3-Nitrobenzaldehyde Property

Melting point:

56 °C

Boiling point:

285-290 °C

Density 

1.2792

vapor density 

5.21 (vs air)

refractive index 

1.5800 (estimate)

Flash point:

164°C/23mm

storage temp. 

Store below +30°C.

solubility 

1.6g/l

form 

Granular Powder

color 

Yellow to yellow-brown

Water Solubility 

Slightly soluble in water.

Sensitive 

Air Sensitive

Merck 

14,6587

BRN 

386795

LogP

1.47

CAS DataBase Reference

99-61-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 3-nitro-(99-61-6)

EPA Substance Registry System

Benzaldehyde, 3-nitro- (99-61-6)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-51/53-22

Safety Statements 

26-36-24/25-61-37/39-29

RIDADR 

UN3077

WGK Germany 

3

RTECS 

CU7250000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29130000

Toxicity

LD50 orally in Rabbit: 1075 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

3-Nitrobenzaldehyde Chemical Properties,Usage,Production

Description

3-Nitrobenzaldehyde, meta-nitrobenzaldehyde or m-nitrobenzaldehyde is an organic aromatic compound containing a nitro group meta-substituted to an aldehyde. 3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid.

Chemical Properties

yellowish to yellow-brown granular powder

Uses

3-Nitrobenzaldehyde is used in the synthesis of other organic compounds, ranging from pharmaceuticals to plastic additives and intermediate for the processing of perfume and flavoring compounds and in the preparation of certain aniline dyes.

Uses

3-Nitrobenzaldehyde is a benzaldhyde with a nitro group in the meta position.

Preparation

89 mL (1.7 mol) concentrated H2SO4 are filled in a 500 mL three-neck flask equipped with an internal thermometer and an addition funnel with pressure balance. Whilst cooling with an ice bath 45 mL (0.95 mol) fuming HNO3 are added carefully under stirring, the temperature must not exceed 10 °C. To this nitrating acid, 10.6 g (10.2 mL, 100 mmol) benzaldehyde are added under further cooling so that the temperature can be constantly kept at 15 °C (about 1 hour). The ice bath is removed and the reaction mixture is stored over night at room temperature.
The reaction mixture is poured in a 1 L beaker on 500 g crunched ice, the yellow precipitation is sucked off at 16 hPa over a Buechner funnel and washed with 200 mL of cold water. Crude yield (humid): 14.4 g
The humid crude product is dissolved in 125 mL tert-butyl methyl ether and then shaken out with 125 mL of a 5% NaHCO3 solution. The organic phase is dried over sodium sulfate, filtered and the solvent evaporated at a rotary evaporator. The residue is recrystallized from toluene / petroleumether (60-80 °C) by dissolving it in toluene whilst heating and then adding the double amount of petroleum ether in portions under ice cooling. The crystalllized light yellow 3-nitrobenzaldehyde is sucked off over a Buechner funnel. The product is dried over silica gel in an evacuated desiccator.
Yield: 8.0 g (53 mmol, 53%); mp 56 °C

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 644, 1955
Tetrahedron Letters, 28, p. 1195, 1987 DOI: 10.1016/S0040-4039(00)95324-3

Purification Methods

Crystallise the aldehyde from water or EtOH/water, then sublime it twice at 2mm pressure at a temperature slightly above its melting point. [Beilstein 7 IV 591.]