26690-80-2

Basic information

• Product Name: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE
• Synonyms: N-T-BUTOXYCARBONYL-2-AMINOETHANOL;N-T-BUTOXYCARBONYL-GLYCINOL;N-(TERT-BUTOXYCARBONYL)ETHANOLAMINE;N-(2-HYDROXYETHYL)CARBAMIC ACID TERT-BUTYL ESTER;N-(2-HYDROXYMETHYL)CARBAMIC ACID BENZYL ESTER;N-BOC-2-AMINOETHANOL;N-BOC-ETHANOLAMINE;N-BOC-AMINOETHANOL
• CAS NO: 26690-80-2
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.2
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous Natural Products;Amino Acids;Amino Alcohols;Boc-Amino acid series;Amines;Miscellaneous Reagents
• Mol File: 26690-80-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 92℃/0.22mm
• Flash Point: >230 °F
• Appearance: clear, light yellow/viscous liquid
• Density: 1.042 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 12.01±0.46(Predicted)
• Water Solubility: Soluble in water or 1% acetic acid. Soluble in ethyl acetate and methanol.
• BRN: 2353995
• CAS DataBase Reference: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE(26690-80-2)
• EPA Substance Registry System: TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE(26690-80-2)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41-36/37/38-23/24/25
• Safety Statements: 26-39-45-36/37/39-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 26690-80-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow clear liquid

Uses

Different sources of media describe the Uses of 26690-80-2 differently. You can refer to the following data:
1. suzuki reaction
2. Amine protected, difunctional reagent employed in the synthesis of phosphatidyl ethanolamines and ornithine.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 4185, 1987 DOI: 10.1016/S0040-4039(00)95574-6

InChI:InChI=1/C7H15NO3/c1-7(2,3)11-6(10)8-4-5-9/h9H,4-5H2,1-3H3,(H,8,10)

Upstream product

• 6627-89-0 tert-butyl phenyl carbonate 
• 141-43-5 ethanolamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Downstream Products

• 197641-33-1 (S)-2-[(2-tert-Butoxycarbonylamino-ethyl)-(toluene-4-sulfonyl)-amino]-propionic acid benzyl ester 
• 197641-34-2 (S)-2-[(2-tert-Butoxycarbonylamino-ethyl)-(toluene-4-sulfonyl)-amino]-3-methyl-butyric acid benzyl ester 
• 197641-32-0 (S)-2-[(2-tert-Butoxycarbonylamino-ethyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propionic acid benzyl ester 
• 198990-09-9 [2-(4-formyl-phenoxy)-ethyl]-carbamic acid tert-butyl ester 
• 271245-28-4 {2-[1-(4-chloro-phenyl)-2-iodo-1-methyl-ethoxy]-ethyl}-carbamic acid tert-butyl ester 
• 710327-29-0 ethyl (S)-3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-tert-butylphenoxy)propionate 
• 710326-96-8 ethyl 3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-phenoxypropionate 
• 845887-33-4 [4-(2-tert-butoxycarbonylamino-ethoxy)-2-nitro-phenoxy]-acetic acid methyl ester 
• 710326-99-1 ethyl 3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-fluorophenoxy)propionate 
• 710327-06-3 ethyl (S)-3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-methylphenoxy)propionate 
• 223127-65-9 ethyl 3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-methylphenoxy)propionate 
• 223127-81-9 ethyl 3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-chlorophenoxy)propionate 
• 223127-22-8 ethyl 3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-isopropylphenoxy)propionate 
• 710327-36-9 ethyl (S)-3-[4-(2-tert-butoxycarbonylaminoethoxy)phenyl]-2-(4-chlorophenoxy)propionate 

Relevant articles and documents

Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents

In a focused exploration, we designed, synthesized, and biologically evaluated chiral conjugated new chloroquine (CQ) analogues with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity (in vitro 50% inhibitory concentration, 56.98 nM for strain 3D7 and 97.76 nM for strain K1; selectivity index in vivo [up to at a dose of 12.5 mg/kg of body weight], 3,510) as a new lead antimalarial agent. Other compounds (compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c) also showed moderate activity against a CQ-sensitive strain (3D7) and superior activity against a CQ-resistant strain (K1) of Plasmodium falciparum. Furthermore, we carried out docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites of CQ analogues for incorporating steric, hydrophobic, and electropositive groups to improve the antimalarial activity.

Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).

Process for the preparation of acrylates

(Meth)acrylate esters containing an amine group blocked by a carbonate derivative having, e.g. t-butyl group, are made by reaction of a methyl or ethyl (meth)acrylate with a hydroxy carbamate derivative containing, e.g. a t-butyl group. The hydroxy carbamate derivative may be made by reacting an alkanolamine with an alkyl aryl carbonate in which the alkyl group is, e.g. t-butyl.