1,2-Dibromobutane - ≥98% , CAS No.533-98-2

CAS: 533-98-2 Cat. No.: D102336 Formula: C₂H₅CH(Br)CH₂Br Molecular Weight: 215.91 Beilstein Registry Number: 1(4)266 EC Number: 208-581-4

GRADE & PURITY ≥98%

Synonyms

1,2-DIBROMOBUTANE | 1,2-dibromo-butane | NSC 6181 | Butane, 1,2-dibromo- | J-802009 | 8471F50VJI | DTXSID90870592 | 1,2-Dibromobutane, 97% | NSC6181 | NSC-6181 | SCHEMBL374715 | MFCD00000157 | 1,2-Butylene Bromide | AS-56865 | EN300-133999 | UNII-8471F50V

Storage

Room temperature

Shipped In

Normal

Overview

Mechanism of Co(II) (N,N′-disalicylidene-ethylenediamine) catalyzed reduction of 1,2-dibromobutane in DMF has been investigated by microelectrode voltammetry

Specifications

Synonyms

1,2-DIBROMOBUTANE | 1,2-dibromo-butane | NSC 6181 | Butane, 1,2-dibromo- | J-802009 | 8471F50VJI | DTXSID90870592 | 1,2-Dibromobutane, 97% | NSC6181 | NSC-6181 | SCHEMBL374715 | MFCD00000157 | 1,2-Butylene Bromide | AS-56865 | EN300-133999 | UNII-8471F50V

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

Pubchem Sid

488181184

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488181184

Canonical Smiles

CCC(CBr)Br

IUPAC Name

1,2-dibromobutane

InChIKey

CZWSZZHGSNZRMW-UHFFFAOYSA-N

INCHI

1S/C4H8Br2/c1-2-4(6)3-5/h4H,2-3H2,1H3

Isomeric SMILES

CCC(CBr)Br

WGK Germany

3

Molecular Weight

215.91

Beilstein

1(4)266

Reaxy-Rn

1731380

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1731380&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Class Organobromides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Class: 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
• Description: 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

Chemical and Physical Properties

• Solubility: alcohol: miscible(lit.)；water: insoluble(lit.)
• Refractive Index: 1.5141
• Flash Point(°F): 235.4 °F
• Flash Point(°C): >110°
• Boil Point(°C): 59-60 °C/20 mmHg
• Melt Point(°C): -65°C
• Molecular Weight: 215.910 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 215.897 Da
• Monoisotopic Mass: 213.899 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 28.700
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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

No standardized bioassay or immunoassay protocols apply to this chemical reagent. For synthetic applications, see the Reaction Conditions section for representative literature procedures and starting parameters. Always adapt conditions to your substrate, scale, and equipment, and consult the primary literature.

Biological Roles

This compound is a small halogenated hydrocarbon intended for chemical synthesis. It has no intrinsic biological role or metabolic function in cells under normal physiology.

• Literature context: low-molecular-weight dihalides can act as alkylating agents toward biomolecules in vitro, but 1,2-dibromobutane is not a metabolite and is used strictly as a laboratory reagent.
• Biodegradation and fate: brominated alkanes generally show limited biodegradability and may partition into organic phases; environmental behavior depends on conditions and is not typically relevant to bench-top biochemical assays.

No biological activity or roles are claimed for this item. Use is restricted to research and laboratory chemical synthesis.

Buffer Applications

Not typically applicable. 1,2-Dibromobutane is a hydrophobic organic reagent, not a buffering agent. It is not used to prepare aqueous buffer systems or to control pH. For relevant guidance, see the Reaction & Applications and Synthetic Utility sections for its role in organic synthesis.

Green Alternatives

Brominated reagents often raise concerns regarding persistence and toxicity. Selection of alternatives depends on the transformation (literature guidance):

• For alkylation chemistry:
  • Alternatives: 1-butanol derivatives (tosylate/mesylate), or 1-bromobutane (monohalide) if vicinal dihalide is unnecessary.
  • Trade-offs: Sulfonate esters avoid bromine byproducts but still require sulfonylating agents; reactivity may be lower than bromides.
• For generating 1-butyne:
  • Alternative routes: Dehydrohalogenation of 1,2-dichlorobutane (less hazardous than bromides) or elimination from appropriate di-tosylates; catalytic dehydrogenation of butenes (process-scale) is another route.
  • Trade-offs: Chlorides are less reactive, demanding harsher conditions; di-tosylates introduce sulfonate waste; dehydrogenation requires specialized catalysts/equipment.
• For radical processes:
  • Consider photoredox catalysis with redox-active esters (NHPI esters) or iodides; these may run under milder conditions and reduce brominated waste.

Comparison snapshot (literature)

• 1,2-dibromobutane: high reactivity; halogenated waste; potential aquatic toxicity.
• 1,2-dichlorobutane: lower reactivity; potentially lower toxicity; may need stronger bases/longer times.
• 1,2-di(p-toluenesulfonate)butane: non-halogenated leaving group; solid handling; often higher cost and additional synthesis step.

Select based on EHS profile, availability, and the minimum effective hazard to meet performance.

Pharmaceutical Uses

Not typically used as a pharmaceutical excipient or processing aid. 1,2-Dibromobutane is a reactive dihalide employed in organic synthesis. It is not listed here with any pharmacopeial monograph or formulation role. Any use must remain within non-clinical, research laboratory settings, in accordance with the Research Use Only notice.

Physical Properties

Item-specific (from Product Data)

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

Literature/general values (for reference only; not item specifications)

• Molecular formula: C4H8Br2; Molecular weight: 215.91 g/mol
• Physical state: Dense, colorless to pale-yellow liquid (literature)
• Boiling point: ~195–198 °C (literature, varies with source and pressure)
• Melting point: approximately −50 to −60 °C (literature)
• Density: ~1.95–2.02 g/mL at 20 °C (literature)
• Refractive index n20/D: ~1.53–1.56 (literature)
• Vapor pressure: low at ambient temperature (literature; increases substantially with heating)
• Solubility: poorly soluble in water; miscible with many organic solvents (e.g., ethers, aromatics, chlorinated solvents) (literature)
• Partition behavior: expected high hydrophobicity due to dihaloalkane structure (literature)

Notes

• The above numerical values are typical literature ranges and provided for planning only. Always consult the item’s CoA/Spec Sheet for definitive specifications applicable to this SKU.

Quality & Grades

Item-specific (from Product Data)

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

General guidance for this chemical class (literature/industry practice)

• For alkyl dihalides used in synthesis, common quality descriptors include: “Reagent grade” (suitable for general synthetic use), “Purified/distilled” (lower residual halides/water), and “High-purity” (low UV-absorbing and metal contaminants for sensitive applications). Absent a stated grade, treat as a standard research reagent.
• Trace impurities of HBr, water, or lighter/heavier brominated homologues can affect base-promoted eliminations and organometallic formations. Drying (e.g., over molecular sieves) and, if necessary, distillation under inert atmosphere can improve reproducibility.
• If UV transparency, residual metals, or halide assay are critical, request the CoA/Spec Sheet for exact specifications and analytical methods (GC, Karl Fischer, ICP, UV-Vis).

Reaction & Applications

1,2-Dibromobutane is a versatile vicinal dihaloalkane used as an alkylating and elimination substrate in synthesis (literature):

• Double dehydrohalogenation to alkynes: With strong bases (e.g., NaNH2 in liquid NH3 or THF), vic-dibromides undergo successive E2 eliminations to give 1-butyne. Terminal alkynes may be further manipulated (e.g., deprotonation to form acetylides for C–C bond formation).
• Reductive dehalogenation to alkenes: Zn, Mg, or catalytic Ni/Cu in alcohols or aprotic solvents convert vic-dibromides to butenes (E/Z mixtures). Choice of metal/conditions tunes selectivity.
• Formation of organomagnesium reagents: Stepwise insertion of Mg into the C–Br bonds can afford bromomagnesio derivatives; the secondary C–Br may be less prone than the primary. Control of temperature and order of addition is important to avoid Wurtz coupling.
• Nucleophilic substitution/alkylation: The primary bromide (C1) undergoes SN2 with soft nucleophiles (e.g., thiolates, cyanide, azide) to furnish 2‑substituted‑1‑bromobutanes, enabling sequential functionalization.
• Radical chemistry: Under photolysis or radical initiators, C–Br homolysis enables radical additions or coupling; proper inhibitors and light control are required to limit side reactions.

Practical tips (literature):

• For eliminations, favor strong, non-nucleophilic bases and lower temperatures initially to manage exotherms; employ excess base for full conversion to alkyne.
• For SN2, use polar aprotic solvents, modest temperatures, and anhydrous conditions. Monitor by GC or 1H NMR to distinguish mono- vs. di-substituted products.

Reaction Conditions

General conditions from literature (guidance only; optimize per system):

• Double dehydrohalogenation to 1-butyne:
  • Reagents: 2–3 equiv NaNH2; solvents: liquid NH3, THF, or glyme; temperature: −78 to 25 °C initiation, then allow to warm; typical times: 1–4 h. Quench with NH4Cl. Side products: butenes if base is insufficient.
• Reductive elimination to butenes:
  • Reagents: Zn dust (2–4 equiv) or Mg; solvents: EtOH, acetonitrile, or THF; temperature: reflux (EtOH) or rt–reflux; times: 2–12 h. Catalytic NiCl2 or Cu salts can accelerate and tune E/Z outcome.
• SN2 substitution at C1:
  • Nucleophiles: NaN3, KSCN, NaCN, thiolates; solvents: DMF, DMSO, MeCN; temperature: 0–80 °C depending on nucleophile strength; times: 1–24 h. Use excess nucleophile to minimize competing E2 at C2.
• Grignard/metal insertion (caution):
  • Reagents: Mg turnings (1–2 equiv per C–Br); solvent: anhydrous Et2O or THF; temperature: 0–25 °C; control addition to limit coupling/polymerization. Initiators (I2, dibromoethane) may be used judiciously.

Monitoring and workup:

• Track progress by GC-FID or 1H NMR (disappearance of CH2Br and CHBr resonances). Neutralize residual base/metal carefully; halogenated wastes must be segregated per EHS policy.

Safety & Handling

Item-specific (from Product Data)

• GHS signal word, hazard statements, pictograms, and classification: Not specified for this item; refer to the SDS for authoritative safety information.

General safety guidance (literature/analogous materials; not item-specific)

• Likely hazards for vicinal dibromoalkanes include: skin/eye irritation, harmful if swallowed/inhaled, and environmental aquatic toxicity. Avoid breathing vapors and prevent release to the environment.
• Reactivity considerations: may undergo dehydrohalogenation with strong base; reacts with active metals (e.g., Zn, Mg) to give alkenes or organometallics. Avoid contact with strong bases, strong nucleophiles, powdered metals, and strong oxidizers unless intended.
• Peroxide formation: not an ether—peroxide formation is not a typical concern, but general good practice is to store away from light/heat.
• Incompatibilities: strong bases, strong oxidants, finely divided metals, and moisture when organometallic formation is not desired.

PPE and handling

• Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles; handle in a fume hood to control vapors.
• First aid (overview; consult SDS): rinse skin/eyes with water for ≥15 min upon contact; if inhaled, move to fresh air; if ingested, do not induce vomiting—seek medical attention.

Always consult the product SDS and your institutional EHS guidance before use.

Solvent Selection

This product is a reactive organic liquid used as a reagent, not as a solvent. Solvent selection therefore pertains to its use in reactions involving 1,2-dibromobutane.

• Polarity/behavior (general): nonpolar to weakly polar halogenated hydrocarbon; immiscible with water; miscible with many organic solvents (ethers, hydrocarbons, aromatics, chlorinated solvents) (literature).
• Typical media choices by transformation (literature):
  • Base-promoted eliminations to alkynes: polar aprotic solvents (DMSO, DMF) or alcoholic media (EtOH) with strong base; for double dehydrohalogenation to 1-butyne, liquid ammonia or THF with NaNH2 is classic.
  • Reductive dehalogenation to alkenes: protic (EtOH) or aprotic (THF) solvents with Zn, Mg, or Ni catalysts; avoid water.
  • Nucleophilic substitutions at C1/C2: polar aprotic solvents (MeCN, DMF, DMSO) enhance SN2 reactivity at the primary carbon.
• Practical tips: Select solvents that solubilize both the substrate and base/metal; rigorously exclude water for organometallic or strong-base chemistry; choose higher-boiling media when heating is required.

If you require it as a medium, consider alternative solvents; 1,2-dibromobutane is seldom used as a bulk solvent.

Storage & Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipping: Normal.

General guidance (literature/practice)

• Container: Store in a tightly sealed amber glass bottle to minimize light exposure and volatilization.
• Atmosphere: Inert gas blanket (e.g., nitrogen) is advisable after opening for moisture- and oxidation-sensitive applications, though the compound is generally stable.
• Avoid: Strong bases, oxidizers, and reactive metals in storage areas. Keep away from heat sources.
• Reconstitution: Supplied neat as a liquid; no reconstitution required. If solid impurities or phase separation are observed, warm gently to ambient and mix thoroughly before use.
• Handling after opening: To ensure consistent reactivity, consider drying over 3 Å molecular sieves (activated) if trace moisture pickup is suspected. For the most sensitive reactions, distill under reduced pressure immediately prior to use.

Refer to the CoA/Spec Sheet and SDS for container compatibility and recommended shelf life.

Structure & Identity

Item-specific (from Product Data)

• SKU: D102336
• Product name: 1,2-Dibromobutane
• CAS: 533-98-2
• PubChem CID: 10792
• InChIKey (as provided): 57953
• Storage: Room temperature
• Shipped: Normal
• Research use: For research use only

Computed/Literature (general reference; not item-specific)

• Molecular formula: C4H8Br2 (literature)
• Molecular weight: 215.91 g/mol (literature)
• SMILES (non-stereospecific): CC(Br)CCBr (literature)
• InChI (standard): InChI=1S/C4H8Br2/c1-4(5)2-3-6/h4H,2-3H2,1H3 (literature)
• Structural features: vicinal dihaloalkane (two bromine atoms on adjacent C1 and C2 of a butane chain); contains one secondary C–Br (at C2) and one primary C–Br (at C1); chiral center possible at C2 (commercial material typically racemic unless specified).
• 2D description: a four‑carbon unbranched chain where the terminal carbon (C1) bears Br (–CH2Br), the adjacent carbon (C2) bears Br and a methyl substituent (–CH(Br)–), followed by a –CH2–CH3 tail.

Synthetic Utility

Functional elements and reactivity (literature):

• Two C–Br bonds of differing substitution (primary and secondary) enable chemoselective transformations: SN2 at C1 vs. slower displacement at C2.
• Vic-dihalide motif supports sequential eliminations to give alkenes and, with strong base, alkynes (1-butyne from this substrate).
• Reactivity with metals (Zn, Mg) facilitates formation of alkenes or organometallic intermediates; careful control avoids over-reduction or Wurtz-type coupling.

Named/representative transformations (literature):

• Double E2 dehydrohalogenation to terminal alkynes using NaNH2 (classic route from vic-dihalides).
• Reformatsky-related and Barbier-type variants where in situ metal insertion (e.g., Zn) yields reactive species that can add to electrophiles (dependent on conditions and substrate compatibility).
• Radical-mediated atom transfer or photolytic C–Br homolysis for carbon–carbon or carbon–heteroatom bond construction.

Retrosynthetic value:

• Serves as a masked C≡C synthon via vicinal dihalide → alkyne strategy.
• Functions as a bifunctional alkylating handle enabling stepwise installation of two distinct groups along a butyl backbone.

Practical considerations:

• Anhydrous conditions benefit SN2 and organometallic paths; base choice dictates E2 vs substitution. Monitor by GC to manage isomer distributions (E/Z alkenes) and ensure full double elimination when targeting alkynes.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, ligand, or probe). No antigen/epitope or species specificity applies.