N-(Carboxymethyl)-N-(phosphonomethyl)-glycine supplier

Name
N-(Carboxymethyl)-N-(phosphonomethyl)-glycine
EINECS 227-824-5
CAS No. 5994-61-6
Article Data28
CAS DataBase
Density 1.792 g/cm³
Solubility
Melting Point 215 °C (dec.)(lit.)
Formula C₅H₁₀NO₇P
Boiling Point 585.9 °C at 760 mmHg
Molecular Weight 227.111
Flash Point 308.2 °C
Transport Information UN 3261 8/PG 3
Appearance Neutral crystalline powder
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms Aceticacid, [(phosphonomethyl)imino]di- (6CI,7CI,8CI);AminomethylphosphonicN,N-diacetic acid;N-(Phosphonomethyl)iminodiacetic acid;Nitrilodiacetic acid methylphosphonic acid;Nitrilotris(methylene) triphonicacid;Phosphonomethyliminodiacetic acid;
PSA 145.18000
LogP -1.40720

Synthetic route

: 50-00-0
formaldehyd

: 628-87-5
iminodiacetonitrile

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
Stage #1: iminodiacetonitrile With sodium hydroxide In water at 45 - 50℃; for 1h; Stage #2: With phosphorus trichloride Stage #3: formaldehyd at 115 - 120℃; for 2h;	93.8%
Stage #1: iminodiacetonitrile With hydrogenchloride; sulfuric acid In water at 80 - 160℃; under 1500.15 - 15001.5 Torr; for 6h; Inert atmosphere; Autoclave; Stage #2: formaldehyd With phosphonic Acid In water for 3h; Pressure; Temperature; Inert atmosphere; Autoclave; Reflux;	90.52%

: 31611-66-2
Ν,Ν-biscyanomethyl glycine

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
Stage #1: Ν,Ν-biscyanomethyl glycine With methanesulfonic acid; phosphorus pentoxide In acetonitrile at 25 - 40℃; for 21h; Stage #2: With water; sodium hydroxide In acetonitrile at 90℃; for 7h; Reagent/catalyst; Time; pH-value; Temperature;	97.3%
Stage #1: Ν,Ν-biscyanomethyl glycine With phosphorus(III) oxide; methanesulfonic acid In acetonitrile at 20 - 40℃; for 21h; Stage #2: In water at 90℃; for 7h; Temperature; Time; Concentration; Reagent/catalyst;	97.3 %Spectr.

: 50-00-0
formaldehyd

: monosodium salt of iminodiacetic acid

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride; phosphorous acid In water at 115 - 120℃; for 2h;	94.1%
With hydrogenchloride; phosphonic Acid In water

: iminodiacetic acid hydrochloride

: 628-87-5
iminodiacetonitrile

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
Stage #1: iminodiacetonitrile With sodium hydroxide In water at 100 - 110℃; for 1h; Stage #2: iminodiacetic acid hydrochloride With dihydrogen peroxide; pyrographite at 80 - 100℃; for 0.5h; Stage #3: With formaldehyd; phosphoric acid at 110℃; for 3h; Reagent/catalyst;	98.5%

: 50-00-0
formaldehyd

: iminodiacetic acid monosodium

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride; phosphonic Acid In water at 80 - 110℃; for 5h; Temperature;	94.2%

: 50-00-0
formaldehyd

: 142-73-4
iminodiacetic acid

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride; phosphorous acid In water at 100 - 120℃; under 7500.75 - 9000.9 Torr;	93.1%
With phosphonic Acid for 3h; Reflux; Green chemistry;	90.3%
Stage #1: iminodiacetic acid With phosphonic Acid In water Reflux; Stage #2: formaldehyd In water at 130 - 136℃; for 1.75h; Product distribution / selectivity;	67.3%

: 10294-56-1
phosphorous acid

: 142-73-4
iminodiacetic acid

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With formaldehyd; sulfuric acid	78.2%
With formaldehyd; sulfuric acid	75.3%
With formaldehyd; sulfuric acid	74.2%
With formaldehyd; sulfuric acid In water	59.8%

: 31611-66-2
Ν,Ν-biscyanomethyl glycine

A: 5994-61-6
phosphonomethylimino-di-acetic acid

B: 76127-84-9
N,N-bis(cyanomethyl)aminomethylphosphonic acid

Conditions

Conditions	Yield
Stage #1: Ν,Ν-biscyanomethyl glycine With methanesulfonic acid; phosphorus pentoxide In acetonitrile at 25 - 30℃; for 2h; Stage #2: With water; sodium hydroxide at 25℃; Solvent; Time; Temperature; Reagent/catalyst;	A 15.1% B 37.6%
With phosphorus(III) oxide; trifluorormethanesulfonic acid In acetonitrile at 30℃; for 3h; Reagent/catalyst; Temperature; Concentration; Time;	A 13.4 %Spectr. B 65.3 %Spectr.

: 1531623-12-7
N-hydroxymethylimino diacetic acid diethyl ester

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
Stage #1: N-hydroxymethylimino diacetic acid diethyl ester With methanesulfonic acid; phosphorus pentoxide; Dimethyl phosphite at 50 - 85℃; Stage #2: With water at 85℃; for 1h; Reagent/catalyst; Time; Temperature;	61%

: 50-00-0
formaldehyd

: 77752-64-8
1,4-di(carboxymethyl)-2,5-diketopiperazine

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride In water	55%

: 110-88-3
1,3,5-Trioxan

: 6290-05-7
Diethyl iminodiacetate

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
Stage #1: 1,3,5-Trioxan; Diethyl iminodiacetate With acetic acid at 80℃; for 6h; Stage #2: With phosphorus pentoxide at 20 - 80℃; for 8h; Stage #3: With water at 100℃; for 6h;	53%

: 50-00-0
formaldehyd

: phosphorus trichloride hydrolysate

: 77752-64-8
1,4-di(carboxymethyl)-2,5-diketopiperazine

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride	88.2%

...Expand

: methyl phosphonic acid monosodium chlorine

: iminodiacetic acid disodium salt

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With chlorine; sodium iodide at 80 - 90℃; for 14h;

: 50-00-0
formaldehyd

: monosodium salt of iminodiacetic acid

: 10294-56-1
phosphorous acid

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride	97%, 91%

...Expand

: 50-00-0
formaldehyd

: iminodiacetic acid disodium salt

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride; phosphorus trichloride In water Product distribution / selectivity;
With hydrogenchloride; N-methyl N-phosphonomethylglycine; phosphorus trichloride In water Product distribution / selectivity;
With hydrogenchloride; phosphorus trichloride In water Product distribution / selectivity; N-(phosphonomethyl)iminodiacetic acid seeds;

disodium chloromethylphosphonate: disodium chloromethylphosphonate

disodium salt of bis-carboxymethyl-amine: disodium salt of bis-carboxymethyl-amine

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 1071-83-6
N-(phosphonemethyl)glycine

Conditions

Conditions	Yield
Calgon CENTAUR 80-100 mesh (149-177 μm) at 95℃; Product distribution / selectivity;	98.6%
Norit PK at 95℃; Conversion of starting material;	98.3%
Nuchar RGC at 95℃; Conversion of starting material;	98.9%

: strontium nitrate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: [(strontium)2(N-(phosphonomethyl)iminodiacetic acid(-4H))(H2O)]

Conditions

Conditions	Yield
With 1,3-di(piperidin-4-yl)propane In ethanol; water at 180℃; for 72h; pH=3.42; Autoclave;	81.63%

: 5994-61-6
phosphonomethylimino-di-acetic acid

: BaCl2*4H2O

: [(strontium)2(N-(phosphonomethyl)iminodiacetic acid(-2H))(HPO4)]

Conditions

Conditions	Yield
With 1,3-di(piperidin-4-yl)propane In ethanol; water at 180℃; for 72h; pH=2.16; Autoclave;	80.74%

: 5994-61-6
phosphonomethylimino-di-acetic acid

: barium(II) hydroxide

: [(barium)2(N-(phosphonomethyl)iminodiacetic acid(-2H))2(H2O)]

Conditions

Conditions	Yield
With 1,3-di(piperidin-4-yl)propane In ethanol; water at 150℃; for 48h; pH=2.16; Autoclave;	78.87%

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 554-95-0
benzene-1,3,5-tricarboxylic acid

: 7732-18-5
water

: magnesium oxide

: [Mg15(PMIDA)6(BTC)2(H2O)12]·6H2O

Conditions

Conditions	Yield
at 180℃; for 168h; pH=5; Autoclave;	77%

...Expand

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 554-95-0
benzene-1,3,5-tricarboxylic acid

: 6147-53-1
cobalt(II) diacetate tetrahydrate

: magnesium oxide

: [Co13Mg2(PMIDA)6(BTC)2(H2O)12]·6H2O

Conditions

Conditions	Yield
With ammonium hydroxide In water at 180℃; for 120h; pH=5; Autoclave;	77%

...Expand

: ammonium molybdate(VI) tetrahydrate

: 616-42-2
dimethylsulfite

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 1071-83-6
N-(phosphonemethyl)glycine

Conditions

Conditions	Yield
With dihydrogen peroxide In water	76%

...Expand

: erbium(III) chloride hexahydrate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 6047-25-2
iron(II) oxalate dihydrate

: [ErFe(III)(Fe(II))6(N-(phosphonomethyl)iminodiacetateH)6]*nH2O

Conditions

Conditions	Yield
With aq. NaOH In further solvent(s) to mixt. of acid, Fe oxalate, ErCl3*6H2O added eutectic mixt. of cholinechloride and malonic acid and aq. NaOH; suspn. magnetically stirred for 1 h at ambient temp.; gel transferred to react. vessel, placed in prehe ated oven (at 150°C) for 90 h; washed 3 times with EtOH with ultrasonic vibration and with water; air dried at ambient temp.;	76%

...Expand

: manganese(II) chloride tetrahydrate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 821780-71-6
Mn(H2O)(N-(phosphonomethyl)iminodiacetate)

Conditions

Conditions	Yield
With tetramethylammonium hydroxide In water High Pressure; to an aq. soln. of Mn-contg. compd. a ligand and TMAOH soln. were added with stirring; the final mixt. with a molar ratio 1 MnCl2*4H2O: 1 H4PMIDA: 4 TMAOH was crystd. in a bomb at 150°C for 5 d; the compd. was filtered and washed with distd. water; elem. anal.; detd.by powder XRD;	75%

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 554-95-0
benzene-1,3,5-tricarboxylic acid

: 7732-18-5
water

: 6018-89-9
nickel(II) acetate tetrahydrate

: magnesium carbonate

: [Mg8Ni12(OH)12(N-(phosphonomethyl)iminodiacetic acid-H4)4(1,3,5-benzenetricarboxylic acid-H3)4(H2O)16]*9H2O

Conditions

Conditions	Yield
With ammonia at 190℃; for 120h; pH=7; Temperature; pH-value;	75%

...Expand

: barium(II) nitrate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 6147-53-1
cobalt(II) diacetate tetrahydrate

: [CoBa(PMIDA)(H2O)2]·H2O

Conditions

Conditions	Yield
With ammonium hydroxide; benzene-1,3,5-tricarboxylic acid In water at 180℃; for 120h; pH=10; Autoclave;	73%

...Expand

: ammonium molybdate(VI) tetrahydrate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 1071-83-6
N-(phosphonemethyl)glycine

Conditions

Conditions	Yield
With sulphur dichloride; dihydrogen peroxide In water	71%
With dihydrogen peroxide In water	68%

: cobalt(II) chloride hexahydrate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: [H3O]6[Co4(H2O)4(N-(phosphonomethyl)iminodiacetic acid(-4H))2(N-(phosphonomethyl)iminodiacetic acid(-3H))2]*2H2O

Conditions

Conditions	Yield
With (CH3)4NOH; NH4F In ethanol High Pressure; Co salt and NH4F dissolved in EtOH; N-(phosphonomethyl)iminodiacetic acid added with vigorous stirring; Me4NOH added; molar ratio = 1:4:1:1; stirred; mixt. heated at 170°C in autoclave for 5 d; crystals filtered under vac.; washed with EtOH; dried in air; elem. anal.;	70%

: 1356855-78-1, 811431-04-6
fac-[ReI(OH2)3(CO)3](SO3CF3)

: 5994-61-6
phosphonomethylimino-di-acetic acid

: C8H7NO10PRe(2-)

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 4h; pH=Ca. 4;	68%

: oxovanadium(IV) sulfate

: 5994-61-6
phosphonomethylimino-di-acetic acid

: 144-55-8
sodium hydrogencarbonate

: 2Na(1+)*0.5V2O2(O3PCH2N(CH2CO2)2)2(4-)*5H2O=(Na4[V2O2(O3PCH2N(CH2CO2)2)2]*10H2O)0.5

Conditions

Conditions	Yield
In water addn. of NaHCO3 (to pH=2 or 4) to mixt. of V-compd. and ligand, stirringat room temp. for 24 h; EtOH addn., crystn. (4°C, 1 week; two crops), collection (filtration), washing (EtOH), drying (vac.); elem. anal.;	67%

...Expand

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Chemical Properties

IUPAC Name: 2-[Carboxymethyl(phosphonomethyl)amino]acetic acid
Molecular Formula: C₅H₁₀NO₇P
Molecular Weight: 227.11 g/mol
Canonical SMILES: O=P(CN(CC(=O)O)CC(=O)O)(O)O
InChI: InChI=1/C5H10NO7P/c7-4(8)1-6(2-5(9)10)3-14(11,12)13/h1-3H2,(H,7,8)(H,9,10)(H2,11,12,13)
EINECS: 227-824-5
Product Categories: Organic Building Blocks; Phosphonic / Phosphinic Acids; Phosphorus Compounds
XLogP3-AA: -4.6
H-Bond Donor: 4
H-Bond Acceptor: 8
Rotatable Bond Count: 6
Exact Mass: 227.019488
MonoIsotopic Mass: 227.019488
Topological Polar Surface Area: 135
Heavy Atom Count: 14
Complexity: 255
Melting Point: 215 °C (dec.)(lit.)
Index of Refraction: 1.577
Molar Refractivity: 42 cm³
Molar Volume: 126.7 cm³
Polarizability: 16.65×10^-24 cm³
Surface Tension: 105.2 dyne/cm
Density: 1.792 g/cm³
Flash Point: 308.2 °C
Enthalpy of Vaporization: 95.61 kJ/mol
Boiling Point: 585.9 °C at 760 mmHg
Vapour Pressure of N-(Carboxymethyl)-N-(phosphonomethyl)-glycine (CAS NO.5994-61-6): 3.01E-15 mmHg at 25 °C

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Safety Profile

Hazard Codes: Corrosive C
Risk Statements: 34
R34: Causes burns.
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3261 8/PG 3
WGK Germany of N-(Carboxymethyl)-N-(phosphonomethyl)-glycine (CAS NO.5994-61-6): 1

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Specification

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine (CAS NO.5994-61-6), its Synonyms are Glycine, N-(carboxymethyl)-N-(phosphonomethyl)- ; Phosphonomethyliminodiacetic acid ; N-Phosphonomethyl aminodiacetic acid .

Product Name

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine

Synthetic route

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Chemical Properties

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Safety Profile

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Specification

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