26239-55-4

Basic information

• Product Name: N-(2-Acetamido)iminodiacetic acid
• Synonyms: ADA BUFFER;ADA;N-(CARBAMOYLMETHYL)IMINODIACETIC;N-(CARBAMOYLMETHYL)IMINODIACETIC ACID;N-(2-Amino-2-oxoethyl)-N-(carboxymethyl)-glycine;N-(2-ACETAMIDO)IMINODIACETIC ACID;N-(2-ACETAMINO)-IMINODIACETIC ACID;N-(2-ACETIMIDO)IMINODIACETIC ACID
• CAS NO: 26239-55-4
• Molecular Formula: C₆H₁₀N₂O₅
• Molecular Weight: 190.15
• EINECS: 247-530-0
• Product Categories: Good's Buffers;Biochemistry;buffer
• Mol File: 26239-55-4.mol

Chemical Properties

• Melting Point: 219 °C (dec.)(lit.)
• Boiling Point: 325.64°C (rough estimate)
• Flash Point: 271.3 °C
• Appearance: White to almost white/Powder
• Density: 1.4957 (rough estimate)
• Vapor Pressure: 2E-12mmHg at 25°C
• Refractive Index: 1.5010 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 1 M NaOH: 0.05 M at 20 °C, clear, colorles
• PKA: 6.6(at 25℃)
• Water Solubility: soluble
• Merck: 14,147
• BRN: 1787181
• CAS DataBase Reference: N-(2-Acetamido)iminodiacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Acetamido)iminodiacetic acid(26239-55-4)
• EPA Substance Registry System: N-(2-Acetamido)iminodiacetic acid(26239-55-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 26239-55-4(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Molecular Biology:
N-(2-Acetamido)iminodiacetic acid is used as a biological buffer for maintaining stable pH conditions in various biochemical and molecular biology applications. It is used with sodium hydroxide and sodium chloride, providing a pH range of 5.67-7.57 with a useful pH range of 6.4-7.4.
Used in Studying Biological Buffers and Zwitterionic Compounds:
N-(2-Acetamido)iminodiacetic acid is used as a research tool for studying biological buffers and zwitterionic compounds. It has been used in a study to describe the application of scanning capacitively coupled contactless conductivity detection (SC(4)D) for the determination of pH-dependent behavior of two aminopolycarboxylates immobilized onto the surface of a monolithic capillary column.
Used in Preparing Immobilized pH Gradients:
N-(2-Acetamido)iminodiacetic acid is used as a component in the preparation of immobilized pH gradients, which are essential for two-dimensional gel electrophoresis and other separation techniques in proteomics research.

Flammability and Explosibility

Notclassified

Purification Methods

Dissolve ADA in water, add one equivalent of NaOH solution (to final pH of 8-9), then acidify with HCl to precipitate the free acid. This is filtered off, washed with water and dried in vacuo. [Beilstein 4 IV 2441.]

InChI:InChI=1/C6H10N2O5/c7-4(9)1-8(2-5(10)11)3-6(12)13/h1-3H2,(H2,7,9)(H,10,11)(H,12,13)/p-1

Synthetic route

nitrilotriacetic acid trimethyl ester (22241-07-2) → N-(2-acetamido)-3-iminodiacetic acid (26239-55-4)

Conditions	Yield
With ammonia In tetrahydrofuran at 60℃; under 7500.75 Torr; for 8h; Solvent;	82%

(N->B)phenyl[N-carbamoylmethyl-aminodiacetate-O,O',N]borane (181523-90-0) → N-(2-acetamido)-3-iminodiacetic acid (26239-55-4)

Conditions	Yield
In methanol; water refluxing (2 h); solvent removal (vac.), crystn. (acetone);	31%

carbamoylmethylimino-di-acetic acid dimethyl ester → N-(2-acetamido)-3-iminodiacetic acid (26239-55-4)

nitrilotriacetic acid (139-13-9) → N-(2-acetamido)-3-iminodiacetic acid (26239-55-4)

Conditions	Yield
With acetamide; sulfuric acid

copper(II) choride dihydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + D,L-histidine (71-00-1) → Na2[Cu(N-(2-acetamido)iminodiacetato)(histidine)(OH)]*2.5H2O

Conditions	Yield
With NaOH In ethanol; water EtOH soln. contg. metal salt added to aq. EtOH soln. contg. N-(2-acetamido)iminodiacetic acid at pH 6 (drops of aq. NaOH), aq. EtOH soln. contg.histidine at pH 9 (drops of aq. NaOH) added slowly, stirred for 4 h; ppt. filtered off, washed (EtOH), dried (vac., P4O10); elem. anal.;	90%

manganese(II) chloride tetrahydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + D,L-histidine (71-00-1) → Na[Mn(N-(2-acetamido)iminodiacetato)(histidine)(H2O)] (330589-00-9)

Conditions	Yield
With NaOH In ethanol; water EtOH soln. contg. metal salt added to aq. EtOH soln. contg. N-(2-acetamido)iminodiacetic acid at pH 6 (drops of aq. NaOH), aq. EtOH soln. contg.histidine at pH 9 (drops of aq. NaOH) added slowly, stirred for 4 h; ppt. filtered off, washed (EtOH), dried (vac., P4O10); elem. anal.;	90%

cobalt(II) chloride hexahydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + D,L-histidine (71-00-1) → Na2[Co(N-(2-acetamido)iminodiacetato)(histidine)(OH)]*0.75H2O

Conditions	Yield
With NaOH In ethanol; water EtOH soln. contg. metal salt added to aq. EtOH soln. contg. N-(2-acetamido)iminodiacetic acid at pH 6 (drops of aq. NaOH), aq. EtOH soln. contg.histidine at pH 9 (drops of aq. NaOH) added slowly, stirred for 4 h; ppt. filtered off, washed (EtOH), dried (vac., P4O10); elem. anal.;	90%

1H-imidazole (288-32-4) + malachite + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) → (imidazole)(N-carbamoylmethyliminodiacetato)copper(II) (204118-63-8, 258855-39-9)

Conditions	Yield
In water byproducts: CO2, CuO; reduced pressure; stirring; filtering, crystn. on slow evapn. (room temp., 2 weeks), filtering, washing (H2O), drying; elem. anal.;	90%

malachite + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) → bis(N-carboxymethyl-N-(2-carbamoylmethyl)glycinato)copper(II) (514790-11-5)

Conditions	Yield
In water byproducts: CO2; 0.5 mmol Cu2(CO)3(OH)2 and 1.1 mmol H2ADA, stirring, heating under vac. to remove CO2, addn. of 1 mmol H2ADA in soln., addn. of water, 1 day; coleccting, washing (water), air drying;	85%

nickel(II) chloride hexahydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + D,L-histidine (71-00-1) → Na2[Ni(N-(2-acetamido)iminodiacetato)(histidine)(OH)]*0.5H2O

Conditions	Yield
With NaOH In ethanol; water EtOH soln. contg. metal salt added to aq. EtOH soln. contg. N-(2-acetamido)iminodiacetic acid at pH 6 (drops of aq. NaOH), aq. EtOH soln. contg.histidine at pH 9 (drops of aq. NaOH) added slowly, stirred for 4 h; ppt. filtered off, washed (EtOH), dried (vac., P4O10); elem. anal.;	68%

N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + fac-[ReI(OH2)3(CO)3](SO3CF3) (1356855-78-1, 811431-04-6) + sodium hydroxide (1310-73-2) → Na[fac-Re(CO)3(ADA)]

Conditions	Yield
In water at 20℃; for 24h; pH=6 - 7;	65%

uranyl nirate hexahydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) → poly[[[diaquadioxouranium(VI)]-μ(3)-nitrilotriacetato-κ(3)O:O':O''] trihydrate]

Conditions	Yield
In water High Pressure; 1 equiv. of the amide and U-compd. were heated in H2O in a closed vesselat 220 °C; crystn. for a week, crystals were filtered off, washed with H2O, elem. anal.;	62%

malachite + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + Thiosalicylic acid (147-93-3) → 2H(1+)*Cu(H2NC(O)CH2N(CH2COO)2)(C6H4(S)COO)(H2O)(2-)*2H2O=H2[Cu(H2NC(O)CH2N(CH2COO)2)(C6H4(S)COO)(H2O)]*2H2O

Conditions	Yield
In ethanol addn. of soln. of thiosalicylic acid to suspn. of basic carbonate, slow addn. of soln. of acetamidoiminodiacetic acid (stirring; pptn.); filtration, washing (EtOH), drying (vac., over P4O10); elem. anal.;	61%

1H-imidazole (288-32-4) + basic nickel carbonate tetrahydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + water (7732-18-5) → aqua(imidazole)(N-carbamoylmethyl-iminodiacetato)nickel(II)

Conditions	Yield
In water stoich. mixt., stirred at temperatures lower than 50°, stirred for 1 h, heated and stirred at 60°C for 20 h, cooled, 2 equiv. of imidazole added; evapd. for 3 wks at room temp., filtered, crystd., elem. anal.;	60%

1H-imidazole (288-32-4) + cobalt(II) hydroxycarbonate*2H2O + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + water (7732-18-5) → aqua(imidazole)(N-carbamoylmethyl-iminodiacetato)cobalt(II)

Conditions	Yield
In water stoich. mixt., stirred at temperatures lower than 50°, stirred for 1 h, heated and stirred at 60°C for 20 h, cooled, 2 equiv. of imidazole added; evapd. for 3 wks at room temp., filtered, crystd., elem. anal.;	60%

2Co(2+)*CO3(2-)*2OH(1-)*6H2O = CoCO3*Co(OH)2*6H2O + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + Thiosalicylic acid (147-93-3) → 2H(1+)*Co(H2NC(O)CH2N(CH2COO)2)(C6H4(S)COO)(H2O)(2-)*2H2O=H2[Co(H2NC(O)CH2N(CH2COO)2)(C6H4(S)COO)(H2O)]*2H2O

Conditions	Yield
In ethanol addn. of soln. of thiosalicylic acid to suspn. of basic carbonate, slow addn. of soln. of acetamidoiminodiacetic acid (stirring; pptn.); filtration, washing (EtOH), drying (vac., over P4O10); elem. anal.;	59%

5Ni(2+)*4OH(1-)*3CO3(2-)*4H2O=3NiCO3*2Ni(OH)2*4H2O + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + Thiosalicylic acid (147-93-3) → 2H(1+)*Ni(H2NC(O)CH2N(CH2COO)2)(C6H4(S)COO)(H2O)(2-)*2H2O=H2[Ni(H2NC(O)CH2N(CH2COO)2)(C6H4(S)COO)(H2O)]*2H2O

Conditions	Yield
In ethanol addn. of soln. of thiosalicylic acid to suspn. of basic carbonate, slow addn. of soln. of acetamidoiminodiacetic acid (stirring; pptn.); filtration, washing (EtOH), drying (vac., over P4O10); elem. anal.;	58%

potassium metavanadate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + dihydrogen peroxide (7722-84-1) → K(1+)*VO(O2)N(CH2COO)2(CH2CONH2)(1-)*4H2O=K[VO(O2)N(CH2COO)2(CH2CONH2)]*4H2O

Conditions	Yield
With HCl In water stirring (0°C), pH=4 (HCl), stirring (overnight), keeping (5°C, several days); elem. anal.;	56%

vanadyl(IV) sulfate hydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) → VO(H2O)(N-(carbamoylmethyl)iminodiacetate)*2H2O

Conditions	Yield
With Ba(OH)2*8H2O In water stoich. amts.; heating and stirring ligand with hydroxide for 0.5 h (dissoln.), addn. of VOSO4, heating and spectroscopy for 0.5 h; warm filtration, cooling, crystn. on slow evapn.; elem. anal.;	53%

basic nickel carbonate tetrahydrate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + water (7732-18-5) → cis-diaqua(N-carbamoylmethyl-iminodiacetato)nickel(II) (71261-94-4)

Conditions	Yield
In water stoich. mixt., stirred at temperatures lower than 50°, stirred for 1 h, heated and stirred at 60°C for 20 h, cooled, filtered; evapd. for 3 wks at room temp., filtered, crystd., elem. anal.;	50%

ammonium thiocyanate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + lead(II) oxide → [Pb2(μ1,1-NCS)(NCS)(N-(2-carbamoylmethyl)iminodiacetate)]n

Conditions	Yield
In water High Pressure; hydrothermal synthesis; mixt. of N-(2-carbamoylmethyl)iminodiacetic acid, PbO, NH4NCS, H2O heated in a sealed Teflon-lined stainless steel autoclave at 140°C for 5 d; cooled to room temp.; washed several times with H2O and Et2O; elem. anal.;	33%

chromium chloride + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + Ag(2+)*F6Si(2-) → Ag(1+)*Cr(3+)*2C6H8N2O5(2-)

Conditions	Yield
In methanol; water at 20℃; for 168h;	26%

N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) → formaldehyd (50-00-0) + NH3

Conditions	Yield
With perchloric acid; sodium hexachloroiridate at 20℃; for 20h; Rate constant; Thermodynamic data; Mechanism; var. temp.; activation parameters: ΔS(excit.), ΔH(excit.), ΔG(excit.);

[VO(O2)(picolinamide)2]ClO4*3H2O + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + dihydrogen peroxide (7722-84-1) + vanadia → [VO(O2)(picolinamide)2][VO(O2)(carbamoylmethyliminodiacetate)]*2H2O

Conditions	Yield
In ethanol; water soln. (VO(O2)(pa)2ClO4*3H2O in aq. EtOH was added dropwise to V2O5 dissolved in H2O2 under cooling in ice bath, aq. soln. H2ada was added; crystn. at 278 K for 24 h, ppt. was filtered and dried above silica gel at 278 K;

pyridine-2-carboxylic acid amide (1452-77-3) + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + dihydrogen peroxide (7722-84-1) + vanadia → [VO(O2)(picolinamide)2][VO(O2)(carbamoylmethyliminodiacetate)]*2H2O

Conditions	Yield
In water soln. prepared by dissolving V2O5 in H2O2 under cooling in ice bath and addn. aq. H2ada was added dropwise to soln. prepared by dissolving V2O5 in H2O2 under cooling in ice bath and addn. aq picolinamide; crystn. at 278 K for 24 h, ppt. was filtered and dried above silica gel at 278 K;

N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + nickel(II) acetate tetrahydrate (6018-89-9) → [(sodium)2 nickel(II) (N-carbamoylmethyl-iminodiacetate)2(water)4]n

Conditions	Yield
In sodium hydroxide; water aq. NaOH; High Pressure; N-carbamoylmethyl-iminodiacetic acid in aq. NaOH mixed with aq. Ni(CH3COO)2*4H2O; after stirring for 5 min in air the mixture placed into Teflon-lined autoclave and heated at 160 °C for 72 h; autoclave cooled over a period of 12 h at a rate 5 K/h; crystals collected by filtration; elem. anal.;

N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + cobalt(II) diacetate tetrahydrate (6147-53-1) → [(sodium)2 cobalt(II) (N-carbamoylmethyl-iminodiacetate)2(water)4]n

Conditions	Yield
In sodium hydroxide; water aq. NaOH; High Pressure; N-carbamoylmethyl-iminodiacetic acid in aq. NaOH mixed with aq. Co(CH3COO)2*4H2O; after stirring for 5 min in air the mixture placed into Teflon-lined autoclave and heated at 160 °C for 72 h; autoclave cooled over a period of 12 h at a rate 5 K/h; crystals collected by filtration; elem. anal.;

potassium metavanadate + N-(2-acetamido)-3-iminodiacetic acid (26239-55-4) + dihydrogen peroxide (7722-84-1) → KO[VO(O2)(2,2-[(2-amino-2-oxoethyl)imino]diacetate)]

Conditions	Yield
Stage #1: potassium metavanadate; N-(2-acetamido)-3-iminodiacetic acid; dihydrogen peroxide In water at 0℃; for 0.166667h; Stage #2: With sodium hydroxide In water for 4h; pH=4;

Upstream product

• 139-13-9 nitrilotriacetic acid 
• 181523-90-0 (N->B)phenyl[N-carbamoylmethyl-aminodiacetate-O,O',N]borane 
• 22241-07-2 nitrilotriacetic acid trimethyl ester 

Downstream Products

• 50-00-0 formaldehyd 

Relevant articles and documents

Preparation process of N-(2-acetamido)-2-iminodiacetic acid

The invention discloses a preparation process of N-(2-acetamido)-2-iminodiacetic acid. The preparation process comprises the following steps: subjecting a reactant 1 with a structure as shown in a formula as described in the specification to reacting with a nitrogen-containing compound, and subjecting the obtained intermediate product to reacting with an amination reagent to obtain N-(2-acetamido)-2-iminodiacetic acid. In the formula, Y, Y1, Y2 and Y3 are respectively one selected from the group consisting of OH, OM, halogen, OR and SR; and Z is one selected from the group consisting of halogen, OH and SH. According to the invention, low-price starting raw materials are used, so cost can be greatly reduced; reaction conditions are mild, a subsequent purification process is simple, and theyield of N-(2-acetamido)-2-iminodiacetic acid is high; and the whole process disclosed by the invention is relatively simple to operate and easy to control, is beneficial for scale-up production, shortens the reaction production period, and is also beneficial to academic research and the like of N-(2-acetamido)-2-iminodiacetic acid.

Isolation of nucleic acids

A method for extracting nucleic acids from a biological material such as blood comprises contacting the mixture with a material at a pH such that the material is positively charged and will bind negatively charged nucleic acids and then eluting the nucleic acids at a pH when the said materials possess a neutral or negative charge to release the nucleic acids. The nucleic acids can be removed under mildly alkaline conditions to the maintain integrity of the nucleic acids and to allow retrieval of the nucleic acids in reagents that are immediately compatible with either storage or analytical testing.

Isolation of nucleic acids

A method for extracting nucleic acids from a biological material such as blood comprises contacting the mixture with a material at a pH such that the material is positively charged and will bind negatively charged nucleic acids and then eluting the nucleic acids at a pH when the said materials possess a neutral or negative charge to release the nucleic acids. The nucleic acids can be removed under mildly alkaline conditions to the maintain integrity of the nucleic acids and to allow retrieval of the nucleic acids in reagents that are immediately compatible with either storage or analytical testing.

Syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes

The syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes (2 to 6) and their corresponding N-alkylaminodiacetic acids (7 to 10) are reported. All compounds (except 6) were characterized by 1H, 11B (for boron heterocycles), 13C NMR, infrared spectroscopy and mass spectrometry. The 1H NMR spectrum of compound 3 shows that it is a chiral molecule, its structure was determined by homonuclear decoupling experiments, 1H NMR and HETCOR. The study of the intramolecular N → B coordination by dynamic NMR afforded a ΔG? value of 98.4 kJ mol-1 for compound 3. Copyright

Zwitterionic compounds and their n-halo derivatives for use in the treatment of clinical conditions

Zwitterionic compounds selected from: taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido)iminodiacetic acid (ADA), piperazine-N,N'bis(2-ethanesulphonic acid (PIPES), N-(2-acetamido)-2-aminoethanesulphonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulphonic acid (BES), 3-(N-morpholino)propanesulphonic (MOPS), N-N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid (TES), N-2-hydroxyethylpiperazine-N'-2-ethanesulphonic acid (HEPES), N-2-hydroxyethylpiperazine-N'3-propanesulphonic acid (H)EPPS), 2-(cyclohexylamino)ethanesulphonic acid (CHES) or 3-(cyclohexylamino)propanesulphonic acid (CAPS), and their N-halo derivatives can be used separately or in combination in the treatment of related clinical conditions by stimulating myeloperoxidase activity, which in turn stimulates hypochlorous acid production in vivo, which leads inter alia to enhanced leukotriene inactivation.

Use of zwitterionic compounds and their N-halo derivatives

Zwitterionic compounds selected from:, taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido) iminodiacetic acid (ADA), piperazine-N,N?bis(2-ethanesulphonic acid (PIPES), N-(2-acetamido)-2-aminoethanesulphonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulphonic acid (BES), 3-(N-morpholino)propanesulphonic (MOPS), N-N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid (TES), N-2-hydroxyethylpiperazine-N?-2-ethanesulphonic acid (HEPES), N-2-hydroxyethylpiperazine-N?3-propanesulphonic acid ((H)EPPS), 2-(cyclohexylamino) ethanesulphonic acid (CHES) or 3-(cyclohexylamino) propanesulphonic acid (CAPS), and their N-halo derivatives can be used separately or in combination in the treatment of related clinical conditions by stimulating myeloperoxidase activity, which in turn stimulates hypochlorous acid production in vivo, which leads inter aliato enhanced leukotriene inactivation.