23838-12-2

Basic information

• Product Name: Cholesteryl 4-nitrobenzoate
• Synonyms: Cholest-5-en-3beta-yl p-nitrobenzoate;CHOLESTERYL P-NITROBENZOATE;cholesteryl 4-nitrobenzoate;[10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 4-nitrobenzoate;5-CHOLESTEN-3BETA-OL 3-P-NITROBENZOATE;4-nitrobenzoate;Cholest-5-en-3-ol(3β)-,4-nitrobenzoate;CHOLESTERYL 3,5-DINITROBENZOATE
• CAS NO: 23838-12-2
• Molecular Formula: C₃₄H₄₉NO₄
• Molecular Weight: 535.76
• EINECS: 245-901-1
• Mol File: 23838-12-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 619.2 °C at 760 mmHg
• Flash Point: 190.6 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 2.94E-15mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: Cholesteryl 4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Cholesteryl 4-nitrobenzoate(23838-12-2)
• EPA Substance Registry System: Cholesteryl 4-nitrobenzoate(23838-12-2)

Safety Data

• Hazardous Substances Data: 23838-12-2(Hazardous Substances Data)

Usage

General Description

Cholesteryl 4-nitrobenzoate is a chemical compound that belongs to the family of cholesteryl esters, which are cholesterol derivatives containing an ester functional group. The specific chemical structure of cholesteryl 4-nitrobenzoate includes a cholesterol molecule attached to a 4-nitrobenzoate group through an ester bond. Cholesteryl 4-nitrobenzoate has been studied for its potential applications in liquid crystal displays and other optoelectronic devices due to its ability to form liquid crystalline phases. Additionally, cholesteryl 4-nitrobenzoate has been investigated for its potential use as a precursor in the synthesis of other functional materials and as a model compound for studying the behavior of cholesterol derivatives in biological and industrial systems.

InChI:InChI=1/C34H49NO4/c1-22(2)7-6-8-23(3)29-15-16-30-28-14-11-25-21-27(17-19-33(25,4)31(28)18-20-34(29,30)5)39-32(36)24-9-12-26(13-10-24)35(37)38/h9-13,22-23,27-31H,6-8,14-21H2,1-5H3

Upstream product

• 57-88-5 cholesterol 
• 619-80-7 4-nitrobenzamide 
• 122-04-3 4-nitro-benzoyl chloride 
• 57-88-5 cholesterol 

Downstream Products

• 22575-25-3 3-cholesteryl p-aminobenzoate 
• 59857-03-3 cholesterol p-fluorobenzoate 
• 132042-72-9 3-cholesteryl p-formamidobenzoate 
• 131809-14-8 3-cholesteryl p-isocyanobenzoate 

Relevant articles and documents

Desorption Chemical Ionization Mass Spectrometry of Epimeric 3-Hydroxysteroids and Derivatives. Stereoselectivity and Nucleophilic Substitution with Ammonia

The desorption chemical ionization mass spectra, using ammonia as reagent gas, of several epimeric 3-hydroxysteroids and their ether and carboxylic acid ester derivatives are reported.In the case of steroids possessing a Δ4- or Δ5-3α-benzoate moiety, stereospecific stabilization of the protonated molecular ion + is observed.This behaviour is rationalized in terms of interaction of the double bond and the protonated benzoate group at C-3.Nucleophilic substitution by NH3 is observed when a double bond is present in the vicinity of the substitution center.The nature and the stereochemistry of the leaving group influence this substitution reaction.Our results seem to indicate the operation of a two-step mechanism (e.g.SN1 type reaction) rather than a SN2 type mechanism for the formation of the substitution ion +.

Cross-linked liquid crystalline polybenzoxazines bearing cholesterol-based mesogen side groups

A cross-linked liquid crystalline polybenzoxazine [poly(BA-ac)] was synthesized for the first time from a novel bifunctional benzoxazine monomer (BA-ac) containing cholesterol-based mesogens. The monomer was synthesized using cholesteryl 4-aminobenzoate, bisphenol-A, and paraformaldehyde as raw materials via Mannich reaction. Subsequently, the cross-linked polybenzoxazine bearing cholesterol-based mesogen side groups was obtained through thermally induced ring-opening polymerization of the benzoxazine ring. The study results show that BA-ac is a monotropic smectic C liquid crystal, and poly(BA-ac) contains a smectic C phase structure. The formation of the liquid crystalline structure of poly(BA-ac) is mainly caused by the strong ability of cholesterol-based mesogen to form liquid crystals and its position on the side group of the cross-linked network. Due to the existence of a liquid crystal structure, poly(BA-ac) has high thermal conductivity. Its coefficient of thermal diffusivity is 31% higher than that of a traditional polybenzoxazine poly(BA-a). Poly(BA-ac) also has high heat-resistance. Its glass transition temperature, 5% and 10% weight loss temperatures are 175 °C, 306 °C, and 321 °C, respectively.

A liquid-crystalline poly(iminomethylene) with cholesterol-containing pendant groups

Two poly(iminomethylenes) with cholesterol-containing pendant groups were synthesized.Using an aliphatic spacer, a liquid-crystalline polymer was obtained, with equal amounts of right- and left-handed helices.With phenylene as bridging group, only oligomers resulted, probably for steric reasons.Some novel liquid-crystalline esters of cholesterol are also presented.