3775-01-7

Basic information

• Product Name: 5-BENZYLIDENEHYDANTOIN
• Synonyms: (5E)-5-Benzylidene-2,4-imidazolidinedione;2,4-Imidazolidinedione, 5-(phenylmethylene)-;5-phenylmethylenehydantoin;5-BENZYLIDENEHYDANTOIN;TIMTEC-BB SBB007867;RARECHEM AP KH 0029;Benzylidene hydantoin;5-Benzylidendhydantoin
• CAS NO: 3775-01-7
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• Mol File: 3775-01-7.mol
• Article Data: 42

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.329g/cm³
• Refractive Index: 1.646
• CAS DataBase Reference: 5-BENZYLIDENEHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZYLIDENEHYDANTOIN(3775-01-7)
• EPA Substance Registry System: 5-BENZYLIDENEHYDANTOIN(3775-01-7)

Safety Data

• Hazardous Substances Data: 3775-01-7(Hazardous Substances Data)

Usage

General Description

5-Benzylidenehydantoin, also known as BZHI, is a white or off-white crystaline solid compound with the molecular formula C15H12N2O2. It is commonly used as a precursor in the synthesis of pharmaceuticals, such as antiviral and antitumor medications. BZHI is also utilized as a reactive intermediate in organic chemical reactions, particularly in the production of heterocyclic compounds. It is important to note that 5-Benzylidenehydantoin may pose health and safety hazards if not handled properly, and proper precautions should be taken when working with this chemical compound.

InChI:InChI=1/C10H8N2O2/c13-9-8(11-10(14)12-9)6-7-4-2-1-3-5-7/h1-6H,(H2,11,12,13,14)/b8-6-

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 100-52-7 benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 145693-93-2 5-benzylidene-2-methylsulfanyl-3,5-dihydro-imidazol-4-one 
• 583-46-0 5-benzylidene-2-thiohydantoin 
• 89990-65-8 2-{4-Oxo-5-[1-phenyl-meth-(Z)-ylidene]-4,5-dihydro-1H-imidazol-2-ylsulfanyl}-butyric acid ethyl ester 
• 38879-46-8 (Z)-4-benzylidene-2-methyl-5(4H)-oxazolone 
• 17606-70-1 (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 5817-49-2 (αRS,βRS)-N-[(benzyloxy)carbonyl]-β-hydroxy-phenylalanine 
• 74805-43-9 (Z)-N-benzyloxycarbonyldehydrophenylalanine azide 
• 74805-39-3 (Z)-2-benzyloxy-4-benzylideneoxazol-5-one 
• 5817-49-2 N-benzyloxycarbonyl-DL-erythro-β-phenylserine 
• 73087-17-9 2-benzyloxy-4-benzyl-DL-oxazol-5(4H)-one 

Downstream Products

• 100142-60-7 3-ethyl-5-benzylidene-imidazolidine-2,4-dione 
• 31113-72-1 N,N'-dimethyl-5-benzylidenehydantoin 
• 3530-82-3 5-benzyl-hydantoin 
• 117979-63-2 5-(p-chlorosulfonylbenzylidene)hydantoin 
• 156270-80-3 (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione 
• 156270-81-4 (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione 
• 150-30-1 Phenylalanine 
• 109754-06-5 (E)-5-(benzylidene)imidazolidine-2,4-dione 
• 114-76-1 sodium phenylphyruvate 
• 89-24-7 5-phenylimidazolidine-2,4-dione 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 100-52-7 benzaldehyde 
• 151559-54-5 (Z)-1-<2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl>-5-(phenylmethylene)-2,4-imidazolidinedione 
• 151559-53-4 (Z)-1-<2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl>-5-(phenylmethylene)-2,4-imidazolidinedione 

Relevant articles and documents

Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

Chemoenzymatic synthesis of L-3,4-dimethoxyphenyl-alanine and its analogues using aspartate aminotransferase as a key catalyst

In this study, a chemoenzymatic synthesis method for the production of L-3,4-dimethoxyphenyl-alanine and its analogues from phenylpyruvate derivatives was developed. The aspartate aminotransferase from Escherichia coli was engineered by error prone PCR and the improved variants were identified. When 3, 4-dimethoxy phenylpyruvate was added by fed-batch on a preparative scale, L-3,4-dimethoxyphenyl-alanine was formed in 95.4% conversion and > 99% ee with the best aspartate aminotransferase variant as the catalyst. This study provided an efficient method for the production of methoxy substituted phenylalanines using the engineered aspartate aminotransferase.

Discovery of novel UV-filters with favorable safety profiles in the 5-arylideneimidazolidine-2,4-dione derivatives group

Effective protection from the harmful effects of UV radiation may be achieved by using sunscreens containing organic or inorganic UV filters. The number of currently available UV filters is limited and some of the allowed molecules possess limitations such as systemic absorption, endocrine disruption properties, contact and photocontact allergy induction, and low photostability. In the search for new organic UV filters we designed and synthesized a series consisting of 5-benzylidene and 5-(3-phenylprop-2-en-1-ylidene)imidazolidine-2,4-dione (hydantoin) derivatives. The photoprotective activity of the tested compounds was confirmed in methanol solutions and macrogol formulations. The most promising compounds possessed similar UV protection parameter values as selected commercially available UV filters. The compound diethyl 2,20-((Z)-4-((E)-3-(4-methoxyphenyl)allylidene)-2,5-dioxoimidazolidine-1,3-diyl)diacetate (4g) was characterized as an especially efficient UVA photoprotective agent with a UVA PF of 6.83 ± 0.05 and favorable photostability. Diethyl 2,20-((Z)-4-(4-methoxybenzylidene)-2,5-dioxo-imidazolidine-1,3-diyl)diacetate (3b) was the most promising UVB-filter, with a SPFin vitro of 3.07 ± 0.04 and very good solubility and photostability. The main photodegradation products were geometric isomers of the parent compounds. These compounds were also shown to be non-cytotoxic at concentrations up to 50 μM when tested on three types of human skin cells and possess no estrogenic activity, according to the results of a MCF-7 breast cancer model.