2-Chloropropionic acid

HCID 11734

Basic information

CAS
28554-00-9
Standard SMILES
CC(Cl)C(=O)O
InChIKey
GAWAYYRQGQZKCR-UHFFFAOYSA-N
Molecular formula
C3H5ClO2
Average molar mass
108.52 g/mol
Monoisotopic mass
107.99780708

Overview

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

Names & identifiers

Preferred name
2-Chloropropionic acid
IUPAC
2-chloropropanoic acid
English name
2-Chloropropionic acid
Molecular formula
C3H5ClO2
Molecular weight
108.52

Names & synonyms

2-Chloropropionic acid2-CHLOROPROPANOIC ACID598-78-7Propanoic acid, 2-chloro-Propionic acid, 2-chloro-alpha-Chloropropionic acidDTXSID0021545alpha-Monochloropropionic acidPropionic acid, alpha-chloro-ADV1WUE1NBNSC-173DTXCID301545
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Organic Acids

Corrosives

LogP0.76
OdorPungent
Density · 5 items

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 items

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

Solubility in water: miscible

Physicochemical properties

Melting point
-12 · -12--14 °C
Boiling point
170 · 170-190 °C(lit.)
Density
1.182 g/mL · 1.182 g/mL at 25 °C(lit.)
vapor pressure
4 mm · 4 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.4345(lit.)
Flash point
215 °F · 215 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 5 items

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 items

Corrosive

Corrosive

Fire Hazards · 4 items

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 items

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

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]

Safety & protection

Fire Fighting · 3 items

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 items

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 items

· 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 items

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).

Toxicology

Environmental Fate · 3 items

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 item

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 items

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 item

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).

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
UE8575000
ridadr
UN 2511
hs_code
29159080

Chemistry & industry

Uses & manufacturing

Uses · 4 items

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
Applications · 4 items

Description2-Chloropropionic acid is a colorless to white crystalline solid or liquid that is denser than water; therefore, can sink and mix with water. It has a slight odor and is the simplest chiral chlorocarboxylic aid.

UsesIntermediate for weed killers.

Uses2-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.

General DescriptionA 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.

Preparation methods

Preparation2-Chloropropionic acid is prepared from diazotization of L-alanine in hydrochloric acid.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Related reactions

101 records

Compound notes

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