| Identification | More | [Name]
4-Chloro-3-nitrobenzaldehyde | [CAS]
16588-34-4 | [Synonyms]
3-NITRO-4-CHLOROBENZALDEHYDE
4-CHLORO-3-NITROBENZALDEHYDE
AKOS BBS-00003244
ASISCHEM R36965
TIMTEC-BB SBB007674
4-chloro-3-nitro-benzaldehyd
Benzaldehyde, 4-chloro-3-nitro-
4-Chloro-3-Nitrobenzaldehyde 3-Nitro-4-Chlorobenzaldehyde
4-Chlor-3-nitrobenzaldehyde | [EINECS(EC#)]
240-645-7 | [Molecular Formula]
C7H4ClNO3 | [MDL Number]
MFCD00007078 | [Molecular Weight]
185.56 | [MOL File]
16588-34-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow powder | [Melting point ]
61-63 °C (lit.) | [Boiling point ]
276.5°C (rough estimate) | [density ]
1.4791 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
4g/l | [form ]
Powder | [color ]
Off-white to light yellow to light green | [Water Solubility ]
4 g/L (98 ºC) | [Sensitive ]
Air Sensitive | [Detection Methods]
HPLC | [BRN ]
778323 | [InChI]
1S/C7H4ClNO3/c8-6-2-1-5(4-10)3-7(6)9(11)12/h1-4H | [InChIKey]
HETBKLHJEWXWBM-UHFFFAOYSA-N | [SMILES]
[O-][N+](=O)c1cc(C=O)ccc1Cl | [CAS DataBase Reference]
16588-34-4(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Chloro-3-nitrobenzaldehyde(16588-34-4) | [EPA Substance Registry System]
16588-34-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29130000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow powder | [Uses]
4-Chloro-3-nitrobenzaldehyde is a potent inhibitor of VCAM-1 expression and a potential drug candidate for autoimmune and allergic inflammatory diseases. | [Synthesis]
General procedure for the synthesis of 4-chloro-3-nitrobenzaldehyde from 4-chlorobenzaldehyde: 4-chlorobenzaldehyde (70 g, 0.5 mol) was added in batches to a mixture of nitrosonitrous nitric acid (55 mL) and sulfuric acid (55 mL) at 5°C with continuous stirring for 2 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water (1 L) while stirring was maintained. Subsequently, the precipitate was collected by filtration and recrystallized with ethanol/water solvent mixture to afford the target product 4-chloro-3-nitrobenzaldehyde (90 g, 97% yield) as white needle-like crystals. The melting point of the product was 62-63 °C. | [References]
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
[2] European Journal of Medicinal Chemistry, 2014, vol. 77, p. 361 - 377
[3] Journal of Chemical Research, 2008, # 12, p. 722 - 724
[4] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2013, vol. 43, # 8, p. 977 - 983
[5] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2014, vol. 44, # 7, p. 921 - 926 |
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