85483-97-2

Basic information

• Product Name: (S)-(+)-1-BENZYLOXY-2-PROPANOL 97
• Synonyms: (S)-(+)-1-BENZYLOXY-2-PROPANOL 97;(2S)-1-benzyloxypropan-2-ol;2-Propanol,1-(phenylMethoxy)-, (2S)-;(S)-1-(benzyloxy)propan-2-ol;(S)-(+)-1-Benzyloxy-2-propanol 97%
• CAS NO: 85483-97-2
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.219
• Mol File: 85483-97-2.mol

Chemical Properties

• Boiling Point: 130-132℃ (14 Torr)
• Flash Point: 228 °F
• Appearance: /
• Density: 1.044 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00505mmHg at 25°C
• Refractive Index: n20/D 1.510(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.46±0.20(Predicted)
• CAS DataBase Reference: (S)-(+)-1-BENZYLOXY-2-PROPANOL 97(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1-BENZYLOXY-2-PROPANOL 97(85483-97-2)
• EPA Substance Registry System: (S)-(+)-1-BENZYLOXY-2-PROPANOL 97(85483-97-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 2
• Hazardous Substances Data: 85483-97-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-1-Benzyloxy-2-propanol is used as a reactant for the preparation of (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases (PMP derivatives). These PMP derivatives are important building blocks in the synthesis of nucleoside analogs, which are widely used as antiviral and anticancer agents. The chiral nature of (S)-(+)-1-Benzyloxy-2-propanol ensures the production of enantiomerically pure compounds, which is crucial for the desired biological activity and minimizing side effects.
Used in Chemical Synthesis:
(S)-(+)-1-Benzyloxy-2-propanol is used as a reactant in the synthesis of (S)-1-(benzyloxy)propan-2-yl 4-methylbenzenesulfonate by reacting with tosyl chloride in pyridine. (S)-(+)-1-BENZYLOXY-2-PROPANOL 97 can be further utilized in the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Lubricant Industry:
(S)-(+)-1-Benzyloxy-2-propanol is used as an effective antiwear agent in aviation turbine fuels, diesel fuels, and light mineral oil. Its antiwear properties help reduce friction and wear between moving parts, thereby extending the life of engines and machinery. This application is particularly important in high-performance and heavy-duty applications where reliability and longevity are critical.

InChI:InChI=1/C10H14O2/c1-9(11)7-12-8-10-5-3-2-4-6-10/h2-6,9,11H,7-8H2,1H3/t9-/m0/s1

Upstream product

• 22539-93-1 3-benzyloxypropanone 
• 4254-15-3 (S)-1,2-Propanediol 
• 100-39-0 benzyl bromide 
• 76946-21-9 (2S)-2-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol 
• 13807-91-5 benzyloxy-2-propanol 
• 100-52-7 benzaldehyde 
• 16088-62-3 (S)-Propylene oxide 
• 108-22-5 Isopropenyl acetate 
• 108-05-4 vinyl acetate 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 4039-82-1 Benzyl propargyl ether 
• 2930-05-4 (S)-benzyl glycidyl ether 

Downstream Products

• 221310-60-7 (S)-(+)-(2-benzyloxy-1-methyl)ethyl 4-nitrobenzenesulfonate 
• 128693-47-0 (R)-4-(Benzyloxy)-3-methylbutanoic acid 
• 64190-49-4 (S)-4-(Benzyloxy)-3-methylbutanoic acid 
• 138485-77-5 (S)-4-Benzyloxy-2-tert-butoxycarbonyl-3-methylbutansaeure-tert-butylester 
• 138485-77-5 (R)-4-Benzyloxy-2-tert-butoxycarbonyl-3-methylbutansaeure-tert-butylester 
• 13807-91-5 benzyloxy-2-propanol 
• 1395493-58-9 (S)-27-methyl-28-benzyloxy-2,5,8,11,14,17,20,23,26-nonaoxaoctacosane 
• 119233-39-5 (S)-(-)-(2-benzyloxy-1-methyl)ethyl 4-methyl-benzenesulfonate 

Relevant articles and documents

Double-hetero atom six-membered ring of synthetic method

The invention provides a double-hetero atom six-membered ring of synthetic method. The synthetic method comprises to alkyl substituted cyclopropane and benzyl alcohol and/or a the oxygen radical animal pen is mellow as the starting material, sequentially carry out the ring-opening reaction, a transesterification reaction, 1st sulfonylation reaction, alcoholysis reaction and the nucleophilic substitution reaction, catalytic hydrogenation reaction and 2nd sulfonylation reaction and forming ring reaction, to obtain the required double-hetero atom six-membered ring, a formula (1) of the structure shown. In order to price the comparatively cheap racemic alkyl substituted cyclopropane as raw materials, to participate in the ring-opening reaction, to obtain a ring opening product. Then under the action of the esterase, make the ring-opening products which is a transesterification reaction, disposable obtain the desired racemic compound. This avoids the traditional method of multi-step separation and purification in the synthesis step, shortens the synthetic route. In the above synthetic route also avoids the need to use some dangerous reagent, process more security, reducing waste generation, and save the process cost.

Piers' borane-mediated hydrosilylation of epoxides and cyclic ethers

We report the first diarylborane-catalysed hydrosilylation of epoxides and cyclic ethers. Mechanistic studies on the in situ generated Piers' borane (C6F5)2BH with hydrosilanes in the presence of an epoxide revealed that an alkyloxy(diaryl)borane (C6F5)2BOR is readily formed as a catalytically competent species for the outer-sphere hydrosilylation of epoxides and cyclic ethers.

Synthesis of (R)-propane-1,2-diol from lactides by dynamic kinetic resolution

The dynamic kinetic resolution (DKR) of rac-1-tert-butoxypropan-2-ol with isopropenyl acetate in the presence of Novozyme 435 and a ruthenium catalyst produces enantiomerically pure (R)-1-tert-butoxy-2-acetoxy-propane (>99.5 %ee) in a good yield. The product can be easily transformed into (R)-propane-1,2-diol without loss of stereoselectivity. Together with recently published procedures, the herein described DKR offers the possibility to use any lactide source as starting material for the production of (R)-propane-1,2-diol. The chiral diol may serve as the chiral building block for the synthesis of important enantiopure esters, like propylene carbonate, chiral polymers, etc.

Copper-catalyzed cross-coupling of nonactivated secondary alkyl halides and tosylates with secondary alkyl grignard reagents

Practical catalytic cross-coupling of secondary alkyl electrophiles with secondary alkyl nucleophiles under Cu catalysis has been realized. The use of TMEDA and LiOMe is critical for the success of the reaction. This cross-coupling reaction occurs via an SN2 mechanism with inversion of configuration and therefore provides a general approach for the stereocontrolled formation of C-C bonds between two tertiary carbons from chiral secondary alcohols.

Formation of higher-order structures of chiral poly(ethynylpyridine)s depending on size, temperature, and saccharide recognition

Amphiphilic 2,6-pyridylene ethynylene "meta-ethynylpyridine" polymers having chiral oligo(oxyethylene) side chains were developed as hosts for saccharide recognition. The polymers were prepared via a Sonogashira reaction and fractionated by gel permeation

Folding of a donor-containing ionene by intercalation with an acceptor

Cationic ionenes that bear electron-rich 1,5-dialkoxynaphthalene (DAN) units within the alkylene segment were allowed to interact with different types of electron-deficient, acceptor-containing molecules in an effort to realize intercalation-induced folding of the ionenes; the collapse of the chains was expected to occur in such a way that the donor and acceptor units become arranged in an alternating fashion. Several acceptor-bearing molecules were prepared by the derivatization of pyromellitic dianhydride and naphthalene tetracarboxylic dianhydride with two different oligoethylene glycol monomethyl ether monoamines. This yielded acceptor molecules with different water solubility and allowed the examination of solvophobic effects in the folding process. UV/Vis spectroscopic studies were carried out by using a 1:1 mixture of the DAN-ionenes and different acceptor molecules in water/DMSO solvent mixtures. The intensity of the charge-transfer (CT) band was seen to increase with the water content in the solvent mixture, thereby suggesting that the intercalation is indeed aided by solvophobic effects. The naphthalene diimide (NDI) bearing acceptor molecules consistently formed significantly stronger CT complexes when compared to the pyromellitic diimide (PDI) bearing acceptor molecules, which is a reflection of the stronger π-stacking tendency of the former. AFM studies of drop-cast films of different ionene-acceptor combinations revealed that compact folded structures are formed most effectively under conditions in which the strongest CT complex is formed. Know when to fold 'em: When coerced to collapse in a polar solvent in the presence of an electron-deficient amphiphilic folding agent, suitably modified ionenes with a symmetrically positioned electron-rich 1,5-dialkoxylnaphthalene (DAN) unit appear to form an accordion-type folded structure wherein the units are arranged in an alternating fashion (see picture). D=Donor; A=Acceptor. Copyright

Identification of absolute helical structures of aromatic multilayered oligo(m-phenylurea)s in solution

(Chemical Equation Presented) The oligomeric aromatic ureas bearing N,N′-dimethylated urea bonds such as 3 have aromatic multi-layered structure, based on the (cis,cis)-urea structure, and also have dynamic helical structure (all-R or all-S axis chirality) when the benzene rings are connected at the meta positions. The absolute helical structure of oligo(m-phenylurea)s were identified by the empirical and theoretical studies on the CD and vibrational CD (VCD) spectra. Thus, each enantiomer of the oligo(m-phenylurea)s 4 bearing a chiral N-2-(methoxyethoxyethoxy)propyl group were synthesized. Intense dispersion-type CD spectra of 4 were observed, which indicated the induction of handedness in the helical structure. In the VCD spectra of 4 in the film state, the signals due to the carbonyl and aromatic ring vibrations were seen with negative and positive values for compounds 4a and 4b, respectively. The calculations of both CD and VCD spectra of oligo(m-phenylurea)s 3 without any chiral N-substituent gave the same assignment about the axis chirality of 4. Thus, the absolute configurations of 4a and 4b are all-R and all-S structures, respectively. 2009 American Chemical Society.

Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety

Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene glycols having primary hydroxyl groups gave good yields of 17-crown-6 type ethers. Pentaethylene glycols with secondary hydroxyl groups rendered about the same amount of 17-crown-6 ethers and open chain dihydrogenphosphates in low yields. Tetraethylene glycols are reluctant to undergo macrocyclization with phosphorus oxychloride, especially the ones which contain secondary hydroxyl groups.

Hierarchical growth of chiral self-assembled structures in protic media

The location of nine chiral penta(ethylene oxide) side chains at the periphery of a C3-symmetrical hydrogen-bonded extended core gives rise to a thermotropic discotic liquid crystalline material that shows lyotropic phases in polar, protic media. The molecular stacks self-assemble in a reversible and hierarchical fashion, and specific and subtle solvent-molecule interactions together with the created hydrophobic microenvironment account for an unprecedented stabilization of a preferred handedness of the helical stacks by cooperative intermolecular interactions. The presence of either chirality or achirality at the supramolecular level in the stacks can be tuned by temperature and solvent as judged from circular dichroism spectroscopy. A hierarchical growth of the self-assembly is revealed using a variety of spectroscopic techniques and differential scanning calorimetry.

Phenoxathiin derivatives as inhibitors of monoamine oxidase

PCT No. PCT/US97/23486 Sec. 371 Date Mar. 11, 1999 Sec. 102(e) Date Mar. 11, 1999 PCT Filed Aug. 19, 1997 PCT Pub. No. WO98/12190 PCT Pub. Date Mar. 26, 1998The present invention provide phenoxathiin compounds useful in the prophylaxis and treatment of mental disorders, such as depression. The present invention also provides a method for treating a mammal having depression, anxiety or other conditions responsive to inhibition of MAO-A. A method of preparing the compounds of the present invention is also provided.