632-07-5

Basic information

• Product Name: Propanoic acid, 2-cyano-
• Synonyms: Propanoic acid, 2-cyano-;alpha-Cyanopropionic acid;NSC 528442
• CAS NO: 632-07-5
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.088
• Mol File: 632-07-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 35°C
• Boiling Point: 185.54°C (rough estimate)
• Flash Point: 118.1°C
• Appearance: /
• Density: 1.1400
• Vapor Pressure: 0.00178mmHg at 25°C
• Refractive Index: 1.4166 (estimate)
• Storage Temp.: 2-8°C
• PKA: 2.57±0.10(Predicted)
• CAS DataBase Reference: Propanoic acid, 2-cyano-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2-cyano-(632-07-5)
• EPA Substance Registry System: Propanoic acid, 2-cyano-(632-07-5)

Safety Data

• Hazardous Substances Data: 632-07-5(Hazardous Substances Data)

Usage

General Description

Propanoic acid, 2-cyano- is a chemical compound with the molecular formula C4H5NO2. It is also known as 2-cyanopropanoic acid and is a colorless liquid with a pungent odor. Propanoic acid, 2-cyano- is commonly used in the synthesis of pharmaceuticals and agrochemicals. It is also used as an intermediate in the production of dyes, perfumes, and other organic compounds. Propanoic acid, 2-cyano- is considered to be a moderately hazardous substance, and appropriate safety measures should be taken when handling and storing it.

InChI:InChI=1/C4H5NO2/c1-3(2-5)4(6)7/h3H,1H3,(H,6,7)

Synthetic route

ethyl 2-cyanopropionate (1572-99-2) → 2-cyanopropanoic acid (632-07-5)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; methanol; water for 1h;	98%
With lithium hydroxide; water In methanol at 20℃; for 36h;	89%
With water; potassium hydroxide In methanol at 0 - 40℃; for 2h;	85%

α-cyanomethylmalonic acid diethyl ester (17109-93-2) → 2-cyanopropanoic acid (632-07-5)

Conditions	Yield
With potassium hydroxide

cyano-methyl-malonic acid diethyl ester + KOH-solution → 2-cyanopropanoic acid (632-07-5)

potassium cyanide (151-50-8) + sodium salt of/the/ 2-bromo-propionic acid → 2-cyanopropanoic acid (632-07-5)

Conditions	Yield
With water

carbon dioxide (124-38-9) + propiononitrile (107-12-0) → 2-cyanopropanoic acid (632-07-5)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate Electrolysis;

potassium cyanide + potassium (RS)-2-chloropropionate → 2-cyanopropanoic acid (632-07-5)

Conditions	Yield
With hydrogenchloride In water Large scale;

2-cyanopropanoic acid (632-07-5) + ethanol (64-17-5) → Diethyl methylmalonate (609-08-5)

Conditions	Yield
With sulfuric acid at 20 - 80℃; for 4h; Temperature;	91.2%
at 20 - 65℃; for 3h; Temperature; Large scale;

2-cyanopropanoic acid (632-07-5) + N,0-dimethylhydroxylamine (1117-97-1) → N-methoxy-N-methyl-2-cyanopropionamide (171110-91-1)

Conditions	Yield
With dicyclohexyl-carbodiimide	83%

2-cyanopropanoic acid (632-07-5) + 2,6-diisopropylphenol (2078-54-8) → 2,6-diisopropylphenyl α-cyanopropionate

Conditions	Yield
	79%

2-cyanopropanoic acid (632-07-5) + 3-(4-(tris(4-(tert-butyl)phenyl)methyl)phenoxy)propan-1-ol (393860-73-6) → 3-(4-[tris(4-tert-butylphenyl)methyl]phenoxy)propyl 2-cyanopropanoate (1039775-71-7)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 18h;	79%

2-cyanopropanoic acid (632-07-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-cyanopropionamide (171110-91-1)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃;	73%

2-cyanopropanoic acid (632-07-5) + 2,4-dimethyl-3-pentanol (600-36-2) → diisopropylmethyl 2-cyanopropanoate (157096-36-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 23h; Ambient temperature;	68%

2-cyanopropanoic acid (632-07-5) + Mesitol (527-60-6) → 2,4,6-trimethylphenyl α-cyanopropionate

Conditions	Yield
	68%

3,5-dimethyl-1H-pyrazole (67-51-6) + 2-cyanopropanoic acid (632-07-5) → 1-(2-cyanopropanoyl)-3,5-dimethylpyrazole

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	65%

2-cyanopropanoic acid (632-07-5) + m-Anisidine (536-90-3) → 2-cyano-N-(3-methoxyphenyl)propanamide (1026971-47-0)

Conditions	Yield
With triethylamine; triphenylphosphine In tetrachloromethane; acetonitrile at 20℃; for 12h;	61.5%

2-cyanopropanoic acid (632-07-5) + 4-methoxy-aniline (104-94-9) → 2-cyano-N-(4-methoxyphenyl)propanamide

Conditions	Yield
With triethylamine; triphenylphosphine In tetrachloromethane; acetonitrile at 20℃;	59%

3-(dimethoxymethyl)-2-methoxytetrahydrofuran + 2-cyanopropanoic acid (632-07-5) + acetic anhydride (108-24-7) → methyl-4-(2-acetyloxyethyl)-2-cyano-5-methoxypenta-2,4-dienoate

Conditions	Yield
Stage #1: 3-(dimethoxymethyl)-2-methoxytetrahydrofuran; acetic anhydride With zinc(II) chloride In methanol; n-heptane; dichloromethane at 100 - 120℃; for 1.25 - 1.5h; Heating / reflux; Stage #2: 2-cyanopropanoic acid for 1h; Stage #3: In n-heptane; tert-butyl methyl ether at 0 - 60℃; for 17.5h; Heating / reflux;	52%

1,1-Diphenylmethanol (91-01-0) + 2-cyanopropanoic acid (632-07-5) → diphenylmethyl α-cyanopropionate (297746-83-9)

Conditions	Yield
	48%

2-cyanopropanoic acid (632-07-5) + 2,2,4,4-tetramethyl-3-pentanol (14609-79-1) → di(tert-butyl)methyl α-cyanopropionate (202928-05-0)

Conditions	Yield
	43%

diazomethane (186581-53-3, 908094-01-9) + 2-cyanopropanoic acid (632-07-5) → methyl 2-cyanopropionate (14618-77-0)

Conditions	Yield
With diethyl ether

2-cyanopropanoic acid (632-07-5) + ethanol (64-17-5) → ethyl 2-cyanopropionate (1572-99-2)

Conditions	Yield
With sulfuric acid

2-cyanopropanoic acid (632-07-5) + N-acetyl-N'-methylurea (623-59-6) → 6-amino-1,5-dimethylpyrimidine-2,4-(1H,3H)-dione (63959-47-7)

2-cyanopropanoic acid (632-07-5) → DL-3-aminoisobutyric acid (10569-72-9)

Conditions	Yield
Hydrogenation;

2-cyanopropanoic acid (632-07-5) → 2-cyanopropanoyl chloride (4158-25-2)

Conditions	Yield
With thionyl chloride
With diethyl ether; phosphorus pentachloride
With phosphorus pentachloride In benzene
With phosphorus pentachloride
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h;

2-cyanopropanoic acid (632-07-5) → methyl-propanedioic acid (516-05-2)

Conditions	Yield
With potassium hydroxide

2-cyanopropanoic acid (632-07-5) → 1-carboxy-1-cyano-ethylmercury (1+); hydroxide

Conditions	Yield
With acetic acid; mercury(II) oxide

2-cyanopropanoic acid (632-07-5) + phenyl isocyanate (103-71-9) → 2-cyano-propionic acid anilide (76646-62-3)

2-cyanopropanoic acid (632-07-5) + urea (57-13-6) → (2-cyano-propionyl)-urea (362058-30-8)

Conditions	Yield
With acetic anhydride

2-cyanopropanoic acid (632-07-5) + N-benzyloxyamine (622-33-3) + silver cyanate (3315-16-0) → N-(α-Methyl-cyanacetyl)-N'-benzyloxy-harnstoff (10501-93-6)

Conditions	Yield
(i) PCl5, benzene-1,4-diol, (ii) /BRN= 4304328/, (iii) /BRN= 1906691/; Multistep reaction;

2-cyanopropanoic acid (632-07-5) → 2-Chlor-2-cyan-propionsaeure-chlorid (4158-27-4)

Conditions	Yield
With phosphorus pentachloride In chlorobenzene

2-cyanopropanoic acid (632-07-5) + thiophenol (108-98-5) → 2-methyl-3-oxo-3-(phenylsulfanyl)propanoic acid (30409-97-3)

Conditions	Yield
With PPA

2-cyanopropanoic acid (632-07-5) + benzenecarbothioamide (2227-79-4) → 4-amino-5-methyl-2-phenyl-[1,3]thiazin-6-one (4318-60-9)

Conditions	Yield
With phosphorus trichloride

2-cyanopropanoic acid (632-07-5) + urethane (51-79-6) → (2-Cyano-2-methyl-acetyl)-carbamic acid ethyl ester (30515-85-6)

Conditions	Yield
In acetic acid

Upstream product

• 17109-93-2 α-cyanomethylmalonic acid diethyl ester 
• 1572-99-2 ethyl 2-cyanopropionate 
• 124-38-9 carbon dioxide 
• 107-12-0 propiononitrile 
• 151-50-8 potassium cyanide 

Downstream Products

• 76646-62-3 2-cyano-propionic acid anilide 
• 609-08-5 Diethyl methylmalonate 
• 74648-00-3 α-methyl-(2-fluoro-4-biphenylyl)acetonitrile 
• 1065124-65-3 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-((Z)-2-cyano-1-propenyl)-2,2-dimethylcyclopropane carboxylate 
• 1246640-77-6 (2,3,5,6-tetrafluoro-4-methoxymethylbenzyl) (E)-(1R,3R)-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate 
• 1039775-71-7 3-(4-[tris(4-tert-butylphenyl)methyl]phenoxy)propyl 2-cyanopropanoate 
• 1026971-47-0 2-cyano-N-(3-methoxyphenyl)propanamide 
• 4318-60-9 4-amino-5-methyl-2-phenyl-[1,3]thiazin-6-one 
• 10501-93-6 N-(α-Methyl-cyanacetyl)-N'-benzyloxy-harnstoff 
• 516-05-2 methyl-propanedioic acid 
• 10569-72-9 DL-3-aminoisobutyric acid 
• 63959-47-7 6-amino-1,5-dimethylpyrimidine-2,4-(1H,3H)-dione 
• 1572-99-2 ethyl 2-cyanopropionate 
• 14618-77-0 methyl 2-cyanopropionate 

Relevant articles and documents

Preparation method of diethyl methylmalonate by taking heteropolyacid as catalyst

The invention relates to a preparation method of diethyl methylmalonate by taking heteropolyacid as a catalyst. The method comprises the following steps: adding 2-cyanopropionic acid into ethanol fordissolving, controlling the molar ratio of 2-cyanopropionic acid to ethanol to be 1:(3-4), and transferring the obtained solution into a reaction kettle after dissolving; stirring at room temperature,adding the heteropolyacid catalyst, controlling the mass ratio of 2-cyanopropionic acid to the heteropolyacid catalyst to be 2:(1-2), controlling the temperature to be 65-80 DEG C, reacting for 3-4 h, and then ending the reaction; distilling to separate ethanol, adding ammonia water to neutralize, regulating the pH value to be neutral, and fractionating to obtain crude diethyl methylmalonate; andputting the crude diethyl methylmalonate into a rectifying tower, and carrying out reduced pressure rectification to obtain diethyl methylmalonate. Sulfuric acid is replaced with the heteropolyacid catalyst for an esterification reaction, so the method has the advantages of good selectivity, high catalytic activity, high regeneration speed and small corrosion to equipment.

Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes

The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin. A combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective cyanoalkylation of aldehydes. This synergistic catalysis protocol makes possible the coupling of two highly versatile yet orthogonal functionalities.

Active template synthesis of rotaxanes and molecular shuttles with switchable dynamics by four-component PdII-promoted Michael additions

(Chemical Equation). Taking the Michael: Rotaxanes (see structure) and molecular shuttles are prepared in up to 99% yield by successive Pd II-promoted 1,4-conjugate additions in a one-pot four-component assembly process. This process represents the first active template reaction in which the template motif is retained in the interlocked product.