65128-96-3

Basic information

• Product Name: Z-7-TETRADECENAL
• Synonyms: Z-7-TETRADECENAL;Z-7-TDAL;(7Z)-7-Tetradecenal;cis-7-tetradecenal;(Z)-tetradec-7-enal;7Z-14CHO;7Z-Tetradecenal
• CAS NO: 65128-96-3
• Molecular Formula: C₁₄H₂₆O
• Molecular Weight: 210.36
• EINECS: 265-493-9
• Product Categories: Pharm intermediate
• Mol File: 65128-96-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 297.4 °C at 760 mmHg
• Flash Point: 137.9 °C
• Appearance: /
• Density: 0.839±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00135mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: -20°C
• CAS DataBase Reference: Z-7-TETRADECENAL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-7-TETRADECENAL(65128-96-3)
• EPA Substance Registry System: Z-7-TETRADECENAL(65128-96-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 65128-96-3(Hazardous Substances Data)

Usage

General Description

Z-7-Tetradecenal is a chemical compound that is primarily used in the creation of various perfumes and fragrances. This linear α,β-unsaturated aldehyde also has applications in chemical synthesis, particularly in organic chemistry, due to its structural properties. It features a carbon chain of 14 atoms with a double bond at the 7th position, and an aldehyde (-CHO) group at the end of the chain. The compound is derived from natural sources like essential oils, or synthesized through a series of chemical reactions. Its structure allows it to readily undergo reactions with a variety of other chemicals, making it a valuable tool in the creation of complex molecular structures.

InChI:InChI=1/C14H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h7-8,14H,2-6,9-13H2,1H3/b8-7-

Synthetic route

cis-7,8-epoxy-14(Z)-heneicosene (83807-44-7, 83860-43-9) → (Z)-7-tetradecenal (65128-96-3)

Conditions	Yield
With periodic acid In diethyl ether at 0℃; for 1.5h;	82%

7-tetradecyne-1-ol (37011-94-2) → (Z)-7-tetradecenal (65128-96-3)

Conditions	Yield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 2: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

(Z)-tetradec-7-en-1-ol (40642-43-1) → (Z)-7-tetradecenal (65128-96-3)

Conditions	Yield
With pyridium chlorochromate In dichloromethane at 20℃; for 3h; Yield given;
With dipyridinium dichromate In dichloromethane for 2h;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at 0℃; for 1h;	8.7 g

2-(tetradec-7-yn-1-yloxy)tetrahydro-2H-pyran (37043-40-6) → (Z)-7-tetradecenal (65128-96-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 2: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 3: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) → (Z)-7-tetradecenal (65128-96-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C 2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

n-octyne (629-05-0) + (C5H5)2ZrHCl → (Z)-7-tetradecenal (65128-96-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C 2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

(Z)-7-tetradecenal (65128-96-3) + (R)-1,3-dihydroxytetradecane (139623-13-5) → (2S,4R)-4-undecyl-2-[(Z)-tridec-6-enyl]-1,3-dioxane (592543-36-7)

Conditions	Yield
With camphor-10-sulfonic acid In benzene at 50℃; under 70 Torr; for 2h;	100%

(Z)-7-tetradecenal (65128-96-3) → (7Z)-tetradec-7-enic acid (2430-95-7)

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tert-butyl alcohol at 20℃; for 3h;	96%

Methyl diethylphosphonoacetate (1067-74-9) + (Z)-7-tetradecenal (65128-96-3) → methyl (2E,9Z)-hexadeca-2,9-dienoate (158420-87-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 2.5h;	92%

Upstream product

• 40642-43-1 (Z)-tetradec-7-en-1-ol 
• 16974-10-0 1-acetoxy-(Z)-7-tetradecene 
• 83807-42-5 heneicosa-7(Z),14(Z)-diene 
• 83807-41-4 heneicosa-7,14-diyne 
• 111-24-0 1,5-dibromo-pentane 
• 629-05-0 n-octyne 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 37043-40-6 2-(tetradec-7-yn-1-yloxy)tetrahydro-2H-pyran 
• 83807-44-7 cis-7,8-epoxy-14(Z)-heneicosene 
• 37011-94-2 7-tetradecyne-1-ol 

Downstream Products

• 2430-95-7 (Z)-tetradec-7-enoic acid 
• 76963-23-0 3-oxo-(Z)-9-hexadecenal 
• 592543-41-4 2-(4-methoxybenzyloxy)ethyl 2-deoxy-2-(2,2-difluorotetradecanamido)-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-α-D-glycopyranoside 
• 592543-40-3 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside 

Relevant articles and documents

AN ALTERNATIVE SYNTHESIS OF UNSATURATED ALDEHYDOPHEROMONES

The pheromone 7(Z)-tetradecenal and its isomer 7(E)-tetradecenal were synthesized in four steps from commercially available starting materials.

(E4,Z9)-Tetradecadienal, a sex pheromone for three North American moth species in the genus Saturnia

The lepidopteran genus Saturnia has three representatives in North America, S. walterorum, S. mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14:Aid) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14:Ald) as a single component, Small amounts of (Z)-9-tetradecenal (Z9-14:Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14:Aid were no more attractive to male moths than E4,Z9-14:Ald alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.

3-Oxo-(Z)-9-hexadecenal: An unusual enolic β-keto aldehyde from a termite soldier defense secretion

-