14065-32-8

Basic information

• Product Name: METHYL 10-CHLORO-10-OXODECANOATE
• Synonyms: 9-Chloroformylnonanoic acid methyl ester;Methyl 10-chloro-10-oxodecanoate,98%;Methyl 10-chloro-10-oxodecanoate 97%;SEBACINIC ACID MONOMETHYL ESTER MONOCHLORIDE;MONOMETHYLSEBACOYLCHLORIDE;METHYL SEBACOYL CHLORIDE;METHYL 10-CHLORO-10-OXODECANOATE;10-Oxo-10-chlorodecanoic acid methyl ester
• CAS NO: 14065-32-8
• Molecular Formula: C₁₁H₁₉ClO₃
• Molecular Weight: 234.72
• Mol File: 14065-32-8.mol

Chemical Properties

• Melting Point: 16.5-17 °C
• Boiling Point: 159-160 °C9 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: /
• Density: 1.052 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00266mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• CAS DataBase Reference: METHYL 10-CHLORO-10-OXODECANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 10-CHLORO-10-OXODECANOATE(14065-32-8)
• EPA Substance Registry System: METHYL 10-CHLORO-10-OXODECANOATE(14065-32-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 16-23-26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14065-32-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
METHYL 10-CHLORO-10-OXODECANOATE is used as a synthetic intermediate for the preparation of various compounds, including:
1. Methyl 10-[2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]-10-oxodecanoate: METHYL 10-CHLORO-10-OXODECANOATE is synthesized using METHYL 10-CHLORO-10-OXODECANOATE as a key intermediate, showcasing its importance in the development of novel chemical entities.
2. Fluorescein-derivatives of Necrostatin-3: METHYL 10-CHLORO-10-OXODECANOATE plays a crucial role in the synthesis of these derivatives, which have potential applications in biological and medical research.
3. Methyl 10-oxo-10-(Pyren-3-yl)decanoate: METHYL 10-CHLORO-10-OXODECANOATE is synthesized using METHYL 10-CHLORO-10-OXODECANOATE, highlighting its versatility in chemical synthesis and its ability to contribute to the creation of diverse chemical structures.

InChI:InChI=1/C11H19ClO3/c1-15-11(14)9-7-5-3-2-4-6-8-10(12)13/h2-9H2,1H3

Upstream product

• 67-56-1 methanol 
• 111-19-3 sebacoyl chloride 
• 818-88-2 sebacic acid mono methyl ester 
• 111-20-6 1,10-decanedioic acid 
• 106-79-6 dimethyl sebacate 

Downstream Products

• 14811-73-5 10-oxo-decanoic acid methyl ester 
• 16727-05-2 10-oxo-10-phenyl-decanoic acid methyl ester 
• 818-88-2 sebacic acid mono methyl ester 
• 106-79-6 dimethyl sebacate 
• 692-88-6 Decandisaeureethylmethylester 
• 95799-78-3 10-Keto-12-methyltridecansaeuremethylester 
• 676-00-6 10-oxo-undecanoic acid 
• 374622-17-0 methyl 10-(2,3,4,5-tetramethoxy-6-methylphenyl)-10-undecenoate 
• 58186-27-9 Idebenone 
• 58186-28-0 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone 
• 374622-25-0 1-(2,3,4,5-tetramethoxy-6-methylphenyl)-1,10-decenediol 
• 374622-20-5 10-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate 
• 374622-18-1 10-methylcarbonyloxy-1-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate 
• 64701-47-9 10-(1-pyrenyl)decanoic acid 

Relevant articles and documents

Tumor-targeting with novel non-benzoyl 6-substituted straight chain pyrrolo[2,3-d ]pyrimidine antifolates via cellular uptake by folate receptor α and inhibition of de novo purine nucleotide biosynthesis

A new series of 6-substituted straight side chain pyrrolo[2,3-d]pyrimidines 3a-d with varying chain lengths (n = 5-8) was designed and synthesized as part of our program to provide targeted antitumor agents with folate receptor (FR) cellular uptake specificity and glycinamide ribonucleotide formyltransferase (GARFTase) inhibition. Carboxylic acids 4a-d were converted to the acid chlorides and reacted with diazomethane, followed by 48% HBr to generate the α-bromomethylketones 5a-d. Condensation of 2,4-diamino-6-hydroxypyrimidine 6 with 5a-d afforded the 6-substituted pyrrolo[2,3-d]pyrimidines 7a-d. Hydrolysis and subsequent coupling with diethyl l-glutamate and saponification afforded target compounds 3a-d. Compounds 3b-d showed selective cellular uptake via FRα and -β, associated with high affinity binding and inhibition of de novo purine nucleotide biosynthesis via GARFTase, resulting in potent inhibition against FR-expressing Chinese hamster cells and human KB tumor cells in culture. Our studies establish, for the first time, that a side chain benzoyl group is not essential for tumor-selective drug uptake by FRα.

Effects of structural variations of non-ionic surfactants on micellar properties and solubilization: surfactants containing very long hydrocarbon chains

Polyoxyethylene mono-ethers of dotriacontanol (C32E41) and 4,9-dimethyltritriacontanol (C35E40) have been synthesized. The micellar weights in water at 298K were 4.82 x 105 and 5.90 x 105, the aggregation numbers 212 and 260, and the levels of hydration 290 and 283 mol water mol-1 surfactant, respectively. The solubilization of azobenzene, cortisone acetate, griseofulvin, sulphadiazine, phenylbutazone, betamethasone, tolbutamide, and menaphthone was studied in 2% solutions of the above surfactants. The presence of large micelles did not result in increased solubilization; C32E41 and C35E40 had a lower solubilizing capacity than that of cetomacrogol.

Novel (3,5-di-tert-butyl-2-hydroxy-phenylcarbamoyl)-alkanoic acids as potent antioxidants

A series of novel phenolic antioxidants of amphiphilic structure has been synthesized. Investigations into the influence of aliphatic spacer length and nature of a hydrophilic anchor on the antioxidant activity allowed elucidating certain structure requirements for the membrane-addressed antioxidant designing.

Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine

[Figure not available: see fulltext.] A method for the synthesis of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine containing fragments of ω-amino acids with different lengths of the polymethylene chain as a linker has been developed. It was found in experiments in vitro that the obtained compounds are active against the herpes simplex virus type 1, including the acyclovir-resistant strain.

SYNTHETIC PROCESSES AND INTERMEDIATES

The invention provides synthetic processes and synthetic intermediate compounds that can be used to prepare therapeutic conjugates. The invention also provides methods for treating HBV and/or HDV infection in a human by administering a therapeutic conjugate prepared by the synthetic methods of the invention.

Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction

Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.

Defining a minimum pharmacophore for simocyclinone D8 disruption of DNA gyrase binding to DNA

The increasing occurrence of drug-resistant bacterial infections in the clinic has created a need for new antibacterial agents. Natural products have historically been a rich source of both antibiotics and lead compounds for new antibacterial agents. The natural product simocyclinone D8 (SD8) has been reported to inhibit DNA gyrase, a validated antibacterial drug target, by a unique catalytic inhibition mechanism of action. In this work, we have used a deconstruction-reconstruction approach to prepare analogs of the coumarin subunit of SD8 and evaluated their ability to disrupt binding of the DNA gyrase enzyme to DNA in a surface plasmon resonance assay. This has led to a minimum pharmacophore required for disruption of binding. Springer Science+Business Media 2014.

Palladium-catalyzed reduction of acid chlorides to aldehydes with hydrosilanes

An efficient synthesis of aldehydes from acid chlorides with hydrosilanes as a reducing agent in the presence of a palladium catalyst has been achieved. A simple mixture of commercially available Pd(dba)2 and Mes 3P as a catalyst realized the reduction of various acid chlorides including aliphatic acid chlorides and a, P-unsaturated acid chlorides to the corresponding aldehydes in good to high yields under mild reaction conditions. Georg Thieme Verlag Stuttgart ? New York.

Synthesis of novel phytosphingosine derivatives and their preliminary biological evaluation for enhancing radiation therapy

Eight d-ribo-phytosphingosine derivatives were synthesized from d-ribo-phytosphingosine and diverse acyl chlorides with N,N-diisopropylethylamine in tetrahydrofuran for 1 h at room temperature. Effect of these compounds on IR-induced cell death was evaluated on blood cancer cells (Jurkat). Among these, 3d showed the highest enhancement of radiosensitizing effect.

PROTEIN BINDING COMPOUNDS

The present invention provides a prodrug compound comprising a therapeutically effective moiety coupled via a metabolically cleavable bond to a blood protein binding moiety.