3937-56-2

Basic information

• Product Name: 1,9-Nonanediol
• Synonyms: NONAMETHYLENE GLYCOL;TIMTEC-BB SBB008482;alpha,OMEGA-Nonanediol;α,ω-nonanediol;1,9-NONANEDIOL;1,9-DIHYDROXYNONANE;nonane-1,9-diol;1,9-Nonanediol,97%
• CAS NO: 3937-56-2
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.25
• EINECS: 223-517-5
• Product Categories: alpha,omega-Alkanediols;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Linear hydrocarbon series;OLED materials,pharm chemical,electronic;Pyridines ,Halogenated Heterocycles
• Mol File: 3937-56-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 177 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Fused Crystalline Solid
• Density: 0.918
• Vapor Pressure: 0.000196mmHg at 25°C
• Refractive Index: 1.4571 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in methanol.
• PKA: 14.89±0.10(Predicted)
• Water Solubility: 5.7g/L at 20℃
• BRN: 1737531
• CAS DataBase Reference: 1,9-Nonanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-Nonanediol(3937-56-2)
• EPA Substance Registry System: 1,9-Nonanediol(3937-56-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 3937-56-2(Hazardous Substances Data)

Usage

Chemical Properties

white fused crystalline solid

Uses

1,9-Nonanediol is used in organic synthesis. It also can react with 3,4-dihydro-2H-pyran and 9-(tetrahydropyrane-2-yloxy)nonan-1-ol.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H20O2/c10-8-6-4-2-1-3-5-7-9-11/h10-11H,1-9H2

Synthetic route

9-hydroxynonyl-1-triphenylmethylether (82777-72-8) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
Stage #1: 9-hydroxynonyl-1-triphenylmethylether With n-butyllithium In hexane at 0℃; Stage #2: With naphthalene; lithium In tetrahydrofuran; hexane at 0 - 20℃; for 20h;	99%

1,9-di(trityloxy)nonane (634902-05-9) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran at -30℃; for 3.5h;	99%

9-(triphenylsilyloxy)-1-nonanol (109027-55-6) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 1h;	98%

9-<(2H-tetrahydropyran-2-yl)oxy>nonan-1-ol (98847-00-8) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With copper dichloride In methanol at 20℃; Hydrolysis;	95%
With CuCl2*2H2O In methanol at 20℃; for 1.25h;	95%

1,3-Dioxa-cyclododecane-4,12-dione → azelaic acid (123-99-9) + 1,9-Nonanediol (3937-56-2) + 9-hydroxynonanoic acid (3788-56-5)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 23℃; for 120h;	A n/a B 2% C 92%
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h;	A n/a B 6% C 87%

azelaic acid (123-99-9) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h; Reflux;	91%
With zirconium(IV) borohydride In tetrahydrofuran at 25℃; for 1h; Reduction;	90%
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	88%

1-[dimethyl(phenyl)silyloxy]-9-(triphenylsilyloxy)nonane (862249-29-4) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 3h;	79%

octadec-9-enoic acid methyl ester (112-62-9) → 1,9-Nonanediol (3937-56-2) + nonyl alcohol (143-08-8)

Conditions	Yield
With lithium aluminium tetrahydride multistep reaction, other substrates;	A 74% B 64%
With lithium aluminium tetrahydride 1) CH2Cl2; Yield given. Multistep reaction. Yields of byproduct given;
With lithium aluminium tetrahydride Yield given. Multistep reaction. Yields of byproduct given;
With lithium aluminium tetrahydride Yield given. Multistep reaction. Yields of byproduct given;

nona-1,8-diene (4900-30-5) → nonane-1,5-diol (13686-96-9) + 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide borane complex Product distribution;	A 71% B 15%

9-benzylsulfonyloxynonyl benzylsulfonate (61801-07-8) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at 0℃; for 2.5h;	67%

(Z)-6-nonenol (31502-19-9, 40709-05-5, 35854-86-5) → 1,9-Nonanediol (3937-56-2) + 1,7-nonanediol (4469-84-5) + 1,8-dihydroxynonane (61448-29-1) + nonyl alcohol (143-08-8)

Conditions	Yield
With acetylacetonatodicarbonylrhodium(l); 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); carbon monoxide; C70H72O2P2; hydrogen In 1,4-dioxane at 120℃; under 3750.38 Torr; for 36h; Inert atmosphere; Autoclave;	A 62% B n/a C n/a D 24 %Chromat.

Dimethyl azelate (1732-10-1) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With ethanol; sodium
With ethanol; sodium
With i-Amyl alcohol; sodium
With hydrogenchloride; cerium monofluoride; Triethoxysilane 1. 12 h, 25 deg C; 2. acetone, 30 min; Yield given. Multistep reaction;

Dimethyl azelate (1732-10-1) → 1,9-Nonanediol (3937-56-2) + 9-hydroxynonanoic acid (3788-56-5)

Conditions	Yield
With ethanol; sodium

diethyl azelate (624-17-9) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With ethanol; sodium
With copper chromite at 270℃; under 154457 Torr; Hydrogenation;
With i-Amyl alcohol; sodium

oleoyl alcohol (143-28-2) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
(i) O3, AcOEt, (ii) LiAlH4, Py; Multistep reaction;

undecanedioic acid diethyl ester (22543-29-9) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With sodium In ethanol

(Sp)-2,12-dioxa-1(1,4)-benzena-cyclododecaphane-12-carboxylic acid → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
(i) H2, Al2O3, Rh, AcOH, (ii) KOH, EtOH; Multistep reaction;

oxecan-2-one (6008-27-1) → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With lithium triethylborohydride In various solvent(s) for 0.416667h; Thermodynamic data; ΔH;

1-acetoxy-9-octadecene (136934-14-0) → 1,9-Nonanediol (3937-56-2) + nonyl alcohol (143-08-8)

Conditions	Yield
With lithium aluminium tetrahydride 1) CH2Cl2; Yield given. Multistep reaction. Yields of byproduct given;

(E)-Octadec-15-ene-1,9,10,13-tetraol → 1,9-Nonanediol (3937-56-2) + (E)-Non-6-ene-1,4-diol

Conditions	Yield
With sodium tetrahydroborate; periodic acid 1.) ether, 1 h, 2.) overnight; Multistep reaction;

azelaic acid amide → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With pentan-1-ol; sodium

diethyl azelate (624-17-9) + barium oxide + copper oxide-chromium oxide → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
at 300℃; under 198587 Torr; Hydrogenation;

pentan-1-ol (71-41-0) + 1,7-heptanedicarboxamide (1842-72-4) + sodium → 1,9-Nonanediol (3937-56-2)

Dimethyl azelate (1732-10-1) + ethanol (64-17-5) + sodium → 1,9-Nonanediol (3937-56-2) + 9-hydroxynonanoic acid (3788-56-5)

diethyl azelate (624-17-9) + barium oxide + copper oxide-chromium oxide → nonane (111-84-2) + 1,9-Nonanediol (3937-56-2) + nonyl alcohol (143-08-8)

Conditions	Yield
at 400℃; under 198587 Torr; Hydrogenation;

nona-1,8-diene (4900-30-5) → 1,9-Nonanediol (3937-56-2) + non-8-en-1-ol (13038-21-6) + non-7-en-1-ol (63768-13-8) + nonyl alcohol (143-08-8)

Conditions	Yield
Stage #1: nona-1,8-diene With triisobutylaluminum; bis-triphenylphosphine-palladium(II) chloride In dichloromethane at 25℃; for 12h; Stage #2: With sodium hydroxide; oxygen In dichloromethane	A 14 % Spectr. B 12 % Spectr. C 24 % Spectr. D 25 % Spectr.

benzyl 9-(allyloxycarbonyl)-1-nonyl carbonate → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With naphthalen-1-yl-lithium In tetrahydrofuran at 0℃; for 2h;

9-(2,2-dimethylpropanoyloxy)nonyl pivalate → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
With naphthalene; lithium In tetrahydrofuran at 0℃; for 1h;	99 % Chromat.

9-Trimethylsilanyloxy-9-[3-((E)-2-trimethylsilanyloxy-hept-4-enyl)-oxiranyl]-nonanoic acid methyl ester → 1,9-Nonanediol (3937-56-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran / Heating 2: 1.) H5IO6, 2.) NaBH4 / 1.) ether, 1 h, 2.) overnight View Scheme

1,9-Nonanediol (3937-56-2) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With carbon tetrabromide; Cu(tmp)(BINAP)BF4; sodium bromide In N,N-dimethyl-formamide for 24h; Appel Halogenation; UV-irradiation; Inert atmosphere;	99%
With water; hydrogen bromide
With hydrogen bromide

1,9-Nonanediol (3937-56-2) → 1,9-nonanedioldiisopropyl ether (200499-47-4)

Conditions	Yield
With hydrogen; Pd-C In acetone	99%

1,9-Nonanediol (3937-56-2) + p-toluenesulfonyl chloride (98-59-9) → nonane-1,9-diyl bis(4-methylbenzenesulfonate) (73992-42-4)

Conditions	Yield
With pyridine In dichloromethane at 5 - 15℃; for 0.333333h;	98.6%
With pyridine at 0℃; for 2.5h;	88%
With trimethylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 1h;	85%

1,9-Nonanediol (3937-56-2) + trityl chloride (76-83-5) → 9-hydroxynonyl-1-triphenylmethylether (82777-72-8)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide	98%
With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 12h;	43%
With pyridine at 0 - 20℃; for 16.5h;

1,9-Nonanediol (3937-56-2) + acetic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester (721448-82-4) → acetic acid 4-{9-[1-acetoxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-4-yloxy]-nonyloxy}-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;	98%

1,9-Nonanediol (3937-56-2) → 1,9-dichlorononane (821-99-8)

Conditions	Yield
With Ethyl trichloroacetate; triphenylphosphine In acetonitrile at 10 - 15℃; for 3h;	97%
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide	65%
With pyridine; thionyl chloride
With thionyl chloride

3,4-dihydro-2H-pyran (110-87-2) + 1,9-Nonanediol (3937-56-2) → 9-<(2H-tetrahydropyran-2-yl)oxy>nonan-1-ol (98847-00-8)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate In hexane for 0.0333333h; Microwave irradiation;	97%
With tin(ll) chloride In chloroform for 24h; Ambient temperature;	80%
With toluene-4-sulfonic acid In dichloromethane for 1.5h;	60%

1,9-Nonanediol (3937-56-2) → 9-bromononan-1-ol (55362-80-6)

Conditions	Yield
With hydrogen bromide In toluene for 7.5h; Time; Reflux;	95%
With hydrogen bromide In toluene for 30h; Dean-Stark; Reflux;	94%
With hydrogen bromide In n-heptane at 150℃;	93%

1,9-Nonanediol (3937-56-2) + p-Methoxybenzyl bromide (2746-25-0) → 9-((4-methoxybenzyl)oxy)nonan-1-ol (267005-80-1)

Conditions	Yield
With sodium hydride; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	95%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	95%
With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 1h;	90%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h;	76%

1,9-Nonanediol (3937-56-2) → 9-iodononan-1-ol (76334-30-0)

Conditions	Yield
With iodine In acetonitrile at 120℃; for 0.0666667h; Microwave irradiation; chemoselective reaction;	93%
Multi-step reaction with 2 steps 1: 47percent HBr / toluene / Heating 2: NaI / acetone / Ambient temperature View Scheme

1,9-Nonanediol (3937-56-2) + acetic acid (64-19-7) → 9-hydroxyl nonanyl acetate (103109-24-6)

Conditions	Yield
With HY-Zeolite In chloroform for 3.5h; Heating;	92%
With sulfuric acid In hexane; cyclohexane; water for 36h; Heating;	90%
	82%
With sulfuric acid In water	56%

1,9-Nonanediol (3937-56-2) → nonanedial (51651-40-2)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 0.583333h;	92%
With 2,6-dimethylpyridine; silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 48h;	83%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 2h; Heating;	77%

1,9-Nonanediol (3937-56-2) + 3-vinylbenzoic acid (28447-20-3) → nonane-1,9-diyl bis(3-vinylbenzoate)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; Steglich Esterification; Inert atmosphere;	92%

1,9-Nonanediol (3937-56-2) + acetophenone (98-86-2) → C25H32O2 (116223-42-8)

Conditions	Yield
With potassium hydroxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine at 100℃; for 15h; Inert atmosphere;	91%

1,9-Nonanediol (3937-56-2) + methyl 5-(chlorocarbonyl)furan-2-carboxylate → 2-(9-hydroxynonyl) 5-methyl furan-2,5-dicarboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine In tetrahydrofuran at 25℃; for 10h;	91%
With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine In tetrahydrofuran at 20℃;

1,9-Nonanediol (3937-56-2) → 9-bromononanal (124388-97-2)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 60℃;	90%
Multi-step reaction with 2 steps 1: 7.8 g / HBr / benzene / 24 h / Heating 2: 7.18 g / PCC / CH2Cl2 / 0.5 h View Scheme
Multi-step reaction with 2 steps 1: 60 percent / 48percent HBr / toluene; H2O / 48 h / 90 - 95 °C 2: 85 percent / pyridiniumchlorochromate, MgSO4 / CH2Cl2 / 1.5 h View Scheme
Multi-step reaction with 2 steps 1: HBr / benzene 2: 60 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h / Ambient temperature View Scheme

(Z)-9-octadecenoyl chloride (112-77-6) + 1,9-Nonanediol (3937-56-2) → 6-[(Z)-octadec-9-enoyl]oxynonyl-(Z)-octadec-9-enoate (1494679-01-4)

Conditions	Yield
With pyridine In chloroform at 20℃; Inert atmosphere;	90%

1,9-Nonanediol (3937-56-2) + 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (131986-28-2) → 1,9-bis[3-(pyrid-3-yl)-1,2,5-thiadiazol-4-yloxy]nonane (274688-26-5)

Conditions	Yield
Stage #1: 1,9-Nonanediol With sodium hydride In tetrahydrofuran Stage #2: 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine In tetrahydrofuran for 20h; Heating; Further stages.;	88%
With sodium hydride In tetrahydrofuran Substitution; Heating;

1,9-Nonanediol (3937-56-2) + aniline (62-53-3) → N,N'-diphenyl-nonanediyldiamine

Conditions	Yield
With Pt-Sn/γ-Al2O3 In o-xylene at 145℃; for 24h; Inert atmosphere;	88%

1,9-Nonanediol (3937-56-2) + p-methoxybenzyl chloride (824-94-2) → 9-((4-methoxybenzyl)oxy)nonan-1-ol (267005-80-1)

Conditions	Yield
Stage #1: 1,9-Nonanediol With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0℃; for 1h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0 - 20℃; for 18.5h;	84%
Stage #1: 1,9-Nonanediol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 23℃; Inert atmosphere;	83%
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 12h;	71%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; mineral oil at 0 - 60℃; Inert atmosphere;	46%

1,9-Nonanediol (3937-56-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 9-((tert-butyldimethylsilyl)oxy)nonan-1-ol (157730-99-9)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 20℃; for 3h;	83%
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 65.67h;	83%
Stage #1: 1,9-Nonanediol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Schlenk technique; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0℃; for 2h; Inert atmosphere; Schlenk technique;	73%

1,9-Nonanediol (3937-56-2) + (S)-(-)-3,3,3-Trifluormilchsaeure (125995-00-8) → 1,9-nonanediol mono-(S)-3,3,3-trifluorolactate

Conditions	Yield
With sulfuric acid In toluene Heating;	82%

1,9-Nonanediol (3937-56-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 9-(tert-butyldiphenylsilyloxy)-nonan-1-ol (139258-85-8) + 1,9-di-(tert-butyldiphenylsilyloxy)-nonane

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 28h; Substitution;	A 81% B 8.5%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 40h;	A 55% B 25%

1,9-Nonanediol (3937-56-2) + ethyl acetate (141-78-6) → 9-hydroxyl nonanyl acetate (103109-24-6)

Conditions	Yield
With HY-Zeolite for 6h; Heating;	81%

Upstream product

• 6008-27-1 oxecan-2-one 
• 1732-10-1 Dimethyl azelate 
• 64-17-5 ethanol 
• 31502-19-9 (Z)-6-nonenol 
• 533-87-9 9,10,16-trihydroxyhexadecanoic acid 
• 2553-17-5 azelaic acid semialdehyde 
• 111-84-2 nonane 
• 112-80-1 cis-Octadecenoic acid 
• 143-08-8 nonyl alcohol 
• 24829-11-6 1,5-bisoxiranyl-pentane 
• 1675-69-0 nonanedinitrile 
• 4549-31-9 1,7-dibromoheptane 
• 1852-04-6 undecanedioic acid 
• 61801-07-8 9-benzylsulfonyloxynonyl benzylsulfonate 

Downstream Products

• 4944-60-9 1,9-nonanediol diacetate 
• 104876-10-0 9-(phenylmethoxy)nonan-1-ol 
• 119-61-9 benzophenone 
• 91491-75-7 9-[(9-Hydroxy-nonyloxy)-diphenyl-methoxy]-nonan-1-ol 
• 91491-67-7 2,2,14,14-tetraphenyl-1,3,13,15-tetraoxacyclotetracosane 
• 700865-88-9 9-((E)-3-Phenyl-allyloxy)-nonan-1-ol 
• 267005-80-1 9-(4-methoxybenzyloxy)nonan-1-ol 
• 140434-48-6 benzoic acid 9-hydroxynon-1-yl ester 
• 219833-52-0 NbO⁽³⁺⁾*PO₄^(3-)*OH(CH₂)9OH=NbOPO₄*OH(CH₂)9OH 
• 190262-27-2 VO⁽³⁺⁾*PO₄^(3-)*HO(CH₂)9OH=VOPO₄*HO(CH₂)9OH 
• 82777-72-8 9-hydroxynonyl-1-triphenylmethylether 
• 634902-05-9 1,9-di(trityloxy)nonane 
• 139258-85-8 9-(tert-butyldiphenylsilyloxy)-nonan-1-ol 
• 4549-33-1 1,9-Dibromononane 

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