18776-12-0

Basic information

• Product Name: 3-CHLORO-1-PHENYL-1-PROPANOL
• Synonyms: 3-CHLORO-1-PHENYLPROPANOL;rac 3-Chloro-1-phenylpropanol;BenzeneMethanol, α-(2-chloroethyl)-
• CAS NO: 18776-12-0
• Molecular Formula: C₉H₁₁ClO
• Molecular Weight: 170.63604
• EINECS: 1592732-453-0
• Product Categories: Benzene derivatives;Aromatics;Intermediates
• Mol File: 18776-12-0.mol
• Article Data: 51

Chemical Properties

• Melting Point: 31.0 to 36.0 °C
• Boiling Point: 116°C/4mmHg(lit.)
• Flash Point: 132 °C
• Appearance: /
• Density: 1.149 g/cm³
• Refractive Index: 1.54
• Storage Temp.: 0-10°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 13.92±0.20(Predicted)
• CAS DataBase Reference: 3-CHLORO-1-PHENYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-1-PHENYL-1-PROPANOL(18776-12-0)
• EPA Substance Registry System: 3-CHLORO-1-PHENYL-1-PROPANOL(18776-12-0)

Safety Data

• Hazardous Substances Data: 18776-12-0(Hazardous Substances Data)

Usage

Uses

An intermediate of racemic Atomoxetine.

Upstream product

• 19434-65-2 3-chloropropanaldehyde 
• 871351-43-8 methanesulfonic acid 3-chloro-1-phenyl-propyl ester 
• 71-43-2 benzene 
• 936-59-4 3-chloropropiophenone 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 104-52-9 phenylpropyl chloride 
• 1332887-24-7 3-chloro-1-phenylpropyl nitrate 
• 6323-18-8 2-chloropropiophenone 
• 34841-35-5 3'-chloro-propiophenone 
• 7732-18-5 water 
• 14155-36-3 (+/-)-(1,3-dichloropropyl)benzene 

Downstream Products

• 5554-64-3 N,N-dimethyl-3-hydroxy-3-phenylpropylamine 
• 156370-61-5 3-(isopropylamino)-1-phenyl-1-propanol 
• 952-51-2 1-phenyl-3-(piperidin-1-yl)propan-1-ol 
• 4446-91-7 3-chloro-1-methoxy-1-phenylpropane 
• 22165-41-9 1-Phenyl-3-chlor-propyl-methoxymethyl-ether 
• 23518-28-7 1-Phenyl-3-chlor-propyl-(β-hydroxy-ethyl)-ether 
• 141987-54-4 1-Phenyl-3-chlor-propyl-monochloracetat 
• 22165-45-3 1-Phenyl-3-chlor-propyl-butyloxymethylether 
• 22165-42-0 1-Phenyl-3-chlor-propyl-ethoxymethylether 
• 22165-04-4 1-Phenyl-3-chlor-propyl-n-butylether 
• 100306-34-1 3-chloro-1-phenylpropanol 
• 29938-41-8 2-phenylthietane 
• 22912-90-9 (RS)-3-chloro-1-phenyl-1-propyl acetate 
• 293322-40-4 3-Cloro-1-phenylpropyl butanoate 

Relevant articles and documents

Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds

Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation reaction, also known as the Matteson reaction, involves formal carbenoid insertions into C-B bonds. Here we report the development of aza-Matteson reactions via carbenoid insertions into the N-B bonds of aminoboranes. By changing the leaving groups of the carbenoids and altering Lewis acid activators, selective mono- and double-methylene insertions can be realized to access various α- and β-boron-substituted tertiary amines, respectively, from common secondary amines. The derivatization of complex amine-containing bioactive molecules, diverse functionalization of the boronate products, and sequential insertions of different carbenoids have also been achieved.

Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients

Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients, are provided. Certain of the systems and methods described herein are capable of manufacturing multiple chemical products without the need to fluidically connect or disconnect unit operations when switching from one making chemical product to making another chemical product.

Naphthyl-derived orthometalated RUII-NHC complexes: Effect of the NHC donors and/or substitution pattern on their synthesis and catalytic activity

Naphthyl-derived orthometalated RuII-NHC complexes have been developed for catalytic applications considering the stereoelectronic profiles of the NHC ligands, which can be modified easily via alteration of the NHC donors (ImNHC/1,2,4tzNHC) as well as their substitution pattern at the naphthyl ring. The azolium salts [(2a?c)-H]Br, precursors for the NHC ligands, react with [Ru(p-cymene)Cl2]2 in the presence of a base to deliver the ortho-metalated RuII-NHC complexes 3a?c with the general formula [(NHC)Ru(p-cymene)Br]. Orthometalation in these complexes can be exploited for further functionalization of the NHC ligands. This is depicted by the generation of the diphenylethylene-inserted isolable intermediate complex 4, from the reaction of 3a with diphenylacetylene in a 1:1 ratio, which eventually provides an annulated salt 5a-Br via reductive elimination. Gratifyingly, this process can also be made catalytic, which directly provides several mono-/bis-annulated cationic N-heterocyclic compounds starting from the imidazolium salts [(2a,b)-H]Br using [Ru(p-cymene)Cl2]2 as a precatalyst. Furthermore, subtle variations in the electronic profiles of the complexes 3a?c in combination with steric alterations are observed to influence their activity in the transfer hydrogenation of acetophenone, a model for the hydride transfer process. Among all the complexes studied here, complex 3b with an ImNHC donor at the second position of the naphthyl ring was identified as a superior catalyst in comparison to 3a,c featuring either a different NHC donor or substitution pattern with a low loading of 0.1 mol%.

Heteroditopic Ru(II)-And Ir(III)-NHC Complexes with Pendant 1,2,3-Triazole/Triazolylidene Groups: Stereoelectronic Impact on Transfer Hydrogenation of Unsaturated Compounds

Imidazol-2-ylidene (ImNHC) and 1,2,3-Traizol-5-ylidene (tzNHC) have been established as important classes of carbene ligands in homogeneous catalysis. To develop Ru(II)/Ir(III) complexes based on these ligand systems considering their electronic as well as steric profiles for hydride transfer reactions, we employed chelating ligands featuring combinations of ImNHC and triazole-N or mesoionic tzNHC donors bridged by a CH2 spacer with possible modifications at triazole backbone. In general, synthesized Ru(II) complexes were found to perform significantly better than analogous Ir(III) complexes in ketone and aldimine reduction. Among the Ru(II) complexes, electron-rich complexes 8/9 of the general formula [(p-cymene)(ImNHC-CH2-TzNHC)RuII(Cl)]BF4 with two different carbene donors (ImNHC and tzNHC) were found to perform appreciably better in ketone reduction than analogous complexes with a combination of ImNHC and triazole-N-donor ([(p-cymene)(ImNHC-CH2-Tz-N)RuII(Cl)]BF4; 4) explaining the electronic fine-Tuning of the catalytic systems. No appreciable variation in activity was observed between complexes 8 and 9 having almost similar electronic profiles. However, less bulky Ru(II) complex 9 with a triazole N-phenyl substituent is more suitable for aldimine reduction than is complex 8, having a triazole N-3,5-dimethylphenyl substituent that explains the steric influence in addition to electronic effect on the reduction process.

Synthesis of Benzylic Alcohols by C-H Oxidation

Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.

3'-chlorobenzene propanol synthesis process

The invention relates to a 3'-chlorobenzene propanol synthesis process, which comprises the following concrete steps that 3'-chloropropiophenone and levo prolinol are sequentially added into 95-percent ethanol; after reaction liquid is completely dissolved, cooling is performed; potassium borohydride is added into reaction liquid in batches; heat insulation is performed after the addition is completed; after reaction liquid is subjected to heating and backflow reaction, the reaction liquid is subjected to pressure reduction concentration; n-hexane is added into the reaction liquid; heating isperformed; then, active carbon is added for heat insulation decoloration; reaction liquid is filtered; filter cake is eluted by the n-hexane; filter liquid is collected; the filter liquid is subjectedto crystallization and filtering; the filter cake is eluted by the n-hexane once; vacuum drying is performed to obtain the 3'-chlorobenzene. The final product of dextro 3'-chlorobenzene propanol is synthesized by using 3'-chloropropiophenone as a major raw material, using potassium borohydride as a reduction agent and using the levo prolinol as a catalyst. The produced 3'-chlorbenzene propanol isa dextro product; the crystallization temperature is higher than that of a mixed spinning product; the synthesis can be realized without needing a specific temperature reduction device; the energy consumption is reduced; the cost is reduced.

Azetidine-Borane Complexes: Synthesis, Reactivity, and Stereoselective Functionalization

The present study reports, for the first time, the synthesis and structural features of azetidine-borane complexes, as well as their reactivity in lithiation reactions. A temperature-dependent stereoselectivity has been disclosed in the reaction of borane with N-alkyl-2-arylazetidines, allowing for a stereoselective preparation of azetidine-borane complexes 2 and 3. A regioselective hydrogen/lithium permutation, at the benzylic position, was observed in lithiation reactions of complexes possessing a syn relationship, between the ring proton and the BH3 group. In contrast, scarce or no reactivity was noticed in complexes lacking such a stereochemical requirement. The configurational stability of the lithiated intermediates has also been investigated, in order to shed some light on the stereoselectivity of the lithiation/electrophile trapping sequence. Calculations helped in supporting experimental observations, concerning structure and reactivity of these azetidine-borane complexes. Data suggest that the BH3 group could promote the lithiation reaction likely by an electrostatic complex induced proximity effect. Interestingly, a new synthetic strategy for the synthesis of N-alkyl-2,2-disubstituted azetidines has been developed.

A Novel Phenylchromane Derivative Increases the Rate of Glucose Uptake in L6 Myotubes and Augments Insulin Secretion from Pancreatic Beta-Cells by Activating AMPK

Purpose: A series of novel polycyclic aromatic compounds that augment the rate of glucose uptake in L6 myotubes and increase glucose-stimulated insulin secretion from beta-cells were synthesized. Designing these molecules, we have aimed at the two main pathogenic mechanisms of T2D, deficient insulin secretion and diminished glucose clearance. The ultimate purpose of this work was to create a novel antidiabetic drug candidate with bi-functional mode of action. Methods: All presented compounds were synthesized, and characterized in house. INS-1E cells and L6 myoblasts were used for the experiments. The rate of glucose uptake, mechanism of action, level of insulin secretion and the druggability of the lead compound were studied. Results: The lead compound (6-(1,3-dithiepan-2-yl)-2-phenylchromane), dose- and time-dependently at the low μM range increased the rate of glucose uptake in L6 myotubes and insulin secretion in INS-1E cells. The compound exerted its effects through the activation of the LKB1 (Liver Kinase B1)-AMPK pathway. In vitro metabolic parameters of this lead compound exhibited good druggability. Conclusions: We anticipate that bi-functionality (increased rate of glucose uptake and augmented insulin secretion) will allow the lead compound to be a starting point for the development of a novel class of antidiabetic drugs.

Effect of functional groups in organic chlorides on radical reduction with hydrostannane under microwave irradiation

The effect of functional groups on the activation of molecules by microwave irradiation in the reduction of organic chlorides by Bu3SnH was investigated. The reactivity of a substrate with a hydroxy group increased under microwave heating conditions in comparison with conventional heating.

A hydrochloric acid west reaches anchors the sandbank preparation method (by machine translation)

The invention discloses a method for preparing west reaches anchors the sandbank hydrochloride, including 3 - chlorobenzene propanol, 1 - phenyl - 3 - (1 - naphthoxy) - 1 - propanol, preparation of pure west reaches anchors the sandbank, west reaches anchors the sandbank DTTA salt preparation, preparation of west reaches anchors the sandbank, hydrochloric acid west reaches anchors the sandbank crude preparation and hydrochloric acid west reaches anchors the sandbank preparation of the finished product, the invention, accelerate the speed of production, the saving in material. (by machine translation)