5399-02-0

Basic information

• Product Name: N-HEPTADECANONITRILE
• Synonyms: heptadecanoicacidnitrile;Heptadecanonitrile;Hexadecyl cyanide;N-HEXADECYL CYANIDE;N-HEPTADECANONITRILE;1-CYANOHEXADECANE;HEPTADECANENITRILE;CETYL CYANIDE
• CAS NO: 5399-02-0
• Molecular Formula: C₁₇H₃₃N
• Molecular Weight: 251.45
• EINECS: 226-432-1
• Product Categories: C10 to C27;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 5399-02-0.mol

Chemical Properties

• Melting Point: 34°C
• Boiling Point: 208 °C / 10mmHg
• Flash Point: 137.5°C
• Appearance: /
• Density: 0.8315
• Vapor Pressure: 5.93E-05mmHg at 25°C
• Refractive Index: 1.4467
• BRN: 1775016
• CAS DataBase Reference: N-HEPTADECANONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: N-HEPTADECANONITRILE(5399-02-0)
• EPA Substance Registry System: N-HEPTADECANONITRILE(5399-02-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• WGK Germany: 3
• Hazardous Substances Data: 5399-02-0(Hazardous Substances Data)

Usage

Uses

Used in Surface Science and Materials Engineering:
N-HEPTADECANONITRILE is used as an adsorbent for gold and copper surfaces from hexane or acetone solutions. The application reason is its ability to form stable adsorbed layers on these metal surfaces, which can be studied using reflection infrared spectroscopy. This property is valuable for understanding the interactions between organic compounds and metal surfaces, as well as for developing new materials and coatings with specific properties.
Used in Analytical Chemistry:
N-HEPTADECANONITRILE is used as a reference compound in reflection infrared spectroscopy. The application reason is its distinct spectral features, which can be used to calibrate and validate the spectroscopic techniques employed in the study of adsorbed layers on metal surfaces. This helps improve the accuracy and reliability of the analytical results obtained from these studies.
Used in Nanotechnology and Materials Research:
N-HEPTADECANONITRILE can be used as a template or additive in the synthesis of nanoparticles and other nanostructured materials. The application reason is its ability to interact with metal surfaces, which can influence the growth and assembly of nanoparticles during their synthesis. This property can be exploited to develop novel materials with tailored properties and applications in various fields, such as electronics, energy storage, and catalysis.

Synthesis Reference(s)

Synthetic Communications, 6, p. 21, 1976 DOI: 10.1080/00397917608062128

InChI:InChI=1/C17H33N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18/h2-16H2,1H3

Upstream product

• 544-77-4 1-iodohexadecane 
• 151-50-8 potassium cyanide 
• 506-12-7 heptadecanoic acid 
• 4860-03-1 1-Chlorohexadecan 
• 58587-19-2 1-(2-tetrahydropyranyloxy)hexadecane 
• 143-33-9 sodium cyanide 
• 112-82-3 hexadecanyl bromide 
• 85577-46-4 S,S-diethyl-S-3-<(hexadecyloxy)sulfonyl>propylsulfonium ethylsulfate 
• 85577-55-5 S,S-diethyl-S-3-<(hexadecyloxy)sulfonyl>propylsulfonium camphor-10-sulfonate 
• 85577-54-4 S,S-diethyl-S-3-<(hexadecyloxy)sulfonyl>propylsulfonium picrate 
• 66278-78-2 C₂₂H₄₈NO₃S⁽¹⁺⁾*CN^(1-) 
• 36653-82-4 1-Hexadecanol 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 83634-89-3 hexadecyl 3-(dimethylamino)propanesulfonate 

Downstream Products

• 22986-69-2 17-tritriacontanone 
• 19102-90-0 dimethyl hexadecanedioate 
• 45247-78-7 16-oxohexadecanoic acid methyl ester 
• 57-10-3 1-hexadecylcarboxylic acid 
• 630-05-7 tritriacontane 
• 4200-95-7 1-heptadecanamine 
• 629-73-2 1-Hexadecene 
• 2096992-22-0 tert-butyl (3-(cyanomethyl)bicyclo[1.1.1]pentan-1-yl)carbamate 

Relevant articles and documents

Structure-activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors

Sphingosine-1-phosphate (S1P) is a ubiquitous, endogenous small molecule that is synthesized by two isoforms of sphingosine kinase (SphK1 and 2). Intervention of the S1P signaling pathway has attracted significant attention because alteration of S1P levels is linked to several disease states including cancer, fibrosis, and sickle cell disease. While intense investigations have focused on developing SphK1 inhibitors, only a limited number of SphK2-selective agents have been reported. Herein, we report our investigations on the structure-activity relationship studies of the lipophilic tail region of SLR080811, a SphK2-selective inhibitor. Our studies demonstrate that the internal phenyl ring is a key structural feature that is essential in the SLR080811 scaffold. Further, we show the dependence of SphK2 activity and selectivity on alkyl tail length, suggesting a larger lipid binding pocket in SphK2 compared to SphK1.

LONG CHAIN BASE SPHINGOSINE KINASE INHIBITORS

The invention relates to inhibitors of sphingosine kinase enzymatic activity, compounds and pharmaceutical compositions that inhibit sphingosine kinase 1 and sphingosine kinase 2 (SphK1 and SphK2) enzymes and further relates to methods of treating diseases and disorders mediated by sphingosine 1 phosphate activity, comprising administering an effective amount of sphingosine kinase inhibitors.

Iron-catalyzed alkyl-alkyl Suzuki-Miyaura coupling

Chemoselective Suzuki-Miyaura coupling of primary and secondary alkyl halides is realized by using an iron/Xantphos catalyst. Primary and secondary alkyl bromides undergo the reaction to give the coupling products in good yields. Application to the synthe

Applications of surfactant-modified clays to synthetic organic chemistry

Two triphase catalysts (SLL) have been developed for organic phase-aqueous phase reactions catalyzed by suitable modified clay (solid phase). These triphase catalysts have been applied to nucleophilic displacement on activated (benzylic) as well as unactivated organic halides and provide a convenient and effective method of preparation of the corresponding products. Other useful transformations to, which these triphase catalysts have been successfully applied are the synthesis of 9,9-dichloro bicyclo[6.1.0]nonane, O-alkylation and C-alkylation of β-naphthol.

Ovipositional responses of Chilo partellus (Swinhoe) (Lepidoptera: Pyralidae) to natural products from leaves of two maize (Zea mays L.) cultivars

Ovipositional responses of Chilo partellus (Swinhoe) (Lepidoptera: Pyralidae) to hexane extracts of leaves of two maize (Zea mays L.) cultivars, one resistant (Kisan) and one susceptible (Basilocal), were studied in two-choice bioassays. Gravid females laid a significantly higher percentage of eggs on substrates smeared with extract of Basilocal leaves (HEBL) (69%) than on those smeared with extracts of Kisan leaves (HEKL) (31%). Several chemicals were isolated from HEKL, three of which were characterized as dotriacontanol, heptadecanol, and nonadecanol. These chemicals were either absent or were present in very small amounts in HEBL, but in HEKL they were detected in much larger amounts. Each isolated chemical was tested for its effect on C. partellus oviposition in two-choice bioassays. Maximum ovipositional deterrence (90%) was observed for the compound MR-22a, followed in decreasing order by nonadecanol, MR-7, and heptadecanol. The identity of the remaining compounds is being investigated. The results indicate that the relative resistance of Kisan maize compared to Basilocal is partly due to the presence of certain ovipositional deterrents in its leaves.

A facile one-pot cyanation of primary and secondary alcohols. Application of some new Mitsunobu reagents

Some new Mitsunobu reagents, especially N,N,N',N'-tetramethylazodicarboxamide(TMAD)-tributylphosphine (TBP) and cyanomethylenetrimethylphosphorane (CMMP), mediated the direct transformation of primary and secondary alcohols into the corresponding nitriles in the presence of acetone cyanohydrin. This type of cyanation process can convert 3β-cholestanol to 3α-cyanocholestane in high yield with complete Walden inversion.

Betylates. 4. The synthesis and preparative nucleophilic substitution reactions of alkyl S-betylates

Alkyl S-betylates (S,S-dialkyl-S-3propylsulfonium salts), the first examples of S-betylates (sulfonioalkanesulfonic esters), have been synthesized by two routes, and their suitability as intermediates in the transformation of alcohols by nucleophilic substitution reactions examined.They have been found to react readily in stoichiometric phase transfer processes, including substrate-reagent ion-pair reactions, like their previously studied nitrogen analogues, with the following particular features: (a) they may be used with basic nucleophiles (unlike betylates), (b) they are more simply made from commercially available starting materials than betylates, and (c) they can be made by a route that avoids a final alkylation step.

Mechanisms of Polymer-Supported Catalysis. 2. Reaction of Benzyl Bromide with Aqueous Sodium Cyanide Catalyzed by Polystyrene-Bound Onium Ions

Rates of reaction of benzyl bromide in toluene with aqueous sodium cyanide in triphase mixtures with polystyrene-supported benzyltrimethylammonium and benzyltri-n-butylphosphonium ions as phase-transfer catalysts depend upon mechanical stirring speed, catalyst particle size, and percent of cross-linking of the polymer support.Increases in stirring speed increase reaction rates up to a maximum at about 600 rpm.Decreases in particle size increase reaction rates.Increases in polymer cross-linking decrease reaction rates.Apparent activation energies with benzyltrimethylammoniumion catalyst are 12 - 15 kcal/mol at 70 - 90 deg C.Rates of reaction of benzyl bromide, benzyl chloride, 1-bromooctane, and 1-bromohexadecane all are affected differently by variations in catalyst structure, particle size, and cross-linking.The results are discussed in terms of mass transfer, intraparticle diffusion, and intrinsic reactivity limitations on reaction rates.Slow intraparticle diffusion reduces the reactivity differences between benzyl bromide and 1-bromooctane and between benzyl bromide and benzyl chloride and causes 1-bromohexadecane to react much slower than 1-bromooctane.

Crown Cation Complex Effects. 10. Potassium tert-Butoxide Mediated Penultimate Oxidative Hydrolysis of Nitriles

The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions.An alternative hydrolysis method which involves potassium tert-butoxide mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented.The isolated yields reported here range from 21-93percent and are found to be highest for long-chain aliphatic nitriles such as cyanohexadecane.