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

Description

Di-tert-butyl N,N-diisopropylphosphoramidite is a phosphinane derivative that exists as a clear, colorless liquid. It is a versatile reagent known for its ability to introduce tert-butyl-protected phosphate groups, making it a valuable compound in various chemical and biological applications.

Uses

Used in Chemical Synthesis:
Di-tert-butyl N,N-diisopropylphosphoramidite is used as a general reagent for the phosphorylation of biomolecules, which is crucial in the development of various pharmaceuticals and bioactive compounds. Its ability to protect phosphate groups allows for greater control and specificity in chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Di-tert-butyl N,N-diisopropylphosphoramidite is used as a key intermediate in the synthesis of phosphoramidate-linked glycoconjugates. These glycoconjugates have potential applications in drug delivery systems, enhancing the targeting and efficacy of therapeutic agents.
Used in Immunomodulation:
Di-tert-butyl N,N-diisopropylphosphoramidite also exhibits immunomodulating activity, making it a valuable compound in the development of treatments for various immune-related disorders. Its immunomodulatory properties can be harnessed to regulate immune responses and potentially improve patient outcomes in various medical conditions.

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

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

Downstream Products

• 876391-73-0 phosphoric acid di-tert-butyl ester 4-[2-(4-octyl-phenyl)-ethyl]-2-trichloromethyl-4,5-dihydro-oxazol-4-ylmethyl ester 
• 1056967-34-0 C₂₁H₃₆NO₆P 
• 145545-15-9 3'-O-bis(tert-butyl)phosphorylcombretastatin 
• 135544-65-9 N²-<<(9H-Fluoren-9-yl)methoxy>carbonyl>-O⁴--L-tyrosine 
• 942399-58-8 [1-di(t-butyl)phosphoryloxymethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)-1-methylpropyl]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 
• 942399-68-0 [1-di(t-butyl)phosphoryloxymethyl-1-ethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)propyl]carbamic acid t-butyl ester 
• 942399-34-0 2-acetamido-2-di(tert-butyl)phosphoryloxymethyl-4-(4-heptyloxy-3-trifluoromethylphenyl)butyl acetate 

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.