2079-89-2

Basic information

• Product Name: 3-AMINOPROPIONITRILE FUMARATE
• Synonyms: TIMTEC-BB SBB008547;3-AMINOPROPIONITRILE FUMARATE;3-AMINOPROPIONITRILE FUMARATE SALT;BIS-(3-AMINOPROPIONITRILE) FUMARATE;BETA-AMINOPROPIONITRILE MONOFUMARATE;BETA-AMINOPROPIONITRILE MONOFUMARATE SALT;3-amino-propanenitril(e)-2-butenedioate(2:1);3-amino-propionitrilfumarate(2:1)
• CAS NO: 2079-89-2
• Molecular Formula: 2C₃H₆N₂*C₄H₄O₄
• Molecular Weight: 186.17
• EINECS: 218-208-7
• Product Categories: Lysyl oxidase;Enzyme Inhibitors by Enzyme;L to;C1 to C5;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C1 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Inhibitors
• Mol File: 2079-89-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 177 °C (dec.)(lit.)
• Boiling Point: 355.5°Cat760mmHg
• Flash Point: 183°C
• Appearance: White/Crystalline Powder
• Density: g/cm³
• Vapor Pressure: 5.19E-06mmHg at 25°C
• Storage Temp.: -20°C
• Water Solubility: almost transparency
• BRN: 3573532
• CAS DataBase Reference: 3-AMINOPROPIONITRILE FUMARATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINOPROPIONITRILE FUMARATE(2079-89-2)
• EPA Substance Registry System: 3-AMINOPROPIONITRILE FUMARATE(2079-89-2)

Safety Data

• Hazard Codes: T
• Statements: 61
• Safety Statements: 53-45
• WGK Germany: 3
• RTECS: UG0700000
• TSCA: Yes
• Hazardous Substances Data: 2079-89-2(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

3-Aminopropionitrile fumarate salt has been used as a lysyl oxidase (LOX) inhibitor:to inhibit collagen cross-linking during microtissue formation and culturein LIM domain only 1 (LMO1)- or vector-expressing BE2C neuroblastoma cell line in transwell migration and invasion assayin lysyl oxidase (LOX) activity assayto study requirement of LOX activity for inducing hypoxia-inducible factor (HIF)2A-dependent stiffness in mouse organoids

Definition

ChEBI: A fumarate salt prepared from beta-aminopropionitrile by reaction of one molecule of fumaric acid for every two molecules of beta-aminopropionitrile.

Biochem/physiol Actions

3-Aminopropionitrile (β-Aminopropionitrile (BAPN)) functions as an irreversible inhibitor of lysyl oxidase (LOX), an enzyme involved in collagen cross-linking.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of NO, and CN-. See also NITRILES.

InChI:InChI=1/C4H4O4.2C3H6N2/c5-3(6)1-2-4(7)8;2*4-2-1-3-5/h1-2H,(H,5,6)(H,7,8);2*1-2,4H2/b2-1-;;

Synthetic route

di-tert-butyl dicarbonate (24424-99-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-<(tert-butoxycarbonyl)amino>propionitrile (53588-95-7)

Conditions	Yield
With triethylamine In dichloromethane for 12h; Heating;	96%
With sodium hydroxide In diethyl ether; water for 12h;	91%

β-aminopropionitrile monofumarate salt (2079-89-2) + benzyl chloroformate (501-53-1) → 3-<<(benzyloxy)carbonyl>amino>propionitrile (18877-96-8)

Conditions	Yield
With sodium hydroxide for 0.5h; Ambient temperature;	82%
With sodium hydroxide In diethyl ether; water for 4h;	35.0 g
With sodium hydroxide In diethyl ether; water for 2h; pH=10;

β-aminopropionitrile monofumarate salt (2079-89-2) + p-toluenesulfonyl chloride (98-59-9) → N-(β-cyanoethyl)-p-toluenesulfonamide (2619-22-9)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate pH=10;	78%

1-(4-fluorophenyl)-5-methyl-1,4-hexanedione (104568-68-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>-1-cyanoethane (104568-69-6)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;	73%

1-(4-methoxyphenyl)pentane-1,4-dione (2108-54-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(4-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-27-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(p-chlorophenyl)-1,4-pentanedione (53842-12-9) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(4-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-28-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-cyclohexyl-1,4-pentanedione (61771-79-7) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Cyclohexyl-5-methyl-pyrrol-1-yl)-propionitrile (123184-34-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-norborn-5-en-2-yl-pentane-1,4-dione (70353-45-6) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Bicyclo[2.2.1]hept-5-en-2-yl-5-methyl-pyrrol-1-yl)-propionitrile (123184-35-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-([1,1'-biphenyl]-4-yl)pentane-1,4-dione (63472-37-7) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Biphenyl-4-yl-5-methyl-pyrrol-1-yl)-propionitrile (123184-26-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

3,8-Diethyl-decane-4,7-dione (123184-08-7) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2,5-Bis-(1-ethyl-propyl)-pyrrol-1-yl]-propionitrile (123184-50-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(4-fluoro-phenyl)-pentane-1,4-dione (123183-95-9) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(4-Fluoro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-24-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-[2-(methoxy)phenyl]-pentane-1,4-dione (104562-48-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-31-6)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(naphthalen-2-yl)pentane-1,4-dione (123183-98-2) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Methyl-5-naphthalen-2-yl-pyrrol-1-yl)-propionitrile (123184-32-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(naphthalen-1-yl)pentane-1,4-dione (123263-79-6) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Methyl-5-naphthalen-1-yl-pyrrol-1-yl)-propionitrile (123184-33-8)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(3-Methoxy-phenyl)-pentane-1,4-dione (123183-97-1) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(3-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile (123184-30-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Cyclopropyl-4-(4-fluoro-phenyl)-butane-1,4-dione (123184-04-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Cyclopropyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-39-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Fluoro-phenyl)-5-methyl-hexane-1,4-dione (123184-10-1) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-42-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Chloro-phenyl)-5-methyl-hexane-1,4-dione + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Chloro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-48-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Bicyclo[2.2.2]oct-5-en-2-yl-pentane-1,4-dione (123183-99-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Bicyclo[2.2.2]oct-5-en-2-yl-5-methyl-pyrrol-1-yl)-propionitrile (123184-36-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(3-Fluoro-phenyl)-5-methyl-hexane-1,4-dione (123184-09-8) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(3-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (125333-93-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Methoxy-phenyl)-5-methyl-hexane-1,4-dione (123184-12-3) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Isopropyl-5-(2-methoxy-phenyl)-pyrrol-1-yl]-propionitrile (123184-44-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

5-Ethyl-1-(4-fluoro-phenyl)-heptane-1,4-dione (123184-03-2) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(1-Ethyl-propyl)-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-38-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2,5-Dimethyl-phenyl)-5-methyl-hexane-1,4-dione + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2,5-Dimethyl-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-46-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2,4-Difluoro-phenyl)-5-methyl-hexane-1,4-dione (123184-11-2) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2,4-Difluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-43-0)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Cyclobutyl-4-(4-fluoro-phenyl)-butane-1,4-dione (123184-05-4) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Cyclobutyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-40-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1,1-Diphenyl-hexane-2,5-dione (123184-00-9) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-(2-Benzhydryl-5-methyl-pyrrol-1-yl)-propionitrile (123184-37-2)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

5,5,5-Trifluoro-1-(4-fluoro-phenyl)-pentane-1,4-dione (123184-07-6) + β-aminopropionitrile monofumarate salt (2079-89-2) → 2-(4-fluorophenyl)-5-trifluoromethyl-1H-pyrrole-1-propanenitrile (104568-91-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-[3-(trifluoromethyl)phenyl]pentane-1,4-dione (123183-96-0) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Methyl-5-(3-trifluoromethyl-phenyl)-pyrrol-1-yl]-propionitrile (123184-29-2)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-Cyclohexyl-4-(4-fluoro-phenyl)-butane-1,4-dione (123184-06-5) + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-Cyclohexyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-propionitrile (123184-41-8)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

1-(2-Isopropoxy-phenyl)-5-methyl-hexane-1,4-dione + β-aminopropionitrile monofumarate salt (2079-89-2) → 3-[2-(2-Isopropoxy-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile (123184-47-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 8h; Heating;

Downstream Products

• 123184-28-1 3-[2-(4-Chloro-phenyl)-5-methyl-pyrrol-1-yl]-propionitrile 
• 123185-39-7 (4R,6R)-6-{2-[2-Cyclohexyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 104568-92-5 (4R,6R)-6-{2-[2-(4-Fluoro-phenyl)-5-trifluoromethyl-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 104568-71-0 methyl 7-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>-5-hydroxy-3-oxoheptanoate 
• 123185-42-2 (4R,6R)-6-{2-[2-(2,4-Difluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 104568-85-6 (4R,6R)-6-[2-(2-Benzhydryl-5-methyl-pyrrol-1-yl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one 
• 104568-80-1 (4R,6R)-4-Hydroxy-6-{2-[2-methyl-5-(3-trifluoromethyl-phenyl)-pyrrol-1-yl]-ethyl}-tetrahydro-pyran-2-one 
• 123185-45-5 (4R,6R)-4-Hydroxy-6-{2-[2-(2-isopropoxy-phenyl)-5-isopropyl-pyrrol-1-yl]-ethyl}-tetrahydro-pyran-2-one 
• 105356-38-5 (4R,6R)-4-Hydroxy-6-{2-[2-isopropyl-5-(2-methoxy-phenyl)-pyrrol-1-yl]-ethyl}-tetrahydro-pyran-2-one 
• 123185-46-6 (4R,6R)-6-{2-[2-(2-Chloro-phenyl)-5-isopropyl-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 123185-41-1 (4R,6R)-6-{2-[2-(2-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 104568-75-4 (4R,6R)-6-{2-[2-Cyclopropyl-5-(4-fluoro-phenyl)-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 104568-73-2 trans-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-4-hydroxy-2H-pyran-2-one 
• 123185-34-2 (4R,6R)-4-Hydroxy-6-{2-[2-(2-hydroxy-phenyl)-5-methyl-pyrrol-1-yl]-ethyl}-tetrahydro-pyran-2-one