| Identification | More | [Name]
2-Nitrobenzaldehyde | [CAS]
552-89-6 | [Synonyms]
2-FORMYLNITROBENZENE
2-NITROBENZALDEHYDE
AKOS 93864
AKOS BBS-00003153
NITROBENZALDEHYDE-2
O-NITROBENZALDEHYDE
ORTHONITRO BENZALDEHYDE
2-nitro-benzaldehyd
Benzaldehyde, o-nitro-
Benzaldehyde,2-nitro-
o-nitro-benzaldehyd
2-Nitobenzaldehyde
o-nitrobbenzaldehyde
o-Nitrobenzaldehyde(2-Nitrobenzaldehyde)
2-NITROBENZALDEHYDE, FOR THE DETERM. OF METHYL KETONES
2-NitrobenzaldehydeGr
O-Nitrobenzaldehyde99.5%
2-Nitrobenzaldehyde, 98+%
2-Nitrobenzaldehyde, 99+%
O-NITROBENZALDEHYDE (ORTHO-NITROBENZALDEHYDE) | [EINECS(EC#)]
209-025-3 | [Molecular Formula]
C7H5NO3 | [MDL Number]
MFCD00007132 | [Molecular Weight]
151.12 | [MOL File]
552-89-6.mol |
| Chemical Properties | Back Directory | [Appearance]
YELLOW CRYSTALLINE POWDER OR NEEDLES | [Melting point ]
42-44 °C(lit.)
| [Boiling point ]
153 °C23 mm Hg(lit.)
| [bulk density]
350kg/m3 | [density ]
1,284 g/cm3 | [vapor density ]
5.2 (vs air)
| [refractive index ]
1.5800 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Store at RT. | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Crystalline Powder, Needles and/or Chunks | [color ]
Yellow | [Water Solubility ]
Insoluble in water. | [Sensitive ]
Air Sensitive | [Detection Methods]
GC,NMR | [Merck ]
14,6587 | [BRN ]
742624 | [LogP]
1.74 at 25℃ | [CAS DataBase Reference]
552-89-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzaldehyde, 2-nitro-(552-89-6) | [EPA Substance Registry System]
552-89-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R68:Possible risk of irreversible effects. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
CU7300000
| [F ]
8 | [Autoignition Temperature]
200 °C (Lit.) | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29130000 |
| Hazard Information | Back Directory | [Chemical Properties]
YELLOW CRYSTALLINE POWDER OR NEEDLES | [Uses]
2-Nitrobenzaldehyde is a benzaldhyde with a nitro group substituted in the ortho position. 2-Nitrobenzaldehyde is used in the preparation of dyes and colorants such as Indigo carmine. 2-Nitrobenzaldeh
yde gas been shown to be a useful photoremovable protecting group as well as in the preparation of more effective ones such as o-Nitrophenylethylene glycol. | [Application]
2-Nitrobenzaldehyde can react with chitosan to form 2-nitrobenzyl-chitosan, which is soluble in trifluoroacetic acid and can also be electrospun into nanofiber matrices. On photolysis, the nitrobenzyl group is cleaved to form neat chitosan nanofiber matrices. The same principle has been applied for the preparation of gelatin nanofiber matrices. The condensation of o-NBA with 2-aminobenzothiazole forms o-nitrobenzylidene 2-aminobenzothiazole, a Schiff′s base that can react with metal ions to form complexes. | [Definition]
ChEBI: Benzaldehyde substituted at the ortho-position with a nitro group. | [Preparation]
2-Nitrobenzaldehyde is synthesized from 2-Nitrotoluene by nitration and oxidation.
Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene | [Synthesis Reference(s)]
Synthetic Communications, 19, p. 3385, 1989 DOI: 10.1080/00397918908052745 | [General Description]
The 2-Nitrobenzyl group of 2-nitrobenzaldehyde is photolabile that can be cleaved when exposed to UV-light. | [Synthesis]
50 g (0.24 mol) of 2-nitrophenylpyruvic acid of melting point 115° C are introduced into 500 ml of aqueous sodium carbonate until a clear solution is obtained. After the addition of 350 ml of toluene, the mixture is cooled to 0° C, and 40 g of solid potassium permanganate is then added in portions at 0°- 3° C. After one hour at 0°- 3° C, 95 ml of 50% strength sulphuric acid are added dropwise. The temperature is not allowed to rise above 30° C. The reaction mixture is filtered, and the toluene phase is separated from the filtrate. The filter residue is washed with toluene, and the combined toluene phases are extracted with 15% strength sodium carbonate solution and with water. The toluene phase is then dried with sodium sulfate and concentrated in a vacuo. The remaining residue consists of 19.7 g (54.7% of theory) of 2-nitrobenzaldehyde, which crystallizes on cooling.
| [Purification Methods]
Crystallise the aldehyde from toluene (2-2.5mL/g) by addition of 7mL pet ether (b 40-60o) for 1mL of solution. It can also be distilled under reduced pressures. [Beilstein 7 IV 584.] |
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