Product Name

  • Name

    Quetiapine fumarate

  • EINECS 1308068-626-2
  • CAS No. 111974-72-2
  • Article Data16
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 174-176 °C
  • Formula C46H54N6O8S2
  • Boiling Point 556.5 °C at 760 mmHg
  • Molecular Weight 883.102
  • Flash Point 290.4 °C
  • Transport Information
  • Appearance white crystalline solid
  • Safety 60-61-45-36/37-16
  • Risk Codes 22-50/53-52/53-39/23/24/25-23/24/25-11
  • Molecular Structure Molecular Structure of 111974-72-2 (Quetiapine fumarate)
  • Hazard Symbols Xn,N,T,F
  • Synonyms Ethanol,2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-,(2E)-2-butenedioate (2:1) (salt) (9CI);Ethanol, 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-,(E)-2-butenedioate (2:1) (salt);Dibenzo[b,f][1,4]thiazepine, ethanol deriv.;ICI 204636;Quetiapine hemifumarate;Seroquel;ZD 5077;ZM204636;
  • PSA 221.80000
  • LogP 4.04660

Synthetic route

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

Quetiapine
111974-69-7

Quetiapine

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
In ethyl acetate; toluene at 20℃; for 1.08333h; Product distribution / selectivity; Heating / reflux;99%
Stage #1: Quetiapine With pyrographite In methanol for 0.5h; Reflux;
Stage #2: (2E)-but-2-enedioic acid at 40℃; pH=4 - 5;		98%
In methanol at 10 - 25℃; for 1.58333h; Heating / reflux;94%
1-[2-(2-hydroxyethoxy)ethyl]piperazine
13349-82-1

1-[2-(2-hydroxyethoxy)ethyl]piperazine

dibenzo[b,f][1,4]thiazepin-11-ylamine hydrochloride
1176987-11-3

dibenzo[b,f][1,4]thiazepin-11-ylamine hydrochloride

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: 1-[2-(2-hydroxyethoxy)ethyl]piperazine; dibenzo[b,f][1,4]thiazepin-11-ylamine hydrochloride at 172 - 176℃; for 5h;
Stage #2: In water at 20 - 65℃;
Stage #3: (2E)-but-2-enedioic acid In isopropyl alcohol at 4 - 20℃; Product distribution / selectivity;		83%
Stage #1: 1-[2-(2-hydroxyethoxy)ethyl]piperazine; dibenzo[b,f][1,4]thiazepin-11-ylamine hydrochloride at 173 - 175℃; for 5h;
Stage #2: With potassium carbonate In water at 20 - 75℃;
Stage #3: (2E)-but-2-enedioic acid In isopropyl alcohol at 4 - 20℃; Product distribution / selectivity;		79%
...Expand
titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

1-[2-(2-hydroxyethoxy)ethyl]piperazine
13349-82-1

1-[2-(2-hydroxyethoxy)ethyl]piperazine

dibenzo[b,f][1,4]thiazepin-11-one
3159-07-7

dibenzo[b,f][1,4]thiazepin-11-one

A

isopropyl alcohol
67-63-0

isopropyl alcohol

B

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
With pentan-1-ol at 160℃; for 32h; Product distribution / selectivity; Heating / reflux;A n/a
B 75%
...Expand
11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride
753475-15-9

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride

2-(2-Chloroethoxy)ethanol
628-89-7

2-(2-Chloroethoxy)ethanol

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride; 2-(2-Chloroethoxy)ethanol With sodium carbonate; sodium iodide; tetrabutylammomium bromide In toluene at 105℃; for 24h; Heating / reflux;
Stage #2: With (2E)-but-2-enedioic acid In toluene Heating / reflux;		72%
Stage #1: 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride; 2-(2-Chloroethoxy)ethanol With sodium carbonate; sodium iodide; tetrabutylammomium bromide In toluene at 107℃; for 40h; Heating / reflux;
Stage #2: With (2E)-but-2-enedioic acid In toluene at 100℃;		72%
Stage #1: 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride; 2-(2-Chloroethoxy)ethanol With sodium carbonate; sodium iodide; tetrabutylammomium bromide In butan-1-ol at 115 - 120℃; for 24h; Heating / reflux;
Stage #2: With (2E)-but-2-enedioic acid In butan-1-ol Heating / reflux;		70.8%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: 11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl)dibenzo[b,f]-1,4-thiazepine hydrochloride With sodium hydroxide In methanol; water; toluene at 40 - 50℃; for 0.166667h; pH=13 - 14;
Stage #2: (2E)-but-2-enedioic acid In ethanol for 0.166667h; Heating / reflux;
1-[2-(2-hydroxyethoxy)ethyl]piperazine
13349-82-1

1-[2-(2-hydroxyethoxy)ethyl]piperazine

11-chloro-dibenzo[b,f][1,4]thiazepine
13745-86-3

11-chloro-dibenzo[b,f][1,4]thiazepine

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: 1-[2-(2-hydroxyethoxy)ethyl]piperazine; 11-chloro-dibenzo[b,f][1,4]thiazepine In toluene at 25 - 112℃; Large scale reaction;
Stage #2: (2E)-but-2-enedioic acid In ethanol at 55 - 60℃; for 0.5h; Large scale reaction;		15.4 kg
...Expand
11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride
753475-15-9

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride

2-(2-Chloroethoxy)ethanol
628-89-7

2-(2-Chloroethoxy)ethanol

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride; 2-(2-Chloroethoxy)ethanol With 1-methyl-pyrrolidin-2-one; sodium carbonate; sodium iodide In propan-1-ol
Stage #2: (2E)-but-2-enedioic acid In ethanol
...Expand
2-(2-Chloroethoxy)ethanol
628-89-7

2-(2-Chloroethoxy)ethanol

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: With sodium hydrogencarbonate In water; dimethyl sulfoxide at 20℃; for 0.166667h;
Stage #2: 2-(2-Chloroethoxy)ethanol; sodium iodide In water; dimethyl sulfoxide; toluene at 95 - 100℃;
Stage #3: (2E)-but-2-enedioic acid In ethanol at 45 - 80℃;
dibenzo[b,f][1,4]thiazepin-11-one
3159-07-7

dibenzo[b,f][1,4]thiazepin-11-one

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / 20 - 100 °C / Industry scale; Inert atmosphere
2.1: toluene; dimethyl sulfoxide / 3 h / 25 - 30 °C / Industry scale; Inert atmosphere
3.1: sodium hydrogencarbonate / water; dimethyl sulfoxide / 0.17 h / 20 °C / Industry scale
3.2: 95 - 100 °C / Industry scale
3.3: 4 h / 5 - 80 °C / Industry scale
View Scheme
Multi-step reaction with 3 steps
1.1: pyrophosphoryl chloride; N,N-dimethyl-aniline / toluene / 4.5 h / 110 - 112 °C / Green chemistry
2.1: toluene / 105 - 107 °C
3.1: pyrographite / methanol / 0.5 h / Reflux
3.2: 40 °C / pH 4 - 5
View Scheme
N-Dealkyl Quetiapine dihydrochloride

N-Dealkyl Quetiapine dihydrochloride

2-(2-Chloroethoxy)ethanol
628-89-7

2-(2-Chloroethoxy)ethanol

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Stage #1: N-Dealkyl Quetiapine dihydrochloride With sodium hydrogencarbonate In water; dimethyl sulfoxide at 20℃; for 0.166667h; Industry scale;
Stage #2: 2-(2-Chloroethoxy)ethanol With sodium iodide In water; dimethyl sulfoxide; toluene at 95 - 100℃; Industry scale;
Stage #3: (2E)-but-2-enedioic acid In ethanol at 5 - 80℃; for 4h; Product distribution / selectivity; Industry scale;
...Expand
2‑(2‑nitrophenylsulfanyl)benzoic acid
19806-43-0

2‑(2‑nitrophenylsulfanyl)benzoic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / dichloromethane / 40 °C
1.2: 0 - 5 °C
2.1: formic acid; iron / 85 - 90 °C
3.1: methanol
View Scheme
Thiosalicylic acid
147-93-3

Thiosalicylic acid

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water; isopropyl alcohol / Inert atmosphere; Reflux
2.1: thionyl chloride / dichloromethane / 40 °C
2.2: 0 - 5 °C
3.1: formic acid; iron / 85 - 90 °C
4.1: methanol
View Scheme
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

quetiapine fumarate
111974-72-2

quetiapine fumarate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water; isopropyl alcohol / Inert atmosphere; Reflux
2.1: thionyl chloride / dichloromethane / 40 °C
2.2: 0 - 5 °C
3.1: formic acid; iron / 85 - 90 °C
4.1: methanol
View Scheme
quetiapine fumarate
111974-72-2

quetiapine fumarate

11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl)dibenzo[b,f]-1,4-thiazepine hydrochloride
930086-71-8

11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl)dibenzo[b,f]-1,4-thiazepine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 60℃; for 7.5h; Product distribution / selectivity;
With hydrogenchloride In water; isopropyl alcohol at 0 - 70℃; for 8.5h; Product distribution / selectivity;
ethyl bromide
74-96-4

ethyl bromide

quetiapine fumarate
111974-72-2

quetiapine fumarate

2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-1-ethyl ethanol
1011758-06-7

2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-1-ethyl ethanol

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 15 - 20℃; for 8h;
β‐cyclodextrin
7585-39-9

β‐cyclodextrin

quetiapine fumarate
111974-72-2

quetiapine fumarate

C42H70O35*C21H25N3O2S

C42H70O35*C21H25N3O2S

Conditions
ConditionsYield
In water
β‐cyclodextrin
7585-39-9

β‐cyclodextrin

quetiapine fumarate
111974-72-2

quetiapine fumarate

2C42H70O35*C21H25N3O2S

2C42H70O35*C21H25N3O2S

Conditions
ConditionsYield
In water

Quetiapine Fumarate Chemical Properties

Product Name: Quetiapine Fumarate (CAS NO.111974-72-2)

Molecular Formula: C46H54N6O8S2
Molecular Weight: 883.086360 g/mol
Appearance: White Crystalline Solid
Melting Point: 174-176°C
Boiling Point: 556.5°Cat760mmHg
Flash Point: 290.4°C
Enthalpy of Vaporization: 88.18 kJ/mol 
Vapour Pressure: 3.22E-13 mmHg at 25°C 
XLogP3-AA:
H-Bond Donor: 4
H-Bond Acceptor: 14
Structure Descriptors of Quetiapine Fumarate (CAS NO.111974-72-2):
  IUPAC Name: 2-[2-(4-benzo[b][1,5]benzothiazepin-6-ylpiperazin-1-yl)ethoxy]ethanol;(E)-but-2-enedioic acid
  Canonical SMILES: C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C(=CC(=O)O)C(=O)O
  Isomeric SMILES: C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C(=C/C(=O)O)\C(=O)O
  InChI: InChI=1S/2C21H25N3O2S.C4H4O4/c2*25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21;5-3(6)1-2-4(7)8/h2*1-8,25H,9-16H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+ 
  InChIKey: ZTHJULTYCAQOIJ-WXXKFALUSA-N
Categories: Active Pharmaceutical Ingredients; Antipsychotic; Intermediates & Fine Chemicals; Pharmaceuticals; Quetiapine

Quetiapine Fumarate Uses

 Quetiapine Fumarate (CAS NO.111974-72-2) is used as an antipsychotic.

Quetiapine Fumarate Specification

 Quetiapine Fumarate , its CAS NO. is 111974-72-2, the synonyms are 2-(2-(4-Dibenzo(b,f)(1,4)thiazepin-11-yl-1-
piperazinyl)ethoxy)ethanol fumarate (2:1) (salt) ; 2-(2-(4-Dibenzo(b,f)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanol ; Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (E)-2-butenedioate (2:1) (salt) .

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