2697-61-2

Basic information

• Product Name: selenocystamine
• Synonyms: selenocystamine;2,2'-Diselenobis(ethanamine);2,2'-Diselenobisethanamine;NSC 308820;Bis(2-aminoethyl) diselenide
• CAS NO: 2697-61-2
• Molecular Formula: C₄H₁₂N₂Se₂
• Molecular Weight: 246.07
• Product Categories: amino acids
• Mol File: 2697-61-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 327.9°Cat760mmHg
• Flash Point: 152.1°C
• Appearance: /
• Density: g/cm³
• PKA: 8.98±0.10(Predicted)
• CAS DataBase Reference: selenocystamine(CAS DataBase Reference)
• NIST Chemistry Reference: selenocystamine(2697-61-2)
• EPA Substance Registry System: selenocystamine(2697-61-2)

Safety Data

• Hazardous Substances Data: 2697-61-2(Hazardous Substances Data)

Usage

General Description

Selenocystamine is a chemical compound that contains the element selenium. It is a derivative of cystamine, and it is commonly used in biochemical and biological research as a reagent for crosslinking proteins and other molecules. Selenocystamine is also being investigated for its potential therapeutic applications, including its ability to protect cells from oxidative damage and its anti-cancer properties. selenocystamine is considered to be a promising tool for studying the roles of selenium in biological systems and for developing new treatments for various diseases.

Synthetic route

2-chloroethanamine hydrochloride (870-24-6) → selenocystamine (2697-61-2)

Conditions	Yield
With disodium diselenide In tetrahydrofuran; water at 20℃;	73%

C14H28N2O4Se2*2C2HF3O2 → selenocystamine (2697-61-2)

Conditions	Yield
Alkaline conditions;	68%

N,N'-(3,4-diselena-hexanediyl)-bis-phthalamic acid (112349-96-9) → selenocystamine (2697-61-2)

Conditions	Yield
With hydrogenchloride at 180℃;

N,N'-dibenzoylselenocystamine (6474-42-6) → selenocystamine (2697-61-2)

Conditions	Yield
With hydrogenchloride In ethanol

2-Amino-ethan-selenoschwefelsaeure (2697-60-1) → selenocystamine (2697-61-2)

Conditions	Yield
With hydrogenchloride
With sodium hydroxide
With hydrogen sulfide In water

2-bromoethylamine hydrobromide (2576-47-8) → selenocystamine (2697-61-2)

Conditions	Yield
With methanol; selenium; magnesium

hydrogenchloride (7647-01-0) + N,N'-(3,4-diselena-hexanediyl)-bis-phthalamic acid (112349-96-9) → selenocystamine (2697-61-2) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
at 180℃;

selenium (7782-49-2) + 2-chloroethanamine hydrochloride (870-24-6) → selenocystamine (2697-61-2) + bis(2-aminoethyl) selenoether (27974-50-1)

Conditions	Yield
Stage #1: selenium With sodium tetrahydroborate; C12H18O12Pb3 In water at 20℃; for 1.33333h; Stage #2: 2-chloroethanamine hydrochloride With sodium hydroxide In water at 20℃; for 17h;

C2H6NSe(1-) (74178-32-8) + hemiselenocystamine → selenocystamine (2697-61-2)

Conditions	Yield
at 25℃; pH=7; Kinetics; aq. buffer; Inert atmosphere;

2-aminoethaneselenol (21681-94-7) + Cysteamine (60-23-1) → selenocystamine (2697-61-2) + 2,2'-dithio-bis[ethylamine] (51-85-4) + hemiselenocystamine

Conditions	Yield
With air pH=7;

C36H36N24O12*C4H12N2Se2 → selenocystamine (2697-61-2)

Conditions	Yield
With [D]-sodium hydroxide pH=12;

di-tert-butyl (diselanediylbis(ethane-2,1-diyl))dicarbamate → selenocystamine (2697-61-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Cooling with ice;

selenocystamine (2697-61-2) + C37H37N5O7 → C37H44N6O5Se2

Conditions	Yield
In dimethyl sulfoxide for 24h;	98%

selenocystamine (2697-61-2) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → di-tert-butyl (diselanediylbis(ethane-2,1-diyl))dicarbamate

Conditions	Yield
With triethylamine In water; tert-butyl alcohol Ambient temperature;	78%

selenocystamine (2697-61-2) + acryloyl chloride (814-68-6) → N,N'-bis(acryloyl)selenocystamine

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 0 - 20℃;	70%

selenocystamine (2697-61-2) + 4-(trifluoromethoxy)benzoyl chloride (36823-88-8) → C20H18F6N2O4Se2 (27914-62-1)

Conditions	Yield
With sodium hydroxide In 1,2-dichloro-ethane

selenocystamine (2697-61-2) + calcium-N-(2,4-dihydroxy-3,3-dimethylbutyryl)-β-alaninate (137-08-6, 867-80-1, 6381-62-0, 6381-63-1, 15773-29-2, 64789-49-7, 122484-60-0, 131346-21-9) → N,N'-Dipantothenoyl-selenocystamin, Selenopantethein (110057-94-8)

Conditions	Yield
(i) Et3N, H2O, (ii) ClCO2Et, DMF, (iii) /BRN= 1698299/, AcOEt; Multistep reaction;

selenocystamine (2697-61-2) → 2-aminoethaneselenol (21681-94-7)

Conditions	Yield
With ethylenediaminetetraacetic acid; potassium chloride In water-d2 Rate constant; Hg pool cathode -1.0 V vs the saturated calomel electrode, pD=7.4;
With sodium tetrahydroborate
With water; diothiothreitol
With sodium tetrahydroborate Inert atmosphere;

selenocystamine (2697-61-2) → 2-Amino-ethanseleninsaeure, Selenohypotaurin (14499-22-0)

Conditions	Yield
With dihydrogen peroxide
With GLUTATHIONE; water; NADPH; glutathione reductase Kinetics; Reagent/catalyst;

selenocystamine (2697-61-2) → 2-aminoethaneseleninic acid (3594-82-9)

Conditions	Yield
With bromine
With dihydrogen peroxide for 1h; Kinetics;

selenocystamine (2697-61-2) + 4-trifluoromethoxybenzoic acid (330-12-1) → C20H18F6N2O4Se2 (27914-62-1)

Conditions	Yield
(i) SOCl2, (ii) /BRN= 1698299/, aq. NaOH; Multistep reaction;

selenocystamine (2697-61-2) → selenocystamine dihydrochloride (3542-13-0, 16066-41-4)

Conditions	Yield
With hydrogenchloride In methanol; diethyl ether; ethyl acetate

2-chloromethyl-3-ethoxycarbonyl-4-(o-methylthiophenyl)-5-methoxycarbonyl-6-methyl-1.4-dihydro pyridine + selenocystamine (2697-61-2) → 2-(2-aminoethyl)-selenylmethyl-3-carboethoxy-5-carbomethoxy-4-(o-methylthiophenyl)-6-methyl-1,4-dihydropyridine (120074-56-8)

Conditions	Yield
With sodium tetrahydroborate In ethanol; ethyl acetate
With sodium tetrahydroborate In ethanol; ethyl acetate
With sodium tetrahydroborate In ethanol; ethyl acetate

selenocystamine (2697-61-2) → C2H8NSe + C2H6NSe(1-) (74178-32-8)

Conditions	Yield
With formate radical In water pH=7; Kinetics;

selenocystamine (2697-61-2) → C2H8NSe + 2-Amino-ethanseleninsaeure, Selenohypotaurin (14499-22-0)

Conditions	Yield
With trichloromethylperoxyl; water pH=7; Kinetics;

selenocystamine (2697-61-2) + Cysteamine (60-23-1) → hemiselenocystamine

Conditions	Yield
at 25℃; pH=7; Kinetics; aq. buffer; Inert atmosphere;

selenocystamine (2697-61-2) + cucurbituril (80262-44-8) → C36H36N24O12*C4H12N2Se2

Conditions	Yield
In water-d2 pH=7;

selenocystamine (2697-61-2) + 3-(3-Bromo-4-hydroxy-phenyl)-2-[(E)-tetrahydro-pyran-2-yloxyimino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester → (2E,2'E)-N,N'-[diselanediylbis(ethane-2,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanamide]

Conditions	Yield
With triethylamine In 1,4-dioxane; methanol for 2h;	1.338 g

Upstream product

• 112349-96-9 N,N'-(3,4-diselena-hexanediyl)-bis-phthalamic acid 
• 21681-94-7 2-aminoethaneselenol 
• 60-23-1 Cysteamine 
• 74178-32-8 C₂H₆NSe^(1-) 
• 7782-49-2 selenium 
• 870-24-6 2-chloroethanamine hydrochloride 
• 7647-01-0 hydrogenchloride 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 2697-60-1 2-Amino-ethan-selenoschwefelsaeure 
• 6474-42-6 N,N'-dibenzoylselenocystamine 

Downstream Products

• 27914-62-1 C₂₀H₁₈F₆N₂O₄Se₂ 
• 21681-94-7 2-aminoethaneselenol 
• 3542-13-0 selenocystamine dihydrochloride 
• 120074-56-8 2-(2-aminoethyl)-selenylmethyl-3-carboethoxy-5-carbomethoxy-4-(o-methylthiophenyl)-6-methyl-1,4-dihydropyridine 

Relevant articles and documents

SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes

Herein, we disclose the first set of unique selenium-containing SLAP (SiLicon Amine Protocol) reagents for the direct synthesis of C3/C5-substituted selenomorpholines and 1,4-selenazepanes fromdiverse (hetero)aldehydes under mild photocatalytic conditions. Enantiomerically pure 1,2-amino alcohol/α-amino acid versions of these heterocycles were also synthesized. Further, we have shown the late-stage modification of certain biologically active agents using the developed seleno-SLAPreagents.

Selenium and sulfur in exchange reactions: A comparative study

Cysteamine reduces selenocystamine to form hemiselenocystamine and then cystamine. The rate constants are k1 = 1.3 × 105 M-1 s-1; k-1 = 2.6 × 107 M-1 s-1; k2 = 11 M-1 s-1; and k-2 = 1.4 × 103 M-1 s-1, respectively. Rate constants for reactions of cysteine/selenocystine are similar. Reaction rates of selenium as a nucle'phile and as an electrophile are 2-3 and 4 orders of magnitude higher, respectively, than those of sulfur. Sulfides and selenides are comparable as leaving groups.

ORGANOTELLURIUM AND SELENIUM-BASED ANTIMICROBIAL ANTIMICROBIAL FORMULATIONS AND ARTICLES

The invention provides compositions and methods for treating or preventing the spread of infectious disease through topical or cutaneous contact with a formulation or article containing an organotellurium compound, or an inorganic or organic selenium compound, or formulation thereof, capable of generating superoxide radicals in the presence of an agent of infectious disease such as bacteria, viruses, fungi and protozoa.