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Dibromoneopentyl glycol is a brominated version of neopentyl glycol diglycidyl ether.
Dibromoneopentyl glycol is an aliphatic organic chemical in the glycidyl ether family that is used in epoxy resin formulations.
Dibromoneopentyl glycol has the molecular formula C11H18Br2O4.
CAS Number: 3296-90-0
Molecular Formula: C5H10Br2O2
Molecular Weight: 261.94
EINECS Number: 221-967-7
Synonyms: 3296-90-0, 2,2-Bis(bromomethyl)propane-1,3-diol, 2,2-BIS(BROMOMETHYL)-1,3-PROPANEDIOL, Dibromoneopentyl glycol, Pentaerythritol dibromide, Dibromopentaerythritol, 1,3-Propanediol, 2,2-bis(bromomethyl)-, Pentaerythritol dibromohydrin, FR 1138, NCI-C55516, 1,3-Dibromo-2,2-dimethylolpropane, 2,2-Dibromomethyl-1,3-propanediol, NSC 9001, DBNPG, DTXSID9020164, 2,2-Bis(2-bromomethyl)-1,3-propanediol, 1,3-Propanediol, 2,2-bis(2-bromomethyl)-, 1,3-Dibromo-2,2-dihydroxymethylpropane, 2,2-Bis(bromomethyl)-1,3-propanediol, technical grade, CHEBI:82294, Fr 522, 4ZHG182S25, NSC-9001, 1,3-dibromo-2,2-bis(hydroxymethyl)propane, Pentaerythritol-d8Dibromide, DTXCID50164, CAS-3296-90-0, CCRIS 5972, HSDB 4184, EINECS 221-967-7, BRN 1304582, UNII-4ZHG182S25, dibromoneopentylglycol, MFCD00004688, beta-Fructofuranosidase, 1,2-dimethylolpropane, EC 221-967-7, Pentaerythritol, dibromohydrin, WLN: Q1X2E2E1Q, 4-01-00-02554 (Beilstein Handbook Reference), 1, 2,2-bis(bromomethyl)-, SCHEMBL399680, CHEMBL1407005, CHUGKEQJSLOLHL-UHFFFAOYSA-, 1, 2,2-bis(2-bromomethyl)-, NSC9001, Tox21_201856, Tox21_300296, 2,2-bisbromomethylpropane-1,3-diol, BR1298, AKOS005765877, 2,2-Di(bromomethyl)propane-1,3-diol, PENTAERYTHRITOL DIBROMIDE [HSDB], 1,3-Propanediol, 2,2-bis(bromomethyl), 2,2-bis(bromomethyl) 1,3-propane diol, 2,2-bis-(bromomethyl)propane-1,3-diol, NCGC00090690-01, NCGC00090690-02, NCGC00090690-03, NCGC00090690-04, NCGC00254196-01, NCGC00259405-01, AS-12581, CS-0204802, D1808, NS00007621, EN300-78451, 2,2-Bis(bromomethyl)-1,3-propanediol, 98%, C19199, Q26841193, F0001-0977, InChI=1/C5H10Br2O2/c6-1-5(2-7,3-8)4-9/h8-9H,1-4H2, 221-967-7, Pentaerythritol dibromide;Pentaerythritol dibromohydrin;pentaerythritoldibromide;pentaerythritoldibromohydrin;SAYTEX(R) FR-1138 FLAME RETARDANT;SAYTEX FR-1138;2,2-DI(BROMOMETHYL)PROPANE-1,3-DIOL;2,2-BIS(BROMOMETHYL)-1,3-PROPANEDIOL
Dibromoneopentyl glycol, chemically known as 2,2-bis(bromomethyl)propane-1,3-diol, is an organic compound characterized by the presence of two bromomethyl groups attached to a neopentyl glycol backbone.
Dibromoneopentyl glycol is a halogenated diol that appears as a crystalline solid with a relatively high molecular weight due to the bromine atoms, which contribute to its density and chemical reactivity.
Dibromoneopentyl glycol is typically used as an intermediate in chemical synthesis, especially in the manufacture of flame retardants, where its bromine content provides the material with the ability to inhibit or slow down combustion processes.
Dibromoneopentyl glycol can be utilized in the synthesis of specialty chemicals and intermediates, where its unique structure allows for selective functionalization and modification, expanding its role in creating advanced materials with tailored properties.
Due to its brominated nature, the compound requires careful handling and adherence to safety protocols, as brominated substances may pose environmental and health risks if not managed properly.
In industrial applications, dibromoneopentyl glycol serves as a key precursor for the production of various flame-retardant polymers and additives, which are commonly incorporated into plastics, textiles, and electronic components to improve their fire resistance and enhance safety standards.
The molecule’s two hydroxyl groups enable it to react readily with other chemical species, facilitating its integration into polymer backbones or as a cross-linking agent, which imparts desirable physical properties such as toughness and thermal stability to the final materials.
Dibromoneopentyl glycol is an important industrial chemical that plays a vital role in the development of flame retardant products and advanced materials, contributing significantly to fire safety and performance improvements in a wide range of commercial and industrial applications.
The usual method of synthesis is to take Dibromoneopentyl glycol and react with epichlorohydrin using Lewis acid catalysis to form the halohydrin.
This species is then reacted with sodium hydroxide to form the diglycidyl ether.
Dibromoneopentyl glycol, also known by its chemical name 2,2-bis(bromomethyl)propane-1,3-diol, is a halogenated organic compound that belongs to the class of brominated diols.
Dibromoneopentyl glycols molecular structure features two bromomethyl groups (-CH₂Br) attached symmetrically to a neopentyl glycol core, which consists of a propane backbone bearing two hydroxyl (-OH) groups at the 1 and 3 positions.
This dual functionality of bromine and hydroxyl groups makes dibromoneopentyl glycol a highly reactive and versatile intermediate in various industrial chemical processes.
Dibromoneopentyl glycol is a vital chemical intermediate widely used in the production of flame retardants and advanced polymers.
Dibromoneopentyl glycols unique molecular structure combining bromine atoms with hydroxyl groups allows it to enhance fire safety properties, improve material performance, and enable the synthesis of complex chemical products across diverse industries including construction, electronics, automotive, and specialty chemicals.
Dibromoneopentyl glycol is a highly functionalized brominated diol, featuring a compact yet reactive molecular framework.
This compound’s chemical structure—comprising a neopentyl backbone substituted with two bromomethyl groups and two hydroxyl groups—confers it with both hydrophilic and lipophilic properties, allowing it to interact effectively within diverse chemical environments.
The bromine atoms impart a high atomic weight and electron density, which not only influences its physical properties such as density and boiling point but also significantly enhances its flame-retardant characteristics.
In the field of fire safety and flame retardancy, Dibromoneopentyl glycol is often incorporated into polymer matrices, either as a reactive additive or as a precursor to more complex flame-retardant systems.
The bromine atoms in Dibromoneopentyl glycol release bromine radicals when exposed to high temperatures during combustion.
These radicals act by interrupting the free radical chain reactions that propagate flames, thus effectively suppressing ignition and flame spread.
This mechanism makes Dibromoneopentyl glycol-containing formulations essential in manufacturing flame-retardant materials used in electronics housings, circuit boards, insulation foams, textiles, and automotive components, where fire hazards are a critical safety concern.
Dibromoneopentyl glycol’s unique structure allows for the design of specialty chemical intermediates that require precise placement of bromine and hydroxyl functionalities.
This is valuable in pharmaceutical and agrochemical research where site-specific chemical modifications are needed to create molecules with targeted biological activity or controlled release characteristics.
Its role as an intermediate expands its industrial relevance beyond flame retardancy into broader chemical manufacturing domains.
Melting point: 112-114 °C (lit.)
Boiling point: 235°C (rough estimate)
Density: 1.8049 (rough estimate)
Vapor pressure: 10 mm Hg (178 °C)
Refractive index: 1.5120 (estimate)
Storage temp.: Inert atmosphere, Room Temperature
Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
pKa: 13.57 ± 0.10 (Predicted)
Form: Solid
Color: White to Off-White
Water solubility: 19.4 g/L at 20℃
LogP: 1.08
Dibromoneopentyl glycol is as a precursor in the manufacture of flame retardants, especially those used in polymer and resin formulations.
The presence of bromine atoms is crucial because bromine is effective at interrupting combustion reactions by scavenging free radicals generated during the burning process, thereby reducing flammability.
As a result, materials treated with dibromoneopentyl glycol-derived flame retardants exhibit enhanced fire resistance, making them suitable for applications in construction materials, electrical and electronic devices, automotive parts, and textiles, where improved fire safety standards are essential.
Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents.
They react with oxoacids and carboxylic acids to form esters plus water.
Oxidizing agents convert them to aldehydes or ketones.
Alcohols exhibit both weak acid and weak base behavior.
They may initiate the polymerization of isocyanates and epoxides.
The flame retardant 2,2-bis(bromomethyl)-1,3-propanediol, technical grade, is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Dibromoneopentyl glycol’s two hydroxyl groups allow it to act as a cross-linking agent or a reactive intermediate in the synthesis of various polymers and resins.
These hydroxyl groups can undergo esterification, etherification, or other chemical modifications, enabling the incorporation of dibromoneopentyl glycol into polymer chains to enhance mechanical strength, thermal stability, and chemical resistance.
Dibromoneopentyl glycol is often used in the synthesis of epoxy resins, unsaturated polyesters, and other specialty polymers where fire resistance and durability are critical.
Due to the compound’s reactive nature and brominated structure, it is also employed in the preparation of specialty chemicals and intermediates used in pharmaceuticals, agrochemicals, and chemical research.
Its ability to introduce bromine atoms and reactive hydroxyl groups into complex molecules makes it a valuable tool for synthetic chemists seeking to design new materials or active compounds with specific functionalities.
However, because Dibromoneopentyl glycol contains bromine, which is a halogen, it requires careful handling and strict adherence to environmental and safety regulations.
Brominated compounds can pose environmental concerns such as persistence in the environment, potential bioaccumulation, and toxicity to aquatic organisms if not properly managed.
Therefore, facilities using this compound typically implement rigorous containment, waste treatment, and exposure control measures to minimize health and environmental risks.
Uses:
Dibromoneopentyl glycol is a brominated flame retardant, previously shown to be a multisite carcinogen in experimental animals.
The compound is used as a fire retardant in unsaturated polyester resins, in molded products, and in rigid polyurethane foam.
It shows clear evidence of carcinogenicity and genotoxicity activity.
Dibromoneopentyl glycol is a brominated flame retardant, previously shown to be a multisite carcinogen in experimental animals.
Dibromoneopentyl glycol is used as a fire retardant in unsaturated polyester resins, in molded products, and in rigid polyurethane foam.
Dibromoneopentyl glycol shows clear evidence of carcinogenicity and genotoxicity activity.
A key use of the material is reducing the viscosity of epoxy resins.
As an epoxy modifier it is classed as a reactive diluent, which may then be formulated into CASE applications (coatings, adhesives, sealants, and elastomers and composite materials).
As Dibromoneopentyl glycol is an organobromine compound it is used to improve the Flame retardant properties of materials.
Flame retardant coatings including powder coatings maybe produced.
Dibromoneopentyl glycol is a highly versatile chemical intermediate widely utilized across various industries, primarily due to its unique molecular structure combining bromine atoms and hydroxyl groups.
One of its most significant applications is in the manufacture of flame retardants, where Dibromoneopentyl glycol serves as a crucial building block in creating brominated flame-retardant additives.
These additives are incorporated into a broad range of polymers and materials, including plastics, textiles, and coatings, to enhance their fire resistance.
The bromine atoms within Dibromoneopentyl glycol are instrumental in interrupting the combustion process by scavenging free radicals during burning, which effectively reduces the spread and intensity of flames.
Consequently, materials containing Dibromoneopentyl glycol-based flame retardants are commonly used in the construction, automotive, aerospace, and electronics industries, where stringent fire safety regulations are enforced.
In addition to flame retardancy, Dibromoneopentyl glycol finds important use as a cross-linking agent and reactive intermediate in polymer chemistry.
Its two hydroxyl groups make it reactive towards isocyanates, epoxides, and acid derivatives, allowing it to be incorporated into the backbone or side chains of polymers such as polyurethanes, epoxy resins, and polyesters.
This incorporation imparts enhanced mechanical strength, thermal stability, and chemical resistance to the resulting materials.
Dibromoneopentyl glycol-modified polyurethanes exhibit superior toughness and flame retardancy, making them suitable for high-performance coatings, adhesives, sealants, and elastomers used in demanding industrial environments.
Moreover, dibromoneopentyl glycol is used in the formulation of specialty chemicals and intermediates where precise chemical functionality is required.
Its bifunctional nature allows chemists to create complex molecules with tailored properties for applications ranging from pharmaceuticals to agricultural chemicals.
In these contexts, Dibromoneopentyl glycol can be modified or reacted further to introduce specific reactive groups or to serve as a scaffold for bioactive compounds.
Within the electronics industry, Dibromoneopentyl glycol-derived flame retardants are incorporated into components such as printed circuit boards, cable insulation, and connectors to comply with fire safety standards while maintaining electrical performance.
Similarly, in the textile sector, Dibromoneopentyl glycol-based treatments are applied to fabrics and upholstery materials to improve their flame resistance without compromising flexibility or comfort.
Additionally, Dibromoneopentyl glycol is utilized in the automotive industry, where the demand for materials that combine fire safety with durability and lightweight characteristics is growing.
Dibromoneopentyl glycol-based flame retardants and polymers are found in interior components, engine parts, and electrical housings, contributing to safer and more reliable vehicles.
Despite these broad applications, the use of dibromoneopentyl glycol is carefully regulated due to concerns about the persistence and bioaccumulation of brominated substances.
As a result, manufacturers often balance its use with environmental considerations, developing formulations that minimize ecological impact while maintaining performance.
Safety Profile:
Dibromoneopentyl glycol presents several health and safety hazards primarily due to its chemical composition as a brominated organic compound and its physical form, usually as a crystalline solid or powder.
One of the main concerns when handling Dibromoneopentyl glycol is its potential to cause skin and eye irritation.
Direct contact with the solid or dust can lead to redness, itching, or inflammation of the skin, and if particles come into contact with the eyes, they may cause discomfort, watering, or more serious irritation.
Protective gloves, safety goggles, and appropriate clothing are strongly recommended to prevent such exposures during handling or processing.
Inhalation of dust or fine particulate matter generated from Dibromoneopentyl glycol can irritate the respiratory tract, causing symptoms such as coughing, sneezing, nasal irritation, or shortness of breath.
Workers with pre-existing respiratory conditions such as asthma or bronchitis may be particularly sensitive to airborne dust, so the use of respiratory protection and adequate ventilation is essential in workplaces where dust exposure is possible.
While Dibromoneopentyl glycol is not classified as acutely toxic under typical industrial exposure conditions, accidental ingestion could cause gastrointestinal irritation, leading to nausea, vomiting, or abdominal pain.
It is important to prevent accidental ingestion by following good hygiene practices, such as washing hands thoroughly before eating or drinking, and ensuring that food and beverages are kept away from work areas.
