79-03-8 Usage
Chemical Properties
Propionyl chloride is a colorless to light yellow, volatile, and readily flammable liquid, whose vapors hydrolyze in moist air. It is corrosive, lachrymatory, and has a strongly pungent odor. With water and lower alcohols it reacts vigorously under solvolysis to give the acid or ester. It is used for the introduction of the propionyl group and for the synthesis of propionate esters because of its high reactivity.
Uses
Propionyl chloride is used as an intermediate in the production of agrochemicals and pharmaceuticals. It serves as an intermediate for dyes, textile auxiliaries and peroxide compounds. It acts as a crop protecting agent.
Preparation
Propionyl chloride is synthesized by reacting propionic acid with phosphorus trichloride at 40-50°C for 1h, cooling, standing, separating and distilling to obtain the product.CH3CH2COOH+PCl3→CH3CH2COCl+HOPCl2Propionyl chloride is produced industrially by treatment of propionic acid with phosgene or thionyl chloride. The reaction occurs at ca. 50°C in the liquid phase in the presence of dialkylformamides. The product is then separated by distillation.CH3CH2CO2H + COCl2 → CH3CH2COCl + HCl + CO2Propionyl chloride can also be obtained by the reaction of propionic acid with PCl5.
Application
Propionyl chloride is used for the introduction of the propionyl group and for the synthesis of propionate esters because of its high reactivity. It is an chemical intermediate in the preparation of various propionic acid derivatives, It can also be used:To convert anisole to 4-methoxypropiophenone and 2-methoxynaphthalene to 1-propio-2-methoxynaphthalene in the presence of Indium(III) chloride (InCl3) impregnated mesoporous Si-MCM-41 catalyst.For chlorination in the presence of sulfuryl chloride and peroxides to form α-chloropropionyl chloride and β-chloropropionyl chloride.In reaction with (hydroxypropyl)cellulose to form the propanoate ester, [(propionyloxy)propyl]cellulose.
General Description
Propionyl chloride appears as a colorless liquid with a pungent odor. Corrosive and very irritating to skin and eyes. Used to make other chemicals.
Air & Water Reactions
Highly flammable. Propionyl chloride reacts vigorously or violently with water to form propionic acid and hydrochloric acid [Merck 11th ed. 1989].
Reactivity Profile
Acid halides, such as Propionyl chloride, are water reactive; some are violently reactive. They are incompatible with strong oxidizing agents, alcohols, amines, and alkali. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Hazard
Strong irritant to skin.
Health Hazard
May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Highlyflammable
Safety Profile
A corrosive irritant to
skin, eyes, and mucous membranes.
Dangerous fire hazard when exposed to heat
or flame; can react vigorously with oxidizing
materials. Reacts with water or steam to
produce toxic and corrosive fumes.
Exothermic reaction with diisopropyl ether
produces much gas. The reaction may be
dangerous if confmed. To fight fire, use
CO2, dry chemical; do not use water. When
heated to decomposition it emits lughly
toxic fumes of Cl-. See also
HYDROCHLORIC ACID.
Check Digit Verification of cas no
The CAS Registry Mumber 79-03-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 79-03:
(4*7)+(3*9)+(2*0)+(1*3)=58
58 % 10 = 8
So 79-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H5ClO/c1-2-3(4)5/h2H2,1H3
79-03-8Relevant articles and documents
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
Synthesis, experimental and theoretical study of novel 2-haloalkyl (-CF2H, -CCl2H, -CF2CF3)-, 3-bromo and bromomethyl substituted chromones
Narváez O, Ena G.,Bonilla V., Pablo M.,Zurita, Daniel A.,Alcívar L., Christian D.,Heredia-Moya, Jorge,Ulic, Sonia E.,Jios, Jorge L.,Piro, Oscar E.,Echeverría, Gustavo A.,Langer, Peter
, (2021/01/12)
A set of seven new chromones with 2-haloalkyl (-CF2H, -CCl2H, -CF2CF3) and 3-bromo and bromomethyl substituents were synthesized. The novel compounds were studied by DFT calculations and characterized by vibrational spectroscopy (IR and Raman) in solid state, and NMR (1H, 13C and 19F) and UV–vis spectroscopy in solution. The crystal structure of 3-dibromomethyl-2-difluoromethyl chromone was determined by X-ray diffraction. Due to extended π-bond delocalization, the organic framework is planar and lies on a crystallographic m-mirror plane. The intermolecular non-covalent interactions of 3-dibromomethyl-2-difluoromethyl chromone, as π?π stacking arrangements, F?H hydrogen bonds and O?Br contacts were evaluated by Hirshfeld surfaces analysis. These intermolecular contacts, which affect the absorption bands location of the involved groups, were also detected in the vibrational spectra.
Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction
Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae
supporting information, p. 23743 - 23749 (2021/10/14)
Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.
