N-Hydroxyphthalimide

HCID 10665
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Basic information

CAS
524-38-9
Standard SMILES
O=C1c2ccccc2C(=O)N1O
InChIKey
CFMZSMGAMPBRBE-UHFFFAOYSA-N
Molecular formula
C8H5NO3
Average molar mass
163.13 g/mol
Monoisotopic mass
163.02694302

Overview

causes contact dermititis

Names & identifiers

Preferred name
N-Hydroxyphthalimide
IUPAC
2-hydroxyisoindole-1,3-dione
English name
N-Hydroxyphthalimide
Molecular formula
C8H5NO3
Molecular weight
163.13

Names & synonyms

N-HYDROXYPHTHALIMIDE524-38-92-Hydroxyphthalimide1H-Isoindole-1,3(2H)-dione, 2-hydroxy-Phthalimide, N-hydroxy-BXI99M81X0NSC-770F 802DTXSID7060170RefChem:830142DTXCID1041188208-358-1
Show more names
nhpihydroxyphthalimideHOPHTN-Hydrophthalimide
2-hydroxyisoindoline-1,3-dione2-Hydroxy-1H-isoindole-1,3(2H)-dione2-hydroxyisoindole-1,3-dioneMFCD000058912-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione2-oxidanylisoindole-1,3-dioneCHEMBL2760572-hydroxy-isoindole-1,3-dione

Database identifiers

CAS
524-38-9
PubChem CID
10665
DTXSID
DTXSID7060170
ChEMBL
CHEMBL276057
UNII
BXI99M81X0
EC Number
208-358-1
Nikkaji
J26.847J

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
57.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Nitrogen Rings
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physical DescriptionYellowish or colorless solid; [Merck Index] White or off-white crystalline powder; [Alfa Aesar MSDS]
Ionization Efficiency · 6 items

Negative

-0.43

10.5

Agilent XCT

Electrospray ionization

ammonia (10nM)

Physicochemical properties

Melting point
233 °C · 233 °C (dec.) (lit.)
Boiling point
290.19 °C · 290.19°C (rough estimate)
Density
1.64 g/cm3 · 1.64 g/cm3
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.551 · 1.5510 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): 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 152 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 1H-Isoindole-1,3(2H)-dione, 2-hydroxy-

Status: Cease Manufacture Update: 24-03-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19261

1H-Isoindole-1,3(2H)-dione, 2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntravenous LD50 (mouse) = 178 mg/kg; [RTECS] Causes contact dermatitis. [ChemIDplus] A skin and strong eye irritant; [Alfa Aesar MSDS] See N-Aminophthalimide.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
TI5200000
hs_code
29251995
risk_code
36/37/38

Chemistry & industry

Uses & manufacturing

UsesUsed as a catalyst for oxidation reactions; [Merck Index]
General Manufacturing Information1H-Isoindole-1,3(2H)-dione, 2-hydroxy-: ACTIVE
Applications · 3 items

UsesCatalyst for oxidation reactions.

UsesAerobic oxidation of various alcohols has been accomplished by using a new catalytic system, N-hydroxyphthalimide (NHPI) combined with Co (acac). A practical catalytic method to convert alkylbenzenes into the corresponding carboxylic acids under atmospheric dioxygen at ambient temperature using a combined catalytic system consisting of N-hydroxyphthalimide (NHPI) and Co (OAc) 2 was developed. Novel catalysis by N-hydroxyphthalimide in the oxidation of organic substrates by molecular oxygen was described. Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Purely organic and catalytic systems of anthraquinones and N-hydroxyphthalimide efficiently promote oxygenation of hydrocarbons with dioxygen under mild conditions. Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with was transition metal salts.

UsesN-Hydroxyphthalimide，additives in to DCC method of peptide synthesis used to improve yield of optically pure product.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Related reactions

3,754 records
New reaction record

Compound notes

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