7261-97-4

Basic information

• Product Name: Dantrolene
• Synonyms: DANTRILENE;1-{(5-(4-NITROPHENYL)-2-FURANYL)METHYLENE}AMINO-2,4-IMIDAZOLIDENEDIONE;1-[[[5-(4-Nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidinedione;1-[5-(4-Nitrophenyl)-2-furylmethyleneamino]imidazolidine-2,4-dione;C06939;Dantrolene (200 mg)
• CAS NO: 7261-97-4
• Molecular Formula: C₁₄H₁₀N₄O₅
• Molecular Weight: 314.256
• EINECS: 230-684-8
• Mol File: 7261-97-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 279-280°
• Boiling Point: 453.94°C (rough estimate)
• Appearance: /
• Density: 1.3452 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• PKA: 7.68±0.10(Predicted)
• CAS DataBase Reference: Dantrolene(CAS DataBase Reference)
• NIST Chemistry Reference: Dantrolene(7261-97-4)
• EPA Substance Registry System: Dantrolene(7261-97-4)

Safety Data

• Hazardous Substances Data: 7261-97-4(Hazardous Substances Data)

Usage

Uses

Dantrolene acts as a skeletal muscle relaxant through inhibition of Ca2+ release through ryanodine receptor channels.

Definition

ChEBI: The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin.

Therapeutic Function

Muscle relaxant

General Description

Crystals (in aqueous DMF).

Air & Water Reactions

Slightly water soluble. Dantrolene may be sensitive to heat and air .

Health Hazard

SYMPTOMS: When ingested, symptoms of exposure may include drowsiness, dizziness, weakness, general malaise, fatigue, diarrhea, constipation, gastrointestinal bleeding, anorexia, abdominal cramps, hepatitis, speech disturbance, seizure, headache, light-headedness, insomnia, tachycardia, phlebitis, mental depression, mental confusion, nervousness, abdominal hair growth, rash, sweating, backache, chills and fever.

Fire Hazard

Flash point data for Dantrolene are not available. Dantrolene is probably combustible.

InChI:InChI=1/C14H10N4O5/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22/h1-7H,8H2,(H,16,19,20)/b15-7+

Upstream product

• 6301-02-6 1-aminohydantoin 
• 7147-77-5 5-(4-nitrophenyl)-2-furaldehyde 
• 2827-56-7 1-aminohydantoin hydrochloride 
• 98-01-1 furfural 
• 100-00-5 4-chlorobenzonitrile 
• 14663-23-1 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 62452-00-0 3-<3-(N-tert-butoxycarbonylamino)-1-oxopropyl-1-<<5-(4-nitrophenyl)-2-furanyl>methylene>amino>-2,4-imidazolidinedione 
• 14663-23-1 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt 

Relevant articles and documents

SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF DANTROLENE AND SODIUM DANTROLENE

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Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions

With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.

Continuous Visible-Light Photoflow Approach for a Manganese-Catalyzed (Het)Arene C?H Arylation

Manganese photocatalysts enabled versatile room-temperature C?H arylation reactions by means of continuous visible-light photoflow, thus allowing for efficient C?H arylations in 30 minutes with ample scope. The robustness of the manganese-catalyzed photoflow strategy was shown by visible light-induced gram-scale synthesis, clearly outperforming the batch performance.