557-98-2

Basic information

• Product Name: 2-Chloropropene
• Synonyms: 1-Methylvinylchloride;1-propene,2-chloro-;2-Chlor-1-propen;2-chloro-1-propen;2-chloro-propen;2-Chloropropene-1;beta-Chloropropene;beta-Chloropropylene
• CAS NO: 557-98-2
• Molecular Formula: C₃H₅Cl
• Molecular Weight: 76.52
• EINECS: 209-187-5
• Mol File: 557-98-2.mol

Chemical Properties

• Melting Point: -138 °C
• Boiling Point: 23 °C
• Flash Point: -20°C
• Appearance: /
• Density: 0.91
• Vapor Pressure: 828mmHg at 25°C
• Refractive Index: n20/D 1.395(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 1361376
• CAS DataBase Reference: 2-Chloropropene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropropene(557-98-2)
• EPA Substance Registry System: 2-Chloropropene(557-98-2)

Safety Data

• Hazard Codes: F+,Xi
• Statements: 12-36/37
• Safety Statements: 16-26-36
• RIDADR: UN 2456 3/PG 1
• WGK Germany: 3
• RTECS: UC7200000
• F: 10-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: I
• Hazardous Substances Data: 557-98-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
2-Chloropropene is used as a reagent in the measurement of photoionization cross sections of allyl and 2-propenyl radicals to form C3H5+. This process is carried out using tunable vacuum ultraviolet synchrotron radiation coupled with photofragment translational spectroscopy, which is essential for understanding the behavior of these radicals in various chemical reactions.
Used in the Chemical Industry:
2-Chloropropene is utilized as an intermediate in the production of various chemicals, such as acrylic acid, acrylonitrile, and other polymers. Its versatility as a building block for different chemical compounds makes it a valuable asset in the chemical industry.
Used in the Pharmaceutical Industry:
Due to its reactive nature, 2-Chloropropene can be used as a starting material for the synthesis of various pharmaceutical compounds. Its ability to form different chemical bonds with other molecules allows for the creation of a wide range of drugs with potential therapeutic applications.
Used in the Production of Agrochemicals:
2-Chloropropene is also employed in the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties make it suitable for the development of effective and targeted solutions for controlling pests and weeds in agriculture.

Preparation

1,2-Propadiene adds hydrogen chloride to yield 2-chloropropene. One early synthesis involves dehydrohalogenation of 1,2-dichloropropane with potassium hydroxide.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Halogenated aliphatic compounds, such as 2-Chloropropene, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Low molecular weight haloalkenes are highly flammable, peroxidizable and may polymerize violently. They may react violently with aluminum. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn 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.

Safety Profile

Mildly toxic by inhalation. Mutation data reported. Very dangerous fire hazard when exposed to heat, flame, sparks, or powerful oxidizers. To fight fire, use water, spray, mist, fog, dry chemical, alcohol foam. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.

InChI:InChI=1/C3H5Cl/c1-3(2)4/h1H2,2H3

Upstream product

• 3175-23-3 1,2,2-trichloropropane 
• 26198-63-0 1,2-Dichloropropane 
• 594-20-7 2,2-dichloropropane 
• 67-64-1 acetone 
• 74-99-7 prop-1-yne 
• 594-71-8 2-chloro-2-nitro-propane 
• 5447-97-2 2-bromo-2-nitropropane 
• 78604-24-7 1-(p-cyanophenyl)3-(2-chloropropyl)triazene 
• 187737-37-7 propene 
• 123-75-1 pyrrolidine 
• 110-89-4 piperidine 
• 110-91-8 morpholine 
• 111-92-2 dibutylamine 
• 109-89-7 diethylamine 

Downstream Products

• 856191-67-8 formaldehyde-[bis-(3,3-dichloro-butyl)-acetal] 
• 106-99-0 buta-1,3-diene 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 78-79-5 isoprene 
• 507-20-0 tertiary butyl chloride 
• 74-99-7 prop-1-yne 
• 926-66-9 2-ethoxyprop-1-ene 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 3175-23-3 1,2,2-trichloropropane 
• 3017-96-7 1-bromo-2-chloropropane 
• 2310-98-7 2-bromo-2-chloropropane 
• 420-44-0 2-chloro-2-fluoropropane 
• 594-20-7 2,2-dichloropropane 
• 67-64-1 acetone 

Relevant articles and documents

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.

2, 3, 3, 3-tetrafluoropropene method for the synthesis of

The invention discloses a method for synthesizing 2,3,3,3-tetrafluoropropene and belongs to the field of organic synthesis. The method comprises the following steps: (1) preparing 2-chloropropene from 1,2-dichloropropane, which serves as a raw material, through continuous catalytic cracking by adopting a fixed bed in the presence of beta-zeolite, which serves as a catalyst; (2) selectively chlorinating 2-chloropropene with chlorine gas under the catalysis of ferric chloride, so as to prepare 2,3,3,3-tetrachloropropylene; and (3) fluorating 2,3,3,3-tetrachloropropylene with hydrofluoric acid under the catalysis of SbF3 or SbF5, thereby obtaining 2,3,3,3-tetrafluoropropene. The synthesis route has the advantages that the source of raw materials is wide, the cost is low, and the product yield is high; and the obtained product can serve as an automotive air conditioning refrigerant and has a positive significance in reduction of greenhouse effect.

Method for synthetizing isopropenyl boric acid ester

The invention discloses a method for synthetizing isopropenyl boric acid ester. Acetone is used as a raw material and subjected to a reaction with hydrazine hydrate to generate hydrazone, then, isopropenyl halogen is generated at the existence of NXS and organic base and then subjected to a one-pot reaction with metallic lithium and bi(disopropylamine) boron halide, diol and a polymerization inhibitor are added for a backflow reaction to obtain isopropenyl boronic acid ester, and the yield is 65-69%,. The method is easy and convenient to implement, purification is convenient, the yield is high, no ultralow temperature reaction is needed, and the method is suitable for industrial enlarged production.

Aluminum oxide-induced gas-phase ring-opening in methyl substituted gem-difluorocyclopropanes, leading to 2-fluorobuta-1,3-dienes and vinylacetylenes

A gas-phase pyrolysis of methyl-substituted gem-difluorocyclopropanes in a flow-tube reactor in the presence of Al2O3 at 185 - 250 °C gives 2-fluorobuta-1,3-dienes and vinylacetylenes.

PROCESS FOR THE PRODUCTION OF CHLORINATED PROPANES AND/OR PROPENES

Processes for the production of chlorinated propenes are provided wherein the feedstream comprises 1,2-dichlropropane. The present processes make use of at least one reactor twice, i.e., at least two reactions occur in the same reactor. Cost and time savings are thus provided. Additional savings can be achieved by conducting more than two chlorination reactions, or all chlorination reactions, in one chlorination reactor, and/or by conducting more than two dehydrochlorination reactions, or all dehydrochlorination reactions, within a single dehydrochlorination reactor.

Study of the catalytic dehydrochlorination of 1,2-dichloropropane

Catalytic dehydrochlorination of 1,2-dichloropropane in the presence of γ-Al2O3, CaX, and haydite was studied. A relationship between the catalytic activity and acidity of the catalysts under study was revealed.

Method for preparing a halogenated olefin

Process for the preparation of a halogenated olefin Process for the preparation of a halogenated olefin by reaction of an alkyne and/or of an allene compound with a hydrogen halide in a liquid medium comprising at least one hydrohalogenation catalyst comprising at least one palladium compound.

Flash vacuum pyrolysis over magnesium. Part 1 - Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides

Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E, E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

Process for preparation of 2-chloro-1-propene

2-Chloro-1-propene is prepared by catalytic hydrochlorination of methylacetylene and/or of propadiene in a liquid medium containing at least one catalyst chosen from compounds of the metals from group VIIIa and from the lanthanides, and at least one organic solvent capable of dissolving the catalyst.

Dehydrochlorination of 1,2-dichloropropane by CO2 laser-induced breakdown; comparison with thermal elimination

Dehydrochlorination of 1,2-dichloropropane (DCP) was conducted by thermal elimination and CO2 laser-reduced dielectric breakdown, which was induced by focusing the 10.6 μm lines of a CO2 TEA laser. Thermal dehydrochlorination proceeded by a four-centered mechanism at > 425 °C and by a surface-catalyzed radical process at 2000 °C.