Product Name

  • Name

    Demoxepam

  • EINECS 213-515-2
  • CAS No. 963-39-3
  • Article Data28
  • CAS DataBase
  • Density 1.405 g/cm3
  • Solubility
  • Melting Point 235-236 °C (decomp)
  • Formula C15H11ClN2O2
  • Boiling Point 447.4oC at 760mmHg
  • Molecular Weight 286.718
  • Flash Point 2℃
  • Transport Information
  • Appearance
  • Safety 16-26-36/37
  • Risk Codes 11-20/21/22-36
  • Molecular Structure Molecular Structure of 963-39-3 (Demoxepam)
  • Hazard Symbols F,Xn
  • Synonyms 5-Phenyl-7-chloro-3H-1,4-benzodiazepin-2(1H)-one4-oxide;7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide;7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide;Chlordiazepoxide lactam;NSC 169898;NSC 46007;NSC 46077;1,3-Dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide;
  • PSA 57.85000
  • LogP 2.73660

Synthetic route

diazepam
439-14-5

diazepam

A

desmethyldiazepam
1088-11-5

desmethyldiazepam

B

oxazepam
604-75-1

oxazepam

C

demoxepam
963-39-3

demoxepam

D

diazepam 4-oxide
2888-64-4

diazepam 4-oxide

E

temazepam
846-50-4

temazepam

F

6-chloro-1-methyl-4-phenyl-2(1H)-quinazolinone
20927-53-1

6-chloro-1-methyl-4-phenyl-2(1H)-quinazolinone

Conditions
ConditionsYield
With dihydrogen peroxide; 1H-imidazole; {5,10,15,20-tetrakis(pentafluorophenyl)porphynato}manganese(III) chloride; ammonium acetate In 1,1,1,3',3',3'-hexafluoro-propanol; water; 4-methyl-1,2,3-trifluorobenzene for 4.83333h; Product distribution / selectivity;A 4%
B 0%
C 0%
D 5%
E 7%
F 1%
...Expand
chlordiazepoxide
58-25-3

chlordiazepoxide

A

6-Chloro-4-hydroxy-3-methyl-4-phenyl-3,4-dihydro-quinazoline-2-carbaldehyde oxime

6-Chloro-4-hydroxy-3-methyl-4-phenyl-3,4-dihydro-quinazoline-2-carbaldehyde oxime

B

N-nitrosochlordiazepoxide
51715-17-4

N-nitrosochlordiazepoxide

C

demoxepam
963-39-3

demoxepam

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 37℃; for 1h; Product distribution; varying pH; varying amounts of reagents;
...Expand
Chlordiazepoxide hydrochloride
438-41-5

Chlordiazepoxide hydrochloride

demoxepam
963-39-3

demoxepam

Conditions
ConditionsYield
With water at 37℃; for 960h;
methyl isocyanate
624-83-9

methyl isocyanate

demoxepam
963-39-3

demoxepam

10-chloro-1-methyl-11b-phenyl-7,11b-dihydro-1H-benzo[f][1,2,4]oxadiazolo[2,3-d][1,4]diazepine-2,6-dione
49626-81-5

10-chloro-1-methyl-11b-phenyl-7,11b-dihydro-1H-benzo[f][1,2,4]oxadiazolo[2,3-d][1,4]diazepine-2,6-dione

Conditions
ConditionsYield
In tetrahydrofuran
demoxepam
963-39-3

demoxepam

8-chloro-9b-phenyl-5,9b-dihydro-benzo[f]oxazirino[2,3-d][1,4]diazepin-4-one
27090-87-5

8-chloro-9b-phenyl-5,9b-dihydro-benzo[f]oxazirino[2,3-d][1,4]diazepin-4-one

Conditions
ConditionsYield
In tetrahydrofuran Irradiation;
trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

demoxepam
963-39-3

demoxepam

Trifluoro-acetic acid 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl ester

Trifluoro-acetic acid 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl ester

Conditions
ConditionsYield
for 1.5h;
demoxepam
963-39-3

demoxepam

6-chloro-4-phenyl-2-quinazolinone
4797-43-7

6-chloro-4-phenyl-2-quinazolinone

Conditions
ConditionsYield
With sodium hydroxide for 0.5h; Irradiation;
for 0.5h; Irradiation;
demoxepam
963-39-3

demoxepam

[3-2H2]nordiazepam 4-oxide
181648-03-3

[3-2H2]nordiazepam 4-oxide

Conditions
ConditionsYield
With deuteriated sodium hydroxide In deuteromethanol for 8h; Heating;0.92 g
demoxepam
963-39-3

demoxepam

<3-2H>oxazepam

<3-2H>oxazepam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.92 g / NaOD / CH3OD / 8 h / Heating
2: 1 g / 3 h / Heating
3: 0.49 g / NaOD / CH3OD / 0.5 h / Ambient temperature
View Scheme
demoxepam
963-39-3

demoxepam

3,3-dideuterio-7-chloro-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepine-2(3H)-one

3,3-dideuterio-7-chloro-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepine-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.92 g / NaOD / CH3OD / 8 h / Heating
2: 0.79 g / PCl3 / CHCl3 / 3 h / Heating
3: 1.) 4M NaOD / 1.) CH3CN, 5 min, 2.) CH3CN, RT, 5 h
View Scheme
demoxepam
963-39-3

demoxepam

[3-2H]oxazepam 3-acetate
181648-04-4

[3-2H]oxazepam 3-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.92 g / NaOD / CH3OD / 8 h / Heating
2: 1 g / 3 h / Heating
View Scheme
demoxepam
963-39-3

demoxepam

<3-2H2>nordiazepam
51278-96-7

<3-2H2>nordiazepam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.92 g / NaOD / CH3OD / 8 h / Heating
2: 0.79 g / PCl3 / CHCl3 / 3 h / Heating
View Scheme
demoxepam
963-39-3

demoxepam

7-chloro-3-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one-3d

7-chloro-3-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one-3d

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
3: 82 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.) -70 deg C, 2.) to -10 deg C, 25 min
4: 50 percent / sodium hydride / tetrahydrofuran / 3 h / 25 °C
5: 26 g / 2 N NaOD, deuterium oxide / dimethylformamide
View Scheme
demoxepam
963-39-3

demoxepam

oxazepam
604-75-1

oxazepam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
View Scheme
demoxepam
963-39-3

demoxepam

1-allyl-7-chloro-3-fluoro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
62659-56-7

1-allyl-7-chloro-3-fluoro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
3: 82 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.) -70 deg C, 2.) to -10 deg C, 25 min
4: 64 percent / sodium hydride / tetrahydrofuran / 2 h / 25 °C
View Scheme
demoxepam
963-39-3

demoxepam

7-chloro-3-fluoro-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepine-1-carboxylic acid methylamide
62659-61-4

7-chloro-3-fluoro-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepine-1-carboxylic acid methylamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
3: 82 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.) -70 deg C, 2.) to -10 deg C, 25 min
4: 56 percent / benzene / 48 h / Heating
View Scheme
demoxepam
963-39-3

demoxepam

7-chloro-3-fluoro-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepine-1-carboxylic acid ethylamide
62659-62-5

7-chloro-3-fluoro-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepine-1-carboxylic acid ethylamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
3: 82 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.) -70 deg C, 2.) to -10 deg C, 25 min
4: 54 percent / benzene / 48 h / Heating
View Scheme
demoxepam
963-39-3

demoxepam

3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
60628-57-1

3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
3: 82 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.) -70 deg C, 2.) to -10 deg C, 25 min
View Scheme
With SbCl5; HF
demoxepam
963-39-3

demoxepam

3-fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one
60628-55-9

3-fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.5 h
2: aq. 5 percent sodium bicarbonate / ethanol / 18 h / 25 °C
3: 82 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.) -70 deg C, 2.) to -10 deg C, 25 min
4: 50 percent / sodium hydride / tetrahydrofuran / 3 h / 25 °C
View Scheme
demoxepam
963-39-3

demoxepam

10-chloro-1-methyl-2,6-dioxo-11b-phenyl-1,5,6,11b-tetrahydro-2H-benzo[f][1,2,4]oxadiazolo[2,3-d][1,4]diazepine-7-carboxylic acid methylamide
49626-82-6

10-chloro-1-methyl-2,6-dioxo-11b-phenyl-1,5,6,11b-tetrahydro-2H-benzo[f][1,2,4]oxadiazolo[2,3-d][1,4]diazepine-7-carboxylic acid methylamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran
2: tetrahydrofuran
View Scheme
Re(CO)2(P(C6H5)3)2Cl
35796-29-3

Re(CO)2(P(C6H5)3)2Cl

demoxepam
963-39-3

demoxepam

Re(CO)2(P(C6H5)3)2(C15H10ClN2O2)
206127-02-8

Re(CO)2(P(C6H5)3)2(C15H10ClN2O2)

Conditions
ConditionsYield
With NEt3 In ethanol; dichloromethane addn. of 2 equiv. of ligand soln. (in EtOH) to Re-complex soln. (in CH2Cl2/EtOH=2:1), refluxing with few drops of NEt3 for 3 h; concn., crystn. on EtOH addn., filtration, washing (H2O, EtOH, Et2O), recrystn. (CH2Cl2/EtOH); elem. anal.;
Tc(CO)2(P(C6H5)3)2Cl

Tc(CO)2(P(C6H5)3)2Cl

demoxepam
963-39-3

demoxepam

Tc(CO)2(P(C6H5)3)2(C15H10ClN2O2)

Tc(CO)2(P(C6H5)3)2(C15H10ClN2O2)

Conditions
ConditionsYield
With NEt3 In ethanol; dichloromethane addn. of 2 equiv. of ligand soln. (in EtOH) to Tc-complex soln. (in CH2Cl2/EtOH=2:1), refluxing with few drops of NEt3 for 3 h; concn., crystn. on EtOH addn., filtration, washing (H2O, EtOH, Et2O), recrystn. (CH2Cl2/EtOH); elem. anal.;

Demoxepam Specification

The systematic name of Demoxepam is 7-chloro-4-hydroxy-5-phenyl-3H-1,4-benzodiazepin-2-one. With the CAS registry number 963-39-3, it is also named as 1,3-Dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide.Its EINECS number is 213-515-2.  The product's classification codes are Drug / Therapeutic Agent; Tranquilizer [minor]. Besides, it is crystal. In addition, its molecular formula is C15H11ClN2O2 and molecular weight is 286.71.

The other characteristics of Demoxepam can be summarized as: (1)EINECS: 213-515-2; (2)ACD/LogP: 0.73; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1; (5)ACD/LogD (pH 7.4): 1; (6)ACD/BCF (pH 5.5): 2; (7)ACD/BCF (pH 7.4): 2; (8)ACD/KOC (pH 5.5): 59; (9)ACD/KOC (pH 7.4): 59; (10)H bond acceptors: 4; (11)H bond donors: 1; (12)Freely Rotating Bonds: 1; (13)Polar Surface Area: 57.85 Å2; (14)Index of Refraction: 1.682; (15)Molar Refractivity: 77.276 cm3; (16)Molar Volume: 204.127 cm3; (17)Polarizability: 30.635×10-24cm3; (18)Surface Tension: 61.125 dyne/cm; (19)Density: 1.405 g/cm3; (20)Melting Point: 239-241 °C; (21)Water Solubility 783 mg/L at 25 °C; (22)Vapor Pressure 2.45E-13 mm Hg at 25 °C

Preparation of Demoxepam: frist, please use p-Nitrochlorobenzene to react with Benzyl nitrile in Alcohol with Sodium hydroxide. And you will get 5-Chloro-3-phenylbenzimidazole isoxazole. Then use Iron powder-hydrochloric acid to restore to get 2-Amino-5-chloro benzophenone. And then you can oxime it with Hydroxylamine hydrochloride to get 2-Amino-5-chloro benzophenone oxime. You can get 6-Chloro-2-chloromethyl-4-phenyl quinazoline-3-oxide by cyclization of Chloroacetic chloride. At last, you will get this chemical by the action of Sodium hydroxide.

Uses of Demoxepam: this chemical is a drug which is a benzodiazepine derivative. And it is a metabolite of chlordiazepoxide which has anticonvulsant properties and presumably other characteristic benzodiazepine properties.

People can use the following data to convert to the molecule structure.
(1)SMILES:Clc1ccc2NC(=O)C[N+](/[O-])=C(\c2c1)c3ccccc3;
(2)Std. InChI:InChI=1S/C15H11ClN2O2/c16-11-6-7-13-12(8-11)15(10-4-2-1-3-5-10)18(20)9-14(19)17-13/h1-8H,9H2,(H,17,19);
(3)Std. InChIKey:GGRWZBVSUZZMKS-UHFFFAOYSA-N.

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 290mg/kg (290mg/kg)   Current Therapeutic Research, Clinical & Experimental. Vol. 7, Pg. 590, 1965.
mouse LD50 oral 1950mg/kg (1950mg/kg)   "Benzodinzenines," Garattini, S., et al., New York, Raven Press, 1973Vol. -, Pg. 39, 1973.
mouse LD50 subcutaneous > 400mg/kg (400mg/kg)   Current Therapeutic Research, Clinical & Experimental. Vol. 7, Pg. 590, 1965.
rabbit LD50 oral 628mg/kg (628mg/kg)   Current Therapeutic Research, Clinical & Experimental. Vol. 7, Pg. 590, 1965.
rat LD50 oral > 4gm/kg (4000mg/kg)   Current Therapeutic Research, Clinical & Experimental. Vol. 7, Pg. 590, 1965.

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