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Propargyl iodide, also known as 3-iodo-1-propyne or 1-iodo-2-propyne, is an organic compound with the chemical formula C3H3I. It is a colorless liquid that is soluble in organic solvents and has a pungent odor. Propargyl iodide is a valuable building block in organic synthesis, particularly in the preparation of various pharmaceuticals, agrochemicals, and other specialty chemicals. It is synthesized through the reaction of propargyl alcohol with hydroiodic acid or by the iodination of propyne. Due to its reactivity, propargyl iodide can undergo various chemical transformations, such as nucleophilic substitution, addition reactions, and coupling reactions, making it a versatile intermediate in the synthesis of complex molecules.

659-86-9

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659-86-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 659-86-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,5 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 659-86:
(5*6)+(4*5)+(3*9)+(2*8)+(1*6)=99
99 % 10 = 9
So 659-86-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H3I/c1-2-3-4/h1H,3H2

659-86-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-iodoprop-1-yne

1.2 Other means of identification

Product number -
Other names ethynyliodide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:659-86-9 SDS

659-86-9Relevant academic research and scientific papers

A chemical labeling of N6-formyl adenosine (f6A) RNA

Xie, Li-Jun,Lin, Cui-Lian,Liu, Li,Cheng, Liang

supporting information, p. 1563 - 1566 (2021/10/06)

N6-methyl adenosine (m6A) is an eminent epigenetic mark in mRNAs that affects a broad range of biological functions in diverse species. However, the chemically inert methyl group prevents a direct labeling of this modification for subsequent detection and sequencing. Therefore, most current approaches for the labeling of m6A still have limitations of relying on the utilization of corresponding methyltransferases, which resulted in the lacking of efficiency. Here we present an approach which selectively alkylated the N6-formyl adenosine (f6A), the key intermediate during chemical oxidation of m6A, with an alkyne functionality that can be further labeled with click reactions. This covalent labeling approach will be able to facilitate in the affinity purification, detection and genome-wide profiling studies.

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

Munyemana, Fran?ois,Patiny, Luc,Ghosez, Léon

, (2021/06/07)

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

The Propargyl Rearrangement to Functionalised Allyl-Boron and Borocation Compounds

Wilkins, Lewis C.,Lawson, James R.,Wieneke, Philipp,Rominger, Frank,Hashmi, A. Stephen K.,Hansmann, Max M.,Melen, Rebecca L.

supporting information, p. 14618 - 14624 (2016/10/03)

A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon–carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(Cs

Ruthenium bipyridyl tethered porous organosilica: A versatile, durable and reusable heterogeneous photocatalyst

Jana, Avijit,Mondal, John,Borah, Parijat,Mondal, Sujan,Bhaumik, Asim,Zhao, Yanli

supporting information, p. 10746 - 10749 (2015/06/30)

A versatile heterogeneous photocatalysis protocol was developed by using ruthenium bipyridyl tethered porous organosilica (Ru-POS). The versatility of the Ru-POS catalyst in organo-photocatalysis was explored by (i) oxidative aromatization of Hantzsch ester, (ii) reductive dehalogenation of alkyl halides, and (iii) functional group interconversion (FGI) of alcohols to alkyl halides. This journal is

Theoretical support for the involvement of a radical pathway in the formation of allenylzincs from propargyl iodides and dialkylzincs: Influence of zinc coordination

Jammi, Suribabu,Mouysset, Dominique,Siri, Didier,Bertrand, Michèle P.,Feray, Laurence

, p. 1589 - 1603 (2013/04/10)

Propargyl iodides are good precursors for allenylzincs via reaction with diethylzinc, even in nondegassed medium. These reactions proceed via zinc/iodine exchange. Owing to the previously reported detection of propargyl radical by ESR experiments, in this process a radical mechanism was suspected. Calculations of the C-Zn BDEs in allenyl- and propargylzinc species were performed with the CBS-QB3 method to demonstrate that propargyl radicals could undergo homolytic substitution at zinc. The stabilization of allenylzinc derivatives by chelation, made possible by the selection of appropriate ortho-substituted 3-phenylalkynyl iodides as precursors, was shown to influence the regioselectivity of their addition to aldehydes and ketones. The more stabilized the chelated allenylzinc intermediate, the higher the ratio of homopropargylic alcohols.

COMPOSITIONS AND IMPROVED SOFT TISSUE REPLACEMENT METHODS

-

, (2012/03/10)

The present specification discloses compositions and methods of transplanting tissue useful for treating a soft tissue condition of an individual.

Ligand-accelerated enantioselective propargylation of aldehydes via allenylzinc reagents

Trost, Barry M.,Ngai, Ming-Yu,Dong, Guangbin

supporting information; experimental part, p. 1900 - 1903 (2011/06/21)

An enantioselective propargylation of aldehydes using an allenylzinc reagent generated in situ via a zinc-iodine exchange reaction is described. The enantioselectivity is controlled by addition of a catalytic amount of readily accessible and highly tunable amino alcohol ligand L13. A wide range of aldehydes can be propargylated to afford valuable and versatile homopropargyl alcohols in good to excellent yields with high levels of enantiopurity.

Rh(I)-catalyzed Pauson-Khand reaction of 1-phenylsulfonyl-1,2-octadien-7-yne derivatives

Inagaki, Fuyuhiko,Kawamura, Takamasa,Mukai, Chisato

, p. 5154 - 5160 (2008/02/01)

The Rh(I)-catalyzed PKR of 1-phenylsulfonyl-1,2-octadien-7-ynes and their aza derivatives exclusively produced the corresponding 9-phenylsulfonylbicyclo[4.3.0]nona-1,6-dien-8-ones and no 4-(phenylsulfonylmethylidene)bicyclo[3.3.0]oct-1-en-3-ones could be

Treatment of inflammatory bowel disease

-

, (2008/06/13)

Disclosed herein is a method comprising administering a compound to a mammal suffering from an inflammatory bowel disease for the treatment of said disease, said compound having a structure according to Formula I wherein X, Y, B, R2, R3, R4, R5, R6 and n have the meanings found herein.

10,10-dialkyl prostanoic acid derivatives as agents for lowering intraocular pressure

-

, (2008/06/13)

The present invention provides a method of treating ocular hypertension or glaucoma which comprises administering to an animal having ocular hypertension or glaucoma therapeutically effective amount of a compound represented by the general formula I; wherein the dashed line indicates the presence or absence of a bond, the hatched wedge indicates the α (down) configuration, and the solid triangle indicates the β (up) configuration; B is a single, double, or triple covalent bond; n is 0-6; X is CH2, S or O; Y is any pharmaceutically acceptable salt of CO2H, or CO2R, CONR2, CONHCH2CH2OH, CON(CH2CH2OH)2,CH2OR, P(O)(OR)2, CONRSO2R, SONR2, or R is H, C1-6 alkyl or C2-6 alkenyl; R2 and R3 are C1-6 linear alkyl which may be the same or different, and may be bonded to each other such that they form a ring incorporating the carbon to which they are commonly attached; R4is hydrogen, R, C(═O)R, or any group that is easily removed under physiological conditions such that R4 is effectively hydrogen; R5 is hydrogen or R; R6 is i) hydrogen; ii) a linear or branched hydrocarbon containing between 1 and 8 carbon atoms, which may contain one or more double or triple bonds, or oxygen or halogen derivatives of said hydrocarbon, wherein 1-3 carbon or hydrogen atoms may be substituted by O or a halogen; or iii) aryloxy, heteroaryloxy, C3-8 cycloalkyloxy, C3-8 cycloalkyl, C6-10 aryl or C3-10 heteroaryl, wherein one or more carbons is substituted with N, O, or S; and which may contain one or more substituents selected from the group consisting of halogen, trihalomethyl, cyano, nitro, amino, hydroxy, C6-10 aryl, C3-10 heteroaryl, aryloxy, heteroaryloxy, C1-6 alkyl, OR, SR, and SO2R. Some of the compounds of the present invention and some of their methods of preparation are also novel an nonobvious.

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