137348-88-0

Usage

Uses

Used in Chemical Synthesis:
TERT-BUTYL TETRAISOPROPYLPHOSPHORODIAMIDITE is used as a reagent for the synthesis of aromatic oxophosphorus compounds through the Michaelis-Arbuzov type of reaction of arynes. This application is significant in the development of new compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TERT-BUTYL TETRAISOPROPYLPHOSPHORODIAMIDITE is used as a key intermediate in the synthesis of various drug molecules. Its ability to facilitate the Michaelis-Arbuzov type of reaction of arynes allows for the creation of novel compounds with potential therapeutic properties.
Used in Agrochemical Industry:
TERT-BUTYL TETRAISOPROPYLPHOSPHORODIAMIDITE is also utilized in the agrochemical industry for the synthesis of new compounds with pesticidal, herbicidal, or fungicidal properties. The reagent's role in the synthesis of aromatic oxophosphorus compounds contributes to the development of innovative and effective solutions for agricultural challenges.
Used in Materials Science:
In the field of materials science, TERT-BUTYL TETRAISOPROPYLPHOSPHORODIAMIDITE is employed in the synthesis of advanced materials with unique properties, such as improved thermal stability, mechanical strength, or electrical conductivity. The reagent's role in the Michaelis-Arbuzov type of reaction of arynes enables the creation of novel materials with potential applications in various industries, including electronics, aerospace, and automotive.

InChI:InChI=1/C16H37N2OP/c1-12(2)17(13(3)4)20(19-16(9,10)11)18(14(5)6)15(7)8/h12-15H,1-11H3

Synthetic route

bis(diisopropylamino)chlorophosphine (56183-63-2) + potassium tert-butylate (865-47-4) → [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0)

Conditions	Yield
In toluene at 20℃; for 24h; Schlenk technique; Inert atmosphere;	86%

Dichloro(tert-butoxy)phosphine (68905-25-9) + diisopropylamine (108-18-9) → [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0)

Conditions	Yield
In diethyl ether Ambient temperature;	78%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate → N,N,N',N'-tetraisopropyl phenylphosphonic diamide

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Reagent/catalyst; Temperature; Time; Concentration; Solvent;	100%

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4, 7738-22-9) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → tert-butyl O-(tert-butoxy(diisopropylamino)phosphanyl)-N-(tert-butoxycarbonyl)-L-serinate

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h; Inert atmosphere;	92%
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h;	92%
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h;	92%
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3.3h;	88%

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4, 7738-22-9) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → C23H46N2O6

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h;	92%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → 5'-O-(4,4'-dimethoxytrityl)thymidine 3'-O-[(tert-butyl)-N,N-diisopropylphosphoramidite]

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane at 20℃;	86%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + (R)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (71630-31-4) → C22H45N2O6P

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h; Inert atmosphere;	86%

tert-butyl 2-(tert-butoxycarbonylamino)-3-hydroxybutanoate + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → tert-butyl O-(tert-butoxy(diisopropylamino)phosphanyl)-N-(tert-butoxycarbonyl)-L-allothreoninate

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane; toluene at 20℃; for 3h; Inert atmosphere;	84%

(2S,3S)-2-amino-3-hydroxybutanoic acid (28954-12-3) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → tert-butyl O-(tert-butoxy(diisopropylamino)phosphanyl)-N-(tert-butoxycarbonyl)-L-allothreoninate

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h;	84%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl carbamate (185692-85-7) → C24H53N2O5PSi

Conditions	Yield
With 1H-tetrazole In dichloromethane; toluene at 20℃; for 3h; Inert atmosphere;	82%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → isourea

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 42h; Inert atmosphere;	81%

5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine (68892-41-1) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → 5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-2'-deoxyguanosine 3'-O-[(tert-butyl)-N,N-diisopropylphosphoramidite]

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane at 20℃;	79%

N-(tert-butoxycarbonyl)-L-serine methyl ester (2766-43-0) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → C19H39N2O6P

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane; toluene at 20℃; for 3h; Inert atmosphere;	79%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine 3'-O-[(tert-butyl)-N,N-diisopropylphosphoramidite]

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane at 20℃;	77%

pent-1-yn-5-ol (5390-04-5) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite (1243167-02-3)

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane at 20℃;	75%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → N,N,N',N'-tetraisopropyl phenylphosphonic diamide

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran at 0℃; for 1h; Reagent/catalyst; Temperature; Time; Concentration; Solvent;	71%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) → 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2'-deoxycytidine 3'-O-[(tert-butyl)-N,N-diisopropylphosphoramidite]

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane at 20℃;	65%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + tert-butyl alcohol (75-65-0) → di-tert-butyl diisopropylphosphoramide (137348-86-8)

Conditions	Yield
With N,N-diisopropylamine tetrazolide for 3h;	58%

tert-butyl (2S,3R)-2-amino-3-hydroxybutanoate (17083-30-6, 66748-90-1, 67580-85-2, 150693-46-2, 150693-47-3) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → isourea

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 5h;	44%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + tert-butyl D-allo-threonine → C23H47N2O6P

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 3h;	23%

2-iodophenyltrifluoromethanesulfonic acid (129112-26-1) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → N,N,N',N'-tetraisopropyl phenylphosphonic diamide

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 12h; Reagent/catalyst; Temperature; Time; Concentration; Solvent;	18%

6-nitroveratryl alcohol (1016-58-6) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → diisopropyl-phosphoramidous acid tert-butyl ester 4,5-dimethoxy-2-nitro-benzyl ester (603136-75-0)

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane at 0 - 20℃; for 16h;

4-hydroxy-2,5,2',4',6'-pentamethylbiphenyl (1042109-85-2) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → C33H57N2O2P

Conditions	Yield
With N,N-diisopropylamine tetrazolide In acetonitrile at 20℃; for 5h;

Z-Glu(Ser-OtBu)-OtBu (1493801-17-4) + [tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) → C35H60N3O9P

Conditions	Yield
With N,N-diisopropylamine tetrazolide In dichloromethane for 2h; Cooling with ice;

Upstream product

• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 865-47-4 potassium tert-butylate 
• 68905-25-9 Dichloro(tert-butoxy)phosphine 
• 108-18-9 diisopropylamine 

Downstream Products

• 137348-86-8 di-tert-butyl diisopropylphosphoramide 
• 603136-75-0 diisopropyl-phosphoramidous acid tert-butyl ester 4,5-dimethoxy-2-nitro-benzyl ester 

Relevant academic research and scientific papers

Palladium-catalysed amination of aryl- and heteroaryl halides using tert-butyl tetraisopropylphosphorodiamidite as an easily accessible and air-stable ligand

The phosphorus compound tert-butyl tetraisopropylphosphorodiamidite, prepared from bis(diisopropylamino)chlorophosphine, is an excellent ligand for palladium-catalysed Buchwald-Hartwig amination of aryl- and heteroaryl chlorides and bromides. Based on its ready accessibility and air-stability, this amination protocol is a practical approach to the synthesis of industrially important aryl- and heteroarylamines. Copyright

Alternative Strategies for the Fmoc Solid-Phase Synthesis of O4-Phospho-L-tyrosine-Containing Peptides

A number of biologically relevant O4-phospho-L-tyrosine-containing peptides have been synthesized by either the global phosphorylation of the side-chain-unprotected L-tyrosine moiety in presynthesized resin-bound peptides or alternatively by the incorporation of suitable protected O4-phospho-L-tyrosine building blocks in the continuous-flow method of Fmoc solid-phase peptide synthesis.Different phosphate-protecting groups have been applied.