Product Name

  • Name

    DIETHYL (1-CYANO-3-METHYLBUTYL)MALONATE

  • EINECS 606-069-9
  • CAS No. 186038-82-4
  • Article Data10
  • CAS DataBase
  • Density 1.044 g/cm3
  • Solubility
  • Melting Point
  • Formula C13H21NO4
  • Boiling Point 355.712 °C at 760 mmHg
  • Molecular Weight 255.314
  • Flash Point 155.412 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 186038-82-4 (DIETHYL (1-CYANO-3-METHYLBUTYL)MALONATE)
  • Hazard Symbols
  • Synonyms Propanedioicacid, (1-cyano-3-methylbutyl)-, diethyl ester (9CI);2-Ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester;Diethyl (1-cyano-3-methylbutyl)malonate;
  • PSA 76.39000
  • LogP 1.91468

Synthetic route

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
871577-68-3

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With ethanol; sodium ethanolate at 80℃; for 20h;
Stage #2: With acetic acid In ethanol at 20℃;		100%
With sodium ethanolate In toluene
With sodium ethanolate In ethanol; toluene at 80℃;
diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

sodium cyanide
143-33-9

sodium cyanide

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
In ethanol at 25 - 35℃; for 2 - 3h;97.97%
potassium cyanide

potassium cyanide

diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
With acetic acid In ethanol; water at 30℃; for 0.5h;87.6%
In ethanol at 25 - 42℃; Product distribution / selectivity;
With water; N6-[[(2-Chlorophenyl)methoxy]carbonyl]-N2-[t-butyloxycarbonyl]-D-lysine In dichloromethane at 20℃; Product distribution / selectivity;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In ethanol at 20℃; for 12h;
sodium cyanide
773837-37-9

sodium cyanide

diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
With water; N-benzylcinchonidinum chloride In toluene at 20℃;
hydrogen cyanide
74-90-8

hydrogen cyanide

diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
In ethanol at 20℃; for 4h; Michael Addition;
isovaleraldehyde
590-86-3

isovaleraldehyde

diethyl malonate
105-53-3

diethyl malonate

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; di-n-propylamine / cyclohexane / 8 h / 75 °C
2: ethanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tetrabutylammomium bromide; di-n-propylamine; acetic acid / hexane / 4 h / Reflux
1.2: 20 °C
2.1: acetic acid / ethanol; water / 0.5 h / 30 °C
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

(R,S)-3-cyano-5-methylhexanoic acid ethyl ester
181289-17-8

(R,S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
With water; sodium chloride In dimethyl sulfoxide at 25 - 145℃; for 10 - 12h;94%
With sodium chloride In water; dimethyl sulfoxide at 140℃; for 9h;87.1%
With lithium chloride In water; dimethyl sulfoxide at 140℃; for 1h; Temperature;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

(3S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid

(3S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid

B

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
871577-68-3

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With water; Lipolase at 30℃; for 24h; pH=7.2; Potassium phosphate buffer;
Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With water; Pseudomonas sp. lipase at 30℃; for 24h; pH=7.2; Potassium phosphate buffer;
Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With water; pig liver esterase at 30℃; for 24h; pH=7.2; Potassium phosphate buffer;
Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

(3S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid potassium salt

(3S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid potassium salt

B

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
871577-68-3

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide; water; Lipolase for 24h; pH=8.0; potassium phosphate buffer;
With potassium hydroxide; water; Lipolase for 20 - 25h; pH=7.0; calcium acetate buffer;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

(S)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid sodium salt

(S)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid sodium salt

B

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
871577-68-3

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide; water; calcium acetate; Lipolase for 20 - 25h; pH=7.0;
With lipase Enzymatic reaction;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

(3R)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid
1155989-27-7

(3R)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid

B

(S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid ethyl ester
1232146-79-0

(S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With water; streptomyces griseus protease at 30℃; for 24h; pH=7.2; Potassium phosphate buffer;
Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With water; streptomyces sp. protease at 30℃; for 24h; pH=7.2; Potassium phosphate buffer;
Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

(+/-)-3-cyano-5-methylhexanoic acid potassium salt

(+/-)-3-cyano-5-methylhexanoic acid potassium salt

Conditions
ConditionsYield
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With ethanol; potassium hydroxide at 75 - 80℃;
Stage #2: With water; potassium hydroxide In ethanol at 20℃; for 1h;
Stage #3: Raney nickel
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

(S)-3-cyano-5-methylhexanoic acid ethyl ester
181289-39-4

(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester With calcium acetate hemihydrate; sodium hydroxide In water for 24h;
Stage #2: at 85℃; for 3h; Inert atmosphere;		n/a
Multi-step reaction with 3 steps
1: calcium acetate hemihydrate; sodium hydroxide / water / 24 h
2: Raney nickel water solution / water / 20 h / 2585.81 Torr
3: hydrogenchloride; acetic acid / water / 80 - 110 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide
2: Raney nickel water solution / water / 20 h / 2585.81 Torr
3: hydrogenchloride; acetic acid / water / 80 - 110 °C
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

C12H17O4(1-)*Na(1+)

C12H17O4(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
871577-68-3

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

B

C12H17O4(1-)*Na(1+)

C12H17O4(1-)*Na(1+)

Conditions
ConditionsYield
With calcium acetate hemihydrate; sodium hydroxide In water for 24h;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

C4H11N*C12H18O4

C4H11N*C12H18O4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: calcium acetate hemihydrate; sodium hydroxide / water / 24 h
2: isopropyl alcohol; tert-butyl methyl ether
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide
2: isopropyl alcohol; tert-butyl methyl ether
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

4-isobutyl-2-oxopyrrolidine-3-carboxylic acid

4-isobutyl-2-oxopyrrolidine-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: calcium acetate hemihydrate; sodium hydroxide / water / 24 h
2: Raney nickel water solution / water / 20 h / 2585.81 Torr
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide
2: Raney nickel water solution / water / 20 h / 2585.81 Torr
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

pregabilin
148553-50-8

pregabilin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: calcium acetate hemihydrate; sodium hydroxide / water / 24 h
1.2: 3 h / 85 °C / Inert atmosphere
2.1: potassium hydroxide / water; Isopropyl acetate / 1 h / 20 °C
2.2: 5 h
View Scheme
Multi-step reaction with 4 steps
1.1: calcium acetate hemihydrate; sodium hydroxide / water / 24 h
2.1: Raney nickel water solution / water / 20 h / 2585.81 Torr
3.1: hydrogenchloride; acetic acid / water / 80 - 110 °C
4.1: potassium hydroxide / water; Isopropyl acetate / 1 h / 20 °C
4.2: 5 h
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide
2.1: Raney nickel water solution / water / 20 h / 2585.81 Torr
3.1: hydrogenchloride; acetic acid / water / 80 - 110 °C
4.1: potassium hydroxide / water; Isopropyl acetate / 1 h / 20 °C
4.2: 5 h
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
871577-68-3

(R)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

B

(S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid ethyl ester
1232146-79-0

(S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid ethyl ester

Conditions
ConditionsYield
In aq. phosphate buffer pH=7.2; Resolution of racemate;
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

racemic 3-cyano-5-methylhexanoic acid
181289-16-7

racemic 3-cyano-5-methylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium chloride / dimethyl sulfoxide; water / 1 h / 140 °C
2: sodium hydroxide; water / 0.5 h / 20 °C / pH 8
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

(R,S)-3-iso-butyl-4-aminobutyric acid
128013-69-4, 130912-52-6, 148553-50-8, 148553-51-9

(R,S)-3-iso-butyl-4-aminobutyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium chloride / dimethyl sulfoxide; water / 1 h / 140 °C
2: sodium hydroxide; water / 0.5 h / 20 °C / pH 8
3: hydrogen / 18 h / 80 °C / 6750.68 Torr
View Scheme
Multi-step reaction with 3 steps
1: sodium chloride / water; dimethyl sulfoxide / 9 h / 140 °C
2: potassium hydroxide; dihydrogen peroxide / water; dimethyl sulfoxide / 2 h / 20 °C / Cooling with ice
3: sodium hydroxide / water / 0 - 10 °C
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

A

pregabilin
148553-50-8

pregabilin

B

(R)-pregabalin

(R)-pregabalin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium chloride / dimethyl sulfoxide; water / 1 h / 140 °C
2: sodium hydroxide; water / 0.5 h / 20 °C / pH 8
3: hydrogen / 18 h / 80 °C / 6750.68 Torr
4: lipase Lipolase 100T / aq. phosphate buffer / 24 h / 30 °C / pH 7.5
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

(R)-pregabalin

(R)-pregabalin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium chloride / water; dimethyl sulfoxide / 9 h / 140 °C
2: potassium hydroxide; dihydrogen peroxide / water; dimethyl sulfoxide / 2 h / 20 °C / Cooling with ice
3: sodium hydroxide / water / 0 - 10 °C
4: (S)-Mandelic acid / isopropyl alcohol / 0.5 h / 60 °C
View Scheme
2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester
186038-82-4

2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester

3-carbamoyl-5-methylhexanoic acid

3-carbamoyl-5-methylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium chloride / water; dimethyl sulfoxide / 9 h / 140 °C
2: potassium hydroxide; dihydrogen peroxide / water; dimethyl sulfoxide / 2 h / 20 °C / Cooling with ice
View Scheme

Diethyl(1-cyano-3-methylbutyl)malonate Specification

The Propanedioic acid,2-(1-cyano-3-methylbutyl)-, 1,3-diethyl ester with CAS registry number of 186038-82-4 is also known as 2-Ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester. The systematic name is Diethyl (1-cyano-3-methylbutyl)propanedioate. In addition, the formula is C13H21NO4 and the molecular weight is 255.31.

Physical properties about Propanedioic acid,2-(1-cyano-3-methylbutyl)-, 1,3-diethyl ester are: (1)ACD/LogP: 2.48; (2)#H bond acceptors: 5; (3)#Freely Rotating Bonds: 9; (4)Polar Surface Area: 76.39Å2; (5)Index of Refraction: 1.449; (6)Molar Refractivity: 65.615 cm3; (7)Molar Volume: 244.6 cm3; (8)Polarizability: 26.012×10-24cm3; (9)Surface Tension: 36.028 dyne/cm; (10)Density: 1.044 g/cm3; (11)Flash Point: 155.412 °C; (12)Enthalpy of Vaporization: 60.089 kJ/mol; (13)Boiling Point: 355.712 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. SMILES: N#CC(CC(C)C)C(C(=O)OCC)C(=O)OCC
2. InChI: InChI=1/C13H21NO4/c1-5-17-12(15)11(13(16)18-6-2)10(8-14)7-9(3)4/h9-11H,5-7H2,1-4H3
3. InChIKey: PZGIWBPMOSUKEV-UHFFFAOYAO
4. Std. InChI: InChI=1S/C13H21NO4/c1-5-17-12(15)11(13(16)18-6-2)10(8-14)7-9(3)4/h9-11H,5-7H2,1-4H3
5. Std. InChIKey: PZGIWBPMOSUKEV-UHFFFAOYSA-N       

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