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691-24-7 Usage

Uses

N,N′-Di-tert-butylcarbodiimide can be used:As a reagent for the guanylation of aryl amines catalyzed by lanthanum amides.To prepare dichloroimidazolidine-4,5-dione by reacting with oxalyl chloride, which is a key intermediate for the synthesis of N,N′-diamidocarbenes.To prepare the iridium complex of benzamidine named Ir(FMeppy)2(N,N′-di-tert-butyl-4-methyl-benzamidine).

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 7047, 1996 DOI: 10.1016/0040-4039(96)01593-6

Check Digit Verification of cas no

The CAS Registry Mumber 691-24-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 1 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 691-24:
(5*6)+(4*9)+(3*1)+(2*2)+(1*4)=77
77 % 10 = 7
So 691-24-7 is a valid CAS Registry Number.

691-24-7 Well-known Company Product Price

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  • Aldrich

  • (235563)  N,N′-Di-tert-butylcarbodiimide  99%

  • 691-24-7

  • 235563-1G

  • 772.20CNY

  • Detail
  • Aldrich

  • (235563)  N,N′-Di-tert-butylcarbodiimide  99%

  • 691-24-7

  • 235563-5G

  • 2,669.94CNY

  • Detail

691-24-7SDS

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'-ditert-butylmethanediimine

1.2 Other means of identification

Product number -
Other names N,N'-di-tert-Butylcarbodiimide

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:691-24-7 SDS

691-24-7Synthetic route

2,4-di-tert-butyl-1,3-bis-tert-butylimino-1λ4,3λ4-[1,3,2,4]ditelluradiazetidine

2,4-di-tert-butyl-1,3-bis-tert-butylimino-1λ4,3λ4-[1,3,2,4]ditelluradiazetidine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

2,4-di-tert-butyl-1-oxo-1λ4-[1,2,4]telluradiazetidin-3-one

2,4-di-tert-butyl-1-oxo-1λ4-[1,2,4]telluradiazetidin-3-one

Conditions
ConditionsYield
In tetrahydrofuran; hexane at 23℃; for 1.5h; Cycloaddition;A n/a
B 99%
N,N-di-tert-butylthiourea
4041-95-6

N,N-di-tert-butylthiourea

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide In benzene at 60 - 65℃; for 4h; Temperature; Large scale;94%
With 1,1'-Thiocarbonyldi-2(1H)-pyridone In toluene for 1.5h; Heating;90%
With sodium hypochlorite; Petroleum ether
N,N-di-tert-butylthiourea
4041-95-6

N,N-di-tert-butylthiourea

A

2-hydroxypyridin
142-08-5

2-hydroxypyridin

B

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile for 6h; Ambient temperature;A n/a
B 92%
1,3-di-tert-butylurea
5336-24-3

1,3-di-tert-butylurea

triphenylphosphine
603-35-0

triphenylphosphine

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With aluminum oxide In dichloromethane constant current electrolysis;A 91%
B n/a
With aluminum oxide; LutClO4 constant current electrolysis;A 91%
B n/a
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

tert-butylamine
75-64-9

tert-butylamine

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

1,3-di-tert-butylurea
5336-24-3

1,3-di-tert-butylurea

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 20℃; Reagent/catalyst; Temperature;A 10%
B 90%
With oxygen; sodium carbonate; palladium diacetate at 100℃; under 2068.6 Torr; for 3h;A 31%
B 30 % Chromat.
1,3-di-tert-butylurea
5336-24-3

1,3-di-tert-butylurea

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With dichloromethylenedimethyliminium chloride; triethylamine In dichloromethane at 0℃;85%
With potassium carbonate; 4-bromobenzenesulfonyl chloride; N-benzyl-N,N,N-triethylammonium chloride In chloroform for 13h; Heating; Yield given;
(chloro)2(η5-C5Me5)(tert-butylimido)tantalum

(chloro)2(η5-C5Me5)(tert-butylimido)tantalum

N-tert-butyl-N'-(2,6-diisopropylphenyl)carbodiimide
104962-00-7

N-tert-butyl-N'-(2,6-diisopropylphenyl)carbodiimide

A

(η(5)-pentamethylcyclopentadienyl)TaCl2(NC6H3Me2-2,6)

(η(5)-pentamethylcyclopentadienyl)TaCl2(NC6H3Me2-2,6)

B

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
In benzene-d6 heated at 190 ° C under Ar for 10 h; (1)H NMR monitoring; not isolated, yield given by NMR;A n/a
B 80%
(1,2-di-tert-butyldiaziridin-3-ylidene)(methyl)amine

(1,2-di-tert-butyldiaziridin-3-ylidene)(methyl)amine

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With sodium hydride In cyclohexane at 180℃; for 0.583333h;A n/a
B 32%
1,2-Di-tert-butyl-3-(cyanimino)diaziridine
78822-78-3

1,2-Di-tert-butyl-3-(cyanimino)diaziridine

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
In toluene at 100℃; for 3h;18%
t-butylnitrite
917-95-3

t-butylnitrite

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

1,3-di-tert-butylurea
5336-24-3

1,3-di-tert-butylurea

C

azo-t-butane
15464-01-4

azo-t-butane

D

2,2'-dimethyl-2,2'-azoxypropane
16649-52-8, 54168-23-9, 87339-11-5

2,2'-dimethyl-2,2'-azoxypropane

Conditions
ConditionsYield
With iron pentacarbonyl In tetrahydrofuran for 1h; Irradiation;A 1%
B 13%
C 1%
D 4%
iron pentacarbonyl
13463-40-6

iron pentacarbonyl

t-butylnitrite
917-95-3

t-butylnitrite

A

di-t-butyldiazene
927-83-3

di-t-butyldiazene

B

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

C

1,3-di-tert-butylurea
5336-24-3

1,3-di-tert-butylurea

D

di-t-butyldiazene N-oxide
16649-52-8, 54168-23-9, 87339-11-5

di-t-butyldiazene N-oxide

Conditions
ConditionsYield
In tetrahydrofuran Irradiation (UV/VIS); Stirring of nitroso compound in THF under N2, metal carbonyl in THF is added, the soln. is irradiated for 1 h (sunlamp photolysis) at 30°C.; addn. of naphthalene as internal standard, Gc-anal.;A 1%
B 1%
C 13%
D 4%
N,N'-Di-tert.-butyl-isothioharnstoff-S-methylaether
91015-60-0

N,N'-Di-tert.-butyl-isothioharnstoff-S-methylaether

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
at 150℃;
N-(1,3,2-dioxaboryl-2-yl)N-phenyl-N'-t-butylurea
98220-98-5

N-(1,3,2-dioxaboryl-2-yl)N-phenyl-N'-t-butylurea

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
at 190℃; under 12 Torr;
N,N'-di-tert-butyldiaziridinone
19656-74-7

N,N'-di-tert-butyldiaziridinone

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With 1,2-di-tert-butylhydrazine In benzene
1,3-Di-tert.-butyl-guanidinium-chlorid

1,3-Di-tert.-butyl-guanidinium-chlorid

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
(i) aq. NaOCl, Et2O, (ii) aq. NaOH, MeOH; Multistep reaction;
triphenylphosphine-N-tertbutylimine
13989-64-5

triphenylphosphine-N-tertbutylimine

1,1-dimethyl-4-tert-butyl-3,5-dioxo-1,2,4-triazolidinium hydroxide inner salt
54930-99-3

1,1-dimethyl-4-tert-butyl-3,5-dioxo-1,2,4-triazolidinium hydroxide inner salt

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
In benzene
Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With 1-ethyl-3-methyl-2,5-dihydro-1H-phosphole oxide In tetralin Heating;
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

tert-butylamine
75-64-9

tert-butylamine

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With iodine; oxygen; sodium carbonate; palladium diacetate at 100℃; under 2068.6 Torr; for 3h;86 % Chromat.
trimethyl(tert-butylamino)silane
5577-67-3

trimethyl(tert-butylamino)silane

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With n-butyllithium; tin(ll) chloride Yield given. Multistep reaction;
N,N'-di-tert-butylselenourea
423767-51-5

N,N'-di-tert-butylselenourea

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 5h; Heating; Yield given;
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Se, DBU / tetrahydrofuran / 1 h / Heating
2: DBU, O2 / tetrahydrofuran / 5 h / Heating
View Scheme
C10H20N4
78822-76-1

C10H20N4

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / t-BuOCl, t-BuOK / CCl4 / 3 h / -75 °C
2: 18 percent / toluene / 3 h / 100 °C
View Scheme
(tert-butyl)(1-tert-butyl-2-methyldiaziridin-3-ylidene)amine
23044-57-7, 61483-95-2

(tert-butyl)(1-tert-butyl-2-methyldiaziridin-3-ylidene)amine

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

hexamethylenetetramine
100-97-0

hexamethylenetetramine

Conditions
ConditionsYield
With sodium hydride In cyclohexane at 180℃; for 0.583333h;
N',N
1189055-47-7

N',N"-di(tert-butyl)-N-methyl-N-hydroxyguanidine O-sulfonic acid

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

(tert-butyl)(1-tert-butyl-2-methyldiaziridin-3-ylidene)amine
23044-57-7, 61483-95-2

(tert-butyl)(1-tert-butyl-2-methyldiaziridin-3-ylidene)amine

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at -25 - 20℃;
tetrakis(dimethylamido)zirconium (IV)
19756-04-8

tetrakis(dimethylamido)zirconium (IV)

C20H26FeN4

C20H26FeN4

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

C19H32FeN6Zr

C19H32FeN6Zr

Conditions
ConditionsYield
In benzene-d6 at 75℃;
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

Azobenzene
1227476-15-4

Azobenzene

A

N-((tert-butylimino)methylene)aniline
2219-34-3

N-((tert-butylimino)methylene)aniline

B

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Conditions
ConditionsYield
With 4C5H5N*2Ti(4+)*4Br(1-)*2C4H9N(2-) at 115℃; for 24h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube;A 85 %Spectr.
B 12 %Spectr.
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

bis-(4-fluorophenyl)diazene
332-07-0, 51788-93-3, 51789-00-5

bis-(4-fluorophenyl)diazene

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

N-((tert-butylimino)methylene)-4-fluoroaniline

N-((tert-butylimino)methylene)-4-fluoroaniline

Conditions
ConditionsYield
With 4C5H5N*2Ti(4+)*4Br(1-)*2C4H9N(2-) at 115℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;A 8 %Spectr.
B 70 %Spectr.
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

bis-(4-chloro-phenyl)-diazene
1602-00-2

bis-(4-chloro-phenyl)-diazene

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

N-((tert-butylimino)methylene)-4-chloroaniline

N-((tert-butylimino)methylene)-4-chloroaniline

Conditions
ConditionsYield
With 4C5H5N*2Ti(4+)*4Br(1-)*2C4H9N(2-) at 115℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;A 8 %Spectr.
B 70 %Spectr.
4,4′-bis(trifluoromethoxy)azobenzene

4,4′-bis(trifluoromethoxy)azobenzene

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

tert-butylisonitrile

A

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

B

C12H13F3N2O

C12H13F3N2O

Conditions
ConditionsYield
With 4C5H5N*2Ti(4+)*4Br(1-)*2C4H9N(2-) at 115℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;A 7 %Spectr.
B 71 %Spectr.
oxalyl dichloride
79-37-8

oxalyl dichloride

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

1,3-di-tert-butyl-2,2-dichloroimidazolidine-4,5-dione
26262-88-4

1,3-di-tert-butyl-2,2-dichloroimidazolidine-4,5-dione

Conditions
ConditionsYield
In dichloromethane at 0 - 23℃; for 1h; Schlenk technique; Inert atmosphere;99%
In diethyl ether at 0 - 20℃; for 48h; Inert atmosphere; Schlenk technique;99%
In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique;92%
In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

(E)-N,N′-di-tert-butyl-N-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)formimidamide

(E)-N,N′-di-tert-butyl-N-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)formimidamide

Conditions
ConditionsYield
With C42H56AlN5 In neat (no solvent) at 70℃; for 12h; Sealed tube;99%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

boron trichloride
10294-34-5

boron trichloride

phenyllithium
591-51-5

phenyllithium

C15H23BCl2N2

C15H23BCl2N2

Conditions
ConditionsYield
Stage #1: 1,3-di-tert-butylcarbodiimide; phenyllithium In diethyl ether; toluene at -78 - 20℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: boron trichloride In diethyl ether; hexane; toluene at -78 - 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;
98.4%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

C15H31BN2O2

C15H31BN2O2

Conditions
ConditionsYield
With C37H59AlN2 In neat (no solvent) at 60℃; for 10h; Inert atmosphere;98%
With [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu] In benzene-d6 at 80℃; for 60h; Glovebox; Inert atmosphere; Sealed tube;87%
With 9-borabicyclo[3.3.1]nonane dimer In benzene-d6 at 60℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;60%
With C23H31AlN2 In neat (no solvent) at 80℃; for 60h; Temperature; Inert atmosphere; Sealed tube;69 %Spectr.
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

aniline
62-53-3

aniline

N-phenyl-N',N''-di-tert-butylguanidine

N-phenyl-N',N''-di-tert-butylguanidine

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate In benzene-d6 at 80℃; for 8h; In air; Sealed tube;96%
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 4h;93%
With C23H40AlN In toluene at 25℃; for 1h; Inert atmosphere; Schlenk technique;82%
4-n-chlorophenylacetylene
873-73-4

4-n-chlorophenylacetylene

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

(E)-N,N'-di-tert-butyl-3-(4-chlorophenyl)propiolamidine

(E)-N,N'-di-tert-butyl-3-(4-chlorophenyl)propiolamidine

Conditions
ConditionsYield
With [Y((CH3)4C5Si(CH3)2N(phenyl))(trimethylsilylmethyl)(tetrahydrofuran)2] In toluene at 110℃; for 1h;95%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(p-chlorophenyl)-N',N''-di-tert-butylguanidine

N-(p-chlorophenyl)-N',N''-di-tert-butylguanidine

Conditions
ConditionsYield
[Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 4h;95%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

p-toluidine
106-49-0

p-toluidine

N-(p-methylphenyl)-N',N''-di-tert-butylguanidine

N-(p-methylphenyl)-N',N''-di-tert-butylguanidine

Conditions
ConditionsYield
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 4h;95%
With C23H40AlN In toluene at 25℃; for 1h; Inert atmosphere; Schlenk technique;89%
With zinc(II) oxide In toluene at 80℃; for 8h;86%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Zn2H2((2,4,6-Me3C6H2)NC(Me))2CH)2
1234094-51-9

Zn2H2((2,4,6-Me3C6H2)NC(Me))2CH)2

Zn(tBuNCHNtBu)[(2,4,6-Me3C6H2)NC(Me)]2CH)
1403459-35-7

Zn(tBuNCHNtBu)[(2,4,6-Me3C6H2)NC(Me)]2CH)

Conditions
ConditionsYield
In tetrahydrofuran nuder Ar; soln. of tBuNCNtBu in THF added to Zn complex in THF; stirred at ambient temp.; solvent evapd. in vacuo; elem. anal.;95%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

2,4-dinitrobenzoic acid
610-30-0

2,4-dinitrobenzoic acid

(1,3-di-tert-butyl-6-nitro-2,4-dioxo-1,3-diazaspiro-[4.5]deca-6,9-dien-1-ium-8-ylidene)azinate

(1,3-di-tert-butyl-6-nitro-2,4-dioxo-1,3-diazaspiro-[4.5]deca-6,9-dien-1-ium-8-ylidene)azinate

Conditions
ConditionsYield
Stage #1: 1,3-di-tert-butylcarbodiimide; 2,4-dinitrobenzoic acid In dichloromethane at 20℃; for 0.5h;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;
95%
Dichloromethylsilane
75-54-7

Dichloromethylsilane

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

phenyllithium
591-51-5

phenyllithium

C16H27ClN2Si

C16H27ClN2Si

Conditions
ConditionsYield
Stage #1: 1,3-di-tert-butylcarbodiimide; phenyllithium In diethyl ether; toluene at -78 - 20℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: Dichloromethylsilane In diethyl ether; toluene at -78 - 20℃; for 16h; Inert atmosphere; Schlenk technique; Glovebox;
94.6%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

phenylacetylene
536-74-3

phenylacetylene

(E)-N,N'-di-tert-butyl-3-phenylpropiolamidine

(E)-N,N'-di-tert-butyl-3-phenylpropiolamidine

Conditions
ConditionsYield
With [Y((CH3)4C5Si(CH3)2N(phenyl))(trimethylsilylmethyl)(tetrahydrofuran)2] In toluene at 110℃; for 1h;94%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

(E)-N,N'-di-tert-butyl-3-p-tolylpropiolamidine

(E)-N,N'-di-tert-butyl-3-p-tolylpropiolamidine

Conditions
ConditionsYield
With [Y((CH3)4C5Si(CH3)2N(phenyl))(trimethylsilylmethyl)(tetrahydrofuran)2] In toluene at 110℃; for 1h;94%
formic acid
64-18-6

formic acid

iodobenzene
591-50-4

iodobenzene

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

N-t-butylbenzamide
5894-65-5

N-t-butylbenzamide

Conditions
ConditionsYield
With palladium diacetate; 1,3-bis(mesityl)imidazolium chloride In toluene at 150℃; for 6h;94%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

p-trifluoromethylphenylchlorohydrazone
1315307-30-2

p-trifluoromethylphenylchlorohydrazone

methyl 1-[4-(trifluoromethyl)phenyl]-5-(tert-butylamino)-1H-1,2,4-triazole-3-carboxylate

methyl 1-[4-(trifluoromethyl)phenyl]-5-(tert-butylamino)-1H-1,2,4-triazole-3-carboxylate

Conditions
ConditionsYield
With triethylamine In toluene for 5h; Inert atmosphere; Reflux;93%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

diethylaluminium chloride
96-10-6

diethylaluminium chloride

(CH3CH2)2Al(N(C(CH3)3)C(Cl)N(C(CH3)3))
204003-64-5

(CH3CH2)2Al(N(C(CH3)3)C(Cl)N(C(CH3)3))

Conditions
ConditionsYield
In diethyl ether; hexane N2-atmosphere; 2 equiv. of carbodiimide; stirring (room temp., 8 h); solvent removal (vac.);92%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

Trifluoromethanesulfonamide
421-85-2

Trifluoromethanesulfonamide

N-(bis(tert-butylamino)methylene)-1,1,1-trifluoromethanesulfonamide

N-(bis(tert-butylamino)methylene)-1,1,1-trifluoromethanesulfonamide

Conditions
ConditionsYield
With nitromethane; copper dichloride for 2h; Milling; Green chemistry;92%
bis(trimethylsilyl)acetylenetitanocene

bis(trimethylsilyl)acetylenetitanocene

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

(cyclopentadienyl)2Ti(κ2-tBuNCNtBu)

(cyclopentadienyl)2Ti(κ2-tBuNCNtBu)

Conditions
ConditionsYield
In pentane at 25℃; for 0.166667h; Inert atmosphere; Glovebox; Sealed tube;92%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

(1-Naphthylphenylmethylene)ammonium Hexachloroantimonate

(1-Naphthylphenylmethylene)ammonium Hexachloroantimonate

N,N'-di-tert-butyl-N

N,N'-di-tert-butyl-N"-(α-naphthylphenylmethylene)guanidinium hexachloroantimonate

Conditions
ConditionsYield
In dichloromethane at 22℃;90%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

phenylacetylene
536-74-3

phenylacetylene

C29H32N2
1610032-14-8

C29H32N2

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 20℃; for 9h; Inert atmosphere; regioselective reaction;90%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

methyl 2-chloro-2-(2-phenylhydrazono)acetate
58131-64-9

methyl 2-chloro-2-(2-phenylhydrazono)acetate

methyl 1-phenyl-5-(tert-butylamino)-1H-1,2,4-triazole-3-carboxylate

methyl 1-phenyl-5-(tert-butylamino)-1H-1,2,4-triazole-3-carboxylate

Conditions
ConditionsYield
With triethylamine In toluene for 5h; Inert atmosphere; Reflux;89%
Moore's ketene
29342-22-1

Moore's ketene

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

1,3-Di-tert-butyl-2-[(Z)-tert-butylimino]-4-oxo-azetidine-3-carbonitrile

1,3-Di-tert-butyl-2-[(Z)-tert-butylimino]-4-oxo-azetidine-3-carbonitrile

Conditions
ConditionsYield
In benzene Heating;88%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

(Diphenylmethylene)ammonium Hexachloroantimonate

(Diphenylmethylene)ammonium Hexachloroantimonate

N,N'-di-tert-butyl-N

N,N'-di-tert-butyl-N"-(diphenylmethylene)guanidinium hexachloroantimonate

Conditions
ConditionsYield
In dichloromethane at 22℃;88%
tetrahydrofuran
109-99-9

tetrahydrofuran

1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

lithium tert-butylamide
37828-54-9

lithium tert-butylamide

2C13H28N3(1-)*C4H8O*2Li(1+)

2C13H28N3(1-)*C4H8O*2Li(1+)

Conditions
ConditionsYield
-78 deg C, 0.5 h, -78 deg C to 23 deg C;88%
1,3-di-tert-butylcarbodiimide
691-24-7

1,3-di-tert-butylcarbodiimide

2,4-dinitrobenzoic acid
610-30-0

2,4-dinitrobenzoic acid

N-(tert-butyl)-N-(tert-butylcarbamoyl)-2,4-dinitrobenzamide

N-(tert-butyl)-N-(tert-butylcarbamoyl)-2,4-dinitrobenzamide

Conditions
ConditionsYield
In dichloromethane at 20℃;88%

691-24-7Relevant articles and documents

Cycloaddition reaction of tert-butyl isocyanate and a tellurium diimide dimer: Extended helical structure of the ureato telluroxide {[OC(μ-NBu(t))2TeO]2(thf)}∞

Schatte,Chivers,Jaska,Sandblom

, p. 1657 - 1658 (2000)

The reaction of Bu(t)NTe(μ-NBu(t))2TeNBu(t) with Bu(t)NCO in a 1:4 molar ratio in thf produces N,N'-bis(tert-butyl)ureato telluroxide dimers [OC(μ-NBu(t))2TeO]2, which form an extended helical network via weak >C=O···Te interactions.

Method of producing N,N'-ditertiary butyl dicarbodiimide by thiourea method

-

Paragraph 0026-0040, (2019/03/08)

The invention belongs to the technical field of organic synthesis, and in particular relates to a method of producing N,N'-ditertiary butyl dicarbodiimide by a thiourea method. The method comprises the following steps: first, synthesizing N,N'-ditertiary butyl thiourea in a water medium by using tert-butylamine and carbon disulfide; carrying out suction filtration on the N,N'-ditertiary butyl thiourea, drying, carrying out primary oxidization, successively adding the mixture, caustic soda flakes, a solvent and a catalyst into a reaction kettle, heating the mixture to 60-65 DEG C, adding an oxidizing agent to react for 2 hours at 60-65 DEG C, leaving the product to stand for 20-25 minutes, and abandoning a lower water phase; carrying out secondary oxidizing reaction, dropwise adding quantitative oxidizing agent and catalyst, and carrying out a reaction for 1 hour at 65 DEG C; and adding alkali to neutralize, washing with water, separating a water layer, distilling the solvent out, and carrying out rectification at a reduced pressure to obtain N,N'-ditertiary butyl dicarbodiimide. The method of producing N,N'-ditertiary butyl dicarbodiimide by the thiourea method is mild in reactioncondition, high in yield, high in purity and simple in post-treatment, and process water can be recycled.

Synthesis of 2-aminobenzoxazoles and 3-aminobenzoxazines via palladium-catalyzed aerobic oxidation of o -aminophenols with isocyanides

Liu, Bifu,Yin, Meizhou,Gao, Hanling,Wu, Wanqing,Jiang, Huanfeng

supporting information, p. 3009 - 3020 (2013/06/26)

A Pd-catalyzed aerobic oxidation of o-aminophenols and isocyanides for the synthesis of 2-aminobenzoxazoles and 3-aminobenzoxazines has been achieved in an air atmosphere. The procedure constructs 2-aminobenzoxazoles and 3-aminobenzoxazines with moderate to excellent yields and a broad substrate scope. Apart from experimental simplicity, this methodology has the advantages of mild reaction conditions and easily accessible starting materials. Furthermore, the utility of this method has also been successfully applied to the synthesis of other types of useful nitrogen heterocycles.

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