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Z-7-Tetradecenal, a linear α,β-unsaturated aldehyde, is a chemical compound characterized by 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. It is derived from natural sources like essential oils or synthesized through a series of chemical reactions. Z-7-TETRADECENAL's 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.

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  • 65128-96-3 Structure
  • Basic information

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

    1. Melting Point: N/A
    2. Boiling Point: 297.4 °C at 760 mmHg
    3. Flash Point: 137.9 °C
    4. Appearance: /
    5. Density: 0.839±0.06 g/cm3 (20 ºC 760 Torr)
    6. Vapor Pressure: 0.00135mmHg at 25°C
    7. Refractive Index: 1.448
    8. Storage Temp.: -20°C
    9. Solubility: N/A
    10. CAS DataBase Reference: Z-7-TETRADECENAL(CAS DataBase Reference)
    11. NIST Chemistry Reference: Z-7-TETRADECENAL(65128-96-3)
    12. EPA Substance Registry System: Z-7-TETRADECENAL(65128-96-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 65128-96-3(Hazardous Substances Data)

65128-96-3 Usage

Uses

Used in Perfumery and Fragrance Industry:
Z-7-Tetradecenal is used as a fragrance ingredient for its ability to contribute to the overall scent profile of various perfumes and fragrances. Its unique chemical structure provides a distinct and versatile aroma that can be incorporated into a wide range of scent compositions.
Used in Chemical Synthesis:
In the field of organic chemistry, Z-7-Tetradecenal is used as a key intermediate in the synthesis of more complex molecules. Its structural properties, including the presence of a double bond and an aldehyde group, make it a valuable building block for creating a variety of chemical compounds.
Used in Research and Development:
Z-7-Tetradecenal is also utilized in research and development settings, where its reactivity and structural properties are studied to better understand the behavior of α,β-unsaturated aldehydes and their potential applications in various industries. This knowledge can lead to the discovery of new compounds and processes that can be applied in fields such as pharmaceuticals, materials science, and environmental science.

Check Digit Verification of cas no

The CAS Registry Mumber 65128-96-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,1,2 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 65128-96:
(7*6)+(6*5)+(5*1)+(4*2)+(3*8)+(2*9)+(1*6)=133
133 % 10 = 3
So 65128-96-3 is a valid CAS Registry Number.
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-

65128-96-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Z-7-TETRADECENAL

1.2 Other means of identification

Product number -
Other names (Z)-tetradec-7-en-1-al

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:65128-96-3 SDS

65128-96-3Synthetic route

cis-7,8-epoxy-14(Z)-heneicosene
83807-44-7, 83860-43-9

cis-7,8-epoxy-14(Z)-heneicosene

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

Conditions
ConditionsYield
With periodic acid In diethyl ether at 0℃; for 1.5h;82%
7-tetradecyne-1-ol
37011-94-2

7-tetradecyne-1-ol

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

Conditions
ConditionsYield
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)-tetradec-7-en-1-ol

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

Conditions
ConditionsYield
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

2-(tetradec-7-yn-1-yloxy)tetrahydro-2H-pyran

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

Conditions
ConditionsYield
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

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

Conditions
ConditionsYield
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

n-octyne

(C5H5)2ZrHCl

(C5H5)2ZrHCl

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

Conditions
ConditionsYield
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

(Z)-7-tetradecenal

(R)-1,3-dihydroxytetradecane
139623-13-5

(R)-1,3-dihydroxytetradecane

(2S,4R)-4-undecyl-2-[(Z)-tridec-6-enyl]-1,3-dioxane
592543-36-7

(2S,4R)-4-undecyl-2-[(Z)-tridec-6-enyl]-1,3-dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene at 50℃; under 70 Torr; for 2h;100%
(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

(7Z)-tetradec-7-enic acid
2430-95-7

(7Z)-tetradec-7-enic acid

Conditions
ConditionsYield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tert-butyl alcohol at 20℃; for 3h;96%
Methyl diethylphosphonoacetate
1067-74-9

Methyl diethylphosphonoacetate

(Z)-7-tetradecenal
65128-96-3

(Z)-7-tetradecenal

methyl (2E,9Z)-hexadeca-2,9-dienoate
158420-87-2

methyl (2E,9Z)-hexadeca-2,9-dienoate

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

65128-96-3Relevant articles and documents

AN ALTERNATIVE SYNTHESIS OF UNSATURATED ALDEHYDOPHEROMONES

Becker, D.,Kimmel, T.

, p. 1689 - 1692 (1982)

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

Synthesis of carboxymethyl GLA-60 ether derivatives containing an olefin in their chains and their LPS-antagonistic activities

Nakamura, Tsuyoshi,Watanabe, Yukiko,Shiozaki, Masao,Kanai, Saori,Kurakata, Shin-ichi

, p. 1011 - 1022 (2007/10/03)

Anomeric carboxymethyl GLA-60 olefine derivatives having ether chains instead of ester chains in their side chains were synthesized and their biological activities toward both human U937 cells and mouse PEC-macrophage cells were measured. The species-specific behavior of these compounds in humans (LPS-antagonistic) and mice (very weak LPS-antagonistic, but almost inactive) found this time was different from that in humans (LPS-antagonistic) and mice (endotoxic) found in the biosynthetic precursor of lipid A, such as lipid IVa. However, this fact also shows, interestingly enough, that a difference exists in the molecular recognition between human and mouse LPS receptors.

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

Mcelfresh, J. Steven,Millar, Jocelyn G.,Rubinoff, Daniel

, p. 791 - 806 (2007/10/03)

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.

Vinylic Organoboranes. 4. A General, One-Pot Synthesis of 6- and 7-Alkyn-1-ols via Boracyclanes. Influence of Steric Effects in the Iodination of Lithium Alkynyl "Ate" Complexes of Dialkylborinates

Brown, Herbert C.,Basavaiah, D.,Bhat, N. G.

, p. 4518 - 4521 (2007/10/02)

The iodination of the "ate" complexes derived from various B-alkoxyborinane derivatives and 1-alkynyllithium has been investigated.The results indicate the ate complex from B-methoxyborinane is converted into desired 6-alkyn-1-ol in a yield of only 22percent, with much larger amounts, 65percent, of the undesired 1-iodo-1-alkyne.Increases in the steric bulk of the alkoxy group on boron increase the yield of the required 6-alkyn-1-ol with the best results realized with B-(triphenylmethoxy)borinane.Treatment of B-(triphenylmethoxy)borinane with 1-alkynyllithium affords the corresponding "ate" complex.Subsequent iodination induces the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, resulting in the formation of the one-carbon homologated borepane moiety.This then undergoes a rapid deiodoboronation to afford the corresponding (6-alkyn-1-yl)boronate ester.Oxidation of these esters produces the desired 6-alkyn-1-ols in excellent yields (85percent).An attempt to extend this reaction to di-n-alkylborinates to prepare the corresponding unsymmetrical alkynes did not achieve satisfactory results.Alternatively, the iodination of the "ate" complex from B-methylborinane and 1-alkynyllithium, followed by oxidation, provides the required 6-alkyn-1-ols in high yields.This procedure has been successfully extended to the seven-membered borepane moiety to provide the corresponding 7-alkyn-1-ols.Extension of this reaction to the di-n-alkylmethylboranes provides the corresponding unsymmetrical alkynes in good yields.Thus, these procedures constitute a simple, general and one-pot synthesis of the desired alkyn-1-ols, valuable synthons in organic synthesis.Insect pheromones, (Z)-7-tetradecenaland (Z)-7-hexadecenal, were readily prepared in excellent yields by utilizing this convenient procedure.

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