145878-50-8

Basic information

• Product Name: Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI);N-Boc-3-aminobenzonitrile;tert-Butyl N-(3-cyanophenyl)carbamate
• CAS NO: 145878-50-8
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25176
• Product Categories: N-BOC
• Mol File: 145878-50-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 125-130°C
• Boiling Point: 286.6±23.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• PKA: 13.08±0.70(Predicted)
• CAS DataBase Reference: Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI)(145878-50-8)
• EPA Substance Registry System: Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI)(145878-50-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 145878-50-8(Hazardous Substances Data)

Usage

General Description

Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI) is a chemical compound with the molecular formula C12H14N2O2. It is also known as t-butyl (3-cyanophenyl)carbamate. Carbamic acid, (3-cyanophenyl)-, 1,1-dimethylethyl ester (9CI) is a derivative of carbamic acid and is commonly used in organic synthesis and as a precursor in the production of pharmaceuticals and agrochemicals. It is a colorless to pale yellow liquid that is not very soluble in water but is soluble in organic solvents. The compound is considered to be of low toxicity, but proper safety precautions should be taken when handling it.

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 6952-59-6 3-cyanobromobenzene 
• 18437-67-7 1,1-dimethylethyl (3-methylphenyl)carbamate 
• 766-84-7 3-chloro-benzonitrile 
• 917-61-3 sodium isocyanate 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2237-30-1 m-cyanoaniline 

Downstream Products

• 145899-46-3 [3-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-carbamic acid tert-butyl ester 
• 503469-36-1 3-(3-aminophenyl)-1,2,4-oxadiazol-5(4H)-one 

Relevant articles and documents

N-Arylation of Carbamates through Photosensitized Nickel Catalysis

A highly efficient method of visible light mediated Ni(II)-catalyzed photoredox N-arylation of Cbz-amines/Boc-amines with aryl electrophiles at room temperature is reported. The methodology provides a common access to a wide variety of N-aromatic and N-heteroaromatic carbamate products that find use in the synthesis of several biologically active molecules and provides a distinct advantage over traditional palladium-catalyzed Buchwald reaction.

Palladium-catalyzed synthesis of N-aryl carbamates

An efficient synthesis of aryl carbamates was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of ArX (X = Cl, OTf) with sodium cyanate. The use of aryl triflates as electrophilic components in this transformation a

Design of pentapeptidic BACE1 inhibitors with carboxylic acid bioisosteres at P1′ and P4 positions

We previously reported potent BACE1 inhibitors KMI-420 and KMI-570 possessing a hydroxymethylcarbonyl isostere as a substrate transition-state mimic. Acidic moieties at the P1′ and P4 positions of KMI inhibitors are thought to be unfavorable in terms of membrane permeability across the blood-brain barrier. Herein, we replaced acidic moieties at the P4 position with hydrogen bond accepting groups and acidic moieties at the P1′ position with less acidic and similar molecular-size moieties (carboxylic acid or tetrazole bioisosteres). These inhibitors exhibited improved BACE1 inhibitory activities and a thorough quantitative structure-activity relationship study was performed.