Benzene, 1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)-

Base Information

• Chemical Name: Benzene, 1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)-
• CAS No.: 530441-95-3
• Molecular Formula: C11H9BrF6O
• Molecular Weight: 351.086
• DSSTox Substance ID: DTXSID80457098
• Nikkaji Number: J1.978.882B
• Wikidata: Q76416722
• Mol file: 530441-95-3.mol

Synonyms:530441-95-3;(R)-1-(1-(Bromomethoxy)ethyl)-3,5-bis(trifluoromethyl)benzene;Benzene, 1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)-;1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)benzene;SCHEMBL5205553;DTXSID80457098;NUIVKNWZGLUSHN-ZCFIWIBFSA-N;1,3-Bis(trifluoromethyl)-5-[(R)-1-(bromomethoxy)ethyl]benzene

Chemical Property of Benzene, 1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)-

Chemical Property:

• Vapor Pressure: 0.182mmHg at 25°C
• PSA: 9.23000
• LogP: 5.15420
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 349.97410
• Heavy Atom Count: 19
• Complexity: 268

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-[(1R)-1-(Bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OCBr
• Isomeric SMILES: C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OCBr

Technology Process of Benzene, 1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)-

There total 2 articles about Benzene, 1-[(1R)-1-(bromomethoxy)ethyl]-3,5-bis(trifluoromethyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol (368-63-8,68120-60-5,127852-28-2) → (R)-1-(1-(bromomethoxy)ethyl)-3,5-bis(trifluoromethyl)benzene (530441-95-3)

Guidance literature:

formaldehyd; (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol; at 20 ℃; for 0.333333h; Inert atmosphere;

With hydrogen bromide; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/anie.201303011

Reference yield:

3,5-bis(trifluoromethyl)phenyl methyl ketone (30071-93-3) → (R)-1-(1-(bromomethoxy)ethyl)-3,5-bis(trifluoromethyl)benzene (530441-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98.7 percent / chiral oxazaborolidine; BH₃*SMe₂ / CH₂Cl₂; toluene / -20 °C

2.1: Heating

2.2: hydrogen bromide

With dimethylsulfide borane complex; chiral oxazaborolidine; In dichloromethane; toluene;

DOI:10.1021/ol030104p

Reference yield: 95.2%

C14H19NO4 + (R)-1-(1-(bromomethoxy)ethyl)-3,5-bis(trifluoromethyl)benzene (530441-95-3) → C25H27F6NO5

Guidance literature:

With sodium carbonate; In N,N-dimethyl acetamide; at 0 ℃; Large scale;

upstream raw materials:

formaldehyd

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol

3,5-bis(trifluoromethyl)phenyl methyl ketone

Downstream raw materials:

(S)-5-[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxymethyl]-(R)-2-tert-butyl-3-methyl-5-phenylimidazolidin-4-one

(3R,5S,8aR)-5-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxymethyl]-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

(S)-2-amino-3-[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-N-methyl-2-phenylpropionamide

(R)-4-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxymethyl]-4-phenyl-imidazolidin-2-one

Refernces

• 1、 Yang, Xiao-Hui,Xie, Jian-Hua,Liu, Wei-Peng,Zhou, Qi-Lin. "Catalytic asymmetric hydrogenation of δ-ketoesters: Highly efficient approach to chiral 1,5-diols". supporting information. p. 7833 - 7836. Retrieved 2013/08/23.