Basic information
- CAS
552-89-6- Standard SMILES
O=Cc1ccccc1[N+](=O)[O-]- InChIKey
CMWKITSNTDAEDT-UHFFFAOYSA-N- Molecular formula
- C7H5NO3
- Average molar mass
- 151.12 g/mol
- Monoisotopic mass
- 151.02694302
Overview
2-nitrobenzaldehyde is benzaldehyde substituted at the ortho-position with a nitro group. It is a member of benzaldehydes and a C-nitro compound.
Names & identifiers
- Preferred name
- 2-Nitrobenzaldehyde
- IUPAC
- 2-nitrobenzaldehyde
- English name
- 2-Nitrobenzaldehyde
- Molecular formula
- C7H5NO3
- Molecular weight
- 151.12
Names & synonyms
2-NITROBENZALDEHYDE552-89-6o-NitrobenzaldehydeBenzaldehyde, 2-nitro-Benzaldehyde, o-nitro-2-Nitro-benzaldehydeortho-nitrobenzaldehydeDTXSID002206048B18Q9B8ENSC-5713CHEBI:66927CCRIS-2322
Show more names
2-nitro-benzaldehyd2-NBA2-Nitrobenzenecarboxaldehyde2-NitobenzaldehydeNSC 5713AKOS 938642-NitrobenzaLAKOS BBS-00003153
DTXCID002060RefChem:88705209-025-3Nitrobenzaldehyde2-FORMYLNITROBENZENEnitro benzaldehydeMFCD000071321-FORMYL-2-NITROBENZENE
Database identifiers
- CAS
552-89-6- PubChem CID
- 11101
- DTXSID
DTXSID0022060- ChEMBL
CHEMBL166559- ChEBI
CHEBI:66927- UNII
- 48B18Q9B8E
- EC Number
- 209-025-3
- Nikkaji
- J1.615B
Properties
Computed structural properties
- XLogP
- 1.7
- 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
- 164
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP1.74
Physical DescriptionPartially soluble in water (2.32 g/L at 25 deg C); [ChemIDplus] Yellow crystalline powder; [MSDSonline]
Ionization Efficiency
Positive
0.78
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 42 · 42-44 °C(lit.)
- Boiling point
- 153 °C23 · 153 °C23 mm Hg(lit.)
- Density
- 1 · 1,284 g/cm3
- bulk density
- 350 kg/m3 · 350kg/m3
- vapor density
- 5.2 · 5.2 (vs air)
- refractive index
- 1.58 · 1.5800 (estimate)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Crystalline Powder, Needles and/or Chunks
- color
- Yellow
- Water Solubility
- Insoluble in water.
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,6586
- BRN
- 742624 · 742624
- InChI
- 1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H
- InChIKey
- CMWKITSNTDAEDT-UHFFFAOYSA-N
- SMILES
- [O-][N+](=O)c1ccccc1C=O
- LogP
- 1.74 at · 1.74 at 25℃
- CAS DataBase Reference
- 552 · 552-89-6(CAS DataBase Reference)
- REACH Annex XVII Substances List
- o-Nitrobenzaldehyde (552-89-6)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 48 B18Q9B8E · 48B18Q9B8E
- NIST Chemistry Reference
- 2 · Benzaldehyde, 2-nitro-(552-89-6)
- EPA Substance Registry System
- 2 · Benzaldehyde, 2-nitro- (552-89-6)
- UNSPSC Code
- 12352114 · 12352114
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335-H412
- Precautionary statements
- 273 · P273-P301+P312+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-68
- Safety Statements
- 26 · 26-24/25-36/37/39-36
- WGK Germany
- 2 · 2
- RTECS
- 7300000 · CU7300000
- F
- 8 · 8
- Autoignition Temperature
- 200 °C · 200 °C (Lit.)
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29130000 · 29130000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 120 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzaldehyde, 2-nitro-
Status: Active Update: 06-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11680
Restricted substance: o-Nitrobenzaldehyde
Benzaldehyde, 2-nitro-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzaldehyde, 2-nitro-: Human health tier I assessment
Hazards SummaryAn irritant; [MSDSonline] See 3-Nitrobenzaldehyde.
Hazard Classes and CategoriesAcute Tox. 4 (97.5%)
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- CU7300000
- hs_code
- 29130000
- risk_code
- 22-36/37/38-68
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-24/25-36/37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335-H412
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Autoignition Temperature
- 200 °C (Lit.)
- Precautionary statements
- P273-P301+P312+P330-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzaldehyde, 2-nitro-: ACTIVE
Applications
Description2-Nitrobenzaldehyde (2-NBA) is a multifunctional compound used in dyes, pharmaceuticals, food, and organic synthesis. Due to its distinctive yellow crystalline appearance, 2-NBA is used as an intermediate in the synthesis of indigo dyes. It is also used in the synthesis of 2-Nitrobenzyl-chitosan and nifedipine. Furthermore, 2-NBA can be used as a preservative in meat products, for the preservation of meat and food (preventing light damage), and has applications in the packaging industry.
Uses2-Nitrobenzaldehyde is a benzaldhyde with a nitro group substituted in the ortho position. 2-Nitrobenzaldehyde is used in the preparation of dyes and colorants such as Indigo carmine. 2-Nitrobenzaldehyde gas been shown to be a useful photoremovable protecting group as well as in the preparation of more effective ones such as o-Nitrophenylethylene glycol.
General DescriptionThe 2-Nitrobenzyl group of 2-nitrobenzaldehyde is photolabile that can be cleaved when exposed to UV-light.
Preparation methods
Preparation2-Nitrobenzaldehyde is synthesized from 2-Nitrotoluene by nitration and oxidation.Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 2-nitrobenzaldehyde is benzaldehyde substituted at the ortho-position with a nitro group. It is a C-nitro compound and a member of benzaldehydes.
Related reactions
288 records
Compound notes
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