6967-29-9

Basic information

• Product Name: N-CHLOROACETYL-2,6-DIETHYLANILINE
• Synonyms: 2-chloro-N-(2,6-diethylphenyl)ethanamide;2-Chloro-N-(diethylphenyl)acetamide;Acetamide, 2-chloro-N-(2,6-diethylphenyl)-;N1-(2,6-DIETHYLPHENYL)-2-CHLOROACETAMIDE;2-CHLORO-2',6'-DIETHYLACETANILIDE;AKOS BBS-00004009;2-Chloro-N-(2,6-diethylphenyl)acetamide;Chloro-N-(2,6-diethylphenyl)acetamide
• CAS NO: 6967-29-9
• Molecular Formula: C₁₂H₁₆ClNO
• Molecular Weight: 225.71
• EINECS: 214-460-7
• Mol File: 6967-29-9.mol

Chemical Properties

• Melting Point: 128-130°C
• Boiling Point: 369.2 °C at 760mmHg
• Flash Point: 177.1 °C
• Appearance: White crystal
• Density: 1.131g/cm³
• Vapor Pressure: 1.2E-05mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.91±0.70(Predicted)
• Stability: Moisture Sensitive
• BRN: 2111384
• CAS DataBase Reference: N-CHLOROACETYL-2,6-DIETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CHLOROACETYL-2,6-DIETHYLANILINE(6967-29-9)
• EPA Substance Registry System: N-CHLOROACETYL-2,6-DIETHYLANILINE(6967-29-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 6967-29-9(Hazardous Substances Data)

Usage

Uses

2-?Chloro-?(N-?2,?6-?diethyl phenyl)?acetamide is a reagent used in the synthesis of novel inhibitors of signal transducer and activator of the transcription (STAT3) signalling pathway which is used in the treatment of cancers.

InChI:InChI=1/C12H16ClNO/c1-3-9-6-5-7-10(4-2)12(9)14-11(15)8-13/h5-7H,3-4,8H2,1-2H3,(H,14,15)

Synthetic route

2,6-diethylaniline (579-66-8) + chloroacetyl chloride (79-04-9) → 2-chloro-2',6'-diethylacetanilide (6967-29-9)

Conditions	Yield
In ethyl acetate for 2h; Acylation; Heating;	99.1%
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	82.72%
sodium acetate In acetic acid at 0℃; for 0.5h; Acylation;

Chloroiodomethane (593-71-5) + 2,6-diethylphenylisocyanate (20458-99-5) → 2-chloro-2',6'-diethylacetanilide (6967-29-9)

Conditions	Yield
With methyllithium lithium bromide In diethyl ether at -78℃;	95%
With methyllithium; lithium bromide In diethyl ether at -78℃; for 0.5h; chemoselective reaction;	95%

Alachlor (15972-60-8) → 2-chloro-2',6'-diethylacetanilide (6967-29-9)

Conditions	Yield
With hydrogenchloride In acetone for 4h; Hydrolysis; Heating;

2,6-diethylaniline (579-66-8) + chloroacetyl chloride (79-04-9) → 2-chloro-2',6'-diethylacetanilide (6967-29-9)

Conditions	Yield
In ethyl acetate for 2h; Acylation; Heating;	99.1%
With triethylamine In dichloromethane at 0 - 20℃; for 6h;	82.72%
sodium acetate In acetic acid at 0℃; for 0.5h; Acylation;

Chloroiodomethane (593-71-5) + 2,6-diethylphenylisocyanate (20458-99-5) → 2-chloro-2',6'-diethylacetanilide (6967-29-9)

Conditions	Yield
With methyllithium lithium bromide In diethyl ether at -78℃;	95%
With methyllithium; lithium bromide In diethyl ether at -78℃; for 0.5h; chemoselective reaction;	95%

Alachlor (15972-60-8) → 2-chloro-2',6'-diethylacetanilide (6967-29-9)

Conditions	Yield
With hydrogenchloride In acetone for 4h; Hydrolysis; Heating;

2-chloro-2',6'-diethylacetanilide (6967-29-9) + potassium phtalimide (1074-82-4) → 2-amino-2',6'-diethylacetanilide (70752-53-3)

Conditions	Yield
In N-methyl-acetamide	92%

1-ethoxy-2-chloromethoxyethane (69602-59-1) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → 2-Chloro-N-(2,6-diethyl-phenyl)-N-(2-ethoxy-ethoxymethyl)-acetamide (85211-82-1)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h;	90%

7-Hydroxy-2,2,5-trimethyl-4-chromanone (20052-60-2) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → N-(2,6-Diethyl-phenyl)-2-(2,2,5-trimethyl-4-oxo-chroman-7-yloxy)-acetamide (133035-38-8)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 6h; Heating;	86.4%

2,3-dihydro-7-hydroxy-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one (74094-45-4) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → N-(2,6-Diethyl-phenyl)-2-(6-methoxy-2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide (133035-55-9)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 6h; Heating;	80.3%

diisopropoxymethane (2568-89-0) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → 2-Chloro-N-(2,6-diethyl-phenyl)-N-isopropoxymethyl-acetamide (67535-24-4)

Conditions	Yield
With toluene-4-sulfonic acid for 5h; Heating;	60%

benzo[f]quinoline (85-02-9) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) + propynoic acid ethyl ester (623-47-2) → ethyl 3-[N-(2,6-diethylphenyl)carbamoyl]benzo[f]pyrrolo[1,2-a]quinoline-1-carboxylate

Conditions	Yield
With ethyloxirane at 120℃; for 2h; Sealed tube; Microwave irradiation;	39%
With ethyloxirane at 120℃; for 2h; Sealed tube; Microwave irradiation;	39%

2-chloro-2',6'-diethylacetanilide (6967-29-9) + thymidine 3'-monophosphate disodium salt → 3-[[N-(2,6-diethylphenyl)carbamoyl]methyl]thymidine 3'-monophosphate disodium salt

Conditions	Yield
With sodium hydrogencarbonate In 2-methoxy-ethanol; water at 82℃; for 24h; Addition;	36.2%

2-chloro-2',6'-diethylacetanilide (6967-29-9) + thymidine (50-89-5) → 3-[[N-(2,6-diethylphenyl)carbamoyl]methyl]thymidine

Conditions	Yield
With sodium hydrogencarbonate In 2-methoxy-ethanol at 45 - 50℃; for 336h; Addition;	26%

2-chloro-2',6'-diethylacetanilide (6967-29-9) + 2'-deoxyguanosine 3'-monophosphate disodium salt → 1-[[N-(2,6-diethylphenyl)carbamoyl]methyl]-2'-deoxyguanosine 3'-monophosphate

Conditions	Yield
With sodium hydrogencarbonate In 2-methoxy-ethanol; water at 75℃; for 24h; Addition;	14.7%

2-chloro-2',6'-diethylacetanilide (6967-29-9) + 2'-Deoxyguanosine (961-07-9) → 1-[[N-(2,6-diethylphenyl)carbamoyl]methyl]-2'-deoxyguanosine

Conditions	Yield
With sodium hydrogencarbonate In 2-methoxy-ethanol at 45 - 50℃; for 336h; Addition;	12%

Chlorodifluoromethane (75-45-6) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → 1-(2,6-diethylphenyl)-4,4-difluoro-2-azetidinone (145143-43-7) + 1,4-bis(diethylphenyl)-2,5-piperazinedione (145143-47-1)

Conditions	Yield
With sodium hydride 1) THF, hexane, 1 h, 2) THF, 50 deg C; Yield given. Multistep reaction. Yields of byproduct given;

chloromethyl propyl ether (3587-57-3) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → N-butoxymethyl-alpha-chloro-2',6'-diethylacetanilide (67535-25-5)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;

isopropoxymethyl chloride (3587-58-4) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → 2-Chloro-N-(2,6-diethyl-phenyl)-N-isopropoxymethyl-acetamide (67535-24-4)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;

chloromethyl isobutyl ether (34180-11-5) + 2-chloro-2',6'-diethylacetanilide (6967-29-9) → 2-Chloro-N-(2,6-diethyl-phenyl)-N-isobutoxymethyl-acetamide (33717-32-7)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;

2-chloro-2',6'-diethylacetanilide (6967-29-9) + (methoxy-ethoxy)-methyl chloride (85232-18-4) → 2-Chloro-N-(2,6-diethyl-phenyl)-N-(1-methoxy-ethoxymethyl)-acetamide (85232-16-2)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;

2-chloro-2',6'-diethylacetanilide (6967-29-9) + chloromethyl methyl ether (107-30-2) → Alachlor (15972-60-8)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;

2-chloro-2',6'-diethylacetanilide (6967-29-9) + 1-(chloromethoxy)butane (2351-69-1) → N-butoxymethyl-2-chloro-N-(2,6-diethylphenyl)acetamide (23184-66-9)

Conditions	Yield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;

2-chloro-2',6'-diethylacetanilide (6967-29-9) → 2-Hydroxy-N-(2,6-diethylphenyl)acetamide (52559-52-1)

Conditions	Yield
With sodium hydroxide In acetone for 8h; Substitution; Heating;
With aq. NaCO3 In ethanol for 6h; Hydrolysis;