123910-86-1

Basic information

• Product Name: Methyl 4-(4-hydroxybut-1-ynyl)benzoate
• Synonyms: Methyl 4-(4-hydroxybut-1-ynyl)benzoate
• CAS NO: 123910-86-1
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.22188
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 123910-86-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 95.3-96.3 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 350.6±27.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• PKA: 14.36±0.10(Predicted)
• CAS DataBase Reference: Methyl 4-(4-hydroxybut-1-ynyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-(4-hydroxybut-1-ynyl)benzoate(123910-86-1)
• EPA Substance Registry System: Methyl 4-(4-hydroxybut-1-ynyl)benzoate(123910-86-1)

Safety Data

• Hazardous Substances Data: 123910-86-1(Hazardous Substances Data)

Usage

Description

Methyl 4-(4-hydroxybut-1-ynyl)benzoate is a light yellow solid that serves as a versatile reactant in organic synthesis. It is characterized by its unique structure, which includes a benzoate group and a hydroxybutynyl chain, making it a valuable intermediate in the synthesis of various compounds.

Uses

Used in Organic Synthesis:
Methyl 4-(4-hydroxybut-1-ynyl)benzoate is used as a reactant in organic synthesis for its ability to undergo various chemical reactions, leading to the formation of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
Methyl 4-(4-hydroxybut-1-ynyl)benzoate is used as a key intermediate in the preparation of mitochondrial complex 1 inhibitors, which have potential as cardiac PET (positron emission tomography) tracers. These tracers are valuable for imaging and diagnosing cardiac conditions, as well as for monitoring the effectiveness of treatments.
Additionally, Methyl 4-(4-hydroxybut-1-ynyl)benzoate is utilized in the synthesis of antifolate drugs, which are important in the treatment of various diseases, including cancer and anemia. Antifolates work by inhibiting the synthesis of essential nucleotides and amino acids, thereby disrupting the growth and replication of cells.

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-44-3 methyl 4-iodobenzoate 
• 927-74-2 3-Butyn-1-ol 
• 1280640-24-5 C₁₄H₁₁NO₄ 

Downstream Products

• 106200-41-3 4-(4-carbomethoxyphenyl)butanal 
• 134373-15-2 4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid 
• 144051-63-8 4-[3-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoic acid 
• 125991-54-0 diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate 
• 229471-26-5 4-(4-hydroxy-5-nitropentyl)benzoic acid methyl ester 
• 259145-26-1 4-[4-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-5-nitropentyl]benzoic acid methyl ester 
• 229471-28-7 4-[5-nitro-4-(2,4,6-triaminopyrimidin-5-yl)pentyl]benzoic acid methyl ester 
• 1280640-24-5 C₁₄H₁₁NO₄ 

Relevant articles and documents

Designing Homogeneous Copper-Free Sonogashira Reaction through a Prism of Pd-Pd Transmetalation

Simultaneous introduction of two different palladium (pre)catalysts, one tuned to promote oxidative addition to (hetero)aryl bromide and another to activate terminal alkyne substrate, leads to productive Pd-Pd transmetalation, subsequent reductive elimina

Synthesis and antiviral study of novel 4-(2-(6-amino-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyrimidin-3-yl)ethyl)benzamide derivatives

A series of ten new compounds (7a–j) has been synthesized by absolutely replacing the glutamic acid part of Pemetrexed drug, chemically known as N-{4-[2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-l-glutamic acid, with primary, secondary, and aryl amines in high yields using diethylphosphorocyanidate (DEPC) as a peptide coupling agent. All the synthesized compounds are characterized by 1H and 13C NMR, LCMS, and FT-IR spectral techniques. All the synthesized novel non-glutamate 4-(2-(6-amino-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyrimidin-3-yl)ethyl)benzamide derivatives showed 4- to 7-folds higher antiviral activity than its structurally similar commercial drug Pemetrexed against Newcastle disease virus, an avian paramyxovirus. Among the lot, compounds possessing carboxamide synthesized using five-membered heteroaryl amines (7i and 7j) exhibited the highest antiviral activity. [Figure not available: see fulltext.].

INHIBITORS OF HISTONE LYSINE SPECIFIC DEMETHYLASE (LSD1) AND HISTONE DEACETYLASES (HDACS)

A series of phenelzine analogs comprising a phenelzine scaffold linked to an aromatic moiety and their use as inhibitors of lysine-specific demethylase 1 (LSD1) and/or one or more histone deacetylases (HDACs) is provided. The presently disclosed phenelzine analogs exhibit potency and selectivity for LSD1 versus MAO and LSD2 enzymes and exhibit bulk, as well as, gene specific histone methylation changes, anti-proliferative activity in several cancer cell lines, and neuroprotection in response to oxidative stress. Accordingly, the presently disclosed phenelzine analogs can be used to treat diseases, conditions, or disorders related to LSD1 and/or HDACs, including, but not limited to, cancers and neurodegenerative diseases.