1888-71-7

Basic information

• Product Name: 1,1,2,3,3,3-hexachloro-1-propene
• Synonyms: Propene,hexachloro- (6CI,7CI,8CI); 1,1,1,2,3,3-Hexachloropropene; Hexachloro-1-propene;Hexachloropropene; Hexachloropropylene; NSC 7297; Perchloropropene;Perchloropropylene
• CAS NO: 1888-71-7
• Molecular Formula: C₃Cl₆
• Molecular Weight: 248.73
• EINECS: 217-560-9
• Mol File: 1888-71-7.mol

Chemical Properties

• Boiling Point: 209-210 °C(lit.)
• Flash Point: 209-210°C
• Appearance: colourless liquid
• Density: 1.765 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.292mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 1,1,2,3,3,3-hexachloro-1-propene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2,3,3,3-hexachloro-1-propene(1888-71-7)
• EPA Substance Registry System: 1,1,2,3,3,3-hexachloro-1-propene(1888-71-7)

Safety Data

• Hazard Codes: T:Toxic
• Statements: R23:Toxic by inhalation.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S28A:After contact wit
• Hazardous Substances Data: 1888-71-7(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
1,1,2,3,3,3-hexachloro-1-propene is used as a fumigant and pesticide for its effectiveness in controlling pests. Its strong chemical properties allow it to penetrate and kill a wide range of pests, making it a valuable tool in agricultural and horticultural applications.
However, due to its persistence in the environment and potential for bioaccumulation, leading to soil and water contamination, the use of 1,1,2,3,3,3-hexachloro-1-propene is heavily regulated in many countries. 1,1,2,3,3,3-hexachloro-1-propene's toxic nature and links to environmental and health risks have prompted ongoing efforts to develop safer alternatives and to mitigate its impact on the environment.

InChI:InChI=1/C3Cl6/c4-1(2(5)6)3(7,8)9

Synthetic route

1,1,1,2,2,3,3-heptachloropropane (594-89-8) → perchloropropene (1888-71-7)

Conditions	Yield
With methyl diethylphosphinate at 180℃; for 14.5h;	56%
With potassium hydroxide
at 250 - 420℃;

trichloro(heptachloropropyl)silane (131367-96-9) → perchloropropene (1888-71-7)

Conditions	Yield
With aluminium trichloride at 160 - 180℃;	52%

pentachloro-2-(trimethylsiloxy)propene (87651-34-1) → chloro-trimethyl-silane (75-77-4) + pentachloroacetone (1768-31-6) + perchloropropene (1888-71-7)

Conditions	Yield
With phosphorus pentachloride at 150℃; for 15h; Yields of byproduct given;	A 52% B n/a C n/a
With phosphorus pentachloride at 150℃; for 15h; Yield given. Title compound not separated from byproducts;	A 52% B n/a C n/a

chloroform (67-66-3) → perchloropropene (1888-71-7)

Conditions	Yield
With hydrogen

1,1,1,2,3,3,3-heptachloropropane (3849-33-0) → perchloropropene (1888-71-7)

Conditions	Yield
at 350℃;

2-fluoropentachloropropylene (815-15-6) → perchloropropene (1888-71-7)

Conditions	Yield
With aluminium trichloride

heptachloro-butyraldehyde (25290-40-8) → perchloropropene (1888-71-7)

Conditions	Yield
With sodium ethanolate

pentaerythrityl tetrachloride (3228-99-7) → perchloropropene (1888-71-7)

Conditions	Yield
With chlorine at 200℃; Irradiation;

octachloropropane (594-90-1) → perchloropropene (1888-71-7)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In chloroform

perchloroallene (18608-30-5) → perchloropropene (1888-71-7)

Conditions	Yield
With chlorine In dichloromethane

heptachlorobutyryl chloride (22414-28-4) → perchloropropene (1888-71-7)

Conditions	Yield
In N,N-dimethyl-formamide

propene (187737-37-7) → 1,1,1,3,3-pentachloropropene (6262-54-0) + 1,1-dichloropropene (563-58-6) + 3,3-dichloroallyl chloride (2567-14-8) + perchloropropene (1888-71-7) + 1,1,3,3-tetrachloro-1-propene (18611-43-3) + propenyl chloride (590-21-6)

Conditions	Yield
With hydrogenchloride; oxygen; CuCl2 on calcined alumina at 490℃; Product distribution; several conditions investigated;

1,1,1,2,2,3,3-heptachloropropane (594-89-8) + alcoholic KOH-solution → perchloropropene (1888-71-7)

1,1,1,2,3,3,3-heptachloropropane (3849-33-0) + alcoholic potash → perchloropropene (1888-71-7)

asymm. heptachloropropane → perchloropropene (1888-71-7)

Conditions	Yield
With potassium hydroxide
With pyridine
With -base of crystal violet

pyridine (110-86-1) + 1,1,1,2,2,3,3-heptachloropropane (594-89-8) → hydrogenchloride (7647-01-0) + perchloropropene (1888-71-7)

1,1,1,2,2,3,3-heptachloropropane (594-89-8) + alkali → hydrogenchloride (7647-01-0) + perchloropropene (1888-71-7)

1,1,2,3-tetrachloro-3,3-difluoropropene (431-50-5) + antimonypentachloride (7647-18-9) → 1,1,2-trichloro-3,3,3-trifluoropropene (431-52-7) + 1,1,2,3,3-pentachloro-3-fluoropropene (815-14-5) + perchloropropene (1888-71-7)

1,1,1,2,2,3,3-heptachloropropane (594-89-8) + -base of crystal violet → perchloropropene (1888-71-7) + crystal violet (548-62-9)

1,1,2,3,3,4,4,5,6,6-decachloro-hexa-1,5-diene (29030-84-0) → 1,1,2,2-tetrachloroethylene (127-18-4) + perchloropropene (1888-71-7) + octachloro-1-methylene-cyclopentene-(3)

Conditions	Yield
at 200 - 210℃;

heptachloro-butyraldehyde (25290-40-8) + sodium ethanolate (141-52-6) → perchloropropene (1888-71-7) + sodium formate (141-53-7) + sodium chloride

diethyl ether (60-29-7) + octachloropropane (594-90-1) + aluminium → perchloropropene (1888-71-7) + solid octachlorohexatriene + liquid octachlorohexatriene + octachloro-1-methylene-cyclopentene of mp: 183 degree

Conditions	Yield
Produkt 5:Perchlorfulven;

1,1,1,3,3,3-hexachloropropane (3607-78-1) → 1-chloro-1,1,3,3,3-pentafluoropropane (460-92-4) + 2H-pentafluoropropene (690-27-7) + 1,1,1,3,3,3-hexafluoropropane (690-39-1) + perchloropropene (1888-71-7)

Conditions	Yield
With hydrogen fluoride; chlorine; antimonypentachloride at 80 - 95℃; under 8517.48 - 10069 Torr;
With hydrogen fluoride; chromium(III) oxide at 300℃;

1,1,1,2,2,3,3-heptachloropropane (594-89-8) + tetrabutyl-ammonium chloride (1112-67-0) → perchloropropene (1888-71-7)

Conditions	Yield
With potassium hydroxide	237 g (95%)

1,1,1,2,2,3,3-heptachloropropane (594-89-8) + tetra-n-butylphosphonium chloride (2304-30-5) → perchloropropene (1888-71-7)

Conditions	Yield
With potassium hydroxide	239 g (96%)

tricaprylylmethyl ammoniumchloride + 1,1,1,2,2,3,3-heptachloropropane (594-89-8) → perchloropropene (1888-71-7)

Conditions	Yield
With potassium hydroxide	237 g (95%)

tetrachloromethane (56-23-5) → Hexachlorobutadiene (87-68-3) + perchloropropene (1888-71-7) + hexachlorobenzene (118-74-1)

Conditions	Yield
With silica gel In neat (no solvent) byproducts: SiCl4, COCl2; decomposition of streaming CCl4 with high-frequency discharge in a quartz tube; condensation of the reaction mixture at -190°C; mechanism discussed; further products;; determination by IR and MS;;

uranyl nirate hexahydrate + perchloropropene (1888-71-7) → uranium(IV) chloride (10026-10-5)

Conditions	Yield
Inert atmosphere; Reflux;	100%

perchloropropene (1888-71-7) + uranium(VI) trioxide → uranium(IV) chloride (10026-10-5)

Conditions	Yield
at 190℃; for 18h; Schlenk technique; Inert atmosphere;	98%
In neat (no solvent) refluxing; sublimation (vac.);
In neat (no solvent) absence of air and moisture; refluxing;

uranium(IV) oxide dihydrate + uranium(VI) oxide dihydrate + perchloropropene (1888-71-7) → uranium(IV) chloride (10026-10-5)

Conditions	Yield
In further solvent(s) (N2); standard Schlenk technique; UO2*2H2O was added to hexachloropropene at 190°C; heated at 190°C; UO3*2H2O was carefully added;mixt. was heated at 190°C overnight; cooled to room temp.; filtered; washed (CH2Cl2); dried (vac.);	98%

perchloropropene (1888-71-7) → 2,3,3-trichloroacryloyl chloride (815-58-7) + thionyl chloride (84percent)

Conditions	Yield
With aluminium trichloride; sulfur dioxide at 90℃; for 48h;	A 85% B n/a

3-(3-pyridyl)propan-1-ol (2859-67-8) + 2,3,3-trichloroacryloyl chloride (815-58-7) + perchloropropene (1888-71-7) → 3-(3-Pyridyl)-1-propyl-2',3',3'-trichloroacrylate (103146-15-2)

Conditions	Yield
With pyridine; iron(III) chloride	82%

perchloropropene (1888-71-7) → 1,1,2-trichloro-3,3,3-trifluoropropene (431-52-7) + 1,1,2,3-tetrachloro-3,3-difluoropropene (431-50-5) + 1,1,2,3,3-pentachloro-3-fluoropropene (815-14-5)

Conditions	Yield
With antimony(III) fluoride at 170℃;	A 74.2% B n/a C n/a
With antimony(III) fluoride at 170℃;

perchloropropene (1888-71-7) + 2,3,4,5,6-pentafluoroaniline (771-60-8) → 1,1,2,3-tetrachloro-4-(pentafluorophenyl)-4-aza-1,3-butadiene (119771-89-0)

Conditions	Yield
With aluminium trichloride In fluorobenzene at 70 - 80℃; for 6h;	73%

perchloropropene (1888-71-7) → 3,4,5-trichlor-1,2-dithiolylium chloride

Conditions	Yield
With sulfur at 170℃; for 24h;	70%

methyl thiocyanate (556-64-9) + perchloropropene (1888-71-7) → 1,3,4,5,5-pentachloro-1-methylthio-2-azonia-1,2,4-pentatriene hexachloroantimonate

Conditions	Yield
With antimonypentachloride In 1,2-dichloro-ethane for 0.166667h; Heating;	66%

perchloropropene (1888-71-7) + methyl isocyanate (624-83-9) → 2,2-dichloro-5,6-dihydro-3,5-dimethyl-4-(trichlorovinyl)-6-oxo-2H-1,3,5-oxadiazinium hexachloroantimonate

Conditions	Yield
With antimonypentachloride In dichloromethane 1.) -30 deg C, 30 min, 2.) 23 deg C, 4 h;	63%

perchloropropene (1888-71-7) + p-Tolylisocyanate (622-58-2) → 1-(chlorocarbonyl)-2,3,4-trichloro-6-methylquinolinium hexachloroantimonate

Conditions	Yield
In dichloromethane 1.) -40 deg C, 30 min, 2.) 23 deg C, 4 h;	61%

2-propyl thiocyanate (625-59-2) + perchloropropene (1888-71-7) → 2,4,5,6-tetrachloro-1,3-thiazinium hexachloroantimonate

Conditions	Yield
With antimonypentachloride In 1,2-dichloro-ethane for 0.0833333h; Heating;	57%

uranium oxide + perchloropropene (1888-71-7) → uranium(IV) chloride (10026-10-5)

Conditions	Yield
Inert atmosphere;	55%

hexyl-sulfinyl-amine (66838-82-2) + perchloropropene (1888-71-7) → N-hexyl-2,3,3-trichloro-2-propenamide

Conditions	Yield
With antimonypentachloride In dichloromethane 1.) -40 deg C, 10 min; 2.) 23 deg C, 1 h;	49%

perchloropropene (1888-71-7) + 1,2-dichloro-benzene (95-50-1) → hexachloroindene

Conditions	Yield
With iron(III) chloride In 1,1,2,2-tetrachloroethylene	48.7%

perchloropropene (1888-71-7) + ethyl isocyanate (109-90-0) → 2,2-dichloro-3,5-diethyl-5,6-dihydro-4-(trichlorovinyl)-6-oxo-2H-1,3,5-oxadiazinium hexachloroantimonate

Conditions	Yield
With antimonypentachloride In dichloromethane 1.) -30 deg C, 30 min, 2.) 23 deg C, 4 h;	48%

perchloropropene (1888-71-7) + 1,4-dichloropermethyltetrasilane (754-75-6) → hexadecamethyl-2,3,4,5,6,7,8,9,10-octasilabicyclo<4.4.1>undeca-1(11),6(11)-diene (146574-31-4)

Conditions	Yield
With magnesium In tetrahydrofuran at 50℃; for 4h;	34%

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane (812-36-2) + perchloropropene (1888-71-7) → C18H36Cl2Si6

Conditions	Yield
With magnesium In tetrahydrofuran at 50℃; for 4h;	16%

cis-1,2-Dichloroethylene (156-59-2) + perchloropropene (1888-71-7) → 3H-heptachloro-cyclopentene (858423-01-5)

Conditions	Yield
With aluminium trichloride; dichloromethane at 13 - 15℃;

cis-1,2-Dichloroethylene (156-59-2) + perchloropropene (1888-71-7) → hexachlorocyclopentadiene (77-47-4)

Conditions	Yield
With aluminium trichloride; dichloromethane at 9℃; anschliessendes Erhitzen auf Siedetemperatur;

4-Chloro-3-methylphenol (59-50-7) + perchloropropene (1888-71-7) → 3,4,6-trichloro-7-methyl-coumarin (71706-65-5)

Conditions	Yield
With carbon disulfide; aluminium trichloride anschliessend Behandeln mit wss. Schwefelsaeure;

p-cresol (106-44-5) + perchloropropene (1888-71-7) → 3,4-dichloro-6-methyl-2H-chromen-2-one (15736-24-0)

Conditions	Yield
With carbon disulfide; aluminium trichloride anschliessend Behandeln mit wss. Schwefelsaeure;
Stage #1: p-cresol; perchloropropene With aluminum (III) chloride In carbon disulfide Stage #2: With sulfuric acid; water

3-monochlorophenol (108-43-0) + perchloropropene (1888-71-7) → 3,4,7-trichloro-coumarin (99846-75-0)

4-bromo-phenol (106-41-2) + perchloropropene (1888-71-7) → 6-bromo-3,4-dichloro-2H-chromen-2-one (63795-99-3)

Chlorodifluoromethane (75-45-6) + perchloropropene (1888-71-7) → 1,1,2-trichloro-3,3,3-trifluoropropene (431-52-7)

Conditions	Yield
With aluminium trichloride at 150℃; dann auf 200grad;

Chlorodifluoromethane (75-45-6) + perchloropropene (1888-71-7) → 1,1,2,3-tetrachloro-3,3-difluoropropene (431-50-5)

Conditions	Yield
With aluminium trichloride at 100℃;

Upstream product

• 67-66-3 chloroform 
• 3849-33-0 1,1,1,2,3,3,3-heptachloropropane 
• 594-89-8 1,1,1,2,2,3,3-heptachloropropane 
• 815-15-6 2-fluoropentachloropropylene 
• 25290-40-8 heptachloro-butyraldehyde 
• 3228-99-7 pentaerythrityl tetrachloride 
• 594-90-1 octachloropropane 
• 18608-30-5 perchloroallene 
• 22414-28-4 heptachlorobutyryl chloride 
• 187737-37-7 propene 
• 131367-96-9 trichloro(heptachloropropyl)silane 
• 87651-34-1 pentachloro-2-(trimethylsiloxy)propene 
• 110-86-1 pyridine 
• 431-50-5 1,1,2,3-tetrachloro-3,3-difluoropropene 

Downstream Products

• 77-47-4 hexachlorocyclopentadiene 
• 431-52-7 1,1,2-trichloro-3,3,3-trifluoropropene 
• 2257-35-4 2,3,3-trichloroacrylic acid 
• 56-23-5 tetrachloromethane 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 67-72-1 hexachloroethane 
• 118-74-1 hexachlorobenzene 
• 1482-85-5 perdeuterioallene 
• 6111-63-3 tetradeuterio-propyne 
• 815-58-7 2,3,3-trichloroacryloyl chloride 
• 17640-12-9 methyl trichloro-propenoate 
• 29030-84-0 1,1,2,3,3,4,4,5,6,6-decachloro-hexa-1,5-diene 
• 5196-72-5 3,4,6-trichloro-2H-chromen-2-one 
• 90415-55-7 trichloro-acrylic acid-(4-chloro-phenyl ester) 

Relevant articles and documents

Method of making 1,1,3,3,3-pentafluoropropene

The invention provides an economic process for the manufacture of the hydrofluorocarbon 1,1,3,3,3-pentafluoropropene (HFC-1225zc). HFC-1225zc can be made from the dehydrochlorination of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa). Alternatively, HFC-1225zc can also be made from the dehydrofluorination of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa). HFC-1225zc) is a compound that has the potential to be used as a low Global Warming Potential refrigerant, blowing agent, aerosol propellant, or solvent.

Method of producing 1,1,1,3,3-pentafluoropropane, a method of producing 1,1,1,3,3-pentafluoro-2-halogeno-3-chloropropane, and a method of producing 1,1,1,2,3,3-hexachloropropene

There are provided production methods of 1,1,1,3,3-pentafluoropropane characterized in that 1,1,1,3,3-pentafluoro-2,3-dichloropropane is reacted with hydrogen fluoride in the presence of a noble metal catalyst; of 1,1,1,3,3-pentafluoro-2-halogeno-3-chloropropane characterized in that the halogenated propene indicated as general formula I is fluorinated in the presence of antimony trihalogenide and/or antimony pentahalogenide by hydrogen fluoride of mole ratio of or over five times the said antimony halogenide in a liquid phase; and of 1,1,1,2,3,3-hexaohloropropene characterized in that 1,1,1,2,2,3,3-heptachloropropane is reacted with an aqueous solution of alkali metal hydroxide in the presence of a phase transfer catalyst. Therefore, an industrial manufacturing method which is possible to obtain the objective product easily at low cost and high yield can be provided.

PHOTOCHEMICAL REDUCTION OF CARBON-HALOGEN BONDS. 3. REGIOSELECTIVITY OF THE REACTION IN FLUORINATED HALOGENOPROPANOATES.

The ester group exhibits a strong directive effect in the photochemical reduction of a carbon-halogen bond and directs the reduction in perhalogenated chlorofluoropropanoates of the type CFXY-CClZ-COOR (X,Y,Z = Cl, F) to the α-position in the acyl part of an ester.The reduction takes place with the same regioselectivity even in esters CFCl2-CHCl-COOR (10).In esters containing an α -CCl2- group the reductions to the first and the second stages can be separated and the individual reduction products can be obtained preparatively.The α C-F bond is more difficult to reduce and therefore in the ester CFCl2-CHF-COOR (11) the β C-Cl bond was reduced specifically and in the ester CF2Cl-CHF-COOR (12) both the α C-F bond and the β C-Cl bond were reduced parallely.The relative reactivity of fluorinated halogenopropanoates with an α C-Cl bond showed only small differences in the reduction with 2-propanol in the presence of acetone as a sensitiser; the quantum yield Φ reached values of about 28-35 under kinetic measurements and thus proved the existence of a chain radical mechanism.

TWO ROUTES OF PROPENE CONVERSION INTO PERCHLORO DERIVATIVES BY THE ACTION OF HYDROGEN CHLORIDE AND OXYGEN.

Destructive catalytic conversions of propene by the action of hydrogen chloride and oxygen are of complex character and may proceed by several routes, depending on the oxygen and hydrogen chloride contents in the reactants. Elucidation of the character of these routes is of practical interest, and is necessary for selection of the process conditions. In view of this , the influence of the hydrogen chloride:propene ration on the process was studied in the ranges from 0 to 6 (contract time 2 sec) and from 6 to 12 (contact time 5 sec) at the constant stoichiometric ratio HCl:O//2 equals 2. The interaction of propene with hydrogen chloride at HCl:C//3H//6 ratios from 6 to 12 (Fig. lb) has certain peculiarities, with chlorinolysis of hexachloropropene. However, at HCl:C//3H//6 ratios from 9 to 10. 5 acrolein is formed and then converted into various compounds with evolution of the corresponding amounts of carbon monoxide. It is shown that the conversions of propene into various compounds proceed by two routes, with intermediate formation of allyl chloride and acrolein.

Process for the preparation of 4,5-dichloro-1,2-dithiacyclopenten-3-one

An improved process for preparation of 4,5-dichloro-1,2-dithia-cyclopenten-3-one of the formula STR1 by reacting hexachloroprene with sulphur at elevated temperatures, wherein the improvement comprises hydrolyzing by-product sulphur chlorides by conducting the reaction in the presence of water.