7370-58-3

Basic information

• Product Name: 3,3'-Diselenobispropionic acid
• Synonyms: 3,3'-Diselenobispropionic acid;3,3'-Diselenodipropionic acid
• CAS NO: 7370-58-3
• Molecular Formula: C₆H₁₀O₄Se₂
• Molecular Weight: 304.0612
• Mol File: 7370-58-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 134.5-135.5 °C
• Boiling Point: 493.1°Cat760mmHg
• Flash Point: 252°C
• Appearance: /
• Density: g/cm³
• PKA: 3.94±0.10(Predicted)
• CAS DataBase Reference: 3,3'-Diselenobispropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-Diselenobispropionic acid(7370-58-3)
• EPA Substance Registry System: 3,3'-Diselenobispropionic acid(7370-58-3)

Safety Data

• Hazardous Substances Data: 7370-58-3(Hazardous Substances Data)

Usage

General Description

3,3'-Diselenobispropionic acid is a chemical compound with the molecular formula C6H10O4Se2. It is a diselenide compound that contains two selenium atoms bridged by a propionic acid group. 3,3'-Diselenobispropionic acid is a key component in the development of selenium-based drugs and has shown potential as a therapeutic agent for the treatment of various diseases, including cancer and viral infections. It also exhibits antioxidant properties and has been studied for its potential role in reducing oxidative stress and inflammation in the body. Additionally, 3,3'-Diselenobispropionic acid has been investigated for its potential use in nanotechnology applications, such as in the synthesis of selenium-containing nanoparticles for biomedical purposes. Overall, this compound has garnered interest for its potential therapeutic and industrial applications due to its unique chemical structure and biological properties.

Synthetic route

3-Bromopropionic acid (590-92-1) → 3,3'-diselenodipropanoic acid (7370-58-3)

Conditions	Yield
With sodium diselenide In water at 20℃; for 3h; Inert atmosphere;	87%
With selenium; sodium tetrahydroborate; water; sodium carbonate at 20℃; for 12h; pH=8; Inert atmosphere;	62%
With disodium diselenide	52%

chloropropionic acid (107-94-8) → 3,3'-diselenodipropanoic acid (7370-58-3)

Conditions	Yield
With selenium; sodium tetrahydroborate In water at 25℃; for 16h;	81.3%

β-Propiolactone (57-57-8) → 3,3'-diselenodipropanoic acid (7370-58-3)

Conditions	Yield
With sodium selenide; water

3-selenocyanatopropanoic acid (18207-08-4) → 3,3'-diselenodipropanoic acid (7370-58-3)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + 3-selenocyanatopropanoic acid (18207-08-4) → 3,3'-diselenodipropanoic acid (7370-58-3)

potassium salt of/the/ 3-chloro-propionic acid → 3,3'-diselenodipropanoic acid (7370-58-3)

Conditions	Yield
With potassium selenide; water

chloropropionic acid (107-94-8) + sodium diselenide → 3,3'-diselenodipropanoic acid (7370-58-3)

Conditions	Yield
at 20℃; for 4h; pH=8; Inert atmosphere;

3,3'-diselenodipropanoic acid (7370-58-3) + aniline (62-53-3) → 3,3′-diselanediylbis(N-phenylpropanamide)

Conditions	Yield
Stage #1: 3,3'-diselenodipropanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Stage #2: aniline at 20℃; for 14h;	80%
Stage #1: 3,3'-diselenodipropanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Cooling with ice; Stage #2: aniline at 20℃; for 14h;	80%

bis(η3-allyl-μ-chloropalladium(II)) + 3,3'-diselenodipropanoic acid (7370-58-3) → [Pd(μ-SeCH2CH2COOH)(η3-C3H5)]3

Conditions	Yield
With NaBH4 In water; acetone to soln. Pd complex in acetone aq. soln. NaSeCH2CH2COOH prepared in situby reaction (SeCH2CH2COOH)2 with NaBH4 soln. Pd complex was added, stir red for 0.5 h; ppt. was filtered and washed with ether; elem. anal.;	78%

1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione (1585-90-6) + 3,3'-diselenodipropanoic acid (7370-58-3) → bis(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl) 3,3'-diselanediyldipropionate

Conditions	Yield
Stage #1: 1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Stage #2: 3,3'-diselenodipropanoic acid In dichloromethane at 0 - 20℃; for 24.5h;	75%
Stage #1: 1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione With dmap; dicyclohexyl-carbodiimide for 0.5h; Steglich Esterification; Cooling with ice; Stage #2: 3,3'-diselenodipropanoic acid at 20℃; for 24.5h; Steglich Esterification; Cooling with ice;	70%
Stage #1: 1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Cooling with ice; Stage #2: 3,3'-diselenodipropanoic acid In dichloromethane at 20℃; for 24.5h; Cooling with ice;	63%

3,3'-diselenodipropanoic acid (7370-58-3) + propargyl alcohol (107-19-7) → dipropargyl 3,3-diselenium dipropionate

Conditions	Yield
Stage #1: propargyl alcohol With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice; Stage #2: 3,3'-diselenodipropanoic acid In tetrahydrofuran at 20℃; for 24.5h; Cooling with ice;	68.5%

methanol (67-56-1) + 3,3'-diselenodipropanoic acid (7370-58-3) → diselenodipropionic acid dimethyl ester (136397-82-5)

Conditions	Yield
With sulfuric acid for 24h; Heating;	68%
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

furan-2-ylmethanamine (617-89-0) + 3,3'-diselenodipropanoic acid (7370-58-3) → C16H20N2O4Se2

Conditions	Yield
Stage #1: furan-2-ylmethanamine With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Cooling with ice; Stage #2: 3,3'-diselenodipropanoic acid In dichloromethane at 20℃; for 24.5h; Cooling with ice;	67%

ethylenediamine platinum(II) nitrate (50475-22-4) + 3,3'-diselenodipropanoic acid (7370-58-3) → Pt(H2NC2H4NH2)((OOCC2H4Se)2) (1367708-23-3)

Conditions	Yield
With NaOH In water to stirred soln. of Pt-complex aq. NaOH added slowly, stirred for ca. 20min, acid added at room temp., stirred for 2 h; soln. concd. (vac.), ppt. washed (ethanol), dried (vac.), recrystd. (H2O/ethanol); elem. anal.;	65%

3,3'-diselenodipropanoic acid (7370-58-3) + Propargylamine (2450-71-7) → C12H16N2O2Se2

Conditions	Yield
Stage #1: Propargylamine With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Cooling with ice; Stage #2: 3,3'-diselenodipropanoic acid In dichloromethane at 20℃; for 24.5h; Cooling with ice;	65%

3,3'-diselenodipropanoic acid (7370-58-3) + cholesterol (57-88-5) → C60H98O4Se2

Conditions	Yield
Stage #1: 3,3'-diselenodipropanoic acid With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Stage #3: cholesterol In dichloromethane at 20℃; Inert atmosphere;	64%

[Pd2Cl2(μ-Cl)2(P-n-Pr3)2] + 3,3'-diselenodipropanoic acid (7370-58-3) → [Pd2Cl2(μ-SeCH2CH2COOH)2(PnPr3)2] + [Pd3Cl2(μ-SeCH2CH2COOH)4(PnPr3)2]

Conditions

Yield

With NaBH4; aq. NH3; conc. H2SO4 In water; acetone (SeCH2CH2COOH)2, NaBH4, NH3 soln., distilled water mixed, stirred under Ar, conc. H2SO4 added, acetone soln. of Pd complex added, stirred for 1 h at room temp.; evapd. under vac., residue washed with water, dried under vac., extracted with CH2Cl2, filtered, concentrated, layered with hexane-acetone, cooled, detd. by (1)H NMR, (31)P NMR, (77)Se NMR, elem.anal.;

A 60% B 8%

7-hydroxy-2H-chromen-2-one (93-35-6) + 3,3'-diselenodipropanoic acid (7370-58-3) → C24H18O8Se2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 16h; Inert atmosphere;	60%

3,3'-diselenodipropanoic acid (7370-58-3) + 2Pd(2+)*4Cl(1-)*2P(CH3)(C6H5)2=[Pd2Cl4(P(CH3)(C6H5)2)2] → 2Pd(2+)*2Cl(1-)*2SeCH2CH2C(O)OH(1-)*2P(CH3)(C6H5)2=[Pd2Cl2(SeCH2CH2COOH)2(P(CH3)(C6H5)2)2]

Conditions

Yield

With NaBH4; aq. NH3; conc. H2SO4 In water; acetone (SeCH2CH2COOH)2, NaBH4, NH3 soln., distilled water mixed, stirred under Ar, conc. H2SO4 added, acetone soln. of Pd complex added, stirred for 1 h at room temp.; evapd. under vac., residue washed with water, dried under vac., extracted with CH2Cl2, filtered, concentrated, layered with hexane-acetone, cooled, detd. by (1)H NMR, (31)P NMR, (77)Se NMR, elem.anal., XRD;

54%

3,3'-diselenodipropanoic acid (7370-58-3) + 1,2-diamino-benzene (95-54-5) → C18H22N4O2Se2 (1639895-72-9)

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile at 20℃; Inert atmosphere;	54%

3,3'-diselenodipropanoic acid (7370-58-3) + 4-(aminomethyl)benzonitrile hydrochloride → 3,3'-diselanediylbis(N-(4-cyanobenzyl)propanamide)

Conditions	Yield
With triethylamine In tetrahydrofuran; dichloromethane at 0 - 20℃; for 0.208333h; Inert atmosphere;	52%

[Pt2Cl2(μ-Cl)2(P-n-Pr3)2] + 3,3'-diselenodipropanoic acid (7370-58-3) → [Pt2Cl2(μ-SeCH2CH2COOH)2(PnPr3)2]

Conditions

Yield

With NaBH4; aq. NH3; conc. H2SO4 In water; acetone (SeCH2CH2COOH)2, NaBH4, NH3 soln., distilled water mixed, stirred under Ar, conc. H2SO4 added, acetone soln. of Pt complex added, stirred for 1 h at room temp.; evapd. under vac., residue washed with water, dried under vac., extracted with CH2Cl2, filtered, concentrated, layered with hexane-acetone, cooled, detd. by (1)H NMR, (31)P NMR, (77)Se NMR, (195)Pt NMR, elem.anal.;

50%

3,3'-diselenodipropanoic acid (7370-58-3) → 3,3'-diselenodipropionic anhydride

Conditions	Yield
With acetyl chloride at 65℃; for 2h;	49.3%

3,3'-diselenodipropanoic acid (7370-58-3) + 2-amino-phenol (95-55-6) → C18H20N2O4Se2 (1639895-71-8)

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile at 20℃; Inert atmosphere;	36%

3,3'-diselenodipropanoic acid (7370-58-3) + taxol (33069-62-4) → C100H108N2O30Se2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	35%

propan-1-ol (71-23-8) + 3,3'-diselenodipropanoic acid (7370-58-3) → 4,5-diselena-octanedioic acid dipropyl ester

Conditions	Yield
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

2-ethoxy-ethanol (110-80-5) + 3,3'-diselenodipropanoic acid (7370-58-3) → 4,5-diselena-octanedioic acid bis-(2-ethoxy-ethyl ester)

Conditions	Yield
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

ethanol (64-17-5) + 3,3'-diselenodipropanoic acid (7370-58-3) → bis(2-carboxyethylethyl) diselenide (86247-54-3)

Conditions	Yield
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

2-methoxy-ethanol (109-86-4) + 3,3'-diselenodipropanoic acid (7370-58-3) → 4,5-diselena-octanedioic acid bis-(2-methoxy-ethyl ester)

Conditions	Yield
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

2-Butoxyethanol (111-76-2) + 3,3'-diselenodipropanoic acid (7370-58-3) → 4,5-diselena-octanedioic acid bis-(2-butoxy-ethyl ester)

Conditions	Yield
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

3,3'-diselenodipropanoic acid (7370-58-3) → (+/-)-2-methyl-3-selena-adipic acid (20846-73-5)

Conditions	Yield
With sodium amalgam Behandlung mit 2-Brom-propionsaeure in neutraler wss.Loesung;

3,3'-diselenodipropanoic acid (7370-58-3) → 3-selenino-propionic acid (55509-78-9)

Conditions	Yield
With dihydrogen peroxide; acetone
With nitric acid at 45℃;

3,3'-diselenodipropanoic acid (7370-58-3) + butan-1-ol (71-36-3) → 4,5-diselena-octanedioic acid dibutyl ester

Conditions	Yield
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;

Upstream product

• 57-57-8 β-Propiolactone 
• 7647-01-0 hydrogenchloride 
• 18207-08-4 3-selenocyanatopropanoic acid 
• 107-94-8 chloropropionic acid 
• 590-92-1 3-Bromopropionic acid 

Downstream Products

• 43169-97-7 3'-(4-Methylbenzylseleno)-propionsaeure 
• 1639895-72-9 C₁₈H₂₂N₄O₂Se₂ 
• 1582790-34-8 C₁₀H₁₀O₄SSe 
• 1155-51-7 4,4'-Dithiobisbenzoic acid 
• 34835-05-7 3-(4-Nitrobenzylseleno)propionsaeure 
• 34835-25-1 3-(2,4-Dinitro-phenylselanyl)-propionic acid 
• 43169-99-9 3'-(4-Bromphenylseleno)-propionsaeure 
• 6926-05-2 3-benzylselenopropanoic acid 
• 43170-35-0 3-(β-Phenylethylseleno)-propionsaeure 

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