100134-82-5

Basic information

• Product Name: BENZYL [1-CYANO-1-METHYLETHYL]CARBAMATE
• Synonyms: BENZYL [1-CYANO-1-METHYLETHYL]CARBAMATE;Raltegravir I;Benzyl N-(1-cyano-1-methylethyl)carbamate;Raltegravir Intermediate 1;benzyl 2-cyanopropan-2-ylcarbaMate;N-(1-cyano-1-methylethyl)-, phenylmethyl ester;Benzyl (1-cyano-1-methylethyl)
• CAS NO: 100134-82-5
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 100134-82-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 381.613 °C at 760 mmHg
• Flash Point: 184.593 °C
• Appearance: Colourless solid
• Density: 1.125 g/cm³
• Refractive Index: 1.526
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• PKA: 9.59±0.46(Predicted)
• Water Solubility: 70g/L
• CAS DataBase Reference: BENZYL [1-CYANO-1-METHYLETHYL]CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL [1-CYANO-1-METHYLETHYL]CARBAMATE(100134-82-5)
• EPA Substance Registry System: BENZYL [1-CYANO-1-METHYLETHYL]CARBAMATE(100134-82-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 100134-82-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Solid

Uses

An intermediate in the preparation of HIV-integrase inhibitors

InChI:InChI=1/C12H14N2O2/c1-12(2,9-13)14-11(15)16-8-10-6-4-3-5-7-10/h3-7H,8H2,1-2H3,(H,14,15)

Upstream product

• 15030-72-5 Z-Aib-OH 
• 81587-18-0 benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate 
• 501-53-1 benzyl chloroformate 
• 50846-36-1 2-amino-2-methylpropanenitrile monohydrochloride 
• 19355-69-2 2-amino-2-cyanopropane 

Downstream Products

• 857664-99-4 methyl 5-(benzoyloxy)-2-(2-(benzyloxycarbonylamino)propan-2-yl)-6-methoxypyrimidine-4-carboxylate 
• 518048-01-6 methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate 
• 518048-00-5 methyl 5-(benzoyloxy)-2-(2-(benzyloxycarbonylamino)propan-2-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate 
• 850203-57-5 benzyl (1-amino-2-methylpropan-2-yl)carbamate 
• 1415000-09-7 C₂₄H₂₆N₄O₆ 
• 1415000-08-6 C₂₄H₂₃F₃N₄O₅ 
• 1415000-07-5 C₂₄H₂₆N₄O₅ 
• 1415000-06-4 C₂₃H₂₃ClN₄O₅ 
• 1415000-05-3 C₂₃H₂₄N₄O₅ 
• 1415000-21-3 C₂₄H₂₇N₅O₆ 
• 1415000-20-2 C₂₃H₂₄FN₅O₅ 
• 1415000-19-9 C₁₆H₁₆N₄O₅ 
• 1415000-18-8 C₂₃H₂₂FN₅O₅ 
• 1415000-17-7 C₁₆H₁₉N₅O₅ 

Relevant articles and documents

A Scalable Synthesis of 2-(1,2,4-Oxadiazol-3-yl)propan-2-amine Hydrobromide Using a Process Safety-Driven Protecting Group Strategy

A safe and scalable synthesis of 2-(1,2,4-oxadiazol-3-yl)propan-2-amine hydrobromide is described. A process safety-driven synthetic strategy was employed for the selection of thermally stable compounds en route to the target 1,2,4-oxadiazole. Application

The Synthesis of Ketone-Derived Enamides by Elimination of HCN from Cyanoamides

Treatment of easily available ketone-derived cyanoamides with NaOtBu leads to enamides in a simple, scalable, and inexpensive one-step operation in good yield. Enamides not stabilized by conjugation or by inclusion in a ring can also be prepared. An E1cB mechanism consistent with all results and observations, is proposed. The Z geometry of the product enamide is highly favoured, and the regioselectivity can be directed by one′s choice of protecting group.

Structural modifications of 5,6-dihydroxypyrimidines with anti-HIV activity

A series of 5,6-dihydroxypyrimidine analogs were synthesized and evaluated for their anti-HIV activity in vitro. Among all of the analogs, several compounds exhibited significant anti-HIV activity, especially 1b and 1e, which showed the most potent anti-HIV activity with EC50 values of 0.14 and 0.15 μM, and TI (therapeutic index) values of >300 and >900, respectively. Further docking studies revealed that the representative compounds 1e and 3a could meet the HIV-1 integrase inhibition minimal requirements of a chelating domain (two metal ions) and an aromatic domain (π-π stacking interactions).