36961-64-5

Basic information

• Product Name: 2-(2-Chloroethoxy)Acetamide
• Synonyms: 2-CHLOROETHOXY-ACETAMIDE;N-(2-Chloroethoxy)-acetamide;2-(2-Chloroethoxy)acetamide
• CAS NO: 36961-64-5
• Molecular Formula: C₄H₈ClNO₂
• Molecular Weight: 137.56
• Mol File: 36961-64-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 72-75 °C
• Boiling Point: 289.3 °C at 760 mmHg
• Flash Point: 128.8 °C
• Appearance: /
• Density: 1.216 g/cm³
• Vapor Pressure: 0.00222mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 15.47±0.40(Predicted)
• CAS DataBase Reference: 2-(2-Chloroethoxy)Acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Chloroethoxy)Acetamide(36961-64-5)
• EPA Substance Registry System: 2-(2-Chloroethoxy)Acetamide(36961-64-5)

Safety Data

• Hazardous Substances Data: 36961-64-5(Hazardous Substances Data)

Usage

General Description

2-(2-Chloroethoxy)Acetamide is a chemical compound with the formula C4H8ClNO2. It is a white crystalline solid and is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It is also used as a crosslinking agent in the manufacturing of polymers and resins. The chemical is known to be stable under normal temperature and pressure, but should be stored in a cool, dry place away from direct sunlight and sources of ignition. It is important to handle this chemical with proper safety precautions, as it can cause irritation to the skin, eyes, and respiratory system if not handled properly.

InChI:InChI=1/C4H8ClNO2/c5-1-2-8-3-4(6)7/h1-3H2,(H2,6,7)

Synthetic route

2-(2-hydroxyethoxy)-acetamide (123-85-3) → 2-(2-chloroethoxy)acetamide (36961-64-5)

Conditions	Yield
With pyridine; thionyl chloride In chloroform; water	91%

2-(2-chloroethoxy)acetamide (36961-64-5) + N-(4-chlorobenzhydryl)piperazine (303-26-4) → 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide (83881-37-2, 163837-41-0, 163837-43-2)

Conditions	Yield
Stage #1: N-(4-chlorobenzhydryl)piperazine With tetrabutylammomium bromide; potassium carbonate In water at 25℃; Stage #2: 2-(2-chloroethoxy)acetamide In water at 80℃;	95%
With potassium iodide; sodium chloride; sodium carbonate; sodium sulfate In di-isopropyl ether; water; toluene	79.6%

4-ethoxycarbonylpiperazine (120-43-4) + 2-(2-chloroethoxy)acetamide (36961-64-5) → ethyl 4-(2-carbamoylmethoxyethyl)piperazine-1-carboxylate

Conditions	Yield
With potassium iodide; sodium carbonate In isopropyl alcohol; toluene	82%

2-(2-chloroethoxy)acetamide (36961-64-5) + N-(4-chlorobenzhydryl)piperazine (303-26-4) → dihydrochloride of 2-[2-[4-[(4-chlorophenyl) phenylmethyl-1-piperazinyl]ethoxy]acetamide + 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide (83881-37-2, 163837-41-0, 163837-43-2)

Conditions	Yield
With potassium iodide; sodium chloride; sodium carbonate In para-xylene; water; toluene	A 78.8% B n/a

diphenylmethylpiperazine (841-77-0) + 2-(2-chloroethoxy)acetamide (36961-64-5) → 2-[2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy]-acetamide + 2-[2-[4-Diphenylmethyl)-1-piperazinyl]ethoxy]-acetamide dihydrochloride

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene; water; benzene	A 73% B n/a

piperazine (110-85-0) + 2-(2-chloroethoxy)acetamide (36961-64-5) + piperazine dihydrochloride (142-64-3) → 2-[2-(1-piperazinyl)ethoxy]acetamide (197968-56-2)

Conditions	Yield
With ammonium hydroxide In methanol; ethanol; dichloromethane; water; butanone	57.1%

piperazine (110-85-0) + 2-(2-chloroethoxy)acetamide (36961-64-5) → 2-[2-(1-piperazinyl)ethoxy]acetamide (197968-56-2)

Conditions	Yield
With ammonium hydroxide In toluene	39%

2-(2-chloroethoxy)acetamide (36961-64-5) + (+)-1-<(4-chlorophenyl)phenylmethyl>piperazine → (+)-2-(2-<4-<(4-chlorophenyl)phenylmethyl>-1-piperazinyl>ethoxy)acetamide

Conditions	Yield
With sodium carbonate; potassium iodide In toluene

2-(2-chloroethoxy)acetamide (36961-64-5) + (-)-1-<(4-chlorophenyl)phenylmethyl>piperazine → (-)-2-(2-<4-<(4-chlorophenyl)phenylmethyl>-1-piperazinyl>ethoxy)acetamide

Conditions	Yield
With sodium carbonate; potassium iodide In toluene

4-ethoxycarbonylpiperazine (120-43-4) + 2-(2-chloroethoxy)acetamide (36961-64-5) → ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylate

Conditions	Yield
With potassium iodide; sodium carbonate In ethyl acetate; isopropyl alcohol; toluene

2-(2-chloroethoxy)acetamide (36961-64-5) + 1-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazine → 2-(2-{4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

2-(2-chloroethoxy)acetamide (36961-64-5) + 1-{(S)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazine (346417-35-4) → 2-[2-(4-{(S)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide (346415-25-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

2-(2-chloroethoxy)acetamide (36961-64-5) + 1-{(S)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazine (551943-94-3) → 2-[2-(4-{(S)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide (346417-73-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

2-(2-chloroethoxy)acetamide (36961-64-5) + 1-{(R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazine (551943-93-2) → 2-[2-(4-{(R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide (346417-74-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

2-(2-chloroethoxy)acetamide (36961-64-5) + 1-{(R)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazine (551943-95-4) → 2-[2-(4-{(R)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide (346417-75-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

2-(2-chloroethoxy)acetamide (36961-64-5) + 1-(4-fluorophenyl)methyl-piperazine (27469-60-9) → (2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxy)acetamide (197968-98-2)

Conditions	Yield
With sodium carbonate In xylene at 140℃; for 4h; Heating / reflux;

methanol (67-56-1) + 1-phenylmethylpiperazine (2759-28-6) + 2-(2-chloroethoxy)acetamide (36961-64-5) → 2-(4-benzyl-1-piperazinyl)ethoxyacetamide

Conditions	Yield
With potassium iodide; sodium carbonate In dichloromethane; water; butanone

morpholine (110-91-8) + 2-(2-chloroethoxy)acetamide (36961-64-5) + pyrographite (7440-44-0) → 2-(2-morpholinoethoxy)acetamide hydrochloride

Conditions	Yield
With sodium iodide In hydrogenchloride; toluene

potassium phthalimidate + 2-(2-chloroethoxy)acetamide (36961-64-5) → 2-(2-phthalimidoethoxy)acetamide

Conditions	Yield
In N-methyl-acetamide

2-(2-chloroethoxy)acetamide (36961-64-5) + (S)-1-((4-chlorophenyl)(phenyl)methyl)piperazine (439858-21-6) → [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetamide hydrochloride

Conditions	Yield
Stage #1: 2-(2-chloroethoxy)acetamide; 1-[(S)-(4-chlorophenyl)(phenyl)methyl]piperazine With potassium carbonate; potassium iodide In N,N-dimethyl-formamide; toluene at 25 - 110℃; Stage #2: With hydrogenchloride In Isopropyl acetate; N,N-dimethyl-formamide; acetone; toluene at 10 - 15℃; pH=1 - 2;

(-)-1-[(4-chloro-phenyl)-phenyl-methyl]-4-(4-methoxy-benzyl)piperazine (1198162-46-7) + 2-(2-chloroethoxy)acetamide (36961-64-5) → (+)-Cetirizine dihydrochloride

Conditions	Yield
Stage #1: (-)-1-[(4-chloro-phenyl)-phenyl-methyl]-4-(4-methoxy-benzyl)piperazine; 2-(2-chloroethoxy)acetamide With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 25 - 110℃; Stage #2: With hydrogenchloride In ipa pH=1 - 2;

Upstream product

• 123-85-3 2-(2-hydroxyethoxy)-acetamide 

Downstream Products

• 130018-87-0 (+)-Cetirizine dihydrochloride 
• 83881-37-2 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide 
• 197968-56-2 2-[2-(1-piperazinyl)ethoxy]acetamide 
• 197968-98-2 (2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxy)acetamide 
• 346417-75-2 2-[2-(4-{(R)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide 
• 346417-74-1 2-[2-(4-{(R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide 
• 346417-73-0 2-[2-(4-{(S)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide 
• 346415-25-6 2-[2-(4-{(S)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-1-phenyl-ethyl}-piperazin-1-yl)-ethoxy]-acetamide 

Relevant articles and documents

4-Homoisotwistane derivatives

A new class of 4-homoisotwistane derivatives of the formula, STR1 wherein R1 is a hydrogen atom or a C1 -C3 alkyl group, and R2 is an alkyl group, a phenyl group which may be either unsubstituted or substituted with a C1 -C3 alkyl, C1 -C3 alkoxy, nitro group or a halogen atom (hereinafter referred to as "an optionally substituted phenyl group"), a group of the formula, --A--OH in which A is a C1 -C3 alkylene group; a group of the formula, --A--B in which A is as defined as above and B is a halogen atom, or a group of the formula, STR2 in which A is as defined above and R3 and R4 are independently a hydrogen atom or a C1 -C3 alkyl group or R3 and R4 may, when taken together with the adjacent nitrogen atom to which R3 and R4 are linked, form pyrrolidine, piperidine, morpholine, phthalimide or piperazine, which have been found to possess potent antiviral activity, are prepared, for example by reacting a compound of the formula, STR3 wherein R1 is as defined above and X is halogen, with a compound of the formula, wherein R5 has the same meanings as R2 with the exception of the group of the formula --A--B wherein A and B are as defined above and Y is alkali metal.