2-(1-Ethoxyethylidene)propanedinitrile

white to beige crystalline powder and chunks

A mixture of malononitrile (17 g, 257.5 λ7 mmol) and triethylorthoacetate (45.95 g, 283.25 mmol) was heated at 95 Description 1; 2-(l-Ethoxy-ethylidene)-malononitrile (Dl); A mixture of malononitrile (17 g, 257.57 - mΛmol) and triethylorthoacetate (45.95 g, 283.25 mmol) was heated at 95 Triethyl orthoacetate (97 g, 0.6 mol), malononitrile (33 g, 0.5 mol) and glacial acetic acid (1.5 g) were placed in a 1 L flask equipped with a stirrer, thermometer and a VIGREUX column (20 x 1 in. ) on top of which a distillation condenser was placed. The reaction mixture was heated and ethyl alcohol began to distill when the temperature of the reaction mixture was about 85-90 C. After about 40 min. , the temperature of the reaction mixture reached 140 C. Then the reaction was concentrated in a rotary evaporator to remove the low-boiling materials and the residue was crystallized from absolute alcohol to yield the pure product (62.2 g, 91percent) as a light yellow solid [MP 91. 6 C (lit. 90-92 C, MCCALL. M. A. J. ORG CHE7N. 1962, 27, 2433-2439.)].Triethyl orthoacetate (97 g, 0.6 mol), malononitrile (33 g, 0.5 mol) and glacial acetic acid (1.5 g) were placed in a 1 L flask equipped with a stirrer, thermometer and a Vigreux column (20.x.1 in.) on top of which a distillation condenser was placed. The reaction mixture was heated and ethyl alcohol began to distill when the temperature of the reaction mixture was about 85-90° C. After about 40 min., the temperature of the reaction mixture reached 140° C. Then the reaction was concentrated in a rotary evaporator to remove the low-boiling materials and the residue was crystallized from absolute alcohol to yield the pure product (62.2 g, 91percent) as a light yellow solid mp 91.6° C. ; Method 1 Triethyl orthoacetate (1.6 L, 9 mol), malononitrile (500 g, 7.57 mol) and glacial acetic acid (25 ml) were placed in a 5 l RB flask equipped with a stirrer, thermometer and a Vigreux column (20*1 in.) on top of which a distillation condenser was placed. Step 1: 2-(1-ethoxy-ethylidene)-malononitrile A mixture of malononitrile (5.0 g, 76 mmol), (EtO)To a stirred solution of malononitrile (2.64 g, 40.0 mmol) in acetic anhydride (9 mL) was added 1 , 1 , 1 -triethoxyethane (6.48 g, 40.0 mmol). The solution was stirred for 15 h at reflux, cooled, and poured into water. The mixture was extracted with ether, and the organic extract was washed with aqueous NaHC0Step (a): To a stirred solution of malononitrile (2.64 g, 40.0 mmol) in acetic anhydride (9 mL) was added 1, 1, 1-triethoxyethane (6.48 g, 40.0 mmol). The solution was stirred for 15 h at reflux, cooled, and poured into water. The mixture was extracted with ether, and the organic extract was washed with aqueous NaHCO(75 a) (1-ethoxyethylidene)malononitrile; An acetic acid (1 mL) solution of malononitrile (4.41 g, 66.8 mmol) and orthotriethyl acetate (14.7 mL, 80.2 mmol) was stirred at 80°C for one hour. The reaction liquid was cooled to room temperature and generated powder was separated by filtration and the title compound (7.14 g, yield 79percent) was obtained. White powder

Herbicide and growth regulator.

Molecular Weight:136.15
XLogP3:0.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:136.063662883
Monoisotopic Mass:136.063662883
Topological Polar Surface Area:56.8
Heavy Atom Count:10
Complexity:217
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes