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4-Dimethylaminobenzoic acid

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Name

4-Dimethylaminobenzoic acid

EINECS 210-615-8
CAS No. 619-84-1 Density 1.18 g/cm3
PSA 40.54000 LogP 1.45080
Solubility Insoluble in water. Melting Point 241-243 °C (dec.)(lit.)
Formula C9H11NO2 Boiling Point 315.8 °C at 760 mmHg
Molecular Weight 165.192 Flash Point 144.8 °C
Transport Information N/A Appearance light grey powder
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 619-84-1 (4-Dimethylaminobenzoic acid) Hazard Symbols IrritantXi
Synonyms

N,N-Dimethyl-4-aminobenzoic acid;N,N-Dimethyl-p-aminobenzoic acid;p-Dimethylamino benzoic acid;p-N,N-(Dimethylamino)benzoic acid;4-Dimethylaminobenzoic acid;Benzoic acid, 4-(dimethylamino)-;Benzoic acid, p-(dimethylamino)-;NSC 16596;

Article Data 141

4-Dimethylaminobenzoic acid Synthetic route

1703-46-4

N,N-dimethyl-4-hydroxymethylaniline

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.035h;99.6%
With oxygen In acetonitrile at 20℃; for 7h; Catalytic behavior;96%
With tert.-butylhydroperoxide; copper(ll) bromide In water; acetonitrile at 20℃; for 22.5h; Inert atmosphere; chemoselective reaction;90%
66379-84-8

2,2,2-trichloro-1-[4-(dimethylamino)phenyl]ethan-1-ol

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In methanol for 10h;98%
5925-53-1

4-<4-(Dimethylamino)thiobenzoyl>morpholine

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide for 0.0166667h; microwave irradiation;97%
22636-68-6

allyl 4-(dimethylamino)benzoate

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide; mineral oil at 25℃; for 4h; Inert atmosphere;97%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 60℃; for 3h; Inert atmosphere;86%
100-10-7

4-dimethylamino-benzaldehyde

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With Co4HP2Mo15V3O62; N-(4-sulfonic acid)butyl triethylammonium tetrafluoroborate; dihydrogen peroxide In water at 20℃; for 3h; Green chemistry;95%
With tert.-butylhydroperoxide; copper(ll) bromide In water; acetonitrile at 20℃; for 4.5h; Inert atmosphere; chemoselective reaction;92%
With sodium chlorite In acetonitrile 1.) 10 deg C, 2 h, 2.) RT, 3 h;89%
124-38-9

carbon dioxide

586-77-6

4-bromo-N,N-dimethylaniline

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With C26H30B10Cl2P2Pd In toluene at 50℃; under 760.051 Torr; for 8h;90%
With [2,2]bipyridinyl; lithium chloride; cobalt(II) iodide; zinc In N,N-dimethyl-formamide; acetonitrile at 40℃; under 760.051 Torr; for 14h; Sealed tube;61%
With diethylzinc; palladium diacetate; tert-butyl XPhos In hexanes; N,N-dimethyl acetamide at 40℃; under 7600.51 Torr; Automated synthesizer;40%
Stage #1: 4-bromo-N,N-dimethylaniline With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h;
Stage #2: With [2,2]bipyridinyl; (-)-menthol In tetrahydrofuran; pentane Inert atmosphere;
Stage #3: carbon dioxide In tetrahydrofuran; pentane at 20℃; under 5171.62 Torr; for 0.0166667h; Flow reactor;
124-38-9

carbon dioxide

95752-87-7

5,5-dimethyl-2-(4-(N,N-dimethylamino)phenyl)-1,3,2-dioxaborinane

A

1202-25-1

methyl 4-(N,N-dimethylamino)benzoate

B

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;A 87%
B n/a
124-38-9

carbon dioxide

95752-87-7

5,5-dimethyl-2-(4-(N,N-dimethylamino)phenyl)-1,3,2-dioxaborinane

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-(N,N-dimethylamino)phenyl)-1,3,2-dioxaborinane With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;
84%
124-38-9

carbon dioxide

10541-83-0

N-methyl-p-aminobenzoic acid

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With phenylsilane In N,N-dimethyl acetamide at 60℃; for 4h; Reagent/catalyst; Sealed tube;84%
119072-55-8, 7188-38-7

tert-butylisonitrile

28611-39-4

4-(dimethylamino)benzene-boronic acid

619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
Stage #1: tert-butylisonitrile; 4-(dimethylamino)benzene-boronic acid With copper diacetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; Molecular sieve; Sealed tube;
Stage #2: With water In N,N-dimethyl-formamide Molecular sieve; Sealed tube;
83%

4-Dimethylaminobenzoic acid Chemical Properties

Chemical Name: 4-Dimethylaminobenzoic acid
IUPAC Name: 4-(Dimethylamino)benzoic acid
Synonyms of 4-(Dimethylamino)benzoic acid (CAS NO.619-84-1): EINECS 210-615-8 ; N,N-Dimethyl-4-aminobenzoic acid ; N,N-Dimethyl-p-aminobenzoic acid ; NSC 16596 ; p-Dimethylamino benzoic acid ; p-N,N-(Dimethylamino)benzoic acid ; 4-Dimethylaminobenzoic acid ; Benzoic acid, 4-(dimethylamino)- ; Benzoic acid, p-(dimethylamino)-
CAS NO: 619-84-1
Molecular Formula of 4-(Dimethylamino)benzoic acid (CAS NO.619-84-1): C9H11NO2
Molecular Weight: 165.1891
Molecular Structure:

Melting Point: 241-243 °C
ProductCategories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts ; Organic acids ; Absolute Configuration Determination (Exciton Chirality CD Method) ; Analytical Chemistry ; Enantiomer Excess & Absolute Configuration Determination ; Exciton Chirality CD Method (for Hydroxyl Groups) ; Aromatic Amino Acids ; Peptide Synthesis ; Unnatural Amino Acid Derivatives 
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.594
Molar Refractivity: 47.49 cm3
Molar Volume: 139.9 cm3
Surface Tension: 49.6 dyne/cm
Density of 4-(Dimethylamino)benzoic acid (CAS NO.619-84-1): 1.18 g/cm3
Flash Point: 144.8 °C
Enthalpy of Vaporization: 58.81 kJ/mol
Boiling Point: 315.8 °C at 760 mmHg
Vapour Pressure: 0.00018 mmHg at 25°C
Appearance: light grey powder
Stability: Stable but incompatible with strong oxidizing agents.

4-Dimethylaminobenzoic acid Uses

An important intermediate used as photosensitizer, paints and dyes

4-Dimethylaminobenzoic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04362,

4-Dimethylaminobenzoic acid Consensus Reports

Reported in EPA TSCA Inventory.

4-Dimethylaminobenzoic acid Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: DG8735000
HS Code: 29224995
Poison by intravenous route. When heated to decomposition it emits toxic vapors of NOx.

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