10269-96-2

Basic information

• Product Name: 6-NITROCAPROIC ACID
• Synonyms: 6-NITROHEXANOIC ACID;6-NITROCAPROIC ACID
• CAS NO: 10269-96-2
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.16
• Mol File: 10269-96-2.mol

Chemical Properties

• Melting Point: 21-22 °C(lit.)
• Boiling Point: 136 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.186 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.25E-05mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• CAS DataBase Reference: 6-NITROCAPROIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-NITROCAPROIC ACID(10269-96-2)
• EPA Substance Registry System: 6-NITROCAPROIC ACID(10269-96-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 10269-96-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
6-Nitrocaproic acid is used as an intermediate in the synthesis of 6-aminohexanoic acid, which upon polymerization yields Nylon-6. This is a widely used synthetic polymer with various applications in the textile, automotive, and electrical industries.
Used in Pharmaceutical Industry:
6-Nitrocaproic acid is used as a key intermediate in the synthesis of conjugable analogs of benzodiazepines, such as 4′′chlorodiazepam (Ro5-4864) and C6Ro5-4864. These compounds have potential applications in the development of new drugs and therapies for various medical conditions.

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 1995, 1967 DOI: 10.1021/jo01281a067

InChI:InChI=1/C6H11NO4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)

Upstream product

• 4883-67-4 2-nitrocyclohexanone 
• 13395-05-6 6-Nitrocapronsaeureethylester 
• 25542-62-5 6-bromo-hexanoic acid ethyl ester 
• 105-60-2 caprolactam 

Downstream Products

• 124-04-9 Adipic acid 
• 146347-17-3 1-Methylthio-2-nitro-cyclohexen 
• 146347-12-8 2,2-Bis(methylthio)cyclohexanon-oxim 
• 60-32-2 6-aminohexanoic acid 

Relevant articles and documents

Synthesis of ω-nitro acids and ω-amino acids by ring cleavage of α- nitrocycloalkanones

The reaction of various α-nitrocycloalkanones 1 with aqueous 0.05 M NaOH, at 80 °C, in the presence of cetyltrimethylammonium chloride (CTACl) as a cationic surfactant, produces ω-nitro acids 2 in good yields. Reduction of the latter with HCOONH4/Pd-C, in methanol, at 80 °C affords ω-amino acids 3. The synthesis of methyl 9-oxodecanoate (8) is also reported.

Heterolytic (2 e) vs Homolytic (1 e) Oxidation Reactivity: N?H versus C?H Switch in the Oxidation of Lactams by Dioxirans

Dioxiranes are powerful oxidants that can act via two different mechanisms: 1) homolytic (H abstraction and oxygen rebound) and 2) heterolytic (electrophilic oxidation). So far, it has been reported that the nature of the substrate dictates the reaction mode independently from the dioxirane employed. Herein, we report an unprecedented case in which the nature of the dioxirane rules the oxidation chemoselectivity. In particular, a switch from C?H to N?H oxidation is observed in the oxidation of lactams moving from dimethyl dioxirane (DDO) to methyl(trifluoromethyl)dioxirane (TFDO). A physical organic chemistry study, which combines the oxidation with two other dioxiranes methyl(fluoromethyl)dioxirane, MFDO, and methyl(difluoromethyl)dioxirane, DFDO, with computational studies, points to a diverse ability of the dioxiranes to either stabilize the homo or the heterolytic pathway.

Oxidative cleavage of lactams in water using dioxiranes: An expedient and environmentally-safe route to ω-nitro acids

By taking advantage of the appreciable stability of dioxiranes in water, a safe yet efficient route to ω-nitro acids by oxidation of lactams of various ring sizes under mild conditions has been reported. In essentially all the cases examined, reactions proceed selectively to afford products in remarkably high yields (up to 99%) and with high purity (94-99%). Also, an interesting example of higher reaction selectivity in water than in organic solvent (acetonitrile) is discussed.

DARSTELLUNG UND ELEKTROCHEMISCHE REDUKTION NITROSUBSTITUIERTER ALKANDITHIOSAEURE-METHYLESTER

Methyl nitroalkanedithioates 3 were prepared from the corresponding carboxylic acids 1 and Davy's reagent 2 or, 3e, from 2-nitro-propane, carbon disulfide and iodomethane.Electrochemical reduction of these dithioesters leads to ketene S,S-acetals 4 and oximes 5.In addition, carboxylic oximes 6 are formed.The latter and related elimination products 14 are also obtained by conventional routes.Key words: Methyl nitroalkanedithioates; polarography; cyclovoltammetry; preparative electroreduction; intramolecular cyclization.

Enantioselective Saponification of Diacetates of 2-Nitro-1,3-propanediols by Pig-Liver Esterase and Preparation of Enantiomerically Pure Derivatives of 2-Nitro-allylic Alcohols (Chiral Multiple-Coupling Reagents)

The reproducible enantioselective saponification of open-chain and cyclic diacetates of meso-2-nitro-1,3-propanediols (see 4b-13b) with pig-liver esterase (PLE) gives monoacetates (see 4c-13c) of >95percent enantiomeric excess.The Re enantiotopic acetate group appears to be saponified preferentially, as proved by the X-ray crystal structure analysis of three camphanoates 4d, 6d, and 7d.Elimination of H2O or AcOH from the hydroxy acetates thus available gives derivatives of nitro-allylic alcohols (see 20-24, 27, and 29) which are subjected to diastereoselective Michael additions or SN2' substitutions.

RING CLEAVAGE OF CYCLIC 2-NITROKETONES BY KF CATALYST: A GENERAL SYNTHESIS OF ω-NITROACIDS AND ω-NITROESTERS.

Preparation of ω-nitroacids and ω-nitroesters has been achieved by ring cleavage of 2-nitrocycloalkanones, under basic condition (KF), in water (THF solution) or alcohol.

Conjugated diene derivatives

There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugat