1,3-Dibromo-5,5-dimethylhydantoin

Size	Price	Stock	Quantity
--	$--	In stock

Size

Price

Stock

Quantity

$--

In stock

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

Canonical 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.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂