1,3-Dibromo-2,2-dimethylpropane , CAS No.5434-27-5

CAS: 5434-27-5 Cat. No.: D1368255 Formula: C₅H₁₀Br₂ Peso molecolare: 229.94 Numero EC: 226-598-5 PubChem CID: 79491

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CC(C)(CBr)CBr

IUPAC Name

1,3-dibromo-2,2-dimethylpropane

InChIKey

UXAFLFGXSIWWMY-UHFFFAOYSA-N

INCHI

1S/C5H10Br2/c1-5(2,3-6)4-7/h3-4H2,1-2H3

Isomeri SMILES

CC(C)(CBr)CBr

PubChem CID

79491

Peso molecolare

229.94

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Classe Organobromides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Classe: Organobromides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organobromides
• Alternative Parents: Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydrocarbon derivative - Organobromide - Alkyl halide - Alkyl bromide - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as organobromides. These are compounds containing a chemical bond between a carbon atom and a bromine atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 229.940 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 229.913 Da
• Monoisotopic Mass: 227.915 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 44.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable. No tested bioanalytical applications (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical use, refer to the Reaction Conditions and Synthetic Utility sections for procedure-oriented guidance in chemical synthesis.

Biological Roles

This compound is a synthetic halogenated hydrocarbon with no known natural biological role.

General considerations (literature)

• Not a metabolite or cofactor. If introduced biologically, alkyl bromides can act as electrophiles toward nucleophilic biomolecules, but such interactions are typically undesired and form the basis of standard toxicity/irritancy precautions.
• Enzymatic pathways for direct utilization are not known; degradation in the environment proceeds via abiotic hydrolysis, photolysis, or microbial cometabolism of haloalkanes.
• In biochemical research, its primary relevance is as a hydrophobic linker/alkylating handle in synthetic probes or polymer conjugates prepared outside biological systems; it is not used in buffer or cellular media directly.

Buffer Applications

Not typically applicable. 1,3-Dibromo-2,2-dimethylpropane is a hydrophobic, non-ionizable organic halide and is not used to prepare buffer systems. For laboratory use, focus on sections covering Reaction & Applications, Synthetic Utility, and Reaction Conditions.

Green Alternatives

Context

• Alkyl bromides often pose environmental and health concerns (persistence, toxicity) and are typically derived using energy- and halogen-intensive processes. Where feasible, consider greener functional equivalents.

Potential greener substitutes or strategies (general)

• Replace bromides with sulfonate leaving groups: α,ω-diols converted to ditosylates or dimesylates can provide similar reactivity with less persistent halogens; waste streams avoid inorganic bromide.
• Use dialkyl carbonates (e.g., dimethyl or diethyl carbonate) for alkylation when compatible; these can act as benign alkylating agents under catalytic conditions and generate CO2/alcohol byproducts.
• Employ catalytic cross-couplings from alcohol derivatives: Redox-neutral activation (e.g., nickel-catalyzed coupling of redox-active esters) can circumvent alkyl bromides.
• Process improvements: Select safer solvents (2-MeTHF, CPME, anisole) in place of chlorinated media; apply PTC to operate at lower temperatures; continuous flow handling to reduce inventory of halogenated intermediates.

Trade-offs

• Reactivity: Neopentyl sterics make greener nucleophiles/conditions less effective; harsher or catalytic activation may be needed, which can offset green gains.
• Purification: Sulfonates and carbonates may be more polar, easing separations but altering downstream compatibility.

Brief comparison

• 1,3-Dibromo-2,2-dimethylpropane vs 1,3-ditosyloxy-2,2-dimethylpropane: Similar synthetic roles; the latter avoids bromide emissions but may require stronger bases or higher temperatures for displacement.

Pharmaceutical Uses

No pharmacopeial/excipient role is typical for this compound.

General context (non-clinical)

• Potential role as a synthetic intermediate: α,ω-dihalides may be used to construct hydrophobic linkers or to introduce neopentyl groups in API intermediates during route development. Any such use remains strictly within chemical synthesis; the material is not formulated for administration.
• Manufacturing considerations: If employed in GMP settings, tight control of residual halides, inorganic bromide, and genotoxic impurity profiles is essential. Alternative leaving groups (e.g., ditosylates) may be preferred in regulatory-sensitive contexts to avoid alkyl bromide carryover.
• Regulatory note: This product is supplied for research use only; it is not approved for human or veterinary use.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Computed/Literature values (for reference; not item specifications)

• Molecular formula: C5H10Br2
• Molecular weight: ~229.94 g/mol (calculated from atomic weights)
• Physical state/description (literature): Typically a colorless to pale yellow, high-density organic liquid; characteristic alkyl bromide odor.
• Solubility (literature): Low in water; miscible with many organic solvents (e.g., ethers, chlorinated solvents, aromatics, and many polar aprotics).
• Acid/base: Non-ionizable, neutral organic halide; no pKa relevant to aqueous acid/base.
• Partitioning (literature expectation): Hydrophobic; high logP typical of dihalogenated alkanes of similar MW.

Notes for practice (general)

• High refractivity and density are typical for brominated aliphatics; verify exact values on the lot-specific CoA/SDS before use in quantitative work.
• Viscosity and vapor pressure are moderate-to-low compared with lighter mono-bromides due to higher molecular mass.

Quality and Grades

Item-specific (from Product Data)

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and their implications (general)

• If provided as “98%+” or “AR/Analytical” grade, expect lower levels of common impurities (e.g., bromide salts, hydrolyzed alcohols, or dibrominated byproducts). For “synthesis grade,” trace impurities may be higher but usually acceptable for routine transformations.
• UV/HPLC grade is uncommon for alkyl bromides; when specified, it indicates low UV-absorbing impurities suitable for detector baselines.
• Stabilizers: Alkyl bromides are generally shipped without stabilizers, but some lots may contain trace inhibitors or have been stored over molecular sieves to limit hydrolysis. Verify with the CoA if inhibitor-sensitive applications are planned (e.g., radical chemistry, polymerization initiation).

Quality control best practices

• Confirm identity by 1H/13C NMR (diagnostic –CH2Br singlets near 3.3–3.5 ppm; tert-butyl-equivalent methyl signals around 0.9–1.1 ppm), IR (C–Br stretch), and GC–MS (M, M+2, M+4 isotopic cluster for Br2).
• Water content, halide purity, and residual solvents: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Use profile (general, literature-based)

• Bifunctional alkylating agent: As an α,ω-dibromide, it serves in constructing linker segments, installing neopentyl spacers, and preparing difunctional derivatives (e.g., diols via halide–hydroxide displacement, though reaction is slow without activation).
• Protecting/“masking” strategy: The neopentyl motif is occasionally used to attenuate reactivity; C–Br activation may require special conditions, enabling stepwise transformations with orthogonality to more reactive halides elsewhere in a molecule.
• Polymer and materials chemistry: α,ω-dibromides can act as initiators or crosslinkers in radical or ionic processes; the neopentyl core imparts steric bulk and thermal stability to linkers.
• Rearrangement-prone solvolysis: Under strongly ionizing conditions (e.g., Ag+ salts, polar solvents), neopentyl bromides can undergo rearrangement via 1,2-methyl shifts, giving tert-alkyl cation-derived products; synthetic strategies may exploit or must avoid this pathway.

Practical tips

• Expect very poor SN2 rates at neopentyl positions; consider activation (e.g., convert to better leaving groups such as neopentyl triflates via halogen–lithium exchange followed by trapping, or employ neighboring-group strategies) or switch to radical or transition-metal-mediated pathways.
• Phase-transfer catalysis (PTC) and high-temperature polar aprotics can boost nucleophilic substitutions, but side reactions (elimination, rearrangement) may rise.
• For selective monofunctionalization, use large nucleophile excess at lower conversion and monitor closely (GC/GC–MS) to avoid over-reaction or difunctionalization.

Reaction Conditions

General guidance from literature (not product specifications; optimize per substrate and scale)

• SN2 displacement attempts
  • Solvent: DMSO, DMF, sulfolane, or acetonitrile to enhance nucleophilicity.
  • Nucleophiles: NaN3, NaI (Finkelstein), RS–/RSe–, CN–, or alkoxides; higher temperatures (80–140 °C) and extended times (hours to days) often required.
  • Additives: Phase-transfer catalysts (e.g., TBAB, TBAI) can accelerate, as can iodide co-catalysis.
• Solvolysis/rearrangement (use with caution)
  • Conditions: Polar solvents (HFIP, formic acid, TFE) or Ag+ salts (AgNO3 in MeOH/H2O) can promote ionization with rearrangement to tert-alkyl derivatives; useful if rearranged products are desired.
• Elimination (E2)
  • Bases: t-BuOK, KOtAmyl, DBU/DBN.
  • Solvents: t-BuOH, THF, DMSO. Elevated temperatures typically necessary.
• Radical pathways
  • Initiation: AIBN/peroxide or photoredox (e.g., Ir(ppy)3) under blue light; oxygen exclusion essential.
  • Solvents: Toluene, anisole, MeCN; reaction times from minutes (photoredox) to hours (thermal).
• Cross-electrophile coupling (Ni)
  • Catalysts/ligands: NiBr2(dme) or NiCl2 with bpy/phen ligands; Mn/Zn as terminal reductant.
  • Conditions: DMF/DMSO/MeCN, 20–80 °C; slow addition of halide can improve selectivity.

Notes

• Monitor by GC–MS to follow the characteristic Br isotopic patterns.
• Dry, oxygen-free conditions are advisable, particularly for radical or metal-catalyzed methods.

Safety and Handling

Item-specific (from Product Data)

• Storage conditions: Room temperature
• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

General safety guidance (consult the SDS for authoritative information)

• Likely hazards (literature/analog-based): Irritant to skin, eyes, and respiratory tract. Many low-molecular-weight alkyl bromides are harmful if inhaled, swallowed, or absorbed through skin. Handle as a potentially alkylating agent.
• PPE: Wear lab coat, chemical-resistant gloves (e.g., nitrile or Viton based on solvent compatibility), splash goggles; use in a fume hood to control vapors.
• Incompatibilities: Strong bases (risk of elimination), strong nucleophiles (vigorous substitution), finely divided metals, strong oxidizers. Avoid prolonged contact with moisture; hydrolysis is slow but possible over time.
• First aid overview: Move exposed person to fresh air for inhalation exposure; flush eyes/skin with water for at least 15 minutes upon contact; remove contaminated clothing. Seek medical attention if symptoms persist. If ingested, do not induce vomiting; seek medical attention immediately.
• Fire safety: Combustible organic liquid. Use CO2, dry chemical, or foam extinguishers. Heating can produce corrosive bromide-containing fumes (HBr, bromine); firefighters should wear SCBA.
• Waste: Collect halogenated waste in properly labeled containers; do not mix with incompatible reactive residues.
• Transport/storage notes: Keep tightly closed under inert headspace if possible; store away from bases and oxidants. Secondary containment recommended to prevent halogenated spill migration.

Solvent Selection

This product is an organic reactive building block (not used as a solvent). Solvent choice pertains to its use in reactions, extractions, and purifications.

General solvent compatibility and selection (literature/good practice)

• Polarity/miscibility: Hydrophobic; readily soluble in nonpolar and moderately polar organic solvents (hexanes, toluene, diethyl ether, MTBE, CPME, DCM, chloroform, THF, DMF, DMSO, acetonitrile). Essentially insoluble in water.
• For SN2 attempts (challenging due to neopentyl hindrance): Use polar aprotic media (DMSO, DMF, HMPA substitutes like DMI or sulfolane) to maximize nucleophile activity; strong nucleophiles and elevated temperature often required.
• For eliminations (E2): Strong, bulky bases (t-BuOK, DBN/DBU) in aprotic solvents (t-BuOH, THF, DMSO) favor dehydrohalogenation, though formation of stable alkenes is constrained by substitution pattern.
• For radical chemistry/ATRP-type initiations: Select low-protic, oxygen-free solvents (anisole, toluene, bulk monomer) and rigorously degas.

Comparison notes (general)

• Versus linear α,ω-dibromides (e.g., 1,3-dibromopropane), the neopentyl dibromide demands more activating conditions for substitution due to steric congestion and poor SN2 reactivity. Choose solvent systems that maximize nucleophile basicity/nucleophilicity and minimize ion pairing.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/practice)

• Container: Store in tightly sealed amber glass to minimize light exposure; halogenated organics can discolor upon prolonged light or heat.
• Atmosphere: Inert gas blanket (nitrogen or argon) is advisable for long-term storage to limit hydrolysis/oxidation; include a PTFE-lined cap.
• Moisture: Keep dry; although alkyl bromides hydrolyze slowly, moisture can introduce impurities over time.
• Stability: Typically stable at room temperature when protected from moisture and light. Avoid contact with strong bases and oxidizers in storage.
• Reconstitution: Not applicable—supplied as a neat liquid. If a solution is required, prepare freshly in a dry, oxygen-free solvent (e.g., anhydrous DCM, THF, toluene) immediately before use.
• Freeze–thaw: Not applicable; do not store in plasticizers-prone plastics for long periods to avoid permeation.

Research use note

• For research use only. Not for human or veterinary use.

Structure and Identity

Item-specific (from Product Data)

• SKU: D1368255
• Product name: 1,3-Dibromo-2,2-dimethylpropane
• CAS: 5434-27-5
• PubChem CID: 79491
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Computed/Literature values (for reference; not item specifications)

• Common synonym: 1,3-Dibromoneopentane; α,ω-dibromoneopentane
• Molecular formula (literature): C5H10Br2
• Molecular weight (literature): ~229.94 g/mol
• Canonical SMILES (literature): C(C)(C)(CBr)CBr (quaternary central carbon bound to two –CH3 and two –CH2Br groups)
• 2D structural description: A quaternary (tetrasubstituted) central carbon atom bearing two methyl substituents and two bromomethyl substituents (–CH2Br). The molecule is an α,ω-dibromide with significant neopentyl steric congestion adjacent to each C–Br bond; no rings, no heteroatoms other than bromine, and no stereocenters.

General chemistry notes

• Functional groups: Two primary alkyl bromides flanked by a neopentyl quaternary center; strong leaving groups with pronounced steric hindrance to backside attack (neopentyl effect).

Synthetic Utility

Functional profile

• Two primary C–Br bonds adjacent to a quaternary (neopentyl) carbon make this a highly hindered α,ω-dihalide. Each bromide is formally primary, but the adjacent steric wall gives markedly reduced SN2 reactivity (the “neopentyl effect”).

Representative transformations (literature)

• Nucleophilic substitution (challenging): Reaction with soft nucleophiles (thiolates, iodide, azide) in polar aprotic solvents at elevated temperatures or under PTC. Iodide (Finkelstein) can sometimes increase reactivity by in situ conversion to iodides.
• Elimination: Strong, hindered bases can effect dehydrohalogenation, though formation of internal alkenes from a neopentyl framework may be limited; competing rearrangements possible under solvolysis.
• Radical chemistry: Under AIBN/peroxide initiation or photoredox conditions, abstraction/halogen atom transfer can generate carbon-centered radicals for subsequent coupling or polymer end-group installation.
• Metal-mediated: Nickel- or copper-catalyzed cross-electrophile couplings and reductive couplings of unactivated alkyl bromides are emerging routes to forge C–C bonds; the neopentyl substrate may require higher catalyst loadings and carefully chosen ligands.

Strategic notes

• Use when a sterically demanding, hydrolytically robust spacer is desired; it can survive conditions that would rapidly consume more labile halides, enabling selective downstream activations.
• Consider alternative activation (convert to tosylate/mesylate or redox-active esters) if direct substitution proves intractable.

Target Specificity

Not applicable. This product is a small-molecule organic reagent, not a biological affinity reagent or antibody. No antigen/epitope/clone/isotype information pertains.