Diethyl (hydroxymethyl)phosphonate supplier

Name
Diethyl (hydroxymethyl)phosphonate
EINECS 221-391-6
CAS No. 3084-40-0
Article Data54
CAS DataBase
Density 1.14
Solubility 500g/L at 20℃
Melting Point
Formula C5H13 O4 P
Boiling Point 124-126 ºC (3 mmHg)
Molecular Weight 168.13
Flash Point 98.7°C
Transport Information
Appearance Clear colorless to yellow viscous liquid
Safety S26;S37/39
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms Phosphonicacid, (hydroxymethyl)-, diethyl ester (6CI,7CI,8CI,9CI);(Hydroxymethyl)phosphonate diethyl ester;Diethyl (hydroxymethyl)phosphonate;Diethyl phosphonomethanol;
PSA 65.57000
LogP 1.20230

Synthetic route

: 50-00-0
formaldehyd

: 762-04-9
phosphonic acid diethyl ester

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
With triethylamine at 90℃; for 3h; Reflux;	96%
With potassium carbonate In ethanol at 75℃; for 5h;	95%
With potassium carbonate In toluene at 60℃; for 2.25h; pH=7.5 - 8;	95%

: 7016-78-6
(diethoxyphosphoryl)methyl acetate

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
With sodium ethanolate In ethanol	90%

: 50-00-0
formaldehyd

: 762-04-9, 123-22-8
Diethyl phosphonate

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
triethylamine Ambient temperature;	85.5%
With triethylamine at 90℃; for 12h;	60%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water for 1h; Ambient temperature;	53%
With triethylamine In toluene at 70℃; for 2h;

: 53920-49-3
N-methoxypyridinium p-toluenesulfonate

: 762-04-9
phosphonic acid diethyl ester

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: 23081-78-9
diethyl pyridin-2-yl-2-phosphonate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.0833333h;	A 20% B 74%

...Expand

: 762-04-9, 123-22-8
Diethyl phosphonate

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
With nitrogen; triethylamine; paraformaldehyde	60%
With nitrogen; triethylamine; paraformaldehyde	60%
With triethylamine; paraformaldehyde	57.5 g (68%)

: 50-00-0
formaldehyd

: 104-94-9
4-methoxy-aniline

: 122-52-1
triethyl phosphite

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: 81439-58-9
diethyl ester of p-N-methoxyphenylaminomethylphosphonic acid

C: 1,3,5-tris-(4-methoxybenzyl)-1,3,5-triazinane

Conditions

Conditions	Yield
In xylene at 120℃; for 1h;	A 16% B 55% C 5.5%

...Expand

: 296-38-8
trioxa-4,10,16-triaza-1,7,13-cyclooctadecane

: 50-00-0
formaldehyd

: 762-04-9
phosphonic acid diethyl ester

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: [10,16-bis-(diethoxy-phosphorylmethyl)-1,7,13-trioxa-4,10,16-triaza-cyclooctadec-4-ylmethyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With triethylamine In benzene Alkylation; Mannich reaction; substitution; Heating;	A n/a B 37%

...Expand

: 50-00-0
formaldehyd

: 94-09-7
p-aminoethylbenzoate

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: 10287-54-4
p-N,N-diethylaminobenzoic acid ethyl ester

C: 74763-68-1
diethyl 4,4′-(methylenebis(azanediyl))dibenzoate

D: 114416-19-2
Diethyl (p-ethoxycarbonylphenylaminomethyl)phosphonate

Conditions

Conditions	Yield
With triethyl phosphite In toluene at 110 - 120℃; for 6.5h;	A 32.8% B n/a C 24.4% D 23.8%

...Expand

: 50-00-0
formaldehyd

: 94-09-7
p-aminoethylbenzoate

: 122-52-1
triethyl phosphite

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: 10287-54-4
p-N,N-diethylaminobenzoic acid ethyl ester

C: 74763-68-1
diethyl 4,4′-(methylenebis(azanediyl))dibenzoate

D: 114416-19-2
Diethyl (p-ethoxycarbonylphenylaminomethyl)phosphonate

Conditions

Conditions	Yield
In toluene at 110 - 120℃; for 6.5h;	A 32.8% B n/a C 24.4% D 23.8%

...Expand

: 50-00-0
formaldehyd

: 122-52-1
triethyl phosphite

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
With 2-methoxy-phenylamine

: 296-38-8
trioxa-4,10,16-triaza-1,7,13-cyclooctadecane

: 50-00-0
formaldehyd

: 122-52-1
triethyl phosphite

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: [10,16-bis-(diethoxy-phosphorylmethyl)-1,7,13-trioxa-4,10,16-triaza-cyclooctadec-4-ylmethyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
Alkylation; Arbuzov reaction; substitution;

...Expand

: 75-11-6
diiodomethane

potassium salt of phosphoric acid diethyl ester: potassium salt of phosphoric acid diethyl ester

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
With ethanol (90 percent )

: 75-11-6
diiodomethane

: 64-17-5
ethanol

potassium salt of phosphorous acid diethyl ester: potassium salt of phosphorous acid diethyl ester

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

...Expand

: 50-00-0
formaldehyd

: 63563-83-7
bis(phthalimidylethyl)amine

: 762-04-9
phosphonic acid diethyl ester

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: ({bis-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-amino}-methyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
In ethanol; toluene for 12h; Heating; Title compound not separated from byproducts.;

...Expand

paraformaldehyde powder: paraformaldehyde powder

: 762-04-9, 123-22-8
Diethyl phosphonate

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

Conditions

Conditions	Yield
With triethylamine
N-ethyl-N,N-diisopropylamine

: 110-71-4
1,2-dimethoxyethane

: 762-04-9
phosphonic acid diethyl ester

A: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

B: 19462-41-0
diethyl 1-hydroxy-2-methoxyethylphosphonate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; potassium carbonate; copper dichloride In decane at 80℃; for 24h; Inert atmosphere; Overall yield = 53 %; Overall yield = 72 %Spectr.;

...Expand

: 103-75-3
2-ethoxy-2,3-dihydro-4H-pyran

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: (6-Ethoxy-tetrahydro-pyran-2-yloxymethyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With hydrogenchloride	98.3%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 358-23-6
trifluoromethylsulfonic anhydride

: 106938-62-9
(diethoxyphosphinyl)methyl trifluoromethanesulfonate

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane	98%
Stage #1: diethyl (1-hydroxymethyl)phosphonate With 2,6-dimethylpyridine In dichloromethane at -50℃; for 0.0833333h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -50℃; for 0.333333h;	92.4%
With pyridine In dichloromethane at -78℃; for 3h;	90%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 98-59-9
p-toluenesulfonyl chloride

: 31618-90-3
diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions

Conditions	Yield
With triethylamine In diethyl ether	97%
In water at 3 - 35℃; for 14.5h; Temperature;	95.4%
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	92%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: ethyl lithium hydroxymethylphosphonate

Conditions

Conditions	Yield
With lithium bromide In various solvent(s) at 80℃; for 0.5h;	97%

: 332-19-4
2-butoxy-(2H)-3,4-dihydropyran

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: (6-Butoxy-tetrahydro-pyran-2-yloxymethyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With hydrogenchloride	96.9%

: 5381-99-7
2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 140383-34-2
(4-Oxo-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With triethylamine In diethyl ether for 2h;	95%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 563-47-3
3-Chloro-2-methylpropene

: 108070-91-3
diethyl (4-methyl-2-oxa-4-pentenyl)phosphonate

Conditions

Conditions	Yield
Stage #1: diethyl (1-hydroxymethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 3-Chloro-2-methylpropene In tetrahydrofuran for 1h;	95%

: 513-37-1
2-methylprop-1-enyl chloride

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 108070-91-3
diethyl (4-methyl-2-oxa-4-pentenyl)phosphonate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 1h;	95%

: 140-31-8
aminoethylpiperazine

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: C11H26N3O3P

Conditions

Conditions	Yield
at 0 - 40℃; for 1h;	95%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 5970-45-6
zinc(II) acetate dihydrate

: Zn(2+)*HOCH2PO3(2-)=Zn(O3PCH2OH)

Conditions

Conditions	Yield
In water to soln. Zn(OAc)2*2H2O in water was added HOCH2P(O)(OEt)2, mixt. was stirred for 30 min, transfeed into autoclave and heated at 160°C for48 h; solid was filtered and washed with water; elem. anal.;	94%

: 110-87-2
3,4-dihydro-2H-pyran

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 71885-51-3
diethyl <<(2-tetrahydropyranyl)oxy>methyl>phosphonate

Conditions

Conditions	Yield
With trichlorophosphate In diethyl ether at 20℃; for 3h;	93%
With hydrogenchloride	90.6%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 37076-62-3
(2'R)-1-(2,3-dihydrofuran-2-yl)thymine

: (2'R,3'S,5'R)-1-(2-diethoxyphosphinoylmethoxy-3-iodotetrahydrofuran-5-yl)thymine

Conditions

Conditions	Yield
With iodine(I) bromide In dichloromethane at -25℃; for 0.833333h;	92%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 920-46-7
Methacryloyl chloride

: 60161-88-8
Methacrylsaeure-diaethoxy-phosphinylmethylester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	91%
With triethylamine; copper(l) chloride

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 98-59-9
p-toluenesulfonyl chloride

A: magnesium para-toluenesulfonate

B: 31618-90-3
diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions

Conditions	Yield
With magnesium carbonate In water at 65℃; for 20h;	A n/a B 91%

...Expand

: 524-38-9
N-hydroxyphthalimide

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 81342-57-6
diethyl (N-phthalimidyl)oxymethylphosphonate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 1h;	90%
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran Ambient temperature;	70.2%
With triphenylphosphine; diethylazodicarboxylate

: 1641-40-3
pyrocatechol phosphorochloridite

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 2-(α-diethoxyphosphinoylmethoxy)-4,5-benzo-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
With triethylamine In benzene at 5 - 10℃;	90%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 124-63-0
methanesulfonyl chloride

: 114108-84-8
diethyl <<(methylsulfonyl)oxy>methyl>phosphonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -10 - 20℃; for 2h;	90%
With triethylamine In toluene at 0 - 20℃;	89%
With triethylamine In dichloromethane at 0 - 20℃;	80%

: 1191-99-7
2,3-dihydro-2H-furan

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 79872-66-5
O,O-diethyl(2-tetrahydrofuranyloxy)methyl phosphonate

Conditions

Conditions	Yield
With hydrogenchloride	88.9%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 121-92-6
3-nitrobenzoic acid

: (diethoxyphosphoryl)methyl 3-nitrobenzoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;	87.1%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 17982-55-7
diethyl (azidomethyl)phosphonate

Conditions

Conditions	Yield
With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate In dichloromethane; benzene 0 deg C, 30 min to r.t., 20 h;	87%
With ammonia; triphenylphosphine; diethylazodicarboxylate In dichloromethane for 20h;
With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate In dichloromethane for 20h;

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 3167-63-3
diethyl chloromethylphosphonate

Conditions

Conditions	Yield
With tetrachloromethane; triphenylphosphine for 8h; Heating;	86%
With tetrachloromethane; triphenylphosphine Appel reaction;	77%
With thionyl chloride In benzene

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 294202-81-6
diethyl (4-nitrobenzenesulfonyloxy)methylphosphonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	85%
With triethylamine In dichloromethane at 0 - 25℃;

: 50551-61-6
6-methoxybenzofuran-2-carboxylic acid

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: (diethoxyphosphoryl)methyl 6-methoxybenzofuran-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 6-methoxybenzofuran-2-carboxylic acid With diisopropyl-carbodiimide In dichloromethane at 20℃; for 1h; Stage #2: diethyl (1-hydroxymethyl)phosphonate With dmap In dichloromethane for 6h; Reflux;	85%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 4152-79-8, 33156-02-4, 37105-87-6, 37105-91-2, 37105-93-4, 53597-97-0, 97059-40-0
1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose

: 5-deoxy-3-O-(diethylphosphonomethyl)-1,2-O-isopropylidenyl-D-xylose

Conditions

Conditions	Yield
With sodium hydride In mineral oil at 0 - 20℃; for 6h; Inert atmosphere;	83%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 552-16-9
ortho-nitrobenzoic acid

: (diethoxyphosphoryl)methyl 2-nitrobenzoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;	82.8%

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: 88210-96-2
5,6-dimethoxyindole-2-carboxylic acid

: C16H22NO7P

Conditions

Conditions	Yield
Stage #1: 5,6-dimethoxyindole-2-carboxylic acid With diisopropyl-carbodiimide In dichloromethane at 20℃; for 1h; Stage #2: diethyl (1-hydroxymethyl)phosphonate With dmap In dichloromethane for 6h; Reflux;	82%

: 102539-79-7
6-methoxy-1-benzothiophene-2-carboxylic acid

: 3084-40-0
diethyl (1-hydroxymethyl)phosphonate

: (diethoxyphosphoryl)methyl 6-methoxybenzothiophene-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 6-methoxybenzo[b]thiophene-2-carboxylic acid With diisopropyl-carbodiimide In dichloromethane at 20℃; for 1h; Stage #2: diethyl (1-hydroxymethyl)phosphonate With dmap In dichloromethane for 5h; Reflux;	81%

Diethyl (hydroxymethyl)phosphonate Chemical Properties

Molecule structure of Phosphonic acid,P-(hydroxymethyl)-, diethyl ester (CAS NO.3084-40-0):

IUPAC Name: Diethoxyphosphorylmethanol
Molecular Weight: 168.128081 [g/mol]
Molecular Formula: C₅H₁₃O₄P
Index of Refraction: 1.423
Molar Refractivity: 37.11 cm³
Molar Volume: 145.4 cm³
Surface Tension: 37.2 dyne/cm
Density: 1.155 g/cm³
Flash Point: 98.7 °C
Enthalpy of Vaporization: 55.37 kJ/mol
Boiling Point: 239.5 °C at 760 mmHg
Vapour Pressure: 0.00699 mmHg at 25 °C
XLogP3-AA: -0.4
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 5
Exact Mass: 168.055145
MonoIsotopic Mass: 168.055145
Topological Polar Surface Area: 55.8
Heavy Atom Count: 10
Canonical SMILES: CCOP(=O)(CO)OCC
InChI: InChI=1S/C5H13O4P/c1-3-8-10(7,5-6)9-4-2/h6H,3-5H2,1-2H3
InChIKey: RWIGWWBLTJLKMK-UHFFFAOYSA-N
EINECS: 221-391-6
Product Categories of Phosphonic acid,P-(hydroxymethyl)-, diethyl ester (CAS NO.3084-40-0): C-C Bond Formation; Horner-Wadsworth-Emmons Reagents; Olefination

Diethyl (hydroxymethyl)phosphonate Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 37/39-26-36
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3

Diethyl (hydroxymethyl)phosphonate Specification

Phosphonic acid,P-(hydroxymethyl)-, diethyl ester (CAS NO.3084-40-0) is also named as (Hydroxymethyl)phosphonic acid, diethyl ester ; Diethyl (hydroxymethyl phosphonate ; Phosphonic acid, (hydroxymethyl)-, diethyl ester ; Hydroxymethyldiethylphosphonate .

Product Name

Diethyl (hydroxymethyl)phosphonate

Synthetic route

Diethyl (hydroxymethyl)phosphonate Chemical Properties

Diethyl (hydroxymethyl)phosphonate Safety Profile

Diethyl (hydroxymethyl)phosphonate Specification

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