10061-02-6

Basic information

• Product Name: (E)-1,3-Dichloro-1 -propene
• Synonyms: 1-Propene,1,3-dichloro-, (E)-;Propene, 1,3-dichloro-, (E)- (8CI);(E)-1,3-Dichloro-1-propene;(E)-1,3-Dichloropropene;trans-1,3-Dichloro-1-propene;trans-1,3-Dichloropropylene;trans-3-Chloroallyl chloride
• CAS NO: 10061-02-6
• Molecular Formula: C₃H₄Cl₂
• Molecular Weight: 110.96986
• EINECS: 208-826-5
• Mol File: 10061-02-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 108.4 °C at 760 mmHg
• Flash Point: 27.8 °C
• Appearance: colourless liquid
• Density: 1.175 g/cm³
• Refractive Index: 1.4748
• CAS DataBase Reference: (E)-1,3-Dichloro-1 -propene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1,3-Dichloro-1 -propene(10061-02-6)
• EPA Substance Registry System: (E)-1,3-Dichloro-1 -propene(10061-02-6)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R10:; R22:; R40:
• Safety Statements: S16:; S36/37:
• Hazardous Substances Data: 10061-02-6(Hazardous Substances Data)

Usage

General Description

(E)-1,3-Dichloro-1 -propene, also known as 1,3-Dichloropropene or Telone, is a colorless to pale yellow liquid chemical compound. It is primarily used as a soil fumigant to control pests and pathogens in agricultural settings. It is also used in the manufacture of other chemicals and products such as polymers and pesticides. (E)-1,3-Dichloro-1 -propene is classified as a hazardous chemical due to its potential to cause skin and eye irritation and its toxic effects if ingested or inhaled. It should be handled and used with caution, and proper safety measures should be taken when working with this chemical.

InChI:InChI=1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+

Synthetic route

(Z)-1,3-dichloropropene (10061-01-5) → (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With bromine In methanol at 25℃; for 1h; Time; Solvent; Reagent/catalyst; Temperature; UV-irradiation;	43.7%

3,3-dichloropropene (563-57-5) → (Z)-1,3-dichloropropene (10061-01-5) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With iron(III) chloride

3-chloroprop-1-ene (107-05-1) → (Z)-1,3-dichloropropene (10061-01-5) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With chlorine at 500℃;

methanol (67-56-1) + 1,2,3-trichloropropane (96-18-4) → 2,3-Dichloroprop-1-ene (78-88-6) + 1,2-Dichlor-3-methoxy-propane (34680-34-7) + (Z)-1,3-dichloropropene (10061-01-5) + 2-chloro-3-methoxypropene (32804-08-3) + cis-1-chloro-3-methoxypropene + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With aluminium at 250℃; Product distribution; Mechanism; other temp.;

chlorine (7782-50-5) + 3-chloroprop-1-ene (107-05-1) → 2,3-Dichloroprop-1-ene (78-88-6) + (Z)-1,3-dichloropropene (10061-01-5) + 3,3-dichloropropene (563-57-5) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
at 510℃; nach Vorwaermen auf 100grad;
at 510℃; nach Vorwaermen auf 100grad;

1-chloro-propene ( mixture of/the/ stereoisomer(ic)/s) → (Z)-1,3-dichloropropene (10061-01-5) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With chlorine at 560℃;

Trifluoromethylsulfenyl chloride (421-17-0) + 2-propynyl chloride (624-65-7) → (E)-1,3-dichloro-prop-1-ene (10061-02-6) + 1-trifluoromethylthio-2,3-dichloro-1-propene + bis(1,3-trifluoromethylthio)-cis-(1,2-dichloro)-1-propene + bis(1,3-trifluoromethylthio)-trans-(1,2-dichloro)-1-propene

Conditions	Yield
In pentane at -78 - 20℃; Further byproducts given. Title compound not separated from byproducts;

1,3-Dichloropropane (142-28-9) + 1-chloro-3-hydroxypropane (627-30-5) → glycidyl methyl ether (930-37-0) + 1,2-Epoxyhexane (1436-34-6) + 2,3-Dichloroprop-1-ene (78-88-6) + 2-chloroallyl alcohol (5976-47-6) + 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + (Z)-1,3-dichloropropene (10061-01-5) + 1,2,3-trichloro-1-propene (13116-58-0) + (1Z)-1,2,3-trichloroprop-1-ene (96-19-5, 13116-58-0, 13116-57-9) + 1,3,3-trichloro-propene (2953-50-6) + 1t,3,3-trichloro-propene (2598-01-8) + chlorodibromomethane (124-48-1) + 1,1,2-trichloropropane (598-77-6) + 2,3-Dichloro-1-propanol (616-23-9) + 1,3-Dichloro-2-propanol (96-23-1) + 1,2,3-trichloropropane (96-18-4) + 3,3-dichloropropene (563-57-5) + 3,3-dichloroallyl chloride (2567-14-8) + acetaldehyde (75-07-0) + allyl alcohol (107-18-6) + hydroxy-2-propanone (116-09-6) + chloroacetone (78-95-5) + cyclopentanone (120-92-3) + chlorobenzene (108-90-7) + isopropyl alcohol (67-63-0) + 3-monochloro-1,2-propanediol (96-24-2) + acrolein (107-02-8) + epichlorohydrin (106-89-8) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Conditions	Yield
With sodium hydroxide; water at 45 - 62.4℃; under 112.511 - 750.075 Torr; Product distribution / selectivity;

...Expand

phenylmagnesium bromide + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (1E)-1,3-diphenylpropene (3412-44-0)

Conditions	Yield
[Li(tmeda)]2[Fe(C2H4)4] In tetrahydrofuran at -20℃;	98%
Stage #1: (E)-1,3-dichloro-prop-1-ene; [Fe(C2H4)4][Li(tmeda)]2 In tetrahydrofuran at -20℃; Stage #2: phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -20℃; Further stages.;	96%

(E)-1,3-dichloro-prop-1-ene (10061-02-6) → (E)-(3-chloroallyl)phosphonic dichloride (70589-82-1)

Conditions	Yield
With aluminum (III) chloride; phosphorus trichloride at 45℃; Inert atmosphere;	97%

N-methyl-1-naphthalenemethylamine (14489-75-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (2E)-3-chloro-N-methyl-N-(naphthalen-1-ylmethyl)prop-2-en-1-amine (134865-58-0)

Conditions	Yield
With potassium carbonate In butanone at 50 - 85℃; for 7h;	96.5%
With potassium carbonate; potassium iodide In acetonitrile at 20℃;	81%
With potassium carbonate; potassium iodide In acetonitrile at 20℃;	81%
With potassium carbonate In acetonitrile at 20℃; for 5h; Reflux;	80%

[N-(tert-butyloxycarbonyl)amino]-2,4-dimethoxy-6-iodo-5-(methoxymethoxy)-3-methylbenzene (227084-62-0) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → [N-(tert-butyloxycarbonyl)-N-(3-chloro-2-propen-1-yl)amino]-2,4-dimethoxy-6-iodo-5-(methoxymethoxy)-3-methylbenzene (252204-14-1)

Conditions	Yield
Stage #1: [N-(tert-butyloxycarbonyl)amino]-2,4-dimethoxy-6-iodo-5-(methoxymethoxy)-3-methylbenzene With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Metallation; Stage #2: (E)-1,3-dichloro-prop-1-ene In N,N-dimethyl-formamide at 25℃; for 3h; Alkylation;	96%

methyl 8-(benzyloxy)-6-(N-(tert-butyloxycarbonyl)amino)-5-iodoquinoline-3-carboxylate (227084-56-2) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate (280573-11-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 12h; Alkylation;	94%

morpholine (110-91-8) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 1-[(2E)-3-chloroprop-2-en-1-yl]morpholine (59352-47-5)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 4h;	92%

(E)-1,3-dichloro-prop-1-ene (10061-02-6) → (E)-3-chloroallyl alcohol (4643-06-5)

Conditions	Yield
With sodium carbonate In water at 120℃; for 12h; Temperature; Reagent/catalyst;	91%
With potassium carbonate In water at 100℃; for 6h;	69%
With potassium hydroxide
With sodium carbonate
With sodium hydroxide; phosphate buffer at 25℃; pH=5.9; Kinetics; Further Variations:; pH-values;

1-(4-fluorophenyl)methyl-piperazine (27469-60-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-chloroprop-2-en-1-yl]piperazine

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 4.5h; Reflux;	91%

ethanamine hydrochloride (557-66-4) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (2E)-3-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-N-ethylprop-2-en-1-amine

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃; for 16h;	90%
With potassium carbonate In acetonitrile Heating; Reflux;	73%

piperidine (110-89-4) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 1-[(2E)-3-chloroprop-2-en-1-yl]piperidine

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 4h;	89%
With potassium carbonate; potassium iodide In acetonitrile for 6h; Heating;	87%

(E)-1,3-dichloro-prop-1-ene (10061-02-6) → E-3-bromo-1-chloropropene (67546-50-3)

Conditions	Yield
With sodium bromide In acetonitrile for 24h; Heating / reflux;	89%

iminodicarboxylic acid di-tert-butyl ester (51779-32-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → N,N-di-t-butoxycarbonyl-3-chloro-prop-2-en-1-amine (351330-25-1)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 6h; Heating;	88%

acetoacetic acid methyl ester (105-45-3) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → methyl (E)-7-chloro-3-oxohept-6-enoate

Conditions	Yield
Stage #1: acetoacetic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 1h; Stage #2: (E)-1,3-dichloro-prop-1-ene In tetrahydrofuran at -78 - 20℃; for 18h;	87%

1-(1,1-dimethylethyl)-2-methyl 5-[[(1,1-dimethylethoxy)-carbonyl]amino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate (919535-06-1) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 1-(1,1-dimethylethyl)-2-methyl 5-[(3-chloro-2-propenyl)-(1,1-dimethylethoxy)carbonylamino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate (919535-10-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h;	86%

Ethyl isovalerate (108-64-5) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → C10H17ClO2 (324519-65-5)

Conditions	Yield
Stage #1: With n-hexyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 0.5h; Stage #2: Ethyl isovalerate In tetrahydrofuran; hexane at -20℃; for 0.666667h; Stage #3: (E)-1,3-dichloro-prop-1-ene With water; ammonium chloride; sodium iodide more than 3 stages;	84%

diethylamine (109-89-7) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (2E)-3-chloro-N,N-diethylprop-2-en-1-amine (1308293-07-3)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 4h;	84%

diisopropylamine (108-18-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → [(2E)-3-chloroprop-2-en-1-yl]diisopropylamine (1308293-09-5)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 4h;	84%

diphenylmethylpiperazine (841-77-0) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 1-[(2E)-3-chloroprop-2-en-1-yl]-4-(diphenylmethyl)piperazine

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 4.5h; Heating;	84%

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → ethyl 2-oxo-1-[(2E)-3-chloroprop-2-en-1-yl]cyclopentane-1-carboxylate

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile at 50℃; for 8h;	84%
With 18-crown-6 ether; potassium carbonate In acetonitrile at 50℃; for 8h;	84%

(E)-1,3-dichloro-prop-1-ene (10061-02-6) + phosphorous acid trimethyl ester (121-45-9) → ((E)-3-Chloro-allyl)-phosphonic acid dimethyl ester

Conditions	Yield
at 110℃; Arbusov reaction;	83%

5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione (72651-95-7) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 5-(3-chloro-allyl)-5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione (1358791-91-9)

Conditions	Yield
With potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile at 50 - 55℃; for 12h;	82.1%

dimethyl isopropylmalonate (51122-91-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropyl malonate (705259-97-8)

Conditions	Yield
Stage #1: dimethyl isopropylmalonate With potassium hydroxide; tetrabutylammomium bromide In toluene for 0.166667h; Stage #2: (E)-1,3-dichloro-prop-1-ene In toluene at 30 - 35℃; for 4h; Product distribution / selectivity;	82%
In DMF (N,N-dimethyl-formamide); toluene at 90℃; for 2h;
Stage #1: dimethyl isopropylmalonate With sodium methylate In methanol; N,N-dimethyl-formamide at 60℃; for 0.5 - 1h; Stage #2: (E)-1,3-dichloro-prop-1-ene In methanol; N,N-dimethyl-formamide at 80℃; for 2.5 - 3h; Product distribution / selectivity;
Stage #1: dimethyl isopropylmalonate With sodium methylate In methanol at 95 - 105℃; Heating; Stage #2: (E)-1,3-dichloro-prop-1-ene In sulfolane; toluene at 95 - 105℃; for 2h; Product distribution / selectivity;
Stage #1: dimethyl isopropylmalonate With sodium methylate In methanol; toluene at 65 - 95℃; Heating; Stage #2: (E)-1,3-dichloro-prop-1-ene In sulfolane; toluene at 95 - 105℃; for 2h; Product distribution / selectivity;

benzyl-methyl-amine (103-67-3) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (E)-N-benzyl-N-methyl-3-chloroprop-2-ene-1-ylamine (173321-72-7)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 20℃;	81%
With potassium carbonate; potassium iodide In acetonitrile for 6h; Heating;	81%

benzoyl chloride (98-88-4) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (E)-S-3-chloroallyl benzothioate

Conditions	Yield
With potassium carbonate; thiourea In water at 30℃; for 8h;	81%

ethyl butyroyl acetate (3249-68-1) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → ethyl (4E)-2-butyryl-5-chloropent-4-enoate

Conditions	Yield
Stage #1: ethyl butyroyl acetate With aluminum oxide; potassium tert-butylate for 1h; Inert atmosphere; Stage #2: (E)-1,3-dichloro-prop-1-ene	81%

ethyl acetoacetate (141-97-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → ethyl (4E)-2-acetyl-5-chloropent-4-enoate

Conditions	Yield
Stage #1: ethyl acetoacetate With aluminum oxide; potassium tert-butylate for 1h; Inert atmosphere; Stage #2: (E)-1,3-dichloro-prop-1-ene	79%

3-phenyl-propionaldehyde (104-53-0) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (3R,4S)-4-chloro-1-phenylhex-5-en-3-ol

Conditions

Yield

Stage #1: (E)-1,3-dichloro-prop-1-ene With trichlorosilane; tetrabutylammomium bromide; triethylamine; copper(I) bromide In dichloromethane at 0℃; for 2h; Inert atmosphere; Stage #2: With 2-(tert-butyl)-6-((((1R,2R)-2-(methylamino)cyclohexyl)amino)methyl)phenol; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 23℃; for 1h; Inert atmosphere; Stage #3: 3-phenyl-propionaldehyde enantioselective reaction; Further stages;

78%

morpholine (110-91-8) + hex-1-yne (693-02-7) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → 4-[(2E)-non-2-en-4-yn-1-yl]morpholine

Conditions	Yield
Stage #1: morpholine; (E)-1,3-dichloro-prop-1-ene With copper(l) iodide; PdCl2(PrCN)2 at 20℃; for 0.5h; Inert atmosphere; Stage #2: hex-1-yne at 20℃; for 3h; Sonogashira Cross-Coupling;	78%
Stage #1: morpholine; (E)-1,3-dichloro-prop-1-ene at 20℃; for 1h; Stage #2: With copper(l) iodide; PdCl2(PrCN)2 at 20℃; for 0.5h; Inert atmosphere; Stage #3: hex-1-yne With morpholine at 20℃; for 3h; Sonogashira Cross-Coupling; Inert atmosphere;	78%

1-butyn-4-ol (927-74-2) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → (6E)-7-chlorohept-6-en-3-yn-1-ol

Conditions	Yield
With copper(l) iodide; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl acetamide at 50℃; stereoselective reaction;	77%

Ethyl isovalerate (108-64-5) + diisopropylamine (108-18-9) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → C10H17ClO2

Conditions	Yield
Stage #1: diisopropylamine With n-butyllithium In tetrahydrofuran at -15℃; for 0.5h; BuLi was added at -15 °ree;C in hexane over a period of 10 min; Stage #2: Ethyl isovalerate In tetrahydrofuran at -15℃; for 0.0833333h; Stage #3: (E)-1,3-dichloro-prop-1-ene With sodium iodide at 20℃; for 16h;	76%

Upstream product

• 563-57-5 3,3-dichloropropene 
• 67-56-1 methanol 
• 96-18-4 1,2,3-trichloropropane 
• 10061-01-5 cis-1,3-Dichloropropene 
• 142-28-9 1,3-Dichloropropane 
• 627-30-5 1-chloro-3-hydroxypropane 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 624-65-7 2-propynyl chloride 
• 7782-50-5 chlorine 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 109392-07-6 1-Chloro-3-acetoxypropene 
• 99584-97-1 allyl-(3t-chloro-allyl)-amine 
• 3412-44-0 (1E)-1,3-diphenylpropene 
• 5209-18-7 cis-1,3-diphenylpropene 
• 1219366-88-7 C₁₁H₁₁ClO₃ 
• 324519-65-5 C₁₀H₁₇ClO₂ 
• 87953-16-0 (4E)-5-chloro-2-isopropyl-4-pentenoic acid 
• 475562-17-5 methyl (4E)-5-chloro-2-isopropyl-4-pentenoate 
• 705259-97-8 dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropyl malonate 
• 67546-50-3 E-3-bromo-1-chloropropene 
• 919535-10-7 1-(1,1-dimethylethyl)-2-methyl 5-[(3-chloro-2-propenyl)-(1,1-dimethylethoxy)carbonylamino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate 

Relevant articles and documents

Reaction of trifluoromethylsulfenyl chloride with 3-chloro- and 3-hydroxypropynes

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