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5809-59-6

Basic Information
CAS No.: 5809-59-6
Name: 2-hydroxy-3-butenenitrile
Article Data: 17
Molecular Structure:
Molecular Structure of 5809-59-6 (2-hydroxy-3-butenenitrile)
Formula: C4H5 N O
Molecular Weight: 83.0898
Synonyms: 1-Cyano-1-hydroxy-2-propene;2-Hydroxy-3-butenenitrile; 2-Hydroxy-3-butenylnitrile; 2-Propenal, cyanohydrin;Acrolein cyanohydrin; Vinylglycolonitrile
Density: 1.026g/cm3
Boiling Point: 195.2°Cat760mmHg
Flash Point: 71.9°C
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.
PSA: 44.02000
LogP: 0.58168
Synthetic route
40326-19-0

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

5809-59-6

3-cyano-3-hydroxy-1-propene

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

trimethylsilyl cyanide

107-02-8

acrolein

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℃;
74-90-8

hydrogen cyanide

107-02-8

acrolein

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%
60-29-7

diethyl ether

151-50-8

potassium cyanide

64-19-7

acetic acid

107-02-8

acrolein

5809-59-6

3-cyano-3-hydroxy-1-propene

151-50-8

potassium cyanide

107-02-8

acrolein

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;
15667-63-7

2-acetoxy-3-butenenitrile

5809-59-6

3-cyano-3-hydroxy-1-propene

Conditions
ConditionsYield
With methanol at 20℃; for 144h; Inert atmosphere;65.6 g
5809-59-6

3-cyano-3-hydroxy-1-propene

108-24-7

acetic anhydride

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
74-93-1

methylthiol

5809-59-6

3-cyano-3-hydroxy-1-propene

17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

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

3-cyano-3-hydroxy-1-propene

74-90-8

hydrogen cyanide

Conditions
ConditionsYield
In not given pH=4.6; with H2O vapour;96%
5809-59-6

3-cyano-3-hydroxy-1-propene

75-08-1

ethanethiol

2-hydroxy-4-ethylthiobutyronitrile

Conditions
ConditionsYield
With triethyl borane at 20℃; UV-irradiation;95%
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Chemistry

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:

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.

Consensus Reports

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

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.