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[ CAS No. 1128-76-3 ]

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Chemical Structure| 1128-76-3
Chemical Structure| 1128-76-3
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Product Details of [ 1128-76-3 ]

CAS No. :1128-76-3 MDL No. :MFCD00013634
Formula : C9H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LVFRSNCBCHABAM-UHFFFAOYSA-N
M.W :184.62 Pubchem ID :70785
Synonyms :

Calculated chemistry of [ 1128-76-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.54
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 3.45
Log Po/w (WLOGP) : 2.52
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 2.67
Consensus Log Po/w : 2.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.0863 mg/ml ; 0.000468 mol/l
Class : Soluble
Log S (Ali) : -3.68
Solubility : 0.0383 mg/ml ; 0.000207 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0591 mg/ml ; 0.00032 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 1128-76-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1128-76-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1128-76-3 ]
  • Downstream synthetic route of [ 1128-76-3 ]

[ 1128-76-3 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 1128-76-3 ]
  • [ 1673-47-8 ]
YieldReaction ConditionsOperation in experiment
88% With hydrazine hydrate In ethanol; waterReflux General procedure: Hydrazides (30–58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3–6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
890 mg With hydrazine hydrate In ethanolReflux To a solution of 3-chlorobenzoic acid (1 g, 6.39 mmol) in ethanol (10 mL) was added cHCl (5 drops) and the mixture heated at reflux overnight. The solvents were evaporated to give the target compound as a white solid. This compound was then dissolved in ethanol (10 mL) and hydrazine hydrate (6.21 mL, 128 mmol) was added and the mixture heated at reflux overnight. Solvents were evaporated and the product was purified by flash chromatography using a gradient mixture of ethyl acetate and hexanes to give the desire compound as a yellow solid (890 mg, 81percent over 2 steps). 1H NMR (CDCl3), ä 7.41 (t, J = 7 Hz, 1H), 7.49 (d, J = 7 Hz, 1H), 7.73 (m, 1H), 7.86 (m, J = 4 Hz, 1H); MS m/z = 171.5, 173.5 (M + H)+.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024
[2] Science Reports of National Tsing Hua University, Series A: Mathematical, Physical, and Engineering Sciences, 1936, vol. <A> 3, p. 443,446
[3] Journal fuer Praktische Chemie (Leipzig), 1901, vol. <2>64, p. 332
[4] Journal of Organic Chemistry, 2004, vol. 69, # 19, p. 6449 - 6454
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2278 - 2282
[6] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 9, p. 2079 - 2087
[7] Journal of Chemical Research, 2010, vol. 34, # 12, p. 680 - 683
[8] Journal of Chemical Research, 2011, vol. 35, # 4, p. 234 - 237
[9] Journal of Chemical Research, 2011, vol. 35, # 6, p. 364 - 367
[10] Letters in Drug Design and Discovery, 2012, vol. 9, # 2, p. 135 - 139
[11] Journal of Chemical Research, 2012, vol. 36, # 7, p. 383 - 386
[12] Tetrahedron, 2014, vol. 70, # 12, p. 2190 - 2194
[13] Archives of Pharmacal Research, 2014, vol. 37, # 7, p. 852 - 861
[14] Marine Drugs, 2014, vol. 12, # 4, p. 1839 - 1858
[15] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3052 - 3056
[16] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 7, p. 1045 - 1055
[17] Asian Journal of Chemistry, 2015, vol. 27, # 10, p. 3605 - 3608
[18] Asian Journal of Chemistry, 2016, vol. 28, # 3, p. 639 - 643
[19] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 11, p. 1998 - 2010
[20] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 2, p. 207 - 212
[21] ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985
[22] Chemical Biology and Drug Design, 2017, vol. 90, # 2, p. 236 - 243
[23] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5652 - 5661
[24] Archiv der Pharmazie, 2017, vol. 350, # 11,
[25] Journal of the Chilean Chemical Society, 2017, vol. 62, # 1, p. 3370 - 3375
[26] Russian Journal of Bioorganic Chemistry, 2017, vol. 43, # 3, p. 328 - 339[27] Bioorg. Khim., 2017, vol. 43, # 3, p. 328 - 339,12
[28] RSC Advances, 2018, vol. 8, # 12, p. 6306 - 6314
  • 2
  • [ 75-00-3 ]
  • [ 535-80-8 ]
  • [ 1128-76-3 ]
YieldReaction ConditionsOperation in experiment
87% With 1,1'-(hexane-1,6-diyl)bis(1,8-diazabicyclo[5.4.0]undec-7-enium) dichlorine In ethanol; water at 70℃; for 2 h; Green chemistry General procedure: Carboxylic acids (1.00 mmol), primary chloroalkanes(1.20mmol) and IL-1 (0.30mmol) were added respectivelyinto a two necked flask equipped with 6mL 50percentaqueous ethanol solution under stirring, then raised the systemtemperature to 70°C for a needed time in water bath.The progress of the reaction was monitored using thin layer chromatography (TLC). When the reaction was over, thereactor was cooled down to room temperature. The mixturewas diluted with water (10mL) and extracted with ethylacetate (3 × 5mL), the extract was dried over anhydrousNa2SO4,filtered, and concentrated in a rotary evaporatorto collect target product. Meanwhile, the reborn catalystcould be applied in the next cycle was after removing thesolvent and dried at 80°C under vacuum for 6h. All theesterification products were further purified by column
Reference: [1] Catalysis Letters, 2017, vol. 147, # 11, p. 2764 - 2771
  • 3
  • [ 108-37-2 ]
  • [ 109-94-4 ]
  • [ 1128-76-3 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 14 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 4
  • [ 64-17-5 ]
  • [ 587-04-2 ]
  • [ 1128-76-3 ]
  • [ 535-80-8 ]
YieldReaction ConditionsOperation in experiment
66% With sodium cyanide In N,N-dimethyl-formamide at 50℃; for 1 h; Molecular sieve General procedure: Aldehyde 1 (1.0 mmol; 1.0 equiv.) and 4 Å molecular sieves (300 mg) were added to a mixture of DMF (3.0 mL) and an appropriate alcohol (or a thiol) (3.0 mL). To the above solution was added sodium cyanide (1.5 mmol; 1.5 equiv). The reaction mixture was stirred in an open flask at 50 C and monitored by TLC. After the complete consumption of 1, the mixture was poured into water (25 mL) and extracted with diethyl ether (5 × 10 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude mixture was further purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to furnish the desired ester compound 3. The aqueous layer was acidified with HCl, extracted with ether, and concentrated to yield the corresponding carboxylic acid 6, which was sufficiently pure needing no further purification.
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 8, p. 2055 - 2061
  • 5
  • [ 64-17-5 ]
  • [ 535-80-8 ]
  • [ 1128-76-3 ]
YieldReaction ConditionsOperation in experiment
90% at 100℃; for 24 h; General procedure: A mixture of acid (0.2 mmol), alcohol (0.6 mmol) and GO (50 wtpercent, calculated with the mass of acid) in ethyl alcohol or DCE (1 mL) was placed in a test tube equipped with a magnetic stirring bar. The mixture was stirred at 100 °C for 24 h. After the reaction was finished, filtered the GO, solvent was removed, and the residue was separated by column chromatography to give the pure sample.
Reference: [1] Synthesis, 2003, # 16, p. 2479 - 2482
[2] Organic Process Research and Development, 2017, vol. 21, # 7, p. 947 - 955
[3] Synlett, 2017, vol. 28, # 8, p. 981 - 985
[4] Canadian Journal of Chemistry, 1983, vol. 61, p. 230 - 234
[5] Journal fuer Praktische Chemie (Leipzig), 1901, vol. <2>64, p. 332
[6] Justus Liebigs Annalen der Chemie, 1857, vol. 102, p. 264
[7] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 9, p. 2079 - 2087
[8] Canadian Journal of Chemistry, 1983, vol. 61, p. 230 - 234
[9] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 6, p. 808 - 816
[10] Journal of Organic Chemistry, 2004, vol. 69, # 19, p. 6449 - 6454
[11] Patent: WO2004/5282, 2004, A1, . Location in patent: Page 41
[12] Journal of Chemical Research, 2010, vol. 34, # 12, p. 680 - 683
[13] Journal of Chemical Research, 2011, vol. 35, # 4, p. 234 - 237
[14] Journal of Chemical Research, 2011, vol. 35, # 6, p. 364 - 367
[15] Journal of Chemical Research, 2012, vol. 36, # 7, p. 383 - 386
[16] Tetrahedron, 2014, vol. 70, # 12, p. 2190 - 2194
[17] Archives of Pharmacal Research, 2014, vol. 37, # 7, p. 852 - 861
[18] Marine Drugs, 2014, vol. 12, # 4, p. 1839 - 1858
[19] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3052 - 3056
[20] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 7, p. 1045 - 1055
[21] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024
[22] Asian Journal of Chemistry, 2015, vol. 27, # 10, p. 3605 - 3608
[23] Asian Journal of Chemistry, 2016, vol. 28, # 3, p. 639 - 643
[24] Chemistry - A European Journal, 2016, vol. 22, # 1, p. 211 - 221
[25] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 11, p. 1998 - 2010
[26] Tetrahedron Letters, 2017, vol. 58, # 6, p. 574 - 577
[27] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 2, p. 207 - 212
[28] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 15 - 25
[29] ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985
[30] Chemical Biology and Drug Design, 2017, vol. 90, # 2, p. 236 - 243
[31] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5652 - 5661
[32] Archiv der Pharmazie, 2017, vol. 350, # 11,
[33] Journal of the Chilean Chemical Society, 2017, vol. 62, # 1, p. 3370 - 3375
[34] Russian Journal of Bioorganic Chemistry, 2017, vol. 43, # 3, p. 328 - 339[35] Bioorg. Khim., 2017, vol. 43, # 3, p. 328 - 339,12
[36] RSC Advances, 2018, vol. 8, # 12, p. 6306 - 6314
  • 6
  • [ 36749-09-4 ]
  • [ 78-09-1 ]
  • [ 1128-76-3 ]
  • [ 105-37-3 ]
  • [ 105-58-8 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 6, p. 1769 - 1771
  • 7
  • [ 108-37-2 ]
  • [ 1609-47-8 ]
  • [ 1128-76-3 ]
Reference: [1] Synthesis, 2004, # 4, p. 568 - 572
  • 8
  • [ 63503-60-6 ]
  • [ 124156-21-4 ]
  • [ 1128-76-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6013 - 6022
  • 9
  • [ 582-33-2 ]
  • [ 1128-76-3 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
  • 10
  • [ 141-78-6 ]
  • [ 535-80-8 ]
  • [ 1128-76-3 ]
Reference: [1] Synthesis, 2003, # 16, p. 2479 - 2482
  • 11
  • [ 64-17-5 ]
  • [ 34158-71-9 ]
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Reference: [1] Synthetic Communications, 1992, vol. 22, # 13, p. 1851 - 1862
  • 12
  • [ 56-34-8 ]
  • [ 937-14-4 ]
  • [ 542-18-7 ]
  • [ 1128-76-3 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 13
  • [ 71-91-0 ]
  • [ 937-14-4 ]
  • [ 108-85-0 ]
  • [ 1128-76-3 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 14
  • [ 64-17-5 ]
  • [ 2905-65-9 ]
  • [ 1128-76-3 ]
Reference: [1] Synthesis, 2003, # 16, p. 2479 - 2482
  • 15
  • [ 108-88-3 ]
  • [ 1128-76-3 ]
  • [ 100-44-7 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 16
  • [ 64-17-5 ]
  • [ 57835-58-2 ]
  • [ 1128-76-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1983, vol. 325, # 6, p. 901 - 907
  • 17
  • [ 110-82-7 ]
  • [ 108-85-0 ]
  • [ 1128-76-3 ]
  • [ 121-44-8 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 18
  • [ 110-82-7 ]
  • [ 542-18-7 ]
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  • [ 121-44-8 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 19
  • [ 281-23-2 ]
  • [ 935-56-8 ]
  • [ 7346-41-0 ]
  • [ 1128-76-3 ]
  • [ 121-44-8 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 20
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 625-99-0 ]
  • [ 1128-76-3 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 58, p. 8100 - 8103
  • 21
  • [ 535-80-8 ]
  • [ 1128-76-3 ]
Reference: [1] Synthesis, 2003, # 16, p. 2479 - 2482
[2] Justus Liebigs Annalen der Chemie, 1857, vol. 102, p. 264
  • 22
  • [ 64-17-5 ]
  • [ 587-04-2 ]
  • [ 1128-76-3 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2070 - 2072
  • 23
  • [ 587-04-2 ]
  • [ 1099-45-2 ]
  • [ 1128-76-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 870 - 878
  • 24
  • [ 121-53-9 ]
  • [ 1128-76-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1857, vol. 102, p. 264
  • 25
  • [ 16331-64-9 ]
  • [ 37156-42-6 ]
  • [ 1128-76-3 ]
  • [ 14609-74-6 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 14, p. 5073 - 5082
  • 26
  • [ 64-17-5 ]
  • [ 618-46-2 ]
  • [ 1128-76-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1857, vol. 102, p. 264
  • 27
  • [ 64-17-5 ]
  • [ 7664-93-9 ]
  • [ 535-80-8 ]
  • [ 1128-76-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1857, vol. 102, p. 264
  • 28
  • [ 1128-76-3 ]
  • [ 74-95-3 ]
  • [ 41011-01-2 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 25, p. 5140 - 5142
  • 29
  • [ 1128-76-3 ]
  • [ 108-95-2 ]
  • [ 60677-14-7 ]
YieldReaction ConditionsOperation in experiment
21% With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 110℃; for 18 h; Inert atmosphere General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(bda)2 (11.5 mg,0.02 mmol), L1 (13.7 mg, 0.03 mmol), K3PO4 (424.5 mg, 2 mmol), and toluene (1.0 mL). After stirring for 15 min, the solution of arylhalide (1.0 mmol) and phenol (1.2 mmol) in toluene (1.5 mL) was added. The septum was replaced with an inside reflux condenser, and then the reaction mixture was stirred for 18 h at 110 C. Then,the reaction mixture was cooled to room temperature and quenched with water (5 mL). After separating the organic phase, the aqueous phase was extracted with ethyl acetate (3 mL3), and the combined organic phase was dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure, and then the crude material was purified by column chromatography on silica gel
Reference: [1] Tetrahedron, 2015, vol. 71, # 30, p. 4927 - 4932
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