Product Name

  • Name

    PHENAZINE-1-CARBOXYLIC ACID

  • EINECS
  • CAS No. 2538-68-3
  • Article Data34
  • CAS DataBase
  • Density 1.431 g/cm3
  • Solubility
  • Melting Point 242-244℃
  • Formula C13H8N2O2
  • Boiling Point 494.6 °C at 760 mmHg
  • Molecular Weight 224.219
  • Flash Point 252.9 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 2538-68-3 (PHENAZINE-1-CARBOXYLIC ACID)
  • Hazard Symbols IrritantXi
  • Synonyms Phenazinecarboxylicacid (6CI);NSC 15851;Phenazine-a-carboxylic acid;Tubermycin B;
  • PSA 63.08000
  • LogP 2.48120

Synthetic route

1-hydroxymethylphenazine
1082-79-7

1-hydroxymethylphenazine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 80℃; for 10h; Reagent/catalyst; Green chemistry;98.2%
6-nitrodiphenylamine-2-carboxylic acid
54420-95-0

6-nitrodiphenylamine-2-carboxylic acid

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium ethanolate In ethanol for 1h; Heating;82%
With sodium tetrahydroborate; sodium hydroxide for 4h;79.4%
With sodium tetrahydroborate; sodium ethanolate In ethanol at 65℃; for 24h; Inert atmosphere;54%
N-(2-fluorophenyl)-3-nitroanthranilic acid
106976-05-0

N-(2-fluorophenyl)-3-nitroanthranilic acid

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 1h; Heating;82%
1-cyanophenazine
411211-73-9

1-cyanophenazine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With sulfuric acid at 140℃; for 1h;75%
With potassium hydroxide
N-(2-methoxyphenyl)-3-nitroanthranilic acid
38120-51-3

N-(2-methoxyphenyl)-3-nitroanthranilic acid

A

tubermycin B
2538-68-3

tubermycin B

B

9-methoxyphenazine-1-carboxylic acid
23531-25-1

9-methoxyphenazine-1-carboxylic acid

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium methylate In methanol Heating;A n/a
B 33%
anthranilic acid
118-92-3

anthranilic acid

nitrobenzene
98-95-3

nitrobenzene

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With potassium hydroxide at 150 - 160℃;30%
With potassium hydroxide at 145 - 160℃;
2-((2-chlorophenyl)amino)-3-nitrobenzoic acid
38120-54-6

2-((2-chlorophenyl)amino)-3-nitrobenzoic acid

A

tubermycin B
2538-68-3

tubermycin B

B

9-chlorophenazine-1-carboxylic acid
103942-93-4

9-chlorophenazine-1-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborateA n/a
B 21%
N-(2-phenoxyphenyl)-3-nitroanthranilic acid
103942-78-5

N-(2-phenoxyphenyl)-3-nitroanthranilic acid

A

tubermycin B
2538-68-3

tubermycin B

B

9-phenoxyphenazine-1-carboxylic acid
103942-79-6

9-phenoxyphenazine-1-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate for 48h; Reductive cyclization; Heating;A n/a
B 10%
1-methyl-phenazine
1016-59-7

1-methyl-phenazine

acetic anhydride
108-24-7

acetic anhydride

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid; acetic acid
1-methyl-phenazine
1016-59-7

1-methyl-phenazine

acetic acid
64-19-7

acetic acid

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With chromium(VI) oxide
phenazine-1-carboxamide
550-89-0

phenazine-1-carboxamide

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
With potassium hydroxide
With hydrogenchloride
With sulfuric acid
With water Acidic conditions;
2-bromo-3-nitro-benzoic acid
573-54-6

2-bromo-3-nitro-benzoic acid

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / N-ethylmorpholine / CuCl / various solvent(s) / 4 h / 80 °C
2: NaBH4; 2 N aq. NaOH / 48 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 79 percent / CuCl, Cu, N-ethylmorpholine / various solvent(s) / 15 h / 70 - 80 °C
2: NaBH4, NaOMe / methanol / Heating
View Scheme
Multi-step reaction with 2 steps
1: 78 percent / CuCl, Cu, N-ethylmorpholine / various solvent(s) / 15 h / 70 °C
2: 82 percent / NaBH4, NaOEt / ethanol / 1 h / Heating
View Scheme
2-phenoxyaniline
2688-84-8

2-phenoxyaniline

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / N-ethylmorpholine / CuCl / various solvent(s) / 4 h / 80 °C
2: NaBH4; 2 N aq. NaOH / 48 h / Heating
View Scheme
1-bromophenazine
3331-27-9

1-bromophenazine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 61 percent / dimethylsulfoxide / 3 h / 200 °C
2: 75 percent / aq. H2SO4 / 1 h / 140 °C
View Scheme
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / CuCl, Cu, N-ethylmorpholine / various solvent(s) / 15 h / 70 - 80 °C
2: NaBH4, NaOMe / methanol / Heating
View Scheme
aniline
62-53-3

aniline

ethane-α.β-bis-sulfonic acid chloride

ethane-α.β-bis-sulfonic acid chloride

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / CuCl, Cu, N-ethylmorpholine / various solvent(s) / 15 h / 70 °C
2: 82 percent / NaBH4, NaOEt / ethanol / 1 h / Heating
View Scheme
2-Chloroaniline
95-51-2

2-Chloroaniline

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 58 percent / CuCl, Cu, N-ethylmorpholine / various solvent(s) / 15 h / 70 - 80 °C
2: NaBH4, 2N aq. NaOH
View Scheme
2-Fluoroaniline
348-54-9

2-Fluoroaniline

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Cu, cuprous chloride, N-ethylmorpholine / various solvent(s) / 18 h / 70 °C
2: 82 percent / NaBH4 / ethanol / 1 h / Heating
View Scheme
1-methyl-1,2,3,4-tetrahydrophenazine
856342-39-7

1-methyl-1,2,3,4-tetrahydrophenazine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iodine; acetic acid
2: CrO3
View Scheme
2,3-dinitro-benzonitrile
90325-27-2

2,3-dinitro-benzonitrile

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol
2: iron (II)-oxalate dihydrate; lead / 260 °C
3: aq.-ethanolic KOH
View Scheme
3-nitro-2-(phenylamino)benzonitrile
411212-01-6

3-nitro-2-(phenylamino)benzonitrile

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron (II)-oxalate dihydrate; lead / 260 °C
2: aq.-ethanolic KOH
View Scheme
aniline
62-53-3

aniline

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol
2: iron (II)-oxalate dihydrate; lead / 260 °C
3: aq.-ethanolic KOH
View Scheme
Multi-step reaction with 2 steps
1: N-ethylmorpholine;; copper(l) chloride; copper / 16 h / 70 °C / Inert atmosphere
2: sodium tetrahydroborate; sodium ethanolate / ethanol / 24 h / 65 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: N-ethylmorpholine;; 2.3-butanediol; copper(l) chloride; copper / 16 h / 70 °C / Inert atmosphere
2: sodium tetrahydroborate; sodium ethanolate / ethanol / 24 h / 65 °C / Inert atmosphere
View Scheme
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; acetic acid
2: iodine; acetic acid
3: CrO3
View Scheme
3-methyl-1,2-benzenediamine
2687-25-4

3-methyl-1,2-benzenediamine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 10 h / 210 - 220 °C / Inert atmosphere
1.2: air / 3 h / 210 - 220 °C
2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux
3.1: sodium carbonate / N,N-dimethyl-formamide; water / 2 h / 80 °C
4.1: 2,2'-azobis(isobutyronitrile); oxygen; N-Bromosuccinimide / acetonitrile / 10 h / 80 °C / Green chemistry
View Scheme
benzene-1,2-diol
120-80-9

benzene-1,2-diol

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 10 h / 210 - 220 °C / Inert atmosphere
1.2: air / 3 h / 210 - 220 °C
2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux
3.1: sodium carbonate / N,N-dimethyl-formamide; water / 2 h / 80 °C
4.1: 2,2'-azobis(isobutyronitrile); oxygen; N-Bromosuccinimide / acetonitrile / 10 h / 80 °C / Green chemistry
View Scheme
1-methyl-phenazine
1016-59-7

1-methyl-phenazine

tubermycin B
2538-68-3

tubermycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux
2: sodium carbonate / N,N-dimethyl-formamide; water / 2 h / 80 °C
3: 2,2'-azobis(isobutyronitrile); oxygen; N-Bromosuccinimide / acetonitrile / 10 h / 80 °C / Green chemistry
View Scheme
chorismic acid
617-12-9

chorismic acid

A

tubermycin B
2538-68-3

tubermycin B

B

phenazine-1,6-dicarboxylic acid
23462-25-1

phenazine-1,6-dicarboxylic acid

Conditions
ConditionsYield
With XpzABCDETF Enzymatic reaction;
tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid chloride

phenazine-1-carboxylic acid chloride

Conditions
ConditionsYield
With thionyl chloride98%
With thionyl chloride In toluene at 100℃; for 3h;97%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 50℃; for 12h;92%
tubermycin B
2538-68-3

tubermycin B

1‑amino‑2‑(2,4‑difluorophenyl)‑3‑(1H‑1,2,4‑triazol‑1‑yl)propan‑2‑ol
126916-76-5

1‑amino‑2‑(2,4‑difluorophenyl)‑3‑(1H‑1,2,4‑triazol‑1‑yl)propan‑2‑ol

N-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)phenazine-1-carboxamide

N-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)phenazine-1-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 10.5h; Inert atmosphere;96%
methanol
67-56-1

methanol

tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid methyl ester
3225-19-2

phenazine-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid86%
With sulfuric acid
Tetraethylene glycol
112-60-7

Tetraethylene glycol

tubermycin B
2538-68-3

tubermycin B

tetraethyleneglycol phenazine-1-carboxylate

tetraethyleneglycol phenazine-1-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 24h;86%
tubermycin B
2538-68-3

tubermycin B

phenazin-1-ylamine
2876-22-4

phenazin-1-ylamine

Conditions
ConditionsYield
Stage #1: tubermycin B With diphenyl phosphoryl azide; triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran for 2h; Inert atmosphere; Reflux;		61%
Stage #1: tubermycin B With diphenyl phosphoryl azide; triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran for 2h; Curtius Rearrangement; Reflux; Inert atmosphere;		61%
Stage #1: tubermycin B With diphenyl phosphoryl azide; triethylamine
Stage #2: With water
Stage #1: tubermycin B With diphenyl phosphoryl azide; triethylamine
Stage #2: With water
tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid 5-oxide
27210-90-8

phenazine-1-carboxylic acid 5-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water at 55℃; for 17h; Inert atmosphere;58%
With dihydrogen peroxide; acetic acid In water at 55℃; for 17h; Inert atmosphere;58%
With dihydrogen peroxide In acetic acid at 55 - 60℃; for 24h;38%
With dihydrogen peroxide; acetic acid
tubermycin B
2538-68-3

tubermycin B

4-phenyl-1-butylamine
13214-66-9

4-phenyl-1-butylamine

C23H21N3O

C23H21N3O

Conditions
ConditionsYield
Stage #1: tubermycin B; 4-phenyl-1-butylamine With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 24h;
Stage #2: In dichloromethane; water; acetonitrile at 20℃; for 0.5h;		52.64%
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 24h;52.64%
tubermycin B
2538-68-3

tubermycin B

butan-1-ol
71-36-3

butan-1-ol

C17H16N2O2

C17H16N2O2

Conditions
ConditionsYield
Stage #1: tubermycin B With thionyl chloride In toluene at 80℃; for 2h;
Stage #2: butan-1-ol With triethylamine In dichloromethane at 20℃; for 12h;		52%
methanesulfonamide
3144-09-0

methanesulfonamide

tubermycin B
2538-68-3

tubermycin B

N-(methylsulfonyl)phenazine-1-carboxamide

N-(methylsulfonyl)phenazine-1-carboxamide

Conditions
ConditionsYield
Stage #1: tubermycin B With dmap; 1,1'-carbonyldiimidazole In dichloromethane; N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere;
Stage #2: methanesulfonamide With triethylamine In dichloromethane; N,N-dimethyl-formamide at 70℃; for 48h; Inert atmosphere;		40%
2-(acetylamino)ethanethiol
1190-73-4

2-(acetylamino)ethanethiol

tubermycin B
2538-68-3

tubermycin B

A

C17H15N3O3S

C17H15N3O3S

B

C17H15N3O3S

C17H15N3O3S

C

C17H15N3O3S

C17H15N3O3S

D

C17H15N3O3S

C17H15N3O3S

Conditions
ConditionsYield
In dimethyl sulfoxide for 24h; UV-irradiation; regioselective reaction;A 10%
B 8%
C 6%
D 5%
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid methyl ester
3225-19-2

phenazine-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With ethanol; acetone
In methanol; diethyl ether; chloroform
In diethyl ether for 2h; Ambient temperature;18.5 mg
In methanol at 20℃; Darkness;50 mg
tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxamide
550-89-0

phenazine-1-carboxamide

Conditions
ConditionsYield
With thionyl chloride und anschliessend Behandeln mit konz.wss.NH3;
Multi-step reaction with 2 steps
1: concentrated H2SO4
2: concentrated aqueous NH3
View Scheme
Multi-step reaction with 2 steps
1: methanol / 20 °C / Darkness
2: ammonia / methanol / 20 °C
View Scheme
tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid methyl ester
3225-19-2

phenazine-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride und Erwaermen des Reaktionsprodukts mit Methanol;
Multi-step reaction with 2 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Reflux
2: dichloromethane / 2.5 h / 0 - 5 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 °C / Reflux
2: triethylamine / dichloromethane / Reflux
View Scheme
tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid dimethylamide

phenazine-1-carboxylic acid dimethylamide

Conditions
ConditionsYield
With thionyl chloride und Behandeln des erhaltenen Saeurechlorids mit wss.Dimethylamin;
tubermycin B
2538-68-3

tubermycin B

phenazine-1-carboxylic acid-(2-diethylamino-ethyl ester); hydrochloride

phenazine-1-carboxylic acid-(2-diethylamino-ethyl ester); hydrochloride

Conditions
ConditionsYield
With thionyl chloride und Erwaermen des Reaktionsprodukts mit 2-Diaethylamino-aethanol in Benzol;
tubermycin B
2538-68-3

tubermycin B

5,10-dihydrophenazine-1-carboxylic acid
91822-73-0

5,10-dihydrophenazine-1-carboxylic acid

Conditions
ConditionsYield
With methanol; nickel Hydrogenation;
tubermycin B
2538-68-3

tubermycin B

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

Phenazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide
103942-97-8

Phenazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide
tubermycin B
2538-68-3

tubermycin B

N-<2-(4-aminophenoxy)ethyl>-3,4-dimethoxy-N-methylbenzenemethanamine
143666-91-5

N-<2-(4-aminophenoxy)ethyl>-3,4-dimethoxy-N-methylbenzenemethanamine

N-[4-(2-(Methylveratrylamino)ethoxy)phenyl]-1-phenazinecarboxamide

N-[4-(2-(Methylveratrylamino)ethoxy)phenyl]-1-phenazinecarboxamide

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide

1-Phenazinecarboxylic acid Specification

This chemical is called 1-Phenazinecarboxylic acid, and its systematic name is phenazine-1-carboxylic acid. With the molecular formula of C13H8N2O2, its molecular weight is 224.21. The CAS registry number of this chemical is 2538-68-3. Additionally, its classification codes are Drug / Therapeutic Agent; Natural Product. 

Other characteristics of the 1-Phenazinecarboxylic acid can be summarised as followings: (1)ACD/LogP: 2.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.05; (4)ACD/LogD (pH 7.4): -0.62; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.53; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 52.08 Å2; (13)Index of Refraction: 1.769; (14)Molar Refractivity: 65.05 cm3; (15)Molar Volume: 156.6 cm3; (16)Polarizability: 25.78×10-24cm3; (17)Surface Tension: 77.8 dyne/cm; (18)Density: 1.431 g/cm3; (19)Flash Point: 252.9 °C; (20)Enthalpy of Vaporization: 80.25 kJ/mol; (21)Boiling Point: 494.6 °C at 760 mmHg; (22)Vapour Pressure: 1.34E-10 mmHg at 25°C.

Production method of this chemical: The 1-Phenazinecarboxylic acid could be obtained by the reactant of phenazine-1-carbonitrile. This reaction needs the reagent of aq. H2SO4. The yield is 75 %. In addition, this reaction should be taken for 1 hour at the temperature of 140 °C. 

Uses of this chemical: The 1-Phenazinecarboxylic acid could react with methanol, and obtain the phenazine-1-carboxylic acid methyl ester. This reaction needs the reagent of H2SO4. The yield is 86 %.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(O)c2cccc1nc3c(nc12)cccc3
2.InChI: InChI=1/C13H8N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,(H,16,17)
3.InChIKey: JGCSKOVQDXEQHI-UHFFFAOYAS

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   Antibiotiki. Vol. 26, Pg. 135, 1981.
Link to PubMed
mouse LD50 intravenous 400mg/kg (400mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 143, 1981.

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