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Di-tert-butyl N,N-diisopropylphosphoramidite

Product Name
Di-tert-butyl N,N-diisopropylphosphoramidite
CAS No.
137348-86-8
Chemical Name
Di-tert-butyl N,N-diisopropylphosphoramidite
Synonyms
DI-TERT-BUTYL DIISOPROPYLPHOSPHORAMIDITE;N,N-diisopropylphosphoraMidite;DI-TERT-BUTYL-N,N-DIISOPROPYLPHOSPHORAMIDITE;13748-86-8;di-tert-butyl diisopropylphosphoramide;DIISOPROPYL DI-TERT-BUTYLPHOSPHORAMIDITE;DI-T-BUTYL N,N-DIISOPROPYLPHOSPHORAMIDITE;Di-tert-butoxy(diisopropylamino)phosphine;Di-tert-butyl diisopropylphosphoramidoite;Di-tert-butyl N,N-Diisopropylphosphoramidine
CBNumber
CB2747336
Molecular Formula
C14H32NO2P
Formula Weight
277.38
MOL File
137348-86-8.mol
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Di-tert-butyl N,N-diisopropylphosphoramidite Property

Boiling point:
85-90 °C/0.2 mmHg (lit.)
Density 
0.879 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.444(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
4.90±0.70(Predicted)
form 
Liquid
color 
Clear colorless
BRN 
4858847
Stability:
Moisture Sensitive
InChI
InChI=1S/C14H32NO2P/c1-11(2)15(12(3)4)18(16-13(5,6)7)17-14(8,9)10/h11-12H,1-10H3
InChIKey
YGFLCNPXEPDANQ-UHFFFAOYSA-N
SMILES
P(N(C(C)C)C(C)C)(OC(C)(C)C)OC(C)(C)C
CAS DataBase Reference
137348-86-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
F 
10-23
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
419362
Product name
Di-tert-butyl N,N-diisopropylphosphoramidite
Purity
95%
Packaging
1g
Price
$57.4
Updated
2025/07/31
Sigma-Aldrich
Product number
419362
Product name
Di-tert-butyl N,N-diisopropylphosphoramidite
Purity
95%
Packaging
5g
Price
$161
Updated
2025/07/31
TCI Chemical
Product number
D4211
Product name
Di-tert-butyl N,N-Diisopropylphosphoramidite
Purity
>98.0%(N)
Packaging
1g
Price
$44
Updated
2025/07/31
TCI Chemical
Product number
D4211
Product name
Di-tert-butyl N,N-Diisopropylphosphoramidite
Purity
>98.0%(N)
Packaging
5g
Price
$160
Updated
2025/07/31
TRC
Product number
D429400
Product name
Di-t-butylN,N-Diisopropylphosphoramidite
Packaging
50g
Price
$720
Updated
2021/12/16
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Di-tert-butyl N,N-diisopropylphosphoramidite Chemical Properties,Usage,Production

Chemical Properties

Clear Colourless Liquid

Uses

Di-tert-butyl N,N-diisopropylphosphoramidite is a general reagent to introduce tert-butyl-protected phosphate groups. It is commonly used in phosphorylation of biomolecules. It can also be used in the synthesis of phosphoramidate-linked glycoconjugates.

Uses

A phosphinane derivative with immunomodulating activity.

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

Synthesis

921-26-6

75-65-0

137348-86-8

General procedure for the synthesis of di-tert-butyl N,N-diisopropylphosphoramidite from dichloro-N,N-diisopropylphosphoramidite and tert-butyl alcohol: tert-butyl alcohol (3.7 g, 4.7 mL, 50 mmol, 2.0 eq.) and triethylamine (5.6 g, 7.7 mL, 55 mmol, 2.2 eq.) were prepared under anhydrous conditions by dissolving them in anhydrous ether (20 mL) as a solution. This solution was slowly added to a solution of dichloro-N,N-diisopropylphosphoramidite (5.0 g, 25 mmol) in anhydrous ethyl ether (5 mL) while keeping the reaction temperature below 0°C. The reaction temperature was kept below 0°C for a few minutes. After the addition was complete (about 15 minutes), the reaction mixture was slowly warmed to room temperature and stirring was continued for 3 hours. Upon completion of the reaction, the aqueous phase was separated by adding 5% aqueous sodium bicarbonate solution (10 mL) for quenching. The organic phase was washed sequentially with 5% aqueous sodium bicarbonate (2 x 10 mL) and saturated aqueous sodium chloride (25 mL), then dried over anhydrous sodium sulfate, filtered and concentrated to give a clarified oily residue. The target product, N,N-diisopropylphosphoramidite di-tert-butyl ester, was purified by vacuum distillation as a clear oil (4.3 g, 63% yield). The boiling point of the product was 56-57 °C (0.05 mmHg).1H-NMR (300 MHz, CDCl3) δ 1.17 (d, J = 6.0 Hz, CH(CH3)2), 1.35 (s, 18H, 2 × C(CH3)3), 3.53-3.68 (m, 2 × CH(CH3)2); 13C-NMR (125 MHz, CDCl3) δ 24.5 (s, 18H, 3.53-3.68 (m, 2 × CH(CH3)2)); and 13C-NMR (125 MHz, CDCl3) δ 24.0 (m, 2 × C(CH3)3). CDCl3) δ 24.21 (d, JPC = 7.73 Hz), 31.06 (d, JPC = 9.75 Hz), 43.09 (d, JPC = 13.88 Hz), 74.50 (d, JPC = 9.75 Hz); 31P-NMR (202 MHz, CDCl3) δ 130.0 (s).

References

[1] Patent: US7018987, 2006, B1. Location in patent: Page/Page column 9
[2] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 7, p. 1621 - 1628
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 164, p. 277 - 291

Di-tert-butyl N,N-diisopropylphosphoramidite Preparation Products And Raw materials

Raw materials

Preparation Products

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Di-tert-butyl N,N-diisopropylphosphoramidite Suppliers

Americas 1 Australia 1 Belgium 2 Canada 4 China 122 Europe 1 France 2 Germany 3 India 6 Japan 3 Switzerland 1 United Kingdom 9 United States 40 Global 195
Interchim SA
Tel
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Fax
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Email
him@interchim.com
Country
France
ProdList
2725
Advantage
58
Chemgo SARL
Tel
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Fax
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Email
sales.contact@chemgo.fr
Country
France
ProdList
488
Advantage
58
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View Lastest Price from Di-tert-butyl N,N-diisopropylphosphoramidite manufacturers

R&D Scientific Inc.
Product
Di-tert-butyl N,N-diisopropylphosphoramidite 137348-86-8
Price
US $2200.00/Kg
Min. Order
1Kg
Purity
97
Supply Ability
500 Kg
Release date
2024-07-11
Shaanxi Dideu Medichem Co. Ltd
Product
Di-tert-butyl N,N-diisopropylphosphoraMidite 137348-86-8
Price
US $1.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 tons
Release date
2020-01-16
Career Henan Chemical Co
Product
Di-tert-butyl N,N-diisopropylphosphoramidite 137348-86-8
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1
Release date
2018-08-06

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