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

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

Uses

Used in Agricultural Industry:
(E)-1,3-Dichloro-1-propene is used as a soil fumigant for controlling pests and pathogens in agricultural settings. It is effective in protecting crops from various soil-borne diseases and pests, thereby ensuring a healthy and productive agricultural yield.
Used in Chemical Manufacturing:
(E)-1,3-Dichloro-1-propene is used as a key component in the production of other chemicals, polymers, and pesticides. Its versatility in chemical synthesis allows for the creation of a wide range of products that serve various purposes in different industries.
Used in Pesticide Production:
(E)-1,3-Dichloro-1-propene is used as an active ingredient in the formulation of pesticides. Its ability to control pests and pathogens makes it a valuable component in the development of effective and efficient pest control solutions for agricultural and other applications.

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

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

Downstream Products

• 252204-14-1 [N-(tert-butyloxycarbonyl)-N-(3-chloro-2-propen-1-yl)amino]-2,4-dimethoxy-6-iodo-5-(methoxymethoxy)-3-methylbenzene 
• 55704-81-9 2-acetoxy-1,1,3-trichloropropane 
• 76937-36-5 2-fluoro-1,1,3-trichloropropane 
• 67832-44-4 1RS, 2SR-1-fluoro-1,2,3-trichloropropane 
• 55704-82-0 1RS, 2SR-1-acetoxy-1,2,3-trichloropropane 
• 67832-45-5 erythro-1,2-Dibrom-1,3-dichlorpropan 
• 99584-97-1 allyl-(3t-chloro-allyl)-amine 
• 109392-07-6 1-Chloro-3-acetoxypropene 
• 4643-06-5 (E)-3-chloroallyl alcohol 
• 21960-87-2 bis-(3t-chloro-allyl)-ether 
• 16136-85-9 trans-1-Chloropropen 
• 59036-45-2 (E)-[(3-chloroprop-2-en-1-yl)sulfanyl]benzene 
• 5209-18-7 cis-1,3-diphenylpropene 
• 3412-44-0 (1E)-1,3-diphenylpropene 

Relevant articles and documents

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