Product Name

  • Name

    2-hydroxy-3-butenenitrile

  • EINECS
  • CAS No. 5809-59-6
  • Article Data17
  • CAS DataBase
  • Density 1.026g/cm3
  • Solubility
  • Melting Point
  • Formula C4H5 N O
  • Boiling Point 195.2°Cat760mmHg
  • Molecular Weight 83.0898
  • Flash Point 71.9°C
  • Transport Information
  • Appearance
  • Safety A poison by ingestion, skin contact, and inhalation. A skin and severe eye irritant. May polymerize explosively when exposed to light and air above 25°C. A storage hazard. When heated to decomposition it emits toxic fumes of NOx and CN−. See also NITRILES.
  • Risk Codes
  • Molecular Structure Molecular Structure of 5809-59-6 (2-hydroxy-3-butenenitrile)
  • Hazard Symbols
  • Synonyms 1-Cyano-1-hydroxy-2-propene;2-Hydroxy-3-butenenitrile; 2-Hydroxy-3-butenylnitrile; 2-Propenal, cyanohydrin;Acrolein cyanohydrin; Vinylglycolonitrile
  • PSA 44.02000
  • LogP 0.58168

Synthetic route

2-<(trimethylsilyl)oxy>-3-butenenitrile
40326-19-0

2-<(trimethylsilyl)oxy>-3-butenenitrile

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water for 4h; Heating;90%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

acrolein
107-02-8

acrolein

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 0 - 10℃; for 0.5h;78%
With indium(III) trifluoride; water Ambient temperature;75%
Stage #1: trimethylsilyl cyanide; acrolein With zinc(II) iodide at 20℃; for 16h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1h;		22%
Stage #1: trimethylsilyl cyanide; acrolein With zinc(II) iodide Addition;
Stage #2: With hydrogenchloride Substitution;
With lithium perchlorate trihydrate at 20℃;
hydrogen cyanide
74-90-8

hydrogen cyanide

acrolein
107-02-8

acrolein

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

Conditions
ConditionsYield
With triethylamine In dichloromethane 1.) 1h 0 deg C; 2.) 30 min r.t.;72%
diethyl ether
60-29-7

diethyl ether

potassium cyanide
151-50-8

potassium cyanide

acetic acid
64-19-7

acetic acid

acrolein
107-02-8

acrolein

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

...Expand
potassium cyanide
151-50-8

potassium cyanide

acrolein
107-02-8

acrolein

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

Conditions
ConditionsYield
With diethyl ether; acetic acid wird mit wenig Wasser versetzt, die aetherische Loesung abgehoben und destilliert;
With acetic acid In diethyl ether at 15℃; for 1.5h;
With acetic acid In diethyl ether
With acetic acid In diethyl ether Addition;
2-acetoxy-3-butenenitrile
15667-63-7

2-acetoxy-3-butenenitrile

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

Conditions
ConditionsYield
With methanol at 20℃; for 144h; Inert atmosphere;65.6 g
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

acetic anhydride
108-24-7

acetic anhydride

2-acetoxy-3-butenenitrile
15667-63-7

2-acetoxy-3-butenenitrile

Conditions
ConditionsYield
With sulfuric acid; Acetate de N,N-dimethylamino-4 pyridinium at 40 - 45℃; under 7.50075 Torr; for 1.5h; Pressure; Reagent/catalyst; Temperature;99.9%
at 30℃; for 0.5h; Temperature;99.6%
With sodium acetate
methylthiol
74-93-1

methylthiol

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2-hydroxy-4-(methylthio)butyronitrile
17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

Conditions
ConditionsYield
With triethyl borane at -10 - 20℃; for 0.0833333h; UV-irradiation;96%
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

water
7732-18-5

water

hydrogen cyanide
74-90-8

hydrogen cyanide

Conditions
ConditionsYield
In not given pH=4.6; with H2O vapour;96%
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

ethanethiol
75-08-1

ethanethiol

2-hydroxy-4-ethylthiobutyronitrile

2-hydroxy-4-ethylthiobutyronitrile

Conditions
ConditionsYield
With triethyl borane at 20℃; UV-irradiation;95%
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

ethyl vinyl ether
109-92-2

ethyl vinyl ether

(+/-)-2-(1-ethoxyethoxy)-but-3-enenitrile
72252-03-0

(+/-)-2-(1-ethoxyethoxy)-but-3-enenitrile

Conditions
ConditionsYield
trifluoroacetic acid for 0.0833333h; Ambient temperature;89%
With toluene-4-sulfonic acid In diethyl ether at 5℃; for 0.5h; Yield given;
methylthiol
74-93-1

methylthiol

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

A

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione
13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

B

2-[(aminocarbonyl)amino]-4-(methylthio)butanoamide
55064-40-9

2-[(aminocarbonyl)amino]-4-(methylthio)butanoamide

Conditions
ConditionsYield
With ammonium carbonate In methanol at 80℃; for 1.5h;A 85%
B 12%
...Expand
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

C,N-diphenylnitrone
201024-81-9

C,N-diphenylnitrone

6-cyano-6-hydroxy-2,3-diphenylisoxazolidine

6-cyano-6-hydroxy-2,3-diphenylisoxazolidine

Conditions
ConditionsYield
In benzene for 96h; Heating;62%
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-chloro-but-3-enenitrile
24253-31-4

2-chloro-but-3-enenitrile

Conditions
ConditionsYield
With oxalyl dichloride In acetonitrile for 3h; Ambient temperature;53%
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

C-phenyl-N-methylnitrone
3376-23-6, 7372-59-0, 59862-60-1

C-phenyl-N-methylnitrone

6-cyano-6-hydroxy-2N-methyl-3-phenylisoxazolidine

6-cyano-6-hydroxy-2N-methyl-3-phenylisoxazolidine

Conditions
ConditionsYield
In benzene for 96h; Heating;53%
ethanol
64-17-5

ethanol

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

DL-2-hydroxy-3-butenoic acid ethyl ester
91890-87-8

DL-2-hydroxy-3-butenoic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2-Oxobutyric acid
600-18-0

2-Oxobutyric acid

Conditions
ConditionsYield
With hydrogenchloride Hydrolysis;
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2-oxo-butyronitrile
4390-78-7

2-oxo-butyronitrile

Conditions
ConditionsYield
With diethyl ether; phosphorus tribromide
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2-chloro-but-3-enenitrile
24253-31-4

2-chloro-but-3-enenitrile

Conditions
ConditionsYield
With pyridine; thionyl chloride; diethyl ether
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2,3-dichlorobutanenitrile
34362-22-6

2,3-dichlorobutanenitrile

Conditions
ConditionsYield
With thionyl chloride
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2-hydroxy-but-3-enoic acid amide
210468-74-9

2-hydroxy-but-3-enoic acid amide

Conditions
ConditionsYield
With hydrogenchloride
With nitrile hydratase from Nitriliruptor alkaliphilus; water Enzymatic reaction;
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

vinyl glycolic acid
600-17-9

vinyl glycolic acid

Conditions
ConditionsYield
With hydrogenchloride
Isolierung ueber das Zinksalz;
Isolierung ueber O-Acetyl-vinylglykolsaeue-aethylester;
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

DL-2-hydroxy-3-butenoic acid ethyl ester
91890-87-8

DL-2-hydroxy-3-butenoic acid ethyl ester

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2,3,4-triacetoxy-butyronitrile
40732-35-2, 49560-16-9, 49560-17-0, 75044-64-3

2,3,4-triacetoxy-butyronitrile

Conditions
ConditionsYield
With dihydrogen peroxide; tungsten(VI) oxide beim Erhitzen des Reaktionsprodukts mit Acetanhydrid;
3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

allyl alcohol
107-18-6

allyl alcohol

allyl 2-hydroxybut-3-enoate
98272-42-5

allyl 2-hydroxybut-3-enoate

Conditions
ConditionsYield
With hydrogenchloride; water
2,3-Dichloroprop-1-ene
78-88-6

2,3-Dichloroprop-1-ene

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

5-Chlor-1,5-hexadien-3-oncyanhydrin
58208-15-4

5-Chlor-1,5-hexadien-3-oncyanhydrin

Conditions
ConditionsYield
Multistep reaction;
N-acetylcystein
616-91-1

N-acetylcystein

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

sodium cyanide
143-33-9

sodium cyanide

A

L-cystathionine
56-88-2

L-cystathionine

B

(2R,2'R)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid
2998-83-6

(2R,2'R)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid

Conditions
ConditionsYield
(i), (ii) /BRN= 3587243/, NH4Cl, aq. NH3, (iii) aq. HCl; Multistep reaction;
...Expand
methylthiol
74-93-1

methylthiol

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

DL-methionine
59-51-8

DL-methionine

Conditions
ConditionsYield
With ammonium carbonate; sodium hydroxide 1.) methanol, 80 deg C, 1.5 h; 2.) water, 160 deg C, 1.5 h; Multistep reaction;
Dimethoxymethane
109-87-5

Dimethoxymethane

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

(+/-)-2-methoxymethoxybut-3-enenitrile
80680-90-6

(+/-)-2-methoxymethoxybut-3-enenitrile

Conditions
ConditionsYield
With phosphorus pentoxide In dichloromethane at 5℃; for 18h;
pyridine
110-86-1

pyridine

thionyl chloride
7719-09-7

thionyl chloride

diethyl ether
60-29-7

diethyl ether

3-cyano-3-hydroxy-1-propene
5809-59-6

3-cyano-3-hydroxy-1-propene

2-chloro-but-3-enenitrile
24253-31-4

2-chloro-but-3-enenitrile

...Expand

2-Hydroxy-3-Butenenitrile Chemical Properties

Chemistry informtion about 2-Hydroxy-3-Butenenitrile (CAS NO.5809-59-6) is:
IUPAC Name: 2-Hydroxybut-3-Enenitrile
Synonyms: 2-Hydroxy-3-Butenenitrile ; 1-Cyano-1-Hydroxy-2-Propene ; 1-Cyano-2-Propen-1-Ol ; Acrolein Cyanohydrin ; Vinyl Glyconitrile ; Vinylglycolonitrile
MF: C4H5NO
MW: 83.0886
EINECS: 227-371-3 
Density: 1.026 g/cm3
Flash Point: 71.9 °C
Boiling Point: 195.2 °C at 760 mmHg
Vapour Pressure: 0.11 mmHg at 25°C 
Enthalpy of Vaporization: 50.2 kJ/mol
Following is the molecular structure of 2-Hydroxy-3-Butenenitrile (CAS NO.5809-59-6) is:

2-Hydroxy-3-Butenenitrile Toxicity Data With Reference

1.    

skn-rbt 10 mg/24H open

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
2.    

eye-rbt 50 µg open SEV

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
3.    

orl-rat LD50:65 mg/kg

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
4.    

ihl-rat LC50:16 ppm/4H

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
5.    

skn-rbt LD50:7500 µg/kg

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.

2-Hydroxy-3-Butenenitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List.

2-Hydroxy-3-Butenenitrile Safety Profile

A poison by ingestion, skin contact, and inhalation. A skin and severe eye irritant. May polymerize explosively when exposed to light and air above 25°C. A storage hazard. When heated to decomposition it emits toxic fumes of NOx and CN−. See also NITRILES.

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