883106-26-1

Basic information

• Product Name: 3,5-DIETHYNYL-BENZOIC ACID
• Synonyms: 3,5-DIETHYNYL-BENZOIC ACID;3,5-Diethynyl-benozoic acid
• CAS NO: 883106-26-1
• Molecular Formula: C₁₁H₆O₂
• Molecular Weight: 170.16
• Mol File: 883106-26-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 355.0±37.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.78±0.10(Predicted)
• CAS DataBase Reference: 3,5-DIETHYNYL-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIETHYNYL-BENZOIC ACID(883106-26-1)
• EPA Substance Registry System: 3,5-DIETHYNYL-BENZOIC ACID(883106-26-1)

Safety Data

• Hazardous Substances Data: 883106-26-1(Hazardous Substances Data)

Usage

General Description

3,5-Diethynyl-benzoic acid is a chemical compound with the molecular formula C12H6O2. It is a carboxylic acid derivative with two ethynyl groups attached to the benzene ring at the 3 and 5 positions. 3,5-DIETHYNYL-BENZOIC ACID is primarily used as a building block for the synthesis of various organic and pharmaceutical compounds. Its unique structure and functional groups make it a valuable intermediate in organic chemistry, allowing for the creation of new molecules with specific properties and applications. Additionally, 3,5-diethynyl-benzoic acid has potential applications in materials science, such as in the development of advanced polymers and electronic materials.

Synthetic route

ethyl 3,5-bis[(trimethylsilyl)ethynyl]benzoate (437707-58-9) → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; water at 20℃; for 48h;	88%
Multi-step reaction with 2 steps 1: 76 percent / AcOH; tetrabutylammonium fluoride / tetrahydrofuran / 0.02 h 2: 50 percent / sodium hydroxide; water / methanol / 12 h / 20 °C View Scheme

ethyl 3,5-bis(3-hydroxy-3-methylbut-1-yn-1-yl)benzoate (1448422-96-5) → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol at 90℃; for 4h;	59%

methyl 3,5-bis((trimethylsilyl)ethynyl)benzoate → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 20℃; for 18h;	58%

ethyl 3,5-diethynylbenzoate (437707-60-3) → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
With sodium hydroxide; water In methanol at 20℃; for 12h;	50%

3,5-dibromobenzoic acid ethyl ester (67973-33-5) → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / CuI; PPh3; triethylamine / Pd2(dba)3 / 12 h / 65 °C 2: 76 percent / AcOH; tetrabutylammonium fluoride / tetrahydrofuran / 0.02 h 3: 50 percent / sodium hydroxide; water / methanol / 12 h / 20 °C View Scheme

3,5-dibromobenzoic acid (618-58-6) → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 22 h / Reflux 2.1: triethylamine / tetrahydrofuran / 22 h / Inert atmosphere 2.2: 15 h / 80 °C / Inert atmosphere 3.1: potassium hydroxide / isopropyl alcohol / 4 h / 90 °C View Scheme

methyl 3,5-dibromobenzoate (51329-15-8) → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine; triethylamine; tris-(dibenzylideneacetone)dipalladium(0) / 20 h / 65 °C 2: potassium hydroxide / tetrahydrofuran / 18 h / 20 °C View Scheme

N-Ac-L-Lys-OH (1946-82-3) + sodium 4-((3,5-diethynylbenzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate → 3,5-diethynyl-benzoic acid (883106-26-1) + C19H20N2O4

Conditions	Yield
In aq. phosphate buffer; acetonitrile at 37℃;

sodium 4-((3,5-diethynylbenzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate → 3,5-diethynyl-benzoic acid (883106-26-1)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol In water; butan-1-ol at 20℃;

3,5-diethynyl-benzoic acid (883106-26-1) + triethylene glucol monomethyl ether (112-35-6) → 2-(2-(2-methoxyethoxy)ethoxy)ethyl 3,5-diethynylbenzoate (398119-23-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 20℃; for 4h;	90%

5″-azide-1,3,2′,6′,2′″,6′″-hexa-N-(tert-butoxycarbonyl)-5″-deoxy-neomycin B (849676-07-9) + 3,5-diethynyl-benzoic acid (883106-26-1) → C117H192N18O50

Conditions	Yield
With copper(l) iodide; acetic acid; N-ethyl-N,N-diisopropylamine In toluene at 80℃; for 13h; Inert atmosphere;	86%

3,5-diethynyl-benzoic acid (883106-26-1) + 2,3,5,6-tetrafluoro-4-hydroxybenzene sulfonic acid sodium salt → sodium 4-((3,5-diethynylbenzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 22h; Inert atmosphere;	86%

3,5-diethynyl-benzoic acid (883106-26-1) + L-Alanine methyl ester (10065-72-2) → C15H13NO3

Conditions	Yield
With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 24h;	72%

3,5-diethynyl-benzoic acid (883106-26-1) + C38H40O8 + N-[4-(hydroxymethyl)benzyl]-3,5-di-tert-butylbenzylammonium hexafluorophosphate → C34H37NO2*C38H40O8*F6P(1-)*H(1+)

Conditions	Yield
With tributylphosphine; diisopropyl-carbodiimide In chloroform at 20℃; for 24h;	68%

3,5-diethynyl-benzoic acid (883106-26-1) + 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl (14691-88-4) → 3,5-diethynyl-N-(1-oxy-2,2,6,6-tetramethyl-piperidin-4-yl)-benzamide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 18h;	33%

3,5-diethynyl-benzoic acid (883106-26-1) → C2HF3O2*C35H39NO2*C38H40O8

Conditions	Yield
Multi-step reaction with 3 steps 1: tributylphosphine; diisopropyl-carbodiimide / chloroform / 24 h / 20 °C 2: sodium tris(acetoxy)borohydride; triethylamine / 1-methyl-pyrrolidin-2-one / 24 h / 20 °C / Inert atmosphere 3: dichloromethane / 0.08 h / 20 °C View Scheme

3,5-diethynyl-benzoic acid (883106-26-1) + C34H54N18O15 → C45H60N18O17

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol In water; tert-butyl alcohol at 20℃; for 16h; Inert atmosphere;

3,5-diethynyl-benzoic acid (883106-26-1) + C69H95N27O15 → C81H103N27O17

Conditions	Yield
With copper(ll) sulfate pentahydrate; 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol In water; tert-butyl alcohol

3,5-diethynyl-benzoic acid (883106-26-1) + C64H96N26O15 → C76H104N26O17

Conditions	Yield
With copper(ll) sulfate pentahydrate; 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol In water; tert-butyl alcohol

3,5-diethynyl-benzoic acid (883106-26-1) + oxalyl dichloride (79-37-8) → C11H5ClO

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 5h; Inert atmosphere;

3,5-diethynyl-benzoic acid (883106-26-1) → 2,4-dinitrophenyl 3,5-diethynylbenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / tetrahydrofuran / 21 h / 0 - 20 °C View Scheme

Upstream product

• 1946-82-3 N-Ac-L-Lys-OH 
• 51329-15-8 methyl 3,5-dibromobenzoate 
• 1448422-96-5 ethyl 3,5-bis(3-hydroxy-3-methylbut-1-yn-1-yl)benzoate 
• 618-58-6 3,5-dibromobenzoic acid 
• 67973-33-5 3,5-dibromobenzoic acid ethyl ester 
• 437707-58-9 ethyl 3,5-bis[(trimethylsilyl)ethynyl]benzoate 
• 437707-60-3 ethyl 3,5-diethynylbenzoate 

Downstream Products

• 398119-23-8 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-biethynylbenzoate 

Relevant articles and documents

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