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CAS No.: | 122-04-3 |
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Name: | 4-Nitrobenzoyl chloride |
Article Data: | 166 |
Molecular Structure: | |
Formula: | C7H4ClNO3 |
Molecular Weight: | 185.567 |
Synonyms: | p-Nitrobenzoic acid chloride;Benzoyl chloride, p-nitro-;p-Nitrobenzonyl chloride;Paranitrobenzoyl chloride;4-Nitrobenzoic acid chloride;Benzoyl chloride, 4-nitro-; |
EINECS: | 204-517-4 |
Density: | 1.453 g/cm3 |
Melting Point: | 71-74 °C(lit.) |
Boiling Point: | 277.8 °C at 760 mmHg |
Flash Point: | 121.8 °C |
Solubility: | Decomposes |
Appearance: | yellow needles or powder |
Hazard Symbols: | C |
Risk Codes: | 34 |
Safety: | 26-36/37/39-45 |
Transport Information: | UN 3261 8/PG 2 |
PSA: | 62.89000 |
LogP: | 2.49700 |
Conditions | Yield |
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Stage #1: (4-nitrophenyl)ethanone With pyridine; disulfur dichloride In chlorobenzene at 20℃; for 2.5h; Stage #2: With sulfuryl dichloride In chlorobenzene at 20 - 132℃; for 21h; Reagent/catalyst; Temperature; | 90% |
Stage #1: (4-nitrophenyl)ethanone With pyridine; sulfur monochloride In chlorobenzene at 20℃; Stage #2: With thionyl chloride In chlorobenzene at 20 - 132℃; | 71% |
With pyridine; disulfur dichloride at 70 - 138℃; for 21.5h; | 83 %Spectr. |
Conditions | Yield |
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With thionyl chloride In ethyl acetate for 2h; Heating; | 100% |
With thionyl chloride for 1h; Reflux; | 100% |
With thionyl chloride; N,N-dimethyl-formamide for 5h; Reflux; | 100% |
Conditions | Yield |
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With pyridine; triethylamine In toluene at 0 - 20℃; for 20h; | 90% |
Conditions | Yield |
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52.9% |
potassium 4-nitrobenzoate
4-nitro-benzoyl chloride
Conditions | Yield |
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With thionyl chloride; N,N-dimethyl-formamide at 70 - 75℃; for 0.5h; | 98.5% |
Conditions | Yield |
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In dichloromethane; N,N-dimethyl-formamide; benzene |
Conditions | Yield |
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With iron(III) chloride; Benzotrichlorid In benzene at 60℃; Rate constant; Mechanism; Thermodynamic data; various concentration ratios; | |
With trichloroisocyanuric acid In dichloromethane at 20℃; for 120h; Inert atmosphere; | |
With trichloroisocyanuric acid In dichloromethane at 20℃; for 4h; Inert atmosphere; Irradiation; | |
With N-chloro-succinimide; thio-xanthene-9-one In acetonitrile at 20℃; for 7h; Irradiation; |
Conditions | Yield |
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With hydrogenchloride; Nitroethane; chlorine |
Conditions | Yield |
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With benzene |
Conditions | Yield |
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With trichloroisocyanuric acid In dichloromethane at 20℃; for 120h; Inert atmosphere; |
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The IUPAC name of this chemical is 4-Nitrobenzoyl chloride. With the CAS registry number 122-04-3 and EINECS registry number 204-517-4, it is also named as p-nitrobenzonyl chloride. In addition, the molecular formula is C7H4ClNO3. What's more, it is a kind of yellow needles or powder and sensitive with moisture. Besides, it is incompatible with water, alcohols, strong oxidizing agents and strong bases.
Physical properties about this chemical are: (1)ACD/LogP: 2.17; (2)ACD/LogD (pH 5.5): 2.17; (3)ACD/LogD (pH 7.4): 2.17; (4)ACD/BCF (pH 5.5): 26.28; (5)ACD/BCF (pH 7.4): 26.28; (6)ACD/KOC (pH 5.5): 361.21; (7)ACD/KOC (pH 7.4): 361.21; (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: 121.8 °C; (18)Enthalpy of Vaporization: 51.64 kJ/mol; (19)Boiling Point: 277.8 °C at 760 mmHg; (20)Vapour Pressure: 0.00442 mmHg at 25°C.
Preparation of 4-Nitrobenzoyl chloride: At first, add p-nitrobenzoic acid and phosphorus pentylchloride into the oil bath with heating. After the reaction, you can recycle trichlorooxyphosphorus through vacuum distillation. And then via vacuum distillation you can obtain the crude of this product. Next, melt the crude into liquld and then add carbon tetrachloride. You get the desired product through filtration, cooling and crystallization.
Uses of 4-Nitrobenzoyl chloride: it can react with 2-hydroxy-1,2-diphenyl-ethanone to get a-(4-nitro-benzoyloxy)-deoxybenzoin. This reaction will need reagent pyridine. The reaction time is 15 minutes by heating. The yield is about 62%.
When you are using this chemical, please be cautious about it as the following:
This chemical can 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 can still convert the following datas into molecular structure:
(1)SMILES: O=[N+]([O-])c1ccc(C(Cl)=O)cc1
(2)Std.InChI: InChI=1S/C7H4ClNO3/c8-7(10)5-1-3-6(4-2-5)9(11)12/h1-4H
(3)Std.InChIKey: SKDHHIUENRGTHK-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 3440mg/kg (3440mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(9), Pg. 47, 1984. |
rabbit | LD50 | oral | 4750mg/kg (4750mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(9), Pg. 47, 1984. |
rat | LD50 | oral | 5600mg/kg (5600mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(9), Pg. 47, 1984. |