192775-97-6

Basic information

• Product Name: 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE
• Synonyms: 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE;2-[1-(4-BROMOPHENYL)ISOPROPYL]-4,4-DIMETHYL-1,3-OXAZOLINE;2-[1-(4-Bromophenyl)-1-methylethyl]-4,5-dihydro-4,4-dimethyloxazole;2-(2-(4-bromophenyl)propan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole;2-(2-(4-bromophenyl)propan-2-yl)-4,5-dihydro-4,4-dimethyloxazole;Oxazole, 2-[1-(4-bromophenyl)-1-methylethyl]-4,5-dihydro-4,4-dimethyl-;2-[2-(4-bromophenyl)propan-2-yl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole
• CAS NO: 192775-97-6
• Molecular Formula: C₁₄H₁₈BrNO
• Molecular Weight: 296.2
• EINECS: 1312995-182-4
• Mol File: 192775-97-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 346.1°C at 760 mmHg
• Flash Point: 163.1°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 0.000118mmHg at 25°C
• Refractive Index: 1.553
• PKA: 5.59±0.70(Predicted)
• CAS DataBase Reference: 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE(192775-97-6)
• EPA Substance Registry System: 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE(192775-97-6)

Safety Data

• Hazardous Substances Data: 192775-97-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE is used as a synthetic intermediate for the development of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, facilitating the synthesis of complex molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE is used as a potential building block for the design of new drugs. Its structural features may contribute to the development of molecules with specific therapeutic targets, potentially leading to the creation of novel pharmaceutical agents.
Used in Chemical Research:
2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE is utilized in chemical research as a subject for studying the properties and reactivity of complex organic molecules. Understanding its behavior in various chemical reactions can provide insights into the development of new synthetic methods and the discovery of new compounds with unique properties.
The specific applications and properties of 2-[1-(4-BROMOPHENYL)-1-METHYLETHYL]-4,4-DIMETHYL-4,5-DIHYDROOXAZOLINE are dependent on its chemical and physical characteristics, which can be influenced by factors such as purity and synthesis method. Further research and development are necessary to fully explore its potential uses and optimize its synthesis for various applications.

InChI:InChI=1/C14H18BrNO/c1-13(2)9-17-12(16-13)14(3,4)10-5-7-11(15)8-6-10/h5-8H,9H2,1-4H3

Synthetic route

4-bromo-α-(4,4-dimethyloxazolin-2-yl)toluene (176324-85-9) + methyl iodide (74-88-4) → 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6)

Conditions	Yield
With CH3I; potassium hexamethylsilazane; acetic acid In dichloromethane; water; isopropyl alcohol	4.61 g (0.0156 mmole, 84%)

2-(4-bromophenyl)-2-methylpropionic acid (32454-35-6) + 2-Amino-2-methyl-1-propanol (124-68-5) → 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-2-methylpropionic acid With thionyl chloride Stage #2: 2-Amino-2-methyl-1-propanol With thionyl chloride

(4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) → 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride 2: thionyl chloride View Scheme

4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) + 4-Chlorobutyronitrile (628-20-6) → 4-(4-chloro-1-oxobutyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-98-7)

Conditions	Yield
With iodine; magnesium In tetrahydrofuran	93%

4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) + tri-n-butyl(vinyl)tin (7486-35-3) → 4,4-dimethyl-2-(2-(4-vinylphenyl)propan-2-yl)-4,5-dihydrooxazole (1298022-53-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 70℃; Stille coupling; Inert atmosphere;	82%

4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-(4-chloro-1-oxobutyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-98-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran

oxirane (75-21-8) + 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) + 2-(4-piperidinyl)-1H-benzimidazole (38385-95-4) → 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-1-methylethyl]phenyl}ethyl)piperidin-4-yl]-1-(2-ethoxyethyl)-1H-benzimidazole

Conditions	Yield
Stage #1: oxirane; 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene With n-butyllithium Stage #2: 2-(4-piperidinyl)-1H-benzimidazole

oxirane (75-21-8) + 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) + p-toluenesulfonyl chloride (98-59-9) → 2-{4-[1-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-1-methylethyl]phenyl}ethyl p-toluenesulfonate

Conditions	Yield
With n-butyllithium

4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) → Bilastine

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium View Scheme

4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) → 2-methyl-2-[4'-(2''-hydroxyethyl)phenyl]propanoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tert-butyl methyl ether; hexane / 10 h / -60 °C / Large scale 1.2: 7 h / -60 - 20 °C / Large scale 2.1: phosphoric acid / water / 30 h / 90 °C / Large scale View Scheme

ethyleneglycol sulfate (1072-53-3) + 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene (192775-97-6) → C16H22NO5S(1-)

Conditions	Yield
Stage #1: 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene With n-butyllithium In hexane; tert-butyl methyl ether at -60℃; for 10h; Large scale; Stage #2: ethyleneglycol sulfate In hexane; tert-butyl methyl ether at -60 - 20℃; for 7h; Temperature; Solvent; Large scale;

Upstream product

• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 32454-35-6 2-(4-bromophenyl)-2-methylpropionic acid 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 176324-85-9 4-bromo-α-(4,4-dimethyloxazolin-2-yl)toluene 
• 74-88-4 methyl iodide 

Downstream Products

• 202189-76-2 2-{4-[1-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-1-methylethyl]phenyl}ethyl p-toluenesulfonate 
• 202189-78-4 Bilastine 
• 552301-45-8 2-methyl-2-[4'-(2''-hydroxyethyl)phenyl]propanoic acid 
• 1298022-53-3 4,4-dimethyl-2-(2-(4-vinylphenyl)propan-2-yl)-4,5-dihydrooxazole 
• 192775-98-7 4-(4-chloro-1-oxobutyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene 

Relevant articles and documents

A new and competitive synthetic approach for an antihistamine agent, bilastine

Efforts towards the novel synthesis of second generation non-sedating antihistamine drug, Bilastine was described in this manuscript. This competitive synthetic approach involves the convergent synthesis of Bilastine via simple Friedel-Crafts acylation as an alternate for earlier reported Stille and Suzuki couplings. The selectivity in Friedel-Crafts acylation reaction with chloro acetyl chloride on different substituted arenes was studied and employed the best conditions for the synthesis of Bilastine. Further synthetic approach involves the deoxygenation of aryl ketone to corresponding alkane in single step and finally provides Bilastine with 39% of improved overall yields, utilizing simple and cost-effective reagents, suitable for kilogram scale synthesis.

Process for production of piperidine derivatives

The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; R6 and R7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR8, SR8, and NR8R9; X3 is halogen, OR15, SR15, NR15R16, OSO2R15, or NHSO2R15; R5, R8, R9, R15, and R16 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and A is a substituent of its ring and is selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.