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100-02-7

Basic Information
CAS No.: 100-02-7
Name: 4-Nitrophenol
Article Data: 2114
Molecular Structure:
Molecular Structure of 100-02-7 (4-Nitrophenol)
Formula: C6H5NO3
Molecular Weight: 139.111
Synonyms: Phenol,p-nitro- (8CI);1-Hydroxy-4-nitrobenzene;4-Hydroxy-1-nitrobenzene;4-Hydroxynitrobenzene;Phenol, 4-nitro-;Niphen;p-Hydroxynitrobenzene;p-Nitrophenol;
EINECS: 202-811-7
Density: 1.395 g/cm3
Melting Point: 112-114 °C
Boiling Point: 279 °C at 760 mmHg
Flash Point: 141.9 °C
Solubility: 1.6 g/100 mL (25 °C) in water
Appearance: Yellow to brown crystals
Hazard Symbols: HarmfulXn,ToxicT,FlammableF
Risk Codes: 20/21/22-33-39/23/24/25-23/24/25-11
Safety: 28-28A-45-36/37-16-7
Transport Information: UN 1663 6.1/PG 3
PSA: 66.05000
LogP: 1.82360
Synthetic route
1568-66-7

1-allyloxy-4-nitrobenzene

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;100%
With chloro-trimethyl-silane; sodium cyanoborohydride In acetonitrile at 20℃; for 0.25h; ether cleavage;95%
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h;94%
880-03-5

1-(methoxymethoxy)-4-nitrobenzene

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1h;100%
With diphosphorus tetraiodide In dichloromethane at 0℃; for 0.75h;92%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 3h;92%
With Montmorillonite K 10 In benzene at 50℃; for 72h;20%
133754-19-5

trans-2-(p-nitrophenoxy)-6-carboxytetrahydropyran

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With sodium hydroxide; potassium chloride at 50℃; Rate constant; Mechanism; var. pH; other acetals; other solvent; rate constant vs. pH;100%
830-03-5

4-nitrophenol acetate

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 8h;100%
With ammonium acetate In methanol at 20℃; for 2h;99%
With Vigna unguiculata powder In water; isopropyl alcohol at 30℃; for 72h;99%
13165-89-4

4-nitrophenyl methylsulphonylmethanesulphonate

100-46-9

benzylamine

A

100-02-7

4-nitro-phenol

B

N-benzyl (methylsulfonyl)methanesulfonamide

Conditions
ConditionsYield
With pH 13 In water at 25℃;A n/a
B 100%
With potassium hydroxide at 25℃; Rate constant; also with benzylamine buffers; var. conc.;

1-(1,1-dimethyl-allyloxy)-4-nitro-benzene

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h;100%
13303-10-1

tert-Butyl 4-nitrophenyl carbonate

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With erbium(III) triflate In ethanol for 25h; Microwave irradiation;100%
With methanol; carbon tetrabromide; triphenylphosphine for 12h; Reflux;92%
With zinc diacetate; water-d2; N-ethyl-N,N-diisopropylamine; tris(2-benzylaminoethyl)amine In dimethylsulfoxide-d6 at 21.84℃; Kinetics; Reagent/catalyst;
24067-17-2

4-nitrophenylboronic acid

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With water; oxygen; sodium sulfite at 50℃; for 1h; Green chemistry;100%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 30h; Irradiation; Green chemistry;99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 48h; Irradiation;99%
100-01-6

4-nitro-aniline

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With water; sodium hydroxide at 150℃; for 0.1h; Autoclave;100%
Stage #1: 4-nitro-aniline With tetrafluoroboric acid In water at 20℃; for 0.0333333h;
Stage #2: With sodium nitrite In water at 0℃; for 0.5h;
Stage #3: With copper(I) oxide; copper(II) sulfate In water at 0 - 20℃; for 0.5h;
87%
Stage #1: 4-nitro-aniline With sulfuric acid In water
Stage #2: With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 0.166667h; Heating;
60%
60-12-8

2-phenylethanol

1080-04-2

p-nitrophenyl sulfate

A

100-02-7

4-nitro-phenol

B

2-phenylethyl sulfate

Conditions
ConditionsYield
With arylsulfate sulfotransferase from Desulfitobacterium hafniense In acetone at 30℃; for 96h; pH=9; Kinetics; pH-value; Green chemistry; Enzymatic reaction; regioselective reaction;A n/a
B 100%
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    Name 4-Nitrophenol Synonyms p-Nitrophenol; 1-Hydroxy-4-nitrobenzene Molecular Structure Molecular Formula

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EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

Specification

The 4-Nitrophenol with CAS registry number of 100-02-7 is also known as Phenol, 4-nitro-. The IUPAC name and product name are the same. It belongs to product categories of Organics; Phenoles and thiophenoles; Analytical Chemistry; Biochemistry; Coupling Reactions (Peptide Synthesis); Indicator (pH); Peptide Synthesis; pH Indicators. Its EINECS registry number is 202-811-7. In addition, the formula is C6H5NO3 and the molecular weight is 139.11. This chemical is a yellow to brown crystal and should be sealed in ventilated, cool room away from fire and heat. What's more, this chemical is soluble in sodium carbonate, sodium hydroxide solution, and other organic solvents such as ethanol, ether, chloroform and benzene.

Physical properties about 4-Nitrophenol are: (1)ACD/LogP: 1.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.66; (4)ACD/LogD (pH 7.4): 1.272; (5)ACD/BCF (pH 5.5): 10.707; (6)ACD/BCF (pH 7.4): 4.385; (7)ACD/KOC (pH 5.5): 188.961; (8)ACD/KOC (pH 7.4): 77.385; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.612; (13)Molar Refractivity: 34.68 cm3; (14)Molar Volume: 99.705 cm3; (15)Surface Tension: 60.24 dyne/cm; (16)Density: 1.395 g/cm3; (17)Flash Point: 141.896 °C; (18)Enthalpy of Vaporization: 53.846 kJ/mol; (19)Boiling Point: 278.999 °C at 760 mmHg; (20)Vapour Pressure: 0.002 mmHg at 25 °C.

Preparation of 4-Nitrophenol: it is prepared by hydrolysis reaction of chloronitrobenzene.

4-Nitrophenol is prepared by hydrolysis reaction of chloronitrobenzene.

Uses of 4-Nitrophenol: it is used as an intermediate in the synthesis of paracetamol and also is used for the preparation of phenetidine or acetophenetidine, indicators and raw materials for fungicides. What's more, it is used to produce methyl-phosphonic acid bis-(4-nitro-phenyl ester) by reaction with methyl-phosphonic acid dichloride. The reaction occurs with reagent Et3N and solvent CH2Cl2 at 20 °C for 1 hour. The yield is about 52%.

4-Nitrophenol is used to produce methyl-phosphonic acid bis-(4-nitro-phenyl ester) by reaction with methyl-phosphonic acid dichloride.

When you are using this chemical, please be cautious about it. As a chemical, it is harmful and danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. Besides, it is highly flammable and has danger of cumulative effects. During using it, wear suitable protective clothing and gloves. Keep away from sources of ignition. After using it, keep container tightly closed. If contact with skin, wash immediately. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])O
2. InChI: InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
3. InChIKey: BTJIUGUIPKRLHP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 unreported 150mg/kg (150mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 97, 1971.
dog LDLo intravenous 10mg/kg (10mg/kg)   U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 131, 1941.
frog LDLo subcutaneous 60mg/kg (60mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.
guinea pig LD50 skin > 1gm/kg (1000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" National Technical Information Service. Vol. OTS0570918,
guinea pig LDLo subcutaneous 200mg/kg (200mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.
mammal (species unspecified) LD50 oral 247mg/kg (247mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mammal (species unspecified) LD50 skin 920mg/kg (920mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mammal (species unspecified) LD50 unreported 175mg/kg (175mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(11), Pg. 13, 1974.
mouse LD50 intracrebral 90mg/kg (90mg/kg)   Pesticide Biochemistry and Physiology. Vol. 8, Pg. 302, 1978.
mouse LD50 intraperitoneal 75mg/kg (75mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 282mg/kg (282mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
National Technical Information Service. Vol. OTS0570918,
pigeon LDLo intramuscular 65mg/kg (65mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933.
rabbit LDLo oral 600mg/kg (600mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. 0TS0518150,
rabbit LDLo skin 1500mg/kg (1500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS
National Technical Information Service. Vol. 0TS0518150,
rat LD50 oral 202mg/kg (202mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. 0TS0518152,
rat LD50 skin 1024mg/kg (1024mg/kg)   National Technical Information Service. Vol. 0TS0516686,
rat LDLo subcutaneous 200mg/kg (200mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.