32707-89-4

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)benzyl alcohol
• Synonyms: 3,5-BIS(TRIFLUOROMETHYL)BENZYL ALCOHOL;(3,5-BIS-TRIFLUOROMETHYL-PHENYL)-METHANOL;[3,5-DI(TRIFLUOROMETHYL)PHENYL]METHANOL;3,5-DI(TRIFLUORO METHYL)BENZYLALCOHOL;TIMTEC-BB SBB000837;RARECHEM AL BD 0207;3,5-Bis(trifluromethyl)benzyl alcohol, 98%;3,5-Bis(trifluoromethyl)benzyl alcohol 98%
• CAS NO: 32707-89-4
• Molecular Formula: C₉H₆F₆O
• Molecular Weight: 244.13
• EINECS: 251-168-9
• Product Categories: Fluorides;Benzhydrols, Benzyl & Special Alcohols;Alcohol;Miscellaneous;Alcohols;C9 to C30;Oxygen Compounds;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Fluorine series
• Mol File: 32707-89-4.mol

Chemical Properties

• Melting Point: 53-56 °C(lit.)
• Boiling Point: 40°C 0,5mm
• Flash Point: 208 °F
• Appearance: white to light yellow crystal powder
• Density: 1.3954 (estimate)
• Vapor Pressure: 0.823mmHg at 25°C
• Refractive Index: 1.415
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.92±0.10(Predicted)
• BRN: 2055358
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)benzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)benzyl alcohol(32707-89-4)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)benzyl alcohol(32707-89-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 32707-89-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C9H6F6O/c10-8(11,12)6-1-5(4-16)2-7(3-6)9(13,14)15/h1-3,16H,4H2

Upstream product

• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 26107-80-2 3’,5’-bis(trifluoromethyl)acetophenone 
• 50-00-0 formaldehyd 
• 73852-19-4 3,5-bis-trifluromethylphenylboronic acid 
• 112981-69-8 3,5-bis(trifluoromethyl)phenylmagnesium bromide 
• 401-95-6 3,5-Bis(trifluoromethyl)benzaldehyde 
• 557-20-0 diethylzinc 
• 725-89-3 3,5-bistrifluoromethylbenzoic acid 

Downstream Products

• 159707-06-9 3,5-bis-(trifluoromethyl)benzyl trifluoromethanesulfonate 
• 374819-27-9 3,5-bis(trifluoromethyl)phenylmethyl 4-oxo-1-phenylcyclohexanecarboxylate 
• 345579-46-6 2-(3,5-bis(trifluoromethyl)benzyloxy)-1-phenylethanone 
• 75462-59-8 3,5-bis(trifluoromethyl)benzyl chloride 
• 1372925-86-4 3,5-bis(trifluoromethyl)benzyl chloroformate 
• 1448041-82-4 C₁₄H₁₄F₆N₂O₂ 
• 1448041-81-3 C₂₂H₂₀F₆N₂O₄ 
• 1448041-79-9 C₁₉H₂₂F₆N₂O₄ 
• 1448041-78-8 C₂₁H₂₉F₆NO₃Si 

Relevant articles and documents

Preparation process of high-purity 3,5-bis(trifluoromethyl)benzyl alcohol

The invention discloses a preparation method of high-purity 3,5-bis(trifluoromethyl)benzyl alcohol, and belongs to the technical field of organic synthesis. The method comprises the steps: reacting a Grignard reagent generated by reaction of 3,5-bis(trifluoromethyl)bromobenzene and magnesium metal with a reagent capable of introducing an aldehyde group to obtain 3,5-bis(trifluoromethyl)benzaldehyde, and then reducing 3,5-bis(trifluoromethyl)benzaldehyde into 3,5-bis(trifluoromethyl)benzyl alcohol through sodium borohydride. The purity of the product obtained by the technical route is more than 99.5%, the maximum single impurity is not more than 0.1%, and the requirement on high-purity 3,5-bis(trifluoromethyl)benzyl alcohol in the market is met. Raw materials required by the process are easy to obtain, reaction conditions are mild, safety is high, production cost is low, and the method is suitable for industrialization.

Tunable Ligand Effects on Ruthenium Catalyst Activity for Selectively Preparing Imines or Amides by Dehydrogenative Coupling Reactions of Alcohols and Amines

Selective dehydrogenative synthesis of imines from a variety of alcohols and amines was developed by using the ruthenium complex [RuCl2(dppea)2] (6 a: dppea=2-diphenylphosphino-ethylamine) in the presence of catalytic amounts of Zn(OCOCF3)2 and KOtBu, whereas the selective dehydrogenative formation of amides from the same sources was achieved by using another ruthenium complex, [RuCl2{(S)-dppmp}2] [6 d: (S)-dppmp=(S)-2-((diphenylphosphenyl)methyl)pyrrolidine], in the presence of catalytic amounts of Zn(OCOCF3)2 and potassium bis(trimethylsilyl)amide (KHMDS). Our previously reported ruthenium complex, [Ru(OCOCF3)2(dppea)2] (8 a), was the catalyst precursor for the imine synthesis, whereas [Ru(OCOCF3)2{(S)-dppmp}2] (8 d), which was derived from the treatment of 6 d with Zn(OCOCF3)2 and characterized by single-crystal X-ray analysis, was the pre-catalyst for the amide formation. Control experiments revealed that the zinc salt functioned as a reagent for replacing chloride anions with trifluoroacetate anions. Plausible mechanisms for both selective dehydrogenative coupling reactions are proposed based on a time-course study, Hammett plot, and deuterium-labeling experiments.

Palladium-catalyzed arylation of aldehydes with bromo-substituted 1,3-diaryl-imidazoline carbene ligand

The combination of 0 valent palladium precursor and bromo-substituted 1,3-diaryl-imidazoline carbene ligand precursor such as 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-imidazolinium chloride 1a exhibited high catalytic activity for the 1,2-addition of arylboronic acids to aldehydes including aqueous formaldehyde.

Palladium-catalyzed hydroxymethylation of aryl-and heteroarylboronic acids using aqueous formaldehyde

Cyclometallated NHC palladium complexes prepared from palladium(II) acetate [Pd(OAc)2] and unsymmetrical 1,3-diarylimidazolinium salts catalyzed the hydroxymethylation of (hetero)arylboronic acids using an excess amount of formalin to afford (hetero)arylm

PROCESS FOR THE PREPARATION 3,5-BIS(TRIFLUOROMETHYL)BENZYLALCOHOL

The present invention concerns a process for preparing 3,5bis(trifluoromethyl)benzylalcohol by formylation in a solvent of an appropriate organo-magnesium derivative with solid paraformaldehyde and optionally its conversion into a 3,5-bis(trifluoromethyl)benzyl halide.

HIGH-PURITY (FLUOROALKYL)BENZENE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.

(S)-(-)- and (R)-(+)-4-methyl-2-hydroxymethyl[2]paracyclo-[2](5,8)quinolinophane: Novel N,O-planar chiral catalysts for the enantioselective addition of diethylzinc to aldehydes

Novel planar chiral N,O-ligands derived from (R)-(+)and (S)-(-)-2,4-dimethyl[2]paracyclo[2](5,8)quinolinophane were synthesized and employed as catalyst in the enantioselective addition of diethylzinc to aromatic aldehydes. On the basis of the ee values, ranging from 30% to 75%, and the configuration of the obtained 1-phenyl-1-propanols a plausible structure of the transition state for the alkylation process of the aldehydes is discussed.

Process for the preparation of fluorine containing benzaldehydes

Fluor enthaltende Benzaldehyde werden in besonders vorteilhafter Weise erhalten, wenn man ein entsprechendes aromatisches S?urechlorid mit Wasserstoff in Gegenwart eines getr?gerten Palladium-Katalysators und eines Katalysator-Moderators umsetzt.

Process for preparing fluorine-containing benzaldehydes

The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.

Stereomutation of Methoxycarbenium Ions. 2. Experimental Evidence for an Inversion Process

The stereomutation about the C-O partial double bond of a series of 1-methoxy- (2/3) and 1-hydroxy-3-arylallyl cations (5) has been examined experimentally in strong acid solutions and theoretically by using HF/STO-3G calculations.The interconversions of cations 2/3 were shown to be intramolecular processes in FSO3H, CF3SO3H, and FSO3H/SbF5.The rate constants of the stereomutation of these cations, which were measured by using dinamic NMR methods, were found to depend on the substituents on the aryl ring.Apart from the case where the aryl ring bears two m-CF3 groups, 2g/3g, the rate constants for stereomutation are linearly related to ?+ (ρ = -2.37) with ? donors accelerating the reaction.The calculations performed for 5 show that the lowest energy pathway for isomerization involves rotation rather than inversion.They also reveal that ?-donor substituents on the aryl ring lower the barrier to rotation while raising the barrier to inversion.In both cases, the calculated barriers for substituted systems show a linear correlation with ?+.It is concluded that the preferred pathway for stereomutation of most of these 1-hydroxy and 1-methoxyallyl cations in both strong acid solution and the gas phase involves rotation.When the aryl ring bears very strongly electron-withdrawing groups, e.g., two CF3 groups in 2g/3g, the inversion pathway would seem to be preferred.This is the first example of methoxycarbenium ion which undergoes stereomutation by inversion rather than rotation