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4-Nitrosalicylic acid

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Name

4-Nitrosalicylic acid

EINECS 210-584-0
CAS No. 619-19-2 Density 1.632 g/cm3
PSA 103.35000 LogP 1.52180
Solubility N/A Melting Point 235-239 °C(lit.)
Formula C7H5NO5 Boiling Point 389.046 °C at 760 mmHg
Molecular Weight 183.12 Flash Point 179.176 °C
Transport Information N/A Appearance White to yellow crystalline powder
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 619-19-2 (4-Nitrosalicylic acid) Hazard Symbols IrritantXi
Synonyms

Salicylicacid, 4-nitro- (7CI,8CI);2-Hydroxy-4-nitrobenzoic acid;4-Nitro-2-hydroxybenzoic acid;NSC 882;p-Nitrosalicylicacid;

Article Data 41

4-Nitrosalicylic acid Synthetic route

2597-56-0

4-nitro-o-anisic acid

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With boron tribromide In dichloromethane97%
With sulfuric acid
With hydrogen bromide
With hydrogen bromide; acetic acid at 90℃; for 72h;
2597-56-0

4-nitro-o-anisic acid

10294-33-4

boron tribromide

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 2h;97%
99-60-5

2-chloro-4-nitrobenzoic acid

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With pyridine; water; potassium carbonate; copper for 0.25h; sonication;96%
With pyridine; copper; potassium carbonate In water for 2h; Heating;90%
With quicklime; water; copper at 160 - 170℃;
With copper(l) iodide; copper; potassium carbonate
With calcium hydroxide; copper diacetate In water at 160℃; for 7h;
57356-40-8

2-(hydroxymethyl)-5-nitrophenol

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sodium hypochlorite; water at 25℃; for 0.5h;96%
With oxygen In acetonitrile at 20℃; for 8.5h; Catalytic behavior;85%
62-23-7

4-nitro-benzoic acid

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; under 3800.26 Torr; for 15h;91%
With oxygen; potassium acetate; p-benzoquinone; palladium diacetate In ISOPROPYLAMIDE at 115℃; under 3800.26 Torr; for 15h; Product distribution / selectivity;91%
With [Fe(II)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethylenediamine)(CH3CN)2](ClO4)2; dihydrogen peroxide In water; acetonitrile at 20℃; Inert atmosphere; regioselective reaction;68 %Spectr.
69-72-7

salicylic acid

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sodium perborate hexahydrate; hydroquinone; sodium nitrite In neat (no solvent) for 0.0333333h; Molecular sieve; Microwave irradiation; regioselective reaction;75%
With potassium hydrogensulfate; potassium metaperiodate; silica gel; sodium nitrite In neat (no solvent) for 0.0833333h; Reagent/catalyst; Solvent; Microwave irradiation;69%
With potassium hydrogensulfate; potassium metaperiodate; sodium nitrite In water; acetonitrile at 44.84℃; Kinetics; Temperature;
13684-28-1

2-hydroxy-4-nitro-benzoic acid methyl ester

62-23-7

4-nitro-benzoic acid

A

619-50-1

4-nitrobenzoic acid methyl ester

B

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
Stage #1: 4-nitro-benzoic acid With potassium carbonate In N,N-dimethyl acetamide at 90℃; for 0.5h;
Stage #2: 2-hydroxy-4-nitro-benzoic acid methyl ester at 90℃; for 24h;
A 32%
B n/a
5428-54-6

2-methyl-5-nitrophenol

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate
50603-43-5

7-nitro-4H-benzo[1,3]dioxine

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate; acetic acid
39835-14-8

2-hydroxy-4-nitro-benzonitrile

619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid Siedetemperatur;
With hydrogenchloride at 160℃; Reinigung ueber das Barium-Salz;
With sulfuric acid; acetic acid Siedetemperatur;

4-Nitrosalicylic acid Consensus Reports

Reported in EPA TSCA Inventory.

4-Nitrosalicylic acid Specification

The 4-Nitrosalicylic acid, with the CAS registry number 619-19-2, is also known as 4-Nitro-2-hydroxybenzoic acid. It belongs to the product categories of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; C7; Carbonyl Compounds; Carboxylic Acids. Its EINECS number is 210-584-0. This chemical's molecular formula is C7H5NO5 and molecular weight is 183.12. What's more, its systematic name is 2-Hydroxy-4-nitrobenzoic acid. 

Physical properties of 4-Nitrosalicylic acid are: (1)ACD/LogP: 2.859; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.27; (4)ACD/LogD (pH 7.4): -0.29; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 103.35 Å2; (13)Index of Refraction: 1.664; (14)Molar Refractivity: 41.61 cm3; (15)Molar Volume: 112.234 cm3; (16)Polarizability: 16.495×10-24cm3; (17)Surface Tension: 84.1 dyne/cm; (18)Density: 1.632 g/cm3; (19)Flash Point: 179.176 °C; (20)Enthalpy of Vaporization: 67.326 kJ/mol; (21)Boiling Point: 389.046 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of 4-Nitrosalicylic acid: it can be used to produce 2-methoxy-4-nitro-benzoic acid methyl ester at the temperature of 20 °C. It will need solvent diethyl ether with the reaction time of 4 hours. The yield is about 96%.

4-Nitrosalicylic acid can be used to produce 2-methoxy-4-nitro-benzoic acid methyl ester at the temperature of 20 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1ccc(cc1O)[N+]([O-])=O
(2)Std. InChI: InChI=1S/C7H5NO5/c9-6-3-4(8(12)13)1-2-5(6)7(10)11/h1-3,9H,(H,10,11)
(3)Std. InChIKey: UKWUOTZGXIZAJC-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 375mg/kg (375mg/kg)   Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie. Vol. 6B, Pg. 183, 1951.
mouse LD50 oral 650mg/kg (650mg/kg)   Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie. Vol. 6B, Pg. 183, 1951.

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