4351-55-7

Basic information

• Product Name: Cholesteryl formate
• Synonyms: (3β)-cholest-5-en-3-ylmethanoate;Cholest-5-en-3-ol (3beta)-, formate;cholest-5-en-3-ol(3β)-,formate;Cholest-5-en-3-yl formate;5-CHOLESTEN-3BETA-OL 3-FORMATE;5-CHOLESTEN-3-BETA-OL FORMATE;3-BETA-HYDROXY-5-CHOLESTENE 3-FORMATE;CHOLESTEROL FORMATE
• CAS NO: 4351-55-7
• Molecular Formula: C₂₈H₄₆O₂
• Molecular Weight: 414.66
• EINECS: 224-416-9
• Product Categories: Cholesteryl Compounds (Liquid Crystals);Functional Materials;Liquid Crystals & Related Compounds;Steroids
• Mol File: 4351-55-7.mol

Chemical Properties

• Melting Point: 95 °C
• Boiling Point: 487.1°Cat760mmHg
• Flash Point: 206.2°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 1.22E-09mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: Cholesteryl formate(CAS DataBase Reference)
• NIST Chemistry Reference: Cholesteryl formate(4351-55-7)
• EPA Substance Registry System: Cholesteryl formate(4351-55-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 4351-55-7(Hazardous Substances Data)

Usage

Uses

Used in Liquid Crystal Production:
Cholesteryl formate is used as a key component in the production of liquid crystals, which are materials that exhibit properties between those of conventional liquids and solid crystals. These liquid crystals can exist in various phases, including solid, smectic, and nematic, making them valuable for various applications in the field of display technology and other industries. The unique properties of cholesteryl formate contribute to the formation and stability of these liquid crystal phases.

InChI:InChI=1/C28H46O2/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(30-18-29)13-15-27(21,4)26(23)14-16-28(24,25)5/h9,18-20,22-26H,6-8,10-17H2,1-5H3

Upstream product

• 57-88-5 cholesterol 
• 3724-43-4 Vilsmeier reagent 
• 68-12-2 N,N-dimethyl-formamide 
• 57-88-5 cholesterol 
• 42126-00-1 3-Methoxypropen-2-yl-formiat 
• 18197-22-3 N-formylformamide 
• 110-82-7 cyclohexane 
• 85135-66-6 (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-diazoacetate 
• 98-88-4 benzoyl chloride 
• 534-17-8 caesium carbonate 
• 75-87-6 chloral 
• 64-18-6 formic acid 
• 57711-50-9 3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene 
• 3397-76-0 N,N-Dimethylformamide Hydrochloride 

Downstream Products

• 1460-02-2 1,3,5-Tri-tert-butylbenzene 
• 3975-81-3 2,4,6-tri(tert-butyl)benzaldehyde 

Relevant articles and documents

β-oxopropyl formate as a formylating agent of sterols

Propargylic alcohol reacts with formic acid in the presence of mononuclear catalysts of ruthenium to selectively afford β-oxopropyl formate which has been shown as an excellent mild formylating agent of sterols when the reaction is catalyzed by 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

Reaction of C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 with the two Vilsmeier-Haack complexes POCl3·DMF and (CF3SO2)2O·DMF: An efficient one-step conversion to the

The two electrophilic Vilsmeier-Haack complexes POCl3·DMF 1 and (CF3SO2)2O·DMF 2 react with C2-symmetrical dialkoxysilanes R1O-Si(R2)2-OR1 (R1=(-)-menthyl o

DMF·HCl as a versatile and straightforward N- and O-formylating agent

Inspired by the serendipitous isolation of N-formylpiperazines when we attempted the synthesis of a series of piperazines, we have developed a straightforward methodology for the N- and O- formylation of secondary cyclic amines, anilines and steroids, respectively. Such approach is based on the hitherto non-reported use of DMF·HCl complex, as a versatile and easily-available formylating system that can be stored without apparent loss of activity.

Polyvinylpolypyrrolidoniume tribromide as new and metal-free catalyst for the formylation and trimethylsilylation of hydroxyl group

Trimethylsilylation of alcohols was achieved using 1,1,1,3,3,3- hexamethyldisilazane (HMDS) as silylating agent, in the presence of polyvinylpolypyrrolidoniume tribromide in acetonitrile at room temperature. Also a variety of alcohols were converted into alkyl formates by ethyl formate and a catalytic amount of polyvinylpolypyrrolidoniume tribromide under solvent free conditions at room temperature.

Highly efficient formylation of alcohols, thiols and aniline derivatives by a heterogeneous (HCOOH/SiO2) system under microwave irradiation and solvent-free conditions

A simple, rapid and efficient microwave-assisted procedure for the formylation of aniline derivatives and alcohols, using a heterogeneous (HCOOH/SiO2) system under solvent-free conditions is reported. The method is applied to a set of amines, alcohols and thiols and short reaction times (10 min) with high yields are reported. This protocol introduces a practical and viable green technology of solvent-free and catalyst-free reactions.

Silica sulfuric acid and AI(HSO4)3: As efficient catalysts for the formylation of alcohols by using ethyl formate under heterogeneous conditions

A mixture of ethyl formate and a catalytic amount of silica sulfuric acid or Al(HSO4)3 as suitable formylating systems can formylate various alcohols to their corresponding formate ester derivatives under mild, nearly neutral and heterogeneous conditions at room temperature with good to excellent yields.

A simple, convenient and chemoselective formylation of sterols by Vilsmeier reagent

Vilsmeier reagent (DMF-POCl3) was used as an efficient formylating agent. Several sterols having sec-hydroxyl group at 3/17-position have been modified into respective formate esters. The method is simple, mild, chemoselective and provides sec-alcoholic protection in good yields.

Conversion of alkyl halides into alcohols via formyloxylation reaction with DMF catalyzed by silver salts

The transformation of alkyl halides into alcohols via a two-step process based on the reaction with DMF catalyzed by Ag(I) salts followed by acid or basic hydrolysis of the intermediate formate ester has been evaluated. The results show that a large variety of primary and some secondary alkyl halides can be transformed efficiently into the corresponding alcohols, making this alkyl halide to alcohol interconversion a valuable alternative to the existing procedures, particularly in molecules with labile functional groups that are generally involved in multistep synthesis. Georg Thieme Verlag Stuttgart.

Silphos [PCl3-n(SiO2)n]: A heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate

Alcohols and amines are formylated and acetylated in the presence of Silphos [PCl3-n(SiO2)n] in ethyl formate and ethyl acetate in high to excellent yields. This procedure provides a method to separate the product by a simple filtration.

Vilsmeier-Haack Reagents. Novel Electrophiles for the One-Step Formylation of O-Silylated Ethers to O-Formates

Various O-silylated substrates were effectively converted in one-step to their corresponding O-formates using electrophilic racemic and homochiral Vilsmeier-Haack reagents. Reactivity trends of these transformations were examined that, specifically, empha