ChemicalBook > CAS DataBase List > 2-Nitrobenzaldehyde

2-Nitrobenzaldehyde

Product Name
2-Nitrobenzaldehyde
CAS No.
552-89-6
Chemical Name
2-Nitrobenzaldehyde
Synonyms
2-NBA;2-nitro-benzaldehyd;O-NITROBENZALDEHYDE;2-Nitobenzaldehyde;1-ForMyl-2-nitrobenzene;2-Nitrobenzenecarboxaldehyde;NSC 5713;AKOS 93864;2-NitrobenzaL;AKOS BBS-00003153
CBNumber
CB8414184
Molecular Formula
C7H5NO3
Formula Weight
151.12
MOL File
552-89-6.mol
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2-Nitrobenzaldehyde Property

Melting point:
42-44 °C(lit.)
Boiling point:
153 °C23 mm Hg(lit.)
Density 
1,284 g/cm3
bulk density
350kg/m3
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

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.22293
Product name
2-Nitrobenzaldehyde
Purity
for synthesis
Packaging
1G
Price
$39.4
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22293
Product name
2-Nitrobenzaldehyde
Purity
for synthesis
Packaging
25G
Price
$69.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22293
Product name
2-Nitrobenzaldehyde
Purity
for synthesis
Packaging
100G
Price
$207
Updated
2024/03/01
TCI Chemical
Product number
N0130
Product name
2-Nitrobenzaldehyde
Purity
>99.0%(GC)
Packaging
25g
Price
$53
Updated
2024/03/01
TCI Chemical
Product number
N0130
Product name
2-Nitrobenzaldehyde
Purity
>99.0%(GC)
Packaging
100g
Price
$154
Updated
2024/03/01
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2-Nitrobenzaldehyde Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

2-Nitrotoluene Hydrogen peroxide Nitric acid Government regulation

Preparation Products

2-Aminoquinoline 2-Quinolinecarboxaldehyde Solvent Yellow 114 2-methylquinolin-3-ol Nisoldipine BENZAMIDE, 4-METHOXY-N-[2-[2-(1-METHYL-2-PIPERIDINYL)ETHYL]PHENYL]- Nifedipine (1H-INDAZOL-3-YL)-ACETIC ACID 2-Aminobenzaldehyde
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View Lastest Price from 2-Nitrobenzaldehyde manufacturers

Dorne Chemical Technology co. LTD
Product
2-Nitrobenzaldehyde 552-89-6
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
2-Nitrobenzaldehyde 2-NBA 552-89-6
Price
US $65.00-20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-04
Hebei Mujin Biotechnology Co.,Ltd
Product
2-Nitrobenzaldehyde 552-89-6
Price
US $100.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5000KG
Release date
2021-05-18

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