Basic information
- Standard SMILES
Oc1cc2ccccc2cc1O- InChIKey
JRNGUTKWMSBIBF-UHFFFAOYSA-N- Molecular formula
- C10H8O2
- Average molar mass
- 160.17 g/mol
- Monoisotopic mass
- 160.0524295
Overview
Naphthalene-2,3-diol is a naphthalenediol.
Names & identifiers
- Preferred name
- 2,3-Dihydroxynaphthalene
- IUPAC
- naphthalene-2,3-diol
- English name
- 2,3-Dihydroxynaphthalene
- Molecular formula
- C10H8O2
- Molecular weight
- 160.17
Names & synonyms
2,3-DihydroxynaphthaleneNaphthalene-2,3-diol92-44-42,3-NAPHTHALENEDIOLDTXSID2043903O9U131030ZCHEBI:38135NSC-8707DTXCID0023903RefChem:81773202-156-72,3-Dihydroxynapthalene
Show more names
2,3-Dihydroxy2,3-DIHYDROXYNAPHTHALENE, SUBL.Naphthalin-2,3-diolDihydroxynaphthaleneNaphthalenediol-(2,3)3-Dihydroxynaphthalene2,3-Dihydroxyphthalene
2,3-Dihydroxy naphthalene2,3-DihydroxynaphthleneNSC 8707MFCD00004073EINECS 202-156-73-hydroxy-2-naphtholBDBM362902,3-DIHYDROXY-NAPHTHALENE
Database identifiers
- CAS
92-44-4- PubChem CID
- 7091
- DTXSID
DTXSID2043903- ChEMBL
CHEMBL205007- ChEBI
CHEBI:38135- UNII
- O9U131030Z
- EC Number
- 202-156-7
- Nikkaji
- J30.353D
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 140
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Naphthols
Cosmetics
Cosmetic ingredients (2,3-Naphthalenediol) -> CIR (Cosmetic Ingredient Review)
Hair dyeing
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP2.24
Vapor Pressure0.00000715 [mmHg]
Physical DescriptionWhite powder; [Alfa Aesar MSDS]
Collision Cross Section
132.44 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
131.3 Ų [M-H]-
Physicochemical properties
- Melting point
- 161 · 161-165 °C (lit.) 162-164 °C
- Boiling point
- 246.06 °C · 246.06°C (rough estimate)
- Density
- 1.0924 · 1.0924 (rough estimate)
- bulk density
- 500 kg/m3 · 500kg/m3
- vapor pressure
- 0.8 hPa · 0.8 hPa (149 °C)
- refractive index
- 1.5178 · 1.5178 (estimate)
- Flash point
- 175 °C · 175 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 4 g/l · 4g/l
- form
- Powder
- pka
- 9.1 · 9.10±0.40(Predicted)
- color
- White to pinkish to beige-grayish
- PH
- 6 · 6 (1g/l, H2O, 20℃)
- Water Solubility
- slightly soluble
- BRN
- 742375 · 742375
- Henry's Law Constant
- 2 · 2.0×105 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- Cosmetics Ingredients Functions
- HAIR DYEING
- Cosmetic Ingredient Review (CIR)
- 2 · 2,3-Dihydroxynaphthalene (92-44-4)
- InChI
- 1S/C10H8O2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6,11-12H
- InChIKey
- JRNGUTKWMSBIBF-UHFFFAOYSA-N
- SMILES
- Oc1cc2ccccc2cc1O
- CAS DataBase Reference
- 92 · 92-44-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-4
- FDA UNII
- 9 U131030Z · O9U131030Z
- NIST Chemistry Reference
- 2 · 2,3-Naphthalenediol(92-44-4)
- EPA Substance Registry System
- 2 · 2,3-Naphthalenediol (92-44-4)
- UNSPSC Code
- 12352104 · 12352104
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H318
- Precautionary statements
- 264 · P264-P270-P280-P301+P312-P305+P351+P338-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-37/39
- WGK Germany
- 3 · 3
- RTECS
- 4750000 · QJ4750000
- F
- 10 · 10-23
- Autoignition Temperature
- 330 °C · >330 °C
- TSCA
- TSCA listed
- HS Code
- 29072900 · 29072900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 970 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (16%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2,3-Naphthalenediol
2,3-Naphthalenediol: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Chemicals with limited data availability that may be used in hair dyes overseas: Human health tier II assessment
Hazards SummaryIntravenous LD50 (mouse) = 56 mg/kg; [RTECS] An irritant that may cause serious eye injury; Harmful by ingestion; [Alfa Aesar MSDS] See 1-Napththol and 2-Naphthol. See 2,7-Naphthalenediol.
Hazard Classes and CategoriesAcute Tox. 4 (16%)
Toxicology
Toxicity Summary
The CIR Expert Panel concludes that the available data are insufficient to support the safety of 2,3-Naphthalenediol as used in cosmetics.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
Safety data
- F
- 10-23
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- QJ4750000
- hs_code
- 29072900
- Toxicity
- LD50 orally in Rabbit: 970 mg/kg
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H318
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1
- Autoignition Temperature
- >330 °C
- Precautionary statements
- P264-P270-P280-P301+P312-P305+P351+P338-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites2,3-Dihydroxynaphthalene has known human metabolites that include 3-Methoxy-2-naphthol.
Uses & manufacturing
UsesCIR ingredient: 2,3-Naphthalenediol
Use ClassificationCosmetics -> Hair dyeing
General Manufacturing Information2,3-Naphthalenediol: ACTIVE
Applications
Uses2,3-Naphthalenediol is used in cosmetics asa component of oxidative hair dye. It is usedat a concentration of
Uses2,3-Dihydroxynaphthalene is used in making dyes, pigments, fluorescent whiteners, tanning agents, antioxidants, and antiseptics.
Uses2,3-Dihydroxynaphthalene may be used in the following studies:Construction of dinaphtho[2,1-b;2′,3′-d]furan-6-ol, via dehydration reaction in the presence of strong acid.As fused ring catecholate type ligand for the surface modification of nanocrystalline TiO2 particles.As adsorptive and competing ligand during the chemical speciation of iron in seawater by cathodic stripping voltammetry.Synthesis of cyclotriphosphazene derivatives, used as non-halogen flame retardants
General Description2,3-Dihydroxynaphthalene is a polyhydroxy phenol. It is an aromatic dihydroxy compound having hydroxyl groups at ortho positions. Its reaction with molybdenum(VI) complexes has been reported. The asymmetric oxidative coupling polymerization of 2,3-dihydroxynaphthalene using the Cu(I)-bisoxazoline complex as catalyst has been reported to afford poly(2,3-dihydroxy-1,4-naphthylene), having a continuous 1,1′-bi-2-naphthol main chain structure. The nitrodisplacement reaction between nitrophthalodinitriles and 2,3-dihydroxynaphthalene has been investigated.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Naphthalene-2,3-diol is a naphthalenediol.
Related reactions
36 records
Linked notes
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