62281-07-6

Basic information

• Product Name: 11-(Aminomethyl)tricosane
• Synonyms: 11-(Aminomethyl)tricosane;2-(Dec-1-yl)tetradecylamine;2-decyltetradecan-1-amine
• CAS NO: 62281-07-6
• Molecular Formula: C₂₄H₅₁N
• Molecular Weight: 353.66844
• Mol File: 62281-07-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 418.3±13.0 °C(Predicted)
• Appearance: /
• Density: 0.824±0.06 g/cm3(Predicted)
• PKA: 10.70±0.10(Predicted)
• CAS DataBase Reference: 11-(Aminomethyl)tricosane(CAS DataBase Reference)
• NIST Chemistry Reference: 11-(Aminomethyl)tricosane(62281-07-6)
• EPA Substance Registry System: 11-(Aminomethyl)tricosane(62281-07-6)

Safety Data

• Hazardous Substances Data: 62281-07-6(Hazardous Substances Data)

Usage

Uses

2-Decyltetradecylamine is used in the synthesis of co-polymers with application in organic thin-film transistors.

Synthetic route

2-(2-decyltetradecyl)isoindoline-1,3-dione (135713-14-3) → 2-decyl-1-tetradecylamine (62281-07-6)

Conditions	Yield
With hydrazine hydrate In methanol; water for 16h; Reflux;	94%
With hydrazine hydrate In methanol at 95℃; for 12h; Inert atmosphere;	89%
With hydrazine hydrate In methanol at 95℃;
With hydrazine In methanol for 24h; Inert atmosphere; Schlenk technique; Reflux;

2-(2-decyltetradecyl)-3a,7a-dihydro-1H-isoindole-1,3(2H)-dione → 2-decyl-1-tetradecylamine (62281-07-6)

Conditions	Yield
With hydrazine In methanol at 95℃; for 12h; Inert atmosphere;	81%

11-bromomethyl-tricosane (732276-63-0) → 2-decyl-1-tetradecylamine (62281-07-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 60 °C 2: hydrazine / methanol / 24 h / Inert atmosphere; Schlenk technique; Reflux View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 2: hydrazine hydrate / methanol / 12 h / 95 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / Reflux 2: hydrazine hydrate / water; methanol / 16 h / Reflux View Scheme

2-decylteradecanol (58670-89-6) → 2-decyl-1-tetradecylamine (62281-07-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 3: hydrazine hydrate / methanol / 12 h / 95 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / 0.5 h / 0 °C 1.2: 2 h 2.1: N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 3.1: hydrazine / methanol / 12 h / 95 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere 1.2: 16 h 2.1: N,N-dimethyl-formamide / 16 h / Reflux 3.1: hydrazine hydrate / water; methanol / 16 h / Reflux View Scheme

toluene-4-sulfonic acid 2-decyl-1-tetradecyl ester (132004-78-5) → 2-decyl-1-tetradecylamine (62281-07-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: hydrazine / methanol / 12 h / 95 °C / Inert atmosphere View Scheme

2-decyl-1-tetradecylamine (62281-07-6) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N'-bis(2-decyltetradecyl)-3,4,9,10-perylene diimide (1187541-55-4)

Conditions	Yield
With 1H-imidazole; zinc diacetate at 160℃; Inert atmosphere;	99%
Stage #1: 2-decyl-1-tetradecylamine; perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With quinoline; zinc diacetate at 180℃; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water	87.3%
With quinoline; zinc diacetate

2-decyl-1-tetradecylamine (62281-07-6) + C18H4Br2O6S2 → C66H106Br2N2O6S2

Conditions	Yield
In chloroform at 50℃; for 2h;	94%

2-decyl-1-tetradecylamine (62281-07-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 1,3-dibromo-5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 120℃; for 24h; Inert atmosphere; Stage #2: With pyridine; dibromo sulfoxide In toluene at 0 - 120℃; for 29h; Inert atmosphere;	89.98%

2-decyl-1-tetradecylamine (62281-07-6) + 1,9-dibromothieno[2',3':4,5]thieno[3,2-c]thieno[2',3':4,5]thieno[2,3-e]oxepine-4,6-dione → 1,9-dibromo-5-(2-decyltetradecyl)-4H-thieno[2',3':4,5]thieno[3,2-c]thieno[2',3':4,5]thieno[2,3-e]azepine-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 1,9-dibromothieno[2',3':4,5]thieno[3,2-c]thieno[2',3':4,5]thieno[2,3-e]oxepine-4,6-dione With dmap In 1,4-dioxane at 100℃; Inert atmosphere; Schlenk technique; Stage #2: With acetic anhydride In 1,4-dioxane at 140℃; for 3h; Inert atmosphere; Schlenk technique;	89%

2-decyl-1-tetradecylamine (62281-07-6) + 9-bromothieno[2',3':4,5]thieno[3,2-c]thieno[2,3-e]oxepine-4,6-dione → 9-bromo-5-(2-decyltetradecyl)-4H-thieno[2',3':4,5]thieno[3,2-c]thieno[2,3-e]azepine-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 9-bromothieno[2',3':4,5]thieno[3,2-c]thieno[2,3-e]oxepine-4,6-dione With dmap In 1,4-dioxane at 100℃; Inert atmosphere; Schlenk technique; Stage #2: With acetic anhydride In 1,4-dioxane at 140℃; for 3h; Inert atmosphere; Schlenk technique;	84%

2-decyl-1-tetradecylamine (62281-07-6) + 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dianhydride (118129-60-5) → N,N-bis(2-decyl-1-tetradecyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide

Conditions	Yield
In water; butan-1-ol at 80℃; for 17h;	81%
In water; butan-1-ol at 80℃; for 17h; Inert atmosphere;	81%
With acetic acid

2-decyl-1-tetradecylamine (62281-07-6) + 1,2-dihydro-6-oxacyclopentaphenalene-5,7-dione (5699-00-3) → N-decyltetradecyl-1,2-dihydroacenaphthylenedicarboxylic acid imide (1443122-14-2)

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere;	80%
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere;	80%

2-decyl-1-tetradecylamine (62281-07-6) + C16H12Br2S2 → C62H104N2S2

Conditions	Yield
Stage #1: C16H12Br2S2 With tetrakis(triphenylphosphine) palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 25℃; for 0.333333h; Stage #2: 2-decyl-1-tetradecylamine In toluene at 120℃; for 4h;	80%

2-decyl-1-tetradecylamine (62281-07-6) + 4-bromophthalic anhydride (86-90-8) → 5-bromo-2-(2-decyltetradecyl)isoindoline-1,3-dione

Conditions	Yield
In acetic acid at 120℃; for 8h;	78%

2-decyl-1-tetradecylamine (62281-07-6) + 2-(thiophen-2'-yl)-5-(thiophen-2"-yl)thieno[3,2-b]thiophene-3,3,6,3-tetracarboxylic dianhydride → C66H102N2O4S4

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 2-(thiophen-2'-yl)-5-(thiophen-2"-yl)thieno[3,2-b]thiophene-3,3,6,3-tetracarboxylic dianhydride In dichloromethane for 4h; Inert atmosphere; Reflux; Stage #2: With thionyl chloride for 1h; Reflux;	76%

2-decyl-1-tetradecylamine (62281-07-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 100℃; for 24h; Stage #2: With thionyl chloride at 80℃; for 4h;	74%
With thionyl chloride In toluene

2-decyl-1-tetradecylamine (62281-07-6) + 5-Bromo-2-carboxymethyl-benzoic acid (19725-82-7) → 7-bromo-2-(2-decyltetradecyl)isoquinolinedione

Conditions	Yield
Stage #1: 5-Bromo-2-carboxymethyl-benzoic acid With acetic anhydride Stage #2: 2-decyl-1-tetradecylamine With acetic acid	74%

2-decyl-1-tetradecylamine (62281-07-6) + 5-bromo-2-iodobenzoyl chloride (293738-03-1) → 5-bromo-N-(2-decyltetradecyl)-2-iodobenzene

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 2.5h; Reflux;	70%

2-decyl-1-tetradecylamine (62281-07-6) + C5HBrClIOS → 5-bromo-N-(2-decyltetradecyl)-2-iodothiophene-3-carboxamide

Conditions	Yield
With pyridine at 0 - 20℃; for 3.5h;	68%

2-decyl-1-tetradecylamine (62281-07-6) + 3,3'dibromo-2,2'-bithiophene (51751-44-1) → N-(2-decyltetradecyl)-dithieno[3,2-b:2',3'-d]pyrrole (1207067-13-7)

Conditions	Yield
Stage #1: 3,3'dibromo-2,2'-bithiophene With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 0.333333h; Inert atmosphere; Stage #2: 2-decyl-1-tetradecylamine In toluene at 110℃; for 12h; Inert atmosphere;	62%

2-decyl-1-tetradecylamine (62281-07-6) + 4,5-dibromophthalic anhydride (65237-17-4) → 5,6-dibromo-2-(2-decyltetradecyl)isoindoline-1,3-dione (1402231-50-8)

Conditions	Yield
With acetic acid at 120℃; for 2h; Schlenk technique; Inert atmosphere;	60%

2-decyl-1-tetradecylamine (62281-07-6) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → 2-(2-decyltetradecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 1,4,5,8-naphthalenetetracarboxylic dianhydride In N,N-dimethyl-formamide for 25h; Inert atmosphere; Reflux; Stage #2: With 1,3,5-trichlorobenzene; urea for 2h; Reflux; Inert atmosphere;	58.3%

2-decyl-1-tetradecylamine (62281-07-6) + 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde (1015423-45-6) → 1,3-dibromo-5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde In tetrahydrofuran at 50℃; for 3h; Inert atmosphere; Stage #2: With thionyl chloride In tetrahydrofuran at 55℃; for 4h; Inert atmosphere;	58%

2-decyl-1-tetradecylamine (62281-07-6) + 3,6-dibromo-2,5-bis(3-bromothiophen-2-yl)thieno[3,2-b]thiophene (1392114-79-2) → C60H98N2S4

Conditions	Yield
Stage #1: 3,6-dibromo-2,5-bis(3-bromothiophen-2-yl)thieno[3,2-b]thiophene With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 25℃; for 0.333333h; Stage #2: 2-decyl-1-tetradecylamine In toluene at 110℃; for 10h;	56%

2-decyl-1-tetradecylamine (62281-07-6) + 2-(2'-(thiophen-2'''-yl)thiazol-5'-yl)-5-(2''-(thiophen-2''''-yl)thiazol-5''-yl)thieno[3,2-b]thiophene-3,4',6,4''-tetracarboxylic dianhydride → N,N'-bis(2-decyltetradecyl)[2-(2'-(thiophen-2'''-yl)thiazol-5'-yl)-5-(2''-(thiophen-2''''-yl)thiazol-5''-yl)thieno[3,2-b]thiophene-3,4',6,4''-bis(dicarboximide)]

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 2-(2'-(thiophen-2'''-yl)thiazol-5'-yl)-5-(2''-(thiophen-2''''-yl)thiazol-5''-yl)thieno[3,2-b]thiophene-3,4',6,4''-tetracarboxylic dianhydride In dichloromethane at 40℃; for 2h; Stage #2: With thionyl chloride for 2h; Reflux;	56%

2-decyl-1-tetradecylamine (62281-07-6) + 1,3-dibromo-11-(tert-butyl)quinoxalino[2',3':9,10]phenanthro[4,5-abc]phenazine (1445997-25-0) → 11-(tert-butyl)-N1,N3-bis(2-decyltetradecyl)quinoxalino[2',3':9,10]phenanthro[4,5-abc]phenazine-1,3-diamine

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 120℃; for 16h; Inert atmosphere;	51%

2-decyl-1-tetradecylamine (62281-07-6) + 4,7-bis((tert-butyldimethylsilyloxy)methyl)-2-octyl-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione (1224885-87-3) → 4,7-bis((tert-butyldimethylsilyloxy)methyl)-2-(2-decyltetradecyl)-3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione (1204696-03-6)

Conditions	Yield
In para-xylene; toluene Inert atmosphere; Reflux;	50%

2-decyl-1-tetradecylamine (62281-07-6) + 2,3-dibromomaleic anhydride (1122-12-9) → 3,4-dibromo-1-(2-decyltetradecyl)pyrrole-2,5-dione (1301741-17-2)

Conditions	Yield
With acetic acid for 16h; Reflux;	50%

2-decyl-1-tetradecylamine (62281-07-6) + 1,4-Cyclohexanedione (637-88-7) → N,N-bis(2-decyltetradecyl)benzene-1,4-diamine

Conditions	Yield
With air In ethanol for 2h;	46%
With air In ethanol Inert atmosphere;

2-decyl-1-tetradecylamine (62281-07-6) + C24H12O3 → C48H61NO2

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	45%

2-decyl-1-tetradecylamine (62281-07-6) + 6,6'-bis(thiophen-2-yl)-[2,2'-biazulene]-1,1',3,3'-tetracarboxylic dianhydride → N,N'-bis(2-decyltetradecyl)-6,6'-di(thiophen-2-yl)[2,2'-biazulene]-1,1',3,3'-tetracarboxdiimide

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 6,6'-bis(thiophen-2-yl)-[2,2'-biazulene]-1,1',3,3'-tetracarboxylic dianhydride In dichloromethane for 8h; Reflux; Stage #2: With sodium acetate; acetic anhydride at 80℃; for 6h;	42%

2-decyl-1-tetradecylamine (62281-07-6) + 2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride (83204-68-6) → N,N′-bis(2-decyl-1-tetradecyl)-2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid bisimide (1088205-04-2)

Conditions	Yield
With propionic acid at 140℃;	41.5%
In o-xylene; propionic acid at 140℃;	13.4%

2-decyl-1-tetradecylamine (62281-07-6) + 2,2'-(2,5-dibromo-1,4-phenylene)bis(3-bromothiophene) (1217503-06-4) → C62H104N2S2

Conditions	Yield
Stage #1: 2,2'-(2,5-dibromo-1,4-phenylene)bis(3-bromothiophene) With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 20℃; for 0.333333h; Buchwald-Hartwig Coupling; Stage #2: 2-decyl-1-tetradecylamine In toluene at 110℃; Buchwald-Hartwig Coupling;	40%

Upstream product

• 132004-78-5 toluene-4-sulfonic acid 2-decyl-1-tetradecyl ester 
• 58670-89-6 2-decylteradecanol 
• 732276-63-0 11-bromomethyl-tricosane 
• 135713-14-3 2-(2-decyltetradecyl)isoindoline-1,3-dione 

Downstream Products

• 1088205-04-2 N,N′-bis(2-decyl-1-tetradecyl)-2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid bisimide 
• 1369426-80-1 C₆₇H₈₆N₂O₄Si 
• 1369426-82-3 C₅₈H₆₆N₂O₄ 
• 1369426-75-4 C₅₆H₆₅IN₂O₄ 
• 909019-78-9 N,N-bis(2-decyl-1-tetradecyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide 
• 1257635-56-5 N,N'-di(2-decyltetradecyl)-[2,3-d:6,7-d']-bi[2-(1,3-dithiacyclopenten-2-ylidene)-2-phenyl acetonitrile]-naphthalene-1,4,5,8-tetracarboxylic acid diimide 

Relevant articles and documents

Synthesis of thienopyrrolodione-based copolymers and their application in organic thin-film transistors

Two thienopyrrolodione (TPD)-based polymers, 24DTT-TPD and 24DTS-TPD, were synthesized by carrying out Stille coupling reactions. The obtained polymers were characterized by 1H NMR, FT-IR, mass analysis, UV-visible spectroscopy, cyclic voltammetry, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). The deposited films were characterized by X-ray diffraction. Synthesized polymers showed good solubility in common solvents. The solution-processed organic field-effect transistors showed field-effect mobility values of 4.5 × 10-5 cm2/Vs for 24DTT-TPD and 2.9 × 10-2 cm2/Vs for 24 DTS-TPD at optimal conditions.

Thieno[3,4-c]pyrrole-4,6-dione-3,4-difluorothiophene Polymer Acceptors for Efficient All-Polymer Bulk Heterojunction Solar Cells

Branched-alkyl-substituted poly(thieno[3,4-c]pyrrole-4,6-dione-alt-3,4-difluorothiophene) (PTPD[2F]T) can be used as a polymer acceptor in bulk heterojunction (BHJ) solar cells with a low-band-gap polymer donor (PCE10) commonly used with fullerenes. The “all-polymer” BHJ devices made with PTPD[2F]T achieve efficiencies of up to 4.4 %. While, to date, most efficient polymer acceptors are based on perylenediimide or naphthalenediimide motifs, our study of PTPD[2F]T polymers shows that linear, all-thiophene systems with adequately substituted main chains can also be conducive to efficient BHJ solar cells with polymer donors.

Conjugated polymers from naphthalene bisimide

(Chemical Equation Presented) Stille coupling of regioisomerically pure dibromonaphthalene bisimides (NBI) with various stannylated thiophene-based monomers yields (very) high molecular weight donor-acceptor conjugated polymers. Electrochemical and optica