204-02-4

Basic information

• Product Name: perimidine
• Synonyms: perimidine;1,3-Diaza-1H-phenalene;Benzo[de]quinazoline
• CAS NO: 204-02-4
• Molecular Formula: C₁₁H₈N₂
• Molecular Weight: 168.19
• Mol File: 204-02-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: 223°C
• Boiling Point: 287.13°C (rough estimate)
• Flash Point: 178.2°C
• Appearance: /
• Density: 1.1722 (rough estimate)
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• PKA: 6.35(at 20℃)
• CAS DataBase Reference: perimidine(CAS DataBase Reference)
• NIST Chemistry Reference: perimidine(204-02-4)
• EPA Substance Registry System: perimidine(204-02-4)

Safety Data

• Hazardous Substances Data: 204-02-4(Hazardous Substances Data)

Usage

General Description

Perimidine, also known as 4H-pyrimido[4,5-b][1,4]benzothiazine, is a heterocyclic compound consisting of a pyrimidine and benzothiazine ring system. It is a yellow crystalline solid that is used in the synthesis of pharmaceuticals and agrochemicals. Perimidine derivatives have shown potential as anti-inflammatory, antiviral, and anticancer agents. Additionally, they have been studied for their use as fluorescent probes and materials for organic electronic devices. Perimidine derivatives have also been investigated for their potential in the treatment of neurodegenerative diseases and as ligands for metal ion coordination chemistry. Overall, perimidine and its derivatives have diverse applications in the fields of medicine, materials science, and coordination chemistry.

InChI:InChI=1/C11H8N2/c1-3-8-4-2-6-10-11(8)9(5-1)12-7-13-10/h1-7H,(H,12,13)

Synthetic route

orthoformic acid triethyl ester (122-51-0) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester at 20℃; for 0.25h; Stage #2: naphthalene-1,8-diamine at 20℃; for 3h;	100%

2,3-dihydro-2,2-dimethylperimidine (6364-17-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
In formic acid; hydrogen bromide for 1.5h; Heating;	97%

formic acid (64-18-6) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
In ethanol	96%
In ethanol for 0.666667h; Heating;	95%
With hydrogen bromide In acetone Reflux;	95%

2,3-dihydroperimidine (69098-80-2) → 1-H-perimidine (204-02-4)

Conditions	Yield
With sodium disulfite In ethanol; water for 2h; Heating;	95%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With carbon dioxide In water at 150℃; under 37503.8 Torr; for 5h;	93.1%
With 1,1,1,3,3,3-hexamethyl-disilazane at 120℃; for 12h; Green chemistry;	50%
With zinc(II) acetate dihydrate In neat (no solvent) at 120℃; under 7600.51 Torr; for 18h; Autoclave; Inert atmosphere; Green chemistry;	41%

benzylpenicilloic acid α-phenylethylamide (121766-89-0) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4) + 3,3-dimethyl-D-cysteine (52-67-5) + phenaceturic acid α-phenethylamide (102016-26-2)

Conditions	Yield
In water; acetic acid for 2h; Heating;	A 85% B 69% C 74%

methanol (67-56-1) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With [(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br]; potassium tert-butylate In toluene at 120℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;	69%

carbon monoxide (201230-82-2) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 100℃; under 22502.3 Torr; for 48h; Autoclave;	66%

C15H26N6O + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
In toluene at 100℃; for 48h;	44%

N-formyldiethylamine (617-84-5) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane at 120℃; for 12h; Green chemistry;	38%

carbon dioxide (124-38-9) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With phenylsilane; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene at 70℃; for 24h;	35%
With diphenylsilane; C33H36BO6(3-)*Eu(3+)*H2O*2C3H7NO In acetonitrile at 120℃; under 7500.75 Torr; for 24h; Autoclave;	34%
With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; phenylsilane In tetrahydrofuran at 70℃; under 750.075 - 2250.23 Torr; for 24h; Schlenk technique; Inert atmosphere; Glovebox;

2,3-dihydro-2,2-dimethylperimidine (6364-17-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → perimidine-9-carbaldehyde (925446-80-6) + 1-isopropylperimidine + 1-H-perimidine (204-02-4)

Conditions	Yield
With trichlorophosphate at 65 - 70℃; for 2h;	A 4% B 13% C 0.07%

1,3,5-Triazine (290-87-9) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

perimidine-2-carboxylic acid (146603-28-3) + nitrobenzene (98-95-3) → 1-H-perimidine (204-02-4)

Conditions	Yield
oder mit anderen hochsiedenden Loesungsmitteln;

ethyl 1H-perimidine-2-carboxylate (109735-80-0) → 1-H-perimidine (204-02-4)

Conditions	Yield
With hydrogenchloride at 140 - 160℃;

oxalic acid (144-62-7) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4) + 2,2'-diperimidinyl (1904-61-6)

N,N'-diphenylformamidine (864131-95-3) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
at 160℃;

oxalic acid diethyl ester (95-92-1) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4) + 2,2'-diperimidinyl (1904-61-6)

chloroform (67-66-3) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With calcium oxide at 140℃; im Rohr;

hydrogenchloride (7647-01-0) + perimidine-2-carboxylic acid (146603-28-3) → 1-H-perimidine (204-02-4)

hydrogenchloride (7647-01-0) + ethyl 1H-perimidine-2-carboxylate (109735-80-0) → 1-H-perimidine (204-02-4)

Conditions	Yield
12-36-stuendiges Kochen;
at 140 - 160℃;

perimidine-carboxylic acid-(2) → 1-H-perimidine (204-02-4)

Conditions	Yield
With hydrogenchloride at 140 - 160℃;
With nitrobenzene

water (7732-18-5) + oxalic acid (144-62-7) + naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4) + perimidine-2-carboxylic acid (146603-28-3)

naphthalene-1,8-diamine (479-27-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / aq. HBr; formic acid / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 2: concentrated hydrochloric acid / 140 - 160 °C View Scheme
With formic acid In water

6(7)-acetylperimidine (56314-38-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With PPA

6(7)-acetylperimidine (56314-38-6) → 1-H-perimidine (204-02-4)

Conditions	Yield
With hydroxylamine hydrochloride In PPA

1-H-perimidine (204-02-4) → 1H,1'H-[6,6']biperimidinyl (1412913-64-4)

Conditions	Yield
With aluminum (III) chloride In nitromethane at 20℃;	96%

1-H-perimidine (204-02-4) + 1-chloromethyl-3-methyl-benzene (620-19-9) → 1-(3-methylbenzyl)perimidine

Conditions	Yield
Stage #1: 1-H-perimidine With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 1-chloromethyl-3-methyl-benzene In dimethyl sulfoxide at 110℃; for 0.5h; Microwave irradiation;	95%

1-H-perimidine (204-02-4) + acetyl chloride (75-36-5) → 6(7)-acetylperimidine (56314-38-6)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; Reflux;	94%

1-H-perimidine (204-02-4) + methyl iodide (74-88-4) → 1,3-dimethyl-1H-perimidin-3-ium chloride (37471-37-7)

Conditions	Yield
Stage #1: 1-H-perimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In N,N-dimethyl-formamide for 12h; Inert atmosphere; Schlenk technique; Reflux;	93%
Stage #1: 1-H-perimidine With potassium hydroxide In acetonitrile at 20℃; for 1h; Stage #2: methyl iodide In acetonitrile for 12h; Reflux;	78%
With potassium carbonate In acetonitrile for 6h; Reflux;	32%

1-H-perimidine (204-02-4) + 1-iodo-propane (107-08-4) → 1,3-dipropyl-1H-perimidin-3-ium iodide

Conditions	Yield
Stage #1: 1-H-perimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 1-iodo-propane In N,N-dimethyl-formamide for 12h; Inert atmosphere; Schlenk technique; Reflux;	92%

1,3,5-Triazine (290-87-9) + 1-H-perimidine (204-02-4) → perimidine-6(7)-carbaldehyde (925446-81-7)

Conditions	Yield
With aq. PPA at 55 - 60℃; for 1h;	91%

1,3,5-Triazine (290-87-9) + 1-H-perimidine (204-02-4) + benzaldehyde (100-52-7) → 6-phenyl-1,3,7-triazapyrene (1020166-30-6)

Conditions	Yield
With polyphosphoric acid at 60 - 70℃; for 9h;	91%

1-bromo-butane (109-65-9) + 1-H-perimidine (204-02-4) → 1-n-butylperimidine

Conditions	Yield
With benzyl chloride In acetonitrile; mineral oil at 0 - 20℃; for 25h;	89%
Stage #1: 1-H-perimidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 25h;	87%
With sodium hydride In tetrahydrofuran at 20℃; Reflux;	86%

1,3,5-Triazine (290-87-9) + 1-H-perimidine (204-02-4) + 4-bromo-benzaldehyde (1122-91-4) → 6-(4-bromophenyl)-1,3,7-triazapyrene (1395276-43-3)

Conditions	Yield
With polyphosphoric acid at 60 - 70℃; for 9h;	89%

1-H-perimidine (204-02-4) + benzyl chloride (100-44-7) → 1-benzylperimidine (27310-93-6)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 3h;	88%
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; for 25h; Inert atmosphere;

1-H-perimidine (204-02-4) + 2-(bromomethyl)-1,3,5-triisopropylbenzene (166519-14-8) → C27H32N2 (1615212-43-5)

Conditions	Yield
Stage #1: 1-H-perimidine With sodium hydride In tetrahydrofuran for 24h; Inert atmosphere; Schlenk technique; Reflux; Stage #2: 2-(bromomethyl)-1,3,5-triisopropylbenzene In tetrahydrofuran for 24h; Inert atmosphere; Schlenk technique; Reflux;	87%

5-bromopyrimidine (4595-59-9) + 1-H-perimidine (204-02-4) → 7-(5-bromo-3,4-dihydropyrimidin-4-yl)-1H-perimidine

Conditions	Yield
With methanesulfonic acid at 20℃; for 0.25h;	87%
With methanesulfonic acid at 20℃;

1-H-perimidine (204-02-4) + methyl chloroformate (79-22-1) + phenylacetylene (536-74-3) → dimethyl 2-(phenylethynyl)-2H-perimidine-1,3-dicarboxylate

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	86%

1-H-perimidine (204-02-4) + cinnamoyl chloride (102-92-1) → 6-hydroxy-1,3-diazapyrene

Conditions	Yield
With aluminum tri-bromide In 1,2-dichloro-ethane at 20℃; for 0.5h;	84%
With aluminum tri-bromide In 1,2-dichloro-ethane at 20℃; for 0.5h; Friedel-Crafts reaction;	45%

2,4,6-trimethyl-s-triazine (823-94-9) + 1-H-perimidine (204-02-4) + benzaldehyde (100-52-7) → 6(8)-oxo-8(6)-phenyl-1,6,7,8-tetrahydro-1,3-diazapyrene (362047-61-8)

Conditions	Yield
Stage #1: 2,4,6-trimethyl-s-triazine; 1-H-perimidine; benzaldehyde at 60 - 70℃; for 8h; Stage #2: With water for 0.0833333h; Reflux;	84%

1-H-perimidine (204-02-4) + (2-nitroethenyl)benzene (102-96-5) → 8-phenyl-1,8-dihydropyrido[2,3,4-gh]perimidin-7(6H)-one (1413442-26-8)

Conditions	Yield
With 80 percent polyphosphoric acid at 65 - 70℃; for 5h;	84%

1-H-perimidine (204-02-4) → 6(7)-nitroperimidine (56314-44-4)

Conditions	Yield
With ammonium nitrate; acetic acid Reflux;	83%

1,3,5-Triazine (290-87-9) + 1-H-perimidine (204-02-4) + 4-nitrobenzaldehdye (555-16-8) → 6-(4-nitrophenyl)-1,3,7-triazapyrene (1395276-47-7)

Conditions	Yield
With polyphosphoric acid at 60 - 70℃; for 9h;	83%

1-H-perimidine (204-02-4) + 2,4,6-triphenyl-1,3,5-triazine (493-77-6) → 6,9-dibenzoylperimidine (1159338-26-7)

Conditions	Yield
With PPA; water at 70 - 75℃; for 2.5h;	82%

1-H-perimidine (204-02-4) + 1,3-diphenylpropanedione (120-46-7) → 6,8-diphenylbenzo[gh]perimidine (211929-01-0)

Conditions	Yield
With sulfuric acid In water at 95 - 100℃; regioselective reaction;	82%

1-H-perimidine (204-02-4) + acetylacetone (123-54-6) → 6,8-dimethylbenzo[gh]perimidine (1020166-24-8)

Conditions	Yield
With sulfuric acid In water at 95 - 100℃; regioselective reaction;	82%

1-H-perimidine (204-02-4) + methyl iodide (74-88-4) → 1-methylperimidine (19585-93-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 2h; Ambient temperature;	81%
With potassium hydroxide In chlorobenzene; toluene for 3h; Heating;	71%
Stage #1: 1-H-perimidine With potassium hydroxide In ethanol at 20℃; for 1h; Reflux; Darkness; Stage #2: methyl iodide In ethanol for 3h; Reflux;	61%

1-H-perimidine (204-02-4) → perimidine-6(7)-sulfonic acid (74861-88-4)

Conditions	Yield
With sulfuric acid for 0.25h; Ambient temperature;	81%

2,4,6-trimethyl-s-triazine (823-94-9) + 1-H-perimidine (204-02-4) + 4-nitrobenzaldehdye (555-16-8) → 8(6)-(4-nitrophenyl)-6(8)-oxo-1,6,7,8-tetrahydro-1,3-diazapyrene (1395276-61-5)

Conditions	Yield
Stage #1: 2,4,6-trimethyl-s-triazine; 1-H-perimidine; 4-nitrobenzaldehdye at 60 - 70℃; for 8h; Stage #2: With water for 0.0833333h; Reflux;	81%

Upstream product

• 290-87-9 1,3,5-Triazine 
• 479-27-6 naphthalene-1,8-diamine 
• 146603-28-3 perimidine-2-carboxylic acid 
• 98-95-3 nitrobenzene 
• 864131-95-3 N,N'-diphenylformamidine 
• 95-92-1 oxalic acid diethyl ester 
• 64-18-6 formic acid 
• 67-66-3 chloroform 
• 6364-17-6 2,3-dihydro-2,2-dimethylperimidine 
• 68-12-2 N,N-dimethyl-formamide 
• 56314-38-6 6⁽⁷⁾-acetylperimidine 
• 617-84-5 N-formyldiethylamine 
• 109735-80-0 ethyl 1H-perimidine-2-carboxylate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 362047-59-4 4⁽⁹⁾-Cinnamoylperimidine 
• 362047-60-7 6⁽⁷⁾-Cinnamoylperimidine 
• 211929-01-0 6,8-diphenylbenzo[gh]perimidine 
• 519148-63-1 9-o-chlorobenzoylperimidine 
• 77151-26-9 N,N'-dibenzoyl-1,8-naphthalenediamine 
• 77151-24-7 N-benzoyl-N'-formyl-1,8-naphthalenediamine 
• 77151-25-8 N,N'-dibenzoyl-N-formyl-1,8-naphthalenediamine 
• 1020166-30-6 6-phenyl-1,3,7-triazapyrene 
• 56314-38-6 6⁽⁷⁾-acetylperimidine 
• 56314-41-1 6⁽⁷⁾-benzoylperimidine 
• 1174205-43-6 6,8-di(4-bromophenyl)-1,3,7-triazapyrene 
• 1009813-19-7 6,8-diphenyl-1,3,7-triazapyrene 
• 1174205-44-7 6,8-di(4-nitrophenyl)-1,3,7-triazapyrene 
• 56314-41-1 6⁽⁷⁾-benzoylperimidine 

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Relevant articles and documents

Selective recognition of acetate ion by perimidinium-based receptors

The first perimidinium-based receptors 1 and 2 have been designed and synthesized. The anion binding properties of the receptors were evaluated in DMSO by UV-vis, fluorescence spectroscopy, and 1H NMR methods. The results demonstrate that both receptors 1 and 2 exhibit good selectivity to acetate. The (C- H)+· · ·X- type ionic hydrogen bonding between the perimidinium moieties and acetate is the key interaction for the recognition.

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peri-Naphthylenediamines 31.* Study of interconversions of 2,3-dihydroperimidines and 1,8-bis(dialkylamino)naphthaienes. Convenient synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidine and a monoisopropyl analog of the "proton sponge"

Efficient procedures were developed for the two-step synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidines and for the one-step synthesis of 1,3-dimethyl-2,3-dihydroperimidines starting from 1,8-diaminonaphthalenes. New possibilities of the use of 2,3-dihydroperimidinium salts in the synthesis of 1,8-bis(dialkylamino)naphthalenes ("proton sponges") containing the N-isopropyl group along with the N-methyl groups were demonstrated. The 1,1,2,2,3-pentamethyl-2,3-dihydroperimidinium cation exists in the acyclic iminium form responsible for its high reactivity.

METHOD OF CARBON MONOXIDE FIXATION AND METHOD OF AMINE FORMYLATION

The present invention relates to a method for fixing carbon monoxide in a metal-free condition and a method for formating amine using the same.

In Situ Formation of Frustrated Lewis Pairs in a Water-Tolerant Metal-Organic Framework for the Transformation of CO2

Frustrated Lewis pairs (FLPs) consist of sterically hindered Lewis acids and Lewis bases, which provide high catalytic activity towards non-metal-mediated activation of “inert” small molecules, including CO2 among others. One critical issue of homogeneous FLPs, however, is their instability upon recycling, leading to catalytic deactivation. Herein, we provide a solution to this issue by incorporating a bulky Lewis acid-functionalized ligand into a water-tolerant metal-organic framework (MOF), named SION-105, and employing Lewis basic diamine substrates for the in situ formation of FLPs within the MOF. Using CO2 as a C1-feedstock, this combination allows for the efficient transformation of a variety of diamine substrates into benzimidazoles. SION-105 can be easily recycled by washing with MeOH and reused multiple times without losing its identity and catalytic activity, highlighting the advantage of the MOF approach in FLP chemistry.