- CAS Number:4313-03-5
- Molecular Formula:C7H10 O
- Molecular Weight:110.156
- Mol File:4313-03-5.mol
Synonyms:2,4-Heptadienal,(E,E)- (8CI); (2E,4E)-2,4-Heptadienal; (E,E)-2,4-Heptadien-1-al;(E,E)-2,4-Heptadienal; 2-trans-4-trans-Heptadienal; 2E,4E-Heptadienal;all-trans-2,4-Heptadienal; trans,trans-2,4-Heptadienal;trans-2-trans-4-Heptadienal
- Melting Point:84.5 °C
- Boiling Point:84-84.5 ºC
- Flash Point:65 ºC
- Vapor Density:N/A
- Refractive Index:n20/D 1.534(lit.)
- Storage Temp.:Refrigerator (+4°C)
- Appearance/Colour:clear yellow liquid
2,4-Heptadienal,(2E,4E)- Safety information and MSDS
H302 Harmful if swallowed
H311 Toxic in contact with skin
H315 Causes skin irritation
H319 Causes serious eye irritation
P264 Wash ... thoroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell.
P330 Rinse mouth.
P302+P352 IF ON SKIN: Wash with plenty of water/...
P312 Call a POISON CENTER/doctor/…if you feel unwell.
P321 Specific treatment (see ... on this label).
P361+P364 Take off immediately all contaminated clothing and wash it before reuse.
P332+P313 If skin irritation occurs: Get medical advice/attention.
P362+P364 Take off contaminated clothing and wash it before reuse.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P337+P313 If eye irritation persists: Get medical advice/attention.
P405 Store locked up.
P501 Dispose of contents/container to ...
·Composition/information on ingredients:
|Chemical name||Common names and synonyms||CAS number||EC number||Concentration|
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
2,4-Heptadienal,(2E,4E)- Relevant articlesAll total 11 Articles be found
Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones
Xia, Xuanshu,Lao, Zhiqi,Toy, Patrick H.
supporting information, p. 1100 - 1104 (2019/05/24)
The scope of the triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as the reducing reagent has been examined. In all cases studied, the α,β-C=C double bond was selectively reduced to a C-C single bond while all other reducible functional groups remained unchanged. This reaction was applied to a large variety of conjugated dienones, a trienone, and a tetraenone. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence was developed to produce γ,δ-unsaturated ketones directly from simple building blocks. In these reactions the byproduct of the Wittig reaction served as the catalyst for the reduction reaction. This strategy was then used in the synthesis of naturally occurring moth pheromones to demonstrate its utility in the context of natural-product synthesis.
The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes
Binns, Falmai,Hayes, Roy,Hodgetts, Kevin J.,Saengchantara, Suthiweth T.,Wallace, Timothy W.,Wallis, Christopher J.
, p. 3631 - 3658 (2007/10/03)
Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.
Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z,3Z)-butyltelluro-4-methoxy-1,3-butadiene
Dabdoub, Miguel J.,Dabdoub, Vania B.,Baroni, Adriano C.M.,Hurtado, Gabriela R.,Barbosa, Sandro L.
experimental part, p. 1666 - 1670 (2010/05/19)
(1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α,β,γ,δ-unsaturated aldehydes of (E,E) configuration, which are precursors of trienes obtained from natural sources. The products of this reaction were employed in the synthesis of methyl-(2E,4E)-decadienoate 7, which is a component of the flavor principles of ripe Bartlett pears. Performing the Wittig reaction of the methyl triphenylphosphorane with the deca-(2E,4E)-dienal 5a, we were able to synthesize the undeca-(1,3E,5E)-triene 6a. This compound is a sex-pheromone component of the marine brown algae Fucus serratus, Dictyopteris plagiograma, and Dictyopteris australis. Performing the Wittig reaction of methyl triphenylphosphorane with the octa-(2E,4E)-dienal 5c, the nona-(1,3E,5E)-triene 6b was synthesized. The compound obtained is a sex-pheromone component of the marine brown alga Sargassum horneri. The octa-(1,3E,5E)-triene 6c was easily obtained from hepta-(2E,4E)-dienal 5d by the Wittig reaction with methyl triphenylphophorane. This compound is a sex-pheromone component of the marine brown alga Fucus serratus.
Iron-catalyzed aerobic oxidation of allylic alcohols: The issue of C=C bond isomerization
Liu, Jinxian,Ma, Shengming
supporting information, p. 5150 - 5153 (2013/11/06)
An aerobic oxidation of allylic alcohols using Fe(NO3) 3·9H2O/TEMPO/NaCl as catalysts under atmospheric pressure of oxygen at room temperature was developed. This eco-friendly and mild protocol provides a convenient pathway to the synthesis of stereodefined α,β-unsaturated enals or enones with the retention of the C-C double-bond configuration.
(2E)-4,4-dimethoxy-2-butenal in the synthesis of conjugated dienes and dienals
, p. 633 - 639 (2007/10/03)
Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)-and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds and also synthons for preparation of conjugated dienes as key compounds for building up other natural products.
2,4-Heptadienal,(2E,4E)- Synthetic route And Reaction conditions
WithSkeletonema costatum;Inwater;for 0.0166667h; sonicated;
Withcobalt acetylacetonate; lithium bromide;Intetrahydrofuran; 1-methyl-pyrrolidin-2-one;at -30 - 0 ℃; for 0.5h;
cis-2-penten-1-ol; ethyl (triphenylphosphoranylidene)acetate;Withmanganese(IV) oxide; benzoic acid;Indichloromethane;at 20 ℃; for 72h;
Withlithium aluminium tetrahydride;Indiethyl ether;at 0 ℃; for 1h;
Withmanganese(IV) oxide;Indichloromethane;at 20 ℃; for 78h; Title compound not separated from byproducts;
Withlithium aluminium tetrahydride; diethyl ether;Behandeln des erhaltenen Hepta-2t,4t-dien-1-ols (λmax:230 nm) mit Mangan(IV)-oxid in Petrolaether;
Withtetrahydrofuran;Behandeln der Reaktionsloesung mit Aethanol und mit Lithiumalanat und anschliessenden Behandeln mit wss.Schwefelsaeure;
Multistep reaction; (i), (ii) DMSO, BF3-Et2O;
Multi-step reaction with 4 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h
2: 1.) CuI / 1.) ether, 2.) ether, a) 0 deg C, 2 h, b) RT, 12 h
3: 91 percent / DDQ, H2O / CH2Cl2 / 2 h / Ambient temperature
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 2 h, 2.) CH2Cl2
Multi-step reaction with 4 steps
1: 83 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C
2: 78 percent / diethyl ether / -10 - 0 °C
3: 91 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
4: 87 percent / 1.) oxalyl chloride, DMSO; 2.) Et3N / CH2Cl2 / 1.) -78 deg C, 1 h; 2.) -78 deg C to 20 deg C
Multi-step reaction with 2 steps
1: 91 percent / DDQ, H2O / CH2Cl2 / 2 h / Ambient temperature
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 2 h, 2.) CH2Cl2
Multi-step reaction with 2 steps
1: 91 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
2: 87 percent / 1.) oxalyl chloride, DMSO; 2.) Et3N / CH2Cl2 / 1.) -78 deg C, 1 h; 2.) -78 deg C to 20 deg C
Multi-step reaction with 3 steps
1: 1.) CuI / 1.) ether, 2.) ether, a) 0 deg C, 2 h, b) RT, 12 h
2: 91 percent / DDQ, H2O / CH2Cl2 / 2 h / Ambient temperature
3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 2 h, 2.) CH2Cl2
Multi-step reaction with 3 steps
1: 78 percent / diethyl ether / -10 - 0 °C
2: 91 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
3: 87 percent / 1.) oxalyl chloride, DMSO; 2.) Et3N / CH2Cl2 / 1.) -78 deg C, 1 h; 2.) -78 deg C to 20 deg C
2,4-Heptadienal,(2E,4E)- Raw materials
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