5809-59-6

Usage

Uses

Used in Pharmaceutical Industry:
2-hydroxy-3-butenenitrile is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medicines due to its reactive functional groups.
Used in Agrochemical Industry:
In the agrochemical sector, 2-hydroxy-3-butenenitrile serves as a precursor in the production of agrochemicals, playing a crucial role in the synthesis of compounds that protect crops and enhance agricultural productivity.
Used in Plastics Manufacturing:
2-hydroxy-3-butenenitrile is utilized as a component in the manufacturing of plastics, where its properties contribute to the formation of specific types of polymers with desired characteristics for various applications.
Used in Adhesives Production:
2-hydroxy-3-butenenitrile is also used as a precursor in the production of adhesives, where its chemical reactivity helps in creating strong bonds between different materials.
Safety Precautions:
Given its toxic nature when ingested or inhaled, and its potential to cause skin and eye irritation, 2-hydroxy-3-butenenitrile requires careful handling and adherence to proper safety measures to prevent health hazards and environmental contamination.

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 
• 40326-19-0 2-<(trimethylsilyl)oxy>-3-butenenitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 15667-63-7 2-acetoxy-3-butenenitrile 

Downstream Products

• 600-18-0 2-Oxobutyric acid 
• 15667-63-7 2-acetoxy-3-butenenitrile 
• 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 
• 13253-44-6 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione 
• 55064-40-9 2-[(aminocarbonyl)amino]-4-(methylthio)butanoamide 
• 59-51-8 DL-methionine 
• 72252-03-0 (+/-)-2-(1-ethoxyethoxy)-but-3-enenitrile 
• 600-17-9 vinyl glycolic acid 
• 802294-64-0 propionic acid 
• 17773-41-0 2-hydroxy-4-(methylthio)butyronitrile 
• 7659-46-3 4-chloro-trans-crotononitrile 
• 74-90-8 hydrogen cyanide 

Relevant academic research and scientific papers

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.

Method for preparing acrolein cyanohydrins

The present invention relates to an improved method for preparing acrolein cyanohydrins from hydrocyanic acid and the corresponding acroleins. The method is characterized in that the acrolein cyanohydrins obtained have a very low hydrocyanic acid content or are free of hydrocyanic acid and are therefore particularly well suited as intermediates for the synthesis of glufosinates.

PROCESS FOR PREPARING PHOSPHORUS-CONTAINING CYANOHYDRINS

The present invention relates primarily to a process for preparing certain phosphorus-containing cyanohydrins of the formula (I), and also to certain phosphorus-containing cyanohydrins per se and to their use for the preparation of glufosinate and/or glufosinate salts. The present invention further relates to certain mixtures particularly suitable for preparing the phosphorus-containing cyanohydrins of the formula (I).

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).

Rhenium-catalyzed 1,3-isomerization of allylic alcohols: Scope and chirality transfer

(Chemical Equation Presented) The scope of the triphenylsilyl perrhennate (O3ReOSiPh3, 1) catalyzed 1,3-isomerization of allylic alcohols has been thoroughly explored. It was found to be effective for a wide variety of secondary and tertiary allylic alcohol substrates bearing aryl, alkyl, and cyano substituents. Two general reaction types were found which gave high levels of product selectivity: those driven by formation of an extended conjugated system and those driven by selective silylation of a particular isomer. The efficiency of chirality transfer with various substrates was investigated, and conditions were found in which secondary and tertiary allylic alcohols could be formed with high levels of enantioselectivity. Consideration of selectivity trends with respect to the nature of the substituents around the allylic system revealed that this is a reliable and predictable method for allylic alcohol synthesis.

Insecticidal activity of cyanohydrin and monoterpenoid compounds

The insecticidal activities of several cyanohydrins, cyanohydrin esters and monoterpenoid esters (including three monoterpenoid esters of a cyanohydrin) were evaluated. Topical toxicity to Musca domestica L. adults was examined, and testing of many compounds at 100 μg/fly resulted in 100% mortality. Topical LD50 values of four compounds for M. domestica were calculated. Testing of many of the reported compounds to brine shrimp (Artemia franciscana Kellog) resulted in 100% mortality at 10 ppm, and two compounds caused 100% mortality at 1 ppm. Aquatic LC50 for values were calculated for five compunds for larvae of the yellow fever mosquito (Aedes aegypti (L.)). Monoterpenoid esters were among the most toxic compounds tested in topical and aquatic bioassays.

Naturally occurring cyanohydrins, analogues and derivatives as potential insecticides

Several naturally occurring cyanohydrins were tested for fumigation toxicity to two insect species, the house fly (Musca domestica L) and the lesser grain borer (Rhyzopertha dominica (F)). Synthetic analogues of these compounds were tested as well. Most of the cyanohydrins tested were more toxic as fumigants to M domestica and R dominica than chloropicrin; some compounds were nearly as toxic as dichlorvos. Naturally occurring cyanohydrins were among the most toxic tested. (C) 2000 Society of Chemical Industry.

Indium trifluoride - A Lewis acid catalyst for the addition of TMSCN to aldehydes in water

Indium trifluoride promoted chemoselective additions of TMSCN to various aldehydes in water gave the respective cyanohydrins in good yields.

An improved synthesis of the antithyroid factor DL-goitrin

DL-1-Amino-3-buten-2-ol H2C=CH-CH(OH)-CH2NH2 has been synthesized in a satisfactory overall yield by reduction of the protected cyanohydrin H2C=CH-CH(OR)-CN with aluminum hydride, followed by removal of the protecting group with aqueous hydrochloric acid and treatment with potassium hydroxide.The amino alcohol is a key intermediate in a synthesis of the antithyroid goitrin reported previously.