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619-84-1 Usage

Chemical Properties

4-Dimethylaminobenzoic acid is light grey powder

Uses

Different sources of media describe the Uses of 619-84-1 differently. You can refer to the following data:
1. 4-(Dimethylamino)benzoic Acid is a substituted benzoic acid that acts as an inhibitor of ultraviolet mediated damage to skin. 4-(Dimethylamino)benzoic Acid is a biotransformation product of 2-ethylhe xyl 4-(N,N-dimethylamino)benzoate (EDP), a widely used UV filters in sunscreen cosmetics and other cosmetic products.
2. 4-Dimethylaminobenzoic acid a substituted benzoic acid that acts as an inhibitor of ultraviolet mediated damage to skin. It is a biotransformation product of 2-ethylhexyl 4- (N,N-dimethylaminobenzo)benzoate(EDP), a widely used UV filters in sunscreen cosmetics and other cosmetic products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1807, 1960 DOI: 10.1021/jo01080a035

Purification Methods

Crystallise the acid from EtOH/water. [Beilstein 14 IV 1164.]

Check Digit Verification of cas no

The CAS Registry Mumber 619-84-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 619-84:
(5*6)+(4*1)+(3*9)+(2*8)+(1*4)=81
81 % 10 = 1
So 619-84-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6H,1-2H3,(H,11,12)/p-1

619-84-1 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A14338)  4-Dimethylaminobenzoic acid, 98+%   

  • 619-84-1

  • 100g

  • 1041.0CNY

  • Detail
  • Alfa Aesar

  • (A14338)  4-Dimethylaminobenzoic acid, 98+%   

  • 619-84-1

  • 250g

  • 2399.0CNY

  • Detail
  • Alfa Aesar

  • (A14338)  4-Dimethylaminobenzoic acid, 98+%   

  • 619-84-1

  • 500g

  • 4456.0CNY

  • Detail
  • Aldrich

  • (D139459)  4-(Dimethylamino)benzoicacid  98%

  • 619-84-1

  • D139459-25G

  • 409.50CNY

  • Detail
  • Aldrich

  • (D139459)  4-(Dimethylamino)benzoicacid  98%

  • 619-84-1

  • D139459-100G

  • 1,134.90CNY

  • Detail
  • Aldrich

  • (275654)  4-(Dimethylamino)benzoicacid  90%, technical grade

  • 619-84-1

  • 275654-25G

  • 466.83CNY

  • Detail

619-84-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Dimethylaminobenzoic acid

1.2 Other means of identification

Product number -
Other names 4-(dimethylamino)benzoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:619-84-1 SDS

619-84-1Synthetic route

N,N-dimethyl-4-hydroxymethylaniline
1703-46-4

N,N-dimethyl-4-hydroxymethylaniline

p-N,N-dimethylaminobenzoic acid
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%
2,2,2-trichloro-1-[4-(dimethylamino)phenyl]ethan-1-ol
66379-84-8

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

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In methanol for 10h;98%
4-<4-(Dimethylamino)thiobenzoyl>morpholine
5925-53-1

4-<4-(Dimethylamino)thiobenzoyl>morpholine

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide for 0.0166667h; microwave irradiation;97%
allyl 4-(dimethylamino)benzoate
22636-68-6

allyl 4-(dimethylamino)benzoate

p-N,N-dimethylaminobenzoic acid
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%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

p-N,N-dimethylaminobenzoic acid
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%
carbon dioxide
124-38-9

carbon dioxide

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

p-N,N-dimethylaminobenzoic acid
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;
carbon dioxide
124-38-9

carbon dioxide

5,5-dimethyl-2-(4-(N,N-dimethylamino)phenyl)-1,3,2-dioxaborinane
95752-87-7

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

A

methyl 4-(N,N-dimethylamino)benzoate
1202-25-1

methyl 4-(N,N-dimethylamino)benzoate

B

p-N,N-dimethylaminobenzoic acid
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
carbon dioxide
124-38-9

carbon dioxide

5,5-dimethyl-2-(4-(N,N-dimethylamino)phenyl)-1,3,2-dioxaborinane
95752-87-7

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

p-N,N-dimethylaminobenzoic acid
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%
carbon dioxide
124-38-9

carbon dioxide

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

p-N,N-dimethylaminobenzoic 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%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-(dimethylamino)benzene-boronic acid
28611-39-4

4-(dimethylamino)benzene-boronic acid

p-N,N-dimethylaminobenzoic 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%
carbon dioxide
124-38-9

carbon dioxide

4-(dimethylamino)benzene-boronic acid
28611-39-4

4-(dimethylamino)benzene-boronic acid

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube;78%
ethyl p-dimethyaminolbenzoate
10287-53-3

ethyl p-dimethyaminolbenzoate

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
Stage #1: ethyl p-dimethyaminolbenzoate With iron(III) chloride In tetrachloromethane at 85℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrachloromethane Inert atmosphere;
77%
With sodium hydroxide In ethanol at 85℃; for 6h;
methyl 4-(N,N-dimethylamino)benzoate
1202-25-1

methyl 4-(N,N-dimethylamino)benzoate

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;77%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

N-methyl-p-aminobenzoic acid
10541-83-0

N-methyl-p-aminobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sodium-exchanged Y-zeolite at 130℃; for 9h;A 74%
B n/a
carbon dioxide
124-38-9

carbon dioxide

4-N,N-dimethylaminophenyl magnesium chloride
108949-55-9

4-N,N-dimethylaminophenyl magnesium chloride

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
In tetrahydrofuran at 1℃; for 0.0833333h;72%
carbon dioxide
124-38-9

carbon dioxide

4-dimethylaminophenylmagnesium bromide
7353-91-5

4-dimethylaminophenylmagnesium bromide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
In tetrahydrofuran at 1℃; for 0.0833333h;71%
Methyl formate
107-31-3

Methyl formate

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

A

4-formamidobenzoic acid
28533-43-9

4-formamidobenzoic acid

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With potassium hydroxide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; dodecacarbonyl-triangulo-triruthenium; cetyltrimethylammonim bromide at 160℃; for 10h;A 58.2%
B 7%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In water at 140℃; for 10h;54%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

diethyl malonate
105-53-3

diethyl malonate

A

diethyl p-(N,N'-dimethylamino)-benzylidenemalonate
3435-56-1

diethyl p-(N,N'-dimethylamino)-benzylidenemalonate

B

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With bentonite Actisil FF for 0.25h; Irradiation;A 48%
B 3%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In water at 140℃; for 10h;48%
p-(1,3-dithiolan-2-yl)-N,N-dimethylaniline
31362-12-6

p-(1,3-dithiolan-2-yl)-N,N-dimethylaniline

A

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

B

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;A 18%
B 44%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In water at 140℃; for 10h;35%
carbon monoxide
201230-82-2

carbon monoxide

4-(dimethylamino)benzenediazonium tetrafluoroborate
24564-52-1

4-(dimethylamino)benzenediazonium tetrafluoroborate

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With water at 100℃; under 795063 Torr; for 2.5h;4.63%
1,4-dioxane
123-91-1

1,4-dioxane

potassium tert-butylate
865-47-4

potassium tert-butylate

bis(p-dimethylaminophenyl)methanone
90-94-8

bis(p-dimethylaminophenyl)methanone

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-(dimethylamino)benzoyl chloride
4755-50-4

4-(dimethylamino)benzoyl chloride

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With water
Multi-step reaction with 3 steps
1: triethylamine / diethyl ether
2: hydrogenchloride / water; acetonitrile
3: water; dimethyl sulfoxide / 25 °C
View Scheme
4-chloro-N,N-dimethylaniline
698-69-1

4-chloro-N,N-dimethylaniline

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 0.5 h / 200 °C / microwave irradiation
2: 72 percent / tetrahydrofuran / 0.08 h / 1 °C
View Scheme
With carbon dioxide; sodium; benzene
4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With n-butyllithium; diethyl ether anschliessend Behandeln mit Kohlendioxid;
With sodium; benzene anschliessend Behandeln mit Kohlendioxid;
2-(4-(dimethylamino)phenyl)-2-oxoacetic acid
63756-72-9

2-(4-(dimethylamino)phenyl)-2-oxoacetic acid

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

Conditions
ConditionsYield
With sulfuric acid at 120℃;
5-[(5-amino-2-methylbenzoylamino)-methyl]-7H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester
1616689-60-1

5-[(5-amino-2-methylbenzoylamino)-methyl]-7H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

5-{[5-(4-dimethylaminobenzoylamino)-2-methylbenzoylamino]-methyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester
1616688-96-0

5-{[5-(4-dimethylaminobenzoylamino)-2-methylbenzoylamino]-methyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h;4%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

1-(4-aminophenyl)cyclopentane-1-carbonitrile
115279-73-7

1-(4-aminophenyl)cyclopentane-1-carbonitrile

N-[4-(1-cyano-cyclopentyl)-phenyl]-4-dimethylamino-benzamide
1067189-46-1

N-[4-(1-cyano-cyclopentyl)-phenyl]-4-dimethylamino-benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 20℃; for 72h;5%
2-hydroxy-3-aminopyridine
33630-99-8

2-hydroxy-3-aminopyridine

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

N,N-dimethyl-4-oxazolo[5,4-b]pyridin-2-yl-aniline
52334-21-1

N,N-dimethyl-4-oxazolo[5,4-b]pyridin-2-yl-aniline

Conditions
ConditionsYield
With polystyrene triphenylphosphine; trichloroacetonitrile In acetonitrile at 150℃; for 0.25h; Microwave;6.6%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

descarboethoxyloratadine
100643-71-8

descarboethoxyloratadine

[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-(4-dimethylamino-phenyl)-methanone

[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-(4-dimethylamino-phenyl)-methanone

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 4℃; for 0.5h;11%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

2-(4-Dimethylaminophenyl)-5,6,7,8-tetrahydro-4H-thiazolo [5,4-b]azepine

2-(4-Dimethylaminophenyl)-5,6,7,8-tetrahydro-4H-thiazolo [5,4-b]azepine

Conditions
ConditionsYield
11.5%
N,N-diisopropylethylamine (DIPEA)

N,N-diisopropylethylamine (DIPEA)

2-(1H-benzotriazole-1-yl)-1,1,3,3-teramethyluronium tetrafluoroborate (TBTU)

2-(1H-benzotriazole-1-yl)-1,1,3,3-teramethyluronium tetrafluoroborate (TBTU)

quinoclamine
2797-51-5

quinoclamine

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

CAY 10398

CAY 10398

Conditions
ConditionsYield
With hydroxylamine In 1-Methylpyrrolidine; 1,4-dioxane; methanol; dichloromethane; water12%
2-(N-(4-sulfamoylphenyl)sulfamoyl)ethanamine hydrochloride

2-(N-(4-sulfamoylphenyl)sulfamoyl)ethanamine hydrochloride

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-dimethylamino-N-(2-(N-(4-sulfamoylphenyl)sulfamoyl)ethyl)benzamide

4-dimethylamino-N-(2-(N-(4-sulfamoylphenyl)sulfamoyl)ethyl)benzamide

Conditions
ConditionsYield
Stage #1: p-N,N-dimethylaminobenzoic acid With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In acetonitrile at 20℃;
Stage #2: 2-(N-(4-sulfamoylphenyl)sulfamoyl)ethanamine hydrochloride In water; acetonitrile
12%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

(2R,3R,4R,5R)-2-(aminomethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
194288-65-8

(2R,3R,4R,5R)-2-(aminomethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

1-(4-dimethylamino)benzoylamino-1,2,5-trideoxy-2,5-imino-D-mannitol

1-(4-dimethylamino)benzoylamino-1,2,5-trideoxy-2,5-imino-D-mannitol

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 25℃; for 4.5h;16%
p-Anisidinothioformyl-hydrazin
40207-03-2

p-Anisidinothioformyl-hydrazin

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

5-(4-(dimethylamino)phenyl)-N-(4-methoxyphenyl)-1,3,4-oxadiazol-2-amine
1257257-06-9

5-(4-(dimethylamino)phenyl)-N-(4-methoxyphenyl)-1,3,4-oxadiazol-2-amine

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;16%
n-vinylformamide
13162-05-5

n-vinylformamide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

6-(dimethylamino)-2H-isoquinolin-1-one

6-(dimethylamino)-2H-isoquinolin-1-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; potassium hydrogencarbonate In benzonitrile at 80℃; for 24h; Schlenk technique;16%
4-(p-chlorophenyl)-3-thiosemicarbazide
22814-92-2

4-(p-chlorophenyl)-3-thiosemicarbazide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

N-(4-chlorophenyl)-5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazol-2-amine
1257256-88-4

N-(4-chlorophenyl)-5-(4-(dimethylamino)phenyl)-1,3,4-oxadiazol-2-amine

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;19%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

9-<(4-dimethylamino)phenyl>-10-phenylacridinium phosphate

9-<(4-dimethylamino)phenyl>-10-phenylacridinium phosphate

Conditions
ConditionsYield
With PPA at 195℃; for 0.25h;20%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

N1-(4-methoxybenzoyl)-1,2-benzenediamine
103517-57-3

N1-(4-methoxybenzoyl)-1,2-benzenediamine

C23H23N3O3

C23H23N3O3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h; Acylation;20%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

tetramethylammonium 4-(dimethylamino)benzoate
70697-58-4

tetramethylammonium 4-(dimethylamino)benzoate

Conditions
ConditionsYield
In methanol20%
6-[4-(pyridin-2-yl)piperazin-1-yl]pyridazin-3-amine

6-[4-(pyridin-2-yl)piperazin-1-yl]pyridazin-3-amine

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-(dimethylamino)-N-[6-[4-(2-pyridyl)piperazin-1-yl]pyridazin-3-yl]benzamide

4-(dimethylamino)-N-[6-[4-(2-pyridyl)piperazin-1-yl]pyridazin-3-yl]benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h;20%
2-(hydroxymethyl)-3-methylbenzofuran
55581-62-9

2-(hydroxymethyl)-3-methylbenzofuran

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

2-<4-(Dimethylamino)phenylcarbonyloxymethyl>-3-methylbenzofuran
128753-78-6

2-<4-(Dimethylamino)phenylcarbonyloxymethyl>-3-methylbenzofuran

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 3h; Ambient temperature;22%
4-Chlorobenzenesulfonamide
98-64-6

4-Chlorobenzenesulfonamide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-chloro-N-(4-dimethylamino-benzoyl)-benzenesulfonamide

4-chloro-N-(4-dimethylamino-benzoyl)-benzenesulfonamide

Conditions
ConditionsYield
With dmap; N'-methyl polystyrene HL; N-cyclohexylcarbodiimide In dichloromethane at 20℃; for 72h;22%
C18H28O5
1447817-00-6

C18H28O5

C18H31NO4
1447817-02-8

C18H31NO4

isocyanoacetic acid methyl ester
39687-95-1

isocyanoacetic acid methyl ester

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

C49H73N3O12

C49H73N3O12

Conditions
ConditionsYield
Stage #1: C18H28O5; C18H31NO4; p-N,N-dimethylaminobenzoic acid In methanol at 20℃; for 0.5h; Ugi Condensation;
Stage #2: isocyanoacetic acid methyl ester With Ugi Condensation In methanol
22%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-(dimethylamino)benzoyl fluoride
108168-59-8

4-(dimethylamino)benzoyl fluoride

Conditions
ConditionsYield
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h; Schlenk technique; Inert atmosphere;22%
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / dichloromethane / 0.28 h / 0 - 20 °C / Sealed tube
2: triethylamine tris(hydrogen fluoride) / 2 h / 20 °C
View Scheme
With potassium fluoride; Tetrafluorophthalonitrile In acetonitrile at 80 - 90℃; under 760.051 Torr; for 24h; Temperature; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;85 %Spectr.
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 20℃; for 3h; Inert atmosphere;
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

3-(methyl-d3)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

3-(methyl-d3)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

methyl-d3 4-(dimethylamino)benzoate

methyl-d3 4-(dimethylamino)benzoate

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water-d2 at 60℃; for 6h; Sealed tube;23%
3-(4-aminomethylphenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol
1002299-79-7

3-(4-aminomethylphenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-Dimethylamino-N-[4-(5-hydroxy-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-benzyl]-benzamide

4-Dimethylamino-N-[4-(5-hydroxy-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-benzyl]-benzamide

Conditions
ConditionsYield
Stage #1: 3-(4-aminomethylphenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol; p-N,N-dimethylaminobenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 16h;
Stage #2: With ammonium chloride In dichloromethane; water; N,N-dimethyl-formamide
24%
N-(2-tert-butylphenyl)acetamide
7402-70-2

N-(2-tert-butylphenyl)acetamide

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

(RS)-N-(2-t-butylphenyl)-N-(4-dimethylaminobenzoyl)acetamide

(RS)-N-(2-t-butylphenyl)-N-(4-dimethylaminobenzoyl)acetamide

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine In dichloromethane at 25℃; for 2.5h;28%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

C9H3(2)H8NO2

C9H3(2)H8NO2

Conditions
ConditionsYield
With sodium borodeuteride; palladium 10% on activated carbon; water-d2 at 150℃; sealed tube; Microwave irradiation; Inert atmosphere;29%
(9H-fluoren-9-yl)methyl (4-((2,3-diaminopyridin-4-yl)oxy)phenyl)carbamate
1380678-11-4

(9H-fluoren-9-yl)methyl (4-((2,3-diaminopyridin-4-yl)oxy)phenyl)carbamate

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

4-(7-(4-aminophenoxy)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline
1380678-37-4

4-(7-(4-aminophenoxy)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline

Conditions
ConditionsYield
With polyphosphoric acid at 250℃; for 4h;30%
4-n-chlorophenylacetylene
873-73-4

4-n-chlorophenylacetylene

(py)CuIII(CF3)3

(py)CuIII(CF3)3

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

C18H15ClF3NO2

C18H15ClF3NO2

Conditions
ConditionsYield
Stage #1: p-N,N-dimethylaminobenzoic acid With sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 0.75h; Schlenk technique; Inert atmosphere;
Stage #2: 4-n-chlorophenylacetylene; (py)CuIII(CF3)3 In N,N-dimethyl-formamide at 100℃; for 12h; Schlenk technique; Inert atmosphere; stereoselective reaction;
30%
C57H72IrN9O3

C57H72IrN9O3

p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

C84H99IrN12O6

C84H99IrN12O6

Conditions
ConditionsYield
Stage #1: p-N,N-dimethylaminobenzoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: C57H72IrN9O3 In N,N-dimethyl-formamide at 20℃; for 12h;
34%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

methyl iodide
74-88-4

methyl iodide

(4-carboxyphenyl)trimethylammonium iodide
880-00-2

(4-carboxyphenyl)trimethylammonium iodide

Conditions
ConditionsYield
In methanol for 16h; Heating;35%
p-N,N-dimethylaminobenzoic acid
619-84-1

p-N,N-dimethylaminobenzoic acid

2-amino-5-methoxy-thiophenol
6274-29-9

2-amino-5-methoxy-thiophenol

4-(6-methoxybenzo[d]thiazol2-yl)-N,N-dimethylaniline
10205-71-7

4-(6-methoxybenzo[d]thiazol2-yl)-N,N-dimethylaniline

Conditions
ConditionsYield
In dimethyl sulfoxide at 170℃; for 0.5h;35%

619-84-1Relevant articles and documents

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin

supporting information, p. 6648 - 6653 (2021/09/08)

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Ou, Jinhua,Tan, Hong,He, Saiyu,Wang, Wei,Hu, Bonian,Yu, Gang,Liu, Kaijian

, p. 14974 - 14982 (2021/10/25)

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Triple-phase Boundary in Anion-Exchange Membrane Reactor Enables Selective Electrosynthesis of Aldehyde from Primary Alcohol

Atobe, Mahito,Fukazawa, Atsushi,Furutani, Yuka,Ido, Yuto,Sato, Yasushi,Shida, Naoki

, (2021/11/09)

Oxidation of primary alcohol to the corresponding aldehyde remains a significant challenge, even with the state-of-the-art chemistry. Here, a novel electrochemical system was developed for the exclusive production of aldehyde from primary alcohol using an anion-exchange membrane (AEM) reactor. Oxidation proceeded on a gold catalyst under basic conditions, which largely enhanced the reaction rate. Despite the basic nature around the reaction sites, the oxidation of primary alcohols exclusively yielded the corresponding aldehyde, which was attributed to the unique three-phase interfacial reaction sites in the AEM reactor. In addition to benzyl alcohol, the oxidation of allylic and aliphatic alcohols was also demonstrated. Comparison of constant potential electrolysis with the AEM reactor or a conventional batch-type cell revealed the crucial role of the triple-phase boundary for the selectivity of the oxidation of alcohol.

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