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Cas Database

Name	3-Hydroxypropionitrile	EINECS	203-704-8
CAS No.	109-78-4	Density	1.04 g/cm³
PSA	44.02000	LogP	-0.10762
Solubility	>=10 g/100 mL at 20 °C in water	Melting Point	-46 °C
Formula	C₃H₅NO	Boiling Point	229.6 °C at 760 mmHg
Molecular Weight	71.0788	Flash Point	92.7 °C
Transport Information	2810	Appearance	Colourless or straw-coloured liquid
Safety	26-36-24/25	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
Synonyms	Hydracrylonitrile(8CI);1-Cyano-2-hydroxyethane;2-Cyanoethanol;2-Cyanoethyl alcohol;2-Hydroxycyanoethane;2-Hydroxyethyl cyanide;3-Hydroxypropanenitrile;Ethylene cyanhydrine;Ethylene cyanohydrin;Glycolcyanohydrin;NSC 2598;b-Cyanoethanol;b-Hydroxyethyl cyanide;b-Hydroxypropionitrile;	Article Data	71

3-Hydroxypropionitrile Synthetic route

: 107-13-1
acrylonitrile

A: 111-97-7
3,3'-thiobis-propanenitrile

B: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With sodium sulfide; benzyltri(n-butyl)ammonium chloride In water for 0.166667h;	A 98% B n/a

: 75-21-8
oxirane

: 74-90-8
hydrogen cyanide

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With aluminum oxide; boron trifluoride diethyl etherate In propylene glycol at -10 - 10℃; for 28h; Reagent/catalyst; Temperature;	97.3%

: 143-33-9
sodium cyanide

: 107-07-3
2-chloro-ethanol

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With PEG400 for 6h; Heating;	93%

: 107-13-1
acrylonitrile

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With sodium hydroxide at 50℃; for 0.2h;	92%
With sodium hydroxide In water at 50℃; for 4h;	65%
With water; copper(II) oxide

: 90087-76-6, 89923-32-0
3-((tetrahydro-2H-pyran-2-yl)oxy)propanenitrile

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With silica-supported NaHSO4 In methanol at 20℃; for 0.25h;	92%
With zinc(II) trifluoromethanesulfonate In methanol at 20℃; for 0.666667h;	81%

: 3-(4-methoxybenzyloxy)propanenitrile

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite at 20℃; for 18h; Green chemistry; chemoselective reaction;	84%

: 151-50-8
potassium cyanide

: 107-07-3
2-chloro-ethanol

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With sodium iodide In ethanol for 5h; Heating;	80%
at 100℃;
With ethanol

: 131379-56-1
3-(1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-yl)propanenitrile

: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With 2,3-dimethyl-1,4-benzoquinone; tetrabutyl ammonium fluoride; oxygen In tetrahydrofuran for 0.833333h; Ambient temperature;	71%

: 107-13-1
acrylonitrile

: 108-95-2
phenol

A: 3055-86-5
3-phenoxypropionitrile

B: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With tetramethyl ammoniumhydroxide In water at 60℃; for 0.5h; Temperature; Reagent/catalyst; Time; Michael Addition; Microwave irradiation;	A 68% B n/a

: 22059-21-8
aminocyclopropane-1-carboxylic acid

A: 74-85-1
ethene

B: 109-78-4
3-Hydroxypropionitrile

Conditions

Conditions	Yield
With lithium hypochlorite In water Ambient temperature;	A 9.8% B 60%
With lithium hypochlorite In water Product distribution; Mechanism; Ambient temperature; other solvent and additives; var. cyclopropanamines;	A 9.8% B 60%

3-Hydroxypropionitrile Chemical Properties

Hydracrylonitrile(109-78-4)'s molecular formula is C₃H₅NO and its formula weight is 71.08.
The density of hydracrylonitrile(109-78-4) is 1.04 and it has a melting point of -46°C. The Boiling point is 228°C. The refractive index is about 1.4246-1.4266. Its flash point is 128°C. The water solubility should be equal to or greater than 10 g/100 mL at 20°C.
Hydracrylonitrile(109-78-4) has the property of being dissolved in water, ethanol, acetone and methyl ethyl ketone(MEK). It is not soluble in benzene, light petroleum, carbon bisulfide and Carbon tetrachloride.
The molecular structure of hydracrylonitrile(109-78-4) :

3-Hydroxypropionitrile Uses

Hydracrylonitrile(109-78-4) is used as a solvent for dissolving cellulose esters and some Inorganic salts. 3-Amino-1-propanol can be produced from hydracrylonitrile(109-78-4) by hydrogenation, which is used to produce synthetic drug( such as cyclophosphamide and inderal).

3-Hydroxypropionitrile Toxicity Data With Reference

1.	skn-rbt 10 mg/24H open	JIHTAB Journal of Industrial Hygiene and Toxicology. 26 (1944),269.
2.	skn-rbt 520 mg open MLD	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 8/18 ,1967.
3.	eye-rbt 500 mg	AJOPAA American Journal of Ophthalmology. 29 (1946),1363.
4.	orl-rat LD50:3200 mg/kg	38MKAJ Pattys Industrial Hygiene and Toxicology. 2C (1982),4875.
5.	orl-mus LD50:1800 mg/kg	AMIHBC AMA Archives of Industrial Hygiene and Occupational Medicine. 8 (1953),371.
6.	ihl-mus LC33:300 mg/m3/2H	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,66.
7.	ipr-mus LD50:500 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
8.	orl-rbt LDLo:900 mg/kg	AMIHBC AMA Archives of Industrial Hygiene and Occupational Medicine. 8 (1953),371.
9.	skn-rbt LD50:5000 mg/kg	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide

3-Hydroxypropionitrile Consensus Reports

Reported in EPA TSCA Inventory. Cyanide compounds are on the Community Right-To-Know List.

3-Hydroxypropionitrile Safety Profile

Poison by inhalation. Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact. A skin and eye irritant. Combustible when exposed to heat or flame. Reacts violently with mineral acids (e.g., chlorosulfonic acid, oleum, sulfuric acid), amines, or inorganic bases (e.g., NaOH). Reacts with water or steam to produce toxic and flammable vapors. To fight fire, use CO₂, dry chemical, alcohol foam. When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of CN⁻. See also NITRILES.

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