85920-81-6

Basic information

• Product Name: Decanal, 10-bromo-
• Synonyms: Decanal, 10-bromo-;10-broMo-1-decanal;10-Bromodecanal;10-BROMODECANAL(WXG02068)
• CAS NO: 85920-81-6
• Molecular Formula: C₁₀H₁₉BrO
• Molecular Weight: 235
• Mol File: 85920-81-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 282.237 °C at 760 mmHg
• Flash Point: 27.016 °C
• Appearance: /
• Density: 1.152 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Decanal, 10-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Decanal, 10-bromo-(85920-81-6)
• EPA Substance Registry System: Decanal, 10-bromo-(85920-81-6)

Safety Data

• Hazardous Substances Data: 85920-81-6(Hazardous Substances Data)

Usage

General Description

Decanal, 10-bromo- is a chemical compound with the molecular formula C10H19BrO. It is a brominated derivative of decanal, which is a saturated aldehyde commonly found in essential oils and flavors. Decanal, 10-bromo- is a colorless liquid with a strong and pungent odor. It is used in various industrial applications, including the production of perfumes, flavors, and pharmaceuticals. Decanal, 10-bromo- is also utilized as an intermediate in organic synthesis for the preparation of other chemical compounds. Additionally, decanal, 10-bromo- has potential applications in research and development due to its unique chemical properties and reactivity.

Upstream product

• 7766-50-9 1-undecen-11-ylbromide 
• 53463-68-6 1-bromo-10-decanol 
• 50530-12-6 10-bromodecanoic acid 
• 1418759-68-8 C₂₂H₄₉BrO₂Si₂ 
• 130203-52-0 11-bromoundecane-1,2-diol 
• 112-43-6 10-Undecen-1-ol 
• 112-47-0 1,10-Decanediol 

Downstream Products

• 53463-68-6 1-bromo-10-decanol 
• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 
• 6948-45-4 11-bromoundecanenitrile 
• 1629637-05-3 11-methyldodec-10-en-1-yl p-toluenesulfonate 
• 86252-74-6 (2E,13Z)-octadeca-2,13-dienyl acetate 
• 123551-47-3 (2E,13Z)-2,13-octadecadien-1-ol 
• 71317-73-2 (11Z,13Z)-11,13-hexadecadienal 
• 162655-05-2 2-<(12R)-Carboxymethenylidentriphenylphosphoran>tridecyl-1,3-dioxolan 

Relevant articles and documents

Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions

We report a 12-step catalytic enantioselective formal synthesis of malhamensilipin A (3) and diastereoisomeric analogues from (E)-2-undecenal. The convergent synthesis relied upon iterative epoxidation and phosphorus(v)-mediated deoxydichlorination reactions as well a titanium-mediated epoxide-opening to construct the C11-C16 stereohexad. The latter transformation occurred with very high levels of stereoretention regardless of the C13 configuration of the parent epoxide, implicating anchimeric assistance of either the γ- or δ-chlorine atoms, and the formation of chloretanium or chlorolanium ions, respectively. A computational analysis of the chloronium ion intermediates provided support for the involvement of chlorolanium ions, whereas the potential chloretanium ions were found to be less likely intermediates on the basis of their greater carbocationic character.

Facile and efficient syntheses of (11Z,13Z)-hexadecadienal and its derivatives: Key sex pheromone and attractant components of notodontidae

Syntheses of (11Z,13Z)-hexadecadienal (1), (11Z,13Z)-hexadecadienol (2), (11Z,13Z)-hexadecadien-1-yl acetate (3), and (Z)-13-hexadecen-11-ynal (4) from commercially available starting material 10-bromo-1-decanol are reported. These (Z,Z)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: Alkylation of lithium alkyne under a low temperature, cis-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11Z,13Z)-hexadecadienal (1) in a 23.0% total yield via an eight-step sequence, alcohol (2) in a 21.9% total yield, acetate (3) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (4) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests.

Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2

A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.