| Identification | More | [Name]
4-Cyanobenzoyl chloride | [CAS]
6068-72-0 | [Synonyms]
4-CYANOBENZOYL CHLORIDE
LABOTEST-BB LTBB000677
P-CYANOBENZOYL CHLORIDE
4-(Chlorocarbonyl)benzonitrile
4-Cyanbenzoesαurechlorid
4-Cyanobenzoicacidchloride
Benzoylchloride,4-cyano-
Benzoylchloride,p-cyano-
cyanobenzoylchloride
4-Cyan-benzoic acid chloride
4-Cyanocbenzoyl chloride
4-Cyanobenzoyl chloride 98%
4-Cyanobenzoyl chloride ,97%
4-cyanobenzoic chloride
4-Cyanobenzenecarbonyl chloride | [EINECS(EC#)]
228-005-5 | [Molecular Formula]
C8H4ClNO | [MDL Number]
MFCD00001822 | [Molecular Weight]
165.58 | [MOL File]
6068-72-0.mol |
| Chemical Properties | Back Directory | [Appearance]
almost white to beige crystalline powder | [Melting point ]
68-70 °C(lit.)
| [Boiling point ]
110 °C / 2mmHg | [density ]
1.2744 (rough estimate) | [refractive index ]
1.5430 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Crystalline Powder | [color ]
Almost white to beige | [Water Solubility ]
Reacts with water. | [Sensitive ]
Moisture Sensitive | [Detection Methods]
HPLC | [BRN ]
386729 | [InChI]
InChI=1S/C8H4ClNO/c9-8(11)7-3-1-6(5-10)2-4-7/h1-4H | [InChIKey]
USEDMAWWQDFMFY-UHFFFAOYSA-N | [SMILES]
C(Cl)(=O)C1=CC=C(C#N)C=C1 | [CAS DataBase Reference]
6068-72-0(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [F ]
10-21 | [Hazard Note ]
Irritant | [REACH Registrations]
Active | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29269090 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Eye Dam. 1
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
almost white to beige crystalline powder | [Uses]
4-Cyanobenzoyl chloride has been used in the synthesis of new liquid crystalline heteroaromatic compounds containing the five-membered isoxazole, tetrazole and 1,2,4-oxadiazole rings. It has been used in the synthesis of substituted benzoate esters and to study their excited-state behavior. | [Definition]
ChEBI: 4-cyanobenzoyl chloride is an acyl chloride consisting of benzoyl chloride in which the hydrogen at position 4 is replaced by a cyano group. It is a nitrile, a member of benzenes and an acyl chloride. It is functionally related to a benzoyl chloride. | [General Description]
4-Cyanobenzoyl chloride participates in the benzylamine acylation of Argopore MB-CHO resin in the presence of pyridine and catalyst. It reacts with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinoxyl (4-hydroxy-TEMPO) in pyridine under nitrogen atmosphere to form 4-cyanobenzoyl-TEMPO. | [Synthesis]
4-Cyanobenzoic acid (30.00 g, 203.90 mmol) was added to thionyl chloride (29.11 g, 244.68 mmol) in batches under magnetic stirring. Subsequently, three drops of N,N-dimethylformamide (DMF) were added to the reaction system as a catalyst. The reaction mixture was heated to reflux with continuous stirring for 1.5 h. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solution was distilled at 235 °C to afford the white solid product p-cyanobenzoyl chloride in 98% yield (5.50 g) with a melting point of 67.2-68.2 °C. The structure of the product was confirmed by the following characterization data: 1H NMR (600 MHz, DMSO-d6) δ 8.06 (d, J = 7.8 Hz, 2H), 7.96 (d, J = 7.8 Hz, 2H); 13C NMR (151 MHz, DMSO-d6) δ 165.9, 134.7, 132.6, 129.9, 118.1, 115.1; IR (KBr, νmax/cm-1)3101, 3051, 2229, 1772, 1739, 1597, 1401, 1287, 1211, 1167, 896, 851, 634; high-resolution mass spectrometry (HR-MS, ESI) m/z: [M + H]+ calculated value C8H4ClNO + H+ 166.0053, measured value 166.0054. | [Purification Methods]
If the IR shows the presence of OH, then treat it with SOCl2 boil for 1hour, evaporate and distil it in a vacuum. The distillate solidifies and can be recrystallised from pet ether. It is moisture sensitive and an IRRITANT. [Ashley et al. J Chem Soc 103 1942, Fison et al. J Org Chem 16 648 1951,[Beilstein 9 III 4255, 14 IV 3327.] | [References]
[1] Patent: US6433211, 2002, B1
[2] Journal of Chemical Research, 2015, vol. 39, # 9, p. 524 - 526
[3] Patent: US6433211, 2002, B1
[4] Patent: CN107226808, 2017, A. Location in patent: Paragraph 0280-0283
[5] Annali di Chimica (Rome, Italy), 1952, vol. 42, p. 94,101 |
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