(S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl chloride

Base Information

• Chemical Name: (S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl chloride
• CAS No.: 20445-33-4
• Molecular Formula: C10H8 Cl F3 O2
• Molecular Weight: 252.621
• Hs Code.: 2918990090
• European Community (EC) Number: 633-847-5
• UNII: 472VA70UL4
• DSSTox Substance ID: DTXSID30942621
• Nikkaji Number: J401.974A
• Wikidata: Q27258995
• Mol file: 20445-33-4.mol

Synonyms:(+)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride;(-)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride

Chemical Property of (S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl chloride

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Boiling Point: 213-214 °C(lit.)
• Flash Point: 194 °F
• PSA: 26.30000
• Density: 1.35 g/mL at 25 °C(lit.)
• LogP: 2.85600
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly miscible with water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 252.0164917
• Heavy Atom Count: 16
• Complexity: 261

Purity/Quality:

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

(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(C1=CC=CC=C1)(C(=O)Cl)C(F)(F)F
• Isomeric SMILES: CO[C@](C1=CC=CC=C1)(C(=O)Cl)C(F)(F)F
• Uses: Resolution of enantiomers primarily of alcohols and amines. (S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride is used in the preparation of natural products and pheromones. It is also employed as a derivatization enantiomeric purity reagent used for the determination of enantiomeric purity of alcohol and amines by gas chromatography. Used in the synthesis of natural products and pheromones.

Technology Process of (S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl chloride

There total 20 articles about (S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoyl chloride 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: 100.0%

R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2) → (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4)

Guidance literature:

With Chloro-oxo-acetic acid; N,N-dimethyl-formamide; In hexane; at 20 ℃; for 24h;

DOI:10.1021/np800294q

Reference yield: 100.0%

(S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) → (R)-methoxytrifluoromethylphenylacetyl chloride (20445-33-4,39637-99-5)

Guidance literature:

With Chloro-oxo-acetic acid; N,N-dimethyl-formamide; In hexane; at 20 ℃; for 24h;

DOI:10.1021/np800294q

Reference yield: 80.8%

(+)-MTPA (20445-31-2) → (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (20445-33-4)

Guidance literature:

With thionyl chloride; sodium chloride; at 90 ℃; for 50h;

DOI:10.1016/S0031-9422(99)00451-3

upstream raw materials:

R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid

(S)-Mosher acid

2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-2-enone

(RS)-metoprolol

Downstream raw materials:

(2S,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

(R)-MTPA-(S)-Ala-OH

Refernces

• 1、 Rieser,Hui,Rupprecht,Kozlowski,Wood,McLaughlin,Hanson,Zhuang,Hoye. "Determination of absolute configuration of stereogenic carbinol centers in annonaceous acetogenins by 1H- and 19F-NMR analysis of Mosher ester derivatives". . p. 10203 - 10213. Retrieved 1992.
• 2、 Gelderblom, Wentzel C. A.,Sewram, Vikash,Shephard, Gordon S.,Snijman, Petra W.,Tenza, Kenny,Van Der Westhuizen, Liana,Vleggaar, Robert. "Structure and natural occurrence of stereoisomers of the fumonisin B series mycotoxins". . p. 4388 - 4394. Retrieved 2007.
• 3、 Jung, Michael E.,Dwight, Timothy A.,Vigant, Frederic,stergaard, Michael E.,Swayze, Eric E.,Seth, Punit P.. "Synthesis and duplex-stabilizing properties of fluorinated N-methanocarbathymidine analogues locked in the C3'-endo conformation". . p. 9893 - 9897,5. Retrieved 2014.
• 4、 Ohtsuka,Itezono,Nakayama,Sakai,Shimma,Yokose,Seto. "Hispidospermidin, a novel phospholipase C inhibitor produced by Chaetosphaeronema hispidulum (Cda) Moesz NR 7127: II - Isolation, characterization and structural elucidation". . p. 6 - 15. Retrieved 1994.
• 5、 Khalaf, Abedawn I.,Linaza, Sabin,Pitt, Andrew R.,Stimson, William H.,Suckling, Colin J.. "On the specificity of reactions catalysed by the antibody H11". . p. 489 - 495. Retrieved 2000.
• 6、 Hashimoto, Toshihiro,Irita, Hiroshi,Tanaka, Masami,Takaoka, Shigeru,Asakawa, Yoshinori. "Pinguisane and dimeric pinguisane-type sesquiterpenoids from the Japanese liverwort Porella acutifolia subsp. tosana". . p. 593 - 604. Retrieved 2000.
• 7、 Luzzio, Frederick A.,Duveau, Damien Y.. "Enzymatic resolution of the 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane (1,8-cineole) system". . p. 1173 - 1180. Retrieved 2002.
• 8、 Rey-Tarrío, Francisco,Rodríguez, Rafael,Qui?oá, Emilio,Riguera, Ricardo,Freire, Félix. "Photochemical Electrocyclization of Poly(phenylacetylene)s: Unwinding Helices to Elucidate their 3D Structure in Solution". . p. 8095 - 8103. Retrieved 2021.
• 9、 Dhanjee, Heemal H.,Kobayashi, Yutaka,Buergler, Jonas F.,McMahon, Travis C.,Haley, Matthew W.,Howell, Jennifer M.,Fujiwara, Koichi,Wood, John L.. "Total Syntheses of (+)- and (-)-Tetrapetalones A and C". . p. 14901 - 14904. Retrieved 2017.
• 10、 Gui, Honggang,Liu, Junyang,Song, Liankai,Hui, Chunngai,Feng, Junmin,Xu, Zhengshuang,Ye, Tao. "Cross-metathesis approach for stereocontrolled synthesis of the C1-C15 fragment of rhizopodin". . p. 138 - 142. Retrieved 2014.