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2-Methyl-4,6-dinitrophenol
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Name

2-Methyl-4,6-dinitrophenol

 EINECS 208-601-1
CAS No. 534-52-1 Density 1.55 g/cm3
PSA 111.87000 LogP 2.56340
Solubility slightly soluble Melting Point 83-85 ºC
Formula C7H6 N2 O5 Boiling Point 332.4 °C at 760 mmHg
Molecular Weight 198.135 Flash Point 149.2 °C
Transport Information UN 1598 Appearance straw yellow to yellow crystal
Safety Human poison by unspecified route. Experimental poison by ingestion, inhalation, skin contact, intraperitoneal, and intravenous routes. Human systemic effects by ingestion and inhalation: somnolence, headache, abnormal brain recordings from specific areas of the central nervous system, cardiac and gastrointestinal changes. Mutation data reported. An eye and skin irritant. Less toxic than the para form, but is still highly toxic. A pesticide. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and 3,5-DINITRO-o-CRESOL; 3,5-DINITRO-p-CRESOL; 2,6-DINITRO-p-CRESOL; 4,6-DINITRO-m-CRESOL; 4,6-DINITRO-o-CRESOL AMMONIUM SALT; 4,6-DINITRO-o-CRESOL BARIUM DERIVATIVE; 4,6-DINITRO-o-CRESOL DIETHYLAMINE SALT; 4,6-DINITRO-o-CRESOL METHYLAMINE (1:1); 4,6-DINITRO-o-CRESOL MORPHOLINE (1:1); 4,6-DINITRO-o-CRESOL SODIUM SALT.

Analytical Methods:

   

For occupational chemical analysis use NIOSH: Dinitro-o-cresol S166.

Risk Codes R26/27/28;R38;R40;R41;R43;R44;R50/53   
Molecular Structure Molecular Structure of 534-52-1 (2-Methyl-4,6-dinitrophenol) Hazard Symbols
Synonyms

o-Cresol,4,6-dinitro- (8CI);2,4-Dinitro-6-methylphenol;2-Methyl-4,6-dinitrophenol;3,5-Dinitro-2-hydroxytoluene;4,6-Dinitro-2-methylphenol;4,6-Dinitro-o-cresol;6-Methyl-2,4-dinitrophenol;Antinonin;Antinonnin;Arborol;DNOC;Degrassan;Dekrysil;Detal;Dillex;Dinitro;Dinitrocresol;Dinitrodendtroxal;Dinitrol;Dinoc;Dinurania;Ditrosol;Effusan;Effusan 3436;Elgetol;Elgetol 30;Elipol;Extrar;Flavin-Sandoz;Hedolit;Hedolite;K III;KIV;Kreozan;Krezotol 50;Lipan;NSC 2082;Neudorff DN 50;Nitrofan;Prokarbol;Rafex;Rafex 35;Raphatox;Sandolin;Sandolin A;Selinon;Sinox;Winterwash;

Article Data 74

2-Methyl-4,6-dinitrophenol Synthetic route

95-48-7

ortho-cresol

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With (NH4)2Ce(NO3)6 on pillared bentonite In methanol at 25℃; for 48h;100%
With thionyl chloride; bismuth subnitrate In dichloromethane at 20℃; for 2h;83%
With cupric nitrate trihydrate supported on K 10 montmorillonite clay; nitric acid; acetic anhydride In tetrachloromethane for 1h; Ambient temperature;80%
95-48-7

ortho-cresol

A

13073-29-5

2-methyl-6-nitrophenol

B

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With zirconyl nitrate In acetone at 20℃; for 0.45h;A 43%
B 52%
With bismuth(III) nitrate In acetone at 20℃; for 0.0666667h;A 35%
B 45%
95-48-7

ortho-cresol

A

99-53-6

2-methyl-4-nitrophenol

B

13073-29-5

2-methyl-6-nitrophenol

C

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With Montmorillonite KSF; nitric acid; hafnium oxychloride In tetrahydrofuran at 20℃; for 16h;A 36%
B 46%
C 4%
With Yb-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h;A 45%
B 39%
C 9%
With Eu-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h;A 42%
B 40%
C 9%
With Montmorillonite KSF; nitric acid; bismuth(III) nitrate In tetrahydrofuran at 20℃; for 16h;A 26%
B 24%
C 22%
With sulfuric acid; calcium(II) nitrate In water at 2℃; for 5h; Product distribution; other substituted phenols; other nitrating agent, var. temp.;
81484-48-2

2-Methyl-4-cyclopropyl-6-nitrophenol

A

534-52-1

2-methyl-4,6-dinitrophenol

B

95970-37-9

5,6-Dinitro-2-methyl-4-cyclopropylphenol

C

96020-52-9

3-Nitrooxy-1-(3-methyl-4-hydroxy-5-nitrophenyl)-1-propanol

D

95970-36-8

3,4,6-Trinitro-2-hydroxy-2-methyl-4-cyclopropyl-5-cyclohexen-1-one

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -10℃; for 3h; Product distribution;A 30%
B 18%
C 10%
D 17%
64-17-5

ethanol

90084-63-2

2-hydroxy-toluene-3,5-disulfonyl chloride

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
anschliessen Behandeln mit 2n-Salpetersaeure;
98-27-1

2-Methyl-4-t-butylphenol

A

20294-44-4

5-Nitro-6-hydroxy-1-methyl-3-tert.-butyl-benzol

B

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With nitric acid; benzene
98-27-1

2-Methyl-4-t-butylphenol

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With nitric acid; acetic acid at -20℃;
With nitric acid; benzene unter Kuehlung;
578-58-5

2-methylmethoxybenzene

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With sulfuric acid; acetic acid; sodium nitrite at 0℃;
Multi-step reaction with 2 steps
1: glacial acetic acid; nitrosylsulfuric acid / -15 - -10 °C
2: diluted nitric acid / 40 °C
View Scheme
Multi-step reaction with 2 steps
1: nitric acid
2: NaOH-solution
View Scheme
611-23-4

2-nitrosotoluene

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With nitric acid; cis-nitrous acid Erwaermen der erhaltenen Diazoniumsalz-Loesung auf 35-50grad;
20294-44-4

5-Nitro-6-hydroxy-1-methyl-3-tert.-butyl-benzol

534-52-1

2-methyl-4,6-dinitrophenol

Conditions
ConditionsYield
With nitric acid

2-Methyl-4,6-dinitrophenol Chemical Properties

Molecular Formula:C7H6N2O5
Molecular Weight:198.15
EINECS:208-601-1
Density:1.55 g/cm3
Melting Point:83-85°C
Boiling Point:332.4 °C at 760 mmHg
Flash Point:149.2 °C
Storage temp.:0-6°C
Solubility:slightly soluble
Appearance:straw yellow to yellow crystal
DINITRO-o-CRESOL's Synonyms: 3,5-DINITRO-2-HYDROXYTOLUENE;4,6-DINITRO-2-METHYLPHENOL;4,6-DINITRO-O-CRESOL;4,6-DNOC;TRIFANEX;TRIFOCIDE;TRIFOCIDE(R);TRIFRINA

2-Methyl-4,6-dinitrophenol Toxicity Data With Reference

1.   

skn-rbt 105 mg/9D-I MLD

   JIHTAB    Journal of Industrial Hygiene and Toxicology. 30 (1948),10.
2.   

eye-rbt 20 mg/24H MOD

   85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,678.
3.   

mma-sat 1 µmol/plate

   AIDZAC    Aichi Ika Daigaku Igakkai Zasshi. Journal of the Aichi Medical Univ. Assoc. 10 (1982),305.
4.   

sln-dmg-orl 250 µmol/L

   ARTODN    Archives of Toxicology.Suppl. 4(1980),59.
5.   

orl-man TDLo:7500 µg/kg/7D:CNS

   CMEP**    Clinical Memoranda on Economic Poisons US Dept. HEW, Public Health Service, Communicable Disease Center,Atlanta, GA.: 1956,1.
6.   

ihl-hmn TCLo:1 mg/m3:BRN,CVS,GIT

   HYSAAV    Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 30 (1965),197.
7.   

unr-man LDLo:29 mg/kg

   85DCAI    Poisoning; Toxicology, Symptoms, Treatments. 2 (1970),73.
8.   

orl-rat LD50:10 mg/kg

   85ARAE    Agricultural Chemicals, Books I, II, III, and IV. 3 (1976),54.
9.   

skn-rat LD50:200 mg/kg

   WRPCA2    World Review of Pest Control. 9 (1970),119.
10.   

ipr-rat LDLo:28 mg/kg

2-Methyl-4,6-dinitrophenol Consensus Reports

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

2-Methyl-4,6-dinitrophenol Safety Profile

Human poison by unspecified route. Experimental poison by ingestion, inhalation, skin contact, intraperitoneal, and intravenous routes. Human systemic effects by ingestion and inhalation: somnolence, headache, abnormal brain recordings from specific areas of the central nervous system, cardiac and gastrointestinal changes. Mutation data reported. An eye and skin irritant. Less toxic than the para form, but is still highly toxic. A pesticide. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and 3,5-DINITRO-o-CRESOL; 3,5-DINITRO-p-CRESOL; 2,6-DINITRO-p-CRESOL; 4,6-DINITRO-m-CRESOL; 4,6-DINITRO-o-CRESOL AMMONIUM SALT; 4,6-DINITRO-o-CRESOL BARIUM DERIVATIVE; 4,6-DINITRO-o-CRESOL DIETHYLAMINE SALT; 4,6-DINITRO-o-CRESOL METHYLAMINE (1:1); 4,6-DINITRO-o-CRESOL MORPHOLINE (1:1); 4,6-DINITRO-o-CRESOL SODIUM SALT.

DINITRO-o-CRESOL's Safety Information
Hazard Codes  T+,N,T,F
Risk Statements  26/27/28-38-41-43-44-50/53-68-40-39/23/24/25-23/24/25-11-52/53
Safety Statements  36/37-45-60-61-16-7
RIDADR  UN 1598 6.1/PG 2
WGK Germany  2
RTECS  GO9625000
HazardClass  6.1(a)
PackingGroup  II

2-Methyl-4,6-dinitrophenol Standards and Recommendations

OSHA PEL: TWA 0.2 mg/m3 (skin)
ACGIH TLV: TWA 0.2 mg/m3 (skin)
DFG MAK: 0.2 mg/m3
NIOSH REL: (Dinitro-o-Cresol) TWA 0.2 mg/m3
DOT Classification:  6.1; Label: Poison

2-Methyl-4,6-dinitrophenol Analytical Methods

For occupational chemical analysis use NIOSH: Dinitro-o-cresol S166.
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