50816-19-8

Basic information

• Product Name: 8-Bromo-1-octanol
• Synonyms: 1-bromo-octan-8-ol;1-Octanol, 8-bromo-;8-bromo-1-octano;8-BROMOOCTANOL;8-BROMO-1-OCTANOL;S,1000;OCTAMETHYLENE BROMOHYDRIN;8-bromooctan-1-ol
• CAS NO: 50816-19-8
• Molecular Formula: C₈H₁₇BrO
• Molecular Weight: 209.12
• EINECS: 256-785-7
• Product Categories: omega-Bromoalkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Linear hydrocarbon series;Alcohols;Bifunctional Crosslinkers;Building Blocks;C7 to C8;Chemical Biology;Chemical Synthesis;Linkers;Organic Building Blocks;Oxygen Compounds;Peptide Chemistry;OLED materials,pharm chemical,electronic
• Mol File: 50816-19-8.mol

Chemical Properties

• Boiling Point: 79-80 °C0.07 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.22 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000403mmHg at 25°C
• Refractive Index: n20/D 1.480(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• PKA: 15.19±0.10(Predicted)
• BRN: 1900837
• CAS DataBase Reference: 8-Bromo-1-octanol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Bromo-1-octanol(50816-19-8)
• EPA Substance Registry System: 8-Bromo-1-octanol(50816-19-8)

Safety Data

• Statements: 36-38
• Safety Statements: 23-24/25-37-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 50816-19-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
8-Bromo-1-octanol is used as a synthetic intermediate for the production of various organic compounds. It serves as a key reactant in the synthesis of different types of molecules, including 8-phenylselanyl-octan-1-ol, (E)-10-hydroxy-2-decenoic acid (royal jelly acid), and (Z)-14-methyl-9-pentadecenoic acid.
In the synthesis of 8-phenylselanyl-octan-1-ol, 8-Bromo-1-octanol reacts with diphenyl-diselane, utilizing sodium borohydride as a reagent and ethanol as a solvent at ambient temperature, yielding a product with approximately 96% efficiency.
Used in Pharmaceutical and Biochemical Research:
8-Bromo-1-octanol's unique chemical properties make it a valuable compound in the development of pharmaceuticals and biochemical research. Its ability to participate in various chemical reactions allows for the creation of new molecules with potential applications in medicine and other industries.
Used in the Synthesis of Specialty Chemicals:
Due to its reactivity and structural characteristics, 8-Bromo-1-octanol is also utilized in the synthesis of specialty chemicals that may have specific applications in various industrial sectors, such as fragrances, agrochemicals, or materials science.

InChI:InChI=1/C8H17BrO/c9-7-5-3-1-2-4-6-8-10/h10H,1-8H2

Upstream product

• 128133-92-6 1-(allyloxy)-8-bromooctane 
• 64-17-5 ethanol 
• 1427195-71-8 C₁₁H₂₀BrClO₂ 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 629-41-4 1,8-Octanediol 
• 62168-26-7 dibromo-1,1 octane 
• 2104-19-0 azelaic monomethyl ester 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 54863-44-4 8-bromooctanenitrile 
• 117952-77-9 8-bromo-1-(1-butoxyethoxy)octane 
• 26825-92-3 methyl 8-bromooctanoate 
• 17696-11-6 8-bromooctanoic acid 

Downstream Products

• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 83248-81-1 (E)-9-(phenylthio)-10-dodecen-1-ol 
• 132841-85-1 8-(phenylselanyl)octan-1-ol 
• 60037-69-6 9-tetradecyn-1-ol 
• 1053727-25-5 Benzoic acid (2R,3S,5R)-3-(8-bromo-octyloxymethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 593-12-4 1-bromo-8-fluorooctane 
• 17696-11-6 8-bromooctanoic acid 
• 28598-82-5 1-bromo-8-chloro-octane 
• 578726-13-3 8-(5-benzyloxy-1H-indol-1-yl)-1-octanol 
• 603132-75-8 N-benzyl-N'-bromooctyl-N'-tert-butoxycarbonyl sulfamide 
• 884508-75-2 8-bromooctyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 53596-81-9 8-bromooctyl alcohol acetate 
• 6919-99-9 hepta-O-acetyl-α-maltosyl chloride 
• 165330-95-0 1-(8-bromooctyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Relevant articles and documents

Influence of liquid crystalline formation on the phase behavior of side-chain liquid crystalline block copolymers

A series of narrowly distributed diblock copolymers composed of amorphous components and side-chain liquid crystalline (LC) polymer, poly (butyl acrylate)-block-poly [8-(4-cyano-4′-biphenyl)-1-octanoyl acrylate] (PBA-b-PCBOA), with side-chain LC block weight fraction (fw,PCBOA) ranging from 25% to 87%, were synthesized by atom transfer radical polymerization (ATRP). Their thermal property, LC behavior, bulk phase behavior and thin film morphology were studied by differential scanning calorimetry (DSC), polarizing optical microscope (POM), small-angle X-ray scattering (SAXS) techniques and atomic force microscopy (AFM), respectively. The results show the diblock copolymers with different composition could present sphere, lamellar and cylinder morphologies before the order-disorder transition. As the mesogen units self-organize to form smectic phase, the lamellar morphology dominates during the majority LC block weight fraction range (fw,PCBOA = 46%-77%) to minimized the surface energy. Interestingly, for spin-coated thin film, the lamella phase separation size decreased with increasing annealing time. For the copolymer with fw,PCBOA of 67%, a thermoreversible order-order transition (OOT) and lamella to lamella/modified layer (L/ML), were observed.

Chemoenzymatic synthesis of (R)-(+)-2-methylbutan-1-ol, a chiral synthon for the preparation of optically active pheromones

Optically active (R)-(+)-2-methylbutan-1-ol (which is not commercially available) was prepared by a chemoenzymatic synthesis, in which the key step involved a reduction catalyzed by baker's yeast. The synthon was used in the synthesis of (R)-10-methyldodecan-1-yl acetate, the chiral methyl-branched pheromone of Adoxophyes sp.

Identification and synthesis of the male produced volatiles of the carrion beetle, Oxelytrum erythrurum (Coleoptera: Silphidae)

Necrophagous beetles belonging to the family Silphidae are recognized as potentially useful in forensic investigations (to estimate post mortem interval). Gas chromatography analyses of extracts of aerations of adult Oxelytrum erythrurum revealed the presence of two male-specific compounds. These compounds were identified as (Z)-1,10-nonadecadiene (major) and 1-nonadecene (minor) using microderivatizations of the natural male extract, such as hydrogenation, partial reduction and methylthiolation, mass spectrum comparisons, and co-injections with authentic standards. Both compounds might be components of a pheromone responsible for sexual communication in this species.

Fluorinated analogs of ester components of red bollworm sex pheromone

Fluorinated analogs of the two geometrical isomers of the red bollworm moth sex pheromone were synthetized by palladium-catalyzed cross coupling reactions.

Nucleophilic substitution reactions of unbranched alkyl amines using triazine reagents

Since amines are present in many organic, biological, and drug molecules, a strategy of synthesizing desired compounds by nucleophilic substitution reactions of these amines is very attractive. By using triazine reagents, we have found that nucleophilic substitution reactions of unbranched alkyl amines via morpholine derivatives are feasible. This method can be performed under milder reaction conditions than those in previously reported methods.

Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.

Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound

The invention provides a synthesis method of a (Z/E)-8-dodecane-1-alcohol acetate compound. Specifically, the method includes the following steps: preparing 8-bromooctanol from 1,8-octanediol, then performing esterification reaction to obtain 8-Bromooctanol acetate, and then preparing omega-acetoxyoctanyl triphenyl phosphine bromide salt, and finally performing reaction through Scholoer-wittig toobtain (Z/E)-8-dodecene-1-alcohol acetate. The synthesis method has the advantages of high availability of raw materials, high yield and good selectivity, and is suitable for industrial production.

Simple synthesis method for sex pheromones of oriental fruit moths

The invention belongs to the field of chemical synthesis, and particularly relates to a simple synthesis method for sex pheromones of oriental fruit moths. The method includes subjecting 1,8-octandiolas a raw material to unilateral bromination reaction to obtain 8-bromooctanol, reacting the 8-bromooctanol with triphenylphosphine to obtain 8-hydroxyoctyl triphenylphosphonium salt, subjecting the 8-hydroxyoctyl triphenylphosphonium salt and n-butanal to Wittig reaction under the action of an alkali to obtain (Z/E)-8-dodecene-1-alcohol, and performing acetylation under the action of pyridine andacetic anhydride to obtain a target product. The cis-trans ratio of enol obtained after the Wittig reaction ranges from 91.8:8.2 to 92.9:7.1; within the optimal attraction range, and by strictly controlling the amount of the acetic anhydride, the properly proportioned sex pheromones of the oriental fruit moths can be obtained according to a 'one-pot' method.

COMPOSITIONS AND METHODS FOR DELIVERY OF MACROMOLECULES

The present disclosure provides endosomal disruptors, which are useful for facilitating delivery of a macromolecule to the cytoplasm of a cell. The present disclosure provides compositions comprising an endosomal disruptor and a macromolecule. The present disclosure provides methods of delivering a macromolecule to the cytoplasm of a cell.

DENTAL COMPOSITION

The present invention relates to a dental composition comprising a specific polymerizable compound and a polymerization initiator system. Furthermore, the present invention relates to the specific polymerizable compound as such and its use in a dental composition. The specific polymerizable compound of the present invention has an N-allyl (meth)acrylamide group, which nitrogen atom is substituted with an alkyl or alkenyl group optionally substituted by a group selected from a hydroxyl group, a C1-4 alkoxy group, a tertiary amino group and a carboxyl group, wherein 1 to 8 carbon atoms in the main chain of the alkyl or alkenyl group may independently from each other be replaced by a heteroatom selected from an oxygen atom and a sulfur atom.