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96-31-1

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96-31-1 Usage

Description

1, 3-Dimethylurea is a urea derivative and used as an intermediate in organic synthesis. It is a colorless crystalline powder with little toxicity. It is also used for synthesis of caffeine, pharmachemicals, textile aids, herbicides and other. In the textile processing industry 1,3-dimethylurea is used as intermediate for the production of formaldehyde-free easy-care finishing agents for textiles. In the Swiss Product Register there are 38 products containing 1,3-dimethylurea, among them 17 products intended for consumer use. Product types are e.g. paints and cleaning agents. The content of 1,3-dimethylurea in consumer products is up to 10 % (Swiss Product Register, 2003). Use in cosmetics has been proposed, but there is no information available as to its actual use in such applications.

Chemical Properties

white crystals

Uses

N,N′-Dimethylurea can be used:As a starting material to synthesize N,N′-dimethyl-6-amino uracil. In combination with β-cyclodextrin derivatives, to form low melting mixtures (LMMs), which can be used as solvents for hydroformylation and Tsuji-Trost reactions.To synthesize N,N′-disubstituted-4-aryl-3,4-dihydropyrimidinones via Biginelli condensation under solvent-free conditions.

Definition

ChEBI: A member of the class of ureas that is urea substituted by methyl groups at positions 1 and 3.

Air & Water Reactions

Water soluble.

Reactivity Profile

1,3-Dimethylurea is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 1,3-Dimethylurea emits toxic fumes.

Fire Hazard

Flash point data for 1,3-Dimethylurea are not available; 1,3-Dimethylurea is probably combustible.

Safety Profile

Moderately toxic by intraperitoneal route. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx

Purification Methods

Crystallise the urea from acetone/diethyl ether by cooling in an ice bath. Also crystallise it from EtOH and dry it at 50o/5mm for 24hours [Bloemendahl & Somsen J Am Chem Soc 107 3426 1985]. [Beilstein 4 IV 207.]

Check Digit Verification of cas no

The CAS Registry Mumber 96-31-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 96-31:
(4*9)+(3*6)+(2*3)+(1*1)=61
61 % 10 = 1
So 96-31-1 is a valid CAS Registry Number.
InChI:InChI=1/C3H8N2O/c1-4-3(6)5-2/h1-2H3,(H2,4,5,6)

96-31-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D0289)  1,3-Dimethylurea  >98.0%(GC)

  • 96-31-1

  • 25g

  • 115.00CNY

  • Detail
  • TCI America

  • (D0289)  1,3-Dimethylurea  >98.0%(GC)

  • 96-31-1

  • 500g

  • 290.00CNY

  • Detail
  • Alfa Aesar

  • (B21329)  N,N'-Dimethylurea, 98%   

  • 96-31-1

  • 250g

  • 226.0CNY

  • Detail
  • Alfa Aesar

  • (B21329)  N,N'-Dimethylurea, 98%   

  • 96-31-1

  • 500g

  • 371.0CNY

  • Detail
  • Alfa Aesar

  • (B21329)  N,N'-Dimethylurea, 98%   

  • 96-31-1

  • 1000g

  • 611.0CNY

  • Detail
  • Sigma-Aldrich

  • (36574)  N,N′-Dimethylurea  PESTANAL®, analytical standard

  • 96-31-1

  • 36574-250MG

  • 360.36CNY

  • Detail
  • Aldrich

  • (40410)  N,N′-Dimethylurea  (sym.), ≥95.0% (HPLC), technical

  • 96-31-1

  • 40410-50G

  • 389.61CNY

  • Detail
  • Aldrich

  • (40410)  N,N′-Dimethylurea  (sym.), ≥95.0% (HPLC), technical

  • 96-31-1

  • 40410-1KG

  • 639.99CNY

  • Detail

96-31-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N'-dimethylurea

1.2 Other means of identification

Product number -
Other names Urea,N,N'-dimethyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Agricultural chemicals (non-pesticidal)
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:96-31-1 SDS

96-31-1Synthetic route

S,S-dimethyl dithiocarbonate
868-84-8

S,S-dimethyl dithiocarbonate

methylamine
74-89-5

methylamine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
In water at 60℃; for 2h;97%
1,3-Dimethyl-5-(1-phenyl-ethyl)-[1,3,5]triazinan-2-one
130749-94-9

1,3-Dimethyl-5-(1-phenyl-ethyl)-[1,3,5]triazinan-2-one

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

Conditions
ConditionsYield
With ammonium chloride at 70℃; for 3h; other hexahydro-2-oxo-1,3,5-triazines;A n/a
B 90%
sodium methylate
124-41-4

sodium methylate

1,3-Dimethyl-1-(1H-pyrazole-4-carbonyl)-urea
80981-25-5

1,3-Dimethyl-1-(1H-pyrazole-4-carbonyl)-urea

A

methyl pyrazole-4-carboxylate
51105-90-9

methyl pyrazole-4-carboxylate

B

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
In methanol for 2h; Heating;A 79%
B 83%
1,3-Dimethyl-1-(1H-pyrazole-4-carbonyl)-urea
80981-25-5

1,3-Dimethyl-1-(1H-pyrazole-4-carbonyl)-urea

A

methyl pyrazole-4-carboxylate
51105-90-9

methyl pyrazole-4-carboxylate

B

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Heating;A 79%
B 83%
ethyl 3-phenylglycidate
121-39-1

ethyl 3-phenylglycidate

N,N-dimethylthiourea
534-13-4

N,N-dimethylthiourea

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

(Z)-N-methyl-N-(methylcarbamoyl)-3-phenylacrylamide

(Z)-N-methyl-N-(methylcarbamoyl)-3-phenylacrylamide

C

(E)-N-methyl-N-(methylcarbamoyl)-3-phenylacrylamide

(E)-N-methyl-N-(methylcarbamoyl)-3-phenylacrylamide

Conditions
ConditionsYield
With ytterbium(III) triflate In 1,4-dioxane at 90℃; for 8h; Schlenk technique; Inert atmosphere; Sealed tube;A n/a
B 8%
C 80%
1,3-dimethyl-4-thiouracil
49785-67-3

1,3-dimethyl-4-thiouracil

6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

1,3-dimethyl-7-mercaptopyrido<2,3-d>pyrimidine-2,4-(1H,3H)-dione
74115-57-4

1,3-dimethyl-7-mercaptopyrido<2,3-d>pyrimidine-2,4-(1H,3H)-dione

Conditions
ConditionsYield
With sodium ethanolate In ethanolA n/a
B 78%
L-cysteine ethyl ester hydrochloride
868-59-7

L-cysteine ethyl ester hydrochloride

1-(tert-butylimino-methyl)-1,3-dimethylurea hydrochloride

1-(tert-butylimino-methyl)-1,3-dimethylurea hydrochloride

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

ethyl (R)-4,5-dihydrothiazole-4-carboxylate
206876-90-6

ethyl (R)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane Heating;A n/a
B 78%
N,N-dimethylthiourea
534-13-4

N,N-dimethylthiourea

benzil
134-81-6

benzil

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

1,3,4,6-Tetramethyl-3a,6a-diphenyl-5-thioxo-hexahydro-imidazo[4,5-d]imidazol-2-one
137514-25-1

1,3,4,6-Tetramethyl-3a,6a-diphenyl-5-thioxo-hexahydro-imidazo[4,5-d]imidazol-2-one

C

1,3-dimethyl-4,5-diphenyl-5-imidazoline-2-thioneN,N-dimethyl-4-oxo-4H-chromene-2-carboxamide
16459-85-1

1,3-dimethyl-4,5-diphenyl-5-imidazoline-2-thioneN,N-dimethyl-4-oxo-4H-chromene-2-carboxamide

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 4h; Mechanism; Heating; other substrates;A n/a
B n/a
C 71%
With hydrogenchloride In ethanol for 4h; Heating;A n/a
B n/a
C 71%
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
4869-46-9

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

1-phenylbutan-1,3-dione
93-91-4

1-phenylbutan-1,3-dione

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

3-benzoyl-4-hydroxy-N-methylbenzamide

3-benzoyl-4-hydroxy-N-methylbenzamide

Conditions
ConditionsYield
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃;A 6%
B 70%
6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

5-(1,3-Dimethyl-2,4-dioxopyrimidil)methyl ketone
36980-95-7

5-(1,3-Dimethyl-2,4-dioxopyrimidil)methyl ketone

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

6-Acetyl-1,3-dimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione
74115-56-3

6-Acetyl-1,3-dimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 9h; Heating;A n/a
B 65%
6-amino-1,3-diethyluracil
41740-15-2

6-amino-1,3-diethyluracil

1,3-dimethyl-5-cyanouracil
36980-91-3

1,3-dimethyl-5-cyanouracil

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

1,3-Diethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile
74115-53-0

1,3-Diethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 1h; Heating;A n/a
B 65%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

methylamine
74-89-5

methylamine

A

2,5-dioxopyrrolidin-1-yl methylcarbamate
18342-66-0

2,5-dioxopyrrolidin-1-yl methylcarbamate

B

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
In acetonitrile Ambient temperature;A 63.1%
B n/a
6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

1,3-dimethyl-5-cyanouracil
36980-91-3

1,3-dimethyl-5-cyanouracil

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

6-cyano-1,3-dimethylpyrido<2,3-d>pyrimidine-2,4,7-(1H,3H,8H)-trione
74115-52-9

6-cyano-1,3-dimethylpyrido<2,3-d>pyrimidine-2,4,7-(1H,3H,8H)-trione

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 4h; Heating;A n/a
B 63%
6-amino-1,3-dipropyluracil
41862-14-0

6-amino-1,3-dipropyluracil

1,3-dimethyl-5-cyanouracil
36980-91-3

1,3-dimethyl-5-cyanouracil

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

2,4,7-Trioxo-1,3-dipropyl-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile
74115-54-1

2,4,7-Trioxo-1,3-dipropyl-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 2h; Heating;A n/a
B 63%
N1,N3-dimethyl-N1-nitrosothiourea
79645-01-5

N1,N3-dimethyl-N1-nitrosothiourea

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether for 0.5h;62%
With hydrogenchloride; water 1) ether, 2) ether; Yield given. Multistep reaction;
sodium ethanolate
141-52-6

sodium ethanolate

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
4869-46-9

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

acetylacetone
123-54-6

acetylacetone

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

ethyl 3-acetyl-4-hydroxybenzoate
57009-53-7

ethyl 3-acetyl-4-hydroxybenzoate

Conditions
ConditionsYield
In ethanol for 2h; Mechanism; Heating; other 1,3-ambident nucleophiles. Object of study: a novel ring transformation;A n/a
B 55%
In ethanol for 2h; Heating;A n/a
B 55%
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
4869-46-9

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

acetylacetone
123-54-6

acetylacetone

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

ethyl 3-acetyl-4-hydroxybenzoate
57009-53-7

ethyl 3-acetyl-4-hydroxybenzoate

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 2h; Heating; Yield given;A n/a
B 55%
With sodium ethanolate In ethanol for 2h; Heating; Yield given;
6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

1,3-dimethyl-5-nitrouracil
41613-26-7

1,3-dimethyl-5-nitrouracil

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

6-nitropyridopyrimidine
74115-55-2

6-nitropyridopyrimidine

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 3h; Heating;A n/a
B 50%
methylamine
74-89-5

methylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 50%
methanol
67-56-1

methanol

3,4-dihydro-3,5,6-trimethyl-2,4-dioxo-2H-1,3,5-oxadiazinium hexachloroantimonate

3,4-dihydro-3,5,6-trimethyl-2,4-dioxo-2H-1,3,5-oxadiazinium hexachloroantimonate

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

1,1-dimethoxyethylium hexachloroantimonate

1,1-dimethoxyethylium hexachloroantimonate

Conditions
ConditionsYield
In dichloromethane at 23℃; for 2h;A n/a
B 48%
1,8-bis(1,3-dimethyluracil-6-yl)-cyclam
1215225-05-0

1,8-bis(1,3-dimethyluracil-6-yl)-cyclam

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

11-(1,3-dimethyluracil-6-yl)-1,4,8,11-tetraaza-17-oxo-tricyclo[6.6.3.0(4,15)]heptadecanium perchlorate

11-(1,3-dimethyluracil-6-yl)-1,4,8,11-tetraaza-17-oxo-tricyclo[6.6.3.0(4,15)]heptadecanium perchlorate

Conditions
ConditionsYield
With zinc(II) perchlorate In dimethyl sulfoxide at 120℃; for 1h;A n/a
B 44.2%
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
4869-46-9

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

acetylacetone
123-54-6

acetylacetone

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

3-acetyl-4-hydroxy-N-methylbenzamide

3-acetyl-4-hydroxy-N-methylbenzamide

C

1-(3-acetyl-4-hydroxybenzoyl)-1,3-dimethylurea

1-(3-acetyl-4-hydroxybenzoyl)-1,3-dimethylurea

D

6-acetyl-7-hydroxy-1,3-dimethylquinazoline-2,4(1H,3H)-dione

6-acetyl-7-hydroxy-1,3-dimethylquinazoline-2,4(1H,3H)-dione

Conditions
ConditionsYield
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃;A 4%
B 15%
C 36%
D 14%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
4869-46-9

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

3-(Ethoxycarbonyl)-4-hydroxy-N-methylbenzamide
74442-97-0

3-(Ethoxycarbonyl)-4-hydroxy-N-methylbenzamide

C

6-ethoxycarbonyl-7-hydroxy-1,3-dimethylquinazoline-2,4(1H,3H)-dione

6-ethoxycarbonyl-7-hydroxy-1,3-dimethylquinazoline-2,4(1H,3H)-dione

Conditions
ConditionsYield
With potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃;A 9%
B 20%
C 34%
1,3-dimethyluracil
874-14-6

1,3-dimethyluracil

6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

A

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

B

1,3-dimethylpyrido<2,3-d>pyrimidine-2,4,7(1H,3H,8H)-trione
57821-20-2

1,3-dimethylpyrido<2,3-d>pyrimidine-2,4,7(1H,3H,8H)-trione

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 95h; Heating;A n/a
B 33%
nitromethane
75-52-5

nitromethane

carbon monoxide
201230-82-2

carbon monoxide

methylamine
74-89-5

methylamine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
With iron(III) chloride In methanol; N,N-dimethyl-formamide at 75℃; under 4137.29 Torr; for 6h; Catalytic behavior; Autoclave;32%
Stage #1: nitromethane; methylamine In methanol; N,N-dimethyl-formamide for 0.166667h;
Stage #2: carbon monoxide With iron(III) chloride In methanol; N,N-dimethyl-formamide at 90℃; under 3040.2 Torr; for 5h; Autoclave;
28%
1,3-bis(hydroxymethyl)urea
140-95-4

1,3-bis(hydroxymethyl)urea

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc
N,N'-bis(methoxymethyl)urea
141-07-1

N,N'-bis(methoxymethyl)urea

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
With nickel at 100℃; under 51485.6 - 102971 Torr; Hydrogenation;
methylammonium N-methylcarbamate
65398-48-3

methylammonium N-methylcarbamate

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
at 170℃;
methyl isocyanate
624-83-9

methyl isocyanate

methylamine
74-89-5

methylamine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

methyl isocyanate
624-83-9

methyl isocyanate

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
With water
With water at 100℃;
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

3a,8a-dihydroxy-1,3-dimethyl-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione
22431-02-3

3a,8a-dihydroxy-1,3-dimethyl-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione

Conditions
ConditionsYield
at 20℃; for 2h;100%
In water at 50 - 60℃;82%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

N-chloro-N,N'-dimethylurea
24776-91-8

N-chloro-N,N'-dimethylurea

Conditions
ConditionsYield
With sodium hypochlorite In water Product distribution / selectivity;100%
With water; sodium chloride at 20℃; for 0.5h; Reagent/catalyst; pH-value; Concentration; Electrolysis;89%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Glyoxilic acid
298-12-4

Glyoxilic acid

5-hydroxy-1,3-dimethylimidazolidine-2,4-dione
64732-10-1

5-hydroxy-1,3-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
In ethyl acetate Solvent;100%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

N,N'-dimethyl-N,N'-dinitrourea
25466-50-6

N,N'-dimethyl-N,N'-dinitrourea

Conditions
ConditionsYield
With dinitrogen pentoxide In carbon dioxide at 0 - 5℃; under 45004.5 - 60006 Torr; for 0.5h; Time; liquid CO2;99%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

N-methylsulfamic acid
4112-03-2

N-methylsulfamic acid

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide In 1,2-dichloro-ethane Product distribution; 1.) r.t., 15 min; 2.) 70-80 deg C; effect of oleum concentration in different solvents, influence of the temperature of dissolution of sulfuric acid, influence of reaction temperature on the yield;98%
With sulfuric acid; sulfur trioxide In 1,2-dichloro-ethane 1.) 15 min, r.t.; 2.) 70-80 deg C, 6-8 h;98%
With sulfuric acid; sulfur trioxide
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Diphenylamino-phosphordichlorid
4614-90-8

Diphenylamino-phosphordichlorid

1,3-dimethyl-2-diphenylamino-1,3-diaza-2λ3-phosphetidin-4-on
126695-44-1

1,3-dimethyl-2-diphenylamino-1,3-diaza-2λ3-phosphetidin-4-on

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 12h; Ambient temperature;98%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

1,3 dimethyl 1 nitrosourea
13256-32-1

1,3 dimethyl 1 nitrosourea

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 0℃; for 1h;98%
With sulfuric acid; sodium nitrite In water cooling;58%
With cis-nitrous acid In 1,4-dioxane; water Rate constant; variation of H2O/dioxane ratio, addition of acids or salts;
formaldehyd
50-00-0

formaldehyd

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

1,3-Dimethyl-5-(1-phenyl-ethyl)-[1,3,5]triazinan-2-one
130749-94-9

1,3-Dimethyl-5-(1-phenyl-ethyl)-[1,3,5]triazinan-2-one

Conditions
ConditionsYield
In water at 70 - 110℃;98%
2-chloropyridine
109-09-1

2-chloropyridine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

N,N'-dimethyl-N-(pyridin-2-yl)urea

N,N'-dimethyl-N-(pyridin-2-yl)urea

Conditions
ConditionsYield
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; palladium diacetate In 1,4-dioxane at 100℃; for 2h;98%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

methyl trans-5-[(tert-butylamino)carbonyl]-1,3-dimethyl-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate

methyl trans-5-[(tert-butylamino)carbonyl]-1,3-dimethyl-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate

Conditions
ConditionsYield
With D-glucose In water at -5 - 20℃;98%
triphenylboroxine
3262-89-3

triphenylboroxine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Bis-(dimethylamino)-phenylboran
1201-45-2

Bis-(dimethylamino)-phenylboran

O(μ-C6H5BNCH3)2CO
81233-30-9

O(μ-C6H5BNCH3)2CO

Conditions
ConditionsYield
In toluene byproducts: (CH3)2NH; under inert atm., mixt. of (C6H5BO)3 and ((CH3)2N)2BC6H5 heated for 90 min to 125°C, cooled to room temp., addn. of toluene and (NHCH3)2CO, stirred mixt. heated to reflux for 4 days; evapn., distd. under vac., sublimation, slowly crystn. on standing; elem. anal.;98%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

benzoic acid
65-85-0

benzoic acid

N-methylbenzamide
88070-48-8

N-methylbenzamide

Conditions
ConditionsYield
With zirconyl chloride octahydrate for 0.05h; Irradiation;98%
With 1H-imidazole In octane at 130℃; for 24h;
vinyl acetate
108-05-4

vinyl acetate

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

isopropyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction;98%
N-methylene-tert-butylamine
13987-61-6

N-methylene-tert-butylamine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

5-tert-Butyl-1,3-dimethyl-[1,3,5]triazinan-2-one
65282-91-9

5-tert-Butyl-1,3-dimethyl-[1,3,5]triazinan-2-one

Conditions
ConditionsYield
for 4h; Heating;97%
chloral hydrate
302-17-0

chloral hydrate

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

1-methyl-1-(1-hydroxy-2,2,2-trichloroethyl)-3-methyl urea

1-methyl-1-(1-hydroxy-2,2,2-trichloroethyl)-3-methyl urea

Conditions
ConditionsYield
With 3 A molecular sieve In 1,4-dioxane at 70℃; for 168h; Substitution;97%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

phosphorochloridous acid bis-(2,4-di-tert-butyl-phenyl) ester; compound with hexane

phosphorochloridous acid bis-(2,4-di-tert-butyl-phenyl) ester; compound with hexane

P(OC6H3Bu(t)2-2,4)2N(Me)CON(Me)H

P(OC6H3Bu(t)2-2,4)2N(Me)CON(Me)H

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 4h;97%
(pentacarbonyl)(phenylethynyl)(ethoxy)carbene chromium(0)

(pentacarbonyl)(phenylethynyl)(ethoxy)carbene chromium(0)

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

[Cr(CO)5(C4HN2O(C6H5)(CH3)2)]
206069-47-8

[Cr(CO)5(C4HN2O(C6H5)(CH3)2)]

Conditions
ConditionsYield
In tetrahydrofuran heating of (CO)5Cr(C(CCPh)OCH2CH3) and HNMeCONHMe (2 equiv.) at 60°C in THF with stirring (Organometallics 17 (1998) 2135); cooling to room temp.; evapn. of solvent in vac., flash chromy.;97%
In tetrahydrofuran Ar-atmosphere; room temp. (48 h);70%
vinyl acetate
108-05-4

vinyl acetate

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

isobutyl acetoacetate
7779-75-1

isobutyl acetoacetate

isobutyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

isobutyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction;97%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

1,3,6-trimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
67092-74-4

1,3,6-trimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In neat (no solvent) at 80℃; for 0.025h; Catalytic behavior; Reagent/catalyst; Solvent; Microwave irradiation;96%
With chloro-trimethyl-silane In N,N-dimethyl-formamide79%
With hafnium tetrakis(trifluoromethanesulfonate) In neat (no solvent) at 80℃; Biginelli Pyrimidone Synthesis;68%
Dowex-50W at 130℃; Biginelli condensation;59%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

3-nitrophthalic acid
603-11-2

3-nitrophthalic acid

Ethyl S-(acetylamino)-1,2,3,4-tetrahydro-2-methyl-7-nitro-8-isoquinolinepropanoate

Ethyl S-(acetylamino)-1,2,3,4-tetrahydro-2-methyl-7-nitro-8-isoquinolinepropanoate

Conditions
ConditionsYield
In ethanol96%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

acetic anhydride
108-24-7

acetic anhydride

cyanoacetic acid
372-09-8

cyanoacetic acid

6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

Conditions
ConditionsYield
at 60℃; for 3h;96%
5-methoxyisatine
39755-95-8

5-methoxyisatine

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

2-(4-hydroxy-1,3-dimethyl-2,5-dioxoimidazolidin-4-yl)-4-methoxybenzenaminium 4-methylbenzenesulfonate

2-(4-hydroxy-1,3-dimethyl-2,5-dioxoimidazolidin-4-yl)-4-methoxybenzenaminium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In acetonitrile at 80℃; for 3h;96%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

2,2-diphenylacetic acid
117-34-0

2,2-diphenylacetic acid

N-methyldiphenylacetamide
954-21-2

N-methyldiphenylacetamide

Conditions
ConditionsYield
With magnesium(II) nitrate hexahydrate In octane at 130℃; for 24h; Reagent/catalyst;96%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

sodium p-toluenesulfonamide
18522-92-4

sodium p-toluenesulfonamide

A

N-Methyl-N'-toluene-p-sulfonylurea
13909-69-8

N-Methyl-N'-toluene-p-sulfonylurea

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
at 160℃; for 3h; Product distribution; Rate constant; Equilibrium constant; Other temperature, other time, other ratio of reactants, activation energy, ΔH, ΔS;;A 95.5%
B n/a
at 160℃; for 3h;A 95.5%
B n/a
formaldehyd
50-00-0

formaldehyd

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

5-((1R,2R)-2-Hydroxy-cyclohexyl)-1,3-dimethyl-[1,3,5]triazinan-2-one
130750-04-8

5-((1R,2R)-2-Hydroxy-cyclohexyl)-1,3-dimethyl-[1,3,5]triazinan-2-one

Conditions
ConditionsYield
In water at 70 - 110℃;95%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

3-trifluoromethylnitrobenzene
98-46-4

3-trifluoromethylnitrobenzene

N-methyl-4-nitro-2-trifluoromethylaniline
54672-10-5

N-methyl-4-nitro-2-trifluoromethylaniline

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide95%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

2,4-dichloro-5-(chlorosulfonyl)benzoic acid
3740-18-9

2,4-dichloro-5-(chlorosulfonyl)benzoic acid

2,4-dichloro-5-chlorosulfonylbenzoic acid N-methylamide
89894-62-2

2,4-dichloro-5-chlorosulfonylbenzoic acid N-methylamide

Conditions
ConditionsYield
at 90℃;95%
4-Methoxyphenylacetic acid
104-01-8

4-Methoxyphenylacetic acid

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

2-(4-methoxyphenyl)-N-methylacetamide
59907-36-7

2-(4-methoxyphenyl)-N-methylacetamide

Conditions
ConditionsYield
With 1H-imidazole In octane at 130℃; for 24h; Reagent/catalyst;95%
4-chlorophenylacetic Acid
1878-66-6

4-chlorophenylacetic Acid

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

2-(4-chlorophenyl)-N-methylacetamide
60336-41-6

2-(4-chlorophenyl)-N-methylacetamide

Conditions
ConditionsYield
With magnesium(II) nitrate hexahydrate In octane at 130℃; for 24h; Reagent/catalyst;95%

96-31-1Relevant articles and documents

Preparation and reaction of uracil substituted cyclen and cyclam: formation of tricyclic guanidinium and dihydroimidazolium salts

Watanabe, Soichiro,Komori, Ayako,Saito, Masayuki,Uchida, Akira

, p. 1196 - 1201 (2010)

Di-uracil substituted cyclen derivatives were prepared by the reaction of cyclen with 6-chloro-1-methyluracil or 6-chloro-1,3-dimethyluracil. The reaction of cyclam with 6-chloro-1,3-dimethyluracil gave a similar di-uracil substituted cyclam. The 1,7-di-uracil substituted cyclen was converted to the tricyclic guanidinium salt and acylurea upon heating in DMSO in the presence of weak acid. The 1,8-di-uracil substituted cyclam gave a tricyclic dihydroimidazolium salt under the same conditions. These reactions can be explained by an intramolecular uracil ring-breaking reaction mechanism.

On the Reaction of Acylium Salts with Isocyanates

Hamed, A.,Ismail, A.,Hitzler, M. G.,Jochims, J. C.

, p. 385 - 390 (1995)

Alkyl isocyanates (3) react with acylium salts (2) in a 2:1 ratio to furnish 3,4-dihydro-2,4-dioxo-2H-1,3,5-oxadiazinium salts 4.These cyclic N-acyliminium salts are decomposed with catalytic amounts of water to give either oxadiazinium salts 5 or pyrimidinium salts 7.With aqueous base compounds 4 are transformed into acylureas 6.Hetero substituted open chain N-acyliminium slats (8a, 11c, 12c, 13f, 15g, 16a) are produced from 4 by treatment with heteronucleophiles such as methanol, p-anisidine, p-cresol, thiophenol, 1,3-dimethylurea, or benzohydrazide, respectively.Excess of nucleophile furnishes further degradation products of 4, e.g. oxonium salts (9a) and iminium salts (14f).

Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation

Wu, Fan,Alom, Nur-E,Ariyarathna, Jeewani P.,Na?, Johannes,Li, Wei

supporting information, p. 11676 - 11680 (2019/07/31)

A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.

Synthesis and architecture of polystyrene-supported Schiff base-palladium complex: Catalytic features and functions in diaryl urea preparation in conjunction with Suzuki-Miyaura cross-coupling reaction by reductive carbonylation

Basu, Priyanka,Riyajuddin, Sk,Dey, Tusar Kanto,Ghosh, Aniruddha,Ghosh, Kaushik,Islam, Sk Manirul

, p. 37 - 50 (2018/10/02)

This work represents an efficient and unique phosphine-free approach for the polystyrene embedded Schiff-base palladium catalyzed diaryl urea synthesis and Suzuki-Miyaura cross-coupling reaction by reductive carbonylation process. The careful instrumental investigations with FE-SEM, TEM, EDAX, TGA, UV–Vis, FTIR, AAS, and elemental analysis precisely characterized the developed heterogeneous catalyst. Reaction parameters, like catalytic natures, starting materials, reaction environment, and solvent were examined sequentially. The present work has been adequately addressed to account for the generation and characterization of a new polymer bound Pd-catalyst and using it in the synthesis of diaryl ureas and diaryl ketones, with no substantial decay of catalytic activity.

METHOD FOR ALKYLATING AN AMINO COMPOUND

-

Page/Page column 14; 15, (2018/06/12)

The invention relates to a method for alkylating an amino compound, characterized in that at least one triazine derivative of general formula (I) or at least one urea or urea derivative of the general formula (II), (II), wherein ? R4 and R5 mean independently from each other Q1 or a moiety of the formula R6-N-R7 or R8-N-R9 bound with its central nitrogen atom to the triazine ring of the structure of formula (I), whereat - Q1 means a linear or branched C1-C30-alkyl or a cyclic substituent in form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkylsubstituted C5-C20-aryl or an amide of a cyclic unsaturated carboxylic acid, whereat the C1-C30-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted nitrogen atoms and/or by one or multiple groups of the type –C(O)O-,-OC(O)-,-C(O)- and/or –OC(O)O-, ? R1, R2, R3, R6, R7, R8 and R9 mean independently from each other H, linear or branched C1-C20-alkyl, C5-C20-cyclo alkyl, C5-C20-aryl, C1-C20-alkylsubstituted C5-C20-aryl, which in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms and/or substituted nitrogen atoms and/or by one or multiple groups of the type –C(O)O-, - OC(O)-, -C(O)- and/or –OC(O) O- and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups, and ? X means O or S, is reacted with at least one alcohol of the general formula (III) R10-OH wherein R10 means a linear or branched C1-C20-alkyl, C5-C20-cycloalkyl, or C1-C20- alkylsubstituted C5-C20-aryl, which can be in each case interrupted by one or multiple oxygen atoms, sulphur atoms, substituted nitrogen atoms and/or by one or multiple groups of the type –C(O)O-, -OC(O)-, -C(O)- and/or –OC(O)O- and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups, wherein the reaction is carried out in the presence of at least one Ruthenate of the general formula (IV) Mn(RuO4) and/or at least one Perruthenate of the general formula (V) M(RuO4)n wherein the cation M is selected from a group comprising an alkali, earth alkali or substituted or non-substituted ammonium cation.

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