3383-72-0

Basic information

• Product Name: 1-(2-Chloroethoxy)-4-nitrobenzene
• Synonyms: BETA-CHLORO-4-NITROPHENETHOLE;2-(4-NITROPHENOXY)ETHYL CHLORIDE;1-(2-CHLOROETHOXY)-4-NITROBENZENE;2-CHLOROETHYL-4-NITROPHENYL ETHER;β-chloro-4-nitrophenethole;1-(2-CHLOROETHOXY)4-NITROBENZENE, 98+%;4-Nitro-1-(2-chloroethoxy)benzene;4-(2-Chloroethoxy)nitrobenzene
• CAS NO: 3383-72-0
• Molecular Formula: C₈H₈ClNO₃
• Molecular Weight: 201.61
• EINECS: 425-790-8
• Product Categories: API intermediates
• Mol File: 3383-72-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 67-68 °C
• Boiling Point: 332.1 °C at 760 mmHg
• Flash Point: 154.6 °C
• Appearance: needle-like crystal
• Density: 1.316 g/cm³
• Vapor Pressure: 0.000288mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-(2-Chloroethoxy)-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chloroethoxy)-4-nitrobenzene(3383-72-0)
• EPA Substance Registry System: 1-(2-Chloroethoxy)-4-nitrobenzene(3383-72-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 9-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 3383-72-0(Hazardous Substances Data)

Usage

General Description

1-(2-Chloroethoxy)-4-nitrobenzene is an organic compound with the chemical formula C8H8ClNO3. It consists of a benzene ring with a nitro group (NO2) and an ethoxy group (OCH2CH2Cl) attached to it. 1-(2-Chloroethoxy)-4-nitrobenzene is commonly used in the synthesis of pharmaceuticals, dyes, and other organic compounds. It is a colorless to pale yellow liquid with a strong odor, and it is considered to be a potentially hazardous chemical. 1-(2-Chloroethoxy)-4-nitrobenzene is often handled and stored with precautions due to its potential health hazards and should be used in a well-ventilated environment with proper personal protective equipment.

InChI:InChI=1/C8H8ClNO3/c9-5-6-13-8-3-1-7(2-4-8)10(11)12/h1-4H,5-6H2

Synthetic route

4-nitro-phenol (100-02-7) + 1-Bromo-2-chloroethane (107-04-0) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	84%
With caesium carbonate In ethanol at 80℃; for 8h;	66%
With potassium carbonate In acetonitrile Heating;

sodium tetrakis(2-chloroethoxy)borate + 4-chlorobenzonitrile (100-00-5) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In tert-Amyl alcohol at 100℃; for 1h; Inert atmosphere;	80%

4-nitro-phenol (100-02-7) + 1,2-dichloro-ethane (107-06-2) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With potassium carbonate In butanone for 36h; Heating;	72%
With potassium carbonate In ethyl methyl ether for 36h; Heating / reflux;

2-(4-nitrophenoxy)ethanol (16365-27-8) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With phosphorus pentachloride at 100℃;
With thionyl chloride; methylpyridine; benzene
With thionyl chloride for 3h; Heating / reflux;
With pyridine; thionyl chloride In 1,4-dioxane for 2h;

1,2-dichloro-ethane (107-06-2) + 4-nitrophenol sodium salt (824-78-2) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

4-(4-nitrophenoxy)butanoic acid (28341-54-0) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous ethanol / 120 °C 2: PCl5 / 100 °C View Scheme

2-(4-nitrophenoxy)ethanol (16365-27-8) + sodium hydrogencarbonate (144-55-8) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
In thionyl chloride
In thionyl chloride
In thionyl chloride
In thionyl chloride

4-nitro-phenol (100-02-7) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With potassium carbonate In 2-butanone, 2-chloroethyl-p-toluenesulfonate
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 8 h / 80 °C / Inert atmosphere 2: thionyl chloride; pyridine / 1,4-dioxane / 2 h View Scheme
Multi-step reaction with 2 steps 1: sodium iodide; potassium carbonate; caesium carbonate / N,N-dimethyl-formamide 2: thionyl chloride View Scheme

4-nitro-phenol (100-02-7) + 2-chloroethyl benzenesulfonate (16670-48-7) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With potassium carbonate In methyl ethyl ketone ("MEK"-1000 ml)
With potassium carbonate In butanone

oxirane (75-21-8) + 4-nitro-phenol (100-02-7) + 2-(4-nitrophenoxy)ethanol (16365-27-8) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With thionyl chloride In N-methyl-acetamide; ice-water

4-nitro-phenol (100-02-7) + 2-chloro-ethanol (107-07-3) → 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0)

Conditions	Yield
With potassium hydroxide In water

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + (4-nitro-phenyl)-piperazin-1-yl-methanone (72141-41-4) → {4-[2-(4-nitro-phenoxy)-ethyl]-piperazin-1-yl}-(4-nitro-phenyl)-methanone (329003-83-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile Heating;	94%

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 4-(2'-chloroethoxy)-aniline (27692-35-9)

Conditions	Yield
With tin(ll) chloride In ethanol; water at 70℃; for 2h;	90%
With iron; ammonium chloride In ethanol at 80℃; for 1h;	73%
With iron; ammonium chloride In ethanol; water at 80℃; for 1h;	73%
With hydrogen; platinum(IV) oxide In ethanol
With hydrogen; platinum(IV) oxide In ethanol at 20℃;

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride (87691-88-1) → 3-{4-[2-(4-nitro-phenoxy)-ethyl]-piperazin-1-yl}-1,2-benzisothiazole (690978-22-4)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 150℃; for 1.5h; Microwave irradiation;	89%

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + acetic anhydride (108-24-7) → 2-(4-acetamidophenoxy)ethyl chloride (36616-28-1)

Conditions	Yield
With acetic acid; zinc at 80℃; for 6h;	88%

4-piperidinemethanol (6457-49-4) + 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → {1-[2-(4-nitro-phenoxy)-ethyl]-piperidin-4-yl}-methanol (1374585-74-6)

Conditions	Yield
In ISOPROPYLAMIDE at 60℃;	86%

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + N-methyl-N-[2-(4-nitro-phenyl)-ethyl]-amine (85176-37-0) → 1-(4-nitrophenoxy)-2-ethane (115287-37-1)

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile for 72h; Heating;	64%
With sodium iodide; potassium carbonate In acetonitrile

4-((1R,2R,6S,7S)-1,7-dimethyl-3,5-dioxo-11-oxa-4,9-diaza-tricyclo[5.3.1.02,6]undec-4-yl)-2-trifluoromethyl-benzonitrile (934418-72-1) + 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 4-{(1R,2R,6S,7S)-1,7-dimethyl-9-[2-(4-nitro-phenoxy)-ethyl]-3,5-dioxo-11-oxa-4,9-diazatricyclo[5.3.1.02,6]undec-4-yl}-2-trifluoromethylbenzonitrile

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 100℃; for 72h;	48%

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + malononitrile oxime ether sodium salt (19166-62-2) → C11H8N4O4

Conditions	Yield
In acetonitrile at 80℃;	40%

formaldehyd (50-00-0) + 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → (2-chloro-ethyl)-(2-chloromethyl-4-nitro-phenyl)-ether

Conditions	Yield
With hydrogenchloride; acetic acid weiteres Edukt: ZnCl2;

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + Normeperidine (77-17-8) → 1-[2-(4-nitro-phenoxy)-ethyl]-4-phenyl-piperidine-4-carboxylic acid ethyl ester (114158-57-5)

Conditions	Yield
With pentan-1-ol; sodium carbonate

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + diethylamine (109-89-7) → diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine (19881-36-8)

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + aniline (62-53-3) → N-<2-(p-nitrophenoxy)ethyl>aniline (25836-86-6)

Conditions	Yield
With sodium hydroxide
at 150 - 180℃;

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 4-nitrophenylvinylether (940-14-7)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol
With potassium tert-butylate Kinetics;

1H-imidazole (288-32-4) + 1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 1-(4-nitrophenyl)-1H-imidazole (2301-25-9) + 1-[2-(4-nitro-phenoxy)ethyl]-1H-imidazole (75912-69-5)

Conditions	Yield
With sodium hydride 1.) DMF, 100 deg C, 10 min, 2.) DMF, heating, 5.5 h; Yield given. Yields of byproduct given;

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + 5-methoxy-1,2-dihydro-indazol-3-one (99719-37-6) → 5-methoxy-1-[2-(4-nitrophenoxy)ethyl]-1H-indazole-3-ol (197584-30-8)

Conditions	Yield
With sodium hydroxide Heating;

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + N,N-dimethylammonium chloride (506-59-2) → N,N-dimethyl-2-(4-nitrophenoxy)ethylamine (51344-13-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 2,6-dimethylphenyl (2,4-dimethoxyphenyl)-(2-((4-((2-(dimethylamino)ethyl)oxy)phenyl)amino)-4-pyrimidinyl)carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / acetonitrile / 80 °C 2: H2 / Pd/C / ethanol / 16 h / 20 °C 3: 40 percent / trifluoroacetic acid / propan-2-ol / 24 h / 100 °C View Scheme

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 4-<2-(dimethylamino)ethoxy>aniline (62345-76-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 80 °C 2: H2 / Pd/C / ethanol / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 20 °C View Scheme

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 4-(2-chloroethoxy)-2-nitroaniline (681259-29-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / Zn; acetic acid / 6 h / 80 °C 2: 68 percent / aq. HNO3 / 1 h / Heating 3: 75 percent / aq. HCl / 4 h / Heating View Scheme

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → N-[4-(2-chloroethoxy)-2-nitrophenyl]acetamide (672961-06-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / Zn; acetic acid / 6 h / 80 °C 2: 68 percent / aq. HNO3 / 1 h / Heating View Scheme

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 5-[2-(4-phenyl-piperazin-1-yl)-ethoxy]-1H-benzotriazole

Conditions	Yield
Multi-step reaction with 6 steps 1: 88 percent / Zn; acetic acid / 6 h / 80 °C 2: 68 percent / aq. HNO3 / 1 h / Heating 3: 75 percent / aq. HCl / 4 h / Heating 4: 70 percent / K2CO3; KI / dimethylformamide / 24 h / 80 °C 5: Ra-Ni; hydrazine hydrate / ethanol; 1,2-dichloro-ethane / 1 h / 50 °C 6: 58 percent / aq. sodium nitrite; acetic acid / 0 - 70 °C View Scheme

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 5-[2-(4-phenylpiperazin-1-yl)-ethoxy]-1H-benzoimidazol

Conditions	Yield
Multi-step reaction with 6 steps 1: 88 percent / Zn; acetic acid / 6 h / 80 °C 2: 68 percent / aq. HNO3 / 1 h / Heating 3: 75 percent / aq. HCl / 4 h / Heating 4: 70 percent / K2CO3; KI / dimethylformamide / 24 h / 80 °C 5: Ra-Ni; hydrazine hydrate / ethanol; 1,2-dichloro-ethane / 1 h / 50 °C 6: 62 percent / H2O / 2 h / 100 °C View Scheme

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) → 4-[2-(4-phenylpiperazin-1-yl)-ethoxy]-benzene-1,2-diamine (681259-59-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 88 percent / Zn; acetic acid / 6 h / 80 °C 2: 68 percent / aq. HNO3 / 1 h / Heating 3: 75 percent / aq. HCl / 4 h / Heating 4: 70 percent / K2CO3; KI / dimethylformamide / 24 h / 80 °C 5: Ra-Ni; hydrazine hydrate / ethanol; 1,2-dichloro-ethane / 1 h / 50 °C View Scheme

Upstream product

• 100-02-7 4-nitro-phenol 
• 107-06-2 1,2-dichloro-ethane 
• 107-04-0 1-Bromo-2-chloroethane 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 144-55-8 sodium hydrogencarbonate 
• 75-21-8 oxirane 
• 100-00-5 4-chlorobenzonitrile 
• 16670-48-7 2-chloroethyl benzenesulfonate 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 824-78-2 4-nitrophenol sodium salt 
• 107-07-3 2-chloro-ethanol 

Downstream Products

• 19881-36-8 diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine 
• 36616-28-1 2-(4-acetamidophenoxy)ethyl chloride 
• 27692-35-9 4-(2'-chloroethoxy)-aniline 
• 159184-13-1 1-(2-Azidoethoxy)-4-nitrobenzene 
• 65300-53-0 4-[2-(4-nitrophenoxy)ethyl]morpholine 
• 92033-76-6 1-[2-(1-piperidinyl)ethoxy]4-nitrobenzene 
• 265654-77-1 1-(2-(4-nitrophenoxy)ethyl)pyrrolidine 
• 51344-13-9 N,N-dimethyl-2-(4-nitrophenoxy)ethylamine 

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