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Amino tris(methylene phosphonic acid)

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Name

Amino tris(methylene phosphonic acid)

EINECS 229-146-5
CAS No. 6419-19-8 Density 2.094 g/cm3
PSA 205.26000 LogP -1.30600
Solubility 500g/L at 20℃ Melting Point ~215 °C (dec.)
Formula C3H12NO9P3 Boiling Point 746.2 °C at 760 mmHg
Molecular Weight 299.051 Flash Point 405.1 °C
Transport Information N/A Appearance colourless liquid
Safety 26-45-36/37/39-25 Risk Codes 36-34
Molecular Structure Molecular Structure of 6419-19-8 (Amino tris(methylene phosphonic acid)) Hazard Symbols IrritantXi,CorrosiveC
Synonyms

Phosphonicacid, [nitrilotris(methylene)]tri- (6CI,7CI,8CI);Phosphonic acid,[nitrilotris(methylene)]tris- (9CI);1,1,1-Nitrilotris(methylphosphonic acid);ATMP (phosphonic acid);Aminotri(methylenephosphonic acid);Briquest 301;Briquest 301-50A;Chelest PH320;Cublen AP 1;Dequest 2000;Dequest 2001;Ferrofos 509;Mayoquest 1320;NTP-A;Nitrilo-N,N,N-trimethylenephosphonic acid;Nitrilotrimethanephosphonic acid;Sequion 20H45;Sequion OA;Unihib 305;WSI 3300;[Nitrilotris(methylene)]triphosphonic acid;a,a',a''-Aminotris(methylphosphonicacid);

Article Data 15

Amino tris(methylene phosphonic acid) Synthetic route

50-00-0

formaldehyd

6419-19-8

nitrilo-tris(methylenephosphonic acid)

Conditions
ConditionsYield
With phosphoric acid; ammonia In water at 126 - 136℃; for 4h; Product distribution / selectivity;72%
With hydrogenchloride; phosphonic Acid; ammonium chloride
With ammonium chloride; phosphorus trichloride
120060-75-5

N-(triphenylmethyl)methanimine

108-24-7

acetic anhydride

A

1066-51-9

Aminomethylphosphonic acid

B

6419-19-8

nitrilo-tris(methylenephosphonic acid)

C

17261-34-6

(iminobismethylene)bisphosphonic acid

Conditions
ConditionsYield
Stage #1: acetic anhydride With phosphonic Acid at 0 - 20℃;
Stage #2: N-(triphenylmethyl)methanimine at 0℃;
Stage #3: With hydrogenchloride; water for 8h; Reflux;
A 54%
B 9 %Spectr.
C 13 %Spectr.
6806-71-9

P,P',P''-azanetriyltrimethyl-tris-phosphonic acid hexaethyl ester

6419-19-8

nitrilo-tris(methylenephosphonic acid)

Conditions
ConditionsYield
With hydrogenchloride at 130 - 140℃;
With hydrogenchloride Heating;
50-00-0

formaldehyd

A

6419-19-8

nitrilo-tris(methylenephosphonic acid)

B

2617-47-2

hydroxymethylphosphonic acid

Conditions
ConditionsYield
With ammonium chloride; phosphorus trichloride Mechanism;
3852-14-0

N,N-methylenediacetamide

A

1066-51-9

Aminomethylphosphonic acid

B

6419-19-8

nitrilo-tris(methylenephosphonic acid)

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; phosphorus trichloride 1) 1h, reflux 2) 12h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
50-00-0

formaldehyd

100-97-0

hexamethylenetetramine

A

1066-51-9

Aminomethylphosphonic acid

B

6419-19-8

nitrilo-tris(methylenephosphonic acid)

C

17261-34-6

(iminobismethylene)bisphosphonic acid

D

5995-25-5

N-methyliminobis(methylphosphonic acid)

Conditions
ConditionsYield
With phosphoric acid Mechanism; Product distribution;
50-00-0

formaldehyd

A

6419-19-8

nitrilo-tris(methylenephosphonic acid)

B

5995-25-5

N-methyliminobis(methylphosphonic acid)

Conditions
ConditionsYield
With hydrogenchloride; phosphorus(III) oxide; water; ammonium chloride at 100 - 110℃; Product distribution / selectivity; Inert atmosphere;
139-13-9

nitrilotriacetic acid

A

6419-19-8

nitrilo-tris(methylenephosphonic acid)

B

15834-10-3

aminotrismethylenephosphonic acid N-oxide

Conditions
ConditionsYield
With phosphorus(III) oxide; trifluorormethanesulfonic acid at 45 - 50℃; for 3h;A 8.5 %Spectr.
B 9.5 %Spectr.
139-13-9

nitrilotriacetic acid

6419-19-8

nitrilo-tris(methylenephosphonic acid)

Conditions
ConditionsYield
With phosphorus(III) oxide; methanesulfonic acid at 75℃; for 0.5h; Concentration; Reagent/catalyst; Time; Temperature;95.6 %Spectr.
50-00-0

formaldehyd

ammonium bicarbonate

6419-19-8

nitrilo-tris(methylenephosphonic acid)

Conditions
ConditionsYield
Stage #1: ammonium bicarbonate With hydrogenchloride; phosphorous acid at 50℃; for 4.5h; Large scale;
Stage #2: formaldehyd at 95 - 110℃; for 21h; Temperature; Large scale;

Amino tris(methylene phosphonic acid) Chemical Properties

Molecule structure of Amino Trimethylene Phosphonic Acid (ATMP) (CAS NO.6419-19-8) :

IUPAC Name: [bis(phosphonomethyl)amino]methylphosphonic acid 
Molecular Weight: 299.049963 g/mol
Molecular Formula: C3H12NO9P3
Density: 2.094 g/cm3 
Melting Point: ~215 °C
Boiling Point: 746.2 °C at 760 mmHg 
Flash Point: 405.1 °C 
Appreance: colourless liquid
Molar Volume: 142.7 cm3
Polarizability: 19.62*10-24 cm3
Surface Tension: 143.1 dyne/cm
Enthalpy of Vaporization: 118.39 kJ/mol
Vapour Pressure: 2.29E-24 mmHg at 25 °C
XLogP3-AA: -7.2
H-Bond Donor: 6
H-Bond Acceptor: 10
Rotatable Bond Count: 6
Exact Mass: 298.972491
MonoIsotopic Mass: 298.972491
Topological Polar Surface Area: 176
Heavy Atom Count: 16
Complexity: 305
Canonical SMILES: C(N(CP(=O)(O)O)CP(=O)(O)O)P(=O)(O)O
InChI: InChI=1S/C3H12NO9P3/c5-14(6,7)1-4(2-15(8,9)10)3-16(11,12)13/h1-3H2,(H2,5,6,7)(H2,8,9,10)(H2,11,12,13) InChIKey: YDONNITUKPKTIG-UHFFFAOYSA-N
EINECS: 229-146-5
Product Categories: Phosphonate antiscalant; Organic Building Blocks; Phosphonic/Phosphinic Acids; Phosphorus Compounds

Amino tris(methylene phosphonic acid) Uses

 Amino Trimethylene Phosphonic Acid (ATMP) (CAS NO.6419-19-8) is used for cooling water, boiler water, oilfield water treatment and corrosion inhibitor.

Amino tris(methylene phosphonic acid) Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 2510mg/kg (2510mg/kg)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0990-0937,
quail LD50 oral > 2510mg/kg (2510mg/kg)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0990-0937,
rabbit LD50 skin > 6310mg/kg (6310mg/kg)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0990-0937,
rat LD50 oral 2100mg/kg (2100mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(2), Pg. 67, 1984.

Amino tris(methylene phosphonic acid) Safety Profile

Hazard Codes: IrritantXi, CorrosiveC
Risk Statements: 36-34
R36: Irritating to eyes 
R34: Causes burns
Safety Statements: 26-45-36/37/39-25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible) 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S25: Avoid contact with eyes
RIDADR: 3265
WGK Germany: 1
RTECS: SZ9860000
F: 3-9
HazardClass: 8
PackingGroup: III

Amino tris(methylene phosphonic acid) Specification

 Amino Trimethylene Phosphonic Acid (ATMP) (CAS NO.6419-19-8) is also called Nitrilotris(methylene))trisphosphonic acid ; 4-01-00-03070 (Beilstein Handbook Reference) ; AI3-51572 ; Amino, tris(methylene phosphonic acid) ; Aminotri(methylene phosphonic acid) ; Aminotris(methylphosphonic acid) . Amino Trimethylene Phosphonic Acid (ATMP) (CAS NO.6419-19-8) is stable and incompatible with bases, strong oxidizing agents.

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