Basic information
- CAS
105-07-7- Standard SMILES
N#Cc1ccc(C=O)cc1- InChIKey
WZWIQYMTQZCSKI-UHFFFAOYSA-N- Molecular formula
- C8H5NO
- Average molar mass
- 131.13 g/mol
- Monoisotopic mass
- 131.03711378
Names & identifiers
- Preferred name
- 4-Cyanobenzaldehyde
- IUPAC
- 4-formylbenzonitrile
- English name
- 4-Cyanobenzaldehyde
- Molecular formula
- C8H5NO
- Molecular weight
- 131.13
Names & synonyms
Show more names
Database identifiers
- CAS
105-07-7- PubChem CID
- 66042
- DTXSID
DTXSID6059312- ChEMBL
CHEMBL1922276- ChEBI
CHEBI:156308- UNII
- DWH62Y9TCA
- EC Number
- 203-267-3
- Nikkaji
- J22.132E
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 40.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 159
Physicochemical properties
- Melting point
- 100102 °C · 100102°C
- Boiling point
- 133 °C12mm · 133°C12mm Hg
- Density
- 1.1971 · 1.1971 (rough estimate)
- refractive index
- 1.47 · 1.4700 (estimate)
- Flash point
- 133 °C/12mm · 133°C/12mm
- storage temp.
- 30 °C · Store below +30°C.
- form
- Crystalline Powder
- color
- White to slightly beige
- Water Solubility
- It is soluble in water, ethanol, ether and chloroform.
- Sensitive
- Air Sensitive
- BRN
- 606473 · 606473
- InChI
- 1S/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H
- InChIKey
- WZWIQYMTQZCSKI-UHFFFAOYSA-N
- SMILES
- O=Cc1ccc(cc1)C#N
- CAS DataBase Reference
- 105 · 105-07-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 62 Y9TCA · DWH62Y9TCA
- NIST Chemistry Reference
- 4 · Benzonitrile, 4-formyl-(105-07-7)
- EPA Substance Registry System
- 4 · Benzonitrile, 4-formyl- (105-07-7)
- UNSPSC Code
- 12352117 · 12352117
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332
- Precautionary statements
- 261 · P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 36 · 36/37-36-26
- RIDADR
- 3439 · 3439
- WGK Germany
- 3 · 3
- RTECS
- 5250000 · CU5250000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29269095 · 29269095
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CU5250000
- ridadr
- 3439
- hs_code
- 29269095
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 36/37-36-26
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H302+H312+H332
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
Chemistry & industry
Applications
Uses4-Cyanobenzaldehyde, is used as an intermediate for organic synthesis.It is also used as an intermediate in the pharmaceutical and research department.
Uses4-Formylbenzonitrile can be used in the synthesis of various boron-dipyrromethenes (BODIPY), porphyrins, corroles and other related macrocycles.
Uses4-Cyanobenzaldehyde is used as a reagent in the synthesis of hydrazone based inhibitors of adipose-triglyceride lipase (ATGL). 4-Cyanobenzaldehyde is also used as a reagent in the synthesis of BAZ2-ICR which is a chemical probe targeting the bromo domains of BAZ2A and BAZ2B.
Preparation methods
PreparationSynthesis steps of 4-cyanobenzaldehyde: (1) Take 20 mL of p-dimethylbenzene and place it in a reaction vessel. Heat the reaction vessel to 130-135℃ and add the solvent N,N-dimethylformamide DMF, catalyst and co-catalyst in sequence. The amount of N,N-dimethylformamide DMF added is 20-25 mL, and the amount of catalyst and co-catalyst added is 2.5-3.0 g and 10-15 g, respectively. Control the oxygen flow rate to 900 mL/min and the hydrogen flow rate to 100 mL/min. React for 4-5 h; (2) Cool the above reaction solution to room temperature. The obtained transparent colorless crystals are p-methylbenzonitrile. Wash the obtained crystals 2-3 times with DMF and then filter out the impurities. (2) Remove the DMF solvent to obtain p-methylbenzonitrile with a purity higher than 90%; (3) Place the p-methylbenzonitrile synthesized in step (2) above into a reaction vessel, heat the reaction vessel to 110-115℃, and add the solvent N,N-dimethylformamide DMF, catalyst and co-catalyst in sequence. The amount of N,N-dimethylformamide DMF added is 10-15mL, and the amount of catalyst and co-catalyst added is 1.0-1.5g and 8.0-9.0g, respectively. Control the oxygen flow rate to be 900mL/min and the hydrogen flow rate to be 100mL/min. React for 2-3h, and the resulting white crystalline powder is 4-cyanobenzaldehyde.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: 4-cyanobenzaldehyde is a member of benzaldehydes.
Related reactions
Compound notes
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