70598-49-1

Basic information

• Product Name: Benzenamine, 4-bromo-2-ethyl-6-methyl-
• CAS NO: 70598-49-1
• Molecular Formula: C9H12BrN
• Molecular Weight: 214.105
• Mol File: 70598-49-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-bromo-2-ethyl-6-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-bromo-2-ethyl-6-methyl-(70598-49-1)
• EPA Substance Registry System: Benzenamine, 4-bromo-2-ethyl-6-methyl-(70598-49-1)

Safety Data

• Hazardous Substances Data: 70598-49-1(Hazardous Substances Data)

Upstream product

• 24549-06-2 6-ethyl-o-toluidine 

Downstream Products

• 943827-01-8 4-[4-(4-bromo-2-ethyl-6-methylphenylamino)pyrimidin-4-ylamino]benzonitrile 
• 635712-49-1 5-bromo-7-ethyl-1H-indazole 
• 1031417-71-6 5-bromo-3,7-dimethyl-1H-indazole 
• 943145-76-4 4-Bromo-2-ethyl-6-methylphenyldiazo-t-butyl sulfide 
• 1150644-73-7 4-amino-3-ethyl-5-methylbenzonitrile 
• 1031417-75-0 3,7-dimethyl-1H-indazole-5-carboxylic acid 
• 1062669-89-9 4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenol 
• 1062670-10-3 (S)-N,N-diethyl-4-(3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-6-methylpyridin-2-amine 
• 1062670-13-6 (S)-N-(3-(4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide 
• 1062670-07-8 (S)-1-amino-3-(4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propan-2-ol 
• 4909-95-9 3-ethyl-4-hydroxy-5-methyl-benzonitrile 
• 910635-33-5 3-ethyl-N,4-dihydroxy-5-methylbenzimidamide 
• 635712-51-5 C₂₁H₂₁N₃O₄ 

Relevant articles and documents

ARYL, HETEROARY, AND HETEROCYCLIC PHARMACEUTICAL COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, Formula IV, and Formula V, or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

Mechanistic insight into the formal [1,3]-migration in the thermal claisen rearrangement

The thermal formal [1,3]-sigmatropic shift of allyl aryl ethers has been studied in depth experimentally with the aid of the density functional theory (DFT) calculations of the B3LYP function. Three mechanistic possibilities, referred to as the radical, ionic, and concerted mechanisms, have previously been put forth to explain the thermal [1,3]-rearrangement process. However, the intercrossing and radical trapping experiments indicate the rearrangement is an intramolecular process. The computational studies reveal that the concerted C[1,3]-sigmatropic shift suffered from a higher energetic barrier to allow the rearrangement to proceed under the conditions used. However, a tandem O[1,3]-sigmatropic shift with a configuration inversion of the oxygen atom and [3,3]-sigmatropic shift (the Claisen rearrangement) is the most likely pathway for the formal [1,3] rearrangement. Furthermore, the rearrangement experiments with a designed optically active substrate and O[1,3]-sigmatropic shift examples verify the new cascade rearrangement. In addition, computational and experimental studies indicate that water molecule assists the proton shift during the isomerization. The combined methods provide the new insight into the mechanism of the thermal formal [1,3]-migration in the Claisen rearrangement and the novel O[1,3]-sigmatropic shift as well.

Practical and scalable synthesis of S1P1 receptor agonist ACT-209905

A practical and scalable route for the fast delivery of 12 kg of S1P 1 agonist (ACT-209905) has been developed. ACT-209905 is composed of an amino pyridine group, an oxadiazole spacer, a 2-ethyl-5-methylphenol moiety and a chiral 1-amino-2-propanol side chain. The convergent synthesis consists of 16 steps with 9 isolated intermediates and is chromatography-free. Key building blocks are accessed from low-cost starting materials, such as acetone, diethyl oxalate, cyanoacetamide, and 2-ethyl-5-methyl aniline. A Negishi coupling that was troubled by the use of metal reagents and concomitant metal waste streams has been replaced by a less expensive Guareschi-Thorpe reaction to build up an amino isonicotinic acid. The chiral 1-amino-2-propanol moiety was secured by selective ring-opening of an epoxide with lithium hexamethyldisilazide as an ammonia surrogate, thus omitting the notorious double alkylated byproduct.