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
• Article Data: 7

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

6-Nitrohexanoic acid may be used in the synthesis of 6-aminohexanoic acid, which on polymerization yields Nylon-6. It may be used in the synthesis of conjugable analog of benzodiazepine 4′′chlorodiazepam (Ro5-4864), C6Ro5-4864.

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

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

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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.

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.