1,3-Dibromo-5,5-dimethylhydantoin

Modify Date: 2024-01-01 19:09:24

1,3-Dibromo-5,5-dimethylhydantoin Structure
1,3-Dibromo-5,5-dimethylhydantoin structure
Common Name 1,3-Dibromo-5,5-dimethylhydantoin
CAS Number 77-48-5 Molecular Weight 285.921
Density 2.2±0.1 g/cm3 Boiling Point 250.2±23.0 °C at 760 mmHg
Molecular Formula C5H6Br2N2O2 Melting Point 197-199 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 105.1±22.6 °C
Symbol GHS03 GHS05 GHS06 GHS09
GHS03, GHS05, GHS06, GHS09
Signal Word Danger

 Use of 1,3-Dibromo-5,5-dimethylhydantoin


1,3-Dibromo-5,5-dimethylhydantoin is an alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs[1].

 Names

Name 1,3-Dibromo-5,5-dimethylhydantoin
Synonym More Synonyms

 1,3-Dibromo-5,5-dimethylhydantoin Biological Activity

Description 1,3-Dibromo-5,5-dimethylhydantoin is an alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs[1].
Related Catalog
Target

Alkyl-Chain

In Vitro PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins[1].
References

[1]. An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562.

 Chemical & Physical Properties

Density 2.2±0.1 g/cm3
Boiling Point 250.2±23.0 °C at 760 mmHg
Melting Point 197-199 °C (dec.)(lit.)
Molecular Formula C5H6Br2N2O2
Molecular Weight 285.921
Flash Point 105.1±22.6 °C
Exact Mass 283.879578
PSA 40.62000
LogP 1.68
Vapour Pressure 0.0±0.5 mmHg at 25°C
Index of Refraction 1.622

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MU0686000
CHEMICAL NAME :
Hydantoin, 1,3-dibromo-5,5-dimethyl-
CAS REGISTRY NUMBER :
77-48-5
BEILSTEIN REFERENCE NO. :
0146024
LAST UPDATED :
199710
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C5-H6-Br2-N2-O2
MOLECULAR WEIGHT :
285.95
WISWESSER LINE NOTATION :
T5NVNV EHJ AE CE E1 E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GISAAA Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 36(10),108,1971
TYPE OF TEST :
LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
29 gm/m3/1H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-0281-0382
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
20 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - somnolence (general depressed activity) Skin and Appendages - hair
REFERENCE :
EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-0581-0382 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 mg/kg/17W-I
TOXIC EFFECTS :
Endocrine - evidence of thyroid hypofunction
REFERENCE :
GISAAA Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 36(10),108,1971 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83854 No. of Facilities: 21 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 124 (estimated)

 Safety Information

Symbol GHS03 GHS05 GHS06 GHS09
GHS03, GHS05, GHS06, GHS09
Signal Word Danger
Hazard Statements H272-H301-H314-H317-H410
Precautionary Statements Missing Phrase - N15.00950417-P210-P220-P280-P305 + P351 + P338-P370 + P378
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes C:Corrosive
Risk Phrases R22;R34;R50;R8
Safety Phrases S17-S26-S36/37/39-S45-S60-S61
RIDADR UN 3087 5.1/PG 2
WGK Germany 3
RTECS MU0686000
Packaging Group II
Hazard Class 5.1
HS Code 29332100

 Synthetic Route

~99%

1,3-Dibromo-5,5-dimethylhydantoin Structure

1,3-Dibromo-5,5...

CAS#:77-48-5

Literature: ALBEMARLE CORPORATION Patent: EP1250045 B1, 2003 ;

~%

1,3-Dibromo-5,5-dimethylhydantoin Structure

1,3-Dibromo-5,5...

CAS#:77-48-5

Literature: US2868787 , ;

~%

1,3-Dibromo-5,5-dimethylhydantoin Structure

1,3-Dibromo-5,5...

CAS#:77-48-5

Literature: Anales de la Asociacion Quimica Argentina (1921-2001), , vol. 41, p. 153

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles22

More Articles
Determination of selenium sulfide using 1,3-dibromo-5,5-dimethylhydantoin (DBH). Analytical methods of pharmacopeias with DBH in respect to environmental and economical concern Part 11.

J. Pharm. Biomed. Anal. 28(2) , 337-43, (2002)

USP 2000 (The United States Pharmacopeia, Rockville, MD, 24th ed., 2000, pp. 1514-1515) and PH. EUR. 1997 (European Pharmacopoeia, 3rd ed., Council of Europe, Strasbourg, 1997, p. 1459) dissolve selen...

Titrimetric determination of acetylenic hyponotics using organic brominating agents.

Pharm. Weekbl. Sci. 10(2) , 90-2, (1988)

A titrimetric method is described for the determination of three acetylenic hypnotics, namely ethchlorvynol, ethinamate, and methylpentynol carbamate, in bulk and in dosage forms. The method involves ...

Determination of iron limiting values according to PH. EUR. using 1,3-dibromo-5,5-dimethylhydantoin (DBH) instead of elemental bromine. Analytical methods of pharmacopoeias with DBH in respect to environmental and economical concern. Part 8.

Pharmazie 57(1) , 45-8, (2002)

PH. EUR. 2002 uses elemental bromine performing iron limit tests for maleic acid (iron 5 ppm) and titanium dioxide (iron 200 ppm). 1,3-Dibromo-5,5-dimethylhydantoin (DBH) can replace bromine water. Fo...

 Synonyms

N,N'-dibromo-5,5-dimethyl hydantoin
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-
DIBROMANTIN
3-DibroMo-5
DDH
1,3-dibromo-5,5-dimethyl-hydantoin
1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione
1,3-Dibromo-5,5-dimethyl hydantoin
EINECS 201-030-9
1,3-Dibromo-5,5-dimethylhydantoin
Bromotoin
dibromantine
BROMTOIN
DIBROMATIN
1,3-Dibromo-5
DBDMH
1,3-dibromo-4,4-dimethyl-2,5-dioxoimidazolidine
MFCD00003189
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