66990-32-7

Basic information

• Product Name: 10,12-PENTACOSADIYNOIC ACID
• Synonyms: 10,12-PENTACOSADIYNOIC ACID;TIMTEC-BB SBB009109;10,12-PENTACOSADIYNECARBOXYLIC ACID;10,12-PENTACOSADIYNOIC ACID, 98+%;Pentacosa-10,12-diynoic acid;10,12-Pentacosadiynoic acid >=97.0% (HPLC);10,12-Pentacosadiynioic acid;DA 3261
• CAS NO: 66990-32-7
• Molecular Formula: C₂₅H₄₂O₂
• Molecular Weight: 374.6
• Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;Diacetylene Monocarboxylic Acids;Functional Materials;LB Films
• Mol File: 66990-32-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 62-63°C
• Boiling Point: 522.5 °C at 760 mmHg
• Flash Point: 246.9 °C
• Appearance: /
• Density: 0.93 g/cm³
• Vapor Pressure: 2.56E-12mmHg at 25°C
• Refractive Index: 1.485
• Storage Temp.: Refrigerator
• PKA: 4.78±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• BRN: 4189973
• CAS DataBase Reference: 10,12-PENTACOSADIYNOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 10,12-PENTACOSADIYNOIC ACID(66990-32-7)
• EPA Substance Registry System: 10,12-PENTACOSADIYNOIC ACID(66990-32-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 66990-32-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 66990-32-7 differently. You can refer to the following data:
1. 10,12-Pentacosadiynoic Acid is used in the preparation of colorimetric and fluorescence sensors for cationic surfactants.
2. 10,12-Pentacosadiynoic acid (PCDA) is an amphiphilic diacetylene that can be used:In combination with a semifluorinated tetracosane ((CF3(CF2)7(CH2)15CH3) to synthesize mixed monolayer by photopolymerization.For the conversion of hydrophobic upconverting nanoparticles (UCNPs) to hydrophilic.To synthesize a polymer by combining with pyridine-2-aldoxime for colorimetric detection of malathion.To synthesize a thermochromic sensor constituting polymer fibres with monomeric unit of two PCDA linked by a p-phenylene group (bis-PCDA-Ph).As an inert coating material upon self-assembly and photopolymerization to modify the surface of Fe3O4 nanoparticles.

InChI:InChI=1/C25H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25(26)27/h2-12,17-24H2,1H3,(H,26,27)

Synthetic route

undec-10-ynoic acid (2777-65-3) + 1-chloro-tetradec-1-yne (850622-13-8) → 10,12-pentacosanodiynoic acid (66990-32-7)

Conditions	Yield
With potassium hydroxide; methylamine; copper(l) chloride In tetrahydrofuran; methanol; water 1) 20 deg C, 4 h, 2) 40 deg C, 1 h;	52%

10,12-pentacosanodiynoic acid (66990-32-7) → pentacosa-10,12-diynoyl chloride (128937-83-7)

Conditions	Yield
With oxalyl dichloride In dichloromethane	100%
With thionyl chloride In Petroleum ether for 3h; Heating;	98%
With phosphorus pentachloride In benzene Heating;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 10,12-pentacosanodiynoic acid (66990-32-7) → N-succinimidyl 10,12-pentacosadiynoic acid ester (146064-06-4)

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;	100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 7h;	97%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	96%

10,12-pentacosanodiynoic acid (66990-32-7) → 10,12-pentacosadiynoic acid fluoride (625443-01-8)

Conditions	Yield
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 3h; Heating;	99%
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;	78%

morpholine (110-91-8) + 10,12-pentacosanodiynoic acid (66990-32-7) → C4H9NO*C25H42O2

Conditions	Yield
for 1.5h; Milling;	98%

10,12-pentacosanodiynoic acid (66990-32-7) + ethyl 2-(5-(N-(2-(2-(2-(2,3-diaminopropanoylamino)ethoxy)ethyl)carbamoyl)-3-bis(ethoxycarbonyl)methyl)amino)acetate (225116-00-7) → {[3-[(bis-ethoxycarbonylmethyl-amino)-methyl]-5-(2-{2-[2-(2,3-bis-pentacosa-10,12-diynoylamino-propionylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-benzyl]-ethoxycarbonylmethyl-amino}-acetic acid ethyl ester

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In acetonitrile for 12h; Ambient temperature;	97%

10,12-pentacosanodiynoic acid (66990-32-7) + methyl 2,3-diaminopropanoate p-toluenesulfonate → 2,3-bis-pentacosa-10,12-diynoylamino-propionic acid methyl ester

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In chloroform; N,N-dimethyl-formamide at 25℃; for 15h; Substitution;	96%

10,12-pentacosanodiynoic acid (66990-32-7) → 10,12-pentacosadiyne-1-ol (92266-90-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 1.5h; Inert atmosphere;	96%
With lithium aluminium tetrahydride In diethyl ether at 4 - 20℃; for 1.5h; Inert atmosphere;	96%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1.75h;	91%

10,12-pentacosanodiynoic acid (66990-32-7) + N-butylamine (109-73-9) → C4H11N*C25H42O2

Conditions	Yield
for 0.75h; Milling;	96%

10,12-pentacosanodiynoic acid (66990-32-7) + Toluene-4-sulfonic acid; compound with (S)-2,5-diamino-pentanoic acid ethyl ester → (S)-2,5-Bis-pentacosa-10,12-diynoylamino-pentanoic acid ethyl ester (1054631-89-8)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In chloroform at 25℃; for 12h;	95%

10,12-pentacosanodiynoic acid (66990-32-7) + diethylamine (109-89-7) → C4H11N*2C25H42O2

Conditions	Yield
for 0.75h; Milling;	94%

C66H86O41 + 10,12-pentacosanodiynoic acid (66990-32-7) → C91H126O42

Conditions	Yield
Stage #1: 10,12-pentacosanodiynoic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 0 - 20℃; for 12h; Stage #2: C66H86O41 In chloroform at 20℃; for 20h;	92%

methanol (67-56-1) + 10,12-pentacosanodiynoic acid (66990-32-7) → methyl pentacosa-10,12-diynoate (120650-77-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	91%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 18h; Inert atmosphere;

10,12-pentacosanodiynoic acid (66990-32-7) → sodium 10,12-pentacosadiynoate/10,12-pentacosadiynoic acid salt cocrystal

Conditions	Yield
With sodium hydroxide for 0.75h; Milling;	91%

10,12-pentacosanodiynoic acid (66990-32-7) + [(2-{2-[2-(2,3-diamino-propionylamino)-ethoxy]-ethoxy}-ethyl)-ethoxycarbonylmethyl-amino]-acetic acid ethyl ester; compound with trifluoro-acetic acid → [(2-{2-[2-(2,3-bis-pentacosa-10,12-diynoylamino-propionylamino)-ethoxy]-ethoxy}-ethyl)-ethoxycarbonylmethyl-amino]-acetic acid ethyl ester (225115-54-8)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In acetonitrile for 24h; Ambient temperature;	90%

tert-butyl [amine(methylthio)methylene]carbamate (173998-77-1) + 10,12-pentacosanodiynoic acid (66990-32-7) → tert-butyl (pentacosa-10,12-diynamido)methylthiomethylenecarbamate (1251828-72-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	89%

2-(2′-(2″-bromoethoxy)ethoxy)ethanol (57641-67-5) + 10,12-pentacosanodiynoic acid (66990-32-7) → 2-(2-(2-bromoethoxy)ethoxy)ethyl pentacosa-10,12-diynoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	89%

4,4'-bipiperidine (15336-72-8) + 10,12-pentacosanodiynoic acid (66990-32-7) → C10H20N2*2C25H42O2

Conditions	Yield
for 1.5h; Milling;	89%

N-ethylethane-1,2-diamine (110-72-5) + 10,12-pentacosanodiynoic acid (66990-32-7) → N-(2-(ethylamino)ethyl)pentacosa-10,12-diynamide

Conditions	Yield
Stage #1: 10,12-pentacosanodiynoic acid With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h; Stage #2: N-ethylethane-1,2-diamine In dichloromethane at 20℃;	88%
Stage #1: 10,12-pentacosanodiynoic acid With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h; Stage #2: N-ethylethane-1,2-diamine In dichloromethane at 20℃; for 1h;	88%

2-methoxy-ethanol (109-86-4) + 10,12-pentacosanodiynoic acid (66990-32-7) → 2-methoxyethyl pentacosa-10,12-diynoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 18h;	86%

Succinimide (123-56-8) + triethylamine (Et3N) + 10,12-pentacosanodiynoic acid (66990-32-7) → N-succinimidyl 10,12-pentacosadiynoic acid ester (146064-06-4)

Conditions	Yield
With 1,2-dichloro-ethane In dichloromethane	85%
With 1,2-dichloro-ethane In dichloromethane	85%

4-aminopyridine (504-24-5) + 10,12-pentacosanodiynoic acid (66990-32-7) → N-(pyridin-4-yl)pentacosa-10,12-diynamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	84%

10,12-pentacosanodiynoic acid (66990-32-7) + Propargylamine (2450-71-7) → N-(2-propynyl)pentacosa-10,12-diynamide (1166851-54-2)

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 16h;	83%

10,12-pentacosanodiynoic acid (66990-32-7) + C55H99N7O24S (261518-54-1) → C80H139N7O25S

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	80%

1,6-Hexanediamine (124-09-4) + 10,12-pentacosanodiynoic acid (66990-32-7) → N,N'-hexamethylenebispentacosa-10,12-diynamide (1204604-70-5)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h;	79%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 0 - 20℃;	65%

10,12-pentacosanodiynoic acid (66990-32-7) + 2-butyl-6-(piperazin-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (361161-29-7) → C45H63N3O3

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	79%

1-bromo-6-hexanol (4286-55-9) + 10,12-pentacosanodiynoic acid (66990-32-7) → 6-bromohexyl pentacosa-10,12-diynoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	78%

10,12-pentacosanodiynoic acid (66990-32-7) + Trimethylenediamine (109-76-2) → N,N'-propylenebispentacosa-10,12-diynamide (1412887-32-1)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h;	78%

10,12-pentacosanodiynoic acid (66990-32-7) + 1,4-diaminobutane (110-60-1) → N,N'-butylenebispentacosa-10,12-diynamide (1204604-69-2)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h;	76%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 0 - 20℃;	75%

10,12-pentacosanodiynoic acid (66990-32-7) + N,N-bis(carboxymethyl)-L-lysine (113231-05-3) → N(6)-pentacosa-10,12-diynoyl-N(2),N(2)-bis(carboxymethyl)lysine (1108712-97-5)

Conditions	Yield
Stage #1: 10,12-pentacosanodiynoic acid With 1-hydroxy-pyrrolidine-2,5-dione; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere; Stage #2: N,N-bis(carboxymethyl)-L-lysine With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 12h;	76%

10,12-pentacosanodiynoic acid (66990-32-7) + (S)-3-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-amino-N-octadecyl-propionamide → N-(10,12-pentacosadiynoyl)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serineoctadecylamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol at 20℃; for 14h;	75%

Upstream product

• 2777-65-3 undec-10-ynoic acid 
• 850622-13-8 1-chloro-tetradec-1-yne 

Downstream Products

• 92266-90-5 10,12-pentacosadiyne-1-ol 
• 110836-14-1 pentacosa-10,12-diynyl 4-methylbenzenesulfonate 
• 195007-60-4 4-(pentacosa-10,12-diynamido)benzoic acid 
• 94598-32-0 1-bromopentacosa-10,12-diyne 
• 120650-77-3 methyl pentacosa-10,12-diynoate 

Relevant articles and documents

Plenty of Room at the Top: A Multi-Scale Understanding of nm-Resolution Polymer Patterning on 2D Materials

Lamellar phases of alkyldiacetylenes in which the alkyl chains lie parallel to the substrate represent a straightforward means for scalable 1-nm-resolution interfacial patterning. This capability has the potential for substantial impacts in nanoscale electronics, energy conversion, and biomaterials design. Polymerization is required to set the 1-nm functional patterns embedded in the monolayer, making it important to understand structure–function relationships for these on-surface reactions. Polymerization can be observed for certain monomers at the single-polymer scale using scanning probe microscopy. However, substantial restrictions on the systems that can be effectively characterized have limited utility. Here, using a new multi-scale approach, we identify a large, previously unreported difference in polymerization efficiency between the two most widely used commercial diynoic acids. We further identify a core design principle for maximizing polymerization efficiency in these on-surface reactions, generating a new monomer that also exhibits enhanced polymerization efficiency.