67330-62-5

Basic information

• Product Name: 3-CHLORO-2,6-DIETHYLANILINE
• Synonyms: Aniline,3-chloro-2,6-diethyl- (6CI);3-CHLORO-2,6-DIETHYLANILINE;TIMTEC-BB SBB003723;3-Chloro-2,6-diethylbenzenamine;3-CHLORO-2,6-DIETHYLANILINE 98+%;5-chloro-2,6-diethylaniline
• CAS NO: 67330-62-5
• Molecular Formula: C₁₀H₁₄ClN
• Molecular Weight: 183.68
• Product Categories: Amines;C9 to C10;Nitrogen Compounds
• Mol File: 67330-62-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 137-139 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.095 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00438mmHg at 25°C
• Refractive Index: n20/D 1.56(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.08±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-2,6-DIETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-2,6-DIETHYLANILINE(67330-62-5)
• EPA Substance Registry System: 3-CHLORO-2,6-DIETHYLANILINE(67330-62-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 23-26-28-36
• RIDADR: PG3
• WGK Germany: 3
• Hazardous Substances Data: 67330-62-5(Hazardous Substances Data)

Usage

Uses

3-Chloro-2,6-diethylaniline may be used in chemical synthesis.

InChI:InChI=1/C10H14ClN/c1-3-7-5-6-9(11)8(4-2)10(7)12/h5-6H,3-4,12H2,1-2H3

Synthetic route

acetic acid-(2,6-diethyl-3-chloro-anilide) (104851-50-5) → 2,6-diethyl-3-chloro-aniline (67330-62-5)

Conditions	Yield
With sulfuric acid

ethene (74-85-1) + 3-chloro-aniline (108-42-9) → 2,6-diethyl-3-chloro-aniline (67330-62-5)

Conditions	Yield
With aluminium
With aluminium trichloride; aluminium
With aluminium trichloride; aluminium at 250℃; under 147837 Torr;

N-(2,6-diethylphenyl)acetamide (16665-89-7) → 2,6-diethyl-3-chloro-aniline (67330-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; chlorine 2: aqueous H2SO4 View Scheme
Multi-step reaction with 3 steps 1: aqueous KClO 2: acetic acid 3: aqueous H2SO4 View Scheme

acetic acid-(2,6-diethyl-N-chloro-anilide) (104851-74-3) → 2,6-diethyl-3-chloro-aniline (67330-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid 2: aqueous H2SO4 View Scheme

2,6-diethylaniline (579-66-8) → 2,6-diethyl-3-chloro-aniline (67330-62-5)

Conditions	Yield
Stage #1: 2,6-diethylaniline With sulfuric acid; chlorine at 30℃; for 3h; Autoclave; Stage #2: With sodium hydroxide In water Product distribution / selectivity;	94.4 %Chromat.

2,6-diethylaniline (579-66-8) → 2,6-diethyl-3-chloro-aniline (67330-62-5) + 3,5-dichloro-2,6-diethylaniline

Conditions	Yield
Stage #1: 2,6-diethylaniline With sulfuric acid; chlorine at 35℃; for 4.5h; autoclave; Stage #2: With sodium hydroxide In water	A 8.3 %Chromat. B 71.2 %Chromat.
Stage #1: 2,6-diethylaniline With chlorosulfonic acid; chlorine at 30℃; for 3h; autoclave; Stage #2: With sodium hydroxide In water	A 18.6 %Chromat. B 10.5 %Chromat.

2-Iodo-N,N-dimethylbenzamide (54616-46-5) + 2,6-diethyl-3-chloro-aniline (67330-62-5) → 2-(3-chloro-2,6-diethyl-phenylamino)-N,N-dimethyl-benzamide (269061-78-1)

Conditions	Yield
With copper(l) iodide; copper; potassium carbonate In xylene Condensation; Heating;	58%

2,6-diethyl-3-chloro-aniline (67330-62-5) → 3-chloro-2,6-diethyl-5-nitro-phenylamine (916585-89-2)

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; for 2.5h;	50%

2,6-diethyl-3-chloro-aniline (67330-62-5) + 7-hydroxy-naphthalene-1,3-disulfonyl chloride (872271-34-6) → N1,N3-di(3-chloro-2,6-diethylphenyl)-7-hydroxynaphthalene-1,3-disulfonamide

Conditions	Yield
In acetonitrile for 4h; Heating / reflux;	4%

thiophosgene (463-71-8) + 2,6-diethyl-3-chloro-aniline (67330-62-5) → 3-Chlor-2,6-diaethyl-phenylisothiocyanat (67330-49-8)

Conditions	Yield
With calcium carbonate In dichloromethane; water
With water; calcium carbonate
With water; calcium carbonate In dichloromethane Heating;
With water; calcium carbonate In dichloromethane

2,6-diethyl-3-chloro-aniline (67330-62-5) → [2-(3-chloro-2,6-diethyl-phenylamino)-phenyl]-methanol (269061-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / K2CO3; Cu; CuI / xylene / Heating 2: 82 percent / LiEt3BH / tetrahydrofuran / 20 °C View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → [2-(3-chloro-2,6-diethyl-phenylamino)-benzyl]-phosphonic acid dimethyl ester (269061-92-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / K2CO3; Cu; CuI / xylene / Heating 2: 82 percent / LiEt3BH / tetrahydrofuran / 20 °C 3: 62 percent / MsOH / CH2Cl2 / 20 °C View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → [2-(3-chloro-2,6-diethyl-phenylamino)-benzyl]-phosphonic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 58 percent / K2CO3; Cu; CuI / xylene / Heating 2: 82 percent / LiEt3BH / tetrahydrofuran / 20 °C 3: 62 percent / MsOH / CH2Cl2 / 20 °C 4: 72 percent / trimethylsilyl bromide / CH2Cl2 View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → 1-tert-Butyl-3-(3-chloro-2,6-diethyl-phenyl)-thiourea (67330-84-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; calcium carbonate / dichloromethane / Heating View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → 1-(3-Chloro-2,6-diethyl-phenyl)-3-(1,1-dimethyl-propyl)-thiourea (67355-08-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; calcium carbonate / dichloromethane / Heating View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → 1-sec-Butyl-3-(3-chloro-2,6-diethyl-phenyl)-thiourea (67330-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; calcium carbonate / dichloromethane / Heating View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → N-(3-Chlor-2,6-diaethylphenyl)-N'-butylthioharnstoff (68065-56-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium carbonate / dichloromethane; water View Scheme
Multi-step reaction with 2 steps 1: water; calcium carbonate View Scheme
Multi-step reaction with 2 steps 1: water; calcium carbonate / dichloromethane View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → N-(3-Chlor-2,6-diaethylphenyl)-N'-neopentylthioharnstoff (68065-57-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium carbonate / dichloromethane; water View Scheme
Multi-step reaction with 2 steps 1: water; calcium carbonate View Scheme
Multi-step reaction with 2 steps 1: water; calcium carbonate / dichloromethane View Scheme

formaldehyd (50-00-0) + 2,6-diethyl-3-chloro-aniline (67330-62-5) + 2-isopropyl-6-methylaniline (5266-85-3) → 4,4'-methylene-bis-(3-chloro-2,6-diethylaniline) (106246-33-7) + M-MIPACDEA (1332763-78-6) + methylene-1,1-bis(2-isopropyl-6-methylaniline) (16298-38-7)

Conditions	Yield
With sulfuric acid In water; isopropyl alcohol at 60℃; for 6h;

2,6-diethyl-3-chloro-aniline (67330-62-5) → C11H12Cl2N2O3

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 °C 2: sodium carbonate / acetonitrile / 2 - 7 h / 20 °C View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → 3-(3-amino-5-chloro-2,6-diethyl-phenyl)-1-(4-ethyl-phenyl)-1-(6-methyl-pyridin-3yl-methyl)-urea (916585-90-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 °C 2: sodium carbonate / acetonitrile / 2 - 7 h / 20 °C 3: acetonitrile / 16 h / 20 °C 4: hydrogen / palladium on activated charcoal / methanol / 0.17 - 1 h / 20 °C View Scheme

2,6-diethyl-3-chloro-aniline (67330-62-5) → C26H29ClN4O3

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 °C 2: sodium carbonate / acetonitrile / 2 - 7 h / 20 °C 3: acetonitrile / 16 h / 20 °C View Scheme

Upstream product

• 74-85-1 ethene 
• 108-42-9 3-chloro-aniline 
• 579-66-8 2,6-diethylaniline 
• 104851-74-3 acetic acid-(2,6-diethyl-N-chloro-anilide) 
• 16665-89-7 N-(2,6-diethylphenyl)acetamide 
• 104851-50-5 acetic acid-(2,6-diethyl-3-chloro-anilide) 

Downstream Products

• 269061-78-1 2-(3-chloro-2,6-diethyl-phenylamino)-N,N-dimethyl-benzamide 
• 916585-89-2 3-chloro-2,6-diethyl-5-nitro-phenylamine 
• 916585-90-5 3-(3-amino-5-chloro-2,6-diethyl-phenyl)-1-(4-ethyl-phenyl)-1-(6-methyl-pyridin-3yl-methyl)-urea 
• 106246-33-7 4,4'-methylene-bis-(3-chloro-2,6-diethylaniline) 
• 1332763-78-6 M-MIPACDEA 
• 16298-38-7 methylene-1,1-bis(2-isopropyl-6-methylaniline) 
• 68065-57-6 N-(3-Chlor-2,6-diaethylphenyl)-N'-neopentylthioharnstoff 
• 68065-56-5 N-(3-Chlor-2,6-diaethylphenyl)-N'-butylthioharnstoff 
• 67330-85-2 1-sec-Butyl-3-(3-chloro-2,6-diethyl-phenyl)-thiourea 
• 67355-08-2 1-(3-Chloro-2,6-diethyl-phenyl)-3-(1,1-dimethyl-propyl)-thiourea 
• 67330-84-1 1-tert-Butyl-3-(3-chloro-2,6-diethyl-phenyl)-thiourea 
• 269061-92-9 [2-(3-chloro-2,6-diethyl-phenylamino)-benzyl]-phosphonic acid dimethyl ester 
• 269061-84-9 [2-(3-chloro-2,6-diethyl-phenylamino)-phenyl]-methanol 
• 67330-49-8 3-Chlor-2,6-diaethyl-phenylisothiocyanat 

Relevant articles and documents

PROCESS FOR THE SELECTIVE META-CHLORINATION OF ALKYLANILINES

A process for the chlorination of alkylanilines is provided allowing a highly selective chlorination in the meta-position of the aromatic ring. This is achieved by reacting a mixture comprising the alkylaniline and sulfuric acid with chlorine. This process allows a meta-chlorination with a selectivity of more than 90%.