39945-54-5 Usage
Description
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE, also known as N-tert-Butoxycarbonyl-3-bromopropylamine, is a versatile building block used in the synthesis of various pharmaceutical and biologically active compounds. It possesses unique chemical properties that make it a valuable intermediate in the development of new drugs and therapies.
Uses
Used in Pharmaceutical Industry:
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to be incorporated into complex molecular structures.
Used in Anti-HIV Applications:
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE is used as a building block in the synthesis of an active anti-HIV ethidium-arginine conjugate, which is specifically targeted against the viral TAR RNA sequence, playing a crucial role in the development of treatments for HIV.
Used in Synthesis of Biologically Active Compounds:
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE is used as a versatile component in the creation of biologically active compounds, contributing to the advancement of medicine and healthcare by enabling the development of new therapeutic agents.
Synthesis
Benzyl N-(3-bromopropyl)carbamate synthesis: A solution of triphenylphosphine (9.4 g, 28.60 mmol) and carbon tetrabromide (7.5 g, 28.60 mmol) in dry THF was added dropwise (30 mL) to a solution of benzyl N-(3-hydroxypropyl)carbamate (3.0 g, 14.30 mmol) in the same solvent (30 mL). After 48 h of stirring at room temperature, the solution was filtrated to remove an insoluble solid. After evaporation of filtrate, the residue was dissolved in CH2Cl2 and the solution washed with H2O. The organic layer was dried over MgSO4. Removal of the solvent yielded an oily residue, which was purified by column chromatography (CH2Cl2 to MeOH). After evaporation of the solvents benzyl N-(3-bromopropyl)carbamate was obtained as an orange oil (3.2 g, 86.4 %). Rf (silica-gel, CHCl3) = 0.5. 1H-NMR (300 MHz, CDCl3, ppm) δH 7.32 (5H, m, Cbz), 5.15 (1H, br s, CBzNH-), 5.06 (2H, s, Cbz), 3.39 (2H, t), 3.30 (2H, q), 2.06 – 1.96 (2H, m). 13C-NMR (75.5 MHz, CDCl3, ppm) δc 156.4, 136.3, 128.4, 128.0, 127.9, 66.6, 39.2, 32.3, 30.6.
Check Digit Verification of cas no
The CAS Registry Mumber 39945-54-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,9,4 and 5 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 39945-54:
(7*3)+(6*9)+(5*9)+(4*4)+(3*5)+(2*5)+(1*4)=165
165 % 10 = 5
So 39945-54-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H14BrNO2/c1-9(12)7-13-11(14)15-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,13,14)
39945-54-5Relevant articles and documents
A Nexus between Theory and Experiment: Non-Empirical Quantum Mechanical Computational Methodology Applied to Cucurbit[n]uril?Guest Binding Interactions
Hosta?, Ji?í,Sigwalt, David,?ekutor, Marina,Ajani, Haresh,Dubecky, Matú?,?ezá?, Jan,Zavalij, Peter Y.,Cao, Liping,Wohlschlager, Christian,Mlinari?-Majerski, Kata,Isaacs, Lyle,Glaser, Robert,Hobza, Pavel
, p. 17226 - 17238 (2016)
A training set of eleven X-ray structures determined for biomimetic complexes between cucurbit[n]uril (CB[7 or 8]) hosts and adamantane-/diamantane ammonium/aminium guests were studied with DFT-D3 quantum mechanical computational methods to afford ΔG
Discovery of naphthalimide conjugates as fluorescent probes for α1-adrenoceptors
Zhang, Wei,Zhou, Xin-Yang,Yu, Qin-Ying,Du, Lu-Pei,Li, Min-Yong
supporting information, p. 185 - 189 (2018/03/22)
α1-Adrenoceptors (α1-ARs), including at least three subtypes, α1A, α1B and α1D, which play essential roles in G protein-coupled receptors (GPCRs), can convey multiple pivotal extracellular signals in varied tissues and organs. In this research, a series of napthalimide-based small-molecule fluorescent probes (1a–1f) for α1-ARs, including two parts, a pharmacophore (quinazoline and phenylpiperazine) for α1-AR recognition and a fluorophore (naphthalimide) for visualization, were designed and synthesized successfully. These compounds display excellent fluorescence property and high affinity to receptors, which were used successfully for in vitro visualization of α1-adrenoceptors.
Halogenation of primary alcohols using a tetraethylammonium halide/[Et 2NSF2]BF4 combination
Pouliot, Marie-France,Mahe, Olivier,Hamel, Jean-Denys,Desroches, Justine,Paquin, Jean-Francois
supporting information, p. 5428 - 5431,4 (2020/10/15)
The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et2NSF2]BF4 (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.
