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2-Chloro-N-(2,6-diethylphenyl)acetamide

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Name

2-Chloro-N-(2,6-diethylphenyl)acetamide

EINECS 214-460-7
CAS No. 6967-29-9 Density 1.131g/cm3
PSA 29.10000 LogP 3.06170
Solubility insoluble in water at normal temperature Melting Point 128-130 °C
Formula C12H16ClNO Boiling Point 369.2 °C at 760mmHg
Molecular Weight 225.718 Flash Point 177.1 °C
Transport Information N/A Appearance White crystal
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 6967-29-9 (N-CHLOROACETYL-2,6-DIETHYLANILINE) Hazard Symbols IrritantXi
Synonyms

Acetanilide,2-chloro-2',6'-diethyl- (7CI,8CI);2-Chloro-2',6'-diethylacetanilide;2-Chloro-N-(2,6-diethylphenyl)acetamide;2',6'-Diethyl-2-chloroacetanilide;2',6'-Diethylchloroacetanilide;N-(2,6-Diethylphenyl)chloroacetamide;NSC68291;w-Chloro-2',6'-diethylacetanilide;

Article Data 17

2-Chloro-N-(2,6-diethylphenyl)acetamide Synthetic route

579-66-8

2,6-diethylaniline

79-04-9

chloroacetyl chloride

6967-29-9

2-chloro-2',6'-diethylacetanilide

Conditions
ConditionsYield
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;
593-71-5

Chloroiodomethane

20458-99-5

2,6-diethylphenylisocyanate

6967-29-9

2-chloro-2',6'-diethylacetanilide

Conditions
ConditionsYield
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%
15972-60-8

Alachlor

6967-29-9

2-chloro-2',6'-diethylacetanilide

Conditions
ConditionsYield
With hydrogenchloride In acetone for 4h; Hydrolysis; Heating;
579-66-8

2,6-diethylaniline

79-04-9

chloroacetyl chloride

6967-29-9

2-chloro-2',6'-diethylacetanilide

Conditions
ConditionsYield
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;
593-71-5

Chloroiodomethane

20458-99-5

2,6-diethylphenylisocyanate

6967-29-9

2-chloro-2',6'-diethylacetanilide

Conditions
ConditionsYield
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%
15972-60-8

Alachlor

6967-29-9

2-chloro-2',6'-diethylacetanilide

Conditions
ConditionsYield
With hydrogenchloride In acetone for 4h; Hydrolysis; Heating;
6967-29-9

2-chloro-2',6'-diethylacetanilide

1074-82-4

potassium phtalimide

70752-53-3

2-amino-2',6'-diethylacetanilide

Conditions
ConditionsYield
In N-methyl-acetamide92%
69602-59-1

1-ethoxy-2-chloromethoxyethane

6967-29-9

2-chloro-2',6'-diethylacetanilide

85211-82-1

2-Chloro-N-(2,6-diethyl-phenyl)-N-(2-ethoxy-ethoxymethyl)-acetamide

Conditions
ConditionsYield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h;90%
20052-60-2

7-Hydroxy-2,2,5-trimethyl-4-chromanone

6967-29-9

2-chloro-2',6'-diethylacetanilide

133035-38-8

N-(2,6-Diethyl-phenyl)-2-(2,2,5-trimethyl-4-oxo-chroman-7-yloxy)-acetamide

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone for 6h; Heating;86.4%
74094-45-4

2,3-dihydro-7-hydroxy-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one

6967-29-9

2-chloro-2',6'-diethylacetanilide

133035-55-9

N-(2,6-Diethyl-phenyl)-2-(6-methoxy-2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide

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

2-Chloro-N-(2,6-diethylphenyl)acetamide Specification

The IUPAC name of this chemical is 2-chloro-N-(2,6-diethylphenyl)acetamide. With the CAS registry number 6967-29-9, it is also named as Acetamide, 2-chloro-N-(2,6-diethylphenyl)-. The product's categories are herbicide intermediates; pesticide intermediates; amide herbicides. The pure product is white crystal which is insoluble in water at normal temperature, slightly soluble in ethanol, acetone and other organic solvents. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.61; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.61; (4)ACD/LogD (pH 7.4): 3.61; (5)ACD/BCF (pH 5.5): 327.33; (6)ACD/BCF (pH 7.4): 327.36; (7)ACD/KOC (pH 5.5): 2196.93; (8)ACD/KOC (pH 7.4): 2197.15; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.559; (13)Molar Refractivity: 64.47 cm3; (14)Molar Volume: 199.5 cm3; (15)Polarizability: 25.55×10-24 cm3; (16)Surface Tension: 40.2 dyne/cm; (17)Enthalpy of Vaporization: 61.6 kJ/mol; (18)Vapour Pressure: 1.2E-05 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Tautomer Count: 2; (21)Exact Mass: 225.092042; (22)MonoIsotopic Mass: 225.092042; (23)Topological Polar Surface Area: 29.1; (24)Heavy Atom Count: 15; (25)Complexity: 196.

Preparation of 2-Chloro-N-(2,6-diethylphenyl)acetamide: Adding xylene and chloroacetic acid in the reactor, and then tranferring it to another reactor after heating a certain time. Adding 2,6-diethyl aniline, dropping phosphorus trichloride under stirring, adding water slowly after rising temperature a certain time, standing to laminate for separate. Xylene liquid move to crystallization reactor to split. Finally, we can get the product by filtering.

Uses of 2-Chloro-N-(2,6-diethylphenyl)acetamide: It is used as intermediate of herbicides alachlor, butachlor and pretilachlor. And it reacts with 7-hydroxy-2,2-dimethyl-chroman-4-one to get N-(2,6-diethyl-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide. This reaction needs reagent K2CO3 and NaI and solvent acetone by heating. The reaction time is 6hours. The yield is 76.8%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. 

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(Nc1c(cccc1CC)CC)CCl
2. 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)

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