Basic information
- Standard SMILES
O=Cc1ccc([N+](=O)[O-])cc1- InChIKey
BXRFQSNOROATLV-UHFFFAOYSA-N- Molecular formula
- C7H5NO3
- Average molar mass
- 151.12 g/mol
- Monoisotopic mass
- 151.02694302
Overview
4-nitrobenzaldehyde is a C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group. It is a member of benzaldehydes and a C-nitro compound.
Names & identifiers
- Preferred name
- 4-Nitrobenzaldehyde
- IUPAC
- 4-nitrobenzaldehyde
- English name
- 4-Nitrobenzaldehyde
- Molecular formula
- C7H5NO3
- Molecular weight
- 151.12
Names & synonyms
4-nitrobenzaldehyde555-16-8p-NitrobenzaldehydeBenzaldehyde, 4-nitro-p-FormylnitrobenzeneBenzaldehyde, p-nitro-DTXSID5022061para-nitrobenzaldehydeNX859P8MB0CHEBI:66926NSC-6103CCRIS-1675
Show more names
4-FORMYLNITROBENZENE4-NitrobenzaLobenzaldehyde-D5AKOS BBS-000032064-nitro-benzaldehydp-nitro-benzaldehydNITROBENZALDEHYDE 4-
DTXCID402061RefChem:100037209-084-54-Nitro-benzaldehydeMFCD00007346CCRIS 1675EINECS 209-084-5p-nitro benzaldehyde
Database identifiers
- CAS
555-16-8- PubChem CID
- 541
- DTXSID
DTXSID5022061- ChEMBL
CHEMBL164236- ChEBI
CHEBI:66926- UNII
- NX859P8MB0
- EC Number
- 209-084-5
- Nikkaji
- J1.618G
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 62.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 156
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials PropertiesChemical shift
Vapor Pressure0.00354 [mmHg]
Physical DescriptionLight yellow powder; [Sigma-Aldrich MSDS]
Ionization Efficiency
Positive
-0.09
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 103 · 103-106 °C(lit.)
- Boiling point
- 273.1 °C · 273.1°C (rough estimate)
- bulk density
- 400 kg/m3 · 400kg/m3
- Density
- 1 · 1,496 g/cm3
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2.34 g/l · 2.34g/l
- form
- Crystalline Powder
- color
- Yellow to brown
- Odor
- Odorless
- Water Solubility
- Soluble in water, ethanol, benzene, glacial acetic acid. Slightly soluble in ether.
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,6587
- BRN
- 386796 · 386796
- InChI
- 1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H
- InChIKey
- BXRFQSNOROATLV-UHFFFAOYSA-N
- SMILES
- [O-][N+](=O)c1ccc(C=O)cc1
- CAS DataBase Reference
- 555 · 555-16-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 859 P8MB0 · NX859P8MB0
- NIST Chemistry Reference
- 4 · Benzaldehyde, 4-nitro-(555-16-8)
- EPA Substance Registry System
- 4 · Benzaldehyde, 4-nitro- (555-16-8)
- UNSPSC Code
- 12352114 · 12352114
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317-H319
- Precautionary statements
- 280 · P280-P302+P352-P305+P351+P338
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36-43-52/53-36/37/38-68
- Safety Statements
- 26 · 26-36/37-61-24/25-36/37/39-36
- WGK Germany
- 2 · 2
- RTECS
- 7350000 · CU7350000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29130000 · 29130000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Sens. 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 4700 mg/kg LD50 dermal Rat 16000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (35.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 68 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzaldehyde, 4-nitro-
Status: Active Update: 25-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23721
Benzaldehyde, 4-nitro-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes somnolence, cyanosis, normocytic anemia, tetany, and dyspnea in oral lethal-dose studies of rats; [RTECS] An irritant; May cause skin sensitization, based on QSAR modeling; Prolonged or repeated exposure may cause narcosis; [Sigma-Aldrich MSDS] See Nitrobenzene and Benzaldehyde. See 3-Nitrobenzaldehyde.
Hazard Classes and CategoriesSkin Irrit. 2 (35.3%)
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- CU7350000
- hs_code
- 29130000
- Toxicity
- LD50 orally in Rabbit: 4700 mg/kg LD50 dermal Rat 16000 mg/kg
- risk_code
- 36-43-52/53-36/37/38-68
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37-61-24/25-36/37/39-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Sens. 1
- Precautionary statements
- P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzaldehyde, 4-nitro-: ACTIVE
Applications
Uses4-Nitrobenzaldehyde is a benzaldehyde with a nitro group in the para position. It is used as a reagent in decarboxylative aldol reactions that are catalyzed by lipases and proteases in organic co-solvent mixtures.
Uses4-Nitrobenzaldehyde was used in the preparation of homoallylic alcohols. It was also used to develop and evaluate a series of tripeptide organocatalysts.
Upstream & downstream products
Upstream raw materials
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Additional notes
DefinitionChEBI: 4-nitrobenzaldehyde is a C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group. It is a C-nitro compound and a member of benzaldehydes.
Related reactions
610 records
Linked notes
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