14439-61-3

Basic information

• Product Name: 4'-CHLORODIAZEPAM
• Synonyms: 7-Chloro-1,3-dihydro-1-methyl-5-(4-chlorophenyl)-2H-1,4-benzodiazepin-2-one;2H-1,4-Benzodiazepin-2-one, 7-chloro-5-(4-chlorophenyl)-1,3-dihydro-1-methyl-;Aids080743;Aids-080743;7-chloro-1,3-dihydro-1-methyl-5-(p-chlorophenyl)-2h-1,4-benzodiazepin-2-one;7-chloro-5-(4-chlorophenyl)-1,3-dihydro-1-methyl-2h-4-benzodiazepin-2-one;7-chloro-5-(p-chlorophenyl)-1,3-dihydro-1-methyl-2h-4-benzodiazepin-2-one;chlorodiazepam
• CAS NO: 14439-61-3
• Molecular Formula: C₁₆H₁₂Cl₂N₂O
• Molecular Weight: 319.19
• Mol File: 14439-61-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 160-163 °C
• Boiling Point: 517.1°Cat760mmHg
• Flash Point: 266.6°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 8.43E-11mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: +2C to +8C
• Solubility: ethanol: 17 mg/mL
• PKA: 3.08±0.10(Predicted)
• BRN: 685202
• CAS DataBase Reference: 4'-CHLORODIAZEPAM(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORODIAZEPAM(14439-61-3)
• EPA Substance Registry System: 4'-CHLORODIAZEPAM(14439-61-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• RIDADR: 2811
• WGK Germany: 3
• RTECS: DF0500000
• F: 10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 14439-61-3(Hazardous Substances Data)

Usage

Uses

4′-Chlorodiazepam has been used as a translocator protein ligand in mitochondrial functional studies. It has also been used to investigate its protective effects on glucose deprived T98G astrocyte cell lines.

Biochem/physiol Actions

4′-Chlorodiazepam (Ro5-4864) is a potent selective ligand for the mitochondrial translocator protein 18kDa (TSPO), formerly known as the peripheral benzodiazepine receptor (PBR). Ro5-4864 does not bind to GABA(A) receptors and lacks typical benzodiazepine effects, but has been found to be neuroprotective in several studies.

InChI:InChI=1/C16H12Cl2N2O/c1-20-14-7-6-12(18)8-13(14)16(19-9-15(20)21)10-2-4-11(17)5-3-10/h2-8H,9H2,1H3

Synthetic route

N-<4-chloro-2-(4-chlorobenzoyl)phenyl>-N-methylchloroacetamide (99833-82-6) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
With hexamethylenetetramine In methanol; water for 22h; Heating;	94%

N-<4-chloro-2-(4-chlorobenzoyl)phenyl>-N-methylphthalimidoacetate (99833-83-7) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
With hydrazine In methanol; water at 60℃; for 3h;	80%

7-chloro-5-(4-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (5571-60-8) + methyl iodide (74-88-4) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
With sodium methylate In toluene at 20℃; for 168h;	37%

3-(4-chlorobenzene)-5-chloro-2,1-benzoisoxazole (724-07-2) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2) Fe, aq. HCl / 1) 5h, 80 deg C; 2) ethanol, water, 3 h, reflux 2: 95 percent / CHCl3 / 8 h / Heating 3: 80 percent / N2H4 / methanol; H2O / 3 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 2) Fe, aq. HCl / 1) 5h, 80 deg C; 2) ethanol, water, 3 h, reflux 2: 86 percent / benzene / 1) 10 deg C, 50 min. (addition); 2) 90 min. 3: 94 percent / hexamethylenetetramine / methanol; H2O / 22 h / Heating View Scheme

5,4'-dichloro-2-methylaminobenzophenone (78961-59-8) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / CHCl3 / 8 h / Heating 2: 80 percent / N2H4 / methanol; H2O / 3 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 86 percent / benzene / 1) 10 deg C, 50 min. (addition); 2) 90 min. 2: 94 percent / hexamethylenetetramine / methanol; H2O / 22 h / Heating View Scheme

4-chlorobenzonitrile (100-00-5) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 43 percent / KOH / methanol; benzene / 3 h / Ambient temperature 2: 2) Fe, aq. HCl / 1) 5h, 80 deg C; 2) ethanol, water, 3 h, reflux 3: 95 percent / CHCl3 / 8 h / Heating 4: 80 percent / N2H4 / methanol; H2O / 3 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 43 percent / KOH / methanol; benzene / 3 h / Ambient temperature 2: 2) Fe, aq. HCl / 1) 5h, 80 deg C; 2) ethanol, water, 3 h, reflux 3: 86 percent / benzene / 1) 10 deg C, 50 min. (addition); 2) 90 min. 4: 94 percent / hexamethylenetetramine / methanol; H2O / 22 h / Heating View Scheme

p-chlorobenzyl cyanide (140-53-4) → 4-chlorodiazepam (14439-61-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 43 percent / KOH / methanol; benzene / 3 h / Ambient temperature 2: 2) Fe, aq. HCl / 1) 5h, 80 deg C; 2) ethanol, water, 3 h, reflux 3: 95 percent / CHCl3 / 8 h / Heating 4: 80 percent / N2H4 / methanol; H2O / 3 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 43 percent / KOH / methanol; benzene / 3 h / Ambient temperature 2: 2) Fe, aq. HCl / 1) 5h, 80 deg C; 2) ethanol, water, 3 h, reflux 3: 86 percent / benzene / 1) 10 deg C, 50 min. (addition); 2) 90 min. 4: 94 percent / hexamethylenetetramine / methanol; H2O / 22 h / Heating View Scheme

Upstream product

• 99833-82-6 N-<4-chloro-2-(4-chlorobenzoyl)phenyl>-N-methylchloroacetamide 
• 5571-60-8 7-chloro-5-(4-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 
• 74-88-4 methyl iodide 
• 140-53-4 p-chlorobenzyl cyanide 
• 100-00-5 4-chlorobenzonitrile 
• 78961-59-8 5,4'-dichloro-2-methylaminobenzophenone 
• 724-07-2 3-(4-chlorobenzene)-5-chloro-2,1-benzoisoxazole 
• 99833-83-7 N-<4-chloro-2-(4-chlorobenzoyl)phenyl>-N-methylphthalimidoacetate 

Relevant articles and documents

Synthesis and Spectral Properties of 7-Chloro-5-[(o- and p-R1)phenyl]-1-R2-3H-[1,4]benzodiazepin-2-ones

A series of twelve new 7-chloro-5-[(o- and p-R1)phenyl]-1-R2-3H-[1,4] benzo-diazepin-2-ones, which have possible pharmocological properties were synthesized. The synthesis of all the final compounds was carried out by four steps. The structure of all final products was corroborated by ir, 1H nmr, 13C nmr and ms, and have been obtained in 35-94 percent yield.

Synthesis of 7-chloro-5-(4-chlorophenyl)-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one

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