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

Chemical Properties

Clear colorless to yellow liquid

Uses

3-Phenyl-1-propyne is used as a starting material in the synthesis of 4-phenyl-2-butyn-1-ol. It is also used in the preparation of beta-hydroxytriazoles and indoles.

Synthesis Reference(s)

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

General Description

3-Phenyl-1-propyne is a 3-aryl-1-propyne. The electronic transition of the resonance-stabilized 1-phenylpropargyl radical, produced in a jet-cooled discharge of 3-phenyl-1-propyne, has been studied by laser-induced fluorescence excitation and dispersed single vibronic level fluorescence (SVLF) spectroscopy. The microwave rotational spectrum of 3-phenyl-1-propyne (propargyl benzene) has been studied and its stable conformation is reported to have coplanar carbon atoms. Reaction of N-methyl-N-phenylhydrazine or N-phenylhydrazine with 3-phenyl-1-propyne is reported to yield indoles. 3-Phenyl-1-propyne is reported to react with styrene oxide and sodium azide, to afford β-hydroxytriazoles.

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 
• 4301-15-9 ethynyldimagnesium dibromide 
• 100-39-0 benzyl bromide 
• 463-49-0 1,2-propanediene 
• 13169-00-1 Methoxyallene 
• 70372-58-6 2-bromo-2-fluoro-1-phenylcyclopropane 
• 62393-43-5 E-1-Methyl-2-phenylvinyl-triflat 
• 10199-66-3 benzoylpyrazole 
• 627-09-8 Propargyl acetate 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 58541-15-4 trans-1-(trimethylsilyl)-3-phenyl-1-propene 
• 106-96-7 propargyl bromide 

Downstream Products

• 3623-15-2 phenyl propargyl ketone 
• 18753-56-5 3-Phenyl-5-(phenylmethyl)isoxazole 
• 59935-61-4 1-Diaethylamino-6-phenylhexadiin-(2,4) 
• 67396-36-5 (3-bromoprop-2-yn-1-yl)benzene 
• 67396-35-4 (E)-(2,3-dibromoallyl)benzene 
• 53635-40-8 1-dimethylamino-4-phenyl-2-butyne 
• 135511-01-2 (1-Ethynyl-pent-4-ynyl)-benzene 
• 135511-07-8 (1-But-3-ynyl-1-ethynyl-pent-4-ynyl)-benzene 
• 73845-38-2 methyl 4-phenylbut-2-ynoate 
• 77252-94-9 3-phenyl methylglyoxal dimethyl acetal 
• 134030-84-5 3,3-dimethoxy-1-phenyl-1,2-propanedione 
• 134030-83-4 1,1,3,3-tetramethoxy-1-phenyl-2-propanone 
• 134030-82-3 1,1-dimethoxy-3-phenyl-3-(phenylseleno)-2-propanone 
• 31683-47-3 1-(trimethylsilyl)-3-phenylprop-1-yne 

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.