33494-81-4

Basic information

• Product Name: DI-T-BUTYL PHOSPHORIC ACID
• Synonyms: DI-T-BUTYL PHOSPHORIC ACID;DI-TERT-BUTYL PHOSPHORIC ACID;Phosphoric acid di-tert-butyl ester;Di-tert-butyl hydrogen phosphate;Phosphoric acid,bis(1,1-dimethylethyl) ester;Phosphoric acid,bis(1,1-dimethylethyl) ester (9CI)
• CAS NO: 33494-81-4
• Molecular Formula: C₈H₁₉O₄P
• Molecular Weight: 210.21
• Mol File: 33494-81-4.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 252℃
• Flash Point: 106℃
• Appearance: /
• Density: 1.077
• Storage Temp.: 2-8°C
• PKA: 1.48±0.50(Predicted)
• CAS DataBase Reference: DI-T-BUTYL PHOSPHORIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DI-T-BUTYL PHOSPHORIC ACID(33494-81-4)
• EPA Substance Registry System: DI-T-BUTYL PHOSPHORIC ACID(33494-81-4)

Safety Data

• Hazardous Substances Data: 33494-81-4(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Di-tert-butyl phosphate (dtbp-H) is used with metal acetates in a high-yield synthetic procedure for the preparation of transition metal phosphate cages [M4(μ4-O)(dtbp)6] (M = Co, Zn).

Flammability and Explosibility

Flammable

Synthetic route

potassium di-tert-butylphosphate (33494-80-3) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With hydrogenchloride In water at 0℃;	98%
With hydrogenchloride In water at 0℃;
With hydrogenchloride In water Cooling with ice;

di-tert-butyl phosphite (13086-84-5) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
Stage #1: di-tert-butyl phosphite With potassium permanganate; potassium hydrogencarbonate In water at 0 - 60℃; for 1.75h; Stage #2: With hydrogenchloride In water at 0 - 5℃;	95%
With potassium permanganate; potassium hydrogencarbonate In water	92%
Stage #1: di-tert-butyl phosphite With potassium permanganate; sodium hydrogencarbonate In water at -5 - 25℃; for 2h; Stage #2: With hydrogenchloride In water at 0℃; pH=1 - 2;	63%

di-tert-butyl phosphite (13086-84-5) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With potassium permanganate; sodium hydrogencarbonate In water	89%
With potassium permanganate; sodium hydrogencarbonate In water Cooling with ice;	89%
Stage #1: di-tert-butyl phosphite With sodium hydrogencarbonate In water at 0℃; for 0.333333h; Stage #2: With potassium permanganate at 20℃; for 1h;	89%

tert-butyl alcohol (75-65-0) → tri-(tert-butyl) phosphate (20224-50-4) + t-butyl dihydrogenphosphate (2382-75-4) + phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis;	A 80% B n/a C n/a

C4H9Sn{O2P(OC(CH3)3)2}3 → {(C4H9Sn(S)OP(OH)(OC(CH3)3)2)3S}(1+)*O2P(OC(CH3)3)2(1-)*2H2S*H2O={Sn3S4P3O12H84C36}{O4PC8H18}*2H2S*H2O + phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With hydrogen sulfide In benzene passing H2S through a benzene soln. of tin-compd. at room temp.;

8-bromo-7-hydroxyquinoline (90224-71-8) + concentrated sodium thiosulfate + di-tert-butyl N,N-diethylphosphoramidite (117924-33-1) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With 1H-tetrazole; tert.-butylhydroperoxide; triethylamine In tetrahydrofuran; water; acetonitrile

di-tert-butyl N,N-diethylphosphoramidite (117924-33-1) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With 1H-tetrazole; tert.-butylhydroperoxide In tetrahydrofuran

di-tert-butyl phosphite (13086-84-5) + pyrographite (7440-44-0) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With potassium hydrogencarbonate In potassium permanganate; water

di-tert-butyl phosphite (13086-84-5) → phosphoric acid di-tert-butyl ester (33494-81-4) + 1,1-dimethylethyl diphosphate

Conditions	Yield
Stage #1: di-tert-butyl phosphite With iodine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With pyridine; water In tetrahydrofuran at 20℃; Reagent/catalyst; Solvent; Inert atmosphere;

tert-butyl alcohol (75-65-0) → phosphoric acid di-tert-butyl ester (33494-81-4)

Conditions	Yield
With phosphorus trichloride at 40 - 50℃; for 1h;

phosphoric acid di-tert-butyl ester (33494-81-4) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → di-tert-butyl phosphoric acid tetra-n-butylammonium salt (68695-48-7)

Conditions	Yield
In water; acetone Cooling with ice;	99%
In acetone at -10 - -5℃; for 0.5h;	37%
In methanol at 0℃;
In methanol

phosphoric acid di-tert-butyl ester (33494-81-4) + [Mn(OAc)(2,2′-bipyridine)2](ClO4)(H2O) → C56H68Mn2N8O8P2(2+)*2ClO4(1-)

Conditions	Yield
In methanol at 20℃; for 0.166667h;	96%

phosphoric acid di-tert-butyl ester (33494-81-4) + cobalt(II) diacetate tetrahydrate (6147-53-1) → [Co4(μ4-O)(di-tert-butyl phosphate)6]

Conditions	Yield
In tetrahydrofuran; methanol hot soln. of Co salt in MeOH added to THF soln. of ligand (molar ratio 1:1.5); stirred for ca. 12 h at room temp.; solvent removed in vac.; crystd. over 2 d on benchtop; elem. anal.;	93%

1,10-Phenanthroline (66-71-7) + phosphoric acid di-tert-butyl ester (33494-81-4) + water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) → C12H8N2[(C(CH3)3O)2PO2]2(H2O)Cu (642067-61-6)

Conditions	Yield
In methanol mixed in methanol, stirred for 5 min; evapd.(vac.), recrystd.(CH3CN/acetone 1:1), elem. anal.;	93%

phosphoric acid di-tert-butyl ester (33494-81-4) + triphenylbismuthane (603-33-8) → 2C6H5(1-)*Bi(3+)*C8H18O4P(1-)

Conditions	Yield
In ethanol at 20℃; for 24h; Reflux;	89.1%

chlorosulfuric acid chloromethyl ester (49715-04-0) + phosphoric acid di-tert-butyl ester (33494-81-4) → di-tert-butyl chloromethyl phosphate (229625-50-7)

Conditions	Yield
Stage #1: phosphoric acid di-tert-butyl ester With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In water for 0.166667h; Cooling with ice; Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; for 24h;	89%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;	72%
Stage #1: phosphoric acid di-tert-butyl ester With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.166667h; Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃;	72%

2,4,6-trimethyl-pyridine (108-75-8) + phosphoric acid di-tert-butyl ester (33494-81-4) + copper(II) acetate monohydrate (6046-93-1) → Cu(di-tert-butyl phosphate)2(2,4,6-trimethylpyridine)2 (658692-36-5)

Conditions	Yield
In acetonitrile adding solid di-tert-butyl phosphate, Cu salt, and 2,4,6-trimethylpyridine to acetonitrile, heating on a water bath until solid is dissolved; filtration, crystn. over 3 d; elem. anal.;	88%

phosphoric acid di-tert-butyl ester (33494-81-4) + tetramethyl ammoniumhydroxide (75-59-2) → tetramethylammonium di-tert-butyl hydrogen phosphate (34075-24-6)

Conditions	Yield
In water; acetone at 20℃; for 0.833333h; Cooling with ice;	87%
In acetone at 0℃;	57%
In water; acetone

phosphoric acid di-tert-butyl ester (33494-81-4) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → tetramethylammonium di-tert-butyl hydrogen phosphate (34075-24-6)

Conditions	Yield
In water; acetone for 0.5h;	87%

phosphoric acid di-tert-butyl ester (33494-81-4) + C23H27ClN2O9 → C31H45N2O13P

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In 1,4-dioxane Inert atmosphere;	87%

1H-imidazole (288-32-4) + phosphoric acid di-tert-butyl ester (33494-81-4) + nickel(II) acetate tetrahydrate (6018-89-9) → [Ni(di-tert-butyl phosphate)2(imidazole)4] (327056-82-6)

Conditions	Yield
In tetrahydrofuran; methanol soln. of Ni salt in MeOH added to soln. of 2 equiv. of phosphate in MeOHwith stirring; 4 equiv. of imidazole in THF added slowly along the wall s; crystd. over a few d; elem. anal.;	86%

1H-imidazole (288-32-4) + phosphoric acid di-tert-butyl ester (33494-81-4) + cobalt(II) diacetate tetrahydrate (6147-53-1) → [Co(di-tert-butyl phosphate)2(imidazole)4] (327056-80-4)

Conditions	Yield
In tetrahydrofuran; methanol soln. of Co salt in MeOH added to soln. of 2 equiv. of phosphate in MeOHwith stirring; 4 equiv. of imidazole in THF added slowly along the wall s; crystd. over a few d; elem. anal.;	85%

Upstream product

• 75-65-0 tert-butyl alcohol 
• 13086-84-5 di-tert-butyl phosphite 
• 90224-71-8 8-bromo-7-hydroxyquinoline 
• 117924-33-1 di-tert-butyl N,N-diethylphosphoramidite 
• 13086-84-5 di-tert-butyl phosphite 
• 7440-44-0 pyrographite 
• 33494-80-3 potassium di-tert-butylphosphate 

Downstream Products

• 229625-50-7 di-tert-butyl chloromethyl phosphate 
• 271250-91-0 (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-[[[m-di-t-butylphosphonooxymethyl]benzoyloxy]methoxy]butane 
• 68695-48-7 di-tert-butyl phosphoric acid tetra-n-butylammonium salt 
• 427899-56-7 bis-di-tert-butyl methyl phosphate 
• 1196960-32-3 (4-acetamidophenyl carbonic) (di-tert-butyl phosphoric)anhydride 
• 1431216-68-0 4-(5-{2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethylpropanamido}-4-(o-tolyl)pyridin-2-yl)-1-methyl-1-{[bis(tert-butoxy)phosphoryl]oxymethyl}piperazin-1-ium 
• 1367455-49-9 [2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4,5-difluorophenyl]methyl di-tert-butyl phosphate 
• 1421275-99-1 C₃₁H₃₄Br₂N₃O₈P 
• 1383139-19-2 Di-tert-butyl [2-{[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)acetyl]imino}-4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-3(2H)-yl]methyl phosphate 
• 1365173-24-5 phosphoric acid di-tert-butyl ester 2-cyano-8-[1-(3-trifluoromethylbenzyl)-1H-pyrazol-4-yl]-6-oxo-1-propyl-1,6-dihydropurin-9-ylmethyl ester 
• 1365173-21-2 phosphoric acid di-tert-butyl ester 2-cyano-6-oxo-1-propyl-8-[1-(3-trifluoromethylbenzyl)-1H-pyrazol-4-yl]-1,6-dihydropurin-7-ylmethyl ester 
• 1357576-98-7 di-tert-butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)-phenyl)piperidin-4-yl)methoxy)methyl phosphate 
• 1357576-21-6 (R)-4-(4-((4'-chlorobiphenyl-2-yl)(di-tert-butoxyphosphonooxymethoxy)methyl)piperidin-1-yl)benzoic acid 
• 1357577-02-6 di-tert-butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-((S)-3-((diethylamino)methyl)morpholino)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methoxy)methyl phosphate 

Relevant articles and documents

A extractant composition and its preparation method and application

The invention discloses an extractant composition as well as a preparation method and an application thereof. The composition comprises the following components in percentages by weight: a component A: 80-99.99wt% of dialkyl phosphinic acid with a structure shown in a formula I; a component B: 0-5wt% of dialkyl phosphinic acid with a structure shown in a formula II; a component C: 0-5wt% of dialkyl phosphinic acid alkyl ester with a structure shown in a formula III; a component D: 0-10wt% of alkyl phosphorous acid mono alkyl ester with a structure shown in a formula IV; wherein, the component B, C and D are not zero at the same time, and the sum of the component A, B, C and D is always 100wt%. The extractant composition containing synergistic extractant components is prepared, the composition is used as an extractant and can be widely applied to rare earth metals, especially separation and purification of cobalt nickel bimetals, and compared with monocomponent extraction agents, the composition has more excellent extraction performance; compared with bis (2,4,4-trimethylpentyl)-phosphinic acid, other synergistic extractant components are easy to synthesize, and production cost of the product is reduced.

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