1,3-Dibromo-5,5-dimethylhydantoin

 CAS No.: 77-48-5  Cat No.: BP-501497  Purity: 97+% 4.5  

1,3-Dibromo-5,5-dimethylhydantoin is a brominating and linker-modifying reagent that can support PROTAC linker chemistry by enabling preparation of brominated intermediates or electrophilic attachment handles. Its hydantoin-based structure serves as a bromine-transfer source for functionalizing organic scaffolds that may later be converted into linker fragments, leaving-group-bearing intermediates, or ligand attachment points. In targeted degradation research, this product is useful in synthetic route development where controlled bromination is required before substitution, coupling, or further linker elaboration. Its value lies in expanding linker precursor functionalization strategies rather than directly determining degrader biological performance.

1,3-Dibromo-5,5-dimethylhydantoin

Structure of 77-48-5

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Category
PROTAC Linker
Molecular Formula
C5H6Br2N2O2
Molecular Weight
285.92
Appearance
Off-white to light yellow solid

* For research and manufacturing use only. Not for human or clinical use.

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Purity
97+%
Appearance
Off-white to light yellow solid
Storage
Powder, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
Synonyms
Dibromantine; n,n'-dibromodimethylhydantoin; 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione; Dibromo-5,5-dimethylhydantoin; Dibromo dimethyl hydantoin; Dibromantin; Dibromatin
Density
2.183 g/cm3
InChI Key
VRLDVERQJMEPIF-UHFFFAOYSA-N
InChI
InChI=1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
SMILES
CC1(C(=O)N(C(=O)N1Br)Br)C
1. 1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides
Fei-Fei Xu, Claney L Pereira, Peter H Seeberger Beilstein J Org Chem. 2017 Sep 22;13:1994-1998.doi: 10.3762/bjoc.13.195.eCollection 2017.
1,3-Dibromo-5,5-dimethylhydantoin (DBDMH), an inexpensive, non-toxic and stable reagent, is a competent activator of thioglycosides for glycosidic bond formation. Excellent yields were obtained when triflic acid (TfOH) or trimethylsilyl trifluoromethanesulfonate (TMSOTf) were employed as co-promoters in solution or automated glycan assembly on solid phase.
2. 1,3-Dibromo-5,5-dimethylhydantoin mediated oxidative amidation of terminal alkenes in water
Chunhua Ma, Guojie Fan, Ping Wu, Zhi Li, Yang Zhou, Qingjie Ding, Wei Zhang Org Biomol Chem. 2017 Nov 29;15(46):9889-9894.doi: 10.1039/c7ob02329d.
A variety of terminal alkenes were converted to the corresponding amides in yields of 25 to 86% in water via treatment with 1,3-dibromo-5,5-dimethylhydantoin, followed by reaction with molecular iodine and aq. NH3 (or amine) in one pot. This metal- and organic solvent-free protocol is not only suitable for styrene derivatives, but also, for the first time, works well on terminal aliphatic alkenes.
3. Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source
Lei Wang, Lele Zhai, Jinyan Chen, Yulin Gong, Peng Wang, Huilin Li, Xuegong She J Org Chem. 2022 Mar 4;87(5):3177-3183.doi: 10.1021/acs.joc.1c02906.Epub 2022 Feb 8.
A direct 1,2-dibromination method of alkenes is realized using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as a bromine source. This reaction proceeds under mild reaction conditions without the use of a catalyst and an external oxidant. Various sorts of alkene substrates are transformed into the corresponding 1,2-dibrominated products in good to excellent yields with broad substrate scope and exclusive diastereoselectivity. This method offers a green and practical approach to synthesize vicinal dibromide compounds.

1,3-Dibromo-5,5-dimethylhydantoin is a bromination reagent used in PROTAC linker precursor preparation rather than a spacer linker itself. It is useful for installing brominated handles that can later undergo substitution, coupling, or further functional-group conversion. The structure and reactivity are described below.

Structure: The reagent contains a dimethylhydantoin imide core bearing electrophilic nitrogen-bromine bonds. The cyclic imide stabilizes bromine-transfer reactivity and provides a defined, solid brominating reagent scaffold.

Reactivity: It can deliver electrophilic bromine to suitable alkene, aromatic, heteroaromatic, or activated aliphatic substrates depending on conditions. In PROTAC linker workflows, it is most appropriate for preparing brominated intermediates that subsequently participate in nucleophilic substitution or cross-coupling. Compatibility with oxidation-sensitive ligands should be assessed carefully.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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