Product Name

  • Name

    Coumarin 120

  • EINECS 247-454-8
  • CAS No. 26093-31-2
  • Article Data141
  • CAS DataBase
  • Density 1.275 g/cm3
  • Solubility
  • Melting Point 223-226 °C(lit.)
  • Formula C10H9NO2
  • Boiling Point 378.3 °C at 760 mmHg
  • Molecular Weight 175.187
  • Flash Point 216.9 °C
  • Transport Information
  • Appearance Yellow powder.
  • Safety 26-36-37/39
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 26093-31-2 (Coumarin 120)
  • Hazard Symbols IrritantXi,HarmfulXn
  • Synonyms 7-Amino-4-methylcoumarin;7-Amino-4-methyl-2H-chromen-2-one;4-Methyl-7-aminocoumarin;
  • PSA 56.23000
  • LogP 2.26480

Synthetic route

ethyl acetoacetate
141-97-9

ethyl acetoacetate

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

Conditions
ConditionsYield
With zirconium(IV) phosphate at 110℃; for 0.166667h; Pechmann condensation; Microwave irradiation; chemoselective reaction;100%
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.583333h; Pechmann condensation reaction;98%
With tetrakis(actonitrile)copper(I) hexafluorophosphate at 25℃; for 0.166667h; Pechmann condensation; neat (no solvent);98%
(4-methyl-2-oxo-2H-1-benzopyran-7-yl)carbamic acid ethyl ester
58632-48-7

(4-methyl-2-oxo-2H-1-benzopyran-7-yl)carbamic acid ethyl ester

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 120℃; for 4h; Reflux;99%
With sulfuric acid; acetic acid for 5h; Reflux;88%
With sulfuric acid In acetic acid for 3h; Heating;82%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 0.45h; Catalytic behavior; Reagent/catalyst; Pechmann Condensation; Milling; Green chemistry;95%
7-azido-4-methyl-2H-chromen-2-one

7-azido-4-methyl-2H-chromen-2-one

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

Conditions
ConditionsYield
Stage #1: 7-azido-4-methyl-2H-chromen-2-one With 9-phenyl-9-phosphafluorene; phenylsilane In 1,4-dioxane at 101℃; for 16h; Staudinger reduction reaction; Inert atmosphere;
Stage #2: With water In 1,4-dioxane at 20℃; Staudinger reduction reaction; Inert atmosphere;		93%
With C27H34ClN2ORu(1+)*Cl(1-); sodium formate In aq. phosphate buffer at 37℃; for 24h; pH=7.4;91%
In cyclohexane Irradiation;14%
methyl N-(4-methyl-2-oxo-2H-chromen-7-yl)-carbamate
114415-25-7

methyl N-(4-methyl-2-oxo-2H-chromen-7-yl)-carbamate

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

Conditions
ConditionsYield
With potassium hydroxide at 80 - 90℃; for 0.333333h;83%
With potassium hydroxide In water at 80 - 90℃;83%
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide
ethyl acetoacetate
141-97-9

ethyl acetoacetate

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

7-hydroxy-4-methylquinolin-2(1H)-one
20513-71-7

7-hydroxy-4-methylquinolin-2(1H)-one

Conditions
ConditionsYield
With bismuth(III) chloride at 75℃; for 1h; Pechmann condensation;A 81%
B 9%
...Expand
4-bromo-3-hydroxy-aniline
55120-56-4

4-bromo-3-hydroxy-aniline

(Z)-ethyl-3-(4,4,5,5)-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate
448212-00-8

(Z)-ethyl-3-(4,4,5,5)-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique; Sealed tube;71%
7-diethylamino-4-methylcoumarin
91-44-1

7-diethylamino-4-methylcoumarin

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

4-methyl-7-ethylamino-2H-benzopyran-2-one
28821-18-3

4-methyl-7-ethylamino-2H-benzopyran-2-one

Conditions
ConditionsYield
With acetophenone In acetonitrile for 17h; Irradiation;A 13%
B 60%
With aluminium trichloride In acetonitrile for 20h; Heating;A 28 % Turnov.
B 38 % Turnov.
With air In water Quantum yield; Mechanism; Irradiation; other solvent, addition of β-cyclodextrin, addition of a sensitiser (sulphonated aluminium-phthalocyanine);
ethyl acetoacetate
141-97-9

ethyl acetoacetate

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

7-hydroxy-4-methylquinolin-2(1H)-one
20513-71-7

7-hydroxy-4-methylquinolin-2(1H)-one

C

5-hydroxy-4-methyl-2(1H)-quinolinone
131195-67-0

5-hydroxy-4-methyl-2(1H)-quinolinone

Conditions
ConditionsYield
at 150℃; for 20h;A 7%
B 55%
C 16%
...Expand
7-diethylamino-4-methylcoumarin
91-44-1

7-diethylamino-4-methylcoumarin

acrylonitrile
107-13-1

acrylonitrile

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

7-ethylaminocoumarin
71173-56-3

7-ethylaminocoumarin

1-endo-cyano-8b-methyl-6-diethylamino-1,2,2a,8b-tetrahydro-3H-cyclobutachromen-3-one
121983-26-4

1-endo-cyano-8b-methyl-6-diethylamino-1,2,2a,8b-tetrahydro-3H-cyclobutachromen-3-one

Conditions
ConditionsYield
In acetonitrile for 10h; Irradiation; Yields of byproduct given;A n/a
B n/a
C 49%
...Expand
7-diethylamino-4-methylcoumarin
91-44-1

7-diethylamino-4-methylcoumarin

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide
66611-72-1

N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide

C

4-methyl-7-ethylamino-2H-benzopyran-2-one
28821-18-3

4-methyl-7-ethylamino-2H-benzopyran-2-one

D

Conditions
ConditionsYield
In ethanol for 16h; Irradiation; Further byproducts given;A 45%
B 7%
C 20%
D 8%
...Expand
7-diethylamino-4-methylcoumarin

7-diethylamino-4-methylcoumarin

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

4-methyl-7-ethylamino-2H-benzopyran-2-one
28821-18-3

4-methyl-7-ethylamino-2H-benzopyran-2-one

C

N-(4-methyl-2-oxo-2H-chromen-7-yl)formamide
144900-79-8

N-(4-methyl-2-oxo-2H-chromen-7-yl)formamide

D

7-(N-ethylacetamido)-4-methylcoumarin

7-(N-ethylacetamido)-4-methylcoumarin

Conditions
ConditionsYield
In ethanol for 16h; Irradiation; Further byproducts given;A 45%
B 20%
C 5%
D 8%
...Expand
7-diethylamino-4-methylcoumarin
91-44-1

7-diethylamino-4-methylcoumarin

A

7-amino-4-methylcoumarin.
26093-31-2

7-amino-4-methylcoumarin.

B

4-methyl-7-ethylamino-2H-benzopyran-2-one
28821-18-3

4-methyl-7-ethylamino-2H-benzopyran-2-one

C

3-nitro-4-methyl-7-diethylamino-2H-benzopyran-2-one
118116-72-6

3-nitro-4-methyl-7-diethylamino-2H-benzopyran-2-one

Conditions
ConditionsYield
With acetic acid; sodium nitrite at 40 - 50℃; for 8h; Mechanism; Product distribution; other oxidizing agents (one-electron transfer) in other solvents;A n/a
B n/a
C 31%
...Expand

Coumarin 120 Chemical Properties

Molecule structure of 2H-1-Benzopyran-2-one, 7-amino-4-methyl- (CAS NO.26093-31-2):

IUPAC Name: 7-Amino-4-methylchromen-2-one 
Molecular Weight: 175.18396 g/mol
Molecular Formula: C10H9NO2 
Density: 1.275 g/cm3 
Melting Point: 223-226 °C(lit.)
Boiling Point: 378.3 °C at 760 mmHg 
Flash Point: 216.9 °C
Index of Refraction: 1.627
Molar Refractivity: 48.7 cm3
Molar Volume: 137.3 cm3
Polarizability: 19.3×10-24 cm3
Surface Tension: 52.5 dyne/cm 
Enthalpy of Vaporization: 62.61 kJ/mol
Vapour Pressure: 6.37E-06 mmHg at 25 °C 
Storage Temp.: 2-8 °C
Sensitive: light sensitive
XLogP3: 1.6
H-Bond Donor: 1
H-Bond Acceptor: 3
Tautomer Count: 7
Exact Mass: 175.063329
MonoIsotopic Mass: 175.063329
Topological Polar Surface Area: 52.3
Heavy Atom Count: 13
Complexity: 260
Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)N
InChI: InChI=1S/C10H9NO2/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3
InChIKey: GLNDAGDHSLMOKX-UHFFFAOYSA-N
EINECS: 247-454-8
Product Categories of 2H-1-Benzopyran-2-one, 7-amino-4-methyl- (CAS NO.26093-31-2): Coumarins; Other Reagents; Peptide; Labeling and Diagnostics Reagents

Coumarin 120 Safety Profile

Hazard Codes: IrritantXi, HarmfulXn
Risk Statements: 36/37/38-20/21/22 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant

Coumarin 120 Specification

 2H-1-Benzopyran-2-one, 7-amino-4-methyl- (CAS NO.26093-31-2) is also named as 7-Amino-4-methylcoumarin ; CCRIS 4961 ; Coumarin 120 ; Coumarin, 7-amino-4-methyl- ; NSC 45796 . 2H-1-Benzopyran-2-one, 7-amino-4-methyl- (CAS NO.26093-31-2) is light yellow beige powder.

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