129254-76-8

Basic information

• Product Name: 1-BroMo-3-[3-(trifluoroMethyl)phenyl]propane
• Synonyms: 1-BroMo-3-[3-(trifluoroMethyl)phenyl]propane;1-(3-BroMopropyl)-3-(trifluoroMethyl)benzene
• CAS NO: 129254-76-8
• Molecular Formula: C₁₀H₁₀BrF₃
• Molecular Weight: 267.0856096
• Mol File: 129254-76-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 226.3 °C at 760 mmHg
• Flash Point: 106 °C
• Appearance: /
• Density: 1.44 g/cm³
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1-BroMo-3-[3-(trifluoroMethyl)phenyl]propane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BroMo-3-[3-(trifluoroMethyl)phenyl]propane(129254-76-8)
• EPA Substance Registry System: 1-BroMo-3-[3-(trifluoroMethyl)phenyl]propane(129254-76-8)

Safety Data

• Hazardous Substances Data: 129254-76-8(Hazardous Substances Data)

Usage

Uses

1-(3-Bromopropyl)-3-(trifluoromethyl)benzene is a key intermediate in the synthesis of Cinacalcet Hydrochloride (C441800). Cinacalcet Hydrochloride is the (R) enantiomer of Cinacalcet and is used in clinical trial in secondary hyperparathyroidism.

Upstream product

• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 294856-02-3 methyl 3-(3-(trifluoromethyl)phenyl)propanoate 
• 585-50-2 3-(3-trifluoromethylphenyl)propanoic acid 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 78573-45-2 3-[3-(trifluoromethyl)phenyl]propan-1-ol 

Downstream Products

• 226256-56-0 cinacalcet 
• 364782-34-3 cinacalcet hydrochloride 
• 1217809-88-5 N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride 
• 1271930-15-4 (R)-(1-naphthalen-1-ylethyl)-N,N-bis[3-(3-trifluoromethylphenyl)propyl]amine 
• 1245374-92-8 cinacalcet base 
• 1093172-43-0 [2,2-dimethyl-5-(2-{3-trifluoromethyl-4-[3-(3-trifluoromethylphenyl)propoxy]phenyl}ethyl)-1,3-dioxan-5-yl]carbamic acid t-butyl ester 
• 129255-25-0 1-(3-trifluoromethylphenyl)-4-(3-methyl-pyridin-4-yl)-pentane 
• 129255-24-9 1-(3-trifluoromethylphenyl)-4-(3-ethyl-pyridin-4-yl)-butane 

Relevant articles and documents

Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes

Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3

Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity

The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(–)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM3R). Compared to 1 and 5, (R)-(–)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(–)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(–)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.

Hydrochloric acid and intermediates [...] the synthetic method of the compound of

The invention provides a synthetic method of cinacalcet hydrochloride intermediate compound meta-trifluoro methyl phenylpropyl bromine and cinacalcet hydrochloride. According to the synthetic method, synthetic technology of intermediate compound meta-trifluoro methyl phenylpropyl bromine is optimized, so that yield and purity of meta-trifluoro methyl phenylpropyl bromine and cinacalcet hydrochloride are improved significantly, product quality is ensured, raw material utilization ratio is increased, and product cost is reduced effectively.