4862-18-4

Basic information

• Product Name: 2,2',2''-nitrilotris(acetamide)
• Synonyms: 2,2',2''-nitrilotris(acetamide)
• CAS NO: 4862-18-4
• Molecular Formula: C₆H₁₂N₄O₃
• Molecular Weight: 188.18448
• EINECS: 225-469-0
• Mol File: 4862-18-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2',2''-nitrilotris(acetamide)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2',2''-nitrilotris(acetamide)(4862-18-4)
• EPA Substance Registry System: 2,2',2''-nitrilotris(acetamide)(4862-18-4)

Safety Data

• Hazardous Substances Data: 4862-18-4(Hazardous Substances Data)

Synthetic route

nitrilotriacetonitrile (7327-60-8) → nitrilotriacetic acid triamide (4862-18-4)

Conditions	Yield
With sulfuric acid for 0.5h; 1.) room temperature, 2.) 40 deg C, 10 min, 3. 60 deg C, 4.) -> room temperature;	98%

triethyl nitrilotriacetate (16669-54-8) → nitrilotriacetic acid triamide (4862-18-4)

Conditions	Yield
With ethanol; ammonia

Chloroacetamide (79-07-2) → nitrilotriacetic acid triamide (4862-18-4)

Conditions	Yield
With ethanol; ammonia at 100℃;

nitrilotriacetonitrile (7327-60-8) → 4-(carbamoylmethyl)piperazine-2,6-dione (24553-06-8) + nitrilotriacetic acid triamide (4862-18-4)

Conditions	Yield
With sulfuric acid; water

2,2',2''-triaminotriethylamine (4097-89-6) + acetic anhydride (108-24-7) → nitrilotriacetic acid triamide (4862-18-4)

ethanol (64-17-5) + ammonia (7664-41-7) + Chloroacetamide (79-07-2) → nitrilotriacetic acid triamide (4862-18-4) + 2,2′-iminobis(acetamide) (21954-96-1) + H-Gly-NH2 (598-41-4)

Conditions	Yield
at 100℃;

nitrilotriacetic acid triamide (4862-18-4) → 4-(carbamoylmethyl)piperazine-2,6-dione (24553-06-8)

Conditions	Yield
With sulfuric acid at 70℃; for 12h;	44%
With sulfuric acid at 70℃; for 12h;	44%
at 200 - 205℃;

nitrilotriacetic acid triamide (4862-18-4) → N-(2-Diethylamino-ethyl)-N',N'-diethyl-N-(2-ethylamino-ethyl)-ethane-1,2-diamine

Conditions	Yield
With lithium aluminium tetrahydride

nitrilotriacetic acid triamide (4862-18-4) → N-methylnitrilotriacetamide (146377-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 44 percent / conc.H2SO4 / 12 h / 70 °C 2: 61 percent / H2O View Scheme

nitrilotriacetic acid triamide (4862-18-4) + copper(II) ion → Cu(2+)*N(CH2CONH2)2(CH2COO)(1-)={Cu(N(CH2CONH2)2(CH2COO))}(1+)

Conditions	Yield
With water In water Kinetics; soln. of equimol. amt. of N(CH2CONH2)3 and Cu(II)-salt at 60°C and pH=5.2;; in soln., spectrophotometric detection;;
With H2O In water Kinetics; soln. of equimol. amt. of N(CH2CONH2)3 and Cu(II)-salt at 60°C and pH=5.2;; in soln., spectrophotometric detection;;

lead(II) nitrate + nitrilotriacetic acid triamide (4862-18-4) → [Pb(nitrilotriacetamide)(nitrate)2]2 (888472-47-7)

Conditions	Yield
In methanol mixt. of ligand and Pb(NO3)2 (molar ratio 1:1) in MeOH stored in beaker covered with Parafilm for a few d; crystals isolated; elem. anal.;

lead(II) nitrate + nitrilotriacetic acid triamide (4862-18-4) → {lead(nitrate)(nitrilotriacetamide)} nitrate

Conditions	Yield
In water slow evapn. from 1:1 aq. soln. of nitrilotriacetamide and Pb(NO3)2;

Upstream product

• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 79-07-2 Chloroacetamide 
• 4097-89-6 2,2',2''-triaminotriethylamine 
• 108-24-7 acetic anhydride 
• 7327-60-8 nitrilotriacetonitrile 
• 16669-54-8 triethyl nitrilotriacetate 

Downstream Products

• 24553-06-8 4-(carbamoylmethyl)piperazine-2,6-dione 

Relevant articles and documents

NOVEL SYNTHESES OF MONOFUNCTIONALIZED TRIAZA-CROWNS AND CYCLAMS WITH A SECONDARY AMINE GROUP ON A SIDE CHAIN

Several monofunctionalized triaza-crowns and cyclams each containing a secondary amine group on a side chain have been prepared in good yields in few steps from readily available starting materials.The X-ray crystal structure of the complex of silver ion with 1-(2-ethylamino)ethyl-4,7,10,13-tetraethyl-1,4,7,10,13-pentaazacyclopentadecane (4) shows that the nitrogen atom of the side chain interacts strongly with the silver ion.

Nitrilotriacetamide: Synthesis in concentrated sulfuric acid and stability in water

Acid hydrolysis of N(CH2CN)3 leads either nitrilotriacetamide, 1, and/or 3,5-dioxopiperazineacetamide, 4, in quantitative yield. 1 slowly and cleanly converts to 3,5-dioxopiperazineacetic acid, 5, in water, although ammonium salts prevents this reaction.