137348-86-8

Basic information

• Product Name: Di-tert-butyl N,N-diisopropylphosphoramidite
• Synonyms: DI-T-BUTYL N,N-DIISOPROPYLPHOSPHORAMIDITE;DI-TERT-BUTYL DIISOPROPYLPHOSPHORAMIDITE;DI-TERT-BUTYL-N,N-DIISOPROPYLPHOSPHORAMIDITE;DI-TERT-BUTYL-N,N-DIISOPROPYLPHOSPHOROAMIDITE;N,N-Bis(1-methylethyl)phosphoramidous Acid Bis(1,1-dimethylethyl)ester;N,N-BisisopropylphosphoraMidous acid bis(tert-butyl) ester;N,N-diisopropylphosphoraMidite;Di-tert-butyl N,N-diisopropylphosphoraMidite 95%
• CAS NO: 137348-86-8
• Molecular Formula: C₁₄H₃₂NO₂P
• Molecular Weight: 277.38
• Product Categories: Phospholipids - 13C & 2H;Phosphorylating and Phosphitylating Agents;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds
• Mol File: 137348-86-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 85-90 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 0.879 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0195mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.90±0.70(Predicted)
• Stability: Moisture Sensitive
• BRN: 4858847
• CAS DataBase Reference: Di-tert-butyl N,N-diisopropylphosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: Di-tert-butyl N,N-diisopropylphosphoramidite(137348-86-8)
• EPA Substance Registry System: Di-tert-butyl N,N-diisopropylphosphoramidite(137348-86-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 137348-86-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear Colourless Liquid

Uses

Different sources of media describe the Uses of 137348-86-8 differently. You can refer to the following data:
1. 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.
2. A phosphinane derivative with immunomodulating activity.

InChI:InChI=1/C14H32NO2P/c1-11(2)15(12(3)4)18(16-13(5,6)7)17-14(8,9)10/h11-12H,1-10H3

Upstream product

• 108-18-9 diisopropylamine 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 75-65-0 tert-butyl alcohol 
• 137348-88-0 [tert-butyloxy]bis(N,N-diisopropylamino)phosphane 

Downstream Products

• 1056967-34-0 C₂₁H₃₆NO₆P 
• 956037-83-5 C₃₅H₄₃FNO₆P 
• 956037-74-4 4-[2-(4'-bromo-2'-fluorobiphenyl-4-yl)ethyl]-4-(di-tert-butylphosphoryloxymethyl)-2-methyl-2-oxazoline 
• 956037-78-8 4-(di-tert-butylphosphoryloxymethyl)-4-[2-(2'-fluoro-4'-(4-methylphenoxy)biphenyl-4-yl)ethyl]-2-methyl-2-oxazoline 
• 448959-96-4 C₂₈H₄₉N₂O₇P 
• 851511-83-6 C₃₂H₅₉N₂O₆P 
• 654067-55-7 {2-(di-tert-butoxy-thiophosphoryloxy)-1-methyl-1-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester 
• 654067-54-6 {2-(di-tert-butoxy-phosphoryloxy)-1-methyl-1-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester 
• 448960-04-1 C₃₀H₅₃N₂O₇P 
• 448959-60-2 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester 
• 942399-34-0 2-acetamido-2-di(tert-butyl)phosphoryloxymethyl-4-(4-heptyloxy-3-trifluoromethylphenyl)butyl acetate 
• 942399-68-0 [1-di(t-butyl)phosphoryloxymethyl-1-ethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)propyl]carbamic acid t-butyl ester 
• 942399-63-5 (S)-[1-di(t-butyl)phosphoryloxymethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)-1-methylpropyl]carbamic acid t-butyl ester 
• 942399-58-8 [1-di(t-butyl)phosphoryloxymethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)-1-methylpropyl]carbamic acid t-butyl ester 

Relevant articles and documents

Synthesis of combretastatin A-4 prodrugs and trans-isomers thereof

The present invention relates to novel water-soluble, stable derivatives of combretastatin A-4, and novel synthesis methods therefore. The combretastatin A-4 prodrugs described herein appear to be useful in the treatment of neoplastic disease.

Kinetics and mechanism of tetrazole-catalyzed phosphoramidite alcoholysis

Kinetics of the tetrazole-catalyzed reaction of diisopropyl N,N-diisopropylphosphoramidite (1b) with tert-butyl alcohol has been studied by 31P NMR spectroscopy in THF, and the results obtained have been compared to those observed for the possible partial reactions involved, viz. the formation of diisopropyl tetrazolylphosphite (2b) and its subsequent alcoholysis. The stoichiometry of the processes was first examined with dimethyl N,N-diisopropylphosphoramidite (1a) in MeCN. The tetrazole-promoted disappearance of 1b is as fast in the absence and in the presence of the alcohol: the alcoholysis of 1b is zero-order in the concentration of alcohol and second-order in the concentration of tetrazole. The reaction of 1b with tetrazole is independent of the concentration of the tetrazolide anion and second-order in that of tetrazole, while the reverse reaction, aminolysis of 2b is first-order in the concentration of the amine The alcoholysis of 2b is, in turn, first-order in the concentration of alcohol and second-order in that of tetrazole, but it also proceeds, although slowly, in the absence of tetrazole. The time-dependent product distribution of the alcoholysis of 1b shows intermediary accumulation of 2b, but at a lower level than could be predicted by applying the rate constants determined independently for the assumed partial reactions. Accordingly, tetrazole-catalyzed alcoholysis of 1b is shown to proceed at least mainly via 2b, but an additional pathway not involving 2b as an intermediate is proposed. Mechanisms of the partial reactions are discussed on the basis of the formal kinetics observed.