Product Name

  • Name

    Ethyl (R)-(-)-4-cyano-3-hydroxybutyate

  • EINECS 430-220-6
  • CAS No. 141942-85-0
  • Article Data32
  • CAS DataBase
  • Density 1.132 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H11NO3
  • Boiling Point 325.6 °C at 760 mmHg
  • Molecular Weight 157.169
  • Flash Point 150.7 °C
  • Transport Information
  • Appearance yellow liquid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 141942-85-0 (Ethyl (R)-(-)-4-cyano-3-hydroxybutyate)
  • Hazard Symbols IrritantXi
  • Synonyms Butanoicacid, 4-cyano-3-hydroxy-, ethyl ester, (R)-;(3R)-4-Cyano-3-hydroxybutyric acidethyl ester;(R)-Ethyl 4-cyano-3-hydroxybutanoate;Ethyl (R)-4-cyano-3-hydroxybutyrate;
  • PSA 70.32000
  • LogP 0.21418

Synthetic route

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

sodium cyanide
143-33-9

sodium cyanide

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With glucose dehydrogenase; ketoreductase In acetic acid butyl ester; water at 30 - 40℃; for 16h; Product distribution / selectivity; Aqueous phosphate buffer;98%
sodium cyanide
143-33-9

sodium cyanide

(S)-4-bromo-3-hydroxy-butyric acid ethyl ester
32224-01-4, 95310-94-4, 128052-98-2, 95537-36-3

(S)-4-bromo-3-hydroxy-butyric acid ethyl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
at 50℃; for 3h;95%
In N,N-dimethyl-formamide at 20℃;50%
sodium cyanide
773837-37-9

sodium cyanide

ethyl (S)-4-chloro-3-hydroxybutanoate
10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4

ethyl (S)-4-chloro-3-hydroxybutanoate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid; sodium hydroxide In water at 40℃; pH=7.3; Enzymatic reaction;93%
With halohydrindehalogenase from parvibaculum lavamentivorans at 40℃; for 14h; pH=8; Kinetics; Enzymatic reaction;85%
In water; N,N-dimethyl-formamide at 50℃; for 3h;70%
(R)-3-hydroxy-4-cyano-butyric acid
287955-93-5

(R)-3-hydroxy-4-cyano-butyric acid

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid In ethanol90%
cyanoacetoacetic acid ethyl ester
1715-68-0

cyanoacetoacetic acid ethyl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With D-glucose In phosphate buffer at 30℃; for 24h; pH=7;83.1%
sodium cyanide
143-33-9

sodium cyanide

(S)-4-iodo-3-hydroxy-butyric acid ethyl ester
112100-39-7

(S)-4-iodo-3-hydroxy-butyric acid ethyl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
In ethanol; water at 45℃; for 3h;81%
(S)-4-bromo-3-hydroxybutyric acid,ethyl ester
32224-01-4

(S)-4-bromo-3-hydroxybutyric acid,ethyl ester

sodium cyanide
143-33-9

sodium cyanide

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
In water at 25 - 35℃; for 7.33h; pH=8 - 9.5;80%
sodium cyanide
143-33-9

sodium cyanide

ethyl (S)-4-chloro-3-hydroxybutanoate
10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4

ethyl (S)-4-chloro-3-hydroxybutanoate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With acetic acid In water at 105 - 110℃; for 0.02125h;80%
With sodium dihydrogen phosphate monohydrate In formamide at 65℃; for 1.25h;76.4%
In water at 105℃; for 0.0133333h;67.4%
ethanol
64-17-5

ethanol

(R)-3-hydroxy-4-cyano-butyric acid
287955-93-5

(R)-3-hydroxy-4-cyano-butyric acid

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 1h;62%
hydrogenchloride In diethyl ether; ethanol at 20℃; for 30h;
With hydrogenchloride In diethyl ether; ethanol at 20℃; for 30h; Inert atmosphere;
With hydrogenchloride In diethyl ether at 20℃; for 30h; Inert atmosphere;
ethanol
64-17-5

ethanol

(R)-3-hydroxy-4-cyano-butyric acid
287955-93-5

(R)-3-hydroxy-4-cyano-butyric acid

A

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

B

(S)-3-hydroxy-4-cyanobutyric acid ethyl ester
312745-91-8

(S)-3-hydroxy-4-cyanobutyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 0.5h; Title compound not separated from byproducts.;
...Expand
3-hydroxyglutaronitrile
13880-89-2

3-hydroxyglutaronitrile

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitrilase III; phosphate buffer / 22 h / 22 °C / pH 7
2: HCl / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: water / 22 h / 22 °C / pH 7
2: hydrogenchloride / ethanol; diethyl ether / 30 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: water; A190H / aq. phosphate buffer / 21 °C / pH 7 / Enzymatic reaction
2: hydrogenchloride / diethyl ether / 30 h / 20 °C / Inert atmosphere
View Scheme
(R)-4-cyano-3-hydroxybutyric acid calcium salt

(R)-4-cyano-3-hydroxybutyric acid calcium salt

ethanol
64-17-5

ethanol

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid at 0℃; for 1h; Heating / reflux; Neat (no solvent);
(R)-potassium 3-hydroxy-4-cyano-butyrate
635680-93-2

(R)-potassium 3-hydroxy-4-cyano-butyrate

ethanol
64-17-5

ethanol

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With sulfuric acid at 0℃;n/a
diethyl sulfate
64-67-5

diethyl sulfate

(S)-(-)-methyl-(3-hydroxy-4-bromo)-butanoate
88759-56-2

(S)-(-)-methyl-(3-hydroxy-4-bromo)-butanoate

(R)-3-hydroxy-4-cyano-butyric acid
287955-93-5

(R)-3-hydroxy-4-cyano-butyric acid

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With hydrogenchloride; calcium hydroxide; sodium bicarbonate; calcium chloride; triethylamine In water; ethyl acetate
...Expand
(S)-4-bromo-3-hydroxy-butyric acid ethyl ester
32224-01-4, 95310-94-4, 128052-98-2, 95537-36-3

(S)-4-bromo-3-hydroxy-butyric acid ethyl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With NaCN In ethanol; water29.8 g (95%)
sodium cyanide
143-33-9

sodium cyanide

ethyl (S)-4-chloro-3-hydroxybutanoate
10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4

ethyl (S)-4-chloro-3-hydroxybutanoate

A

(E)-ethyl 4-hydroxybut-2-enoate
10080-68-9

(E)-ethyl 4-hydroxybut-2-enoate

B

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
In water at 55℃; for 3h; pH=8.5 - 9; Product distribution / selectivity;
...Expand
hydrogen cyanide
74-90-8

hydrogen cyanide

ethyl (S)-4-chloro-3-hydroxybutanoate
10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4

ethyl (S)-4-chloro-3-hydroxybutanoate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
Stage #1: hydrogen cyanide With halohydrin dehalogenase In water at 40℃; for 0.5h; pH=7;
Stage #2: ethyl (S)-4-chloro-3-hydroxybutanoate In water for 21h; pH=7; Product distribution / selectivity;
sodium cyanide
773837-37-9

sodium cyanide

(S)-4-bromo-3-hydroxy-butyric acid ethyl ester
32224-01-4, 95310-94-4, 128052-98-2, 95537-36-3

(S)-4-bromo-3-hydroxy-butyric acid ethyl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
In ethanol; water
sodium cyanide
773837-37-9

sodium cyanide

ethyl (-)-(2S)-oxirane-2-acetate
112083-63-3

ethyl (-)-(2S)-oxirane-2-acetate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With ammonia; nickel dichloride In aq. phosphate buffer; water at 30℃; pH=8; Kinetics; Enzymatic reaction;
sodium cyanide
773837-37-9

sodium cyanide

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With vector pACYCDuet-RB and vector pET30-halohydrin dehalogenase in Escherichia coli BL21 (DE3) In aq. buffer at 30℃; for 2h; pH=7; Enzymatic reaction; stereoselective reaction;n/a
sodium cyanide
773837-37-9

sodium cyanide

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

A

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

B

(S)-3-hydroxy-4-cyanobutyric acid ethyl ester
312745-91-8

(S)-3-hydroxy-4-cyanobutyric acid ethyl ester

Conditions
ConditionsYield
With vector pCDFDuet-HF and vector pET30-(S)-alcohol dehydrogenase in Escherichia coli BL21(DE3) In aq. buffer at 30℃; for 10h; pH=7; Enzymatic reaction; stereoselective reaction;A n/a
B n/a
With halohydrin dehalogenase; NAD; magnesium chloride; alcohol dehydrogenase In tert-butyl methyl ether at 40℃; under 760.051 Torr; for 10h; pH=8; Solvent; Reagent/catalyst; Concentration; Time; Electrolysis; Sealed tube; Inert atmosphere; Enzymatic reaction;A n/a
B n/a
...Expand
ethyl (S)-4-chloro-3-hydroxybutanoate
10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4

ethyl (S)-4-chloro-3-hydroxybutanoate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
With sodium cyanide; halohydrin dehalogenase In aq. phosphate buffer at 30℃; for 4h; pH=8; Enzymatic reaction;
ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

A

(E)-ethyl 4-hydroxybut-2-enoate
10080-68-9

(E)-ethyl 4-hydroxybut-2-enoate

B

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ketoreductase / acetic acid butyl ester; water / 11 h / pH 7
2: water / 3 h / 55 °C / pH 8.5 - 9
View Scheme
ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ketoreductase / acetic acid butyl ester; water / 11 h / pH 7
2: water / 3 h / 55 °C / pH 8
View Scheme
O-(4-methoxybenzyl)-trichloroacetimidate
89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

ethyl (R)-4-cyano-3-[(4-methoxybenzyl)oxy]butanoate
1031883-60-9

ethyl (R)-4-cyano-3-[(4-methoxybenzyl)oxy]butanoate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane; cyclohexane at 25℃; for 3h;99%
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-ethyl-5-amino-3-hydroxy-5-oxopentanoate
717127-73-6

(R)-ethyl-5-amino-3-hydroxy-5-oxopentanoate

Conditions
ConditionsYield
With Wilkinson's catalyst; 2,2-dimethylpropionaldehyde oxime In toluene at 110℃; for 4h;99%
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

4-hydroxy-δ-valerolactam
1051316-41-6

4-hydroxy-δ-valerolactam

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen In methanol99%
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-4-cyano-3-hydroxybutyric acid hydrazide

(R)-4-cyano-3-hydroxybutyric acid hydrazide

Conditions
ConditionsYield
With hydrazine In ethanol for 2h;98%
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-4-cyano-3-hydroxybutyramide

(R)-4-cyano-3-hydroxybutyramide

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 10h;83%
With ammonium hydroxide In methanol
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

methyl iodide
74-88-4

methyl iodide

(R) 4-cyano-3-methoxyl butyric acid ethyl ester

(R) 4-cyano-3-methoxyl butyric acid ethyl ester

Conditions
ConditionsYield
With silver(l) oxide at 20℃;63.1%
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

1,2-dibromomethane
74-95-3

1,2-dibromomethane

(R)-6,6-dibromo-3-hydroxy-5-oxohexanenitrile

(R)-6,6-dibromo-3-hydroxy-5-oxohexanenitrile

Conditions
ConditionsYield
Stage #1: 1,2-dibromomethane With lithium diisopropyl amide In tetrahydrofuran at -90℃; for 0.0666667h; Inert atmosphere; Flow reactor;
Stage #2: (R)-ethyl 4-cyano-3-hydroxybutyrate In tetrahydrofuran at -90℃; Inert atmosphere; Flow reactor;		22%
t-butyl lithioacetate
150942-98-6

t-butyl lithioacetate

(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate
125988-01-4

tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate

Conditions
ConditionsYield
In tetrahydrofuran; hexane Yield given;
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-5-Amino-pentane-1,3-diol

(R)-5-Amino-pentane-1,3-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-3-hydroxy-4-cyano-butyric acid
287955-93-5

(R)-3-hydroxy-4-cyano-butyric acid

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 2h;
With sodium hydroxide; water for 2h;
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

[3-((R)-4-Cyano-3-hydroxy-butyrylamino)-propyl]-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
669013-16-5

[3-((R)-4-Cyano-3-hydroxy-butyrylamino)-propyl]-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / 2 h / 20 °C
2: 64 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; aq. NaH2PO4 / dimethylformamide; tetrahydrofuran / 16 h / 20 °C / pH 5.7 - 6.0
View Scheme
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

(3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
669013-14-3

(3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. NaOH / 2 h / 20 °C
2: 64 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; aq. NaH2PO4 / dimethylformamide; tetrahydrofuran / 16 h / 20 °C / pH 5.7 - 6.0
3: 63 percent / N,N-diisopropylethylamine / CH2Cl2 / 3 h / 20 °C
View Scheme

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Chemical Properties

Molecular structure of Ethyl (R)-(-)-4-cyano-3-hydroxybutyate (CAS NO.141942-85-0) is:

Product Name: Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
CAS Registry Number: 141942-85-0
IUPAC Name: ethyl (3R)-4-cyano-3-hydroxybutanoate
Molecular Weight: 157.16714 [g/mol]
Molecular Formula: C7H11NO3
XLogP3-AA: -0.5
H-Bond Donor: 1
H-Bond Acceptor: 4 
EINECS: 430-220-6 
Refractive index: n20/D 1.448(lit.) 
Surface Tension: 44.1 dyne/cm
Density: 1.132 g/cm3
Flash Point: 150.7 °C
Enthalpy of Vaporization: 65.8 kJ/mol
Boiling Point: 325.6 °C at 760 mmHg
Vapour Pressure: 1.75E-05 mmHg at 25°C
Product Categories: Pharmaceutical Intermediates; Alcohols, Hydroxy Esters and Derivatives; Chiral Compounds; Intermediatesofatorvastatin; chiral; API intermediates

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Safety Profile

Safty information about Ethyl (R)-(-)-4-cyano-3-hydroxybutyate (CAS NO.141942-85-0) is:
Hazard Codes: IrritantXi
Risk Statements 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 1

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Specification

 Ethyl (R)-(-)-4-cyano-3-hydroxybutyate , its cas register number is 141942-85-0. It also can be called ethyl (3R)-4-cyano-3-hydroxybutanoate . It is a yellow liquid.

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