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598-55-0

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598-55-0 Usage

Chemical Properties

WHITE ADHERING CRYSTALS

Uses

Methyl carbamate was used in the synthesis of protected aminocyclopropanes.

Preparation

Methyl carbamate was synthesized by the following preparation. MDI (5.00 g,0.020mol) and 100 ml of dried acetone were weighed into a Ng-filled three-neck flask.Methanol (5 g, an excess amount) is added dropwise to the stirred MDI solution in the flask,and then the solution was heated to 56 C. After 24 hrs, the reaction mixture was cooled down to room temperature and evaporated to give a crude solid at about 100% yield. The following recrystallization procedure gave 3.1 g of a white solid (0.012 mol,60% yield). The disappearance of FT-IR stretching band of the isocyanate group (-N=C=O, 2280 cm') confirmed that the reaction was complete.

Definition

ChEBI: Methyl carbamate is a carbamate ester resulting from the formal condensation of the carboxy group of carbamic acid with methanol.

General Description

White crystals.

Air & Water Reactions

Water soluble.

Reactivity Profile

Methyl carbamate is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Fire Hazard

Flash point data for Methyl carbamate are not available; however, Methyl carbamate is probably combustible.

Safety Profile

Poison by ingestion and intraperitoneal routes. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

Purification Methods

Crystallise the carbamate from *benzene or distil it. [Beilstein 3 H 21.]

Check Digit Verification of cas no

The CAS Registry Mumber 598-55-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 8 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 598-55:
(5*5)+(4*9)+(3*8)+(2*5)+(1*5)=100
100 % 10 = 0
So 598-55-0 is a valid CAS Registry Number.
InChI:InChI=1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)

598-55-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A16523)  Methyl carbamate, 99%   

  • 598-55-0

  • 50g

  • 227.0CNY

  • Detail
  • Alfa Aesar

  • (A16523)  Methyl carbamate, 99%   

  • 598-55-0

  • 100g

  • 254.0CNY

  • Detail
  • Alfa Aesar

  • (A16523)  Methyl carbamate, 99%   

  • 598-55-0

  • 500g

  • 644.0CNY

  • Detail
  • Aldrich

  • (246352)  Methylcarbamate  98%

  • 598-55-0

  • 246352-100G

  • 279.63CNY

  • Detail
  • Aldrich

  • (246352)  Methylcarbamate  98%

  • 598-55-0

  • 246352-500G

  • 721.89CNY

  • Detail
  • Vetec

  • (V900708)  Methylcarbamate  Vetec reagent grade, 98%

  • 598-55-0

  • V900708-100G

  • 115.83CNY

  • Detail
  • Vetec

  • (V900708)  Methylcarbamate  Vetec reagent grade, 98%

  • 598-55-0

  • V900708-500G

  • 356.85CNY

  • Detail

598-55-0SDS

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 methyl carbamate

1.2 Other means of identification

Product number -
Other names Urethylane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals,Intermediates,Paint additives and coating additives not described by other categories
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:598-55-0 SDS

598-55-0Synthetic route

methanol
67-56-1

methanol

urea
57-13-6

urea

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With alumina supported titanium dioxide-bismuth oxide metal oxide catalyst at 120℃; for 8h; Sealed tube;99.41%
Stage #1: methanol; urea at 30℃; for 20h; Autoclave;
Stage #2: With carbon dioxide; 6O4P(3-)*5Ni(2+)*5Ca(2+)*2F(1-) at 160℃; under 4500.45 Torr; for 6h; Temperature; Concentration;
98.9%
With silica supported titanium dioxide at 160℃; under 17251.7 Torr; for 8h; Temperature; Pressure; Inert atmosphere;98%
urea
57-13-6

urea

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With Na-ZnO-ZrO2 / γ-Al2O3 at 180℃; for 6h; Temperature; Reagent/catalyst; Autoclave;98.8%
C9H10N2O6S
80284-00-0

C9H10N2O6S

A

methyl carbamate
598-55-0

methyl carbamate

B

ammonium salt of N-nitro-p-toluenesulfamide

ammonium salt of N-nitro-p-toluenesulfamide

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.0833333h;A 78%
B 92%
methanol
67-56-1

methanol

1,2-bis(1-isocyanato-1-methylethyl)diazene
70678-13-6

1,2-bis(1-isocyanato-1-methylethyl)diazene

A

5,5-dimethyl-Δ1-1,2,4-triazolin-3-one
112700-85-3

5,5-dimethyl-Δ1-1,2,4-triazolin-3-one

B

methyl carbamate
598-55-0

methyl carbamate

C

2-methoxy-2-methoxycarbonylaminopropane

2-methoxy-2-methoxycarbonylaminopropane

D

[1-(1-Methoxycarbonylamino-1-methyl-ethylazo)-1-methyl-ethyl]-carbamic acid methyl ester

[1-(1-Methoxycarbonylamino-1-methyl-ethylazo)-1-methyl-ethyl]-carbamic acid methyl ester

Conditions
ConditionsYield
for 2h; Product distribution; Mechanism; Heating; other alcohols; var. reaction time; var. temperatures;A 90%
B n/a
C n/a
D n/a
for 2h; Heating; Yield given. Yields of byproduct given;
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

A

ethyleneimine
151-56-4

ethyleneimine

B

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With ammonia In ethanol at 18 - 25℃; for 24h;A n/a
B 90%
methanol
67-56-1

methanol

urea
57-13-6

urea

A

methyl carbamate
598-55-0

methyl carbamate

B

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
at 179.84℃; for 10h;A 84.8%
B 6.5%
With zinc/aluminum mixed oxide at 179.84℃; for 10h; Reagent/catalyst; Autoclave;A 55.1%
B 36.5%
calcined La(NO3)3x6H2O at 170℃; under 14821 Torr; for 4h; Product distribution / selectivity; Autoclave; Inert atmosphere;A 41.2%
B 53.4%
With Zn/Ca-catalyst at 179.84℃; for 10h;A 50.5%
B 41.2%
With Ga2O3/CeO2-Al2O3 at 110℃; for 5h;
methanol
67-56-1

methanol

potassium cyanate
590-28-3

potassium cyanate

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With para-dodecylbenzenesulfonic acid In neat (no solvent) at 60℃; for 0.5h; Green chemistry;80%
With DBSA at 60℃; for 1h;
methyl chloroformate
79-22-1

methyl chloroformate

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane; ethyl acetate78%
With ammonia; benzene
With potassium hydrogencarbonate In water
methanol
67-56-1

methanol

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine
2911-21-9

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine

A

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

B

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With triethylamine for 24h; Heating;A 70%
B 15%
3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene
4651-91-6

3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene

methyl chloroformate
79-22-1

methyl chloroformate

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With sodium hydrogencarbonate In butanone66%
methanol
67-56-1

methanol

urea
57-13-6

urea

A

methyl N-methylcarbamate
6642-30-4

methyl N-methylcarbamate

B

methyl carbamate
598-55-0

methyl carbamate

C

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With ZnO-SrO at 170℃; for 6h; Reagent/catalyst; Temperature; Time;A 17%
B 55%
C 28%
With MgZn1.7Al hydrotalcite calcined at 450°C at 200℃; under 15001.5 Torr; for 4h; Catalytic behavior; Time; Autoclave;A 14%
B 28%
C 28%
(2E)-2,3-Diisopropyl-azimin-1-carbonsaeure-methylester
82317-28-0, 82317-30-4

(2E)-2,3-Diisopropyl-azimin-1-carbonsaeure-methylester

A

N-(1-Aethoxyaethyl)carbaminsaeure-methylester
27593-52-8

N-(1-Aethoxyaethyl)carbaminsaeure-methylester

B

methyl carbamate
598-55-0

methyl carbamate

C

trans-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

trans-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

D

cis-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

cis-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

Conditions
ConditionsYield
In diethyl ether at 12℃; Irradiation; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;A 7%
B n/a
C 31%
D n/a
In diethyl ether at 12℃; Irradiation; Yield given. Further byproducts given. Title compound not separated from byproducts;A 5%
B n/a
C 18%
D n/a
In diethyl ether at 12℃; Irradiation; Further byproducts given;A 5%
B n/a
C 18%
D n/a
In diethyl ether at 12℃; Irradiation; Further byproducts given. Yields of byproduct given;A 5%
B n/a
C 18%
D n/a
In diethyl ether at 12℃; Irradiation; Yield given. Further byproducts given;A 5%
B n/a
C 18%
D n/a
(2E)-2,3-Diisopropyl-azimin-1-carbonsaeure-methylester
82317-28-0, 82317-30-4

(2E)-2,3-Diisopropyl-azimin-1-carbonsaeure-methylester

A

methyl carbamate
598-55-0

methyl carbamate

B

2-Isopropyl-3-isopropyliden-triazan-1-carbonsaeure-methylester

2-Isopropyl-3-isopropyliden-triazan-1-carbonsaeure-methylester

C

trans-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

trans-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

D

cis-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

cis-2,3-Diisopropyl-triaziridin-1-carbonsaeure-methylester

Conditions
ConditionsYield
In diethyl ether at 12℃; Irradiation; Yield given. Further byproducts given;A n/a
B n/a
C 18%
D n/a
methanol
67-56-1

methanol

diethyl ether
60-29-7

diethyl ether

cyanic acid
420-05-3

cyanic acid

A

allophanic acid methyl ester
761-89-7

allophanic acid methyl ester

B

methyl carbamate
598-55-0

methyl carbamate

methanol
67-56-1

methanol

cyanic acid
420-05-3

cyanic acid

A

allophanic acid methyl ester
761-89-7

allophanic acid methyl ester

B

methyl carbamate
598-55-0

methyl carbamate

methanol
67-56-1

methanol

carbamic chloride
463-72-9

carbamic chloride

methyl carbamate
598-55-0

methyl carbamate

methanol
67-56-1

methanol

silver cyanate
3315-16-0

silver cyanate

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With hydrogen sulfide
With hydrogenchloride
methyl 1,1,1-trichloromethyl carbonate
101970-86-9

methyl 1,1,1-trichloromethyl carbonate

A

urea
57-13-6

urea

B

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With chloroform; ammonia
(-)-menthol
2216-51-5

(-)-menthol

cinnamoyl isocyanate
4737-20-6

cinnamoyl isocyanate

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
at 130℃;
dimethyl dicarbonate
4525-33-1

dimethyl dicarbonate

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With ethanol; ammonia
methanol
67-56-1

methanol

cyanogen chloride
506-77-4

cyanogen chloride

methyl carbamate
598-55-0

methyl carbamate

methanol
67-56-1

methanol

3,3-diisopropyl-azetidine-2,4-dione
17197-62-5

3,3-diisopropyl-azetidine-2,4-dione

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
Irradiation;
methanol
67-56-1

methanol

silyl isocyanate
13730-13-7

silyl isocyanate

methyl carbamate
598-55-0

methyl carbamate

3,3,3-Trifluor-2-chlor-2-nitro-propionsaeure-methylester
1683-76-7

3,3,3-Trifluor-2-chlor-2-nitro-propionsaeure-methylester

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
(i) NH3, Et2O, (ii) (heating); Multistep reaction;
1,2-bis(1-isocyanato-1-methylethyl)diazene
70678-13-6

1,2-bis(1-isocyanato-1-methylethyl)diazene

A

5,5-dimethyl-Δ1-1,2,4-triazolin-3-one
112700-85-3

5,5-dimethyl-Δ1-1,2,4-triazolin-3-one

B

methyl carbamate
598-55-0

methyl carbamate

C

2-methoxy-2-methoxycarbonylaminopropane

2-methoxy-2-methoxycarbonylaminopropane

D

[1-(1-Methoxycarbonylamino-1-methyl-ethylazo)-1-methyl-ethyl]-carbamic acid methyl ester

[1-(1-Methoxycarbonylamino-1-methyl-ethylazo)-1-methyl-ethyl]-carbamic acid methyl ester

Conditions
ConditionsYield
With methanol for 2h; Heating; Yield given;
phenoxysulfonyl-carbamic acid methyl ester
52200-01-8

phenoxysulfonyl-carbamic acid methyl ester

A

methanol
67-56-1

methanol

B

methyl carbamate
598-55-0

methyl carbamate

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
With hydrogen chloride In [D3]acetonitrile at 50℃; Rate constant; Thermodynamic data; other solvent; var. temp. and pH's; ΔH(excit.); ΔS(excit.); deuterium isotope effect;
(4-chloro-phenoxysulfonyl)-carbamic acid methyl ester
52200-06-3

(4-chloro-phenoxysulfonyl)-carbamic acid methyl ester

A

methanol
67-56-1

methanol

B

4-chloro-phenol
106-48-9

4-chloro-phenol

C

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With hydrogen chloride In [D3]acetonitrile at 50℃; Rate constant; Thermodynamic data; other solvent; var. temp. and pH's; ΔH(excit.); ΔS(excit.); deuterium isotope effect;
(4-nitro-phenoxysulfonyl)-carbamic acid methyl ester
92385-24-5

(4-nitro-phenoxysulfonyl)-carbamic acid methyl ester

A

methanol
67-56-1

methanol

B

4-nitro-phenol
100-02-7

4-nitro-phenol

C

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With hydrogen chloride In [D3]acetonitrile at 50℃; Rate constant; Thermodynamic data; other solvent; var. temp. and pH's; ΔH(excit.); ΔS(excit.); deuterium isotope effect;
methyl carbamate
598-55-0

methyl carbamate

methyl N-(sulfinylidene)carbamate
5659-91-6

methyl N-(sulfinylidene)carbamate

Conditions
ConditionsYield
Stage #1: methyl carbamate With thionyl chloride In diethyl ether at 0 - 20℃; for 0.583333h; Inert atmosphere;
Stage #2: With pyridine In diethyl ether at 20℃; for 3h; Inert atmosphere;
100%
With pyridine; thionyl chloride In diethyl ether at 0 - 25℃; for 3h;76%
With pyridine; thionyl chloride
With pyridine; thionyl chloride In diethyl ether at 0℃; for 3.5h; Inert atmosphere;
3-amino-5,5-dimethyl-8-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one
1022972-70-8

3-amino-5,5-dimethyl-8-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

methyl carbamate
598-55-0

methyl carbamate

(5,5-dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)carbamic acid methyl ester
1022945-76-1

(5,5-dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)carbamic acid methyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0833333h;100%
methyl carbamate
598-55-0

methyl carbamate

2-aminobenzoyl chloride
21563-73-5

2-aminobenzoyl chloride

2,4-dichloroquinazoline
607-68-1

2,4-dichloroquinazoline

Conditions
ConditionsYield
With pyridine; tetrachloromethane; titanium(IV) oxide; vanadia; tungsten(VI) oxide; tin(IV) oxide In N,N-dimethyl-formamide at 120 - 230℃; under 2250.23 - 6000.6 Torr; for 32h; Solvent; Temperature; Pressure; Reagent/catalyst;99.1%
(E)-1,3-diphenyl-2-propen-1-ol
62668-02-4

(E)-1,3-diphenyl-2-propen-1-ol

methyl carbamate
598-55-0

methyl carbamate

(E)-N-(1,3-diphenylallyl) methyl carbamate
33143-50-9

(E)-N-(1,3-diphenylallyl) methyl carbamate

Conditions
ConditionsYield
With potassium hexafluorophosphate; bismuth(lll) trifluoromethanesulfonate; calcium sulfate In 1,4-dioxane at 23 - 26℃; for 0.2h;99%
With aluminium(III) triflate In nitromethane at 20℃; for 0.166667h;94%
iso-propyl 2-(2-nitrophenyl)-4-oxobutanoate

iso-propyl 2-(2-nitrophenyl)-4-oxobutanoate

methyl carbamate
598-55-0

methyl carbamate

isopropyl 4-(methoxycarbonylamino)-2-(2-nitrophenyl)butanoate

isopropyl 4-(methoxycarbonylamino)-2-(2-nitrophenyl)butanoate

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In acetonitrile at 70℃; for 24h; Inert atmosphere;99%
triphenyl phosphite
101-02-0

triphenyl phosphite

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

methyl carbamate
598-55-0

methyl carbamate

methyl ((3-cyanophenyl)(diphenoxyphosphoryl)methyl)carbamate

methyl ((3-cyanophenyl)(diphenoxyphosphoryl)methyl)carbamate

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 16h; Oleksyszyn Synthesis;99%
4-methyl-N-(2-(1-methyl-1H-indol-3-yl)ethyl)-N-(phenylethynyl)benzenesulfonamide

4-methyl-N-(2-(1-methyl-1H-indol-3-yl)ethyl)-N-(phenylethynyl)benzenesulfonamide

methyl carbamate
598-55-0

methyl carbamate

methyl 1-methyl-5′-phenyl-1′-tosyl-2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridine]-2-yl carbamate

methyl 1-methyl-5′-phenyl-1′-tosyl-2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridine]-2-yl carbamate

Conditions
ConditionsYield
With silver trifluoromethanesulfonate; triphenylphosphine In toluene at 20℃; for 5h; Inert atmosphere; diastereoselective reaction;99%
N-methylene-tert-butylamine
13987-61-6

N-methylene-tert-butylamine

methyl carbamate
598-55-0

methyl carbamate

{[tert-Butyl-(methoxycarbonylamino-methyl)-amino]-methyl}-carbamic acid methyl ester
130157-99-2

{[tert-Butyl-(methoxycarbonylamino-methyl)-amino]-methyl}-carbamic acid methyl ester

Conditions
ConditionsYield
for 3h; Heating;98%
methyl carbamate
598-55-0

methyl carbamate

Glyoxilic acid
298-12-4

Glyoxilic acid

Hydroxy-methoxycarbonylamino-acetic acid
56674-26-1

Hydroxy-methoxycarbonylamino-acetic acid

Conditions
ConditionsYield
In diethyl ether98%
In diethyl ether98%
With water In diethyl ether98%
benzaldehyde
100-52-7

benzaldehyde

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

methyl N-(2-hydroxynaphthalen-1-yl)(phenyl)methyl carbamate

methyl N-(2-hydroxynaphthalen-1-yl)(phenyl)methyl carbamate

Conditions
ConditionsYield
With nano-silica-bonded 3-(n-propyl)-1-sulfoimidazolium chloride In neat (no solvent) at 70℃; for 0.216667h;98%
With saccharin sulfonic acid In neat (no solvent) at 70℃; for 0.166667h; Green chemistry;97%
With 4-methyl-4-sulfonic acid morpholinium chloride In neat (no solvent) at 100℃; for 0.05h; Reagent/catalyst;97%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

methyl N-(4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate

methyl N-(4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate

Conditions
ConditionsYield
With 4-methyl-4-sulfonic acid morpholinium chloride In neat (no solvent) at 100℃; for 0.0333333h; Catalytic behavior; Concentration; Solvent; Temperature;98%
With nano-silica-bonded 3-(n-propyl)-1-sulfoimidazolium chloride In neat (no solvent) at 70℃; for 0.216667h;97%
With graphene oxide supported imidazolium based dicationic ionic liquid at 80℃; for 0.0833333h;97%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

methyl ((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)carbamate
1071838-57-7

methyl ((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)carbamate

Conditions
ConditionsYield
With nano-silica-bonded 3-(n-propyl)-1-sulfoimidazolium chloride In neat (no solvent) at 70℃; for 0.133333h;98%
With trityl chloride In neat (no solvent) at 70℃; for 0.116667h;97%
With a magnetite (Fe3O4 )supported -SO3H functionalized benzimidazolium based ionic liquid In neat (no solvent) at 80℃; for 0.0666667h; Green chemistry;97%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

methyl N-(2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl carbamate
1071838-54-4

methyl N-(2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl carbamate

Conditions
ConditionsYield
With trityl chloride In neat (no solvent) at 70℃; for 0.133333h;98%
With nano-silica-bonded 3-(n-propyl)-1-sulfoimidazolium chloride In neat (no solvent) at 70℃; for 0.15h;98%
With saccharin sulfonic acid In neat (no solvent) at 70℃; for 0.166667h; Green chemistry;97%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

methyl ((3-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate
1071838-56-6

methyl ((3-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate

Conditions
ConditionsYield
With trityl chloride In neat (no solvent) at 70℃; for 0.0666667h;98%
With nano-silica-bonded 3-(n-propyl)-1-sulfoimidazolium chloride In neat (no solvent) at 70℃; for 0.2h;97%
With N,N,N-triethyl-N-sulfoethanammonium chloride at 110℃; for 0.166667h;94%
Methyl p-tolyl sulfoxide
934-72-5

Methyl p-tolyl sulfoxide

methyl carbamate
598-55-0

methyl carbamate

methyl[methyl(4-methylphenyl)oxido-λ6-sulfanylidene]carbamate

methyl[methyl(4-methylphenyl)oxido-λ6-sulfanylidene]carbamate

Conditions
ConditionsYield
With dirhodium tetraacetate; [bis(acetoxy)iodo]benzene; magnesium oxide In dichloromethane at 20 - 40℃; for 8h;98%
With dirhodium tetraacetate; [bis(acetoxy)iodo]benzene; magnesium oxide In dichloromethane at 40℃; for 8h;98%
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

methyl carbamate
598-55-0

methyl carbamate

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
With di-n-butyltin maleate In toluene for 3h; Reflux;98%
Cyclohex-2-enol
822-67-3

Cyclohex-2-enol

methyl carbamate
598-55-0

methyl carbamate

cyclohex-2-enyl carbamate
119449-77-3

cyclohex-2-enyl carbamate

Conditions
ConditionsYield
With di-n-butyltin maleate In toluene for 3h; Reflux;98%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

C19H16BrNO3

C19H16BrNO3

Conditions
ConditionsYield
With 4-methyl-4-sulfonic acid morpholinium chloride In neat (no solvent) at 100℃; for 0.05h; Reagent/catalyst;97%
With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate at 90℃; for 2h; Neat (no solvent);90%
With magnesium hydrogen sulfate In neat (no solvent) at 100℃; for 0.383333h; Green chemistry;90%
With 1-n-butyl-3-methylimidazolim bromide; toluene-4-sulfonic acid at 60℃; for 1h;75%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

methyl carbamate
598-55-0

methyl carbamate

dodecyl carbamate
6320-52-1

dodecyl carbamate

Conditions
ConditionsYield
With di-n-butyltin maleate In toluene for 3h; Reflux;97%
di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

methyl carbamate
598-55-0

methyl carbamate

1,1,3,3-tetrabutyl-1-methoxy-3-isocyanatodistannoxane

1,1,3,3-tetrabutyl-1-methoxy-3-isocyanatodistannoxane

Conditions
ConditionsYield
In methanol High Pressure; heating at 393-433 K in autoclave; MeOH was distilled off at 343-353 K, drying in vacuo at 333-343 K; elem.anal.;96.9%
methanol
67-56-1

methanol

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

methyl carbamate
598-55-0

methyl carbamate

1,6-bis(methoxycarbonylamino)hexane
6030-54-2

1,6-bis(methoxycarbonylamino)hexane

Conditions
ConditionsYield
With 5.1 wt% Ni/Fe3O4 at 190℃; under 11251.1 - 16501.7 Torr; for 5h; Autoclave; Inert atmosphere;96%
With cerium(IV) oxide at 150 - 210℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;96.9%
cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

methyl carbamate
598-55-0

methyl carbamate

N-(cyclohex-2-enyl) methyl carbamate
86766-64-5

N-(cyclohex-2-enyl) methyl carbamate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate; tetrakis(actonitrile)copper(I) hexafluorophosphate; 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane at 50℃; for 18h;96%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

methyl carbamate
598-55-0

methyl carbamate

β-naphthol
135-19-3

β-naphthol

methyl N-(4-bromophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate

methyl N-(4-bromophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate

Conditions
ConditionsYield
With N,N,N-triethyl-N-sulfoethanammonium chloride at 110℃; for 0.166667h;96%
With trityl chloride In neat (no solvent) at 70℃; for 0.133333h;95%
With saccharin sulfonic acid In neat (no solvent) at 70℃; for 0.0833333h; Green chemistry;95%
methanol
67-56-1

methanol

n-Dodecylamine
124-22-1

n-Dodecylamine

methyl carbamate
598-55-0

methyl carbamate

methyl n-dodecylcarbamate
66769-57-1

methyl n-dodecylcarbamate

Conditions
ConditionsYield
With 5.1 wt% Ni/Fe3O4 at 190℃; under 11251.1 - 16501.7 Torr; for 5h; Autoclave; Inert atmosphere;96%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

methyl carbamate
598-55-0

methyl carbamate

methyl (1-phenylethyl)carbamate
76926-67-5

methyl (1-phenylethyl)carbamate

Conditions
ConditionsYield
With aluminium(III) triflate In nitromethane at 50℃; for 0.166667h; Microwave irradiation;96%
1-(4-methylbenzensulfonyl)-4-(thien-3-yl)-1H-1,2,3-triazole

1-(4-methylbenzensulfonyl)-4-(thien-3-yl)-1H-1,2,3-triazole

methyl carbamate
598-55-0

methyl carbamate

(Z)-methyl (2-(4-methylphenylsulfonamido)-1-(thiophen-3-yl)vinyl)carbamate
1514928-15-4

(Z)-methyl (2-(4-methylphenylsulfonamido)-1-(thiophen-3-yl)vinyl)carbamate

Conditions
ConditionsYield
With rhodium(II) octanoate dimer In chloroform at 75℃; Inert atmosphere; Glovebox; Microwave irradiation; stereoselective reaction;96%
4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole
1078739-24-8

4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole

methyl carbamate
598-55-0

methyl carbamate

(Z)-methyl (1-(4-methoxyphenyl)-2-(4-methylphenylsulfonamido)vinyl)carbamate
1514928-17-6

(Z)-methyl (1-(4-methoxyphenyl)-2-(4-methylphenylsulfonamido)vinyl)carbamate

Conditions
ConditionsYield
With rhodium(II) octanoate dimer In chloroform at 75℃; Inert atmosphere; Glovebox; Microwave irradiation; stereoselective reaction;96%
p-methylbenzaldoxime methyl ether
70286-36-1

p-methylbenzaldoxime methyl ether

methyl carbamate
598-55-0

methyl carbamate

[2-(methoxyimino-methyl)-5-methyl-phenyl]-carbamic acid methyl ester

[2-(methoxyimino-methyl)-5-methyl-phenyl]-carbamic acid methyl ester

Conditions
ConditionsYield
Stage #1: p-methylbenzaldoxime methyl ether; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 1h;
Stage #2: methyl carbamate With dipotassium peroxodisulfate In 1,2-dichloro-ethane at 80℃;
95%

598-55-0Relevant articles and documents

CH3COONa as an effective catalyst for methoxycarbonylation of 1,6-hexanediamine by dimethyl carbonate to dimethylhexane-1,6-dicarbamate

Sun, Da-Lei,Xie, Shun-Ji,Deng, Jian-Ru,Huang, Cai-Juan,Ruckenstein, Eli,Chao, Zi-Sheng

, p. 483 - 490 (2010)

Methoxycarbonylation of 1,6-hexanediamine (HDA) by dimethyl carbonate (DMC) was carried out, using, for the first time, CH3COONa as catalyst. The effects of the solvent, reaction temperature, reaction time, and catalyst amount, were investigated. A yield as high as 99.0% of dimethylhexane-1,6- dicarbamate 2 has been obtained at a temperature of 348 K and a reaction time of 6 h. Mechanistic studies revealed that N-substituted acetamide, as the active intermediate product, and NaOH were first formed via the reaction between HDA and CH3COONa. A further reaction between the N-substituted acetamide and DMC generated carbamates and methyl acetate, via a hexatomic ring intermediate. The CH3COONa catalyst was finally recovered through the reaction between NaOH and methyl acetate, which thus completed the catalytic cycle.

Synthesis of dimethyl carbonate from methanol and urea over zinc-strontia mixed oxide catalysts

D., Dhana Lakshmi,B., Srinivasa Rao,Lingaiah

, p. 1 - 4 (2019)

A series of ZnO-SrO mixed oxide catalysts were prepared by co-precipitation with different compositions and tested for dimethyl carbonate synthesis from urea and methanol. The catalysts were characterized by BET surface area, XRD, NH3-TPD and CO2-TPD. The catalyst with 1:1 mol ratio exhibited high DMC yield of 35%. The uniform distributions of moderate to strong basic sites along with considerable number of acidic sites are accountable for high activity. Different reaction parameters were also screened and best possible conditions were established. The catalyst was easily recovered and reused with consistent activity.

Dimethyl carbonate synthesis over ZnO-CaO bi-functional catalysts

Wu, Xiaomin,Kang, Min,Zhao, Ning,Wei, Wei,Sun, Yuhan

, p. 46 - 50 (2014)

ZnO-CaO catalysts were prepared and tested for the synthesis of dimethyl carbonate (DMC) from urea and methanol. Meaningfully, the bi-functional catalysts ZnO-CaO exhibited noticeable DMC yield (41.2%) with the Zn/Ca molar ratio of 4:1, which might ascribe to the synergistic effect between ZnO and CaO. The plausible mechanism for the DMC synthesis was as follows: urea was activated to generate metal isocyanato group on the acid sites and subsequently nucleophilic attacked by the activated methanol on the basic sites.

Carbamate preparation method

-

Paragraph 0026-0046, (2020/03/12)

The invention relates to a carbamate preparation method. According to the invention, dimethyl carbonate is used as a reaction raw material for urea alcoholysis, and a novel composite catalyst is used,so that the technical problems of high energy consumption and high equipment cost caused by cold energy ammonia removal in the prior art are avoided, and the yield of carbamate is up to more than 96%.

Preparation method of carbamate

-

Paragraph 0034; 0038-0040, (2020/09/23)

The invention belongs to the technical field of synthesis of amino and carboxyl compounds connected to the same carbon frame through urea alcoholysis, and particularly relates to a preparation methodof carbamate. The preparation method of the carbamate comprises the following steps of: sequentially introducing urea, alcohol and a catalyst into a reactor, sealing, and reacting at 90-120 DEG C for8-12 hours to obtain the carbamate, wherein the catalyst includes an alumina supported metal oxide. By adopting the method for preparation of the carbamate, the side reaction of urea decomposition canbe effectively avoided, impurities such as carbamate are not detected, and the yield of the carbamate is high.

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