51787-87-2

Basic information

• Product Name: alpha-(3-chloropropyl)-4-fluorobenzyl alcohol
• Synonyms: alpha-(3-chloropropyl)-4-fluorobenzyl alcohol;α-(3-Chloropropyl)-4-fluorobenzenemethanol;Einecs 257-420-4
• CAS NO: 51787-87-2
• Molecular Formula: C₁₀H₁₂ClFO
• Molecular Weight: 202.6530832
• EINECS: 257-420-4
• Mol File: 51787-87-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: alpha-(3-chloropropyl)-4-fluorobenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-(3-chloropropyl)-4-fluorobenzyl alcohol(51787-87-2)
• EPA Substance Registry System: alpha-(3-chloropropyl)-4-fluorobenzyl alcohol(51787-87-2)

Safety Data

• Hazardous Substances Data: 51787-87-2(Hazardous Substances Data)

Upstream product

• 462-06-6 fluorobenzene 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 

Downstream Products

• 160497-52-9 Acetic acid (R)-4-chloro-1-(4-fluoro-phenyl)-butyl ester 
• 68883-08-9 1-(p-Fluorphenyl)-4-(4'-methylpiperidino)-1-butanol 
• 34104-67-1 reduced haloperidol 
• 1520089-73-9 4-(4-chloro-1-(4-fluorophenyl)-1-hydroxybutyl)benzonitrile 
• 1266676-21-4 (+/-)-4-chloro-1-(4-fluorophenyl)butyl 4-phenylbutanoate 
• 98440-36-9 11-[1-[[4-(4-Fluorophenyl)-4-hydroxy]butyl]piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepin 
• 160423-04-1 (+/-)-α-(3-chloropropyl)-4-fluorobenzenemethanol acetate 
• 126640-10-6 (1S)-(-)-4-chloro-1-(4-fluorophenyl)butan-1-ol 
• 126640-11-7 (1R)-(+)-4-chloro-1-(4-fluorophenyl)butan-1-ol 

Relevant articles and documents

Structure-Kinetic Profiling of Haloperidol Analogues at the Human Dopamine D2 Receptor

Haloperidol is a typical antipsychotic drug (APD) associated with an increased risk of extrapyramidal side effects (EPSs) and hyperprolactinemia relative to atypical APDs such as clozapine. Both drugs are dopamine D2 receptor (D2R) antagonists, with contrasting kinetic profiles. Haloperidol displays fast association/slow dissociation at the D2R, whereas clozapine exhibits relatively slow association/fast dissociation. Recently, we have provided evidence that slow dissociation from the D2R predicts hyperprolactinemia, whereas fast association predicts EPS. Unfortunately, clozapine can cause severe side effects independent of its D2R action. Our results suggest an optimal kinetic profile for D2R antagonist APDs that avoids EPS. To begin exploring this hypothesis, we conducted a structure-kinetic relationship study of haloperidol and revealed that subtle structural modifications dramatically change binding kinetic rate constants, affording compounds with a clozapine-like kinetic profile. Thus, optimization of these kinetic parameters may allow development of novel APDs based on the haloperidol scaffold with improved side-effect profiles.

Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells

Complex mechanisms of prostate cancer progression prompt to novel therapeutic strategies concerning a combination of drugs or of single molecules able to interact with more crucial targets. Histone deacetylase inhibitors and sigma ligands with mixed σ1 antagonist and σ2 agonist properties were proposed as new potential tools for treatment of prostate cancer. (±)-MRJF4 was synthesized as phenylbutyrate ester of haloperidol metabolite II, which is a molecule consisting of a histone deacetilase inhibitor (4-phenylbutyric acid) and a sigma ligand (haloperidol metabolite II). Antiproliferatives activities of 4-phenylbutyric acid, haloperidol metabolite II, equimolar mixture of both compounds and (±)-MRJF4 were evaluated in vitro on LNCaP and PC3 prostate cancer cells. Preliminary binding studies of (±)-MRJF4 for σ1, σ2, D2 and D3 receptors and inhibition HDAC activity were reported. MTT cell viability assays highlighted a notable increase of antiproliferative activity of (±)-MRJF4 (IC50 = 11 and 13 μM for LNCaP and PC3, respectively) compared to 4-phenylbutyric acid, haloperidol metabolite II and the respective equimolar pharmacological association. (±)-MRJF4 was also used in combination with σ1 agonist (+)-pentazocine and σ2 antagonist AC927 in order to evaluate the role of σ receptor subtypes in prostate cancer cell death.

Resolution of α-(4-Fluorophenyl)-4-(5-fluoro-2-pyrimidinyl)-1-piperazinebutanol (BMS 181100) and α-(3-Chloropropyl)-4-Fluorobenzenemethanol Using Lipase-Catalyzed Acetylation or Hydrolysis

α-(3-Chloropropyl)-4-fluorobenzenemethanol, a possible intermediate for synthesis of a potential anti-psychotic agent α-(4-fluorophenyl)-4-(5-fluoro-2-pyrimidinyl)-1-piperazine butanol (BMS 181100), was resolved by acetylation using isopropenyl acetate and lipase PS-30 in heptane.S-alcohol was obtained in 42percent yield with >99percent optical purity.R-acetate was obtained with 92.6percent optical purity by stopping the reaction after 46percent conversion.The enzymatically produced acetate was hydrolyzed by lipase PS-30 to give R-alcohol with >99percent optical purity after 62-72percent conversion.BMS 181100 acetate ester was treated with lipase GC-20 in buffer containing 10percent toluene to give the R-alcohol with 97.9percent optical purity after 47.6percent conversion.The rate and enantioselectivity of hydrolysis by lipase GC-20 were very dependent on the organic solvent.E values ranged from 1 in the absence of organic solvent to >100 with dichloromethane and toluene.