Product Name

  • Name

    (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide

  • EINECS 1312995-182-4
  • CAS No. 863127-76-8
  • Article Data6
  • CAS DataBase
  • Density 1.197 g/cm3
  • Solubility
  • Melting Point
  • Formula C12H14ClNO2
  • Boiling Point 386.5 °C at 760 mmHg
  • Molecular Weight 239.702
  • Flash Point 187.6 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 863127-76-8 ((E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide)
  • Hazard Symbols
  • Synonyms (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide;(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-2-propenamide;
  • PSA 38.33000
  • LogP 3.21010

Synthetic route

(2E)-3-ethoxyprop-2-enoyl chloride
6191-99-7, 99471-66-6

(2E)-3-ethoxyprop-2-enoyl chloride

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide
863127-76-8

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; for 3h;78.3%
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;73.6%
With pyridine In tetrahydrofuran at 0 - 20℃;73.6%
With pyridine In tetrahydrofuran at 10 - 30℃; for 4h;300 g
3-ethoxyacryloyl chloride
6191-99-7

3-ethoxyacryloyl chloride

2-chloro-6-methylaniline
87-63-8

2-chloro-6-methylaniline

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide
863127-76-8

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 20℃;
With pyridine In tetrahydrofuran at 20℃;
ethyl 3-ethoxyacrylate
1001-26-9

ethyl 3-ethoxyacrylate

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide
863127-76-8

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; water / 2 h / Reflux
2: thionyl chloride / 2 h / Reflux
3: pyridine / tetrahydrofuran / 20 °C
View Scheme
(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide
863127-76-8

(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide

thiourea
17356-08-0

thiourea

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
302964-24-5

2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With iodine(I) bromide; 1-n-butyl-3-methylimidazolim bromide In tetrahydrofuran at 40℃;
Stage #2: thiourea In tetrahydrofuran for 1.5h; Temperature; Concentration; Solvent; Reagent/catalyst;		98.8%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at -10 - 22℃; for 3h;
Stage #2: thiourea In 1,4-dioxane; water at 100℃; for 2h;
Stage #3: With ammonia In 1,4-dioxane; water at 20 - 22℃;		90%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane at -10 - 22℃; for 3h;
Stage #2: thiourea In 1,4-dioxane at 100℃; for 2h;
Stage #3: With ammonium hydroxide In 1,4-dioxane; water at 20 - 22℃;		90%
Stage #1: (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide With N-Bromosuccinimide In 1,4-dioxane; water at 25 - 30℃; for 3h;
Stage #2: thiourea In 1,4-dioxane; water at 25 - 70℃; for 2h;		213 g

(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide Specification

The (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide with the CAS number 863127-76-8 is also called (2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-2-propenamide. The systematic name is 2-propenamide, N-(2-chloro-6-methylphenyl)-3-ethoxy-, (2E)-. Its molecular formula is C12H14ClNO2.

The properties of the chemical are: (1)ACD/LogP: 3.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.04; (4)ACD/LogD (pH 7.4): 3.04; (5)ACD/BCF (pH 5.5): 120.64; (6)ACD/BCF (pH 7.4): 120.63; (7)ACD/KOC (pH 5.5): 1075.3; (8)ACD/KOC (pH 7.4): 1075.23; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 38.33 Å2; (13)Index of Refraction: 1.572; (14)Molar Refractivity: 65.94 cm3; (15)Molar Volume: 200.2 cm3; (16)Polarizability: 26.14×10-24cm3; (17)Surface Tension: 42.3 dyne/cm; (18)Enthalpy of Vaporization: 63.55 kJ/mol; (19)Vapour Pressure: 3.51E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CCO/C=C/C(=O)Nc1c(cccc1Cl)C
(2)InChI: InChI=1/C12H14ClNO2/c1-3-16-8-7-11(15)14-12-9(2)5-4-6-10(12)13/h4-8H,3H2,1-2H3,(H,14,15)/b8-7+
(3)InChIKey: DBYFNZJHXGNAGW-BQYQJAHWBA

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