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N-octadecylphosphonic acid

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Name

N-octadecylphosphonic acid

EINECS 225-216-4
CAS No. 4724-47-4 Density 0.969 g/cm3
PSA 67.34000 LogP 6.42560
Solubility Insoluble in water. Melting Point 99℃
Formula C18H39O3P Boiling Point 463.6 °C at 760 mmHg
Molecular Weight 334.48 Flash Point 234.2 °C
Transport Information N/A Appearance Crystalline solid
Safety Risk Codes R36; R37; R38
Molecular Structure Molecular Structure of 4724-47-4 (N-octadecylphosphonic acid) Hazard Symbols N/A
Synonyms

Phosphonicacid, octadecyl- (6CI,7CI,8CI,9CI);1-Octadecanephosphonic acid;Octadecanephosphonic acid;Octadecylphosphonic acid;Stearylphosphonic acid;n-Octadecylphosphonic acid;

Article Data 10

N-octadecylphosphonic acid Synthetic route

112-89-0

1-Bromooctadecane

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
Stage #1: 1-Bromooctadecane With phosphoric acid; N,O-Bis(trimethylsilyl)trifluoroacetamide at 120℃;
Stage #2: With water In methanol at 20℃; for 2h; Further stages.;
99%
Stage #1: 1-Bromooctadecane With potassium hydroxide semihydrate; phosphorus; cetyltrimethylammonim bromide In water; toluene at 70℃; for 6h; Inert atmosphere;
Stage #2: With nitric acid In water at 100 - 110℃; for 2h; pH=4; Inert atmosphere;
20%
Multi-step reaction with 2 steps
1: hexane
2: concentrated aqueous HCl
View Scheme
Multi-step reaction with 2 steps
1.1: 150 °C / Inert atmosphere; Schlenk technique
2.1: trimethylsilyl bromide / dichloromethane
2.2: 3 h
View Scheme
Multi-step reaction with 2 steps
1: sodium hydride / N,N-dimethyl-formamide
2: trimethylsilyl bromide
View Scheme
16165-72-3

octadecylphosphonate de diethyle

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
Stage #1: octadecylphosphonate de diethyle With trimethylsilyl bromide In dichloromethane
Stage #2: With methanol for 3h;
70%
Multi-step reaction with 2 steps
1: CH2Cl2 / 2 h / 20 °C
2: MeOH / CH2Cl2 / 1 h
View Scheme
Stage #1: octadecylphosphonate de diethyle With trimethylsilyl bromide
Stage #2: In methanol
52235-56-0

octadecyl-phosphonic acid dibutyl ester

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
With hydrogenchloride
3220-51-7

stearylphosphonic chloride

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
With acetic acid
81302-75-2

O,O'-bis(trimethylsilyl)octadecylphosphonic acid

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
With methanol In dichloromethane for 1h;
112-88-9

octadec-1-ene

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / (tBuO)2 / 6 h / 135 °C
2: CH2Cl2 / 2 h / 20 °C
3: MeOH / CH2Cl2 / 1 h
View Scheme
112-92-5

1-octadecanol

4724-47-4

n-octadecylphosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: carbon tetrabromide; triphenylphosphine / dichloromethane
2: sodium hydride / N,N-dimethyl-formamide
3: trimethylsilyl bromide
View Scheme
4724-47-4

n-octadecylphosphonic acid

142-71-2

copper diacetate

Cu(2+)*CH3(CH2)17PO3(2-)=Cu(CH3(CH2)17PO3)

Conditions
ConditionsYield
In ethanol; water aq. soln. of CuCl2 added dropwise to soln. of acid in H2O/EtOH (3/1, v/v) (1:1 molar ratio), mixt. stirred overnight at 70°C; filtered off, washed (H2O, EtOH), dried at room temp.;94.2%

ferrous(II) sulfate heptahydrate

4724-47-4

n-octadecylphosphonic acid

879868-29-8

Fe(octadecylphosphonate)(H2O)

Conditions
ConditionsYield
With NH2CONH2 In ethanol; water under N2 atm. using Schlenk techniques; mixt. of FeSO4*7H2O, octadecylphosphonic acid, NH2CONH2 placed in ampoule purged with N2 prior addition of degassed EtOH/H2O; ampoule sealed off under vac.; heated at 80°C for a few ds; cooled; powder collected; washed (H2O); final pH of filtrate was around 7.1; elem. anal.;90%
4724-47-4

n-octadecylphosphonic acid

90-01-7

salicylic alcohol

2-stearyl-4H-1,3,2-benzodioxaphosphorin 2-oxide

Conditions
ConditionsYield
Stage #1: n-octadecylphosphonic acid With phosphorus pentachloride; trichlorophosphate at 120℃; for 2h;
Stage #2: salicylic alcohol With pyridine; dmap In tetrahydrofuran at 20℃; for 48h; Further stages.;
23%

N-octadecylphosphonic acid Specification

The CAS register number of N-octadecylphosphonic acid is 4724-47-4. It also can be called as 1-Octadecanephosphonic acid and the IUPAC name about this chemical is octadecylphosphonic acid. The molecular formula about this chemical is C18H39O3P and the molecular weight is 334.47. It belongs to the following product category which includes API intermediates. This chemical is stable under normal temperature and pressure. It is stable and incompatible with strong oxidizing agents. If you want to store it, you should keep the container tightly sealed in dry, cool places.

Physical properties about N-octadecylphosphonic acid are: (1)ACD/LogP: 7.01; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 4.07; (4)ACD/LogD (pH 7.4): 3.45; (5)ACD/BCF (pH 5.5): 143.54; (6)ACD/BCF (pH 7.4): 34.79; (7)ACD/KOC (pH 5.5): 177.39; (8)ACD/KOC (pH 7.4): 42.99; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 17; (12)Polar Surface Area: 45.34 Å2; (13)Index of Refraction: 1.465; (14)Molar Refractivity: 95.38 cm3; (15)Molar Volume: 344.8 cm3; (16)Polarizability: 37.81x10-24cm3; (17)Surface Tension: 37.5 dyne/cm; (18)Density: 0.969 g/cm3; (19)Flash Point: 234.2 °C; (20)Enthalpy of Vaporization: 79.43 kJ/mol; (21)Boiling Point: 463.6 °C at 760 mmHg; (22)Vapour Pressure: 7.02E-10 mmHg at 25 °C.

Preparation: this chemical can be prepared by 1-bromo-octadecane. This reaction will need reagent of H3PO4, BSTFA, H2O and solvent of methanol. This reaction needs two steps. The reaction time is 2 hours with reaction temperature of 120 °C and 20 °C. The yield is about 99%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(O)(O)CCCCCCCCCCCCCCCCCC
(2)InChI: InChI=1/C18H39O3P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(19,20)21/h2-18H2,1H3,(H2,19,20,21)
(3)InChIKey: FTMKAMVLFVRZQX-UHFFFAOYAI
(4)Std. InChI: InChI=1S/C18H39O3P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(19,20)21/h2-18H2,1H3,(H2,19,20,21)
(5)Std. InChIKey: FTMKAMVLFVRZQX-UHFFFAOYSA-N

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