ChemicalBook--->CAS DataBase List--->3272-08-0

3272-08-0

3272-08-0 Structure

3272-08-0 Structure
IdentificationMore
[Name]

4-Hydroxy-3-nitrobenzonitrile
[CAS]

3272-08-0
[Synonyms]

2-NITRO-4-CYANOPHENOL
4-CYANO-2-NITROPHENOL
4-HYDROXY-3-NITROBENZONITRILE
4-HYDROXY-3-NITROBENZONITRILE/2-NITRO-4-CYANOPHENOL
4-HYDROXY-3-NITROBENZONITRILE 97%
4-BROMO-2,6-DIETHOXY-1-NITROBENZENE
Benzonitrile, 4-hydroxy-3-nitro-
3-Nitro-4-hydroxybenzonitrile
[EINECS(EC#)]

221-899-8
[Molecular Formula]

C7H4N2O3
[MDL Number]

MFCD00070775
[Molecular Weight]

164.12
[MOL File]

3272-08-0.mol
Chemical PropertiesBack Directory
[Appearance]

yellow powder
[Melting point ]

146-148 °C (lit.)
[Boiling point ]

291.56°C (rough estimate)
[density ]

1.5018 (rough estimate)
[refractive index ]

1.5300 (estimate)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

4.66±0.14(Predicted)
[InChI]

InChI=1S/C7H4N2O3/c8-4-5-1-2-7(10)6(3-5)9(11)12/h1-3,10H
[InChIKey]

INBLGVOPOSGVTA-UHFFFAOYSA-N
[SMILES]

C(#N)C1=CC=C(O)C([N+]([O-])=O)=C1
[CAS DataBase Reference]

3272-08-0(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[WGK Germany ]

3
[HS Code ]

29269090
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

4-Cyano-2-nitrophenol(3272-08-0).msds
Hazard InformationBack Directory
[Chemical Properties]

yellow powder
[Uses]

4-Hydroxy-3-nitrobenzonitrile may be used in the synthesis of:
  • 3-azido-4-methoxybenzonitrile
  • 4-methoxy-3-nitrobenzonitrile
  • ethyl [2,2-dimethyl-6-(Δ2-thiazolin-2-yl)-4H-l,4-benzoxazin-3-one-4-yl]butyrate
[General Description]

4-Hydroxy-3-nitrobenzonitrile is one of the main photoproduct formed during hotolytic destruction of herbicide bromoxynil.
[Synthesis]

4-Hydroxy-3-nitrobenzaldehyde

3011-34-5

4-Hydroxy-3-nitrobenzonitrile

3272-08-0

General procedure for the synthesis of 4-hydroxy-3-nitrobenzonitrile from 4-hydroxy-3-nitrobenzaldehyde: Aromatic aldehyde 1 (0.500 mmol, 1.0 eq.) and trimethylsilyl azide (TMSN3; 115 mg, 1.00 mmol, 2.0 eq.) were dissolved in a pre-mixed solvent mixture of hexafluoroisopropanol (HFIP) and acetonitrile (ACN) (2.0 mL, 1:1 volume ratio) in two dram vials, which was carried out under nitrogen protection. Subsequently, trifluoromethanesulfonic acid (TfOH; 17.7 μL, 0.200 mmol, 0.40 eq.) was added to the reaction system, and exothermic and rapid foaming phenomena due to gas production were immediately observed. The vial was quickly capped and the reaction mixture was stirred at room temperature for 20 to 75 min. Upon completion of the reaction, the reaction mixture was concentrated under a stream of nitrogen. The residue obtained was suspended in a solvent mixture of dichloromethane (CH2Cl2) and hexane and this suspension was upsampled into a cartridge containing 5 g silica gel. Purification was carried out by normal-phase silica gel fast column chromatography using a CombiFlash purification system, and suitable fractions were collected and concentrated to give the target product, aromatic nitrile 2.

[References]

[1] Journal of Organic Chemistry, 2012, vol. 77, # 12, p. 5364 - 5370
[2] Molecules, 2016, vol. 21, # 1,
[3] Patent: US5614520, 1997, A
Spectrum DetailBack Directory
[Spectrum Detail]

4-Hydroxy-3-nitrobenzonitrile(3272-08-0)1HNMR
4-Hydroxy-3-nitrobenzonitrile(3272-08-0)IR
4-Hydroxy-3-nitrobenzonitrile(3272-08-0)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

4-Hydroxy-3-nitrobenzonitrile, 97%(3272-08-0)
[Sigma Aldrich]

3272-08-0(sigmaaldrich)
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