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N,N-Dimethylbenzamide
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Name

N,N-Dimethylbenzamide

 EINECS 210-279-2
CAS No. 611-74-5 Density 1.03 g/cm3
PSA 20.31000 LogP 1.38840
Solubility Soluble in water. Melting Point 41-45 °C
Formula C9H11NO Boiling Point 256.1 °C at 760 mmHg
Molecular Weight 149.192 Flash Point 111.9 °C
Transport Information N/A Appearance white to off-white crystals.
Safety 26-36-37/39 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 611-74-5 (N,N-Dimethylbenzamide) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Dimethylbenzamide;NSC 10996;

Article Data 274

N,N-Dimethylbenzamide Synthetic route

93-58-3

benzoic acid methyl ester

84738-97-6

methylchloroaluminum N,N-dimethylamide

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
In benzene for 12h; Heating;100%
15482-60-7

N,N-dimethylthiobenzamide

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With 6H(1+)*Mo9O40PV3(6-); oxygen In acetonitrile at 90℃; under 760.051 Torr; for 2h; Inert atmosphere; Glovebox;99%
With hydrogenchloride; N-nitrosopiperidine; potassium iodide In dichloromethane; water at 22℃; for 50h;94%
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.5h;94%
4375-83-1

tris(dimethylamino)borane

100-52-7

benzaldehyde

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h;99%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

65-85-0

benzoic acid

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(II) oxide In water at 80℃; for 20h; Catalytic behavior;99%
With tert.-butylhydroperoxide; copper(II) perchlorate hexahydrate at 100℃; for 15h;90%
With trichlorophosphate at 120℃; for 1h; Sealed tube;90%
74-94-2

dimethylamine borane

65-85-0

benzoic acid

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;99%
98-88-4

benzoyl chloride

A

2930-27-0

2,4,6-Triphenyl-thiopyrylium-chlorid

B

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With 2-Dimethylamino-2,4,6-triphenyl-2H-thiopyran In diethyl ether for 1h; Heating;A 98%
B 40%
87691-75-6

2-Dimethylamino-2,4,6-triphenyl-2H-thiopyran

A

2930-27-0

2,4,6-Triphenyl-thiopyrylium-chlorid

B

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With benzoyl chloride In diethyl ether for 1h; Heating;A 98%
B 40%
124-40-3

dimethyl amine

65-85-0

benzoic acid

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h;98%
With tetrabutylammomium bromide; iodine; potassium hydroxide In water at 20℃; for 2.5h; Irradiation;75%
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; triphenylphosphine In dichloromethane at 20℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;74%
Stage #1: dimethyl amine; benzoic acid at 60℃; Autoclave; Cooling with dry ice;
Stage #2: at 290℃; under 22502.3 Torr; for 0.0136111h; Microwave irradiation;
108-86-1

bromobenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With sodium methylate; nickel diacetate In 1,4-dioxane at 110℃;98%
Stage #1: N,N-dimethyl-formamide With 1,3,5-trichloro-2,4,6-triazine at 20℃; for 1h;
Stage #2: bromobenzene With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 6h;		81%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trichlorophosphate at 165℃; for 24h; Inert atmosphere;72%
591-50-4

iodobenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
With Pd nanoparticles supported on reduced graphene oxide nanosheets at 200℃; for 6h; Temperature; Concentration; Autoclave;98%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trichlorophosphate at 135℃; for 6h; Inert atmosphere;93%
Stage #1: N,N-dimethyl-formamide With tungsten(VI) chloride at 20℃; for 0.25h; Inert atmosphere;
Stage #2: iodobenzene With palladium dichloride at 140℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;		93%

N,N-Dimethylbenzamide Consensus Reports

Reported in EPA TSCA Inventory.

N,N-Dimethylbenzamide Specification

The N,N-Dimethylbenzamide, with the CAS registry number 611-74-5, is also known as Benzamide, N,N-dimethyl-. It belongs to the product categories of Amide; Amides; Carbonyl Compounds; Organic Building Blocks. Its EINECS registry number is 210-279-2. This chemical's molecular formula is C9H11NO and molecular weight is 149.19. What's more, its IUPAC name is the same with its product name.

Physical properties about N,N-Dimethylbenzamide are: (1)ACD/LogP: 0.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.43; (4)ACD/LogD (pH 7.4): 0.43; (5)ACD/BCF (pH 5.5): 1.26; (6)ACD/BCF (pH 7.4): 1.26; (7)ACD/KOC (pH 5.5): 41.07; (8)ACD/KOC (pH 7.4): 41.07;(9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 20.31 Å2; (13)Index of Refraction: 1.529; (14)Molar Refractivity: 44.63 cm3; (15)Molar Volume: 144.7 cm3; (16)Surface Tension: 37.4 dyne/cm; (17)Density: 1.03 g/cm3; (18)Flash Point: 111.9 °C; (19)Enthalpy of Vaporization: 49.36 kJ/mol; (20)Boiling Point: 256.1 °C at 760 mmHg; (21)Vapour Pressure: 0.0157 mmHg at 25 °C.

Preparation of N,N-Dimethylbenzamide: this chemical can be prepared by Benzoyl chloride with Dimethylamine. This reaction needs reagent Et3N and solvent diethyl ether. The yield is 90 %.

N,N-Dimethylbenzamide can be prepared by Benzoyl chloride with Dimethylamine.

Uses of N,N-Dimethylbenzamide: (1) it is used for deoxidizing reaction of secondary alcohol; (2) it is used to produce other chemicals. For example, it can produce Benzyl-dimethyl-amine. The reaction occurs with reagents HSiEt3, Et2NH and solvent toluene at temperature of 100 °C. The yield is 99.5 %.

N,N-Dimethylbenzamide can produce Benzyl-dimethyl-amine.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. If swallowed, it's harmful to health. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N(C)C)c1ccccc1
(2) InChI: InChI=1S/C9H11NO/c1-10(2)9(11)8-6-4-3-5-7-8/h3-7H,1-2H3
(3) InChIKey: IMNDHOCGZLYMRO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 960mg/kg (960mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 20, 1971.
 

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