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89-59-8

Basic Information
CAS No.: 89-59-8
Name: 4-Chloro-2-nitrotoluene
Article Data: 31
Molecular Structure:
Molecular Structure of 89-59-8 (4-Chloro-2-nitrotoluene)
Formula: C7H6ClNO2
Molecular Weight: 171.583
Synonyms: 4-Chloro-1-methyl-2-nitro-benzene;
EINECS: 201-921-2
Density: 1.324 g/cm3
Melting Point: 35 °C
Boiling Point: 238.5 °C at 760 mmHg
Flash Point: 98.1 °C
Solubility: 109 mg/L (20 °C) in water
Appearance: clear brown liquid after melting
Hazard Symbols: IrritantXi,HarmfulXn,DangerousN
Risk Codes: 36/37/38-20/21/22-52/53
Safety: 26-36/37/39-61
Transport Information: UN 3457 6.1/PG 3
PSA: 45.82000
LogP: 3.07980
Synthetic route
10565-16-9

(4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester

89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With dimethyl sulfoxide; sodium chloride at 160 - 170℃; for 24h; Decarboxylation; Krapcho's reaction;55%
106-43-4

para-chlorotoluene

A

89-59-8

4-chloro-2-nitrotoluene

B

89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
With oxygen; Nitrogen dioxide; iron(III)-acetylacetonate In 1,2-dichloro-ethane at 0℃; for 12h;A 54%
B 39%
With nitric acid; urea In acetic anhydride at 0 - 5℃; for 3h;A 9.1%
B 12%
With nitric acid; urea In acetic anhydride at 0 - 5℃; for 3h;A 9.1%
B 12%
106-43-4

para-chlorotoluene

89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at 50 - 55℃; for 2h;49.2%
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid das mit Aether isolierte Reaktionsprodukt unterwirft man der fraktionierten Destillation, wobei 4-Chlor-2-nitro-toluol bei 240-245grad uebergeht;
Multi-step reaction with 2 steps
1: 2 g / nitric acid, acetic anhydride, trifluoroacetic anhydride
2: 94.3 percent Chromat. / 92.4percent sulphuric acid, hydrazinium sulphate / H2O / 0.03 h / 25 °C
View Scheme
106-43-4

para-chlorotoluene

A

119-33-5

4-methyl-2-nitrophenol

B

89-59-8

4-chloro-2-nitrotoluene

C

89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h;A 9.3%
B 39.1%
C 31%
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h; Title compound not separated from byproducts;A 9.3 % Chromat.
B 39.1 % Chromat.
C 31.0 % Chromat.
88-72-2

1-methyl-2-nitrobenzene

89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With oxone; potassium chloride In acetonitrile at 20℃; for 24h;5%
88-72-2

1-methyl-2-nitrobenzene

A

83-42-1

6-chloro-2-nitrotoluene

B

89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
With antimonypentachloride durch Chlorierung;
With chlorine; iron at 30℃;
With antimonypentachloride; chlorine
With chlorine; iron
With iodine; iron at 50 - 60℃; beim Chlorieren;
75508-74-6

5-chloro-2-methyl-2-nitrocyclohexa-3,5-dienyl acetate

A

89-59-8

4-chloro-2-nitrotoluene

B

89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
With hydrazin sulfate; sulfuric acid In water at 25℃; for 0.0333333h; Title compound not separated from byproducts;A 94.3 % Chromat.
B 3.5 % Chromat.

3-nitro-4-methylphenylammonium hydrogensulfate

89-59-8

4-chloro-2-nitrotoluene

Conditions
ConditionsYield
(i) aq. HCl, NaNO2, (ii) CuCl, aq. HCl; Multistep reaction;
106-43-4

para-chlorotoluene

7664-93-9

sulfuric acid

A

89-59-8

4-chloro-2-nitrotoluene

B

89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
Product distribution; Nitrierung;
106-43-4

para-chlorotoluene

7697-37-2

nitric acid

A

89-59-8

4-chloro-2-nitrotoluene

B

89-60-1

1-chloro-4-methyl-2-nitro-benzene

Conditions
ConditionsYield
at -15℃; Quantum yield; sowie im Temperaturbereich von 0grad bis 50grad;
at 0℃; Product distribution;
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Specification

The 4-Chloro-2-nitrotoluene, with the CAS registry number 89-59-8, is also known as Benzene, 4-Chloro-1-methyl-2-nitro-. It belongs to the product categories of Aromatic Hydrocarbons (substituted) & Derivatives; Nitrogen Compounds; Organic Building Blocks; Alpha Sort; Analytical Standards; AromaticsVolatiles/ Semivolatiles; C; CAlphabetic; CHChemical Class; Chemical Class; ChloroAnalytical Standards; Halogenated; Nitro Compounds. Its EINECS registry number is 201-921-2. This chemical's molecular formula is C7H6ClNO2 and molecular weight is 171.58. What's more, both its IUPAC name and systematic name are the same which is called 4-Chloro-1-methyl-2-nitrobenzene. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 4-Chloro-2-nitrotoluene are: (1)ACD/LogP: 2.918; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.92; (4)ACD/LogD (pH 7.4): 2.92; (5)ACD/BCF (pH 5.5): 97.27; (6)ACD/BCF (pH 7.4): 97.27; (7)ACD/KOC (pH 5.5): 921.73; (8)ACD/KOC (pH 7.4): 921.73; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 45.82 Å2; (13)Index of Refraction: 1.57; (14)Molar Refractivity: 42.518 cm3; (15)Molar Volume: 129.501 cm3; (16)Surface Tension: 45.46 dyne/cm; (17)Density: 1.325 g/cm3; (18)Flash Point: 98.053 °C; (19)Enthalpy of Vaporization: 45.61 kJ/mol; (20)Boiling Point: 238.518 °C at 760 mmHg; (21)Vapour Pressure: 0.065 mmHg at 25 °C.

Preparation of 4-Chloro-2-nitrotoluene: this chemical can be prepared by (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester. This reaction needs reagents NaCl and DMSO at temperature of 160-170 °C. The reaction time is 24 hours. The yield is 55 %.

4-Chloro-2-nitrotoluene can be prepared by (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester.

Uses of 4-Chloro-2-nitrotoluene: (1) it is used as dye intermediateand and organic Intermediate; (2) it is used to produce other chemicals. For example, it can react with 4-Dimethylamino-benzaldehyde to get {4-[2-(4-Chloro-2-nitro-phenyl)-vinyl]-phenyl}-dimethyl-amine. The reaction occurs with reagents benzyltriethylammonium chloride, 50 percent aq. NaOH. The yield is 95 %.

4-Chloro-2-nitrotoluene can react with 4-Dimethylamino-benzaldehyde to get {4-[2-(4-Chloro-2-nitro-phenyl)-vinyl]-phenyl}-dimethyl-amine.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and may cause inflammation to the skin or other mucous membranes. It may may present an immediate or delayed danger to one or more components of the environment. This chemical is inflammation to the skin, eyes and respiratory system. In addition, it may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. You must avoid releasing to the environment. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1cc([N+]([O-])=O)c(cc1)C
(2) InChI: InChI=1S/C7H6ClNO2/c1-5-2-3-6(8)4-7(5)9(10)11/h2-4H,1H3
(3) InChIKey: SQFLFRQWPBEDHM-UHFFFAOYSA-N