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)

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

F 

8

Autoignition Temperature

200 °C (Lit.)

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29130000

MSDS

• Language:English Provider:2-Nitrobenzaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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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.

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.]

2-Nitrobenzaldehyde(552-89-6)Related Product Information

• 2-Nitrobenzoic acid
• 4-tert-Butyl-2-nitrophenol
• 2-Nitrocinnamic acid
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• 4-Hydroxy-3-nitrobenzaldehyde
• 2-Nitrobenzyl alcohol
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• 3-NITRO BENZALDEHYDE
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