4195-19-1

Basic information

• Product Name: 1-(TRIMETHYLACETYL)IMIDAZOLE 98
• Synonyms: 1-(TRIMETHYLACETYL)IMIDAZOLE 98;1-(2,2-Dimethyl-propionyl)-1H-imidazole;1-Pivaloyl-1H-imidazol;1-TRIMETHYLACETYL IMIDAZOLE 97%;1-(tert-Butoxycarbonyl)-1H-imidazole;1-(tert-Butyloxycarbonyl)-1H-imidazole;1H-Imidazole-1-carboxylic acid tert-butyl ester;1-(1H-imidazol-1-yl)-2,2-dimethylpropan-1-one
• CAS NO: 4195-19-1
• Molecular Formula: C₈H₁₂N₂O
• Molecular Weight: 152.19
• Product Categories: Imidazole;Heterocyclic Compounds;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Imidazoles
• Mol File: 4195-19-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 47-52 °C(lit.)
• Boiling Point: 245.7oC at 760 mmHg
• Flash Point: 214 °F
• Appearance: /
• Density: 1.02g/cm3
• Vapor Pressure: 0.0284mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 4.02±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1-(TRIMETHYLACETYL)IMIDAZOLE 98(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TRIMETHYLACETYL)IMIDAZOLE 98(4195-19-1)
• EPA Substance Registry System: 1-(TRIMETHYLACETYL)IMIDAZOLE 98(4195-19-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 4195-19-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

1-Pivaloyl-1H-imidazol (cas# 4195-19-1) is a compound useful in organic synthesis.

InChI:InChI=1/C8H12N2O/c1-8(2,3)7(11)10-5-4-9-6-10/h4-6H,1-3H3

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 75-98-9 Trimethylacetic acid 
• 18637-83-7 1,1'-oxalyldiimidazole 
• 288-32-4 1H-imidazole 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 81058-26-6 1,2,3,4,6-penta-O-trimethylacetyl-β-D-glucopyranose 
• 87791-17-1 1,2,4,6-Tetra-O-pivaloyl-β-D-glucopyranose 
• 143552-72-1 1,3,6-Tri-O-pivaloyl-β-D-glucopyranose 
• 143552-74-3 1,2,3,6-tetra-O-pivaloyl-β-D-glucopyranose 
• 118711-42-5 1,2,3,4,6-penta-O-pivaloyl-β-D-mannopyranose 
• 226877-02-7 1,2,3,6-tetra-O-pivaloyl-α-D-galactofuranose 
• 141110-74-9 (R)-2--3-ytimethylacetyl-1,2,3-propanetriol 1-p-toluenesulfonate 
• 141110-73-8 (R)-2-O-acetoxymethyl-3-O-p-toluenesulfonyl-1-O-trimethylacetyl-1,2,3-propanetriol 
• 141110-72-7 (R)-2-O-methoxymethyl-3-O-p-toluenesulfonyl-1-O-trimethylacetyl-1,2,3-propanetriol 

Relevant articles and documents

Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones

N-heterocyclic carbenes (NHCs) have emerged as catalysts for the construction of C?C bonds in the synthesis of substituted ketones under single-electron processes. Despite these recent reports, there still remains a need to increase the utility and practicality of these reactions by exploring new radical coupling partners. Herein, we report the synthesis of γ-aryloxyketones via combined NHC/photoredox catalysis. In this reaction, an α-aryloxymethyl radical is generated via oxidation of an aryloxymethyl potassium trifluoroborate salt, which is then added into styrene derivatives to provide a stabilized benzylic radical. Subsequent radical-radical coupling reaction with an azolium radical affords the γ-aryloxy ketone products. (Figure presented.).

Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

Two different ways to carry out the chemoselective acylation of 2-amino-8-quinolinol with unique features to generate C2-amides or C8-esters were developed. The coupling reaction with a variety of carboxylic acids using EDCI and DMAP provided C8-ester derivatives, whereas N-heteroaromatic acids were not introduced on the C8-hydroxy group, but rather on the C2-amino group under the same conditions. To obtain C2-amides selectively, the anionic nucleophile from 2-amino-8-quinolinol was treated with less reactive acyl imidazolides or esters.

Stability studies of N-acylimidazoles

Studies of the stabilities of a series of N-acylimidazoles towards acidic and basic conditions of potential usefulness for the removal of common temporary protection in peptide and oligonucleotide synthesis are presented. N-Acylimidazoles with a variety of substituents in the acyl component were prepared and treated with 3% trifluoroacetic acid (TFA) in chloroform and with 2% 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in N,N-dimethylformamide (DMF), the extent of their degradation being determined by proton NMR. N-(2,4,6-Trimethylbenzoyl)imidazole (1) and N-(2,6-dimethoxybenzoyl)-imidazole (2) remained unaffected under the above acidic and basic conditions after 4 d and 2 d, respectively. In addition, 1 and 2 were resistant to treatment with a solution of 2% piperidine/2% DBU in DMF for 24 h. Under ammonolytic conditions, 2 was rapidly cleaved (less than 1 h), whereas 1 was 64% degraded after 48 h, as ascertained by reversed-phase HPLC. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.