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Revision as of 11:36, 20 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit Latest revision as of 11:54, 29 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Nitrobenzene derivatives; added Category:2-Nitrophenyl compounds using HotCat 
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{{orphan|date=January 2010}}

{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 399298393 | verifiedrevid = 477214896
| Reference=<ref>http://www.21cnlab.com/chemdict/MSDS/62967.html 2-Nitrocinnamaldehyde MSDS</ref> | Reference =<ref>http://www.21cnlab.com/chemdict/MSDS/62967.html 2-Nitrocinnamaldehyde MSDS</ref>
| ImageFile = 2-nitrocinnamaldehyde.svg | ImageFile = 2-nitrocinnamaldehyde.svg
| ImageSize = 160px | ImageSize = 160px
| IUPACName = (''E'')-3-(2-Nitrophenyl)prop-2-enal | PIN = (2''E'')-3-(2-Nitrophenyl)prop-2-enal
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChEMBL = 53723 | CASNo = 1466-88-2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 66894-06-2
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (''E'')
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 72Y4RH8QTA
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 53723
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 4518729
| EC_number = 215-988-0
| PubChem = 5367122 | PubChem = 5367122
| InChI = 1/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+ | InChI = 1/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+ | StdInChI = 1S/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VMSMELHEXDVEDE-HWKANZROSA-N | StdInChIKey = VMSMELHEXDVEDE-HWKANZROSA-N
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 4518729
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>9</sub>H<sub>7</sub>O<sub>3</sub>N | Formula = C<sub>9</sub>H<sub>7</sub>O<sub>3</sub>N
| Appearance = Pale yellow crystalline powder | Appearance = Pale yellow crystalline powder
| Density = | Density =
| MeltingPt = 124-126 °C | MeltingPtC = 124 to 126
| MeltingPt_notes =
| BoilingPt =
| Solubility = Slightly soluble | BoilingPt =
| Solubility = Slightly soluble
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
| RPhrases =
| SPhrases = {{S24}} {{S25}}
⚫ | NFPA-H =
⚫ | NFPA-F =
⚫ | NFPA-R =
⚫ | NFPA-O =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
⚫ | NFPA-H =
⚫ | NFPA-F =
⚫ | NFPA-R =
⚫ | NFPA-S =
⚫ }}
}} }}


'''2-Nitrocinnamaldehyde''', '''''ortho''-nitrocinnamaldehyde''' or '''''o''-nitrocinnamaldehyde''' is an organic ] compound containing a ] ] ortho- to the 1-position of ]. '''2-Nitrocinnamaldehyde''', '''''ortho''-nitrocinnamaldehyde''' or '''''o''-nitrocinnamaldehyde''' is an organic ] compound containing a ] ] ortho- to the 1-position of ].


==Synthesis== ==Synthesis==


2-Nitrocinnamaldehyde can be synthesized by dissolving cinnamaldehyde to a solution of ] in ], and adding a stoichiometric amount of concentrated ] at 0-5 °C. Yields are around 36-46% of theoretical. 2-Nitrocinnamaldehyde can be synthesized by dissolving cinnamaldehyde to a solution of ] in ], and adding a stoichiometric amount of concentrated ] at 0–5&nbsp;°C. Yields are around 36-46% of theoretical.


] of cinnamaldehyde via acidification of a ] salt with ] also yields the ortho-nitro compound, however it also yields some of the para-nitro compound, which is generally undesired. ] of cinnamaldehyde via acidification of a ] salt with ] also yields the ortho-nitro compound, however it also yields some of the para-nitro compound, which is generally undesired.


2-Nitrocinnamaldehyde can also be prepared by reacting ] with ] in a condensation reaction.<ref>http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=181&prep=CV4P0722</ref> 2-Nitrocinnamaldehyde can also be prepared by reacting ] with ] in a condensation reaction.<ref>{{cite web | url=http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=181&prep=CV4P0722 | title=Organic Syntheses }}</ref>


==Uses== ==Uses==
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{{DEFAULTSORT:Nitrocinnamaldehyde, 2-}} {{DEFAULTSORT:Nitrocinnamaldehyde, 2-}}
] ]
] ]