67000-89-9

Basic information

• Product Name: 1-PYRENEBUTANOL
• Synonyms: 4-(1-PYRENYL)-N-BUTANOL;1-PYRENEBUTANOL;4-(1-Pyrenyl)-1-butanol;4-(pyren-1-yl)butan-1-ol;1-Pyrenebutanol 99%;1-pyrenees butanol
• CAS NO: 67000-89-9
• Molecular Formula: C₂₀H₁₈O
• Molecular Weight: 274.36
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 67000-89-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 80-83 °C(lit.)
• Boiling Point: 488.4 °C at 760 mmHg
• Flash Point: 205.4 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 2.37E-10mmHg at 25°C
• Refractive Index: 1.761
• PKA: 15.15±0.10(Predicted)
• CAS DataBase Reference: 1-PYRENEBUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PYRENEBUTANOL(67000-89-9)
• EPA Substance Registry System: 1-PYRENEBUTANOL(67000-89-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 67000-89-9(Hazardous Substances Data)

Usage

Uses

1-Pyrenebutanol is a interfacial agent for bisphenol-A polycarbonate and multi-walled carbon nanotube composites.

General Description

1-Pyrenebutanol, an alcohol, is an organic building block. It participates in the polymerization of cyclic esters (lactide, δ-valerolactone and ε-caprolactone).

InChI:InChI=1/C20H18O/c21-13-2-1-4-14-7-8-17-10-9-15-5-3-6-16-11-12-18(14)20(17)19(15)16/h3,5-12,21H,1-2,4,13H2

Synthetic route

4-(1-pyrene)butyric acid methyl ester (70570-29-5) → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;

1-pyrenebutyric acid (3443-45-6) → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
With lithium aluminium tetrahydride	95%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;	90.2%
With borane-THF In tetrahydrofuran at 20℃; Cooling with ice;	79%

4-(1-pyrene)butanoic acid ethyl ester (59275-39-7) → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h;	88%

C20H18O(2-)*2Li(1+) → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) methanol, -78 deg C, 2.) abs. toluene, reflux, 1h.; Yield given. Multistep reaction;

2,2-dibromo-malonic acid bis-(4-pyren-1-yl-butyl) ester → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide	100 % Chromat.

pyrene (129-00-0) → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) lithium wire / 1.)-78 deg C, 12 h., 2.) room temp., 12 h. 2: 2.) DDQ / 1.) methanol, -78 deg C, 2.) abs. toluene, reflux, 1h. View Scheme
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / nitrobenzene / 18 h / 0 - 20 °C 2.1: potassium hydroxide; hydrazine / diethylene glycol / 2 h / Heating / reflux 2.2: 0 °C 3.1: thionyl chloride / 0 - 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C View Scheme

C53H48O5S2 (1452863-03-4) + Hg(2+) → bis(acetic acid thiolato)mercury(II) + 4-pyrenylbutanol (67000-89-9) + 4-ethoxybenzaldehyde (10031-82-0)

Conditions	Yield
In acetonitrile for 0.166667h; pH=4.8;

γ-oxo-1-pyrenebutyric acid (7499-60-7) → 4-pyrenylbutanol (67000-89-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium hydroxide; hydrazine / diethylene glycol / 2 h / Heating / reflux 1.2: 0 °C 2.1: thionyl chloride / 0 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C View Scheme

11-(tert-butoxycarbonylamino)undecanoic acid (10436-25-6) + 4-pyrenylbutanol (67000-89-9) → C36H47NO4 (1416547-75-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 120h;	99%

4-pyrenylbutanol (67000-89-9) + methanesulfonyl chloride (124-63-0) → 4-(pyren-1-yl)butyl methanesulfonate (205488-04-6)

Conditions	Yield
With triethylamine In dichloromethane Cooling with ice;	98%
With triethylamine In dichloromethane at 0℃; for 12h;	96%
With triethylamine In dichloromethane Cooling with ice;	91.2%
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	91%
With triethylamine In dichloromethane at 20℃; for 4h;

4-pyrenylbutanol (67000-89-9) → 4-(pyren-1-yl)butanal

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;	97%
With dipyridinium dichromate In dichloromethane at 20℃; Inert atmosphere;	97%
With pyridinium chlorochromate In dichloromethane at 20℃;	95%

4-pyrenylbutanol (67000-89-9) → 1-bromo-4-(1-pyrenyl)butane (117846-05-6)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In acetonitrile at 25℃; for 0.333333h; Appel Halogenation;	96%
With carbon tetrabromide; triphenylphosphine In dichloromethane Bromination; substitution;	90%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran	90%

4-pyrenylbutanol (67000-89-9) + 4-cyano-4-(thiobenzoylthio)pentanoic acid (201611-92-9) → 4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 4-pyren-1-yl-butyl ester (1048735-14-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 0 - 20℃;	95%

4-pyrenylbutanol (67000-89-9) + 2-Bromoacetyl bromide (598-21-0) → C22H19BrO2

Conditions	Yield
Stage #1: 4-pyrenylbutanol In dichloromethane Alkaline conditions; Cooling with ice; Stage #2: 2-Bromoacetyl bromide In dichloromethane at 20℃; for 24h; Cooling with ice;	92%

11-mercaptounadecanoic acid (71310-21-9) + 4-pyrenylbutanol (67000-89-9) → 4-(pyren-4-yl) butyl-11-mercaptoundecanoate

Conditions	Yield
With hafnium/THF In toluene for 48h; Reflux; Molecular sieve;	89%

2,4,6-tri(4-pyridyl)-1,3,5-triazine (42333-78-8) + [Ru2(η6-p-cymene)2(C6H2O4)Cl2] (1039768-31-4) + 4-pyrenylbutanol (67000-89-9) + silver trifluoromethanesulfonate (2923-28-6) → [(1-pyrenebutanol)*Ru6(p-cymene)6(2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)2(2,5-dioxydo-1,4-benzoquinonato)3](triflate)6

Conditions	Yield
In methanol byproducts: AgCl; Ru complex and AgCF3SO3 stirred in MeOH for 2 h; filtered into suspn. ofN3C3(C5H4N)3 and pyrenyl in MeOH; stirred at room temp. for 18 h; solvent removed under reduced pressure; dissolved in CH2Cl2; filtered; vol. of filtrate reduced; pptd. with Et2O; collected by filtration;	88%

2-bromoisobutyric acid bromide (20769-85-1) + 4-pyrenylbutanol (67000-89-9) → C24H23BrO2

Conditions	Yield
With triethylamine In dichloromethane	88%

4-pyrenylbutanol (67000-89-9) + 3-oxo-3-(pent-4-yn-1-yloxy)propanoic acid (1448599-87-8) → pent-4-yn-1-yl (4-(pyren-1-yl)butyl) malonate (1448599-89-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h; Cooling with ice; Inert atmosphere;	87%

4-pyrenylbutanol (67000-89-9) + O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-glucopyranosyl)trichloracetimidat (94715-74-9) → 4-(1-pyrenyl)butyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (1160291-41-7)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 3h;	85%

4-pyrenylbutanol (67000-89-9) + N-tert-butyl-O-[1-(4-chloromethyl-phenyl)-ethyl]-N-(2-methyl-1-phenyl-propyl)-hydroxylamine (227000-85-3) → N-tert-butyl-N-(2-methyl-1-phenyl-propyl)-O-{1-[4-(4-pyren-1-yl-butoxymethyl)-phenyl]-ethyl}-hydroxylamine

Conditions	Yield
With sodium hydride In tetrahydrofuran for 16h; Heating;	84%

4-pyrenylbutanol (67000-89-9) + malonoyl dichloride (1663-67-8) → bis[4-pyrene-1-butoxy]malonyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 24h;	84%

3,3'-dithiobis(propionic acid) (1119-62-6) + 4-pyrenylbutanol (67000-89-9) → 3-((3-oxo-3-(4-(pyren-1-yl)butoxy)propyl)disulfanyl)propanoic acid (1259437-62-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20h;	81.3%

4-pyrenylbutanol (67000-89-9) + propargyl bromide (106-96-7) → 1-(4-(prop-2-yn-1-yloxy)butyl)pyrene (1211548-30-9)

Conditions	Yield
Stage #1: 4-pyrenylbutanol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran; toluene at 0℃; Inert atmosphere; Reflux; Darkness;	81%
Stage #1: 4-pyrenylbutanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; Darkness;	69%

4-pyrenylbutanol (67000-89-9) + Methacryloyl chloride (920-46-7) → 4-(pyren-1-yl)butyl methacrylate (71254-27-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	80%
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 0℃; for 2h;

thionyl chloride (7719-09-7) + [(C5H5)TiCl(C5H4C(CH3)2CH2CO2)]*0.5C7H8 + 4-pyrenylbutanol (67000-89-9) → [(C5H5)TiCl2(C5H4C(CH3)2CH2C(O)O(CH2)4C16H9)] (864767-17-9)

Conditions	Yield
With NaH In dichloromethane Ti complex was reacted with SOCl2 at room temp. for 1 h; heated at 50°C for 2 h in vac.; dissolved in CH2Cl2; transferred to mixt. of NaHand alcohol in CH2Cl2; stirred at room temp. for 16 h; filtered through Celite; crystd. (CH2Cl2/pentane);	79%

4-pyrenylbutanol (67000-89-9) + 1,10-dibromodecane (4101-68-2) → 1-[4-(10-bromo-decyloxy)-butyl]-pyrene (244013-58-9)

Conditions	Yield
Stage #1: 4-pyrenylbutanol With potassium tert-butylate In toluene at 100℃; for 1h; Stage #2: 1,10-dibromodecane In toluene for 16h;	79%

3-Thiophene carboxylic acid (88-13-1) + 4-pyrenylbutanol (67000-89-9) → 4-(pyren-1-yl)butyl thiophene-3-carboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12.5h; Inert atmosphere;	79%

thiophen-3-yl-acetic acid (6964-21-2) + 4-pyrenylbutanol (67000-89-9) → 4-(pyren-1-yl)butyl 2-(thiophen-3-yl)acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12.5h; Inert atmosphere;	76%

4-pyrenylbutanol (67000-89-9) + 3-mercaptopropionic acid (107-96-0) → 4-(pyren-1-yl)butyl 3-mercaptopropionate (1041403-51-3)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Inert atmosphere; Reflux;	75%

4-pentynoic acid (6089-09-4) + 4-pyrenylbutanol (67000-89-9) → 4-(pyren-1-yl)butyl pent-4-ynoate (1213789-09-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	72%

4-pyrenylbutanol (67000-89-9) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Boc-Phe-Pyrene (1400924-49-3)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; ethyl cyanoglyoxylate-2-oxime In N,N-dimethyl-formamide at 0℃; for 2h;	71%

4-pyrenylbutanol (67000-89-9) + 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid (600727-96-6) → 2,6-d-pyrazol-1-yl-isonicotinic acid 4-pyren-1-yl-butyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere; Schlenk technique;	69%

2,6-bis-(bromomethyl)pyridine (7703-74-4) + 4-pyrenylbutanol (67000-89-9) → 2-(bromomethyl)-6-((4-(pyren-1-yl)butoxy)methyl)pyridine

Conditions	Yield
Stage #1: 4-pyrenylbutanol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 2,6-bis-(bromomethyl)pyridine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	68%
With sodium hydride In tetrahydrofuran; mineral oil for 18h; Reflux; Inert atmosphere;	62%

4-pyrenylbutanol (67000-89-9) + allyl bromide (106-95-6) → C23H22O

Conditions	Yield
With potassium hydride In dichloromethane at 0 - 20℃; for 6h;	62%

4-pyrenylbutanol (67000-89-9) + C13H16O5S2 (1452863-02-3) → C53H48O5S2 (1452863-03-4)

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℃; for 4h;	60%

Upstream product

• 70570-29-5 4-(1-pyrene)butyric acid methyl ester 
• 129-00-0 pyrene 
• 59275-39-7 4-(1-pyrene)butanoic acid ethyl ester 
• 3443-45-6 1-pyrenebutyric acid 
• 1452863-03-4 C₅₃H₄₈O₅S₂ 
• 7499-60-7 γ-oxo-1-pyrenebutyric acid 

Downstream Products

• 1046785-02-7 4-(4-{3,3,4,4,5,5-hexafluoro-2-[2-methyl-5-(4-octyloxyphenyl)thiophen-3-yl]cyclopent-1-enyl}-5-methylthiophen-2-yl)benzoic acid 4-(pyren-1-yl)butyl ester 
• 1048735-14-3 4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 4-pyren-1-yl-butyl ester 
• 1268714-77-7 C₈₀H₇₈N₄O₆P⁽¹⁺⁾*Cl^(1-) 
• 1400924-49-3 Boc-Phe-Pyrene 
• 1416547-73-3 C₄₇H₅₂N₂O₄ 
• 1452863-03-4 C₅₃H₄₈O₅S₂ 
• 205488-15-9 4‐(1‐pyrenyl)butanamine 

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