3-Chloropropanoic acid

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3-Chloropropanoic acid
3-chloropropionic acid.svg
Identifiers
  • 3-chloropropionic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.214 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C3H5ClO2
Molar mass 108.52 g·mol−1
3D model (JSmol)
Melting point 42 °C (108 °F)
Boiling point 204 °C (399 °F) (decomp.)
  • C(CCl)C(=O)O
  • InChI=1S/C3H5ClO2/c4-2-1-3(5)6/h1-2H2,(H,5,6)
  • Key:QEYMMOKECZBKAC-UHFFFAOYSA-N
   (verify)

3-Chloropropanoic acid (also known as 3-chloropropionic acid or UMB66) is the organic compound with the formula ClCH2CH2CO2H. A white or colorless solid, it is used as a drug and a synthetic intermediate. The compound is produced by the hydrochlorination of acrylic acid. [1] In aqueous solution, it has a pKa value of 4.08. [2]

This compound is used in scientific research. It is structurally related to GHB and binds to the GHB receptor, but has no affinity for GABA receptors. [3] It is also an active ingredient in some herbicide blends. [4] Overdose may cause unconsciousness and/or convulsions. [5] It has been demonstrated that the substance can be broken down by both bacteria and fungi as a means of bioremediation. [6] [4]

Related Research Articles

<span class="mw-page-title-main">Glycine</span> Amino acid

Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable). In the gas phase, it is a molecule with the chemical formula NH2CH2‐COOH. In solution or in the solid, glycine exists as the zwitterion. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (GGU, GGC, GGA, GGG). Glycine is integral to the formation of alpha-helices in secondary protein structure due to the "flexibility" caused by such a small R group. Glycine is also an inhibitory neurotransmitter – interference with its release within the spinal cord (such as during a Clostridium tetani infection) can cause spastic paralysis due to uninhibited muscle contraction.

<i>gamma</i>-Hydroxybutyric acid Chemical compound

gamma-Hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid is a naturally occurring neurotransmitter and a depressant drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas. It acts on the GHB receptor and is a weak agonist at the GABAB receptor. GHB has been used in the medical setting as a general anesthetic and as treatment for cataplexy, narcolepsy, and alcoholism. The substance is also used illicitly for various reasons, including as a performance-enhancing drug, date rape drug, and as a recreational drug.

<span class="mw-page-title-main">Propionic acid</span> Carboxylic acid with chemical formula CH3CH2CO2H

Propionic acid is a naturally occurring carboxylic acid with chemical formula CH
3
CH
2
CO
2
H
. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3
CH
2
CO
2
as well as the salts and esters of propionic acid are known as propionates or propanoates.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. Haloarenes are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

gamma-Butyrolactone Chemical compound

Gamma-butyrolactone (GBL) or γ-butyrolactone is an organic compound with the formula O=CO(CH2)3. It is hygroscopic, colorless, water-miscible liquid with a weak, characteristic odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.

<span class="mw-page-title-main">Cyanuric chloride</span> Chemical compound

Cyanuric chloride is an organic compound with the formula (NCCl)3. This white solid is the chlorinated derivative of 1,3,5-triazine. It is the trimer of cyanogen chloride. Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.

Pyrazole is an organic compound of azole group with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in ortho-substitution. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugate acid 2.49 at 25 °C). Pyrazoles are also a class of compounds that have the ring C3N2 with adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are celecoxib (celebrex) and the anabolic steroid stanozolol.

<span class="mw-page-title-main">Levulinic acid</span> Chemical compound

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels, such as ethyl levulinate.

<span class="mw-page-title-main">Trifluoroacetic acid</span> Chemical compound

Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a haloacetic acid, with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms. It is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, Ka, that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is widely used in organic chemistry for various purposes.

<span class="mw-page-title-main">4-Hydroxybenzoic acid</span> Chemical compound

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

Ruthenium tetroxide is the inorganic compound with the formula RuO4. It is a yellow volatile solid that melts near room temperature. It has the odor of ozone. Samples are typically black due to impurities. The analogous OsO4 is more widely used and better known. It is also the anhydride of hyperruthenic acid (H2RuO5). One of the few solvents in which RuO4 forms stable solutions is CCl4.

<span class="mw-page-title-main">Succinic semialdehyde dehydrogenase deficiency</span> Rare disorder involving deficiency in GABA degradation

Succinic semialdehyde dehydrogenase deficiency (SSADHD) is a rare autosomal recessive disorder of the degradation pathway of the inhibitory neurotransmitter γ-aminobutyric acid, or GABA. The disorder has been identified in approximately 350 families, with a significant proportion being consanguineous families. The first case was identified in 1981 and published in a Dutch clinical chemistry journal that highlighted a number of neurological conditions such as delayed intellectual, motor, speech, and language as the most common manifestations. Later cases reported in the early 1990s began to show that hypotonia, hyporeflexia, seizures, and a nonprogressive ataxia were frequent clinical features as well.

<span class="mw-page-title-main">2-Chloropropionic acid</span> Chemical compound

2-Chloropropionic acid (2-chloropropanoic acid) is the chemical compound with the formula CH3CHClCO2H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer. The conjugate base of 2-chloropropionic acid (CH3CHClCO2), as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.

<span class="mw-page-title-main">Propionic anhydride</span> Chemical compound

Propionic anhydride is an organic compound with the formula (CH3CH2CO)2O. This simple acid anhydride is a colourless liquid. It is a widely used reagent in organic synthesis as well as for producing specialty derivatives of cellulose.

<span class="mw-page-title-main">GHB receptor</span> GHB receptor coding gene in the species Homo sapiens

The γ-hydroxybutyrate (GHB) receptor (GHBR), originally identified as GPR172A, is an excitatory G protein-coupled receptor (GPCR) that binds the neurotransmitter and psychoactive drug γ-hydroxybutyric acid (GHB). As solute carrier family 52 member 2 (SLC52A2), it is also a transporter for riboflavin.

Organoiodine chemistry is the study of the synthesis and properties of organoiodine compounds, or organoiodides, organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature. The thyroxine hormones are organoiodine compounds that are required for health and the reason for government-mandated iodization of salt.

<span class="mw-page-title-main">Fluridone</span> Chemical compound

Fluridone is an organic compound that is used as aquatic herbicide often used to control invasive plants. It is used in the United States to control hydrilla and Eurasian watermilfoil among other species. Fluridone is sold as a solution and as a slow release solid because the herbicide level must be maintained for several weeks. The compound is a colorless solid.

<span class="mw-page-title-main">2,2-Dichloropropionic acid</span> Chemical compound

2,2-Dichloropropionic acid is the organic compound with the formula CH3CCl2CO2H. It is a colorless liquid that freezes near room temperature.

α-Halo carboxylic acids and esters are organic compounds with the respective formulas RCHXCO2H and RCHXCO2R' where R and R' are organic substituents. The X in these compounds is a halide, usually chloride and bromide. These compounds are often used as intermediates in the preparation of more elaborate derivatives. They are often potent alkylating agents. The mono halide derivatives are chiral.

References

  1. Samel U, Kohler W, Gamer AO, Keuser U (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN   978-3527306732.
  2. Dixon SL, Jurs PC (December 1993). "Estimation of p K a for organic oxyacids using calculated atomic charges". Journal of Computational Chemistry. 14 (12): 1460–1467. doi:10.1002/jcc.540141208. ISSN   0192-8651.
  3. Macias AT, Hernandez RJ, Mehta AK, MacKerell AD, Ticku MK, Coop A (April 2004). "3-chloropropanoic acid (UMB66): a ligand for the gamma-hydroxybutyric acid receptor lacking a 4-hydroxyl group". Bioorganic & Medicinal Chemistry. 12 (7): 1643–1647. doi:10.1016/j.bmc.2004.01.025. PMID   15028257.
  4. 1 2 Ng HJ, Roswanira A, Ronald AC, Fahrul H (2005). "Degradation Of Herbicide (3-Chloropropionic Acid) By Bacterial Dehalogenases" (PDF). Proc. KUSTEM 4th Annual Seminar 2005: 586–590. Archived from the original (PDF) on 2016-03-05.
  5. "Chemical Data Sheet for 3-CHLOROPROPIONIC ACID". NOAA.
  6. Edbeib M (2020-04-15). "3-Chloropropionic Acid (3cp) Degradation and Production of Propionic Acid by Newly Isolated Fungus Trichoderma Sp. Mf1". International Journal of Life Sciences and Biotechnology. 3 (1): 41–50. doi:10.38001/ijlsb.677005. ISSN   2651-4621.