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78-97-7

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Basic Information
CAS No.: 78-97-7
Name: Lactonitrile
Article Data: 66
Molecular Structure:
Molecular Structure of 78-97-7 (Lactonitrile)
Formula: C3H5 N O
Molecular Weight: 71.0788
Synonyms: Lactonitrile(6CI,7CI,8CI); (?à)-2-Hydroxypropanenitrile;(?à)-2-Hydroxypropionitrile;2-Hydroxypropanenitrile; 2-Hydroxypropionitrile; Acetaldehyde, cyanohydrin;Acetocyanohydrin; NSC 7764; a-Hydroxypropionitrile
EINECS: 201-163-2
Density: 0.991
Melting Point: -40.15°C
Boiling Point: 90 ºC (17 mmHg)
Flash Point: 77 °C
Appearance: Straw colored liquid.
Hazard Symbols:
Risk Codes: R23/25;R27   
Safety: Poison by ingestion, skin contact, and subcutaneous routes. Moderately toxic by inhalation. In the presence of alkali, it evolves HCN. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of CN− and NOx. See also NITRILES.
Transport Information: UN 3276
PSA: 44.02000
LogP: -0.10922
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Synthetic route
74-90-8

hydrogen cyanide

75-07-0

acetaldehyde

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With triethylamine at 5 - 10℃; Product distribution / selectivity;99%
With triethylamine at 0 - 10℃; pH=2 - 3;99.54%
With sodium acetate; acetic acid; 2-hydroxy-propionitrile
151-50-8

potassium cyanide

75-07-0

acetaldehyde

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium hydrogensulfite In water at 0℃; for 2h;80%
With acetic acid In diethyl ether; water22%
114711-04-5

2-[(tert-butyldimethylsilyl)oxy]propanenitrile

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In dimethyl sulfoxide at 80℃; for 19h; desilylation;80%
7677-24-9

trimethylsilyl cyanide

75-07-0

acetaldehyde

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With ytterbium(III) chloride; 2,6-bis[4′-isopropyloxazolin-2′-yl]pyridine In acetonitrile for 2h; Ambient temperature;61%
With hydrogenchloride
107-13-1

acrylonitrile

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With tetrachloromethane; copper(II) choride dihydrate; chromium(III) acetylacetonate; water at 110℃; for 6h; Sealed tube;46%
With acetic acid; lithium iodide In [D3]acetonitrile at 20℃; for 3h; Irradiation; Inert atmosphere;
74-90-8

hydrogen cyanide

151-50-8

potassium cyanide

75-07-0

acetaldehyde

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
at 25 - 30℃;
...Expand
74-90-8

hydrogen cyanide

75-07-0

acetaldehyde

A

107-13-1

acrylonitrile

B

78-97-7

2-hydroxy-propionitrile

...Expand
74-90-8

hydrogen cyanide

67-66-3

chloroform

75-07-0

acetaldehyde

130-95-0

Quinine

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
at 25℃;
...Expand
143-33-9

sodium cyanide

75-07-0

acetaldehyde

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With ammonium chloride In diethyl ether
With Dowex-H+ In water for 24h; Ambient temperature;
17374-27-5

1,5-dimethylimidazolidine-2,4-dione

A

16752-54-8

methylaminopropionitrile

B

57768-53-3

α-methylaminodipropionitrile

C

carbamate de l' α-N-methylaminopropionitrile

D

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
...Expand
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Chemistry

IUPAC Name: 2-Hydroxypropanenitrile
CAS: 78-97-7
EINECS: 201-163-2
Following is the Molecular Structure of Lactonitrile (78-97-7):

SMILES: N#CC(C)O
Molecular Formula: C3H5NO
Molecular Weight: 71.08
Melting Point:<21℃
Boiling Point: 183.4℃ at 760mmHg
Flash Point: 64.7℃
Molar Volume: 69.3cm3
Density: 1.025g/cm3
Molar Refractivity: 17.35cm3
Surface Tension: 39.6dyne/cm
Polarizability: 6.87 10-24cm3
Enthalpy of Vaporization: 48.84kJ/mol
Vapour Pressure: 0.222mmHg at 25℃
Refractive Index: n20/D 1.404

Uses

Solvent, intermediate in production of Ethyl acetate and Lactic acid .

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 300mg/kg (300mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
mouse LD50 intraperitoneal 15mg/kg (15mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Toxicology and Applied Pharmacology. Vol. 84, Pg. 533, 1986.
rabbit LD50 skin 20uL/kg (0.02mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rabbit LDLo subcutaneous 5200ug/kg (5.2mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
rat LCLo inhalation 125ppm/4H (125ppm)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat LD50 oral 87mg/kg (87mg/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Safety Profile

Hazard Codes: T+ Very toxic, T Toxic. 
Risk Statements: 23/25-27-25-20
R23/25: Toxic by inhalation and if swallowed.
R27: Very Toxic in contact with skin.
R25: Toxic if swallowed.
R20: Harmful by inhalation.
Safety Statements: 13-36/37/39-45-23
S13: Keep away from food, drink and animal feeding stuffs.
S36/27/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
S23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).
RIDADR: UN 3276 6.1/PG 1
WGK: Germany 3
RTECS: OD8225000
HazardClass: 6.1(a)
PackingGroup: II
Poison by ingestion, skin contact, and subcutaneous routes. Moderately toxic by inhalation. In the presence of alkali, it evolves HCN .Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use foam, CO2 , dry chemical.

Specification

 Lactonitrile (78-97-7),which also can be called for 2-Hydroxypropanenitrile ; 2-Hydroxypropannitril ; 2-Hydroxypropannitril ; 2-Hydroxypropionitrile ; Acetaldehyde ; Cyanohydrin ; Acetocyanohydrin ; Ethylidene cyanohydrin ; Lactonitrile ; Laktonitril ; Laktonitril ; Propanenitrile,2-hydroxy- ; Propionitrile,2-hydroxy- ; Alpha-hydroxypropionitrile . Lactonitrile (78-97-7) is a straw colored liquid and it's very soluble in water.When heated to decomposition it emits toxic fumes of CN− and NOx .This chemical should be stored in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.