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4-Chloro-2-nitrophenol

HCID 6980
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Basic information

CAS
89-64-5
Standard SMILES
O=[N+]([O-])c1cc(Cl)ccc1O
InChIKey
NWSIFTLPLKCTSX-UHFFFAOYSA-N
Molecular formula
C6H4ClNO3
Average molar mass
173.55 g/mol
Monoisotopic mass
172.9879707

Names & identifiers

Preferred name
4-Chloro-2-nitrophenol
IUPAC
4-chloro-2-nitrophenol
English name
4-Chloro-2-nitrophenol
Molecular formula
C6H4ClNO3
Molecular weight
173.55

Names & synonyms

4-CHLORO-2-NITROPHENOL89-64-52-Nitro-4-chlorophenolPhenol, 4-chloro-2-nitro-438LQ62WNHNSC-520345DTXSID4058996RefChem:98397DTXCID2048664201-927-54-chloro-6-nitrophenol4-chloro-2-nitro-phenol
Show more names
AKOS BBS-000046674-CHLORO-2-NITROPHENo-nitro-p-chorophenol4-chloro-2-nitro-phenoO-NITRO-P-CHLOROPHENOL4--chloro-o-nitrophenolPhenol,4-chloro-2-nitro-4-chloro-2-nitrophenolate
5-chloro-2-hydroxynitrobenzeneMFCD00007113P-CHLORO-O-NITROPHENOLNSC520345SCHEMBL305611SCHEMBL2149474SCHEMBL11332607SBB041094

Database identifiers

CAS
89-64-5
PubChem CID
6980
DTXSID
DTXSID4058996
UNII
438LQ62WNH
EC Number
201-927-5
Nikkaji
J60.201I

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
66.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
11
Formal charge
0
Complexity
158

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitrophenols
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP2.48
Vapor Pressure0.00778 [mmHg]
Physical DescriptionYellow crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
85 · 85-87 °C(lit.)
Boiling point
242.5 · 242.5±20.0 °C(Predicted)
Density
1.4914 · 1.4914 (rough estimate)
refractive index
1.581 · 1.5810 (estimate)
solubility
0.5 g/5mL, · dioxane: soluble0.5g/5mL, clear, faintly yellow to yellow
form
powder to crystal
pka
1 · pK1: 6.48 (25°C)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.6% (2 of 124) of reports.

Warning

H315 (98.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 124 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Phenol, 4-chloro-2-nitro-

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

REACH registered substance: 4-chloro-2-nitrophenol (EC: 201-927-5)

Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See 2-Nitrophenol.
Hazard Classes and CategoriesSkin Irrit. 2 (98.4%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

12 [mg/m3]

130 [mg/m3]

790 [mg/m3]

Safety data

wgk
3
tsca
TSCA listed
ridadr
2811
hs_code

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPhenol, 4-chloro-2-nitro-: ACTIVE
Applications · 2 items

Description4-Chloro-2-nitrophenol, is a kind of chloronitrophenols (CNPs), being widely used in the synthesis of dyes, drugs and pesticides. Furthermore, it can be used to produce 2-Amino-4-chloro-phenol.It has become a major group of environmental pollutants. 4-Chloro-2-nitrophenol has been detected in various industrial effluents. Therefore, it has also been used as a model compound for evaluation of biodegradation strategy using microbes.

UsesReduction of 4-Chloro-2-nitrophenol gives 2-amino-4- chlorophenol [95-85-2], and chlorination yields 2,4-dichloro-6-nitrophenol [609-89-2], which is reduced to 2-amino-4,6-dichlorophenol [527-62-8]. These substituted aminophenols are members of a large class of diazo components used for hydroxyazo dyes, which are important for wool and polyamide when converted to their chromium complexes. For the amine derived from the methyl ether of 4-Chloro-2-nitrophenol, 4- chloro-o-anisidine [93-50-5], the preferred route is methoxylation of 2,5-dichloronitrobenzene followed by reduction. 2-amino-4-chlorophenol reacts with phosgene to give 5- chlorobenzoxolinone which nitrates to the 6-nitro compound; the latter undergoes alkaline hydrolysis to 2-amino-4- chloro-5-nitrophenol.

Upstream & downstream products

Upstream raw materials

2,4-Dichloro-6-nitrophenolphenoxy radical1-nitro-4-phenoxysulfonyl-benzene2-Chloro-6-nitrophenol4-Chlorophenol2-Nitrophenol

Related reactions

34 records
New reaction record
HRID 11626 reaction equation
HRID 11626As reactantuspto-grants-2006_08
HRID 11632 reaction equation
HRID 11632As reactantuspto-grants-2006_08
HRID 170312 reaction equation
HRID 170312As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 187562 reaction equation
HRID 187562As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 211208 reaction equation
HRID 211208As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 261042 reaction equation
HRID 261042As reactantuspto-grants-1979_08
HRID 480186 reaction equation
HRID 480186As reactantuspto-grants-2003_11
HRID 663457 reaction equation
HRID 663457As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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color
Light yellow to Yellow to Orange
BRN
2048031 · 2048031
Henry's Law Constant
7.8 · 7.8×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
CAS DataBase Reference
89 · 89-64-5(CAS DataBase Reference)
FDA UNII
438 LQ62WNH · 438LQ62WNH
EPA Substance Registry System
4 · 4-Chloro-2-nitrophenol (89-64-5)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-20/21/22
Safety Statements
26 · 26-36-36/37/39
RIDADR
2811 · 2811
WGK Germany
3 · 3
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29089990 · 29089990
REACH Registrations
Active
29089990
risk_code
36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-36-36/37/39
hazard_class
6.1
packing_group
III
Hazard statements
H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338

Downstream products

Chlorzoxazone2-Amino-4-chlorophenolPiperidine, 1-benzoyl-3-methyl-2-Chloro-1,4-benzoquinone4-Chloro-2-nitroanisole2,5-DichlorobenzooxazoleMethanol4-Bromo-2-nitrophenol