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99-08-1

Basic Information
CAS No.: 99-08-1
Name: Benzene,1-methyl-3-nitro-
Article Data: 180
Cas Database
Molecular Structure:
Molecular Structure of 99-08-1 (Benzene,1-methyl-3-nitro-)
Formula: C7H7NO2
Molecular Weight: 137.138
Synonyms: 1-Methyl-3-nitrobenzene;3-Methylnitrobenzene;m-Nitrophenylmethane;m-Nitrotoluol;
EINECS: 202-728-6
Density: 1.167 g/cm3
Melting Point: 15 °C
Boiling Point: 221.999 °C at 760 mmHg
Flash Point: 106.111 °C
Solubility: insoluble in water, soluble in benzene
Appearance: yellow-green liquid
Hazard Symbols: ToxicT,FlammableF
Risk Codes: 23/24/25-33-51/53-36/37/38-11
Safety: 36/37-45-61-37-28A-27-16
Transport Information: UN 1664 6.1/PG 2
PSA: 45.82000
LogP: 2.42640
Synthetic route
3958-57-4

1-bromomethyl-3-nitrobenzene

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium hydroxide In water at 60℃; for 1.5h; pH=12; Reagent/catalyst; Green chemistry;99%
With diethylzinc; tetrakis(triphenylphosphine) palladium(0) In hexane; N,N-dimethyl-formamide at 25℃; for 1h;63%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1.5h;72 % Turnov.
17933-03-8

m-tolylboronic acid

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate In toluene at 80℃; for 12h; Inert atmosphere;96%
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; Solvent; regioselective reaction;93%
With pyridine; copper(I) oxide; sodium nitrite In acetonitrile at 20℃;78%
108-44-1

1-amino-3-methylbenzene

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;95%
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 1h; pH=11; Green chemistry;88%
With sodium perborate tetrahydrate; cetyltrimethylammonim bromide In water at 60℃; for 12h; silica gel; Micellar solution; Green chemistry; regioselective reaction;53%
With sulfuric acid Diazotization.Behandlung der neutralisierten Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit;
With sulfuric acid Diazotization.Behandlung der neutralisierten Diazoniumsalz-Loesung mit NaNO2, CuSO4 und Cu2O;

C12H9N3O6S2

594-27-4

tetramethylstannane

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
palladium diacetate In tetrahydrofuran at 40℃; for 0.25h;90%
13506-76-8

2-methyl-6-nitrobenzoic acid

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With silver carbonate In dimethyl sulfoxide at 120℃; for 16h;86%
With silver carbonate In dimethyl sulfoxide at 120℃;
Multi-step reaction with 3 steps
1.1: sodium hydroxide / tetrahydrofuran; water / 0.17 h / Darkness
1.2: 0.08 h / Darkness
2.1: acetonitrile / 0.08 h / Darkness
3.1: water / d7-N,N-dimethylformamide / 2 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness
View Scheme
108-88-3

toluene

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With nitric acid; sodium dodecyl-sulfate In acetonitrile at 24.84℃; for 3h; Micellar solution; regioselective reaction;85%
27329-27-7

4-methyl-2-nitrobenzoic acid

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With copper(l) iodide; triethylamine In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 20h; Inert atmosphere; Schlenk technique;85%
With 1-methyl-pyrrolidin-2-one; quinoline; copper(I) oxide; 1,10-Phenanthroline at 100 - 175℃; for 0.5h; Inert atmosphere; Microwave irradiation;50%
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2 h / 20 °C / Darkness
2: tetrahydrofuran / Darkness
3: water / d7-N,N-dimethylformamide / 0.83 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness
View Scheme
625-95-6

3-Iodotoluene

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With copper; tetrabutylammonium nitrite; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 110℃; for 0.333333h; Inert atmosphere; Microwave irradiation;84%
With copper bronze; tetrabutylammonium nitrate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 100℃;69%
With potassium nitrite; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 130℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;67%
3748-99-0

N'-(3-nitrobenzylidene)-4-methylbenzenesulfonohydrazide

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With dichloro bis(1,4-diazabicyclo[2.2.2]octane)(BH4)Zr(IV); toluene-4-sulfonic acid In sulfolane; N,N-dimethyl-formamide at 110℃; for 7.2h;83%
594-27-4

tetramethylstannane

bis-(3-nitro-phenyl)-iodonium ; hydrogen sulfate

99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
With palladium diacetate In water at 60 - 70℃; for 4h;80%
palladium diacetate In water at 60℃; for 4h;80 % Chromat.
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Specification

The 3-Nitrotoluene with CAS registry number of 99-08-1 is also known as Benzene, 1-methyl-3-nitro-. The IUPAC name is 1-Methyl-3-nitrobenzene. It belongs to product categories of Industrial/Fine Chemicals; Aromatic Hydrocarbons (substituted) & Derivatives; Organics; Method 8330Alphabetic; NA - NIAnalytical Standards; 8000 Series Solidwaste Methods; Analytical Standards;AromaticsEnvironmental Standards; Chemical Class; Environmental Standards; ExplosivesEPA; N; Nitro CompoundsChromatography; Solid WasteMore...Close...; Volatiles/ Semivolatiles. Its EINECS registry number is 202-728-6. In addition, the formula is C7H7NO2 and the molecular weight is 137.14.

Physical properties about 3-Nitrotoluene are: (1)ACD/LogP: 2.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.41; (4)ACD/LogD (pH 7.4): 2.41; (5)#H bond acceptors: 3; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 1; (8)Polar Surface Area: 45.82Å2; (9)Index of Refraction: 1.553; (10)Molar Refractivity: 37.62 cm3; (11)Molar Volume: 117.5 cm3; (12)Polarizability: 14.91×10-24cm3; (13)Surface Tension: 42.6 dyne/cm; (14)Density: 1.166 g/cm3; (15)Flash Point: 101.7 °C; (16)Enthalpy of Vaporization: 44.95 kJ/mol; (17)Boiling Point: 231.9 °C at 760 mmHg; (18)Vapour Pressure: 0.0923 mmHg at 25 °C.

Preparation of 3-Nitrotoluene: it is prepared by reaction of 3-nitro-4-amino toluene. The product can be prepared by the following process and the yield is about 67%. What's more, this reaction can simultaneously recycle nitrotoluene.

C6C5CH3+HNO3→C7H7NO2+H2O

Uses of 3-Nitrotoluene: it is mainly used in organic synthesis, and also can be used as pesticide, dye, pharmaceuticals, color reagent, plastics, synthetic fiber and additives intermediate.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Besides, it's highly flammable and is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. It has danger of cumulative effects. During using it, wear suitable protective clothing and gloves. Avoid release to the environment. After contact with skin, wash immediately with plenty of water. 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: CC1=CC(=CC=C1)[N+](=O)[O-]
2. InChI: InChI=1S/C7H7NO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3
3. InChIKey: QZYHIOPPLUPUJF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 3600mg/kg (3600mg/kg)   Chemical Abstracts. Vol. 73, Pg. 91015e, 1970.
mouse LC50 inhalation 425mg/m3 (425mg/m3) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LIVER: FATTY LIVER DEGERATION

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 52, 1978.
mouse LD50 oral 330mg/kg (330mg/kg)   Chemical Abstracts. Vol. 73, Pg. 91015e, 1970.
rabbit LD50 oral 1750mg/kg (1750mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LIVER: FATTY LIVER DEGERATION

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 52, 1978.
rat LC50 inhalation 693mg/m3 (693mg/m3) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LIVER: FATTY LIVER DEGERATION

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 52, 1978.
rat LD50 oral 1072mg/kg (1072mg/kg)   National Technical Information Service. Vol. PB214-270,