5809-59-6

Basic information

• Product Name: 2-hydroxy-3-butenenitrile
• Synonyms: 2-hydroxy-3-butenenitrile;1-Cyano-1-hydroxy-2-propene;1-Cyano-2-propen-1-ol;Acrolein cyanohydrin;Vinyl glyconitrile;Vinylglycolonitrile
• CAS NO: 5809-59-6
• Molecular Formula: C₄H₅NO
• Molecular Weight: 83.0886
• EINECS: 227-371-3
• Mol File: 5809-59-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 152.16°C (rough estimate)
• Flash Point: 71.9°C
• Appearance: /
• Density: 1.0989 (rough estimate)
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: 1.4550 (estimate)
• PKA: 10.57±0.20(Predicted)
• CAS DataBase Reference: 2-hydroxy-3-butenenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-3-butenenitrile(5809-59-6)
• EPA Substance Registry System: 2-hydroxy-3-butenenitrile(5809-59-6)

Safety Data

• Hazardous Substances Data: 5809-59-6(Hazardous Substances Data)

Usage

General Description

2-hydroxy-3-butenenitrile, also known as β-hydroxyacrylonitrile, is a chemical compound with the molecular formula C4H5NO. It is a colorless liquid with a distinct odor, and it is commonly used as a precursor in the synthesis of pharmaceuticals and agrochemicals. 2-hydroxy-3-butenenitrile is an important intermediate in the production of organic compounds, and it is also used in the manufacturing of plastics, adhesives, and various other industrial products. However, 2-hydroxy-3-butenenitrile can be hazardous if not handled properly, as it is toxic if ingested or inhaled, and it can cause skin and eye irritation on contact. Therefore, it is important to follow proper safety precautions when working with this chemical.

InChI:InChI=1/C4H5NO/c1-2-4(6)3-5/h2,4,6H,1H2

Synthetic route

2-<(trimethylsilyl)oxy>-3-butenenitrile (40326-19-0) → 3-cyano-3-hydroxy-1-propene (5809-59-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water for 4h; Heating;	90%

trimethylsilyl cyanide (7677-24-9) + acrolein (107-02-8) → 3-cyano-3-hydroxy-1-propene (5809-59-6)

Conditions	Yield
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) + acrolein (107-02-8) → 3-cyano-3-hydroxy-1-propene (5809-59-6)

Conditions	Yield
With triethylamine In dichloromethane 1.) 1h 0 deg C; 2.) 30 min r.t.;	72%

diethyl ether (60-29-7) + potassium cyanide (151-50-8) + acetic acid (64-19-7) + acrolein (107-02-8) → 3-cyano-3-hydroxy-1-propene (5809-59-6)

potassium cyanide (151-50-8) + acrolein (107-02-8) → 3-cyano-3-hydroxy-1-propene (5809-59-6)

Conditions	Yield
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) → 3-cyano-3-hydroxy-1-propene (5809-59-6)

Conditions	Yield
With methanol at 20℃; for 144h; Inert atmosphere;	65.6 g

3-cyano-3-hydroxy-1-propene (5809-59-6) + acetic anhydride (108-24-7) → 2-acetoxy-3-butenenitrile (15667-63-7)

Conditions	Yield
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) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → 2-hydroxy-4-(methylthio)butyronitrile (17773-41-0)

Conditions	Yield
With triethyl borane at -10 - 20℃; for 0.0833333h; UV-irradiation;	96%

3-cyano-3-hydroxy-1-propene (5809-59-6) + water (7732-18-5) → hydrogen cyanide (74-90-8)

Conditions	Yield
In not given pH=4.6; with H2O vapour;	96%

3-cyano-3-hydroxy-1-propene (5809-59-6) + ethanethiol (75-08-1) → 2-hydroxy-4-ethylthiobutyronitrile

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

3-cyano-3-hydroxy-1-propene (5809-59-6) + ethyl vinyl ether (109-92-2) → (+/-)-2-(1-ethoxyethoxy)-but-3-enenitrile (72252-03-0)

Conditions	Yield
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) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione (13253-44-6) + 2-[(aminocarbonyl)amino]-4-(methylthio)butanoamide (55064-40-9)

Conditions	Yield
With ammonium carbonate In methanol at 80℃; for 1.5h;	A 85% B 12%

3-cyano-3-hydroxy-1-propene (5809-59-6) + C,N-diphenylnitrone (201024-81-9) → 6-cyano-6-hydroxy-2,3-diphenylisoxazolidine

Conditions	Yield
In benzene for 96h; Heating;	62%

3-cyano-3-hydroxy-1-propene (5809-59-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-chloro-but-3-enenitrile (24253-31-4)

Conditions	Yield
With oxalyl dichloride In acetonitrile for 3h; Ambient temperature;	53%

3-cyano-3-hydroxy-1-propene (5809-59-6) + C-phenyl-N-methylnitrone (3376-23-6, 7372-59-0, 59862-60-1) → 6-cyano-6-hydroxy-2N-methyl-3-phenylisoxazolidine

Conditions	Yield
In benzene for 96h; Heating;	53%

ethanol (64-17-5) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → DL-2-hydroxy-3-butenoic acid ethyl ester (91890-87-8)

Conditions	Yield
With hydrogenchloride

3-cyano-3-hydroxy-1-propene (5809-59-6) → 2-Oxobutyric acid (600-18-0)

Conditions	Yield
With hydrogenchloride Hydrolysis;

3-cyano-3-hydroxy-1-propene (5809-59-6) → 2-oxo-butyronitrile (4390-78-7)

Conditions	Yield
With diethyl ether; phosphorus tribromide

3-cyano-3-hydroxy-1-propene (5809-59-6) → 2-chloro-but-3-enenitrile (24253-31-4)

Conditions	Yield
With pyridine; thionyl chloride; diethyl ether

3-cyano-3-hydroxy-1-propene (5809-59-6) → 2,3-dichlorobutanenitrile (34362-22-6)

Conditions	Yield
With thionyl chloride

3-cyano-3-hydroxy-1-propene (5809-59-6) → 2-hydroxy-but-3-enoic acid amide (210468-74-9)

Conditions	Yield
With hydrogenchloride
With nitrile hydratase from Nitriliruptor alkaliphilus; water Enzymatic reaction;

3-cyano-3-hydroxy-1-propene (5809-59-6) → vinyl glycolic acid (600-17-9)

Conditions	Yield
With hydrogenchloride
Isolierung ueber das Zinksalz;
Isolierung ueber O-Acetyl-vinylglykolsaeue-aethylester;

3-cyano-3-hydroxy-1-propene (5809-59-6) → DL-2-hydroxy-3-butenoic acid ethyl ester (91890-87-8)

3-cyano-3-hydroxy-1-propene (5809-59-6) → 2,3,4-triacetoxy-butyronitrile (40732-35-2, 49560-16-9, 49560-17-0, 75044-64-3)

Conditions	Yield
With dihydrogen peroxide; tungsten(VI) oxide beim Erhitzen des Reaktionsprodukts mit Acetanhydrid;

3-cyano-3-hydroxy-1-propene (5809-59-6) + allyl alcohol (107-18-6) → allyl 2-hydroxybut-3-enoate (98272-42-5)

Conditions	Yield
With hydrogenchloride; water

2,3-Dichloroprop-1-ene (78-88-6) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → 5-Chlor-1,5-hexadien-3-oncyanhydrin (58208-15-4)

Conditions	Yield
Multistep reaction;

N-acetylcystein (616-91-1) + 3-cyano-3-hydroxy-1-propene (5809-59-6) + sodium cyanide (143-33-9) → L-cystathionine (56-88-2) + (2R,2'R)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid (2998-83-6)

Conditions	Yield
(i), (ii) /BRN= 3587243/, NH4Cl, aq. NH3, (iii) aq. HCl; Multistep reaction;

methylthiol (74-93-1) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → DL-methionine (59-51-8)

Conditions	Yield
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) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → (+/-)-2-methoxymethoxybut-3-enenitrile (80680-90-6)

Conditions	Yield
With phosphorus pentoxide In dichloromethane at 5℃; for 18h;

pyridine (110-86-1) + thionyl chloride (7719-09-7) + diethyl ether (60-29-7) + 3-cyano-3-hydroxy-1-propene (5809-59-6) → 2-chloro-but-3-enenitrile (24253-31-4)

Upstream product

• 60-29-7 diethyl ether 
• 151-50-8 potassium cyanide 
• 64-19-7 acetic acid 
• 107-02-8 acrolein 
• 74-90-8 hydrogen cyanide 
• 15667-63-7 2-acetoxy-3-butenenitrile 
• 40326-19-0 2-<(trimethylsilyl)oxy>-3-butenenitrile 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 98272-42-5 allyl 2-hydroxybut-3-enoate 
• 56-88-2 L-cystathionine 
• 2998-83-6 (2R,2'R)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid 
• 13269-47-1 4-amino-3-hydroxybut-1-ene 
• 7659-46-3 4-chloro-trans-crotononitrile 
• 802294-64-0 propionic acid 
• 600-18-0 2-Oxobutyric acid 
• 600-17-9 vinyl glycolic acid 
• 72252-03-0 (+/-)-2-(1-ethoxyethoxy)-but-3-enenitrile 
• 15667-63-7 2-acetoxy-3-butenenitrile 
• 74-90-8 hydrogen cyanide 
• 17773-41-0 2-hydroxy-4-(methylthio)butyronitrile 
• 59-51-8 DL-methionine 
• 13253-44-6 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione 

Relevant articles and documents

Preparation method of 1-cyano-2-propenyl acetate

The invention relates to a preparation method of 1-cyano-2-allyl acetate. The method comprises the following steps: (1) reacting hydrocyanic acid with acrolein in the presence of a first catalyst to obtain a reaction solution containing acrolein cyanohydrin; and (2) reacting the obtained reaction solution containing acrolein cyanohydrin with an esterifying agent in the presence of a second catalyst to obtain a reaction solution containing 1-cyano-2-propenyl acetate. The first catalyst and the second catalyst are the same or different and are respectively and independently N,N-dimethylaminopyridine carboxylate. According to the preparation method provided by the invention, the efficient catalyst N,N-dimethylaminopyridine carboxylate is used as a catalyst shared by two steps of reactions, and the two steps of main reactions can be efficiently catalyzed, so that the two steps of main reactions can be carried out according to an approximate stoichiometric ratio; the yield of the product 1-cyano-2-propenyl acetate can reach 99% or above, and the purity can reach 99.5% or above; and the investment is saved, and the product competitiveness is improved.

Preparation method of 2-hydroxyl-3-butene-1-amine

The invention discloses a preparation method of 2-hydroxyl-3-butene-1-amine. The preparation method comprises the following specific steps: (1) taking acrolein as a start raw material to react with trimethylsilyl cyanide at room temperature in the presence of lithium perchlorate trihydrate to obtain 2-hydroxyl-3-butene-1-nitrile; (2) with diethyl ether or tetrahydrofuran as a solvent, reducing the 2-hydroxyl-3-butene-1-nitrile with lithium aluminum hydride to obtain a crude product of 2-hydroxyl-3-butene-1-amine; (3) making the crude product of 2-hydroxyl-3-butene-1-amine react with hydrochloric acid to obtain 2-hydroxyl-3-butene-1-amine hydrochloride; and (4) making the 2-hydroxyl-3-butene-1-amine hydrochloride react with alkali to finally obtain the 2-hydroxyl-3-butene-1-amine. According to the method disclosed by the invention, without a trimethylsilyl protection group removal process, the operation of reduced pressure distillation is avoided, the reaction path is shortened, and the operation is simple.

A single-step, mild, neutral, catalyst-free method for cyanohydrin synthesis

A wide variety of carbonyl compounds can be transformed to their corresponding cyanohydrins in a single step using a dimethyl sulfoxide (DMSO)-water system in excellent yields (75-94%). The major advantages of this system are that the reaction conditions are mild and neutral; the reaction proceeds without catalyst and gives the corresponding cyanohydrins in short time (15-120 min).