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

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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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13748-86-8

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137348-86-8

13748-86-8

C14H32NO2P

CH32CH2NPOCCH332

Catalysis and Inorganic Chemistry

Phosphorus Compounds

Phosphine Ligands

Phosphorylating and Phosphitylating Agents

Catalysis and Inorganic Chemistry

Phosphine Ligands

Phosphorus Compounds

Phospholipids - 13C & 2H