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Chemical structure of 1,2-Dibromododecane | 55334-42-4
CAS: 55334-42-4
SKU: S2849
1,2-Dibromododecane | SKU: S2849
synonyms: 1,2-Dibromododecane; Dodecane, 1,2-dibromo-; 1-Dodecene dibromide; α,β-Dibromododecane
Chemical structure of 1,2-Dibromododecane | 55334-42-4
1,2-Dibromododecane (CH3(CH2)9CHBrCH2Br, C12H24Br2) is the vicinal dibromide of a twelve-carbon chain: the compound obtained when bromine adds across the double bond of 1-dodecene. It has a molecular weight of 328.13 g/mol and one stereocentre at C2, and it is supplied as the racemate. Vicinal dibromides are versatile alkylating and elimination substrates, and the long, lipophilic dodecyl chain makes this one useful where hydrophobic products are wanted. Double dehydrobromination with a strong base such as sodium amide or potassium tert-butoxide gives 1-dodecyne, a terminal alkyne for click and Sonogashira chemistry; a single dehydrobromination gives 1-bromo-1-dodecene and related vinyl bromides; reductive debromination with zinc or sodium iodide regenerates 1-dodecene, which is why vicinal dibromides have long been used to protect or purify terminal alkenes. Substitution of the bromides with nitrogen, sulfur and oxygen nucleophiles leads to vicinal diamines, dithioethers and diols with a C10 tail. Sarchem Labs provides 1,2-dibromododecane (SKU S2849) for research and intermediate-synthesis customers. The assay and physical constants of the shipped lot are reported on the Certificate of Analysis, and a Safety Data Sheet accompanies each lot. Laboratory to bulk quantities can be quoted on request.
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Specifications

Linear FormulaCH3(CH2)9CHBrCH2Br
Chemical Name or Material1,2-Dibromododecane
Molecular Weight328.13 g/mol
SMILES StringCCCCCCCCCCC(CBr)Br
CAS Number55334-42-4
Empirical FormulaC12H24Br2
InChI1S/C12H24Br2/c1-2-3-4-5-6-7-8-9-10-12(14)11-13/h12H,2-11H2,1H3
InChI KeyHBRJEAWYCNGOSP-UHFFFAOYSA-N
PubChem CID185803
Functional GroupsAlkyl bromide (vicinal dibromide)
StereochemistryOne stereocentre (C2); racemic

Applications

No Application Found
Vinyl bromide synthesis: controlled mono-elimination gives 1-bromo-1-dodecene and 2-bromo-1-dodecene for cross-coupling studies.
Alkene protection and purification: reductive debromination with zinc dust or sodium iodide returns 1-dodecene after the alkene has been protected as the dibromide.
Vicinal difunctional compounds: displacement of the bromides gives 1,2-diamines, 1,2-dithioethers, 1,2-diazides and diols carrying a decyl chain, as intermediates for surfactants, ligands and lipid analogues.
Reference compound: a model long-chain vicinal dibromide for studies of alkene bromination, anti-elimination stereochemistry and halogenated-hydrocarbon analysis.

Product Description

What is 1,2-Dibromododecane?

1,2-Dibromododecane is a saturated twelve-carbon hydrocarbon with a bromine atom on each of the first two carbons. The formula is C12H24Br2 and the molecular weight is 328.13 g/mol. It is a vicinal (1,2-) dibromide, so the two bromines can be removed together as bromine (reductive debromination) or as two molecules of HBr (double elimination). It is a different compound from 1,12-dibromododecane (CAS 3344-70-5), the terminal α,ω-dibromide used as a chain-extending linker, and from 1-bromododecane (CAS 143-15-7).

Uses of 1,2-Dibromododecane

Synthetic chemists buy the compound as a precursor of C12 acetylenes and vinyl bromides and as a convenient route to vicinal functionalised dodecane derivatives. Teaching and method-development laboratories use long-chain vicinal dibromides to study the stereochemistry of bromine addition and of E2 elimination.

Buying and Handling Considerations

State the intended use and your purity requirement when you ask for a quote, and review the Certificate of Analysis of the lot, which reports the assay and the physical constants of the shipped material. Store in a tightly closed container in a cool, dry place away from light, strong bases, reducing metals and oxidisers. Alkyl bromides can release HBr slowly on heating or exposure to light, so keep the container closed, avoid contact with moisture and use glass or PTFE equipment.

Safety Information

  • Hazard Classification: A harmonised GHS classification has not been published for this compound.
  • Handling: Treat it as an alkylating, irritating organobromine compound: avoid contact with skin and eyes, avoid breathing vapour or mist, and keep it away from heat and ignition sources.
  • PPE: Chemical-resistant gloves, eye protection, protective clothing and, if vapour or mist may form, a respirator suited to organic vapours

The Safety Data Sheet of the shipped lot governs. Use only in a fume hood, do not release to drains and collect waste as halogenated organic waste.

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FAQs: 1,2-Dibromododecane

It is used to make 1-dodecyne and vinyl bromides by dehydrobromination, to protect and recover 1-dodecene, and to build vicinal diamine, dithioether and diol derivatives with a long alkyl chain.

No. 1,2-Dibromododecane (CAS 55334-42-4) has both bromines on adjacent carbons at one end of the chain. 1,12-Dibromododecane (CAS 3344-70-5) has one bromine at each end of the chain. Their reactions and uses are different.

The formula is C12H24Br2 and the molecular weight is 328.13 g/mol. The structure is CCCCCCCCCCC(CBr)Br.

By two successive E2 eliminations of HBr with a strong base, for example sodium amide in liquid ammonia or excess potassium tert-butoxide, followed by protonation of the acetylide.

Yes. Carbon 2 carries four different groups (H, Br, CH2Br and the decyl chain), so the molecule has one stereocentre. It is supplied as the racemate.

Keep it tightly closed in a cool, dry place away from light, strong bases and reducing metals.

Yes. Sarchem Labs provides a Certificate of Analysis and Safety Data Sheet with every lot of SKU S2849 and quotes bulk quantities on request.