105-33-9

Usage

Uses

Used in Chemical Synthesis:
4-Chloro-3-Hydroxy Butyronitrile is utilized as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, facilitating the production of desired end products.
Used in Industrial Processes:
In certain industries, 4-Chloro-3-Hydroxy Butyronitrile is employed as an additive to enhance specific properties of materials or processes. Its incorporation can improve characteristics such as reactivity, stability, or performance, depending on the application.

InChI:InChI=1/C4H6ClNO/c5-3-4(7)1-2-6/h4,7H,1,3H2

Upstream product

• 96-23-1 1,3-Dichloro-2-propanol 
• 143-33-9 sodium cyanide 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 106-89-8 epichlorohydrin 
• 109-75-1 but-3-enenitrile 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 773837-37-9 sodium cyanide 
• 81091-27-2 4-chloro-3-trimethylsiloxybutyronitrile 
• 128993-20-4 3-Bromo-5-chloromethyl-4,5-dihydro-isoxazole 
• 135908-05-3 2-hydroxy-3-chloropropyl p-toluenesulfonate 

Downstream Products

• 86728-85-0 ethyl 4-chloro-3-hydroxybutanoate 
• 10479-81-9 (2E)-4-hydroxybut-2-enenitrile 
• 13880-89-2 3-hydroxyglutaronitrile 
• 19060-14-1 γ-Cyano-allylalkohol 
• 7659-46-3 4-chloro-trans-crotononitrile 
• 34362-21-5 3,4-dichloro-butyronitrile 
• 29331-43-9 4-chloro-3-acetoxybutyronitrile 
• 18933-33-0 (R,S)-carnitinenitrile chloride 
• 10488-68-3 methyl 4-chloro-3-hydroxybutanoate 
• 5388-37-4 3-Methyl-3-cyclohexyl-5-cyanmethyl-oxazolidinium chlorid 
• 5688-47-1 8-Methyl-3-cyanmethyl-2-oxa-8-aza-5-azonia-spiro<4.5>decan 
• 624-58-8 3,4-epoxybutanenitrile 
• 2788-28-5 (2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride 
• 1116-95-6 (D)-(+)-carnitinenitrile chloride 

Relevant academic research and scientific papers

Nitrilase-catalysed desymmetrisation of 3-hydroxyglutaronitrile: Preparation of a statin side-chain intermediate

An efficient, scaleable synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate, a potential intermediate in the synthesis of Atorvastatin (Lipitor), has been developed. The three-stage process starts with reaction of low-cost epichlorohydrin with cyanide to give 3-hydroxyglutaronitrile (3-HGN). The second stage utilises a nitrilase-catalysed desymmetrisation of 3-HGN. The nitrilase reaction has been optimized to work at 3 M (330 g/L) substrate concentration, pH 7.5,27 °C. Under these conditions, with an enzyme loading of 6 wt %, 100% conversion and 99% ee product is obtained in 16 h. This material is then esterified to give the target compound, ethyl (R)-4-cyano-3-hydroxybutyrate. The cost-effectiveness of the process is determined by three factors: use of a low-cost starting material, the introduction of the chiral centre by desymmetrisation as opposed to kinetic resolution, and the use of Pfenex Expression Technology to allow a lower-cost supply of biocatalyst.

Regiospecific opening of 1,2-epoxides with acetone cyanohydrin under mildly basic conditions

Acetone cyanohydrin with stoichiometric triethylamine opens epoxides regiospecifically to give β-hydroxy nitriles. As expected, addition of cyanide occurs at the least substituted carbon.

A New Enzymatic Synthesis of (R)-γ-Chloro-β-Hydroxybutyronitrile

A new enzymatic synthesis of (R)-γ-chloro-β-hydroxybutyronitrile from epichlorohydrin or 1,3-dichloro-2-propanol using halohydrin hydrogen-halide-lyase purified from a recombinant Escherichia coli that carried the enzyme gene of Corynebacterium sp. strain N1074 was described.

A new method for the preparation of β-hydroxy nitriles; Transformation of 3-bromo-2-isoxazolines to β-hydroxy nitriles by treatment of alkanethiolates

3-Bromo-2-isoxazolines are transformed to β-hydroxy nitriles in good yields by treatment with alkanethiolates under a very mild condition.

Preparation of (R)- and (S)-4-chloro-3-acetoxybutyronitrile using microbial resolution

A new preparation of optically active 4-chloro-3-acetoxybutyronitrile (AcBN) was developed using the resting cells of bacteria. The resolution was based on enantioselective hydrolysis of the ester function of the substrate. (R)-AcBN was prepared using Pseudomonas sp. DS-K-717, and the resulting (R)-AcBN was obtained with high enantiomeric excess of >98% with a yield of 36% during the microbial resolution step. (S)-AcBN was prepared in the same manner using the resting cells of Pseudomonas sp. DS-K-19 and showed a high enantiomeric excess of >98% with a yield of 32%. The enzyme activity was enhanced and induced by the addition of AcBN, particularly the (R)-ester hydrolysis, which was enhanced 20-fold.

Ring opening of epoxides with sodium cyanide catalyzed with Ce(OTf)4

Efficient and regioselective conversion of epoxides to β-hydroxy nitriles with sodium cyanide in the presence of catalytic amounts of Ce(OTf)4 is described under solvent free conditions.

A Cyanide-free Biocatalytic Process for Synthesis of Complementary Enantiomers of 4-Chloro-3-hydroxybutanenitrile From Allyl Chloride

A biocatalyst used for selective ring scission of (±)-5-(chloromethyl)-4, 5-dihydroisoxazole to synthesize chiral (R)-4-chloro-3-hydroxybutanenitrile (90 % ee, 39 % isolated yield) and (S)-5-(chloromethyl)-4, 5-dihydroisoxazole (99 % ee, 39 % isolated yield) was developed by site-saturated mutagenesis on aldoxime dehydratase derived from Pseudomonas chlororaphis B23 (OxdA). The positive mutant (OxdA-L318I, E=68) improved the enantiomeric ratio E by 6-fold as compared to the wild type enzyme (OxdA-wild, E=11). The racemic precursor of (±)-5-(chloromethyl)-4, 5-dihydroisoxazole, used in the reaction, can be synthesized from readily available allyl chloride without utilizing highly toxic cyanide. The enantiopure (S)-5-(chloromethyl)-4, 5-dihydroisoxazole remaining in the kinetic resolution can be transformed into corresponding chiral (S)-4-chloro-3-hydroxybutanenitrile without loss of enantiomeric excess by treating it with triethylamine in acetonitrile (99 % ee, 72 % isolated yield) or catalysis of OxdA-wild enzyme (99 % ee, 88 % isolated yield).

Ring Opening of Epoxides with Acetone Cyanohydrin Catalyzed by Lanthanoid(III) Alkoxides

Ring opening of epoxide and aziridine with acetone cyanohydrin is promoted by a catalytic amount of lanthanoid(III) alkoxide to provide β-hydroxy nitrile and β-amino nitrile, respectively.

Preparation method of 1-BOC-3-hydroxymethyl pyrrolidine

The invention discloses a preparation method of 1-Boc-3-hydroxymethyl pyrrolidine. The preparation method uses epichlorohydrin as a raw material, 3-hydroxymethyl pyrrolidine is obtained through reduction and cyclization reaction, then the 1-Boc-3-hydroxymethyl pyrrolidine is prepared through Boc protection reaction, then 1-BOC-3-methyl formate pyrrolidine is prepared through carboxylation reaction and esterification reaction, and finally the 1-BOC-3-methyl formate pyrrolidine and lithium aluminum hydride are catalyzed by a catalyst to prepare the 1-BOC-3-hydroxymethyl pyrrolidine. The preparation method is high in product synthesis rate, high in product purity and low in production cost, and the raw materials are cheap and easy to obtain.

LiOH-catalyzed simple ring opening of epoxides under solvent-free conditions

LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions. Copyright Taylor & Francis Group, LLC.