96-19-5

Usage

Uses

Used in Pesticide Industry:
1,2,3-Trichloropropene is used as a soil fumigant for controlling nematodes, insects, and soil-borne diseases in various crops. Its effectiveness in penetrating the soil and targeting pests makes it a valuable tool in agriculture.
Used in Chemical Industry:
1,2,3-Trichloropropene is used as an intermediate in the production of various chemicals, including pharmaceuticals and agrochemicals. Its versatility as a chemical building block contributes to its importance in the chemical industry.
Used in Environmental Applications:
1,2,3-Trichloropropene is used for the remediation of contaminated soil and groundwater. Its ability to break down harmful substances and reduce the spread of pollutants makes it a useful agent in environmental cleanup efforts.

Reactivity Profile

1,2,3-TRICHLOROPROPENE incompatible with strong oxidizing and reducing agents. Incompatible with many amines, nitrides, azo/diazo compounds, with alkali metals, and with epoxides. Reacts with bases. Produces toxic fumes when heated to decomposition. Avoid contact with iron, plastics, and aluminum.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Moderately toxic by ingestion,inhalation, and skin contact. Mutation data reported. Aneye and severe skin irritant. Combustible when exposed toheat, flames (sparks) or powerful oxidizers. To fight fire,use water (as a blanket), spray, mist, dry chemic

InChI:InChI=1/C3H3Cl3/c4-1-3(6)2-5/h1H,2H2/b3-1-

Synthetic route

1,2,2,3-tetrachloropropane (13116-53-5) → 1,2,3-trichloropropene (96-19-5)

Conditions	Yield
With triethylbenzylammonium ethanolate In ethyl acetate	97.7%
With sodium hydroxide
chromium(III) oxide at 350℃; for 2h;
With caustic feed at 93.5 - 120℃;

2,3-Dichloroprop-1-ene (78-88-6) → 1,2,3-trichloropropene (96-19-5) + 1,2,2,3-tetrachloropropane (13116-53-5) + 1,1,2,2,3-pentachloropropane (16714-68-4) + hexachloropropane, hexachlorohexanes, pentachlorohexenes, substituted cyclobutanes C6H8Cl4

Conditions	Yield
With chlorine at 25℃; Product distribution; addition of FeCl3, addition of hydroquinone, periodic or continuous chlorina ion;	A 2% B 94% C 4% D n/a

2-bromo-1,2,3-trichloro-propane (42268-11-1) → 1,2,3-trichloropropene (96-19-5)

Conditions	Yield
With sodium hydroxide
With octanol; sodium octanolate

2,3-Dichloroprop-1-ene (78-88-6) → 1,2,3-trichloropropene (96-19-5) + 1,2,2,3-tetrachloropropane (13116-53-5)

Conditions	Yield
With chlorine; phenol at 20℃; Rate constant; Product distribution; other radical reaction inhibitors, such as o-chlorophenol, ionol; other temp.;
With aluminium trichloride; chlorine In various solvent(s) at 24.85℃; Kinetics; Further Variations:; Temperatures; Reagents;
With chlorine In various solvent(s) at -0.15℃;
With 2,2'-azobis(isobutyronitrile); chlorine In various solvent(s) at 24.85℃;

1,1,2,3-tetrachloropropane (18495-30-2) → 1,2,3-trichloropropene (96-19-5) + 3,3-dichloroallyl chloride (2567-14-8)

Conditions	Yield
With sodium hydroxide; cetylpyridinium bromide at 130℃; for 2h; Title compound not separated from byproducts;

2,3,3,4-tetrachloro-butyric acid + water (7732-18-5) → 1,2,3-trichloropropene (96-19-5)

Conditions	Yield
Destillieren; das Natriumsalz reagiert;

CH2ClCCl2CH2Cl → 1,2,3-trichloropropene (96-19-5)

Conditions	Yield
With potassium carbonate

1,2,2,3-tetrachloropropane (13116-53-5) + ethanolic KOH-solution → 1,2,3-trichloropropene (96-19-5)

sodium salt of/the/ 2.3.3.4-tetrachloro-butyric acid → 1,2,3-trichloropropene (96-19-5)

Conditions	Yield
With water beim Destillieren;

1,1,2,3-tetrachloro-2-fluoropropane (3175-26-6) → 1,2,3-trichloropropene (96-19-5)

Conditions	Yield
FeCl3/C at 200℃;

prop-1-yne (74-99-7) → 1,2,3-trichloropropene (96-19-5) + 1,1,2,2-tetrachloropropane (13116-60-4) + 1,2,2,3-tetrachloropropane (13116-53-5)

Conditions	Yield
With chlorine at 60 - 80℃;

1,2,3-trichloropropene (96-19-5) → 1,1,2,2,3-pentachloropropane (16714-68-4)

Conditions	Yield
With chlorine at 70℃; under 11251.1 Torr; Temperature; Pressure; Flow reactor;	98%
With chlorine im Licht;
With chlorine at 40 - 60℃; for 3.5h;

1,2,3-trichloropropene (96-19-5) + 3-Benzyloxyphenol (3769-41-3) → C16H14Cl2O2

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	91%

8-quinolinol (148-24-3) + 1,2,3-trichloropropene (96-19-5) → 8-((Z)-2,3-Dichloro-allyloxy)-quinoline (84165-40-2)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 4h;	77%

chloroxine (773-76-2) + 1,2,3-trichloropropene (96-19-5) → 5,7-Dichloro-8-((Z)-2,3-dichloro-allyloxy)-quinoline (84165-47-9)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 4h;	57%

1,2,3-trichloropropene (96-19-5) + 2,4-dichlorophenol (120-83-2) → 2,4-Dichloro-1-((Z)-2,3-dichloro-allyloxy)-benzene (84165-56-0)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 30℃; for 5h;	44%

3-phenyl-propionaldehyde (104-53-0) + 1,2,3-trichloropropene (96-19-5) → anti-4,5-dichloro-1-phenyl-5-hexen-3-ol + syn-4,5-dichloro-1-phenyl-5-hexen-3-ol

Conditions	Yield
With sodium iodide; tin(ll) chloride In N,N-dimethyl-formamide at 60℃; for 24h;	A 36% B 28%

1,2,3-trichloropropene (96-19-5) + sodium 4-methylphenoxide (1121-70-6) → 4-methyl-2-(2,3-dichloro-2-propenyl)phenol (106119-03-3)

Conditions	Yield
	20.5%

1,2,3-trichloropropene (96-19-5) + 2-methoxy-phenol (90-05-1) → 1-((Z)-2,3-Dichloro-allyloxy)-2-methoxy-benzene (84165-57-1)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 8h;	16%

1,2,3-trichloropropene (96-19-5) + 2-hydroxynitrobenzene (88-75-5) → 1-((Z)-2,3-Dichloro-allyloxy)-2-nitro-benzene (84165-55-9)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 55℃; for 4h;	10%

1,2,3-trichloropropene (96-19-5) + sodium acetate (127-09-3) → acetic acid-(2,3-dichloro-allyl ester) (57843-57-9)

Conditions	Yield
With ethanol

1,2,3-trichloropropene (96-19-5) + potassium phtalimide (1074-82-4) → N-(2,3-dichloro-allyl)-phthalimide (99866-62-3)

Conditions	Yield
With N,N-dimethyl-formamide

1,2,3-trichloropropene (96-19-5) → 3-bromo-1c,2-dichloro-propene (90466-98-1) + 3-bromo-1t,2-dichloro-propene (879408-79-4)

Conditions	Yield
With acetone; sodium bromide

1,2,3-trichloropropene (96-19-5) → 2,3-dichloro-allyl alcohol (2736-73-4)

Conditions	Yield
With sodium carbonate

carbon disulfide (75-15-0) + N-Demethylchlordimeform (21787-80-4) + 1,2,3-trichloropropene (96-19-5) → {[(Z)-4-Chloro-2-methyl-phenylimino]-methyl}-methyl-dithiocarbamic acid (Z)-2,3-dichloro-allyl ester (52804-94-1)

Conditions	Yield
(i) Et3N, (ii) /BRN= 1633563/; Multistep reaction;

1,2,3-trichloropropene (96-19-5) + C5H13NOPS2(1-)*Na(1+) → C8H16Cl2NOPS2 (34575-15-0)

1,2,3-trichloropropene (96-19-5) + 1,2,2,3-tetrachloropropane (13116-53-5) → 1,1,2,2,3-pentachloropropane (16714-68-4)

Conditions	Yield
With chlorine at 19.9℃; Kinetics; Mechanism; Thermodynamic data; other temperature;

1,2,3-trichloropropene (96-19-5) → di(2,3-dichloroallyl) sulfide (25647-78-3)

Conditions	Yield
With sodium sulfide; tetrabutylammomium bromide In water at 70 - 80℃; for 2h;	68 % Chromat.

1,2,3-trichloropropene (96-19-5) + carbon oxide sulfide (463-58-1) + diisopropylamine (108-18-9) → di-allate (2303-16-4)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide 1.) water, 0-5 deg C, 30 min, 2.) toluene, 20-30 deg C, 2-3 h; Yield given. Multistep reaction;

1,2,3-trichloropropene (96-19-5) + natrium carbonate → 2,3-dichloro-allyl alcohol (2736-73-4)

Upstream product

• 13116-53-5 1,2,2,3-tetrachloropropane 
• 42268-11-1 2-bromo-1,2,3-trichloro-propane 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 18495-30-2 1,1,2,3-tetrachloropropane 
• 7732-18-5 water 
• 3175-26-6 1,1,2,3-tetrachloro-2-fluoropropane 
• 74-99-7 prop-1-yne 
• 2736-73-4 2,3-dichloro-2-propene-l-ol 
• 7782-50-5 chlorine 
• 142-28-9 1,3-Dichloropropane 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 2736-73-4 2,3-Dichlor-2-propen-1-ol 
• 16714-68-4 1,1,2,2,3-pentachloropropane 
• 52804-94-1 {[(Z)-4-Chloro-2-methyl-phenylimino]-methyl}-methyl-dithiocarbamic acid (Z)-2,3-dichloro-allyl ester 
• 106119-03-3 4-methyl-2-(2,3-dichloro-2-propenyl)phenol 
• 84165-57-1 1-((Z)-2,3-Dichloro-allyloxy)-2-methoxy-benzene 
• 2303-16-4 di-allate 
• 84165-56-0 2,4-Dichloro-1-((Z)-2,3-dichloro-allyloxy)-benzene 
• 84165-55-9 1-((Z)-2,3-Dichloro-allyloxy)-2-nitro-benzene 
• 13116-53-5 1,2,2,3-tetrachloropropane 
• 15600-01-8 1,1,2,2,3,3-hexachloropropane 

Relevant academic research and scientific papers

PROCESSES FOR PREPARING PENTACHLOROPROPANE AND TETRACHLOROPROPENE FROM DICHLOROPROPENE

A processes for preparing 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, or a mixture thereof from 1,3-dichloropropene. The process may include a two successive chlorination and dehydrochlorination reactions. In a first chlorination reaction 1,3-dichloropropene is reacted with a chlorination agent to form a first chlorination reaction product including 1,1,2,3-tetrachloropropane. This first chlorination reaction product is reacted with a dehydrochlorination reagent in a first dehydrochlorination reaction to form a first dehydrochlorination reaction product including a trichloropropene. The trichloropropene containing reaction product is reacted with a chlorination agent in a second chlorination reaction to form a second chlorination reaction product including at least one of 1,1,1,2,3-pentachloropropane or 1,1,2,2,3-pentachloropropane. This reaction product is reacted with a dehydrochlorination reagent in a second dehydrochlorination reaction to form a second dehydrochlorination reaction product having 1,1,2,3-tetrachloropropene or a 2,3,3,3-tetrachloropropene.

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.

PROCESS FOR THE PRODUCTION OF CHLORINATED PROPANES AND/OR PROPENES

Processes for the production of chlorinated propanes and/or propenes are provided. The present processes make use of methylacetylene, a by-product in the production of ethylene and/or propylene, as a low cost starting material, alone or in combination with propadiene, propene and/or propane. In the latter embodiments, the processes may also be utilized to provide a substantially pure stream of propane.

Preparation of (Z)-1,2-dichloroalkenes from terminal alkynes

(Z)-1,2-Dihaloalkenes are thermodynamically disfavoured of the two stereoisomers. This paper reports the synthesis of some (Z)-1,2-dichloroalkene analogues from mucochloric acid. A more versatile approach involved the chloroboration of terminal alkynes to yield corresponding (Z)-chloroboronic acid as a first step. Treatment of the organoboronic acid with potassium hydrogen difluoride followed by tetrabutylammonium trichloride gave (Z)-1,2- dichloroalkenes in moderate to good yields in a stereospecific manner.

Method for producing 2,3,3,3-tetrafluoropropene

A method for preparing 2,3,3,3-tetrafluoropropene comprising contacting a reactant comprising CCl2=CFCH2Cl with a fluorinating agent, such as HF, under conditions effective to produce a reaction product comprising CF3CF=CH2.

PROCESSES FOR PREPARING 1,1,2,3-TETRACHLOROPROPENE

Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH2ClCCl2CH2Cl in the gas phase to produce CHCl═CClCH2Cl; chlorinating the CHCl═CClCH2Cl to form CHCl2CCl2CH2Cl; and catalytically dehydrochlorinating the CHCl2CCl2CH2Cl in the gas phase to form CCl2═CClCH2Cl.

MANUFACTURE OF DICHLOROPROPANOL

Manufacture of dichloropropanol Process for manufacturing dichloropropa nol wherein a glycerol-based product comprising at least one diol containi ng at least 3 carbon atoms other than 1,2- propanediol, is reacted with a chlorinati ng agent, and of products derived from dichloropropanol such as ep ichlorohydrin and epoxy resins. No figure.

SYNTHESIS AND PROPERTIES OF TRIETHYLBENZYLAMMONIUM ALKOXIDES. REACTIVITY IN ELIMINATION AND NUCLEOPHILIC SUBSTITUTION REACTIONS

Triethylbenzylammonium alkoxides exhibit high reactivity during the elimination of hydrogen chloride from polychloroalkanes and can also be used in the synthesis of ethers from halogenoalkanes.Quaternary ammonium salts do not form tetraalkylammonium or trialkylbenzylammonium alkoxides under the influence of a concentrated aqueous solution of sodium hydroxide in the presence of alcohols.