21020-24-6

Basic information

• Product Name: 3-CHLORO-1-BUTYNE
• Synonyms: 1-Butyne, 3-chloro-;3-chloro-1-butyn;3-CHLORO-1-BUTYNE;3-chlorobut-1-yne;3-CHLORO-1-BUTYNE 98+%;2-Chloro-3-butyne
• CAS NO: 21020-24-6
• Molecular Formula: C₄H₅Cl
• Molecular Weight: 88.54
• EINECS: 244-151-2
• Product Categories: Acetylenes;Diyne Compounds (LB Films);Functional Materials;Functionalized Acetylenes;LB Films
• Mol File: 21020-24-6.mol

Chemical Properties

• Melting Point: -93.5°C (estimate)
• Boiling Point: 68°C
• Flash Point: °C
• Appearance: /
• Density: 0,96 g/cm3
• Vapor Pressure: 151mmHg at 25°C
• Refractive Index: 1.4230-1.4270
• CAS DataBase Reference: 3-CHLORO-1-BUTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-1-BUTYNE(21020-24-6)
• EPA Substance Registry System: 3-CHLORO-1-BUTYNE(21020-24-6)

Safety Data

• Statements: 11
• Safety Statements: 9-16-33
• RIDADR: 1993
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 21020-24-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-1-butyne is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to facilitate the creation of complex molecular structures that are otherwise challenging to produce.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Chloro-1-butyne is utilized as a precursor in the development of pesticides and other crop protection agents, contributing to the advancement of agricultural productivity and pest management.
Used as a Solvent:
3-Chloro-1-butyne serves as a solvent in various chemical processes, providing a medium for reactions to occur, and is particularly useful in applications where its unique solvency properties are required.
Used as a Precursor in Organic Compounds Manufacturing:
3-Chloro-1-butyne is employed as a precursor in the manufacturing of other organic compounds, leveraging its reactivity to form new chemical entities that are used across different industries.

InChI:InChI=1/C4H5Cl/c1-3-4(2)5/h1,4H,2H3

Upstream product

• 107-00-6 but-1-yne 
• 2028-63-9 but-3-yn-2-ol 
• 53487-52-8 1-methylprop-2-ynyl p-toluenesulfonate 

Downstream Products

• 127498-13-9 10-(1-methyl-1,2-propadienyl)-9(10H)-acridinone 
• 127498-14-0 10-(1-methyl-2-propynyl)-9(10H)-acridinone 
• 127498-16-2 9-(1-methyl-2-propynyloxy)acridine 
• 127498-15-1 10-<1-methyl-3-(3,4-dimethylphenyl-2-propynyl)>-9(10H)-acridinone 
• 86236-17-1 (formyl-4 hydroxy-3 phenoxy)-3 butyne-1 
• 86236-16-0 2,4-Bis-(1-methyl-prop-2-ynyloxy)-benzaldehyde 
• 103934-05-0 4-methyl-1-phenyl-5-hexyn-3-ol 
• 172978-27-7 4-Chloro-1-phenyl-pent-2-yn-1-ol 
• 104051-34-5 (+/-)-(1R,2S)-1-cyclohexyl-2-methylbut-3-yn-1-ol 
• 103934-06-1 (1RS,2RS)-1-cyclohexyl-2-methylbut-3-yn-1-ol 
• 76176-29-9 Benzylamine-,α-methyl-N-[4-(methylene)-5-(methyl)-1,3-dithiolan-2-ylidene] 
• 1344338-00-6 N-(2,6-dimethylphenyl)-N-2(but-3-ynyl) amine 
• 92752-98-2 (C₆H₅)3SnCCCH(Cl)CH₃ 
• 458561-07-4 [RhCl(κ(2)-O2CCH3)(CHCCHMe)(PPh2(Pr-i))2] 

Relevant articles and documents

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

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.

Hydroxyureas as noncovalent proteasome inhibitors

Inhibitors with a new mechanism of action are needed for 20S proteasome (CP) inhibition owing to the ineffectiveness of current market drugs against some types of solid tumors. A novel class of nonpeptidic CP inhibitors has been developed, which display reversible and noncovalent binding. The structure-based design of these highly active and site-specific inhibitors revealed unexplored binding subpockets.

Novel, stereoselective and stereospecific synthesis of allenylphosphonates and related compounds via palladium-catalyzed propargylic substitution

We have developed a novel method for the synthesis of allenylphosphonates and related compounds based on a palladium(0)-catalyzed reaction of propargylic derivatives with H-phosphonate, H-phosphonothioate, H-phosphonoselenoate, and H-phosphinate esters. The reaction is stereoselective and stereospecific, and provides a convenient entry to a vast array of allenylphosphonates and their analogues with diverse substitution patterns in the allenic moiety and at the phosphorus center. Some mechanistic aspects of this new reaction were also investigated. Copyright

Anti-AIDS agents 84. Synthesis and anti-human immunodeficiency virus (HIV) activity of 2′-monomethyl-4-methyl- and 1′-thia-4-methyl-(3′R, 4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogs

In a continuing investigation into the pharmacophores and structure-activity relationship (SAR) of (3′R,4′R)-3′, 4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) as a potent anti-HIV agent, 2′-monomethyl substituted 1′-oxa, 1′-thia, 1′-sulfoxide, and 1′-sulfone analogs were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. Among them, 2′S-monomethyl-4-methyl DCK (5a)? and 2′S-monomethyl-1′-thia-4-methyl DCK (7a) exhibited potent anti-HIV activity with EC50 values of 40.2 and 39.1 nM and remarkable therapeutic indexes of 705 and 1000, respectively, which were better than those of the lead compound DCK in the same assay. In contrast, the corresponding isomeric 2′R-monomethyl-4-methyl DCK (6) and 2′R-monomethyl- 1′-thia-4-methyl DCK (8) showed much weaker inhibitory activity against HIV-1 replication. Therefore, the bioassay results suggest that the spatial orientation of the 2′-methyl group in DCK analogs can have important effects on anti-HIV activity of this compound class.

Gas phase surface-catalyzed HCl addition to vinylacetylene: motion along a catalytic surface. Experiment and theory

Gaseous mixtures of HCl and vinylacetylene were permitted to react in Pyrex IR cells (NaCl windows). Gaseous 4-chloro-1,2-butadiene and 2-chloro-1,3-butadiene (chloroprene) were the major products. Kinetic data (FTIR) generated a rate expression in concert with surface catalysis. Computational studies involving surface associated water provide a view that accounts for the experimentally determined orders and a bifurcated pathway producing both products. The results are in accord with wall-adsorbed reactant(s) as well as previously reported computational studies on the reactants.

SN2'Substitutions of 1,3-Dichloropropenes with the Functionalized Copper-Zinc Reagents RCu(CN)ZnX

The addition of benzenesulfenyl (or benzeneselenyl) chlorides to propargylic chlorides affords regio- and stereospecifically (E)-1,3-dichloro-2-phenylsulfenyl (or phenylselenyl) propenes (2a-c).These new reagents were found to react with excellent SN2'selectivity with the highly functionalized copper-zinc reagents RCu(CN)ZnX, affording polyfunctional vinylic-thioethers or -selenides of type 3.The acidic hydrolysis of 3 furnishes symmetrical ketones in good yields.

SYNTHESIS OF ALKYL HALIDES UNDER NEUTRAL CONDITIONS

Primary and secondary alcohols are efficiently converted to the corresponding alkyl halides under neutral conditions.

SYNTHESIS OF ISOCOUMARINS VIA THALLATION-OLEFINATION OF BENZOIC ACIDS

Benzoic acid and substituted benzoic acids are readily thallated by thallium(III) trifluoroacetate and subsequently reacted with palladium chloride and simple olefins, allylic halides, vinyl halides, or vinyl esters to give isocoumarins.The organic halide reactions are catalytic in palladium. 1,2- and 1,3-dienes also react catalytically to afford 4-alkylidene- and 3-vinyl-3,4-dihydroisocoumarins, respectively.Vinylcyclopropanes also afford 3-vinyl-3,4-dihydroisocoumarins.This highly convenient thallation-olefination approach appears quite general for the synthesis of isocoumarins.