4224-70-8

Basic information

• Product Name: 6-Bromohexanoic acid
• Synonyms: ω-BroMohexanoic Αcid;6 - broMine caproic acid;6-bromo-hexanoicaci;6-Bromo-n-caproic acid;6-BROMO-N-HEXANOIC ACID;6-BROMOCAPROIC ACID;6-BROMOHEXANOIC ACID;AKOS BB/0098
• CAS NO: 4224-70-8
• Molecular Formula: C₆H₁₁BrO₂
• Molecular Weight: 195.05
• EINECS: 224-176-5
• Product Categories: C6;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Organic acids;Acids & Esters;Bromine Compounds;omega-Bromocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Aliphatics;Miscellaneous Reagents;Building Blocks
• Mol File: 4224-70-8.mol

Chemical Properties

• Melting Point: 32-34 °C(lit.)
• Boiling Point: 165-170 °C20 mm Hg(lit.)
• Flash Point: 154 °F
• Appearance: White to light orange/Low Melting Crystals
• Density: 1.3996 (rough estimate)
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: 0.1 g/mL, clear, colorless
• PKA: 4.72±0.10(Predicted)
• BRN: 1749740
• CAS DataBase Reference: 6-Bromohexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromohexanoic acid(4224-70-8)
• EPA Substance Registry System: 6-Bromohexanoic acid(4224-70-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-28A
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 8
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4224-70-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-Bromohexanoic acid is used as an intermediate in organic synthesis for the preparation of various compounds, including N-acylsulfonamides, diarylthioethers, and 2-lithio-1,3-dithian. It plays a crucial role in the synthesis of these compounds due to its unique chemical properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Bromohexanoic acid is used as a starting material for the synthesis of N-acylsulfonamides, which are important in the treatment of various medical conditions. The acid is also used in the preparation of alkyl ketones from alkyl iodides and metallic strontium, which can be further utilized in the development of pharmaceutical compounds.
Used in Chemical Research:
6-Bromohexanoic acid is employed in chemical research for the synthesis of anionic mitomycin C-dextran conjugate (MMC-D), which is a potential candidate for targeted drug delivery systems. Its unique chemical properties make it a valuable compound for exploring new synthetic pathways and developing novel applications in the chemical and pharmaceutical industries.

Organic Intermediate

6-bromohexanoic acid, also called 6-bromohexanoic acid or 6-bromo-hexanoic acid, is an organobromine compound comprising hexanoic acid having a bromo substituent at the 6-position. 6-Bromohexanoic acid is used in the preparation of N-acylsulfonamides, diarylthioethers and 2-lithio-1,3-dithian. It is widely used as an intermediate in organic synthesis. Here, we introduced a method for making this compound.

InChI:InChI=1/C6H11BrO2/c7-5-3-1-2-4-6(8)9/h1-5H2,(H,8,9)/p-1

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 143-33-9 sodium cyanide 
• 1191-25-9 6-Hydroxyhexanoic acid 
• 4286-55-9 1-bromo-6-hexanol 
• 34957-71-6 6-acetoxy-hexanenitrile 
• 642470-70-0 N-(5-cyano-pentyl)-benzamide 
• 82258-18-2 (4-phenoxy-butyl)-malonic acid diethyl ester 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 105-60-2 caprolactam 
• 6621-59-6 6-bromo-1-hexanenitrile 
• 14273-90-6 methyl 6-bromohexanoate 
• 108-94-1 cyclohexanone 
• 629-11-8 1,6-hexanediol 
• 2408-01-7 1-hydroperoxycyclohexanol 

Downstream Products

• 25542-62-5 6-bromo-hexanoic acid ethyl ester 
• 407-48-7 6-bromo-hexanoic acid-(2-fluoro-ethyl ester) 
• 5602-19-7 6-cyanohexanaoic acid 
• 6621-59-6 6-bromo-1-hexanenitrile 
• 17689-17-7 6-mercaptocaproic acid 
• 4101-68-2 1,10-dibromodecane 
• 60-32-2 6-aminohexanoic acid 
• 14273-90-6 methyl 6-bromohexanoate 
• 629-57-2 palmitolic acid 
• 26306-00-3 (6-bromohexyl)-trimethylsilyl ether 
• 26306-01-4 6-iodo-1-(trimethylsilyloxy)hexane 
• 34176-76-6 6-Bromhexansaeure-trimethylsilylester 
• 26305-95-3 6-Iodhexansaeure-trimethylsilylester 
• 26825-90-1 14-bromotetradecanoic acid methyl ester 

Relevant articles and documents

Method for preparing 6-bromotriphenylphosphonio-n-caproic acid

The invention relates to the field of production and preparation of compounds and particularly relates to a method for preparing 6-bromotriphenylphosphonio-n-caproic acid. The method comprises the following steps: (1) subjecting caprolactam to a hydrolysis reaction, so as to prepare 6-aminocaproic acid; (2) subjecting 6-aminocaproic acid to a diazotization reaction, so as to prepare 6-hydroxycaproic acid; (3) subjecting 6-hydroxycaproic acid to a bromization reaction, so as to prepare 6-bromocaproic acid; and (4) enabling 6-bromocaproic acid to react with triphenyl phosphine, thereby obtaining 6-bromotriphenylphosphonio-n-caproic acid.

Synthesis of polysiloxane-based quaternized imidazolium salts with a hydroxy group at the end of alkyl groups

A series of polysiloxane derivatives having quaternized imidazolium moieties with hydroxyalkyl groups ([HPImnOH]Xs) (where n is the number of methylene group and X is counter anion) were prepared by quaternization of poly(3-chloropropylmethylsiloxane) (P1) using 1-(ω-hydroxyalkyl)imidazole derivatives (ImnOHs) and anion-exchange reaction using lithium bis(trifluoromethanesulfonyl)imide. Polysiloxane-based quaternized imidazolium salts having hydroxyalkyl groups with chloride anion ([HPImnOH]Cls) were obtained with high quaternization ratio of approximately 100 mol%. The glass transition temperatures (Tgs) of [HPImnOH]Xs were reduced by introducing a hydroxy group at the end of alkyl groups; however, no significant reduction in Tgs was observed by anion exchange from chloride anion to bis(trifluoromethanesulfonyl)imide one (Tf2N-).

DMF-mediated deprotection of bulky silyl esters under neutral and fluoride-free conditions

Bulky TBDPS and TIPS carboxylic esters were efficiently cleaved by a green and mild protocol using only DMF-H2O (20:1) at 70 °C. The neutral conditions tolerate various common acid- and base-labile functionalities, including alkyl and aryl silyl ethers.

Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl- 4(1H)-quinolones

A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships.

A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky

A new phenylethyl alkyl amide, (10R)-10-hydroxy-N-phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic chain was accomplished by the selective protection of the hydroxy groups and two-time implementation of the Wittig olefination reaction.

Fluoroalkene modification of mercaptoacetamide-based histone deacetylase inhibitors

Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. The mercaptoacetoamide-based inhibitors are reported to be less toxic than hydroxamate and are worthy of further consideration. Therefore, we have designed a series of analogs as potential inhibitors of HDACs, in which the mercaptoacetamide group was replaced by (mercaptomethyl)fluoroalkene, and their HDAC inhibitory activity was evaluated. Subnanomolar inhibition was observed for all synthetic compounds.

Hypervalent λ3-bromane strategy for Baeyer-Villiger oxidation: Selective transformation of primary aliphatic and aromatic aldehydes to formates, which is missing in the classical Baeyer-Villiger oxidation

A conceptually distinct, modern strategy for Baeyer-Villiger oxidation (BVO) was developed. Our novel method involves initial hydration of water to carbonyl compounds, followed by ligand exchange of hypervalent aryl-λ3-bromane on bromane(III) with the resulting hydrate, yielding a new type of activated Criegee intermediate. The intermediate undergoes BV rearrangement and produces an ester via facile reductive elimination of an aryl-λ3-bromanyl group, because of the hypernucleofugality. The novel strategy makes it possible to induce selectively the BV rearrangement of straight chain primary aliphatic as well as aromatic aldehydes, which is missing in the classical BVO: for instance, octanal and benzaldehyde afforded rearranged formate esters with high selectivity (>95%) under our conditions, while the attempted classical BVO produced only carboxylic acids. This firmly establishes the powerful nature of new methodology for BVO.

A new one-pot synthetic method for selenium-containing medium-sized α,β-unsaturated cyclic ketones

The reaction of tetrahydroselenopyran-2-one (7) with ethynyllithiums 20a-h, followed by treatment with aqueous 5% H2SO4 successfully led to a two-carbon ring expansion to give the 2-substituted 5,6,7,8-tetrahydroselenocin-4-ones 21a-h in 43-95% yields. Seven- to nine-membered γ-selena-α,β-unsaturated cyclic ketones 22-26 and a 5,6,7,8-tetrahydrotellurocin-4-one 27 were also prepared from the corresponding selenolactones or tellurolactone in a one-pot reaction.

METHODS AND MATERIALS FOR PREPARING ORGANIC COMPOUNDS FROM PRIMARY AMINES

Methods are disclosed for the conversion of primary amines to other functional groups. The methods can be used to prepare chiral organic compounds, including organic alcohols and organic halides. The methods can be carried out by treating a primary amine with an activating agent and a nitrosyl agent to produce the transformed compound along with nitrous oxide.

Synthesis and transdermal permeation-enhancing activity of ketone, amide, and alkane analogs of Transkarbam 12

Transkarbam 12 (5-(dodecyloxycarbonyl)pentylammonium-5-(dodecyloxycarbonyl) pentylcarbamate, T12) is a highly active transdermal permeation enhancer. In this study, ketone, amide, and alkane analogs of T12 have been synthesized and evaluated for their permeation-enhancing activity using porcine skin and theophylline as a model drug. Replacement of ester by methylene and ketone, respectively, led to a significant decrease of activity. Amide analogs displayed lower activity in 60% propylene glycol and were comparable to T12 in isopropyl myristate. An intramolecular H-bond between ester and ammonium-carbamate group was suggested to be important for the permeation-enhancing activity of T12.