628-89-7

Basic information

• Product Name: 2-(2-Chloroethoxy)ethanol
• Synonyms: DIETHYLENE GLYCOL CHLOROHYDRIN;DIETHYLENE GLYCOL MONOCHLOROHYDRIN;ETHYLENE GLYCOL MONO-2-CHLOROETHYL ETHER;2-(2-CHLOROETHOXY)ETHANOL;2-CHLOROETHOXYETHANOL;2-(2-chloroethoxy)-ethano;2-Chloro-2’-hydroxydiethylether;2-Chloroethyl 2-hydroxyethyl ether
• CAS NO: 628-89-7
• Molecular Formula: C₄H₉ClO₂
• Molecular Weight: 124.57
• EINECS: 211-059-9
• Product Categories: Alkohols;Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols;Alcohols;C2 to C6;Oxygen Compounds;Quetiapine
• Mol File: 628-89-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 79-81 °C5 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: Clear/Liquid
• Density: 1.18 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.234mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 2-8°C
• Solubility: SOLUBLE
• PKA: 14.34±0.10(Predicted)
• Water Solubility: SOLUBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 506015
• CAS DataBase Reference: 2-(2-Chloroethoxy)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Chloroethoxy)ethanol(628-89-7)
• EPA Substance Registry System: 2-(2-Chloroethoxy)ethanol(628-89-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36-39
• RIDADR: UN 3334
• WGK Germany: 2
• RTECS: KK1350000
• F: 19
• TSCA: Yes
• Hazardous Substances Data: 628-89-7(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 628-89-7 differently. You can refer to the following data:
1. 2-(2-Chloroethoxy)ethanol is a degradation product of Bis(2-Chloroethyl) Ether. 2-(2-Chloroethoxy)ethanol is a potential genotoxic impurity (PGI) in active pharmaceutical ingredients (APIs).
2. 2-(2-Chloroethoxy)ethanol is employed in the preparation of o-nitrophenylbromoacetaldehyde bis-2-(2-chloroethoxy)-ethyl acetal, quetiapine and 2-(2-azidoethoxy)ethanol.
3. 2-(2-Chloroethoxy)ethanol was used in the synthesis of o-nitrophenylbromoacetaldehyde bis-2-(2-chloroethoxy)-ethyl acetal, quetiapine (an antipsychotic drug) and 2-(2-azidoethoxy)ethanol.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H9ClO2/c5-1-3-7-4-2-6/h6H,1-4H2

Synthetic route

oxirane (75-21-8) + 2-chloro-ethanol (107-07-3) → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With sulfuric acid bei Siedetemperatur;
at 140℃;
With sulfuric acid

oxirane (75-21-8) → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With hydrogenchloride

ethylene glycol (107-21-1) + 2-chloro-ethanol (107-07-3) → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
at 140℃; Erkalten mit HCl-Gas gesaettigt und Erhitzen auf 100grad;

ethylene glycol (107-21-1) + 2-chloro-ethanol (107-07-3) → 2-(2-(2-(2-chloroethoxy)ethoxy)ethoxy)ethanol (5197-66-0) + 2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
at 140℃;

2-(2-chloroethoxy)ethyl ethanoate (14258-40-3) → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With hydrogenchloride; methanol

diethylene glycol (111-46-6) → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With pyridine; thionyl chloride
With hydrogenchloride; sulfuric acid; zinc(II) chloride at 160℃; for 7h;

1,4-dioxane (123-91-1) → 2-(2-(2-(2-chloroethoxy)ethoxy)ethoxy)ethanol (5197-66-0) + 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With titanium tetrachloride 1.) 20 deg C, 2.) reflux, 7 d;	A 150 mg B 55 mg

2-chloromethyl-1,3-dioxolane (2568-30-1) → ethylene glycol (107-21-1) + 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2-chloromethyl-1,3-dioxolane (2568-30-1) → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction;

3-oxa-1,5-dichloropentane (111-44-4) → 1,4-dioxane (123-91-1) + 2-chloroethanal (107-20-0) + acetaldehyde (75-07-0) + 2-(2-Chloroethoxy)ethanol (628-89-7) + 1,2-dichloro-ethane (107-06-2) + 2-chloro-ethanol (107-07-3)

Conditions	Yield
In neat (no solvent) at 130 - 190℃; for 0.1h; Product distribution; thermal conversion; in presence of water, various time;

1-(2-Chloro-ethoxy)-2-nitrosooxy-ethane → 2-(2-Chloroethoxy)ethanol (628-89-7)

Conditions	Yield
With potassium chloride In 1,4-dioxane at 28℃; Rate constant; phosphate buffer pH 7.6;

oxirane (75-21-8) + sulfuric acid (7664-93-9) + 2-chloro-ethanol (107-07-3) → 1,4-dioxane (123-91-1) + 2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + 2-(2-Chloroethoxy)ethanol (628-89-7)

2-chloro-ethanol (107-07-3) → 1,4-dioxane (123-91-1) + 2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + 2-(2-Chloroethoxy)ethanol (628-89-7) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + HCl, water

Conditions	Yield
at 150℃; for 5h; Product distribution; Kinetics; Rate constant; dependence of the products of ECH decomposition on temperature in sealed tube at 115, 130, 140, 150, 160 deg C;

2-(2-Chloroethoxy)ethanol (628-89-7) → 2-(2-azidoethoxy)ethanol (139115-90-5)

Conditions	Yield
With sodium azide; sodium iodide In water at 60℃; for 96h;	100%
With sodium azide In water at 80℃; for 16h; Inert atmosphere;	99%
With sodium azide In water at 80℃; for 18h;	99%

2,4,6-tris(benzyloxy)-1,3,5-triazine (7285-83-8) + 2-(2-Chloroethoxy)ethanol (628-89-7) → benzyl (2-(2-chloroethoxy)ethyl) ether (64352-98-3)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 7h; Inert atmosphere;	100%

2-(2-Chloroethoxy)ethanol (628-89-7) + tert-butyl (4-(4-hydroxyphenyl)butyl)carbamate (465529-53-7) → C20H33NO5

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile	100%

4-hydroxy-4'-nitrobenzophenone (18920-70-2) + 2-(2-Chloroethoxy)ethanol (628-89-7) → (4-(2-(2-hydroxyethoxy)ethoxy)phenyl)(4-nitrophenyl)methanone

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 65 - 70℃; for 16h; Sealed tube;	100%

2-(2-Chloroethoxy)ethanol (628-89-7) + 1-{2-[2-(2-azidoethoxy)ethoxy]ethyl}piperazine TFA salt → C14H29N5O4

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile Reflux;	100%

2-(4-(dimethylamino)phenyl)-6-hydroxy-4H-chromen-4-one (887646-88-0) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 6-(2-(2-hydroxyethoxy)ethoxy)-4'-dimethylaminoflavone (1147337-36-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 11h;	99.3%

3,4-dihydro-2H-pyran (110-87-2) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 2-(2-(2-chloroethoxy)ethoxy)tetrahydro-2H-pyran (54533-84-5)

Conditions	Yield
With hydrogenchloride	99%
at 0 - 20℃; for 6h;	99%
With hydrogenchloride at 20℃; for 1h; Etherification;	98%

1,5-dihydroxynaphthalene (83-56-7) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1,5-bis[2-(2-hydroxyethoxy)ethoxy]naphthalene (136133-14-7)

Conditions	Yield
With potassium carbonate In acetonitrile at 82℃;	99%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;	75%
With potassium carbonate In N,N-dimethyl-formamide Heating;	67%

1,1'-biphenyl-3,3'-diol (612-76-0) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 3,3'-bis(5-hydroxy-3-oxa-1-pentyloxy)-1,1'-biphenyl (929886-87-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h;	99%

tert-butyldimethylsilyl chloride (18162-48-6) + 2-(2-Chloroethoxy)ethanol (628-89-7) → tert-butyl (2-(2-chloroethoxy)ethoxy)dimethylsilane (119382-85-3)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 16h;	99%
With 1H-imidazole In acetonitrile at 20℃;	92%

2-(2-Chloroethoxy)ethanol (628-89-7) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2) → 1-[2-(2-hydroxyethoxy)ethyl]-1,8-diazabicyclo[5.4.0]undec-7-ene chloride

Conditions	Yield
In acetonitrile at 75℃; for 24h; Inert atmosphere;	99%
In ethyl acetate at 80℃; for 24h; Inert atmosphere;	95%

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride (753475-15-9) + 2-(2-Chloroethoxy)ethanol (628-89-7) → Quetiapine (111974-69-7)

Conditions	Yield
With sodium carbonate; sodium iodide; tetrabutylammomium bromide In toluene at 115 - 120℃; for 17h; Heating / reflux;	98.2%
With sodium carbonate; sodium iodide; tetrabutylammomium bromide In butan-1-ol at 115 - 120℃; for 17h; Heating / reflux;	96.9%
With sodium carbonate; sodium iodide In butan-1-ol at 115 - 120℃; for 17h; Heating / reflux;	94.1%

benzene-1,2-diol (120-80-9) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1,2-bis[2-(2-hydroxyethoxy)ethoxy]benzene (41757-99-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;	98%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 75℃; for 72h;	88.4%
Stage #1: benzene-1,2-diol With potassium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; Stage #2: 2-(2-Chloroethoxy)ethanol With potassium iodide In N,N-dimethyl-formamide at 100℃; for 144h; Inert atmosphere;	85.5%

2,2'-dihydroxybiphenyl (1806-29-7) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 2,2'-bis(5-hydroxy-3-oxa-1-pentyloxy)-1,1'-biphenyl (91859-84-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h;	98%

2-(2-Chloroethoxy)ethanol (628-89-7) + methyl 4-hydroxylbenzoate (99-76-3) → methyl 4-[2-(2-hydroxyethoxy)ethoxy]-benzoate (159550-14-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	98%
With potassium carbonate; potassium iodide In cyclohexanone for 24h; Inert atmosphere; Reflux;	66%
With caesium carbonate; potassium iodide In cyclohexanone for 24h; Reflux;
With caesium carbonate; potassium iodide for 24h; Reflux;

2-(2-Chloroethoxy)ethanol (628-89-7) + benzyl alcohol (100-51-6) → benzyl (2-(2-chloroethoxy)ethyl) ether (64352-98-3)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold (I) at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation;	98%

N-methyl-perfluorobutane-1-sulfonamide (68298-12-4) + 2-(2-Chloroethoxy)ethanol (628-89-7) → C9H12F9NO4S

Conditions	Yield
With potassium carbonate at 90 - 120℃; for 17.25h;	97.8%

2-(2-Chloroethoxy)ethanol (628-89-7) + m-bis(2-(p-hydroxyphenyl)-1,10-phenanthrolinyl)benzene (159726-86-0) → 2-[2-(4-{9-[3-(9-{4-[2-(2-Hydroxy-ethoxy)-ethoxy]-phenyl}-[1,10]phenanthrolin-2-yl)-phenyl]-[1,10]phenanthrolin-2-yl}-phenoxy)-ethoxy]-ethanol

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	97%
With caesium carbonate 1.) DMF, 80 deg C, 1 h, 2.) DMF, 80 deg C, 6 h; Yield given; Multistep reaction;

2-(2-Chloroethoxy)ethanol (628-89-7) + chlorophosphoric acid diphenyl ester (2524-64-3) → 2-(2-chloro-ethoxy)-ethyldiphenylphosphate (1232681-87-6)

Conditions	Yield
With molybdenum(VI) tetrachloride oxide; triethylamine In dichloromethane at 20℃; for 1h;	97%

4-(4,6-diphenoxy-1,3,5-triazine-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate + 2-(2-Chloroethoxy)ethanol (628-89-7) → benzyl (2-(2-chloroethoxy)ethyl) ether (64352-98-3)

Conditions	Yield
With magnesium oxide In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere;	97%

DBN (3001-72-7) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1-[2-(2-hydroxyethoxy)ethyl]-1,5-diazabicyclo[4.3.0]non-5-ene chloride

Conditions	Yield
In ethyl acetate at 80℃; for 24h; Inert atmosphere;	97%

6-(4-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione + 2-(2-Chloroethoxy)ethanol (628-89-7) → 4-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)benzyl 2-(2-chloroethoxy)ethyl ether

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5h; Molecular sieve;	97%

1,4-bis[2-(4-hydroxyphenyl)-2-propylene]benzene (4084-45-1) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 2-(2-{4''-[2-(2-hydroxy-ethoxy)-ethoxy]-[1,1';4',1'']terphenyl-4-yloxy}-ethoxy)-ethanol

Conditions	Yield
With potassium carbonate; lithium bromide In N,N-dimethyl-formamide	96%

1-(3-hydroxyphenyl)pentan-1-one (62810-51-9) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1-(3-((2-((2-hydroxyethyl)oxy)ethyl)oxy)phenyl)-1-pentanone

Conditions	Yield
With potassium carbonate In acetone for 60h; Heating / reflux;	96%

4-Cyano-4'-hydroxybiphenyl (19812-93-2) + 2-(2-Chloroethoxy)ethanol (628-89-7) → C17H17NO3 (127972-30-9)

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 110℃; for 12h;	96%

piperazine (110-85-0) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1-[2-(2-hydroxyethoxy)ethyl]piperazine (13349-82-1)

Conditions	Yield
With piperazine dihydrochloride In ethanol for 10h; Reflux; Large scale;	95.1%
at 120 - 140℃; for 1h;	70%

5-tert-butyl-N,N'-bis(3-hydroxyphenyl)-1,3-benzenediamide (835875-06-4) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 5-tert-butyl-N,N'-bis-{3-[2-(2-hydroxyethoxy)ethoxy]phenyl}-1,3-benzenediamide (835875-09-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 120h; Heating;	95%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1-(3-((2-((2-hydroxyethyl)oxy)ethyl)oxy)phenyl)-1-propanone

Conditions	Yield
With potassium carbonate In acetone for 60h; Heating / reflux;	95%

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride (753475-15-9) + 2-(2-Chloroethoxy)ethanol (628-89-7) + (2E)-but-2-enedioic acid (110-17-8) → quetiapine fumarate

Conditions	Yield
Stage #1: 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride; 2-(2-Chloroethoxy)ethanol With sodium carbonate; sodium iodide In propan-1-ol; N,N-dimethyl-formamide at 10 - 20℃; for 24h; Heating / reflux; Stage #2: (2E)-but-2-enedioic acid In ethanol	95%
Stage #1: 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride; 2-(2-Chloroethoxy)ethanol With sodium carbonate; sodium iodide In 1-methyl-pyrrolidin-2-one; propan-1-ol for 24h; Heating / reflux; Stage #2: (2E)-but-2-enedioic acid In ethanol

2-(2-Chloroethoxy)ethanol (628-89-7) → 2-(2-mercaptoethoxy)ethanol (17643-17-3)

Conditions	Yield
Stage #1: 2-(2-Chloroethoxy)ethanol With thiourea; sodium iodide In acetonitrile at 20℃; for 72h; Reflux; Stage #2: With water; sodium hydroxide In ethanol for 24h; Reflux;	95%
Stage #1: 2-(2-Chloroethoxy)ethanol With thiourea In water at 100℃; for 18h; Inert atmosphere; Stage #2: With sodium hydroxide In water at 20 - 100℃; Stage #3: With hydrogenchloride In water pH=4; Inert atmosphere; Cooling with ice;	49%
With thiourea

Upstream product

• 107-21-1 ethylene glycol 
• 107-07-3 2-chloro-ethanol 
• 75-21-8 oxirane 
• 7664-93-9 sulfuric acid 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 2568-30-1 2-chloromethyl-1,3-dioxolane 
• 123-91-1 1,4-dioxane 
• 111-46-6 diethylene glycol 
• 14258-40-3 2-(2-chloroethoxy)ethyl ethanoate 

Downstream Products

• 13349-82-1 1-[2-(2-hydroxyethoxy)ethyl]piperazine 
• 41757-99-7 1,2-bis[2-(2-hydroxyethoxy)ethoxy]benzene 
• 54384-48-4 tris-[2-(2-hydroxy-ethoxy)-ethyl]-amine 
• 54384-47-3 2,2'-((azanediylbis(ethane-2,1-diyl))bis(oxy))diethanol 
• 616-21-7 1,2-dichlorobutane 
• 116941-29-8 1-(2-chloro-ethoxy)-2-(1-chloromethyl-propoxy)-ethane 
• 83076-78-2 6,9,12-triaza-3,15-dioxa-6,9,12-tritosylheptadecane-1,17-diol 
• 76980-41-1 3,12-dioxa-6,9-diaza-6,9-di(p-toluenesulfonyl)tetradecane-1,14-diol 
• 152488-72-7 C₂₅H₃₈N₂O₈S₂ 
• 107098-11-3 9-benzoyl-6,12-bis(p-tolylsulfonyl)-6,9,12-triaza-3,15-dioxaheptadecane-1,17-diol 
• 101241-23-0 1,3,4,6-tetrakis(7-(1-imidazolyl)-2,5-dioxaheptyl)tetrahydro-3a,6a-diphenylimidazo{4,5-d}imidazole-2,5(1H,3H)-dione 
• 113585-55-0 1,20-dihydroxy-6,15-dibenzyl-6,15-diaza-3,9,12,18-tetraoxaicosane 
• 127154-27-2 5-bromo-2-(5-hydroxy-3-oxapentyloxy)benzaldehyde 
• 127154-30-7 3,5-diiodo-2-(5-hydroxy-3-oxapentyloxy)benzaldehyde 

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