロロプロピオン酸α-クロロプロピオン酸2-クロロプロパン酸アルファークロロプロピオン酸アルファクロロプロピオン酸2-クロロプロピオン酸(α-〃)2‐クロロプロピオン酸(^+)-2-クロロプロピオン酸(^+)-2-クロロプロピオン酸, 97%2-chloropropionic2-Chloropropionoic acid2-chloroproprionic acidNSC-4018062-ChlorpropionsureRARECHEM AL BO 12402-Chloropropionic ac-Chloropropanoicacid2-chloro-propanoicaci
(RS)-2-CHLOROPROPIONIC ACIDRefChem:86533209-952-3R(+)-2-Chloropropionic acid.alpha.-Chloropropionic acidPropionic acid, .alpha.-chloro-Propanoic acid, chloro-.alpha.-Monochloropropionic acid

データベース識別子

CAS
28554-00-9、598-78-7
PubChem CID
11734
DTXSID
DTXSID0021545
ChEMBL
CHEMBL1743205
UNII
ADV1WUE1NB
EC Number
209-952-3
Nikkaji
J481B、J5.220E

物性

構造計算による物性補完中

XLogP
0.8
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
6
形式電荷
0
複雑度
61.8

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Organic Acids

Corrosives

LogP0.76
OdorPungent
Density · 5 件

1.2585 at 68 °F (USCG, 1999) - Denser than water; will sink

1.2585 @ 20 °C/4 °C

1.3 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001

1.2585

Color/FormCRYSTALS
Solubility · 2 件

SOL IN ALL PROP IN WATER, ALC, ETHER; SOL IN ACETONE

Solubility in water: miscible

Flash Point · 4 件

225 °F (USCG, 1999)

225 °F (107 °C) (CLOSED CUP)

106 °C c.c.

225 °F

Boiling Point · 5 件

366 °F at 760 mmHg (USCG, 1999)

187 °C

186 °C

186 °C

366 °F

Melting Point · 2 件

-12.1 °C

-12 °C

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 · 6 件

Danger

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

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

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

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

危険有害性情報

Regulatory Information · 5 件

Chemical: Propanoic acid, 2-chloro-

Hazard Traits - Reproductive Toxicity

Status: Active Update: 28-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5225

2-Chloropropionic acid: 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 - Propanoic acid, 2-chloro-: Human health tier I assessment
DOT Label · 2 件

Corrosive

Corrosive

Fire Hazards · 4 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Special Hazards of Combustion Products: May contain hydrogen chloride and phosgene.

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

化学と産業

用途と製造

Uses · 4 件

Used as an intermediate in agricultural, chemical, and pharmaceutical production; [ACGIH]

INTERMEDIATE FOR WEED KILLERS

CHEM INT FOR DALAPON, SILVEX & MECOPROP HERBICIDES

CHEM INT FOR DICHLORPROP & BENZOYLPROP-ETHYL HERBICIDES

U.S. Production(1981) PROBABLY GREATER THAN 2.27X10+6 G
Methods of ManufacturingREACTION OF PROPANOIC ACID WITH CHLORINE
Household ProductsCosmetics product ingredient: 2-Chloropropionic acid
General Manufacturing InformationPropanoic acid, 2-chloro-: ACTIVE
応用分野 · 3 件

用途医薬、農薬原料

使用2-Chloropropionic acid is used in the preparation of propargyl 2-chloropropionate (PCP), an atom transfer radical polymerization (ATRP) initiator, by the esterification of propargyl alcohol.It can be employed in the synthesis of a biologically active chitin derivative, (1-carboxyethyl) chitosan.It can be treated with o-phenylenediamine phosphate to synthesize benzimidazole derivatives.

一般的な説明A pale liquid with a slight odor. Sinks in and mixes with water. Only aluminum, stainless steel or steel covered with a protective lining or coating may contact the liquid or vapor.

調製方法

純化方法Dry it with P2O5 and fractionally distil it under vacuum. [Beilstein 2 IV 745.]

上流・下流製品情報

上流原料

プロピオン酸

関連反応

101 件
反応記録を作成
HRID 6573 の反応式
HRID 6573反応物としてuspto-grants-2006_08
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HRID 23013反応物としてuspto-grants-2005_02
HRID 23019 の反応式
HRID 23019反応物としてuspto-grants-2005_02
HRID 23020 の反応式
HRID 23020反応物としてuspto-grants-2005_02
HRID 23057 の反応式
HRID 23057反応物としてuspto-grants-2005_02
HRID 65191 の反応式
HRID 65191反応物としてuspto-grants-1986_09
HRID 66268 の反応式
HRID 66268反応物としてuspto-grants-1978_12
HRID 133200 の反応式
HRID 133200反応物としてuspto-grants-2008_06
1 / 13 ページ

化合物ノート

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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
その他の操作
ノートを作成反応を作成見積依頼を出す
Vapor Density
Relative vapor density (air = 1): 3.75
Vapor Pressure · 3 件

1.06 [mmHg]

0.13 torr @ 20 °C

Vapor pressure, kPa at 20 °C: 0.10

Refractive IndexINDEX OF REFRACTION: 1.4380 @ 20 °C/D

物理化学的性質

融点
-12 · -12--14 °C
沸点
170 · 170-190 °C(lit.)
比重(密度)
1.182 g/mL · 1.182 g/mL at 25 °C(lit.)
蒸気圧
4 mm · 4 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.4345(lit.)
闪点
215 °F · 215 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
2 O: · H2O: 可溶
酸解離定数(Pka)
2.96 · 2.96±0.10(Predicted)
外見
clear liquid
色
Colorless to Almost colorless
PH
1 · <1 (200g/l, H2O, 20℃)
水溶解度
溶けやすい
BRN
1720259 · 1720259
Henry's Law Constant
3.8 · 3.8×101 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
安定。強酸化剤、強塩基とは相容れない。
InChI
1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)
InChIKey
GAWAYYRQGQZKCR-UHFFFAOYSA-N
SMILES
CC(Cl)C(O)=O
LogP
0.82 at · 0.82 at 20.5℃
CAS データベース
598 · 598-78-7(CAS DataBase Reference)
NISTの化学物質情報
2 · Propanoic acid, 2-chloro-(598-78-7)
EPAの化学物質情報
2 · 2-Chloropropionic acid (598-78-7)

化学的性質

化学的特性colourless liquid

Harmful if inhaled. Irritating to throat. May cause severe skin and eye burns. Harmful if absorbed through skin. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards SummaryCauses testicular atrophy in rats after high-dose feeding; Corrosive to the skin and eyes; [ACGIH]
DOT ID and Guide2511 153
Reactive Group · 2 件

Acids, Carboxylic

Acids, Carboxylic

EC ClassificationSymbol: C; R: 22-35; S: (1/2)-23-26-28-36-45
UN ClassificationUN Hazard Class: 8; UN Pack Group: III
Reactivity Profile · 2 件

A halogenated organic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

2-CHLOROPROPIONIC ACID is neutralized in exothermic reactions by all bases. Reacts with aqueous solutions containing a chemical base and dissolves if neutralization generates a soluble salt. May react with active metals to form gaseous hydrogen and a metal salt. May corrode or dissolve iron, steel, and aluminum parts and containers. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Reacts with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides to generate flammable and/or toxic gases and heat. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but some heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. May initiate polymerization reactions or catalyze other chemical reactions. Fire produces highly toxic chloride fumes (USCG, 1999).

Chemical Dangers · 1 件

Decomposes on heating. This produces toxic and corrosive fumes including hydrogen chloride. Reacts violently with strong bases and strong oxidants. The substance is a medium strong acid. Attacks many metals. This produces flammable/explosive gas (hydrogen - see ICSC 0001).

安全と保護具

Fire Fighting · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Fire Extinguishing Agents: Small fires: dry chemical, CO2, water spray or foam; large fires: water spray, fog or foam. Water or foam may cause frothing. (USCG, 1999)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately 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. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

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

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

INHALATION: Move to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.

General First Aid:

Safe StorageSeparated from strong bases, strong oxidants and food and feedstuffs.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill Response · 2 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Spillage Disposal · 1 件

Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable plastic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Isolation and Evacuation · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskA harmful contamination of the air will be reached quickly on evaporation of this substance at 20 °C.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: If released to soil, 2-chloropropanoic acid is expected to degrade under both aerobic(1-3) and anaerobic conditions(3). An estimated soil adsorption coefficient 62(4,SRC) obtained from an estimated log octanol/water partition coefficient of 0.76(5) indicates that 2-chloropropanoic acid will display high mobility in soil(6). Its pKa, 2.80(7), indicates that it is essentially completely ionized under environmentally significant pHs of 5-9 and, therefore, adsorption to soil as a result of hydrophobic interactions will only be significant under highly acidic conditions(SRC). Based on an estimated Henry's Law constant of 2.6X10-7 atm-cu m/mole at 25 °C(8) and vapor pressure of 2.1 mm Hg at 25 deg(9), 2-chloropropanoic acid is no expected to volatilize from either moist or dry soil to the atmosphere(SRC).

AQUATIC FATE: If released to water, 2-chloropropanoic acid is expected to degrade under both aerobic(1-3) and anaerobic conditions(3). An estimated bioconcentration factor of 2(4,SRC) obtained from an estimated log octanol/water partition coefficient of 0.76(5) indicates that 2-chloropropanoic acid will not significantly bioconcentrate in fish and aquatic organisms. An estimated soil adsorption coefficient 62(4,5,SRC) indicates that it will not significantly adsorb to sediment and suspended organic matter. Its pKa, 2.80(6), indicates that it is essentially completely ionized under environmentally significant pHs of 5-9. Based on an estimated Henry's Law constant of 2.6X10-7 atm-cu m/mole at 25 °C using a group contribution approach(7), the rate of volatilization of 2-chloropropanoic acid to the atmosphere will be slower then water itself(4).

ATMOSPHERIC FATE: If released to the atmosphere, 2-chloropropanoic acid may undergo oxidation by a gas-phase reaction with photochemically produced hydroxyl radicals. An estimated rate constant for this reaction of 1.06X10-12 cu-cm/molec-sec at 25 °C(1) translates to an atmospheric half-life of 8.3 hrs(SRC) using an average atmospheric hydroxyl radical concn of 5X10+5 molec/cu-cm(2). Its relatively high estimated water solubility of 3 g/L(3) obtained from an estimated log octanol/water partition coefficient of 0.76(4) indicates that 2-chloropropanoic acid may also undergo atmospheric removal by wet deposition process(SRC).

Adverse Effects · 1 件

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Exposure RoutesThe substance can be absorbed into the body by ingestion.
Signs and Symptoms · 4 件

Sore throat. Cough. Burning sensation. Laboured breathing. Shortness of breath.

Redness. Pain. Serious skin burns.

Redness. Pain. Severe deep burns.

Abdominal pain. Burning sensation. Shock or collapse.

Effluent Concentrations2-Chloropropanoic acid was identified but not quantified in the spent chlorination liquor from wood pulp bleaching(1).
Soil Adsorption/Mobility · 1 件

Based on an estimated log octanol/water partition coefficient of 0.76(1), the soil adsorption coefficient for 2-chloropropanoic acid can be estimated to be 62(SRC) using a regression-derived equation(2). The magnitude of this value indicates that it will display high mobility in soil(3). The chemical structure of chlorinated aliphatic acids was described as one that suggests little or no adsorption to a soil colloid(4).

Natural Pollution Sources2-Chloropropanoic acid is of anthropogenic origin, and it is not known to be produced by natural sources. (SRC)
Human Toxicity Excerpts · 1 件

TOXICITY STUDIES INDICATE IT TO BE CORROSIVE TO THE EYE AND SKIN. MILD TO MODERATE SKIN BURNS HAVE BEEN OBSERVED IN WORKERS WITH ACUTE EXPOSURES TO THE LIQ. NO IRRITATION WAS NOTED IN EMPLOYEES EXPOSED TO THE VAPOR AT TWA CONCN UP TO 0.35 PPM, WITH EXCURSIONS TO 1.95 PPM.

Artificial Pollution Sources2-Chloropropanoic acid is used as a synthetic intermediate in the production of weed killers(1). It may be released to the environment as a fugitive emission during its production and use(SRC).
Environmental Biodegradation · 2 件

When 2-chloropropanoic acid was incubated with sewage, 10% degradation (expressed as chlorine released) was observed after 2 days; when the sewage was acclimated to sucrose, 36% degradation occurred in 2 days(1). Using a sewage sludge inocula, 2- chloropropanoic acid underwent essentially complete removal within 30 days under aerobic conditions; under anaerobic conditions 75% removal was observed(2). It was degraded by digester sewage sludge inocula raised on fatty acids(3).

2-Chloropropanoic acid was found to support growth of bacteria isolated from soil (Rhizobium)(1). Pure cultures of Pseudomonas alcaligenes, Agrobacterium, Pseudomonas sp, Nocardia sp, Bacillus sp, as well as fungi and actinomycetes, have been found to degrade 2-chloropropanoic acid(2-8). The major metabolite in the degradation of 2-chloropropanoic acid is glycolate(8).

Environmental Bioconcentration · 1 件

Based on an estimated log octanol/water partition coefficient of 0.76(1), the bioconcentration factor for 2-chloropropanoic acid can be estimated to be 2(SRC) using a regression-derived equation(2). The magnitude of this value indicates that bioconcentration in fish and aquatic organisms will not be a significant process(SRC).

Volatilization from Water/Soil · 1 件

Based on an estimated Henry's Law constant of 2.6X10-7 atm-cu m/mole at 25 °C(1), 2-chloropropanoic acid is not expected to volatilize from water or moist soil to the atmosphere. Volatilization from water will be slower than water itself(2,SRC). An estimated vapor pressure for 2-chloropropanoic acid of 2.1 mm Hg at 25 °C(3) indicates that it may rapidly volatilize from dry soil to the atmosphere(SRC). The pKa of 2-chloropropanoic acid, 2.80(4), indicates that it will be essentially completely ionized under environmentally significant pHs of 5-9(SRC). The ionized form of 2-chloropropanoic acid will not significantly volatilize to the atmosphere(SRC).

安全データ

wgk
1
tsca
TSCA listed
rtecs
UE8575000
ridadr
UN 2511
PRTR法
第一種指定化学物質
hs_code
29159080
risk_code
22-35-21/22
化審法
(2)-1157
安衛法
57,57-2
消防法
危-4-3-III
hazard_code
C
safety_code
23-26-28-36-45-36/37/39-28A
hazard_class
8
packing_group
III
自然発火温度
550°C
環境リスク評価
2-クロロプロピオン酸(598-78-7)
Hazard Classifications
Acute Tox. 4 OralSkin Corr. 1A
ストレージクラス
8A - Combustible corrosive hazardous materials
有毒物質データの
598-78-7(Hazardous Substances Data)
塩素
2-クロロ-1-プロパノール
α-Chloroethyl Phenyl Sulfoxide
α-クロロアクリル酸
2-クロロプロパナール
L-乳酸

下流製品

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