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
• Article Data: 8

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

General Description

1,1,2,3,3,3-hexachloro-1-propene is a chemical compound with six chlorine atoms attached to a propene molecule. It is a highly toxic and potentially carcinogenic substance that is commonly used as a fumigant and pesticide. The compound has been linked to environmental contamination and has been found to persist in soil and water, posing a threat to both human health and the environment. Due to its toxic nature and potential for bioaccumulation, the use and disposal of 1,1,2,3,3,3-hexachloro-1-propene is heavily regulated in many countries. Efforts are ongoing to develop safer alternatives and to mitigate the impact of this chemical 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 
• 3228-99-7 pentaerythrityl tetrachloride 
• 594-90-1 octachloropropane 
• 18608-30-5 perchloroallene 
• 22414-28-4 heptachlorobutyryl chloride 
• 87651-34-1 pentachloro-2-(trimethylsiloxy)propene 
• 29030-84-0 1,1,2,3,3,4,4,5,6,6-decachloro-hexa-1,5-diene 
• 25290-40-8 heptachloro-butyraldehyde 
• 141-52-6 sodium ethanolate 
• 60-29-7 diethyl ether 
• 56-23-5 tetrachloromethane 
• 187737-37-7 propene 
• 815-15-6 2-fluoropentachloropropylene 
• 594-89-8 1,1,1,2,2,3,3-heptachloropropane 

Downstream Products

• 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 
• 431-52-7 1,1,2-trichloro-3,3,3-trifluoropropene 
• 5196-72-5 3,4,6-trichloro-2H-chromen-2-one 
• 90415-55-7 trichloro-acrylic acid-(4-chloro-phenyl ester) 
• 5117-56-6 3,4-dichloro-2H-chromen-2-one 

Relevant articles and documents

Reaction of methyl esters of P(IV) acids with polychlorinated hydrocarbons [4]

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PREPARATION AND PROPERTIES OF POLYCHLORO-SUBSTITUTED PROPYL-, BUTYL-, AND PENTYL-TRICHLOROSILANES

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