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2-Nitrobenzaldehyde

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2-Nitrobenzaldehyde Basic information

Product Name:
2-Nitrobenzaldehyde
Synonyms:
  • 2-nitro-benzaldehyd
  • Benzaldehyde, o-nitro-
  • Benzaldehyde,2-nitro-
  • o-nitro-benzaldehyd
  • 1-ForMyl-2-nitrobenzene
  • 2-ForMyl-3-nitrobenzene
  • 2-NBA
  • 2-Nitrobenzenecarboxaldehyde
CAS:
552-89-6
MF:
C7H5NO3
MW:
151.12
EINECS:
209-025-3
Product Categories:
  • Pharmaceutical intermediates
  • Chemical Synthesis
  • Nifedipine
  • Building Blocks
  • Carbonyl Compounds
  • Organic Building Blocks
  • Benzaldehyde
  • Aldehydes
  • C7
  • Carbonyl Compounds
  • 552-89-6
Mol File:
552-89-6.mol
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2-Nitrobenzaldehyde Chemical Properties

Melting point:
42-44 °C(lit.)
Boiling point:
153 °C23 mm Hg(lit.)
Density 
1,284 g/cm3
vapor density 
5.2 (vs air)
refractive index 
1.5800 (estimate)
Flash point:
>230 °F
storage temp. 
Store below +30°C.
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly)
form 
Crystalline Powder, Needles and/or Chunks
color 
Yellow
Water Solubility 
Insoluble in water.
Sensitive 
Air Sensitive
Merck 
14,6586
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
Benzaldehyde, 2-nitro- (552-89-6)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38-68
Safety Statements 
26-24/25-36/37/39-36
WGK Germany 
2
RTECS 
CU7300000
8
Autoignition Temperature
200 °C (Lit.)
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29130000

MSDS

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2-Nitrobenzaldehyde Usage And Synthesis

Chemical Properties

yellow or bright yellow needle-like crystals. It can volatilize with water vapor and has the fragrance of benzaldehyde. Soluble in ethanol, ether, benzene, slightly soluble in water, flash point>110℃, reacts violently with pyrrole.

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-Nitrobenzaldehyde 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.

Definition

ChEBI: 2-nitrobenzaldehyde is benzaldehyde substituted at the ortho-position with a nitro group. It is a C-nitro compound and a member of benzaldehydes.

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.

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.

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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