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3734-33-6

Basic Information
CAS No.: 3734-33-6
Name: Denatonium benzoate
Molecular Structure:
Molecular Structure of 3734-33-6 (Denatonium benzoate)
Formula: C28H34N2O3
Molecular Weight: 446.59
Synonyms: Denatonii benzoas [INN-Latin];N-(2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme- thanaminium benzoate;Benzyldiethyl((2,6-xylylcarbamoyl)methyl)ammonium benzoate;benzoic acid; benzyl-[(2,6-dimethylphenyl)carbamoylmethyl]-diethyl-azanium;EPA Pesticide Chemical Code 009106;((2,6-Xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate;Benzoato de denatonio [INN-Spanish];Benzoate de denatonium [INN-French];Anispray;Lidocaine benzyl benzoate;Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate;Benzenemethan-aminium, n-(2-((2,6-dimethylphenyl)amino)-2-oxo-ethyl)-n,n-diethyl-, benzoate;benzyl-[(2,6-dimethylphenyl)carbamoylmethyl]-diethyl-azanium benzoate;Ammonium, benzyldiethyl[ (2,6-xylylcarbamoyl)methyl]-, benzoate;
EINECS: 223-095-2
Density: 1.1256 (rough estimate)
Melting Point: 164-168 °C(lit.)
Boiling Point: 555.91°C (rough estimate)
Flash Point: 100℃
Solubility: methanol: 50 mg/mL, clear, colorless
Appearance: white crystals
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38-20/21/22
Safety: 26-36-37/39
PSA: 69.23000
LogP: 4.42180
Synthetic route

denatonium hydroxide

65-85-0

benzoic acid

3734-33-6

denatonium benzoate

Conditions
ConditionsYield
In acetone at 30 - 35℃; for 2.5h;80.52%
3734-33-6

denatonium benzoate

A

137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

B

2-diethylamino-N-(2,6-dimethyl-phenyl)-3-phenyl-propionamide

Conditions
ConditionsYield
at 250℃;
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  • Denatonium Benzoate Anhydrous CAS 3734-33-6

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    Denatonium Benzoate Anhydrous CAS 3734-33-6

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  • Denatonium Benzoate

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    Denatonium Benzoate

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Chemistry

Molecular Structure of Denatonium benzoate (CAS NO.3734-33-6):

IUPAC Name: benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate
Empirical Formula: C28H34N2O3
Molecular Weight: 446.5812 
ACD/LogP: 0.09
of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 0.08
ACD/LogD (pH 7.4): 0.08
ACD/BCF (pH 5.5): 1
ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 26.49
ACD/KOC (pH 7.4): 26.49
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 7
Polar Surface Area: 20.31 Å2
InChI
InChI=1/C21H28N2O.C7H6O2/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;8-7(9)6-4-2-1-3-5-6/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9)
Smiles
c1(C[N+](CC(Nc2c(cccc2C)C)=O)(CC)CC)ccccc1.c1cccc(c1)C([O-])=O
EINECS: 223-095-2 
Melting point: 164-168 °C(lit.)
Solubility methanol: 50 mg/mL, clear, colorless
Merck: 2891
Stability: Stable. Incompatible with strong oxidizing agents.
Product Categories: Miscellaneous Biochemicals;Ammonium Polyhalides, etc. (Quaternary);Quaternary Ammonium Compounds 

History

 Since 1995, when the State of Oregon required that denatonium benzoate be added to antifreeze and windshield wiper fluid, the compound has been increasingly found in these substances throughout the world. The addition is credited with saving children and animals who might otherwise drink sweet antifreeze or wiper fluid and get ethylene glycol or methanol poisoning respectively.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 oral 508mg/kg (508mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. PB81-139339,
rat LD50 oral 584mg/kg (584mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. PB81-139339,

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-20/21/22
R22:Harmful if swallowed. 
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: 2
RTECS: BO6650000
HS Code: 29242995

Specification

  Denatonium benzoate , with CAS number of 3734-33-6, can be called N,N-Diethyl-n-[(2,6-dimethylphenylcar-bamoyl)methyl]benzylammonium benzoate ; N-[2-[(2,6-Dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-benzenemethanaminium benzoate ; Rejexit (r) ; benzoate ; Benzenemethanaminium,N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-,benzoate ; benzyldiethyl((2,6-xylylcarbamoyl)methyl)-ammoniubenzoate ; denatonium ; denatoniumbenzoate,anhydrous . It is a white crystal.

  Denatonium benzoate (CAS NO.3734-33-6) are usually colorless and odorless solids but are often traded as solutions.The bitterness of the compound guides most applications of denatonium. Denatonium benzoate is used to denature ethanol so that it is not taxed as an alcoholic beverage. One designation in particular, SD-40B, indicates that ethanol has been denatured using denatonium benzoate. The common name for this chemical, denatonium, alludes to this application. So far ,we know that Denatonium usually available as denatonium benzoate (under trade names such as Bitrex or Aversion) and as denatonium saccharide.And it is the most bitter chemical compound .They are used as aversive agents to prevent accidental ingestion. Denatonium is used in denatured alcohol,antifreeze, nail biting preventions, animal repellents, liquid soaps, and shampoos. It is not known to pose any long-term health risks.