14869-41-1

Basic information

• Product Name: 2-CHLOROETHOXY ACETIC ACID
• Synonyms: 2-CHLOROETHOXY ACETIC ACID;2-(2-chloroethoxy)acetic acid;Acetic acid, 2-(2-chloroethoxy)-;2-(Chloroethoxyl)acetic acid;Chloro-PEG-CH2COOH;5-Chloro-3-oxapentanoic acid
• CAS NO: 14869-41-1
• Molecular Formula: C₄H₇ClO₃
• Molecular Weight: 136.58
• EINECS: 1312995-182-4
• Mol File: 14869-41-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 32.5-33.0 °C
• Boiling Point: 289.753 °C at 760 mmHg
• Flash Point: 129.038 °C
• Appearance: Brown crystal
• Density: 1.296 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.45
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.34±0.10(Predicted)
• CAS DataBase Reference: 2-CHLOROETHOXY ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROETHOXY ACETIC ACID(14869-41-1)
• EPA Substance Registry System: 2-CHLOROETHOXY ACETIC ACID(14869-41-1)

Safety Data

• Hazardous Substances Data: 14869-41-1(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Uses

A metabolite of Bis(2-chloroethyl) Ether.

InChI:InChI=1/C4H7ClO3/c5-1-2-8-3-4(6)7/h1-3H2,(H,6,7)

Synthetic route

1,4-dioxane (123-91-1) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With dipotassium peroxodisulfate; thionyl chloride at 25℃; for 4h;	96.1%
With hydrogenchloride; sodium hypochlorite

tert-butyl 2-(2-chloroethoxy)acetate → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With hydrogenchloride; water for 2h;	95%

(2-chloro-ethoxy)-acetic acid ethyl ester (17229-14-0) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran	90%

2-(2-Chloroethoxy)ethanol (628-89-7) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In acetone at 0℃; for 6h;	77%
With sodium periodate; ruthenium trichloride In water; acetonitrile at 20℃; for 16h;	74%
Stage #1: 2-(2-Chloroethoxy)ethanol With calcium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.5h; Stage #2: With sodium metabisulfite In dichloromethane; water	72%

2-chloroethyl cyanomethyl ether (31250-08-5) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With hydrogenchloride

carbon dioxide (124-38-9) + (2-chloroethoxy)magnesium chloride (821-50-1) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
In tetrahydrofuran at -60℃;

1-chloro-2-(2-nitro-ethoxy)-ethane (28547-59-3) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With hydrogenchloride

diethylene glycol (111-46-6) → (2-chloroethoxy)-acetic acid (14869-41-1)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite

(2-chloroethoxy)-acetic acid (14869-41-1) + 4-fluoro-2-methoxy-5-nitro-phenylamine (1075705-01-9) → 2-(2-chloroethoxy)-N-(4-fluoro-2-methoxy-5-nitrophenyl)acetamide

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide	99%

brecanavir (313682-08-5) + (2-chloroethoxy)-acetic acid (14869-41-1) → (1R,2S)-2-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-1-{[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]methyl}-3-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}propyl (2-chloroethoxy)acetate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 24h;	92%

(2-chloroethoxy)-acetic acid (14869-41-1) + butan-1-ol (71-36-3) → 2-Chlor-aethoxyesssigsaeure-butylester (68448-72-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	91%

(2-chloroethoxy)-acetic acid (14869-41-1) + 2-(1-aminopiperidin-4-yl)isoindoline-1,3-dione → 2-(2-chloroethoxy)-N-(4-(1,3-dioxoisoindolin-2-yl)piperidin-1-yl)acetamide

Conditions	Yield
Stage #1: (2-chloroethoxy)-acetic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 30℃; for 0.333333h; Stage #2: 2-(1-aminopiperidin-4-yl)isoindoline-1,3-dione In N,N-dimethyl-formamide at 30℃; for 16h;	89.3%

(2-chloroethoxy)-acetic acid (14869-41-1) → 2-(2-chloroethoxy)acetyl chloride (39229-33-9)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide	88%
With thionyl chloride; N,N-dimethyl-formamide at 25 - 70℃; for 20h;	83%
With thionyl chloride; N,N-dimethyl-formamide at 60℃; for 1 - 16h; Product distribution / selectivity;	82%

(2-chloroethoxy)-acetic acid (14869-41-1) + (R)-1-((4-chlorophenyl)(phenyl)methyl)piperazine (300543-56-0) → levocetirizine (130018-77-8)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydride In N,N-dimethyl-formamide at 95℃; for 5h; Inert atmosphere;	86.5%

(2-chloroethoxy)-acetic acid (14869-41-1) + 4-nitro-aniline (100-01-6) → 4-(2-(2-chloroethoxy)acetamido)1-nitrobenzene (811450-82-5)

Conditions	Yield
With phenylboronic acid In toluene at 110 - 111℃; Dean-Stark; Reflux;	83%

(2-chloroethoxy)-acetic acid (14869-41-1) + methyl 5-(((allyloxy)carbonyl)(1-aminopiperidin-4-yl)carbamoyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate → methyl 5-(((allyloxy)carbonyl)(1-(2-(2-chloroethoxy)acetamido)piperidin-4-yl)carbamoyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 25℃; for 16.5h;	79%

(2-chloroethoxy)-acetic acid (14869-41-1) + (S)-5-[2-[3-(3-chloro-2-fluorophenyl)-1H-pyrazole-3-carboxamido]-3-(4-aminophenyl)-propionamido] -1H-indole-2-carboxylic acid ethyl ester → (S)-ethyl 5-(2-(5-(3-chloro-2-fluorophenyl)-1H-pyrazole-3-carboxamido)-3-(4-(3-oxomorpholino)phenyl)-propanamido)-1H-indole-2-carboxylate

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 60℃; for 4h;	76%
Stage #1: (2-chloroethoxy)-acetic acid; (S)-5-[2-[3-(3-chloro-2-fluorophenyl)-1H-pyrazole-3-carboxamido]-3-(4-aminophenyl)-propionamido] -1H-indole-2-carboxylic acid ethyl ester With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 60℃; for 4h; Inert atmosphere; Stage #2: With sodium hydride In tetrahydrofuran at 20 - 30℃; for 5h; Inert atmosphere;	76%

(2-chloroethoxy)-acetic acid (14869-41-1) + (S)-2-{4-[(methoxycarbonyl)amino]benzamido}-3-(4-aminophenyl)propionic acid methyl ester → (S)-2-(4-((methoxycarbonyl)amino)benzamido)-3-(4-(3-oxomorpholin-4-yl)phenyl)propionic acid methyl ester

Conditions	Yield
Stage #1: (2-chloroethoxy)-acetic acid; (S)-2-{4-[(methoxycarbonyl)amino]benzamido}-3-(4-aminophenyl)propionic acid methyl ester With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 60℃; for 4h; Stage #2: With sodium hydride In tetrahydrofuran at 20℃; for 5h;	76%

(2-chloroethoxy)-acetic acid (14869-41-1) + 2-bromo-4-fluoro-5-nitrophenylamine (346433-97-4) → N-(2-bromo-4-fluoro-5-nitrophenyl)-2-(2-chloroethoxy)acetamide

Conditions	Yield
Stage #1: (2-chloroethoxy)-acetic acid With pyridine; thionyl chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-bromo-4-fluoro-5-nitrophenylamine With dmap; triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;	51%

(2-chloroethoxy)-acetic acid (14869-41-1) + ethyl 6-(3-amino-3-azabicyclo[3.1.0]hexan-6-yl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate → ethyl 6-(3-(2-(2-chloroethoxy)acetamido)-3-azabicyclo[3.1.0]hexan-6-yl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

Conditions

Yield

Stage #1: (2-chloroethoxy)-acetic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 25℃; for 0.5h; Stage #2: ethyl 6-(3-amino-3-azabicyclo[3.1.0]hexan-6-yl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate In dichloromethane at 25℃; for 16h;

50%

piperazine (110-85-0) + (2-chloroethoxy)-acetic acid (14869-41-1) + piperazine dihydrochloride (142-64-3) → 2-(1-piperazinyl)ethoxyacetic acid dihydrochloride

Conditions	Yield
With ammonium acetate; hydrogenchloride In ethanol; water; isopropyl alcohol	12%

(2-chloroethoxy)-acetic acid (14869-41-1) → p-dioxanone (3041-16-5)

Conditions	Yield
With sodium hydroxide unter vermindertem Druck;

methanol (67-56-1) + (2-chloroethoxy)-acetic acid (14869-41-1) → (2-Chloro-ethoxy)-acetic acid methyl ester (83881-47-4)

Conditions	Yield
With thionyl chloride

(2-chloroethoxy)-acetic acid (14869-41-1) + (2R)-2-[(2R)-4-(4-aminophenyl)-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamde (1228772-75-5) → (2R)-N-(4-cyanophenyl)-2-hydroxy-2-[(2R)-3-oxo-4-[4-(3-oxomorpholin-4-yl)phenyl]morpholin-2-yl]acetamide (1228772-88-0)

Conditions	Yield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In N,N-dimethyl-formamide at 20℃;

(2-chloroethoxy)-acetic acid (14869-41-1) → 4-chloro-2-oxabutanyl-1-phosphonic acid (1391871-33-2)

Conditions	Yield
With phosphorus(III) oxide; methanesulfonic acid at 20 - 30℃; for 2h;
Stage #1: (2-chloroethoxy)-acetic acid With phosphorus trichloride In chlorobenzene at 50℃; for 4h; Inert atmosphere; Stage #2: With water In chlorobenzene Inert atmosphere;

(2-chloroethoxy)-acetic acid (14869-41-1) + C22H28N6O2S2 → C26H33ClN6O4S2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; acetonitrile at 0 - 25℃; for 18h;	484 mg

(2-chloroethoxy)-acetic acid (14869-41-1) + 6-(1-aminopiperidin-4-yl)-3-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one → 2-(2-chloroethoxy)-N-(4-(7-oxo-3-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridin-6(7H)-yl)piperidin-1-yl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 12℃; for 16h;	2.8 g

(2-chloroethoxy)-acetic acid (14869-41-1) + 6-(1-aminopiperidin-4-yl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one → 2-(2-chloroethoxy)-N-(4-(1-(4-methoxyphenyl)-7-oxo-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridin-6(7H)-yl)piperidin-1-yl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 16h;	900 mg

(2-chloroethoxy)-acetic acid (14869-41-1) + ethyl 6-(1-aminopiperidin-4-yl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3, 4-c]pyridine-3-carboxylate → ethyl 6-(1-(2-(chloromethoxy)acetamido)piperidin-4-yl)-1-(4-methoxyphenyl)-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 12h;

Upstream product

• 31250-08-5 2-chloroethyl cyanomethyl ether 
• 111-46-6 diethylene glycol 
• 17229-14-0 (2-chloro-ethoxy)-acetic acid ethyl ester 
• 628-89-7 2-(2-Chloroethoxy)ethanol 
• 123-91-1 1,4-dioxane 
• 28547-59-3 1-chloro-2-(2-nitro-ethoxy)-ethane 
• 124-38-9 carbon dioxide 
• 821-50-1 (2-chloroethoxy)magnesium chloride 

Downstream Products

• 39229-33-9 2-(2-chloroethoxy)acetyl chloride 
• 3041-16-5 p-dioxanone 
• 83881-47-4 (2-Chloro-ethoxy)-acetic acid methyl ester 
• 130018-77-8 levocetirizine 
• 811450-82-5 4-(2-(2-chloroethoxy)acetamido)1-nitrobenzene 
• 1228772-88-0 (2R)-N-(4-cyanophenyl)-2-hydroxy-2-[(2R)-3-oxo-4-[4-(3-oxomorpholin-4-yl)phenyl]morpholin-2-yl]acetamide 

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