m-Nitrobenzoyl chloride

Reported in EPA TSCA Inventory.

The CAS registry number of m-Nitrobenzoyl chloride is 121-90-4. Its EINECS registry number is 204-505-9. In addition, the molecular formula is C₇H₄ClNO₃ and the molecular weight is 185.56. The systematic name is 3-nitrobenzoyl chloride. What's more, it is a kind of brown low melting solid and soluble in ether, benzene. And it can be used as a pharmaceutical intermediate.

Physical properties about this chemical are: (1)ACD/LogP: 2.12; (2)ACD/LogD (pH 5.5): 2.12; (3)ACD/LogD (pH 7.4): 2.12; (4)ACD/BCF (pH 5.5): 24.08; (5)ACD/BCF (pH 7.4): 24.08; (6)ACD/KOC (pH 5.5): 339.28; (7)ACD/KOC (pH 7.4): 339.28; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 62.89 Å²; (11)Index of Refraction: 1.589; (12)Molar Refractivity: 43.04 cm³; (13)Molar Volume: 127.6 cm³; (14)Polarizability: 17.06 ×10^-24cm³; (15)Surface Tension: 54.2 dyne/cm; (16)Density: 1.453 g/cm³; (17)Flash Point: 121.5 °C; (18)Enthalpy of Vaporization: 51.58 kJ/mol; (19)Boiling Point: 277.3 °C at 760 mmHg; (20)Vapour Pressure: 0.00457 mmHg at 25°C.

Preparation of m-Nitrobenzoyl chloride: it can be prepared by m-nitrobenzoic acid and phosgene. Mix m-nitrobenzoic acid, benzene and dimethylcarboxamide at first. Then heat the mixture to 40-50 °C. Next, pass the phosgene into the mixture. After this step, you can pass nitrogen into the mixture to remove residual phosgene. And then after a series of distillation and vacuum distillation you can get the desired product.

Uses of m-Nitrobenzoyl chloride: it can be used to get 3-nitro-benzoic acid-anhydride. This reaction will need reagents Co(PPh₃)₂Cl₂, Bu₄NBr and NaHCO₃, and solvent acetonitrile. The reaction time is 12 hours at reaction temperature of 120 °C. The yield is about 97%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause an explosion when heat it. And it is irritating to the respiratory system and harmful in contact with skin. Moreover, it may cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). You should keep container tightly closed and in a well-ventilated place when store it.

You can still convert the following datas into molecular structure:
(1)SMILES: O=[N+]([O-])c1cc(C(Cl)=O)ccc1
(2)Std.InChI: InChI=1S/C7H4ClNO3/c8-7(10)5-2-1-3-6(4-5)9(11)12/h1-4H
(3)Std.InChIKey: NXTNASSYJUXJDV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	790uL/kg (0.79mL/kg)		American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat	LD50	oral	2460uL/kg (2.46mL/kg)		American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.