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5-Nitrosalicylaldehyde

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Name

5-Nitrosalicylaldehyde

EINECS 202-587-0
CAS No. 97-51-8 Density 1.5 g/cm3
PSA 83.12000 LogP 1.63610
Solubility Soluble in water (partly). Melting Point 125-128 °C(lit.)
Formula C7H5NO4 Boiling Point 300.2 °C at 760 mmHg
Molecular Weight 167.121 Flash Point 137.3 °C
Transport Information N/A Appearance yellow to brown crystals or powder
Safety 26-36-37/39 Risk Codes 36/38-36/37/38-22
Molecular Structure Molecular Structure of 97-51-8 (5-Nitrosalicylaldehyde) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Salicylaldehyde,5-nitro- (6CI,7CI,8CI);2-Formyl-4-nitrophenol;2-Hydroxy-5-nitrobenzaldehyde;5-Nitro-2-hydroxybenzaldehyde;6-Hydroxy-3-nitrobenzaldehyde;NSC 881;NSC 97387;

Article Data 88

5-Nitrosalicylaldehyde Synthetic route

90-02-8

salicylaldehyde

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With nitric acid; acetic acid at 20℃; for 6h;96%
With magnesium(II) nitrate hexahydrate; AMA at 20℃; for 0.666667h; Neat (no solvent); regioselective reaction;90%
With Vilsmeier reagent; potassium nitrate In neat (no solvent) at 100℃; under 1500.15 Torr; Reagent/catalyst; Temperature; Microwave irradiation;89%
1498-88-0

1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran)

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With ozone In methanol at -78℃; for 0.0833333h; Oxidation;94%
100-02-7

4-nitro-phenol

100-97-0

hexamethylenetetramine

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With phosphorus molybdenum vanadium heteropoly acid based ionic liquid at 85 - 95℃; for 3h;92.6%
With toluene-4-sulfonic acid In ethanol at 78℃; for 2h;89.4%
With trifluoroacetic acid at 70℃; for 6h; Temperature;72.5%
39224-61-8

2-hydroxy-5-nitrobenzyl alcohol

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With aluminium trichloride; 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 1.5h; Heating;92%
With 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate at 20℃; for 0.133333h;92%
With air; (acryl-TEMPO)-co-(allylamine-treated chlorophyll b-Co(III) complex) immobilized on SiO2-covered Fe3O4 magnetic nanoparticles In water at 25℃; for 0.666667h;90%
100-02-7

4-nitro-phenol

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With hexamethylenetetramine; trifluoroacetic acid at 85℃; for 15h; Duff Aldehyde Synthesis;92%
89-95-2

2-methyl-benzyl alcohol

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With zirconyl nitrate In acetone at 50℃; for 2h;91%
With calcium(II) nitrate In acetic acid for 0.0166667h; microwave irradiation;82%
at 20 - 85℃; for 0.00333333h; microwave irradiation;62%
1008105-70-1

2-(1-hydroxy-3-phenylprop-2-yn-1-yl)-4-nitrophenol

A

886-66-8

1,4-diphenyl-1,3-butadiyne

B

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 110℃; for 5h; Solvent; Temperature;A 91%
B n/a

2-hydroxy-5-nitrobenzaldehyde semicarbazone

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With tetrachlorosilane; silica gel In hexane; water for 0.5h; Heating;90%
24590-01-0

acetyloxy(2-acetyloxy-5-nitrophenyl)methyl acetate

A

97-51-8

5-Nitrosalicylaldehyde

B

177496-78-5

2-acetoxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
With bismuth(III) chloride In chloroform for 0.5h; deprotection; Heating;A 5%
B 80%
93044-40-7

2-hydroxy-5-nitrobenzaldehydephenylhydrazone

97-51-8

5-Nitrosalicylaldehyde

Conditions
ConditionsYield
With 3-carboxypyridinium chlorochromate In acetonitrile for 1.5h; Heating;77%

5-Nitrosalicylaldehyde Standards and Recommendations

Assay: 99% min. (HPLC)

5-Nitrosalicylaldehyde Specification

The IUPAC name of this chemical is 2-hydroxy-5-nitrobenzaldehyde. With the CAS registry number 97-51-8, it is also named as 5-Nitrosalicylaldehyde; Benzaldehyde, 2-hydroxy-5-nitro-. The product's categories are fine chemical & intermediates; aromatic aldehydes & derivatives (substituted); benzaldehyde; aldehydes; carbonyl compounds. In addition, this chemical is yellow to brown crystals or powder which is sensitive to air and light.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): -0.19; (5)ACD/BCF (pH 5.5): 6.12; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 88.2; (8)ACD/KOC (pH 7.4): 1.75; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.666; (13)Molar Refractivity: 41.43 cm3; (14)Molar Volume: 111.3 cm3; (15)Polarizability: 16.42×10-24 cm3; (16)Surface Tension: 70.5 dyne/cm; (17)Enthalpy of Vaporization: 56.19 kJ/mol; (18)Vapour Pressure: 0.000637 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 4; (21)Exact Mass: 167.021858; (22)MonoIsotopic Mass: 167.021858; (23)Topological Polar Surface Area: 83.1; (24)Heavy Atom Count: 12.

Preparation of 2-Hydroxy-5-nitrobenzaldehyde: It can be obtained by 1,3,5,7-tetraaza-adamantane and 4-nitro-phenol with the reagent 75percent polyphoshoric acid (PPA) at 100 °C. The reaction time is 2 hours and the yield is 69 %.

Uses of 2-Hydroxy-5-nitrobenzaldehyde: It is used as intermediates of medicine, spices, dyes and other organic synthesis. For example: It reacts with aniline to get 4-Nitro-2-(phenylimino-methyl)-phenol. This reaction needs reagent benzene and solvent ethanol at ambient temperature. The yield is 79 %.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES: O=Cc1cc(ccc1O)[N+]([O-])=O;
2. InChI: InChI=1/C7H5NO4/c9-4-5-3-6(8(11)12)1-2-7(5)10/h1-4,10H.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 672mg/kg (672mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0533628,
rat LD50 oral 799mg/kg (799mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0533615,

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