1-Chloro-2-nitrobenzene

Structural formula

• Numbering system
• Physical property data
• Toxicological data
• Ecological data
• Molecular structure data
• Computing chemical data
• More
  • Properties and Stability
  • Storage method
  • Synthesis method
  • Purpose

Numbering system

CAS number:88-73-3

MDL number:MFCD00007061

EINECS number:201-854-9

RTECS number:CZ0875000

BRN number:509273

PubChem number:24869530

Physical property data

1. Properties: light yellow needle-like crystals. It has an odor similar to nitrobenzene.

2. Density (g/cm3): 1.348

3. Melting point (ºC): 34~35

4. Boiling point (ºC, normal pressure) :245~246

5. Flash point (ºC): 127.22

6. Vapor pressure (kPa, 119ºC): 1.07

7. Solubility: Insoluble in water, soluble in ethanol, ether and benzene.

Toxicological data

Corrosive. It can be absorbed through the respiratory tract, digestive tract, and skin and invade the human body. It has an irritating effect on mucous membranes and skin and causes methemoglobinemia, thereby causing tissue hypoxia.

Ecological data

It is toxic to aquatic organisms and can cause long-term harmful consequences to the aquatic environment.

Molecular structure data

1. Molar refractive index: 37.69

2. Molar volume (cm³/mol): 113.2

3. Isotonic specific volume (90.2K ): 298.6

4. Surface tension (dyne/cm): 48.3

5. Polarizability (10^-24cm³): 14.94

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 2

4. Number of rotatable chemical bonds: 0

5. Number of tautomers: none

6. Topological molecule polar surface area 45.8

7. Number of heavy atoms: 10

8. Surface charge: 0

9. Complexity: 134

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

Further nitrification produces 2,6- and 2,4-dinitrochlorobenzene. Extremely poisonous! It damages the human body’s hematopoietic system and nervous system, and causes human poisoning through absorption through the human respiratory system and skin. The maximum allowable concentration in the air is 1mg/m3.

Storage method

This product should be sealed and stored in a cool, dark place.

Synthesis method

Mixed nitrochlorobenzene is obtained from nitrification of chlorobenzene with mixed acid. The contents of the three isomers are roughly as follows: p-nitrochlorobenzene accounts for 65%, o-nitrochlorobenzene accounts for 30%, and m-nitrochlorobenzene accounts for 1%. The process is as follows: First, add the prepared mixed acid (containing 30% nitric acid, 56% sulfuric acid, and 14% water) into the nitrification pot. Maintain the temperature at 40-55°C, slowly add chlorobenzene, raise the temperature to 80°C after addition, and stir for 2 hours. Leave to stand and separate into layers. Wash the upper layer of mixed nitrochlorobenzene with water and alkali. After washing with water, leave to stand and separate. Heat to 100°C and dry in a vacuum to obtain mixed nitrochlorobenzene. Then in the crystallizer, the above-mentioned dried mixed nitrochlorobenzene is gradually cooled to 15°C, that is, a large amount of p-nitrochlorobenzene collects on the tube wall, is heated and melted, stored in a storage tank, and vacuum distilled to remove chlorine. After benzene, p-nitrochlorobenzene is obtained. The mother liquor discharged from the lower part of the crystallizer contains about 35% p-nitrochlorobenzene, 64% o-nitrochlorobenzene and a small amount of m-nitrochlorobenzene for further separation. The crude o-nitrochlorobenzene separated by distillation is then crystallized in a crystallizer by lowering the temperature in the crystallizer to 15°C to obtain the finished product. Raw material consumption quota: p-nitrochlorobenzene, chlorobenzene 1150kg/t, nitric acid 672kg/t, sulfuric acid (92.5%) 632kg/t.

Purpose

O-Nitrochlorobenzene is an important organic synthesis intermediate and can derive a variety of intermediates. In the dye industry, it is used to make yellow-based GC, orange-based GR, etc.; in terms of additives, it is used to make rubber accelerators M and DM, etc.; in the spice industry, it is used for the synthesis of vanillin; in the pesticide industry, it is used to produce thiophanate and Thiophanate methyl, carbendazim; it is also the raw material of benzotriazole ultraviolet absorbers. It is also an important intermediate in medicine.