Proflavine supplier | CasNO.92-62-6

Name
PROFLAVINE
EINECS 202-172-4 (Proflavine)
CAS No. 92-62-6
Article Data16
CAS DataBase
Density 1.346 g/cm³
Solubility Slightly soluble SOLVENT

Melting Point 260 C

Formula C13H11 N3

Boiling Point 506.9 °C at 760 mmHg

Molecular Weight 209.25

Flash Point 292.9 °C

Transport Information 307

Appearance orange to brown powder

Safety Poison by intravenous, intraperitoneal, and subcutaneous routes. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also 2,6-DIAMINOACRIDINE; 3,6-DIAMINOACRIDINE HYDROCHLORIDE HEMIHYDRATE; 3,6-DIAMINOACRIDINE SULFATE (1:1).

Risk Codes

Molecular Structure

Hazard Symbols 9 (Packing Group: III) UN NO.

Synonyms Acridine,3,6-diamino- (8CI); 3,6-Diaminoacridine; 3,7-Diamino-5-azaanthracene; Isoflavbase; Proflavin; Proflavine

PSA 64.93000

LogP 3.71480

Synthetic route

64-18-6
formic acid

541-69-5
m-phenylenediamine dihydrochloride

A

92-62-6
proflavine

B

9,10-dihydro-9,9'-oxy-bis-acridine-3,6-diyldiamine

Conditions

Conditions Yield

With glycerol at 155℃;

...Expand

42832-87-1
3,6-diaminoacridin-9(10H)-one

92-62-6
proflavine

Conditions

Conditions Yield

With sodium hydroxide; sodium amalgam; water

26946-33-8
4,4'-methylenebis(m-nitroaniline)

92-62-6
proflavine

Conditions

Conditions Yield

With hydrogenchloride; tin at 135 - 140℃;

181189-62-8
4,4'-methanediyl-bis-m-phenylenediamine

92-62-6
proflavine

Conditions

Conditions Yield

With hydrogenchloride at 170℃;

144-62-7
oxalic acid

108-45-2
m-phenylenediamine

5435-44-9, 22243-66-9
(E)-3-Ureido-but-2-enoic acid ethyl ester

56-81-5
glycerol

92-62-6
proflavine

Conditions

Conditions Yield

at 190℃;

...Expand

64-18-6
formic acid

108-45-2
m-phenylenediamine

5435-44-9, 22243-66-9
(E)-3-Ureido-but-2-enoic acid ethyl ester

56-81-5
glycerol

92-62-6
proflavine

Conditions

Conditions Yield

at 190℃;

...Expand

108-45-2
m-phenylenediamine

92-62-6
proflavine

Conditions

Conditions Yield

With oxalic acid; zinc(II) chloride at 190℃; Glycerin;

With formic acid; zinc(II) chloride at 190℃; Glycerin;

64-18-6
formic acid

541-69-5
m-phenylenediamine dihydrochloride

56-81-5
glycerol

A

92-62-6
proflavine

B

9,10-dihydro-9,9'-oxy-bis-acridine-3,6-diyldiamine

Conditions

Conditions Yield

at 155℃;

...Expand

6262-24-4
formic acid-(3-amino-anilide)

541-69-5
m-phenylenediamine dihydrochloride

5435-44-9, 22243-66-9
(E)-3-Ureido-but-2-enoic acid ethyl ester

56-81-5
glycerol

92-62-6
proflavine

Conditions

Conditions Yield

at 155℃;

...Expand

219853-08-4
(3,3'-bisamino)diphenylamine

56-81-5
glycerol

92-62-6
proflavine

Conditions

Conditions Yield

With hydrogenchloride; formic acid; water

2.2'-azo-4.4'-diamino-diphenylmethane

2.2'-azo-4.4'-diamino-diphenylmethane

92-62-6
proflavine

Conditions

Conditions Yield

With potassium hydroxide; zinc kurzes Kochen der angesaeuerten Reaktionsfluessigkeit;

2.2'-dinitro-4.4'-diamino-diphenylamine

2.2'-dinitro-4.4'-diamino-diphenylamine

92-62-6
proflavine

3.6-diamino-acridone

3.6-diamino-acridone

92-62-6
proflavine

Conditions

Conditions Yield

With sodium amalgam

101-22-4
N,N'-bis(3-aminophenyl)urea

hydrochloride of N,N'-bis-<3-formylamino-phenyl>-urea

hydrochloride of N,N'-bis-<3-formylamino-phenyl>-urea

92-62-6
proflavine

Conditions

Conditions Yield

With naphthalene at 140 - 190℃;

With glycerol at 140 - 190℃;

64-17-5
ethanol

42832-87-1
3,6-diaminoacridin-9(10H)-one

sodium amalgam

sodium amalgam

92-62-6
proflavine

...Expand

30504-51-9
11H-dibenzo[c,f][1,2]diazepine-3,8-diamine

zinc dust

zinc dust

diluted KOH-solution

diluted KOH-solution

92-62-6
proflavine

Conditions

Conditions Yield

kurzes Erwaermen der angesaeuerten Reaktionsfluessigkeit auf dem Wasserbad;

...Expand

101-77-9
4,4'-diamino diphenyl methane

92-62-6
proflavine

Conditions

Conditions Yield

Multi-step reaction with 2 steps
2: tin; HCl / 135 - 140 °C
View Scheme

952-23-8
proflavine hydrochloride

92-62-6
proflavine

Conditions

Conditions Yield

With sodium hydrogencarbonate In water at 40℃; pH=10;

248928-58-7
acridine orange

92-62-6
proflavine

Conditions

Conditions Yield

With zinc(II) oxide; squaraine; protoporphyrin IX In water for 1h; Reagent/catalyst; Irradiation;

92-62-6
proflavine

403-43-0
4-fluorobenzoyl chloride

4-fluoro-N-[6-(4-fluorobenzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With triethylamine In pyridine at 80℃; for 1h; Inert atmosphere; 96%

92-62-6
proflavine

541-41-3
chloroformic acid ethyl ester

503853-12-1
3,6-diethoxycarbonylaminoacridine

Conditions

Conditions Yield

With pyridine at 0 - 20℃; 95%

92-62-6
proflavine

625-36-5
2-chloropropionyl chloride

250256-09-8
3,6-bis(3-chloropropionamido)acridine

Conditions

Conditions Yield

for 2h; Acylation; Heating; 92%

for 3h; Neat (no solvent); Reflux; 90%

amidation; Heating;

92-62-6
proflavine

122-01-0
4-chloro-benzoyl chloride

4-chloro-N-[6-(4-chlorobenzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With triethylamine In pyridine at 80℃; for 1h; Inert atmosphere; 90%

92-62-6
proflavine

N-ethyl-N-ethoxyl aniline

3,6-di-(N-ethyl-N-ethoxyl phenylazo) acridine

Conditions

Conditions Yield

Stage #1: proflavine With hydrogenchloride; sodium nitrite at 0℃; for 0.5h; pH=1 - 2;
Stage #2: N-ethyl-N-ethoxyl aniline In aq. phosphate buffer at 0 - 5℃; for 2h; 89.2%

92-62-6
proflavine

16182-04-0
Ethoxycarbonyl isothiocyanate

1071816-89-1
3,6-bis[3-(ethoxycarbonyl)thioureido]acridine

Conditions

Conditions Yield

In N,N-dimethyl-formamide at 60℃; for 4h; 86%

In N,N-dimethyl-formamide at 60℃; for 4h; 86%

92-62-6
proflavine

879-18-5
naphthalene-1-carbonic acid chloride

1160799-63-2
N-[6-(1-naphthamino)acridin-3-yl]-1-naphthamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 20℃; for 15h; Inert atmosphere; 86%

92-62-6
proflavine

100-07-2
4-methoxy-benzoyl chloride

4-methoxy-N-[6-(4-methoxybenzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 85%

92-62-6
proflavine

108-24-7
acetic anhydride

74165-99-4
3-(acetylamino)-6-aminoacridine

Conditions

Conditions Yield

In propionic acid at -12℃; 84%

83%

In propionic acid at -20℃; for 10h; 83%

92-62-6
proflavine

3024-72-4
3,4-dichlorobenzoyl chloride

1160799-58-5
3,4-dichloro-N-[6-(3,4-dichlorobenzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 84%

92-62-6
proflavine

874-60-2
4-methyl-benzoyl chloride

4-methyl-N-[6-(4-methylbenzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With triethylamine In pyridine at 80℃; for 1h; Inert atmosphere; 82%

92-62-6
proflavine

79-04-9
chloroacetyl chloride

51462-38-5
N,N’-(2-chloroacetamidyl)-3,6-acridine

Conditions

Conditions Yield

Stage #1: proflavine With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: chloroacetyl chloride In N,N-dimethyl-formamide at 0℃; for 3h; 79.7%

With triethylamine In N,N-dimethyl-formamide

92-62-6
proflavine

98-88-4
benzoyl chloride

N-[6-(benzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 79%

92-62-6
proflavine

71639-56-0
{(N,N,N',N'-tetramethylethylenediamine)Cl(η2-ethylene)platinum}ClO4

{(PtCl(CH3)4N2C2H4)2(HNC13H7(NHCH2CH2)2)}(1+)*ClO4(1-)={(C29H50Cl2N7Pt2)}ClO4

Conditions

Conditions Yield

In methanol; water byproducts: C13H12N3(1+); mixing Pt complex and proflavine in aq. methanol at room temp. (water-methanol 1/5 v/v); stirring, 48h;; filtration; washing with methanol; drying: Pt complex; evapn. filtered soln. to dryness: Pt complex together with monoprotonated proflavine; elem. anal.;; 75%

92-62-6
proflavine

24424-99-5
di-tert-butyl dicarbonate

180138-03-8
tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate

Conditions

Conditions Yield

In acetone at 20℃; for 72h; Inert atmosphere; 75%

92-62-6
proflavine

3282-30-2
pivaloyl chloride

1160799-57-4
N-[6-(pivalamino)acridin-3-yl]pivalamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 74%

92-62-6
proflavine

322474-21-5
N,N'-bis-Boc-S-methyl-isothiourea

3,6-bis(N',N''-di-Boc-guanidino)acridine

Conditions

Conditions Yield

With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; 73%

With silver nitrate; triethylamine In dichloromethane at 20℃; Inert atmosphere; 34%

92-62-6
proflavine

24424-99-5
di-tert-butyl dicarbonate

A

180138-07-2
(6-amino-3-acridinyl)carbamic acid tert-butyl ester

B

180138-03-8
tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate

Conditions

Conditions Yield

In acetone for 72h; Heating; A 10%
B 72%

In acetone for 8h; Heating; A 59%
B 25%

In acetone for 8h; Heating; A 40%
B 7%

...Expand

92-62-6
proflavine

456-27-9
4-nitrobenzenediazonium tetrafluoroborate

195615-41-9
3,6-Diamino-4-(4-nitro-phenylazo)acridin

Conditions

Conditions Yield

In methanol; acetic acid for 1h; 70%

14368-49-1
p-nitrobenzenediazonium

92-62-6
proflavine

195615-41-9
3,6-Diamino-4-(4-nitro-phenylazo)acridin

Conditions

Conditions Yield

With sodium tetrafluoroborate In methanol at 0℃; 70%

527-69-5
2-furancarbonyl chloride

92-62-6
proflavine

1160799-65-4
N-[6-(furan-2-carboxamido)acridin-3-yl]furan-2-carboxamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 20℃; for 15h; Inert atmosphere; 70%

92-62-6
proflavine

79-22-1
methyl chloroformate

170302-10-0
methyl N-[6-(methoxycarbonylamino)acridin-3-yl]-carbamate

Conditions

Conditions Yield

With sodium hydrogencarbonate In acetone at 60℃; for 72h; 70%

With potassium carbonate In acetone for 72h; Reflux; 53%

92-62-6
proflavine

123-62-6
propionic acid anhydride

N-[6-(propionylamino)acridin-3-yl]propanamide

Conditions

Conditions Yield

With triethylamine In pyridine at 50 - 80℃; for 1h; Inert atmosphere; 65%

92-62-6
proflavine

64-19-7
acetic acid

26484-04-8
3,6-Bis(ethylamino)acridin

Conditions

Conditions Yield

With sodium tetrahydroborate 62%

92-62-6
proflavine

75-36-5
acetyl chloride

15724-70-6
3,6-diacetamido-acridine

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 60%

92-62-6
proflavine

122-04-3
4-nitro-benzoyl chloride

1160799-60-9
4-nitro-N-[6-(4-nitrobenzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 57%

92-62-6
proflavine

24424-99-5
di-tert-butyl dicarbonate

180138-07-2
(6-amino-3-acridinyl)carbamic acid tert-butyl ester

Conditions

Conditions Yield

In acetone 53%

In acetone for 24h; Reflux; 51%

591-50-4
iodobenzene

92-62-6
proflavine

N,N,N',N'-tetraphenyl-acridine-3,6-diamine

Conditions

Conditions Yield

With copper; potassium carbonate at 180℃; for 72h; Ullman reaction; 48%

92-62-6
proflavine

785-56-8
3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

1160799-59-6
3,5-di-(trifluoromethyl)-N-[6-(3,5-di-(trifluoromethyl)benzoylamino)acridin-3-yl]benzamide

Conditions

Conditions Yield

With potassium carbonate In acetone at 0 - 20℃; for 15h; Inert atmosphere; 47%

92-62-6
proflavine

108-24-7
acetic anhydride

15724-70-6
3,6-diacetamido-acridine

Conditions

Conditions Yield

With sodium acetate at 100℃; for 2h; 43%

With sodium acetate

at 80 - 135℃;

Proflavine Chemical Properties

Chemistry informtion about Proflavine (CAS NO.92-62-6) is:
IUPAC Name: Acridine-3,6-Diamine
Synonyms: Proflavine ; 3,6-Acridinediamine ; 3,6-Aiaminoacridine ; Isoflabase
MF: C₁₃H₁₁N₃
MW: 11209.2465
Density: 1.346 g/cm³
Flash Point: 292.9 °C
Boiling Point: 506.9 °C at 760 mmHg
Vapour Pressure: 2.14E-10 mmHg at 25°C
Enthalpy of Vaporization: 77.69 kJ/mol
Following is the molecular structure of Proflavine (CAS NO.92-62-6) is:

Proflavine Uses

3,6-Diaminoacridinium (CAS NO.92-62-6) has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic.

Proflavine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source

cat LDLo intravenous 11111ug/kg (11.111mg/kg) sense organs and special senses: other changes: olfaction sense organs and special senses: other: eye lungs, thorax, or respiration: other changes Lancet. Vol. 196, Pg. 838, 1919.

mouse LD50 intraperitoneal 50mg/kg (50mg/kg) Chemotherapy Vol. 16, Pg. 371, 1971.

mouse LD50 oral > 1gm/kg (1000mg/kg) Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975.

mouse LD50 subcutaneous 140mg/kg (140mg/kg) British Journal of Experimental Pathology. Vol. 28, Pg. 1, 1947.

Proflavine Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 (1980),p. 195.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Proflavine Safety Profile

Poison by intravenous, intraperitoneal, and subcutaneous routes. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also 2,6-DIAMINOACRIDINE; 3,6-DIAMINOACRIDINE HYDROCHLORIDE HEMIHYDRATE; 3,6-DIAMINOACRIDINE SULFATE (1:1).

Proflavine Specification

Proflavine (CAS NO.92-62-6), also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria. Proflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair-insertions and not substitutions. Proflavine absorbs strongly in the blue region at 445nm (in water at pH 7) with molar extinction coefficient of c. 40,000.

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Conditions	Yield
With oxalic acid; zinc(II) chloride at 190℃; Glycerin;
With formic acid; zinc(II) chloride at 190℃; Glycerin;

Conditions	Yield
With naphthalene at 140 - 190℃;
With glycerol at 140 - 190℃;

Conditions	Yield
for 2h; Acylation; Heating;	92%
for 3h; Neat (no solvent); Reflux;	90%
amidation; Heating;

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 4h;	86%
In N,N-dimethyl-formamide at 60℃; for 4h;	86%

Conditions	Yield
In propionic acid at -12℃;	84%
	83%
In propionic acid at -20℃; for 10h;	83%

Conditions	Yield
Stage #1: proflavine With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: chloroacetyl chloride In N,N-dimethyl-formamide at 0℃; for 3h;	79.7%
With triethylamine In N,N-dimethyl-formamide

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃;	73%
With silver nitrate; triethylamine In dichloromethane at 20℃; Inert atmosphere;	34%

Conditions	Yield
In acetone for 72h; Heating;	A 10% B 72%
In acetone for 8h; Heating;	A 59% B 25%
In acetone for 8h; Heating;	A 40% B 7%

Conditions	Yield
With sodium hydrogencarbonate In acetone at 60℃; for 72h;	70%
With potassium carbonate In acetone for 72h; Reflux;	53%

Conditions	Yield
With sodium acetate at 100℃; for 2h;	43%
With sodium acetate
at 80 - 135℃;

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intravenous	11111ug/kg (11.111mg/kg)	sense organs and special senses: other changes: olfaction sense organs and special senses: other: eye lungs, thorax, or respiration: other changes	Lancet. Vol. 196, Pg. 838, 1919.
mouse	LD50	intraperitoneal	50mg/kg (50mg/kg)		Chemotherapy Vol. 16, Pg. 371, 1971.
mouse	LD50	oral	> 1gm/kg (1000mg/kg)		Journal of Medicinal Chemistry. Vol. 18, Pg. 320, 1975.
mouse	LD50	subcutaneous	140mg/kg (140mg/kg)		British Journal of Experimental Pathology. Vol. 28, Pg. 1, 1947.

Product Name

PROFLAVINE

Synthetic route

Proflavine Chemical Properties

Proflavine Uses

Proflavine Toxicity Data With Reference

Proflavine Consensus Reports

Proflavine Safety Profile

Proflavine Specification

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