20261-68-1

Basic information

• Product Name: 1-chlorohexan-2-one
• Synonyms: 1-chlorohexan-2-one;1-Chloro-2-hexanone
• CAS NO: 20261-68-1
• Molecular Formula: C₆H₁₁ClO
• Molecular Weight: 134.61
• Mol File: 20261-68-1.mol

Chemical Properties

• Boiling Point: 173.2 °C at 760 mmHg
• Flash Point: 77 °C
• Appearance: /
• Density: 0.989 g/cm³
• Vapor Pressure: 1.28mmHg at 25°C
• Refractive Index: 1.424
• CAS DataBase Reference: 1-chlorohexan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chlorohexan-2-one(20261-68-1)
• EPA Substance Registry System: 1-chlorohexan-2-one(20261-68-1)

Safety Data

• Hazardous Substances Data: 20261-68-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Chlorohexan-2-one is used as a solvent and intermediate in the production of various chemical compounds. Its unique chemical properties, including the presence of the chlorine atom, make it a valuable component in the synthesis of a wide range of products.
Used in Pharmaceutical Synthesis:
1-Chlorohexan-2-one is utilized in the synthesis of pharmaceuticals due to its reactivity and ability to form specific chemical bonds. Its properties allow it to be incorporated into the structure of various drugs, contributing to their therapeutic effects.
Used in Organic Chemistry Reactions:
As a reagent in organic chemistry, 1-chlorohexan-2-one is employed in various reactions to facilitate the formation of desired products. Its versatility in participating in different types of reactions makes it a useful tool for chemists in research and development.
Used in Industrial Applications:
1-Chlorohexan-2-one is used in various industrial applications, including the production of paints, coatings, and adhesives. Its solvent properties and ability to dissolve a wide range of substances make it a valuable component in these industries.
However, it is important to handle and use 1-chlorohexan-2-one with caution, as it is toxic and may cause irritation upon contact with the skin and eyes. Proper safety measures should be taken to minimize potential health risks associated with its use.

InChI:InChI=1/C6H11ClO/c1-2-3-4-6(8)5-7/h2-5H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 638-29-9 n-valeryl chloride 
• 73397-68-9 1-hydroxyhexan-2-one 
• 124-63-0 methanesulfonyl chloride 
• 109-65-9 1-bromo-butane 
• 79-04-9 chloroacetyl chloride 
• 67442-07-3 2-chloro-N-methoxy-N-methylacetamide 
• 693-04-9 butyl magnesium bromide 
• 64661-42-3 ethyl 2-chloro-3-oxoheptanoate 
• 7737-62-4 Ethyl 3-oxoheptanoate 
• 539-82-2 ethyl n-valerate 
• 3926-62-3 sodium monochloroacetic acid 
• 109-52-4 valeric acid 

Downstream Products

• 80387-18-4 2-oxohexyl benzoate 
• 261963-25-1 (-)-(R)-(phenyl)(phenylmethoxycarboxylamino)acetic acid 2-oxo-hexyl ester 
• 33501-82-5 1-ethylsulfanyl-hexan-2-one-(2,4-dinitro-phenylhydrazone) 
• 113093-50-8 1-benzenesulfonylhexan-2-one 
• 66716-59-4 1-(Phenylthio)hexan-2-one 
• 882499-96-9 1-[4-(Piperidine-1-sulfonyl)-phenylsulfanyl]-hexan-2-one 
• 280775-53-3 1-(2-Oxo-hexyl)-2-(1-(((Phenylmethoxy)carbonyl)-amino)-methyl)-4-(2-methoxy phenyl)-imidazole 
• 138568-81-7 2-[4-(4-Butyl-thiazol-2-yl)-3-chloro-phenyl]-propionic acid 
• 138568-73-7 2-[4-(4-Butyl-thiazol-2-yl)-3-fluoro-phenyl]-propionic acid 
• 132483-55-7 2-[4-(4-Butyl-thiazol-2-yl)-phenyl]-propionic acid 
• 141582-76-5 Benzoic acid (S)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexyl ester 
• 141582-76-5 Benzoic acid (R)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexyl ester 
• 93339-60-7 toluene-4-sulfonic acid (2-hydroxyhexyl) ester 
• 23246-47-1 (+/-)-2-hydroxyhexyl benzoate 

Relevant articles and documents

Prostaglandins and Congeners. 27. Synthesis of Biologically Active 16-Halomethyl Derivatives of 15-Deoxy-16-hydroxyprostaglandin E2

The 16-CF3, -CHF2, -CH2F, and -CH2Cl derivatives of DL-15-deoxy-16-hydroxyprostaglandin E2 (8a, 8b, 8c, and 8d, respectively) were prepared by conjugate addition of the lithiocuprates derived from the appropriately functionalized vinylstannanes 4 to cyclopentenone 6.Hydrolysis of the rather stable O-Si linkage at C-16 of the prostaglandin is discussed.The 13C-NMR chemical shifts of the prostaglandin analogues and intermediates are noted.

Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent "ene"-Reductases

α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent ‘ene'-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.

Design and synthesis of potent and selective inhibitors of BRD7 and BRD9 bromodomains

Emerging evidence suggests bromodomain-containing proteins 7 and 9 (BRD7 and BRD9) have roles in the regulation of human transcription and disease including cancer. We describe potent and selective inhibitors of the BRD7 and BRD9 bromodomains intended for use as tools to elucidate the biological roles of BRD7 and BRD9 in healthy and diseased cells.

Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

Bisaryl-sulfonamides

Compounds, compositions and methods are provided that are useful in the treatment or prevention of a condition or disorder mediated by PPARγ or PPARδ. In particular, the compounds of the invention modulate the function of PPARγ or PPARδ. The subject methods are particularly useful in the treatment and/or prevention of diabetes, obesity, hypercholesterolemia, rheumatoid arthritis and atherosclerosis.

Endothelin antagonists

A compound of the formula (I): or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.

A general synthesis of enantiopure 1,2-aminoalcohols via chiral morpholinones

Eleven optically active 1,2-aminoalcohols 20a-i and 26b-c were prepared from D-phenylglycine via cyclic imines 7b-i (or enamine 7a). The key step of the strategy is the diastereoselective reduction of chiral oxazinones 7a-i.

ENDOTHELIN ANTAGONISTS

A compound of the formula (I): STR1 or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.

ENDOTHELIN ANTAGONISTS

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The chemoselective cyclisation of unsymmetrical γ-diketones to cyclopentenones by ditected aldol reaction using a magnesium chelate

The feasibility of synthesising disubstituted cyclopent-2-enones chemoselectively from unsymmetrical γ-diketones, using an aldol reaction directed by magnesium chelation, has been studied.Treatment of 3,3-dimethylhexane-2,5-dione 15 with aqueous sodium hydroxide (0.5 mol dm-3) gives a mixture of 3,5,5-trimethyl- 12 and 3,4,4-trimethylcyclopent-2-enone 14 in an isomer ratio 2.2:1.Insertion of an α-methoxycarbonyl grouping as a control element allows formation of a magnesium chelate 17 when treated with magnesium methoxide, and the major product is then mainly the undehydrated aldol 21.This, when treated with aqueous sodium hydroxide (0.5 mol dm-3) to dehydrate, hydrolyse and decarboxylate, gives the 3,5,5-trimethyl- and 3,4,4-trimethylcyclopent-2-enones in a nearly chemospecific ratio of 1:49.When 3-methoxycarbonyl-4,4-dimethylhexane-2,5-dione 16 is treated with aqueous sodium hydroxide (0.5 mol dm-3), omitting the magnesium methoxide treatment, the corresponding ratio of cyclopentenones was still an interesting 1:7.3.Treatment with sodium methoxide in methanol gives, by contrast γ-lactone 27.Treatment of undecane-4,7-dione 34 with aqueous sodium hydroxide (0.5 mol dm-3) at reflux gives 2,3-dipropylcyclopent-2-enone 36 and 3-butyl-2-ethylcyclopent-2-enones 35 in a ratio of almost 1:1.Treatment of 6-methoxycarbonylundecane-4,7-dione 33 with magnesium methoxide in methanol gives undehydrated aldol which when treated with aqueous sodium hydroxide gives the dipropylcyclopent-2-enone 36 and 3-butyl-2-ethylcyclopent-2-enones 35 in 9:1 ratio.Conversely, the 5-methoxycarbonyldione 32 gives a corresponding ratio of 36 to 35 of 1:9.The best ratios attained, 1:15 for 36 and 35 from 32 and 20:1 for 36 and 35 from 33, were when magnesium methoxide in refluxing benzene or toluene were employed.There is still a strong chemoselective effect when the magnesium treatment is omitted.Preliminary examination of the corresponding cyclohex-2-enone systems gave poorer chemoselectivities when either procedure was employed. 6-Methoxycarbonyldodecane-5,9-dione 52 gave 2,3-dipropyl-54 and 3-butyl-2-ethyl-cyclohex-2-enone 55 in a ratio of ca. 4:1 whilst the 5-methoxycarbonyldodecane-4,8-dione 53 gave a 1: ca. 4 ratio.