563-58-6

Basic information

• Product Name: 1,1-Dichloropropene
• Synonyms: 1,1-dichloropropene neat standard*for epa methods; 1,1-Dichloropropene (1mg/ml in Methanol for Water Analysis)
• CAS NO: 563-58-6
• Molecular Formula: C₃H₄Cl₂
• Molecular Weight: 110.97
• EINECS: 209-253-3
• Mol File: 563-58-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 78.1°Cat760mmHg
• Flash Point: 0.6°C
• Appearance: /
• Density: 1.177g/cm³
• CAS DataBase Reference: 1,1-Dichloropropene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dichloropropene(563-58-6)
• EPA Substance Registry System: 1,1-Dichloropropene(563-58-6)

Safety Data

• Hazardous Substances Data: 563-58-6(Hazardous Substances Data)

Usage

General Description

1,1-Dichloropropene, also known as 1,1-D, is a chemical compound that is commonly used as a soil fumigant and pesticide. It exists as a colorless liquid with a sweet, chloroform-like odor. The compound is produced by direct chlorination of propene. It is listed as a probable human carcinogen, and exposure to its vapors can irritate the eyes, skin and respiratory tract. It also becomes harmful if swallowed or absorbed through skin, and chronic exposure can damage the lungs, liver, and kidneys. While it is primarily used in agriculture to control nematodes, its production and use have raised profound health and environmental concerns.

InChI:InChI=1/C3H4Cl2/c1-2-3(4)5/h2H,1H3

Synthetic route

triethylsilane (617-86-7) + 3,3,3-trichloro-1-propene (2233-00-3) → 1,1,1-trichloropropane (7789-89-1) + 1,1-dichloropropene (563-58-6) + 3,3,3-trichloropropyltriethylsilane (17873-97-1) + hexa-Si-ethyl-Si,Si'-propanediyl-bis-silane (17955-48-5)

Conditions	Yield
With dihydrogen hexachloroplatinate; isopropyl alcohol at 20℃; for 48h; Further byproducts given. Title compound not separated from byproducts;	A 17% B 55% C 7% D 0.4%

triethylsilane (617-86-7) + 3,3,3-trichloro-1-propene (2233-00-3) → 1,1-dichloropropene (563-58-6) + 3,3,3-trichloropropyltriethylsilane (17873-97-1) + hexa-Si-ethyl-Si,Si'-propanediyl-bis-silane (17955-48-5) + ((E)-1-Chloro-propenyl)-triethyl-silane (114700-65-1)

Conditions	Yield
With dihydrogen hexachloroplatinate; isopropyl alcohol at 20℃; for 48h; Further byproducts given. Title compound not separated from byproducts;	A 55% B 7% C 0.4% D n/a

triethylsilane (617-86-7) + 3,3,3-trichloro-1-propene (2233-00-3) → 1,1-dichloropropene (563-58-6) + 3,3,3-trichloropropyltriethylsilane (17873-97-1) + hexa-Si-ethyl-Si,Si'-propanediyl-bis-silane (17955-48-5) + ((Z)-1-Chloro-propenyl)-triethyl-silane (114700-64-0)

Conditions	Yield
With dihydrogen hexachloroplatinate; isopropyl alcohol at 20℃; for 48h; Further byproducts given. Title compound not separated from byproducts;	A 55% B 7% C 0.4% D n/a

3,3,3-trichloro-1-propene (2233-00-3) → 1,1,1-trichloropropane (7789-89-1) + 1,1-dichloropropene (563-58-6) + 3,3,3-trichloropropyltriethylsilane (17873-97-1) + hexa-Si-ethyl-Si,Si'-propanediyl-bis-silane (17955-48-5)

Conditions	Yield
With triethylsilane; dihydrogen hexachloroplatinate; isopropyl alcohol at 20℃; for 48h; Further byproducts given;	A 17% B 55% C 7% D 0.4%

3,3,3-trichloro-1-propene (2233-00-3) → 1,1,1-trichloropropane (7789-89-1) + 1,1-dichloropropene (563-58-6) + ((E)-1-Chloro-propenyl)-triethyl-silane (114700-65-1) + ((Z)-1-Chloro-propenyl)-triethyl-silane (114700-64-0)

Conditions	Yield
With triethylsilane; dihydrogen hexachloroplatinate; isopropyl alcohol at 20℃; for 48h; Further byproducts given;	A 17% B 55% C n/a D n/a

1,1,1-trichloropropane (7789-89-1) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With iron(III) chloride

1,1,2-trichloropropane (598-77-6) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With sodium hydroxide
With benzyltrimethylammonium chloride; sodium hydroxide In water at 70℃; for 4h;
With sodium hydroxide

1,1,1,2,3-pentachloro-propane (21700-31-2) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With ethanol; zinc at 65℃;

3,3-dichloroallyl chloride (2567-14-8) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With ethanol; zinc at 65℃;

1,1-dichloro-3-iodo-propene (4358-76-3) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2,2,3-trichlorobutyraldehyde (76-36-8) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With potassium hydroxide

2-acetoxy-1,1,1-trichloropropane (19376-15-9) → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With ethanol; zinc

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-dichlorocyclopropane (2088-35-9) → 2,3-Dichloroprop-1-ene (78-88-6) + 1,1-dichloropropene (563-58-6)

Conditions	Yield
In gas at 336.9 - 451.9℃; under 10.5 Torr; Kinetics; Product distribution;

2.2.3-trichlorobutyrate sodium → 1,1-dichloropropene (563-58-6)

Conditions	Yield
Bei der Destillation;

1,1,2-trichloropropane (598-77-6) + 20 percent NaOH → 1,1-dichloropropene (563-58-6)

alcoholate of butyrchloroas → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With potassium hydroxide

asymm.trichloro-isopropyl alcohol → 1,1-dichloropropene (563-58-6)

Conditions	Yield
With acetic acid; zinc

1-ethoxy-2,2,3-trichloro-butan-1-ol + diluted KOH-solution → 1,1-dichloropropene (563-58-6)

ethanol (64-17-5) + 1,1,1,2,3-pentachloro-propane (21700-31-2) + zinc → 1,1-dichloropropene (563-58-6)

ethanol (64-17-5) + 3,3-dichloroallyl chloride (2567-14-8) + zinc → 1,1-dichloropropene (563-58-6)

Conditions	Yield
at 65℃;

1,1,1-trichloropropan-2-ol (76-00-6) + acetic acid (64-19-7) + zinc → 1,1-dichloropropene (563-58-6)

2,2,3-tri-chlorobutane-1,1-diol (76-40-4) + KOH-solution → formic acid (64-18-6) + 1,1-dichloropropene (563-58-6)

1,1-dichloropropene (563-58-6) + phenylmagnesium bromide → (Z)-(1-Chloro-1-propenyl)benzene (4541-85-9)

Conditions	Yield
With PdCl2(dbbp) In diethyl ether for 2h; Heating;	90%

1,1-dichloropropene (563-58-6) → 3,3-dichloro-2-propen-1-yl bromide (36469-73-5)

Conditions	Yield
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 4h; Heating;	75%
With N-Bromosuccinimide
With N-Bromosuccinimide; dibenzoyl peroxide
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane

1,1-dichloropropene (563-58-6) + phenyltrichloromethylmercury (3294-57-3) → 1,1,2,2-tetrachloro-3-methylcyclopropane (164783-82-8)

Conditions	Yield
In benzene for 18h; Heating;	27%

1,1-dichloropropene (563-58-6) + sodium trichloroacetate (650-51-1) → 1,1,2,2-tetrachloro-3-methylcyclopropane (164783-82-8)

Conditions	Yield
In 1,2-dimethoxyethane for 30h; Heating;	24%

chloroform (67-66-3) + 1,1-dichloropropene (563-58-6) → 1,1,2,2-tetrachloro-3-methylcyclopropane (164783-82-8)

Conditions	Yield
With sodium hydroxide; cetyltrimethylammonim bromide In water for 24h; Ambient temperature;	14%

1,1-dichloropropene (563-58-6) → 1,1,1-trifluoropropane (421-07-8) + 1-chloro-1,1-difluoro-propane (421-02-3)

Conditions	Yield
With hydrogen fluoride at 90 - 100℃;

1,1-dichloropropene (563-58-6) → 1-chloro-1,1-difluoro-propane (421-02-3)

Conditions	Yield
With hydrogen fluoride at 100℃;

1,1-dichloropropene (563-58-6) → 1-chloro-1,1-difluoro-propane (421-02-3) + 1,1-dichloro-1-fluoro-propane (7799-56-6)

Conditions	Yield
With hydrogen fluoride at 100℃; under 14710.2 Torr;

1,1-dichloropropene (563-58-6) → 1,1,1-trichloropropane (7789-89-1)

Conditions	Yield
With hydrogenchloride; aluminium trichloride at 5 - 10℃;

1,1-dichloropropene (563-58-6) → 1,1,1,2-tetrachloropropane (812-03-3)

Conditions	Yield
With chlorine; iron(III) chloride
With chlorine unter Lichtausschluss;
With carbon disulfide; chlorine

1,1-dichloropropene (563-58-6) → 1,2-dibromo-1,1-dichloro-propane (872826-15-8)

Conditions	Yield
With bromine

1,1-dichloropropene (563-58-6) → 1,1,1,2,2-pentachloropropane (64240-29-5)

Conditions	Yield
With chlorine

1,1-dichloropropene (563-58-6) → 3,3-dichloroallyl chloride (2567-14-8)

Conditions	Yield
With chlorine at 550℃;

1,1-dichloropropene (563-58-6) → 2-Butynoic acid (590-93-2)

Conditions	Yield
anschliesssend Behandeln mit Wasser,Alkohol und Aether und CO2;

1,1-dichloropropene (563-58-6) → bis-(β,β,β-trichloro-isopropyl)-disulfide (98134-66-8)

Conditions	Yield
With disulfur dichloride; iron(III) chloride

1,1-dichloropropene (563-58-6) → sodium but-2-ynoate (1071-35-8)

Conditions	Yield
With sodium bei der Einw. von CO2 auf das Reaktionsprodukts;

1,1-dichloropropene (563-58-6) → prop-1-yne (74-99-7)

Conditions	Yield
With potassium hydroxide; ethanol at 150℃;
With sodium Zers. des Reaktionsproduktes mit Wasser;

1,1-dichloropropene (563-58-6) + thiourea (17356-08-0) → S-(1-chloro-allyl)-isothiourea (103854-82-6)

Upstream product

• 7789-89-1 1,1,1-trichloropropane 
• 598-77-6 1,1,2-trichloropropane 
• 4358-76-3 1,1-dichloro-3-iodo-propene 
• 76-36-8 2,2,3-trichlorobutyraldehyde 
• 187737-37-7 propene 
• 76-40-4 2,2,3-tri-chlorobutane-1,1-diol 
• 76-00-6 1,1,1-trichloropropan-2-ol 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 2567-14-8 3,3-dichloroallyl chloride 
• 21700-31-2 1,1,1,2,3-pentachloro-propane 
• 2088-35-9 1,1-dichlorocyclopropane 
• 2233-00-3 3,3,3-trichloro-1-propene 
• 617-86-7 triethylsilane 

Downstream Products

• 421-07-8 1,1,1-trifluoropropane 
• 421-02-3 1-chloro-1,1-difluoro-propane 
• 7789-89-1 1,1,1-trichloropropane 
• 812-03-3 1,1,1,2-tetrachloropropane 
• 2567-14-8 3,3-dichloroallyl chloride 
• 590-93-2 2-Butynoic acid 
• 74-99-7 prop-1-yne 
• 97157-34-1 Tris-triphenylsilyl-propadien 
• 18919-82-9 1.2-Bis-triphenylsilyl-propen 
• 18752-22-2 triphenyl(1-propenyl)silane 
• 6104-36-5 1-(triphenylsilyl)prop-1-yne 
• 18752-07-3 2-Chlor-3-triphenylsilyl-propen 
• 430-95-5 1,1-dichloro-2-fluoro-propene 
• 64240-29-5 1,1,1,2,2-pentachloropropane 

Relevant articles and documents

PROCESS FOR THE PRODUCTION OF CHLORINATED ALKANES

Processes for the production of chlorinated alkanes are provided. The present processes comprise dehydrochlorinating one or more trichloroalkanes having from 3-6 carbon atoms and vicinal chlorine atoms, followed by a series of sequential chlorination and/or further dehydrochlorination steps. Because the trichloroalkane is first dehydrochlorinated, rather than being first chlorinated, greater specificity to desired tetra- and pentachloroalkanes can be seen.

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The Thermal Decomposition of 1,1-Dichlorocyclopropane

The thermal gas phase isomerization of 1,1-dichlorocyclopropane yields 2,3 dichloropropene and 1,1-dichloropropene in two parallel reaction channels.The product ratio was studied in the range 610-725 K. - Keywords: Reaction kinetics / Isomerization / Unimolecular reaction