17825-58-0

Basic information

• Product Name: 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid
• Synonyms: 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid;2,3-DIPHENYL-2-CYCLOPROPENE-1-CARBOXYLIC ACID;1,2-Diphenyl-cyclopropene-3-carboxylic acid;2,3-di(phenyl)-1-cycloprop-2-enecarboxylic acid
• CAS NO: 17825-58-0
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.26528
• Mol File: 17825-58-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 209.5-211.5 °C
• Boiling Point: 394.1°Cat760mmHg
• Flash Point: 181.9°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 6.43E-07mmHg at 25°C
• Refractive Index: 1.67
• PKA: 3.88±0.60(Predicted)
• CAS DataBase Reference: 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid(17825-58-0)
• EPA Substance Registry System: 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid(17825-58-0)

Safety Data

• Hazardous Substances Data: 17825-58-0(Hazardous Substances Data)

Usage

General Description

2,3-Diphenylcycloprop-2-ene-1-carboxylic acid is a chemical compound with a molecular formula C17H12O2. It is a cyclopropene carboxylic acid derivative, which means it contains a three-membered ring with two aromatic phenyl groups and a carboxylic acid functional group. 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid is commonly used in organic synthesis and medicinal chemistry as a building block for creating new molecules with potential pharmaceutical or biological activity. Its unique structure and reactivity make it an important intermediate in the development of new drugs and materials.

InChI:InChI=1/C16H12O2/c17-16(18)15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10,15H,(H,17,18)

Synthetic route

ethyl 2,3-diphenylcycloprop-2-enecarboxylate (7382-06-1) → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 48h; Hydrolysis;	95%
Stage #1: ethyl 2,3-diphenylcycloprop-2-enecarboxylate With water; potassium hydroxide In methanol at 20℃; for 48h; Stage #2: With hydrogenchloride In water pH=1;	93%

diazoacetic acid ethyl ester (623-73-4) + diphenyl acetylene (501-65-5) → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
(i) Cu, (heating), (ii) KOH; Multistep reaction;

diphenyl acetylene (501-65-5) + bis(1,3,2-dioxaborol-2-yl)dicobaltatetrahedrane → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / Cu-bronze 2: 95 percent / KOH / tetrahydrofuran; methanol; H2O / 48 h / 20 °C View Scheme

diphenyl acetylene (501-65-5) + thiocyanato → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: rhodium acetate dimer / CH2Cl2 / 35 °C 2: KOH / methanol / 4 h / Heating View Scheme

diphenyl acetylene (501-65-5) → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Cu / 0.25 h / 105 °C 2: KOH / methanol; H2O / 1 h / Heating View Scheme

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + benzyl bromide (100-39-0) → 2,3-Diphenyl-cycloprop-2-enecarboxylic acid benzyl ester (99838-01-4)

Conditions	Yield
With N(Et)4(1+)*(2-pyrrolidone-anion) In N,N-dimethyl-formamide for 1h; Ambient temperature;	99%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 2,3-diphenyl-2-cyclopropene-1-carbonyl chloride (6415-58-3)

Conditions	Yield
With oxalyl dichloride In chloroform for 48h; Ambient temperature; further reagent: SOCl2;	92%
With thionyl chloride	90%
With thionyl chloride

N-hydroxyphthalimide (524-38-9) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → N-(2,3-diphenyl-2-cyclopropenylcarbonyloxy)phthalimide (234075-38-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Substitution;	87%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → N-(2,3-diphenylcycloprop-2-enyl)urea

Conditions	Yield
Stage #1: 2,3-diphenylcycloprop-2-enecarboxylic acid Stage #2: With ammonia	86%

diazomethane (186581-53-3, 908094-01-9) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → methyl 1,5-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-endo-6-carboxylate + methyl 1,5-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-exo-6-carboxylate

Conditions	Yield
In diethyl ether at -10℃; for 480h;	A 14% B 73%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + 1-oxo-2-(1-pyrrolin-1-ylium)-1H-indene-3-olat (15365-97-6, 109159-92-4) → (±)-1′,3′-dioxo-1a,6b-diphenyl-1a,1′,3′,4,5,6,6a,6b-octahydro-1H-spiro[cyclopropa[a]pyrro-lizine-2,2′-indene]-1-carboxylic acid

Conditions	Yield
In methanol at 25℃; for 10h; diastereoselective reaction;	71%

L-leucine (61-90-5) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-isobutyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	68%

glycylglycine (556-50-3) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4S,5S,6R)-4-[(carboxymethyl)carbamoyl]-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
With acetic acid In methanol; water for 12h; Reflux; diastereoselective reaction;	63%

indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + phenylglycin (2835-06-5) → (±)-(1R,4R,5S,6R)-1',3'-dioxo-1,4,5-triphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	61%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 1,2-dophenylcyclopropenylim perchlorate (37647-36-2)

Conditions	Yield
With perchloric acid; acetic anhydride In water at 0℃;	59%
With perchloric acid; acetic anhydride at 0℃; Inert atmosphere;	59%
With perchloric acid; acetic anhydride

2-amino-hexanoic acid (616-06-8) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-butyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	51%

glycine-glycine-glycine (556-33-2) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-4-({2-[(carboxymethyl)amino]-2-oxoethyl}carbamoyl)-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
With acetic acid In methanol; water for 12h; Reflux; diastereoselective reaction;	50%

2-aminooctanoic acid (644-90-6) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-hexyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	42%

L-phenylalanine (63-91-2) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-benzyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	39%

L-valine (72-18-4) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-isopropyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	22%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + phenylmagnesium bromide → 1-Benzoyl-2,3-diphenyl-cycloprop-2-en (2892-41-3)

Conditions	Yield
(i) (COCl)2, (ii) /BRN= 4720968/, Et2O; Multistep reaction;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → cis,cis-1,2-Diphenyl-cyclopropan-carbonsaeure-(3) (123121-31-3)

Conditions	Yield
With hydrogen; Lindlar's catalyst

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + acetonitrile (75-05-8) → 5-methyl-1,2-diphenyl-6-oxa-4-aza-spiro[2.4]hepta-1,4-dien-7-one (19402-90-5)

Conditions	Yield
With triphenylmethyl perchlorate Ambient temperature;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + acecyclone (641-57-6) → 9-Carboxy-7,8,10,11-tetraphenyl-9H-cycloheptaacenaphthalin (106437-16-5)

Conditions	Yield
In xylene Heating;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + sodium methylate (124-41-4) → Methyl-N-(1,2-diphenyl-cyclopropenyl-(3))-carbamat (17825-60-4)

Conditions	Yield
Multistep reaction;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + triphenylmethyl perchlorate → 1.2-Diphenyl-3-triphenylmethyl-cyclopropenylium-perchlorat

Conditions	Yield
With lithium carbonate

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 1,2-Diphenyl-cyclopropenyl-(3)-hexafluorophosphat

Conditions	Yield
With hexafluorophosphoric acid; acetic anhydride

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + dimethyl amine (124-40-3) → N.N-Dimethyl-N'-<2.3-diphenyl-2-cyclopropenyl>-harnstoff (17825-62-6)

Conditions	Yield
Multistep reaction;

5,5-Dimethyl-1-pyrroline N-oxide (3317-61-1) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → C22H22NO3

Conditions	Yield
In benzene Addition; UV-irradiation;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → methyl 3,5-diphenyl-1,4-dihydropyridazine-4-carboxylate (60220-49-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 14 percent / diethyl ether / 480 h / -10 °C 2: sodium methoxide / methanol / 0.08 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 73 percent / diethyl ether / 480 h / -10 °C 2: 96 percent / sodium methoxide / methanol / 0.08 h / 20 °C View Scheme

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 6,6 dimethyl-3-(3-hydroxypropyl)thio-1-(thiazol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 14 percent / diethyl ether / 480 h / -10 °C 2: sodium methoxide / methanol / 0.08 h / 20 °C 3: 95 percent / aq. potassium permanganate / acetone / 0.5 h View Scheme
Multi-step reaction with 3 steps 1: 73 percent / diethyl ether / 480 h / -10 °C 2: 96 percent / sodium methoxide / methanol / 0.08 h / 20 °C 3: 95 percent / aq. potassium permanganate / acetone / 0.5 h View Scheme

Upstream product

• 7382-06-1 ethyl 2,3-diphenylcycloprop-2-enecarboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 17825-60-4 Methyl-N-(1,2-diphenyl-cyclopropenyl-⁽³⁾)-carbamat 
• 37647-36-2 1,2-dophenylcyclopropenylim perchlorate 
• 234075-38-8 N-(2,3-diphenyl-2-cyclopropenylcarbonyloxy)phthalimide 
• 60220-49-7 methyl 3,5-diphenyl-1,4-dihydropyridazine-4-carboxylate 
• 65103-96-0 bis(2,3-diphenyl-2-cyclopropenyl)ether 
• 641-44-1 tribenzoylmethane 
• 2892-44-6 (2,3-diphenylcycloallyl)(phenyl)methanol 
• 80673-37-6 1-(2,3-Diphenyl-2-cyclopropen-1-yl)-2,2-diiodethanon 
• 80673-36-5 2,2-Dibrom-1-(2,3-diphenyl-2-cyclopropen-1-yl)ethanon 

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