56578-18-8

Basic information

• Product Name: TRANS-5-DECEN-1-OL
• Synonyms: (E)-5-DECEN-1-OL;trans-5-Decen-1-ol,96%;trans-5-Decen-1-ol,95%;(5E)-decen-1-ol;5-(E)-decen-1-ol;5E-decen-1-ol;trans-5-Decen-1-ol;(5E)-5-Decen-1-ol
• CAS NO: 56578-18-8
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.27
• EINECS: 260-267-6
• Product Categories: insect pheromone
• Mol File: 56578-18-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: -4.05°C (estimate)
• Boiling Point: 113-118 °C11 mm Hg(lit.)
• Flash Point: 144 °F
• Appearance: clear colourless liquid
• Density: 0.85
• Vapor Pressure: 0.0173mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 2-8°C
• PKA: 15.15±0.10(Predicted)
• BRN: 1840630
• CAS DataBase Reference: TRANS-5-DECEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-5-DECEN-1-OL(56578-18-8)
• EPA Substance Registry System: TRANS-5-DECEN-1-OL(56578-18-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 24/25-37/39-36-26
• WGK Germany: 3
• RTECS: HE2096000
• TSCA: Yes
• Hazardous Substances Data: 56578-18-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless liquid

Uses

trans-5-Decen-1-ol is an isomer of?cis-4-Decen-1-ol (D225630), which is a reactant in the synthesis of epoxyisoprostanes as antiinflammatory agents.?trans-5-Decen-1-ol is also a useful reagent to synthesize indenyl tris(N-pyrrolyl)phosphine ruthenium complexes.

InChI:InChI=1/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h5-6,11H,2-4,7-10H2,1H3/b6-5+

Synthetic route

(5R,6R)-6-(Diphenyl-phosphinoyl)-decane-1,5-diol (89625-08-1, 89625-10-5, 115693-87-3, 115693-88-4) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	96%
	96%

(5RS,6RS) 6-diphenylphosphinoyldecane-1,5-diol → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 2h;	95.9%

dec-5-yn-1-ol (68274-97-5) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With ammonia; sodium In diethyl ether at -35℃; for 15h;	95%
With lithium aluminium tetrahydride In diethylene glycol dimethyl ether for 14h; Reflux;	94%
With lithium aluminium tetrahydride In diethylene glycol dimethyl ether for 14h; Inert atmosphere; Reflux;	93%

dec-5-yn-1-ol (68274-97-5) → (Z)-dec-5-en-1-ol (51652-47-2) + (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With dihydridotetrakis(triphenylphosphine)ruthenium; hydrogen In ethanol at 20℃; for 36h; optical yield given as %de; stereoselective reaction;	A 91% B n/a

10-Tetrahydropyranyloxy-dec-5(E)-ene (77441-49-7) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
hydrogenchloride In methanol for 4h;	90%

trans-5-decenal (21662-11-3) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With lithium aluminium tetrahydride; sodium hydroxide In diethyl ether; water for 5h; Solvent; Reagent/catalyst; Cooling with ice;	88%

(E)-dec-5-enoic acid (16424-55-8) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;	83%

pentan-1-ol (71-41-0) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With hydrogen bromide; sodium methylate; triphenylphosphine In water	80%

dec-5-yn-1-yl acetate (64275-65-6) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethylene glycol dimethyl ether Heating;

formaldehyd (50-00-0) + (E)-4-nonen-1-yl bromide (16695-35-5) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With magnesium In diethyl ether

5-hydroxypentanal (4221-03-8) + pentylidenetriphenylphosphorane (29541-98-8, 55317-64-1) → (Z)-dec-5-en-1-ol (51652-47-2) + (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With sodium ethanolate In toluene at 25℃; for 2h; Yield given. Yields of byproduct given;
With n-butyllithium In toluene at 25℃; for 2h; Yield given. Yields of byproduct given;

(E)-1,5-Decadien (79837-89-1) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1) THF, room temp., 1 h; Multistep reaction;
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1) 2h, THF; 2) 0 deg C; 3) 50 deg C; Yield given. Multistep reaction;

1-(tert-Butyl-diphenyl-silanyloxy)-5-trimethylsilanyl-decan-4-one → (Z)-dec-5-en-1-ol (51652-47-2) + (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

Methyl 5(E)-decenoate (84168-29-6) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;

5-Decyn-1-yl tert-butyldimethylsilyl ether (139224-13-8) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With hydrogen fluoride; ammonia; sodium 1) THF, -33 deg C, 10 h, 2) MeCN, r.t., 12 h; Yield given. Multistep reaction;
With ammonia; sodium In tetrahydrofuran for 2h; Heating;

1-(tert-Butyl-dimethyl-silanyloxy)-6-triethylsilanyl-decan-5-ol (152841-73-1) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With boron trifluoride diethyl etherate

(E)-4-nonen-1-yl bromide (16695-35-5) + paraformaldehyde → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
With magnesium 1.) THF, 30 deg C, 4 h 2.) 0 deg C, 2 h; Yield given. Multistep reaction;

5-hydroxypentanal (4221-03-8) + pentyltriphenylphosphonium bromide (21406-61-1) → (Z)-dec-5-en-1-ol (51652-47-2) + (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Stage #1: pentyltriphenylphosphonium bromide With potassium tert-butylate In toluene Dehydrobromination; Heating; Stage #2: 5-hydroxypentanal In toluene at 25℃; for 2h; Wittig reaction;

(E)-4-none-1-ol (16695-34-4) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / triphenylphosphine bromine / acetonitrile / 1 h / Heating 2: Mg / diethyl ether View Scheme
Multi-step reaction with 3 steps 1: 78 percent / pyridinium chlorochromate / CH2Cl2 / 2 h 2: 54 percent 3: 1) 9-BBN; 2) 6N NaOH, 30percent H2O2 / 1) 2h, THF; 2) 0 deg C; 3) 50 deg C View Scheme
Multi-step reaction with 2 steps 1: 83 percent / bromine, triphenylphosphine / CH2Cl2 / 0 °C / 1.) 0 deg C, 1 h 2.) room temp., 1 h 2: 1.) Mg / 1.) THF, 30 deg C, 4 h 2.) 0 deg C, 2 h View Scheme

(E)-4-nonenoic acid (35329-50-1) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 12.6 g / LiAlH4 / diethyl ether / 3 h / Heating 2: 85 percent / triphenylphosphine bromine / acetonitrile / 1 h / Heating 3: Mg / diethyl ether View Scheme

(E)-3-octene-1,1-dicarboxylic acid (35349-81-6) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 64 percent / 150 - 160 °C 2: 12.6 g / LiAlH4 / diethyl ether / 3 h / Heating 3: 85 percent / triphenylphosphine bromine / acetonitrile / 1 h / Heating 4: Mg / diethyl ether View Scheme

dimethyl (E)-3-octene-1,1-dicarboxylate (74962-53-1) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: KOH / methanol; H2O / Heating 2: 64 percent / 150 - 160 °C 3: 12.6 g / LiAlH4 / diethyl ether / 3 h / Heating 4: 85 percent / triphenylphosphine bromine / acetonitrile / 1 h / Heating 5: Mg / diethyl ether View Scheme

1-chloro-3-iodoheptane (74962-48-4) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: dimethyl malonate, Na, methanol / 3 h / Heating 2: KOH / methanol; H2O / Heating 3: 64 percent / 150 - 160 °C 4: 12.6 g / LiAlH4 / diethyl ether / 3 h / Heating 5: 85 percent / triphenylphosphine bromine / acetonitrile / 1 h / Heating 6: Mg / diethyl ether View Scheme
Multi-step reaction with 6 steps 1: 1.) Na, methanol / 1.) reflux, 2.) methanol, reflux, 3 h 2: KOH / methanol; H2O / Heating 3: 64 percent / 150 - 160 °C 4: 12.6 g / LiAlH4 / diethyl ether / 3 h / Heating 5: 85 percent / triphenylphosphine bromine / acetonitrile / 1 h / Heating 6: Mg / diethyl ether View Scheme

2-Triethylsilanyl-hexan-1-ol (152841-71-9) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: (COCl)2, Et3N / dimethylsulfoxide; CH2Cl2 2: diethyl ether / -78 °C 3: BF3*OEt2 View Scheme

2-Triethylsilanyl-hexanal (152841-67-3) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / -78 °C 2: BF3*OEt2 View Scheme

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86.3 percent / butyllithium / tetrahydrofuran; hexane / 0 °C 2: 67.6 percent / sodium borohydride / ethanol 3: 95.9 percent / sodium hydride / dimethylformamide / 2 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 1) BuLi 2: 68 percent / NaBH4 3: 96 percent / NaH / dimethylformamide View Scheme

(n-pentyl)diphenylphosphane oxide (88533-60-2) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86.3 percent / butyllithium / tetrahydrofuran; hexane / 0 °C 2: 67.6 percent / sodium borohydride / ethanol 3: 95.9 percent / sodium hydride / dimethylformamide / 2 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 1) BuLi 2: 68 percent / NaBH4 3: 96 percent / NaH / dimethylformamide View Scheme

6-diphenylphosphinoyl-1-hydroxydecan-5-one (89625-06-9) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67.6 percent / sodium borohydride / ethanol 2: 95.9 percent / sodium hydride / dimethylformamide / 2 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 68 percent / NaBH4 2: 96 percent View Scheme
Multi-step reaction with 2 steps 1: 68 percent / NaBH4 2: 96 percent / NaH / dimethylformamide View Scheme

E-1,6-undecadiene (71309-05-2) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O / 20 °C 2: NaOBr, NaOH / dioxane; H2O / 4 h / 0 °C 3: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

2-keto-E-6-undecene (96288-50-5) → (E)-5-decen-1-ol (56578-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOBr, NaOH / dioxane; H2O / 4 h / 0 °C 2: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

(E)-5-decen-1-ol (56578-18-8) + methanesulfonyl chloride (124-63-0) → (5E)-dec-5-en-1-yl methanesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In tetrahydrofuran

(E)-5-decen-1-ol (56578-18-8) + acetic anhydride (108-24-7) → (E)-5-decen-1-yl acetate (38421-90-8)

Conditions	Yield
With dmap at 100℃; for 2h;	98%
With pyridine for 24h; Ambient temperature;	96%
With triethylamine In dichloromethane for 5h; Solvent; Cooling with ice;	89%
With triethylamine In dichloromethane at 0 - 20℃; for 8h; Inert atmosphere; Schlenk technique;	85%
In pyridine at 25℃; for 24h;

(E)-5-decen-1-ol (56578-18-8) → trans-5-decenal (21662-11-3)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 5.5h; Reflux;	97%
With Dess-Martin periodane In dichloromethane at 20℃; for 6h; Schlenk technique; Inert atmosphere;	85%
With pyridinium chlorochromate In dichloromethane for 2h;

(E)-5-decen-1-ol (56578-18-8) → 1-Decanol (112-30-1)

Conditions	Yield
With hydrogen; TMSB; palladium In ethanol at 20℃; under 760 Torr; for 20h;	95%

(E)-5-decen-1-ol (56578-18-8) + n-tetradecanoic acid (544-63-8) → (E)-dec-5-en-1-yl tetradecanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Sealed tube; regioselective reaction;	94%

2-Phenyl-3-butyn-2-ol (127-66-2) + (E)-5-decen-1-ol (56578-18-8) → (E)-(2-(dec-5-en-1-yloxy)but-3-yn-2-yl)benzene

Conditions	Yield
With ferrocenium hexafluorophosphate In dichloromethane at 40℃; for 72h; Sealed tube;	90%

(E)-5-decen-1-ol (56578-18-8) + O-p-toluenesulfonyl benzyloxyhydroxamate (64420-86-6) → benzyl (E)-dec-5-en-1-yl(tosyloxy)carbamate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 18h; Mitsunobu Displacement; Inert atmosphere;	89%

(E)-5-decen-1-ol (56578-18-8) + 1-Adamantanecarboxylic acid (828-51-3) → (E)-dec-5-en-1-yl adamantane-1-carboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Sealed tube; regioselective reaction;	87%

(E)-5-decen-1-ol (56578-18-8) + benzoyl chloride (98-88-4) → (E)-dec-5-en-1-yl benzoate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	86%

(E)-5-decen-1-ol (56578-18-8) + dimethyl sulfoxide (67-68-5) → (2R*,1'S*)-2-(1'-methylthiopentyl)tetrahydropyran

Conditions	Yield
Stage #1: dimethyl sulfoxide With oxalyl dichloride In acetonitrile at -5℃; Stage #2: (E)-5-decen-1-ol In acetonitrile at -5℃; Reflux;	80%

(E)-5-decen-1-ol (56578-18-8) + benzaldehyde (100-52-7) → 1-Phenyl-2-vinyl-nonan-1-ol (155886-13-8)

Conditions	Yield
Stage #1: (E)-5-decen-1-ol With n-butyllithium; zirconocene dichloride In diethyl ether; hexane at -50 - 34℃; Stage #2: benzaldehyde In diethyl ether; hexane	73%

(E)-5-decen-1-ol (56578-18-8) → rac-(R)-2-((S)-1-iodopentyl)tetrahydro-2H-pyran

Conditions	Yield
Stage #1: (E)-5-decen-1-ol With Triphenylphosphine selenide; C62H69O4P In chloroform; cyclohexane at -35℃; for 0.333333h; Schlenk technique; Inert atmosphere; Stage #2: With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In chloroform; cyclohexane at -35℃; for 20h; Schlenk technique; Inert atmosphere;	70%
With N-iodo-succinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In toluene at 20℃; for 6h; Inert atmosphere; diastereoselective reaction;	67%

(E)-5-decen-1-ol (56578-18-8) + tert-butyl N-tosyloxycarbamate (105838-14-0) → tert-butyl (E)-dec-5-en-1-yl(tosyloxy)carbamate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16h; Mitsunobu Displacement; Inert atmosphere;	67%

(E)-5-decen-1-ol (56578-18-8) → rac-3-chloro-1-decene

Conditions	Yield
Stage #1: (E)-5-decen-1-ol With n-butyllithium; zirconocene dichloride In diethyl ether; hexane at -50 - 34℃; Stage #2: With N-chloro-succinimide In diethyl ether; hexane	65%

triethylsilyl chloride (994-30-9) + (E)-5-decen-1-ol (56578-18-8) → C16H34OSi

Conditions	Yield
Stage #1: (E)-5-decen-1-ol With 1H-imidazole; dmap In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: triethylsilyl chloride In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	56%

(E)-5-decen-1-ol (56578-18-8) + 1-phenyl-1-(cyclopropyl)prop-2-yne-1-ol (91962-51-5) → C22H30O

Conditions	Yield
With ferrocenium hexafluorophosphate In dichloromethane at 45℃; for 2h; Sealed tube;	50%

(E)-5-decen-1-ol (56578-18-8) + 1-cyclobutyl-1-hydroxy-1-phenyl-2-propyne (91909-16-9) → (E)-(1-cyclobutyl-1-(hex-3-en-1-yloxy)prop-2-yn-1-yl)benzene

Conditions	Yield
With ferroceniumboronic acid hexafluoroantimonate salt In dichloromethane at 45℃; Sealed tube;	42%

(E)-5-decen-1-ol (56578-18-8) → (E)-5-Decenylbromid (64275-66-7)

Conditions	Yield
With pyridine; phosphorus tribromide
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran 2: LiBr / acetone View Scheme

Upstream product

• 50-00-0 formaldehyd 
• 16695-35-5 (E)-4-nonen-1-yl bromide 
• 4221-03-8 5-hydroxypentanal 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 84168-29-6 Methyl 5(E)-decenoate 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 100419-71-4 oct-3-ynyl 4-methylbenzenesulfonate 
• 110-87-2 3,4-dihydro-2H-pyran 
• 66-25-1 hexanal 
• 68274-97-5 dec-5-yn-1-ol 
• 21662-11-3 trans-5-decenal 
• 139224-13-8 5-Decyn-1-yl tert-butyldimethylsilyl ether 
• 89625-08-1 (5R,6R)-6-(Diphenyl-phosphinoyl)-decane-1,5-diol 
• 77441-49-7 10-Tetrahydropyranyloxy-dec-5(E)-ene 

Downstream Products

• 67446-07-5 (Z)-5-decenyl acetate 
• 38421-90-8 (E)-5-decen-1-yl acetate 
• 155886-13-8 1-Phenyl-2-vinyl-nonan-1-ol 
• 1421437-31-1 N-((5E)-dec-5-en-1-yl)-4-methylbenzene-1-sulfonamide 
• 83483-57-2 (6Z,11E)-6,11-Hexadecadienylacetat 
• 83483-58-3 (6Z,11E)-6,11-Hexadecadienal 
• 112-30-1 1-Decanol 
• 64275-66-7 (E)-5-Decenylbromid 

Relevant articles and documents

Method for synthesizing sex pheromone of anarsia lineatella

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing sex pheromone of anarsia lineatella. The method comprises the following steps:with 5-hexyn-1-ol as a raw material, subjecting 5-hexyn-1-ol and1-bromobutane to a nucleophilic substitution reaction in the presence of n-butyllithium and HMPA to generate 5-decyn-1-ol, then performing reduction via lithium aluminum hydride to obtain (E)-5-decen-1-ol, and finally performing an acetylation reaction to obtain (E)-5-decen-1-ol acetate. According to the invention, a triple bond of alkyne is reduced into an E-type double bond by lithium aluminum hydride, so the method has the advantages of simple synthetic route, mild reaction conditions, good environmental compatibility and the like.

Synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate

The invention provides a synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate. With acrylaldehyde and acetylene being raw materials, a coupling reaction is carried out under the existence of a palladium catalyst to obtain 5-bromo-4E-pentenal, 5-bromo-4E-pentenal and methoxy methyl-triphenyl phosphonium chloride are subjected to a Wittig reaction to obtain 1E,5E-1-bromo-6-methoxy hexadiene, then 1E,5E-1-bromo-6-methoxy hexadiene and butyl magnesium bromide are subjected to a Kumada coupling reaction to obtain 1E,5E-1-methoxy decadiene, 5E-decenal is obtained through hydrolysis, then 5E-decene-1-alcohol is obtained through reducing, and finally the acetic acid 5E-decenyl acetate is obtained after esterification. The raw materials used for synthesis are low in price and easy to obtain, the synthesizing route is simple, reaction conditions are mild, operation is convenient and safe, industrialized production is easy, the yield is high, and the synthesizing method has important meaning for prevention and treatment of anarsia lineatella.

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