2-Amino-5-chlorobenzophenone
- Iupac Name：(2-amino-5-chlorophenyl)-phenylmethanone
- CAS No.: 719-59-5
- Molecular Weight：231.679
- Modify Date.: 2022-11-29 03:19
- Introduction: A metabolite of Diazepam; it had a much weaker anticonvulsant effect.
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1. Names and Identifiers
- 1.1 Name
- 2-Amino-5-chlorobenzophenone
- 1.2 Synonyms
(2-AMINO-5-CHLOROPHENYL)(PHENYL)METHANONE 2--5 2-Amino-5-chloro 2-Amino-5-chlorobenophenone 2-amino-5-chloro-benzophenone 2-Benzoyl-4-chloroaniline 4-CHLORO-2-BENZOYLANILINE 5-CHLORO-2-AMINOBENZOPHENONE ACB EINECS 211-949-7 IFLAB-BB F1386-0355 LABOTEST-BB LT00259286 Methanone, (2-amino-5-chlorophenyl)phenyl- MFCD00007839 OxazepaM Benzophenone ZR DG BVR
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- 1.3 CAS No.
- 719-59-5
- 1.4 CID
- 12870
- 1.5 EINECS(EC#)
- 211-949-7
- 1.6 Molecular Formula
- C13H10ClNO (isomer)
- 1.7 Inchi
- InChI=1S/C13H10ClNO/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8H,15H2
- 1.8 InChIkey
- ZUWXHHBROGLWNH-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC=C(C=C1)C(=O)C2=C(C=CC(=C2)Cl)N
- 1.10 Isomers Smiles
- C1=CC=C(C=C1)C(=O)C2=C(C=CC(=C2)Cl)N
2. Properties
- 2.1 Density
- 1.274
- 2.1 Melting point
- 96-100℃
- 2.1 Boiling point
- 207℃
- 2.1 Refractive index
- 1.636
- 2.1 Flash Point
- 211℃
- 2.1 Precise Quality
- 231.04500
- 2.1 PSA
- 43.09000
- 2.1 logP
- 3.73440
- 2.1 Solubility
- Solubility in methanol gives very faint turbidity. Soluble in DMSO.
- 2.2 Appearance
- yellow crystalline powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- yellow powder
- 2.5 Color/Form
- Powder
- 2.6 pKa
- 0.06±0.10(Predicted)
- 2.7 Water Solubility
- insoluble
- 2.8 Stability
- Stable. Incompatible with strong oxidizing agents.
- 2.9 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 GHS Classification
- Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 45 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
H315 (95.56%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (95.56%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (93.33%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
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- 3.2 Methods of Manufacturing
- Take 10.0g of intermediate (II) into a three-necked bottle.50ml ethanol, 4.8g iron powder, After refluxing for 0.5 h, 1 ml of sulfuric acid (6 mol/L) was added dropwise.After the completion of the dropwise addition, the reaction was refluxed for 1 h.After the reaction is completed, a NaOH solution is added to adjust the pH to 8, Cool down to 50 ° C, add 0.2g activated carbon, Reflux for 0.5h, Thermal filtration into the crystallization bottle, cooling and crystallization, Ethanol washing, drying to obtain intermediate (III) 9.60g, The yield is 95.1percent.The melting point is 96.3-98.2 °C.A, in a reaction vessel equipped with a stirrer, a reflux condenser, 5-chloro-3-phenyl-benzisoxazole 0.26 mol, the mass fraction of 30percent 2-bromo-5-fluoronitrobenzene solution 390ml, nickel chloride powder 0.46 mol, control the stirring speed at 190 rpm, raise the solution temperature to 78 °C, reflux reaction 120 min; B, adding 90percent of 4-chlorophenethylamine solution with a mass fraction of 21percent slowly add the ethylene glycol dimethyl ether solution with a mass fraction of 37percent adding time to control at 110min, continue to reflux reaction 5h. C, add the mass fraction of 27percent sodium bicarbonate solution 200ml, reduce the solution temperature to 16 °C, molecular sieve bleaching, filtration, the filtrate was concentrated, again lowering the solution temperature to 5 °C, the mass fraction of 70percent triethylamine solution washing, calcium oxide dehydrating agent dehydration, to give crystals of 2-amino-5-chlorobenzophenone 55.59 g, yield 92percent.1) Weigh 180 g of raw material 5-chloro-3-phenyl-2, 1-benzisoxazole into 1.5 L of anhydrous methanol and 1.5 L of acetonitrile, After stirring and dissolving, add 10g Pd/C catalyst with Pd content of 3percent, stir and mix to form material I, The flow rate of the slurry pump was adjusted so that the flow rate of the material I was 40.0 g/min and entered the preheating module of the microreactor. 2) Adjust the flow rate of the H2 gas flowmeter to 350ml/min, and directly enter the reaction module group and material I to undergo catalytic hydrogenation reaction without preheating.As shown in Figure 2, the molar ratio of 5-chloro-3-phenyl-2, 1-benzisoxazole to hydrogen is 1:1.2, the reaction temperature is 80°C, the residence time of the reaction is 35s, and the reaction pressure is 1.0Mpa; then enter the cooling module, cooling module temperature is 30 °C, Collect the reaction solution from the outlet of the cooling module, recover the catalyst by filtration, and recover the solvent by distillation under reduced pressure.The residue was recrystallized from 80percent ethanol solution to obtain the target product 2-amino-5-chlorobenzophenone, 168.96g, yield 92.79percent, purity 99.68percent.General procedure: Under a NGeneral procedure: A solution of 2-phenylindole (1a, 97 mg, 0.5 mmol) and CsIn the installation of a stirrer, thermometer, In the reaction vessel of the reflux condenser, 3.55 mol of benzamide (2) was added, Raise the temperature of the solution to 123 ° C, Dropping p-chloroaniline (3) 1.41mol, after adding slowly warming to 195 , Adding 5.9 mol of stannous chloride, Raise the temperature of the solution to 250 ° C, At this temperature for 4 h, Until no gas is generated, Reducing the solution temperature to 95 ° C, Add the mass fraction of 15percent potassium chloride solution 500ml, The solution temperature was raised to 130 ° C, After 4h, Pour out the water layer, After cooling the solution, Precipitation of dark suspended solids, The suspension was added to a 2.5 L mass fraction of 55percent phosphoric acid solution, Reflux 23h, After cooling, The solution was poured into a 1200 ml solution of 25percent sodium nitrate solution, Reduce the solution temperature to 8 ° C, Add the mass fraction of 85percent cyclohexane extraction, Cyclohexane layer by adding the mass fraction of 35percent sodium sulfite solution 300ml, 2.5kPa vacuum distillation, Add the mass fraction of 95percent acetonitrile extraction 7 times, Precipitation of solids, filter, Phosphorus pentoxide was dehydrated to give 297.68 g of 2-amino-5-chlorobenzophenone in yellow crystals in a yield of 91percent
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- 3.3 Usage
- A metabolite of Diazepam; it had a much weaker anticonvulsant effect.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- 26-36
- 4.1 Hazard Declaration
- H315-H319-H335
- 4.1 RIDADR
- 25kgs
- 4.1 Caution Statement
- P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- PC4933500
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx and Cl?.
Hazard Codes:?
Xi,Xn
The Risk Statements information of? 2-AMINO-5-CHLOROBENZOPHENONE?:
22:? Harmful if swallowed?
20/21/22:? Harmful by inhalation, in contact with skin and if swallowed
36/37/38:? Irritating to eyes, respiratory system and skin
The Safety Statements information of??2-AMINO-5-CHLOROBENZOPHENONE?:
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
WGK Germany: 3
RTECS: PC4933500
HS Code: 29223900
- 4.3 Specification
-
??2-Amino-5-chlorobenzophenone ,?its cas register number is 719-59-5. It also can be called?(2-Amino-5-chlorophenyl)phenylmethanone ; 2-Benzoyl-4-chloroaniline ; 3-14-00-00214 (Beilstein Handbook Reference) ; 5-Chloro-2-aminobenzophenone .?2-Amino-5-chlorobenzophenone (CAS NO.719-59-5) is a yellow powder.
- 4.4 Toxicity
- LD50 orally in Rabbit: 10000 mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
719-59-5Total: 61 Synthesis Route
9. Other Information
- 9.0 Usage
- It is used in the heterocyclic syntheses based on the reactions of dimethyl acetylenedicarboxylate.
- 9.1 BRN
- 475640
- 9.2 Chemical Properties
- yellow powder
- 9.3 Uses
- A metabolite of Diazepam; it had a much weaker anticonvulsant effect.
- 9.4 Synthesis Reference(s)
- Tetrahedron Letters, 35, p. 6811, 1994 DOI: 10.1016/0040-4039(94)85011-9
- 9.5 General Description
-
2-Amino-5-chlorobenzophenone is a organic nonlinear optical material.
- 9.6 Storage Conditions
- Take 10.0g of intermediate (II) into a three-necked bottle.50ml ethanol, 4.8g iron powder, After refluxing for 0.5 h, 1 ml of sulfuric acid (6 mol/L) was added dropwise.After the completion of the dropwise addition, the reaction was refluxed for 1 h.After the reaction is completed, a NaOH solution is added to adjust the pH to 8, Cool down to 50 ° C, add 0.2g activated carbon, Reflux for 0.5h, Thermal filtration into the crystallization bottle, cooling and crystallization, Ethanol washing, drying to obtain intermediate (III) 9.60g, The yield is 95.1percent.The melting point is 96.3-98.2 °C.A, in a reaction vessel equipped with a stirrer, a reflux condenser, 5-chloro-3-phenyl-benzisoxazole 0.26 mol, the mass fraction of 30percent 2-bromo-5-fluoronitrobenzene solution 390ml, nickel chloride powder 0.46 mol, control the stirring speed at 190 rpm, raise the solution temperature to 78 °C, reflux reaction 120 min; B, adding 90percent of 4-chlorophenethylamine solution with a mass fraction of 21percent slowly add the ethylene glycol dimethyl ether solution with a mass fraction of 37percent adding time to control at 110min, continue to reflux reaction 5h. C, add the mass fraction of 27percent sodium bicarbonate solution 200ml, reduce the solution temperature to 16 °C, molecular sieve bleaching, filtration, the filtrate was concentrated, again lowering the solution temperature to 5 °C, the mass fraction of 70percent triethylamine solution washing, calcium oxide dehydrating agent dehydration, to give crystals of 2-amino-5-chlorobenzophenone 55.59 g, yield 92percent.1) Weigh 180 g of raw material 5-chloro-3-phenyl-2, 1-benzisoxazole into 1.5 L of anhydrous methanol and 1.5 L of acetonitrile, After stirring and dissolving, add 10g Pd/C catalyst with Pd content of 3percent, stir and mix to form material I, The flow rate of the slurry pump was adjusted so that the flow rate of the material I was 40.0 g/min and entered the preheating module of the microreactor. 2) Adjust the flow rate of the H2 gas flowmeter to 350ml/min, and directly enter the reaction module group and material I to undergo catalytic hydrogenation reaction without preheating.As shown in Figure 2, the molar ratio of 5-chloro-3-phenyl-2, 1-benzisoxazole to hydrogen is 1:1.2, the reaction temperature is 80°C, the residence time of the reaction is 35s, and the reaction pressure is 1.0Mpa; then enter the cooling module, cooling module temperature is 30 °C, Collect the reaction solution from the outlet of the cooling module, recover the catalyst by filtration, and recover the solvent by distillation under reduced pressure.The residue was recrystallized from 80percent ethanol solution to obtain the target product 2-amino-5-chlorobenzophenone, 168.96g, yield 92.79percent, purity 99.68percent.General procedure: Under a NGeneral procedure: A solution of 2-phenylindole (1a, 97 mg, 0.5 mmol) and CsIn the installation of a stirrer, thermometer, In the reaction vessel of the reflux condenser, 3.55 mol of benzamide (2) was added, Raise the temperature of the solution to 123 ° C, Dropping p-chloroaniline (3) 1.41mol, after adding slowly warming to 195 , Adding 5.9 mol of stannous chloride, Raise the temperature of the solution to 250 ° C, At this temperature for 4 h, Until no gas is generated, Reducing the solution temperature to 95 ° C, Add the mass fraction of 15percent potassium chloride solution 500ml, The solution temperature was raised to 130 ° C, After 4h, Pour out the water layer, After cooling the solution, Precipitation of dark suspended solids, The suspension was added to a 2.5 L mass fraction of 55percent phosphoric acid solution, Reflux 23h, After cooling, The solution was poured into a 1200 ml solution of 25percent sodium nitrate solution, Reduce the solution temperature to 8 ° C, Add the mass fraction of 85percent cyclohexane extraction, Cyclohexane layer by adding the mass fraction of 35percent sodium sulfite solution 300ml, 2.5kPa vacuum distillation, Add the mass fraction of 95percent acetonitrile extraction 7 times, Precipitation of solids, filter, Phosphorus pentoxide was dehydrated to give 297.68 g of 2-amino-5-chlorobenzophenone in yellow crystals in a yield of 91percent
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- 9.7 Mesh Entry Terms
- 2-ACB
- 9.8 Manufacturing Info
- Methanone, (2-amino-5-chlorophenyl)phenyl-: ACTIVE
10. Computational chemical data
- Molecular Weight: 231.679g/mol
- Molecular Formula: C13H10ClNO
- Compound Is Canonicalized: True
- XLogP3-AA: 3.8
- Exact Mass: 231.0450916
- Monoisotopic Mass: 231.0450916
- Complexity: 250
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 43.1
- Heavy Atom Count: 16
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccByIAAEAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgIQAAAADA6BmCAwwIBAAACIAqRSQACCAAAkBwAIiAEAZsgIIDqBl5GAIYBgkAAIyccYiMCOAABAIAACAAAAAIBAAAQAAAAAAAAAAA==
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