10147-11-2

Basic information

• Product Name: 3-PHENYL-1-PROPYNE
• Synonyms: 3-PHENYL-1-PROPYNE;3-Phenyl-1-propyne, stabilized, 97%;3-PHENYL-1-PROPYNE 97%;(2-Propynyl)benzene;Propargylbenzene;3-Phenyl-1-propyne,97%,stabilized;prop-2-ynylbenzene;3-Phenyl-1-propyne ,96% [stabilized]
• CAS NO: 10147-11-2
• Molecular Formula: C₉H₈
• Molecular Weight: 116.16
• Product Categories: Alkynes;Organic Building Blocks;Terminal
• Mol File: 10147-11-2.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 75 °C20 mm Hg(lit.)
• Flash Point: 126 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.934 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.2mmHg at 25°C
• Refractive Index: n20/D 1.526(lit.)
• Storage Temp.: Flammables area
• CAS DataBase Reference: 3-PHENYL-1-PROPYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-1-PROPYNE(10147-11-2)
• EPA Substance Registry System: 3-PHENYL-1-PROPYNE(10147-11-2)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39-37/39
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 10147-11-2(Hazardous Substances Data)

Usage

Description

3-Phenyl-1-propyne, also known as propargyl benzene, is a 3-aryl-1-propyne compound characterized by its clear colorless to yellow liquid appearance. It has been studied for its electronic transition and resonance-stabilized 1-phenylpropargyl radical properties, as well as its microwave rotational spectrum. The stable conformation of 3-phenyl-1-propyne is reported to have coplanar carbon atoms, which contributes to its unique chemical properties and reactivity.

Uses

Used in Chemical Synthesis:
3-Phenyl-1-propyne is used as a starting material in the synthesis of various organic compounds, such as 4-phenyl-2-butyn-1-ol, which is an important intermediate in the production of pharmaceuticals and other specialty chemicals. Its reactivity with different reagents allows for the formation of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Phenyl-1-propyne is used as a key intermediate in the preparation of beta-hydroxytriazoles and indoles. These compounds have potential applications in the development of new drugs and therapeutic agents, due to their diverse chemical structures and biological activities.
Used in Research and Development:
3-Phenyl-1-propyne is also utilized in research and development for studying its chemical properties, reactivity, and potential applications in various fields. The study of its electronic transition and resonance-stabilized radical properties provides valuable insights into its behavior and potential uses in chemical reactions and processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 1837, 1982 DOI: 10.1021/jo00349a007

InChI:InChI=1/C9H8/c1-2-6-9-7-4-3-5-8-9/h1,3-5,7-8H,6H2

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 60-29-7 diethyl ether 
• 63145-54-0 1,2,3-tribromopropene 
• 463-49-0 1,2-propanediene 
• 10199-66-3 benzoylpyrazole 
• 627-09-8 Propargyl acetate 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 106-96-7 propargyl bromide 
• 100-58-3 phenylmagnesium bromide 
• 103-79-7 1-phenyl-acetone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 4301-14-8 acetylenemagnesium bromide 
• 28557-00-8 phenylzinc chloride 

Downstream Products

• 3623-15-2 phenyl propargyl ketone 
• 135511-01-2 (1-Ethynyl-pent-4-ynyl)-benzene 
• 135511-07-8 (1-But-3-ynyl-1-ethynyl-pent-4-ynyl)-benzene 
• 134529-34-3 3-[1-Phenyl-meth-(E)-ylidene]-5-o-tolyl-3H-furan-2-one 
• 134529-28-5 (E)-3-benzylidene-5-(4-chlorophenyl)furan-2(3H)-one 
• 124175-77-5 2,3-di-tert-butoxy-4-hydroxy-4-(3-phenyl-1-propynyl)-cyclobut-2-en-1-one 
• 118041-92-2 3-Ethoxy-4-hydroxy-2-phenyl-4-(3-phenyl-1-propynyl)-2-cyclobuten-1-one 
• 124175-74-2 3-tert-butoxy-2-n-butyl-4-hydroxy-4-(3-phenylprop-1-ynyl)cyclobut-2-en-1-one 
• 154670-40-3 (3-Phenyl-prop-1-ynyl)-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 2327-99-3 1-phenylpropadiene 
• 77117-34-1 <1-²H>-3-phenylpropyne 
• 17221-23-7 (1,2-dichloropropan-2-yl) benzene 
• 134529-30-9 (E)-3-benzylidene-5-(4-methoxyphenyl)furan-2(3H)-one 
• 96445-50-0 2,3-Dimethoxy-4-(3-phenyl-1-propynyl)-4-<(trimethylsilyl)oxy>-2-cyclobuten-1-one 

Relevant articles and documents

Single-compound libraries of organic materials: Parallel synthesis and screening of fluorescent dyes

"Hits" with high quantum yields: The screening of the chromophores of a coumarin library for optical properties allowed the identification of "hits" with high fluorescence quantum yields (see picture) which could be used as fluorescence labels and laser dyes. The generation of the library was facilitated by an efficient method involving the parallel synthesis utilizing Pd-catalyzed cross-coupling reactions.

HIGHLY CHEMOSELECTIVE COUPLING REACTIONS OF ORGANOVANADIUM COMPOUNDS

Organovanadium compounds generated in dichloromethane from equimolar amounts of vanadium trichloride and Grignard reagents underwent the chemoselective cross-coupling reaction with acid chlorides leading to the corresponding ketones.Treatment with allyl halides resulted in allylation of organovanadium compounds.In the case of propargyl bromide, regioselective displacement occured to produce allene derivatives.

Synthesis of acetylenes via dehydrobromination using solid anhydrous potassium phosphate as the base under phase-transfer conditions

Phase-transfer catalyzed preparation of acetylenes from the corresponding vicinal dibromo compounds via double dehydrobromination using the mild solid base, anhydrous potassium phosphate, under very mild conditions is reported.

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Dehydrosilylation of Alkenylsilanes Utilizing Polyvalent Organoiodine Compounds

Alkenylsilanes, on treatment with iodosylbenzene activated by co-ordination of boron trifluoride-diethyl ether to the oxygen atom, give the corresponding alkynes in good to excellent yields, presumably via vinyliodine(III) intermediates.

A Close-to-Aromatize Approach for the Late-Stage Functionalization through Ring Closing Metathesis

An efficient approach for the synthesis of monosubstituted aromatic compounds relying on a ring-closing metathesis followed by spontaneous 1,2-elimination is presented. The efficiency for late-stage functionalization is highlighted in various solvents (up to 920 TON). This approach is compatible with strained cycles and other multiple bonds in the substrate.

Lithium bis-(diisopropylamino)boracetylide [LiC≡C-B(ni-Pr2)2]. A new reagent for the preparation of terminal alkynes

Terminal alkynes RC≡CH [R = PhCO, PhCH2OCO, (CH3)2CHCH2OCO. Et2NCO. (EtO)2P(O), PhCH2, H2C=CH-CH2, and Ph-CH(OH)-] may be prepared in satisfactory yield in a one-pot process by reaction in THF at -78°C of the titled reagent with electrophiles followed by acidic workup with dilute HCl.

Compound of dipyrrolopyridine structure Preparation method and medical application

The invention discloses a compound with a dipyrrolo-pyridine structure as well as a preparation method and medical application thereof. The compound provided by the invention has obvious inhibitory activity on JAK family proteins, is an effective JAK inhibitor, and has the prospect of being developed into drugs for inhibiting JAK and further treating diseases.

Ruthenium-Catalyzed Propargylic Reduction of Propargylic Alcohols with Hantzsch Ester

Ruthenium-catalyzed propargylic reduction of propargylic alcohols bearing a terminal alkyne moiety is accomplished by using Hantzsch ester as a nucleophilic hydride source. A variety of secondary and tertiary propargylic alcohols are reduced to the corresponding propargylic reduced products such as 1-alkynes in excellent yields. Some mechanistic studies indicate that ruthenium-allenylidene complexes may work as key reactive intermediates.