Product Name

  • Name

    Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate

  • EINECS 213-551-9
  • CAS No. 976-56-7
  • Density 1.046 g/cm3
  • Solubility 14mg/L at 20℃
  • Melting Point 122 °C
  • Formula C19H33O4P
  • Boiling Point 417 °C at 760 mmHg
  • Molecular Weight 356.442
  • Flash Point 206 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 976-56-7 (Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate)
  • Hazard Symbols IrritantXi
  • Synonyms Phosphonicacid, (3,5-di-tert-butyl-4-hydroxybenzyl)-, diethyl ester (7CI,8CI);Phosphonicacid, [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-, diethyl ester(9CI);Diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate;Diethyl(3,5-di-tert-butyl-4-hydroxyphenyl)methanephosphonate;Irgamod 295;Irganox1222;NSC 635180;
  • PSA 65.57000
  • LogP 5.75330

Synthetic route

4-[(diethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol
794-53-6

4-[(diethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

A

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In toluene for 25h; Heating;A 94%
B n/a
...Expand
2,6-di-tert-butyl-4-methoxymethylene-phenol
87-97-8

2,6-di-tert-butyl-4-methoxymethylene-phenol

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
With aluminium trichloride In toluene at 110℃; for 10h;94%
HTMP (hydroxymethylpiperidine)

HTMP (hydroxymethylpiperidine)

2,6-di-tert-butylphenol
128-39-2

2,6-di-tert-butylphenol

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
With dimethyl amine; triethyl phosphite; paraformaldehyde90%
3,5-di-tert-butyl-4-hydroxybenzyl acetate
14387-17-8

3,5-di-tert-butyl-4-hydroxybenzyl acetate

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
at 90 - 95℃; for 4h;80%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine
88-27-7

N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
at 80 - 100℃; for 6h;77%
3,5-Di-tert-butyl-4-hydroxybenzyltrimethylammonium iodide
51917-73-8

3,5-Di-tert-butyl-4-hydroxybenzyltrimethylammonium iodide

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
In xylene for 5h; Heating;74%
N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine
88-27-7

N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine

triethyl phosphite
122-52-1

triethyl phosphite

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
at 170 - 190℃; for 5h;40%
2,6-di-tert-butylphenol
128-39-2

2,6-di-tert-butylphenol

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
With dimethyl amine; triethyl phosphite; Trimethylacetic acid; paraformaldehyde In Petroleum ether
With triethyl phosphite; paraformaldehyde In N,N-dimethyl-formamide23.0 g (65%)
petroleum

petroleum

2,6-di-tert-butylphenol
128-39-2

2,6-di-tert-butylphenol

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Conditions
ConditionsYield
With dimethyl amine; triethyl phosphite; paraformaldehyde In acetic acid
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

O-ethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)chlorophosphonate

O-ethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)chlorophosphonate

Conditions
ConditionsYield
With phosphorus pentachloride In toluene at 20℃; for 5h; Inert atmosphere;89%
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

ethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridate

ethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridate

Conditions
ConditionsYield
With phosphorus pentachloride In toluene at 30 - 60℃; for 5h; Inert atmosphere;89%
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

A

3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone
2455-14-3

3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone

B

diethyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate
128893-72-1

diethyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate

Conditions
ConditionsYield
With lead dioxide In benzene for 1h; Ambient temperature;A 5%
B 86%
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

diethyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate
128893-72-1

diethyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate

Conditions
ConditionsYield
With potassium hexacyanoferrate(III) In potassium hydroxide; benzene75%
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

α-Brom-α-(4-hydroxy-3.5-di-tert.-butyl-phenyl)methan-phosphonsaeurediethylester
128897-52-9

α-Brom-α-(4-hydroxy-3.5-di-tert.-butyl-phenyl)methan-phosphonsaeurediethylester

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane for 4h; Irradiation;55%
trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

C21H41O4PSi2
67344-32-5

C21H41O4PSi2

triethyl phosphate
78-40-0

triethyl phosphate

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

tetraethyl (3,5-di-tert-butyl-4-hydroxyphenyl)methylenediphosphonate
58186-36-0

tetraethyl (3,5-di-tert-butyl-4-hydroxyphenyl)methylenediphosphonate

Conditions
ConditionsYield
With N-Bromosuccinimide 1.) CCl4, 4 h, UV; 2.) THF, 3 h, reflux; Yield given. Multistep reaction;
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

tetraethyl (3,5-di-tert-butyl-4-hydroxyphenyl)methylenediphosphonate
58186-36-0

tetraethyl (3,5-di-tert-butyl-4-hydroxyphenyl)methylenediphosphonate

Conditions
ConditionsYield
With sodium ethanolate; lead dioxide 1) benzene; 1 h, room temp.; 2) EtOH, 1 h, reflux; Yield given. Multistep reaction;
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

Diethyl 3,5-di-tert-butyl-4-hydroxy-α-piperidinobenzylphosphonate
135347-63-6

Diethyl 3,5-di-tert-butyl-4-hydroxy-α-piperidinobenzylphosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / K3Fe(CN)6 / benzene; aq. KOH
2: 84 percent / 48 h / Ambient temperature
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

O,O'-diethyl(4-hydroxy-3,5-di-tert-butyl-α-phenylaminobenzyl)phosphonate
109874-64-8

O,O'-diethyl(4-hydroxy-3,5-di-tert-butyl-α-phenylaminobenzyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / K3Fe(CN)6 / benzene; aq. KOH
2: 94 percent / 48 h / Ambient temperature
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone
2455-14-3

3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) PbO2; 2) 5percent NaOEt / 1) benzene; 1 h, room temp.; 2) EtOH, 1 h, reflux
2: 2.5 percent / PbO2 / benzene / 1 h / Ambient temperature
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

tetraethyl (3,5-di-tert-butyl-4-hydroxyphenyl)methylenediphosphonate
58186-36-0

tetraethyl (3,5-di-tert-butyl-4-hydroxyphenyl)methylenediphosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / N-Bromsuccinimid / CCl4 / 4 h / Irradiation
2: 81 percent / tetrahydrofuran / 3 h / Heating
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

4-Trimethylsilyloxy-3.5-di-tert.-butyl-phenylmethan-bisphosphonsaeure
128897-53-0

4-Trimethylsilyloxy-3.5-di-tert.-butyl-phenylmethan-bisphosphonsaeure

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) N-Bromsuccinimid / 1.) CCl4, 4 h, UV; 2.) THF, 3 h, reflux
2: 2.) H2O / 1.) CH2Cl2, 2 h, reflux
View Scheme
Multi-step reaction with 3 steps
1: 55 percent / N-Bromsuccinimid / CCl4 / 4 h / Irradiation
2: 81 percent / tetrahydrofuran / 3 h / Heating
3: 2.) H2O / 1.) CH2Cl2, 2 h, reflux
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

4-Hydroxy-3.5-di-tert.-butyl-phenylmethan-trisphosphonsaeurehexaethylester
128911-36-4

4-Hydroxy-3.5-di-tert.-butyl-phenylmethan-trisphosphonsaeurehexaethylester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) PbO2; 2) 5percent NaOEt / 1) benzene; 1 h, room temp.; 2) EtOH, 1 h, reflux
2: 80 percent / PbO2 / benzene / 1 h / Ambient temperature
3: 25 percent / Anilin, NaOEt / ethanol / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 1) PbO2; 2) 5percent NaOEt / 1) benzene; 1 h, room temp.; 2) EtOH, 1 h, reflux
2: 80 percent / PbO2 / benzene / 1 h / Ambient temperature
3: 71 percent / 5percent NaOEt / ethanol / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1) PbO2; 2) 5percent NaOEt / 1) benzene; 1 h, room temp.; 2) EtOH, 1 h, reflux
2: 1) PbO2; 2) 5percent NaOEt / 1) benzene, 1 h, room temp.; 2) EtOH, 1 h, reflux
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

4-[bis(diethoxyphosphinoyl)methylene]-2,6-di-tert-butylcyclohexa-2,5-dien-1-one
125931-54-6

4-[bis(diethoxyphosphinoyl)methylene]-2,6-di-tert-butylcyclohexa-2,5-dien-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) PbO2; 2) 5percent NaOEt / 1) benzene; 1 h, room temp.; 2) EtOH, 1 h, reflux
2: 80 percent / PbO2 / benzene / 1 h / Ambient temperature
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid
10175-90-3

3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: H2O
View Scheme
Stage #1: diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate With trimethylsilyl bromide
Stage #2: With water
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

ethyl (3,5-di-tert-butyl-4-hydroxybenzyl)-N,N-diethylphosphoramidoate

ethyl (3,5-di-tert-butyl-4-hydroxybenzyl)-N,N-diethylphosphoramidoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphorus pentachloride / toluene / 5 h / 20 °C / Inert atmosphere
2: toluene / 30 °C / Inert atmosphere
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

ethyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-N,N-diethylphosphoramidoate

ethyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-N,N-diethylphosphoramidoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphorus pentachloride / toluene / 5 h / 20 °C / Inert atmosphere
2: toluene / 30 °C / Inert atmosphere
3: potassium hexacyanoferrate(III); potassium hydroxide / benzene; water / 6 h / 20 °C
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

ethyl N,N-diethyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonamidate

ethyl N,N-diethyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonamidate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphorus pentachloride / toluene / 5 h / 30 - 60 °C / Inert atmosphere
2: toluene / 2 h / 30 - 60 °C / Inert atmosphere
View Scheme
diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

ethyl N,N-diethyl[(3,5-di-t-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonamidate

ethyl N,N-diethyl[(3,5-di-t-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonamidate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphorus pentachloride / toluene / 5 h / 30 - 60 °C / Inert atmosphere
2: toluene / 2 h / 30 - 60 °C / Inert atmosphere
3: potassium hexacyanoferrate(III); potassium hydroxide / benzene / 6 h / 20 °C
View Scheme

Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate Specification

The Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate, with the CAS registry number 976-56-7, is also known as Antioxidant 1222. Its EINECS registry number is 213-551-9. This chemical's molecular formula is C19H33O4P and molecular weight is 356.44. Its IUPAC name is called 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol.

Physical properties of Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate: (1)ACD/LogP: 4.70; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.7; (4)ACD/LogD (pH 7.4): 4.7; (5)ACD/BCF (pH 5.5): 2207.63; (6)ACD/BCF (pH 7.4): 2207.58; (7)ACD/KOC (pH 5.5): 8613.49; (8)ACD/KOC (pH 7.4): 8613.3; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 54.57 Å2; (13)Index of Refraction: 1.491; (14)Molar Refractivity: 98.72 cm3; (15)Molar Volume: 340.4 cm3; (16)Surface Tension: 34.6 dyne/cm; (17)Density: 1.046 g/cm3; (18)Melting Point: 122 °C; (19)Flash Point: 206 °C; (20)Enthalpy of Vaporization: 69.63 kJ/mol; (21)Boiling Point: 417 °C at 760 mmHg; (22)Vapour Pressure: 1.51E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by phosphonic acid diethyl ester and 2,6-Di-tert-butyl-4-dimethylaminomethyl-phenol. The reaction time is 6 hours with reaction temperature of 80-100 ℃. The yield is about 77%.

Uses of Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate: it can be used to produce 4-diethoxyphosphinoylmethylene-2,6-di-tert-butyl-2,5-cyclohexadienone. This reaction will need reagent K3Fe(CN)6 and solvent benzene, aq. KOH. The yield is about 75%.



You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOP(=O)(CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)OCC
(2)InChI: InChI=1S/C19H33O4P/c1-9-22-24(21,23-10-2)13-14-11-15(18(3,4)5)17(20)16(12-14)19(6,7)8/h11-12,20H,9-10,13H2,1-8H3
(3)InChIKey: GJDRKHHGPHLVNI-UHFFFAOYSA-N

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