873-73-4

Basic information

• Product Name: 4-Chlorophenylacetylene
• Synonyms: (p-Chlorophenyl)acetylene;p-Ethynylchlorobenzene;Benzene, 1-chloro-4-ethynyl- (6CI, 7CI, 8CI, 9CI);4-CHOROPHENYLACETYLENE;(4-Chlorophenyl)ethyne;1-(4-Chlorophenyl)ethyne;4-Ethynyl-1-chlorobenzene;1-Chloro-4-ethynylbenzene,98%
• CAS NO: 873-73-4
• Molecular Formula: C₈H₅Cl
• Molecular Weight: 136.58
• Product Categories: pharmacetical;Aromatics Compounds;Aromatics;Alkynyl;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;Pyridines
• Mol File: 873-73-4.mol
• Article Data: 94

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 79-82 °C (23 mmHg)
• Flash Point: 10 °C
• Appearance: Yellow to pale brown/Crystalline Mass
• Density: 1.15 g/cm³
• Vapor Pressure: 1.33mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Keep Cold
• Water Solubility: Insoluble in water. Soluble in acetone, chloroform, dichloromethane, DMF, DMSO, ethanol, ethyl acetate, hexane, methanol,THF and
• Stability: Light Sensitive
• CAS DataBase Reference: 4-Chlorophenylacetylene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorophenylacetylene(873-73-4)
• EPA Substance Registry System: 4-Chlorophenylacetylene(873-73-4)

Safety Data

• Hazard Codes: F,Xi
• Statements: 36/37/38-11
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• HazardClass: FLAMMABLE
• PackingGroup: Ⅱ
• Hazardous Substances Data: 873-73-4(Hazardous Substances Data)

Usage

Description

4-Chlorophenylacetylene, also known as 1-Chloro-4-ethynylbenzene, is an organic compound characterized by its white crystalline solid appearance. It is known for undergoing standard Sonogashira reactions with iodophenyl groups on film surfaces, leading to the formation of C-C bonds.

Uses

Used in Pharmaceutical Industry:
4-Chlorophenylacetylene is utilized as a pharmaceutical intermediate, playing a crucial role in the synthesis of various pharmaceutical compounds. Its unique chemical properties and reactivity in Sonogashira reactions make it a valuable component in the development of new drugs and therapeutic agents.

InChI:InChI=1/C8H5Cl/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

Upstream product

• 99-91-2 para-chloroacetophenone 
• 3246-80-8 9-phenyl-9H-xanthene 
• 37614-57-6 3-(4-chlorophenyl)prop-2-yn-1-ol 
• 51738-09-1 α,p-dichlorostyrene 
• 40886-60-0 3-(4-Chloro-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 27491-70-9 dimethyl diazomethylphosphonate 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 77589-05-0 5-p-Chlorophenyl-2-phenylimino-1,3-oxathiole 
• 103-72-0 phenyl isothiocyanate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 107-19-7 propargyl alcohol 
• 33491-03-1 1-(bromoethynyl)-4-chlorobenzene 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 

Downstream Products

• 1201-88-3 (Ξ)-4,α-dichloro-β-nitro-styrene 
• 51118-06-0 1,4-bis(4-chlorophenyl)buta-1,3-diyne 
• 6178-24-1 (4-chloro-phenyl)-(4-chloro-cis-styryl)-sulfide 
• 6510-80-1 (4-chloro-phenyl)-(4-chloro-trans-styryl)-sulfide 
• 31554-58-2 3-(4-bromophenyl)-5-(4-chlorophenyl)isoxazole 
• 37614-57-6 3-(4-chlorophenyl)prop-2-yn-1-ol 
• 14688-30-3 3,5-di(p-chlorophenyl)isoxazole 
• 42866-55-7 (4-Chloro-phenyl)-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-acetaldehyde 
• 2809-65-6 4-chloro-1-propynylbenzene 
• 42289-90-7 1-Chloro-4-(4-chloro-3,3,4-trifluoro-cyclobut-1-enyl)-benzene 
• 26792-74-5 3,3-Bis-dimethylamino-1--propin-(1) 
• 25631-76-9 3-(4-Chloro-phenyl)-4,4-bis-trifluoromethyl-cyclobut-2-enone 
• 33206-26-7 6-(4-chloro-phenyl)-2-trichloromethyl-[1,3]oxazin-4-one 
• 25631-94-1 3-(4-Chloro-phenyl)-5-phenyl-6,6-bis-trifluoromethyl-cyclohexa-2,4-dienone 

Relevant articles and documents

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

Fritsch-Buttenberg-Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch-Buttenberg-Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using13C-labeled sulfoxides and by using DFT calculations.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea