35599-78-1

Basic information

• Product Name: 1-Iodopentadecane
• Synonyms: 1-Iodopentadecane
• CAS NO: 35599-78-1
• Molecular Formula: C₁₅H₃₁I
• Molecular Weight: 338.32
• Mol File: 35599-78-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 24°C
• Boiling Point: 324.55°C (estimate)
• Appearance: /
• Density: 1.1353 (rough estimate)
• Refractive Index: 1.4801
• CAS DataBase Reference: 1-Iodopentadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Iodopentadecane(35599-78-1)
• EPA Substance Registry System: 1-Iodopentadecane(35599-78-1)

Safety Data

• Hazardous Substances Data: 35599-78-1(Hazardous Substances Data)

Usage

Description

1-Iodopentadecane is an organic compound with the chemical formula C15H31I. It is a colorless to pale yellow liquid at room temperature and has a characteristic odor. The presence of the iodine atom in its structure makes it a versatile reagent in organic synthesis.

Uses

Used in Organic Synthesis:
1-Iodopentadecane is used as a reagent in cross-coupling reactions for the formation of carbon-carbon bonds. The iodine atom in its structure can be easily replaced by other metal atoms, making it a good candidate for palladium-catalyzed cross-coupling reactions such as the Suzuki, Heck, and Sonogashira reactions. These reactions are widely used in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Chemical Research:
1-Iodopentadecane is also used as a reference compound in chemical research, particularly in the study of reaction mechanisms and the development of new synthetic methods. Its reactivity and selectivity in various reactions make it a valuable tool for understanding the underlying principles of organic chemistry.
Used in Analytical Chemistry:
1-Iodopentadecane can be used as an internal standard in analytical chemistry, particularly in gas chromatography and mass spectrometry. Its unique chemical properties and stability make it suitable for accurate quantification and identification of other compounds in complex mixtures.

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Relevant articles and documents

A PRACTICAL ALTERNATIVE TO THE HUNSDIECKER REACTION

Carboxylic acid esters derived from N-hydroxy-pyridine-2-thione react with carbon tetrachloride, bromotrichloromethane or iodoform in a radical chain reaction to give the corresponding noralkyl chlorides, bromides or iodides in high yield.

THE INVENTION OF RADICAL REACTIONS. PART XVIII. DECARBOXYLATIVE RADICAL ADDITION TO ARSENIC, ANTIMONY, AND BISMUTH PHENYLSULPHIDES - A NOVEL SYNTHESIS OF NOR-ALCOHOLS FROM CARBOXYLIC ACIDS

Carbon centered radicals obtained by decarboxylative transformation of suitable thiohydroxamate esters react with group Va trisphenylsulphides to give intermediates of general formula R-M(SPh)2 (M= As, Sb, Bi).These react spontaneously with air to give the corresponding alcohols.This procedure is especially useful in the case where M=Sb.It is thus sufficient to stir the thiohydroxamate ester with tris(phenylthio)antimony under air to obtain the nor alcohol directly and in high yield.The intermediate organometalloid could also be oxidised with nitrogen dioxide to give the expected nitroalkane albeit in only modest yield.The corresponding organobismuth intermediate derived from 3,3-diphenylpropionic acid could actually be isolated thereby providing strong evidence for the proposed mechanism.

THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART VIII. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS; A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC ACIDS.

The aliphatic and alicyclic esters of N-hydroxy-pyridine-2-thione are readily reduced by tributylstannane in a radical chain reaction to furnish nor-alkanes.In the absence of the stannane a smooth decarboxylative rearrangement occurs to give 2-substituted thiopyridines.The radicals present in this reaction provoke with t-butylthiol an efficient radical reaction with formation of nor-alkane and 2-pyridyl-t-butyl disulphide.Similarly these carbon radicals can be captured by halogen atom transfer to give noralkyl chlorides, bromides and iodides.With oxygen in the presence of t-butylthiol the corresponding noralkyl hydroperoxides are formed in another radical chain reaction.