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Basic Information
CAS No.: 10537-47-0
Name: TYRPHOSTIN A9
Article Data: 7
Molecular Structure:
Molecular Structure of 10537-47-0 (TYRPHOSTIN A9)
Formula: C18H22 N2 O
Molecular Weight: 282.385
Synonyms: Malononitrile,(3,5-di-tert-butyl-4-hydroxybenzylidene)- (6CI,7CI,8CI);Propanedinitrile,[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]- (9CI);2,6-Di-tert-butyl-4-(2,2-dicyanovinyl)phenol;3,5-di-tert-Butyl-4-hydroxybenzylidenemalonitrile;3,5-di-tert-Butyl-4-hydroxybenzylidenemalononitrile;AG 17;GCP 5126;Malonoben;NSC 242557;RG 50872;SF 6847;Tyrphostin 9;Tyrphostin A 9;Tyrphostin AG 17;
Density: 1.064 g/cm3
Melting Point: 141-143℃ (ethanol )
Boiling Point: 386.8 ºCat 760 mmHg
Flash Point: 187.7 ºC
Solubility: ethanol: 20 mg/mL
Appearance: solid yellow
Hazard Symbols: ToxicT
Risk Codes: 23/24/25
Safety: Poison by ingestion and skin contact. See also NITRILES. When heated to decomposition it emits toxic fumes of NOx and CN.
PSA: 67.81000
LogP: 4.41776
Synthetic route
109-77-3

malononitrile

1620-98-0

3,5-di-t-butyl-4-hydroxybenzaldehyde

10537-47-0

malonoben

Conditions
ConditionsYield
With ammonium acetate In ethanol at 50 - 80℃;95%
In N,N-dimethyl-formamide for 10h; Knoevenagel reaction; Heating;83%
With piperidine In ethanol at 50 - 60℃; for 4h;75.7%
6125-26-4

phenyl(2-phenyl-2,3-dihydrobenzo[d]thiazol-2-yl)methanone

10537-47-0

malonoben

2-(1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2-phenylethyl)malononitrile

Conditions
ConditionsYield
With sodium dihydrogenphosphate; 1-hydroxy-1,2-benzodioxol-3-(1H)-one In dichloromethane at 20℃; for 8h; Inert atmosphere; Irradiation;88%
10537-47-0

malonoben

2001-95-8

valinomycin

83746-99-0

C54H90N6O18*C18H21N2O(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 0.166667h;
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  • 10537-47-0  CAS NO.10537-47-0

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    10537-47-0 CAS NO.10537-47-0

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Chemistry

Molecular Structure of Malonoben (CAS NO. 10537-47-0):

IUPAC Name: 2-[(3,5-Ditert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile 
Molecular Formula: C18H22N2O
Molecular Weight: 282.380080 g/mol
XLogP3-AA: 5
H-Bond Donor: 1
H-Bond Acceptor: 3
Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=C(C#N)C#N
InChI: InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3
InChIKey: MZOPWQKISXCCTP-UHFFFAOYSA-N
Appearance: yellow solid
Index of Refraction: 1.554
Molar Refractivity: 85.1 cm3
Molar Volume: 265.2 cm3
Surface Tension: 41.6 dyne/cm
Density: 1.064 g/cm3
Flash Point: 187.7 °C
Enthalpy of Vaporization: 66.06 kJ/mol
Boiling Point: 386.8 °C at 760 mmHg
Vapour Pressure: 1.55E-06 mmHg at 25 °C
Ethanol Solubility: 20 mg/mL
Water Solubility: 3.742 mg/L at 25 °C

Toxicity Data With Reference

1.    

orl-rat LD50:87 mg/kg

    SPEADM    Special Publication of the Entomological Society of America. 78-1 (1978),21.
2.    

skn-rbt LD50:226 mg/kg

    SPEADM    Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740) 74-1 ,1974.

Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List.

Safety Profile

Safety Information of Malonoben (CAS NO. 10537-47-0):
Hazard Codes: T Toxic
Risk Statements: 23/24/25
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed
Safety Statements: 36/37/39-45
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: OO3737000
Poison by ingestion and skin contact. See also NITRILES. When heated to decomposition it emits toxic fumes of NOx and CN.

Specification

  Malonoben with cas registry number of 10537-47-0 is acaricide, called for (3,5-Di-t-butyl-4-hydroxybenzylidene)malononitrile ; 2-((3,5-Bis(1,1-dimethyl)-4-hydroxyphenyl)methylene)propanedinitrile ; 2-((3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl)methylene)propanedinitrile ; 4-10-00-02178 (Beilstein Handbook Reference) ; AI3-27910 ; Caswell No. 291AA ; ENT 27910 ; EPA Pesticide Chemical Code 537200 ; GCP 5126 ; Gulf S-15126 ; Malonoben [ANSI] ; Malononitrile, 3,5-di-tert-butyl-4-hydroxybenzylidene- ; Malononitrile, (3,5-di-tert-butyl-4-hydroxybenzylidene)- (8CI) ; NSC 242557 ; Propanedinitrile, ((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene)- ; Propanedinitrile, 2-((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene)- ; S-15126 ; SF 6847 ; Tyrphostin A9 . It is obtained by condensation of Malononitrile and 3,5-t-Butyl-4-hydroxybenzaldehyde .