Basic information
- Standard SMILES
O=[N+]([O-])c1cc(Cl)ccc1O- InChIKey
NWSIFTLPLKCTSX-UHFFFAOYSA-N- Molecular formula
- C6H4ClNO3
- Average molar mass
- 173.55 g/mol
- Monoisotopic mass
- 172.98797067
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
Show more names
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
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)
- 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
Safety & regulation
GHS classification
GHS Classification
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
Chemical: Phenol, 4-chloro-2-nitro-
TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.
Status: Active Update: 31-07-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20336
Safety & protection
Protective Action Criteria (PAC)
12 [mg/m3]
130 [mg/m3]
790 [mg/m3]
Safety data
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 2811
- hs_code
- 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
Chemistry & industry
Uses & manufacturing
Applications
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
Downstream products
Suppliers20 total
Related reactions
Linked notes
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