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1609-86-5

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1609-86-5 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 1609-86-5 differently. You can refer to the following data:
1. Clear colorless liquid
2. A clear, colorless, flammable liquid. Pungent odor.

Uses

t-Butyl Isocyanate is a useful intermediate in synthesizing SCH 503034, a potential drug in the treatment of Hepatitis C virus. The study discusses with data the drug inhibitive selectivity against the viral enzyme NS3 Protease.

General Description

A clear colorless liquid with a pungent odor. Flash point 68°F. Very toxic by ingestion, may also be toxic by skin absorption and inhalation. Vapors heavier than air. Less dense than water and insoluble in water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.

Air & Water Reactions

Highly flammable. May react with water to produce a toxic vapor. Very slowly decomposed by water.

Reactivity Profile

tert-Butylisocyanate can react exothermically with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizing agents, hydrides, phenols, and peroxides. May undergo polymerization with acids and bases. May react with water to form tert-butylamine and carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Potential Exposure

tert-Butyl isocyanate is used as a reagent in organic synthesis; used as intermediates in production of pharmaceuticals and other chemicals

Shipping

UN2484 tert-Butyl isocyanate, Hazard class: 6.1; Labels: 6.1—Poison Inhalation Hazard, 3—Flammable liquid. Inhalation Hazard Zone A. PGI

Purification Methods

It is LACHRYMATORY and TOXIC, and should have IR with 2251 (CN) cm-1 and no OH bands. The NMR should have one band at 1.37 ppm from TMS. Purify it by fractional distillation under reduced pressure. [Greene & Bergmark J Org Chem 36 3056 1971, Curtius J Prakt Chem 125 152 1930, Beilstein 4 IV 669.]

Incompatibilities

Highly flammable liquid and vapor; forms explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flammable gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the concentration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acyl-chlorides may cause explosive polymerization. Attacks some plastics, rubber and coatings. Contact with metals may evolve flammable hydrogen gas. May accumulate static electrical charges, and may cause ignition of its vapors

Waste Disposal

Dispose of contents and container to an approved waste disposal plant. Use a licensed professional waste disposal service to dispose of this material. Caution: this chemical is highly flammable with a very low flash point (23.5C). Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 1609-86-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,0 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1609-86:
(6*1)+(5*6)+(4*0)+(3*9)+(2*8)+(1*6)=85
85 % 10 = 5
So 1609-86-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO/c1-5(2,3)6-4-7/h1-3H3

1609-86-5 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (L13371)  tert-Butyl isocyanate, 97%   

  • 1609-86-5

  • 5g

  • 144.0CNY

  • Detail
  • Alfa Aesar

  • (L13371)  tert-Butyl isocyanate, 97%   

  • 1609-86-5

  • 25g

  • 486.0CNY

  • Detail
  • Alfa Aesar

  • (L13371)  tert-Butyl isocyanate, 97%   

  • 1609-86-5

  • 100g

  • 1519.0CNY

  • Detail

1609-86-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-Butylisocyanate

1.2 Other means of identification

Product number -
Other names Isocyanic Acid tert-Butyl Ester

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:1609-86-5 SDS

1609-86-5Synthetic route

Cp*Mo[N(iPr)C(Me)N(iPr)](NtBu)

Cp*Mo[N(iPr)C(Me)N(iPr)](NtBu)

[13C]Carbon monoxide
1641-69-6

[13C]Carbon monoxide

A

(η5-C5Me5)*Mo{N(iPr)C(Me)N(iPr)}(CO)2
1241890-64-1

(η5-C5Me5)*Mo{N(iPr)C(Me)N(iPr)}(CO)2

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In benzene-d6 at 25℃; for 96h;A 100%
B n/a
carbon dioxide
124-38-9

carbon dioxide

1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene)
165535-45-5

1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene)

A

Bis(dimethylamino)<amino>phosphane oxide
91241-12-2

Bis(dimethylamino)phosphane oxide

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In benzene-d6 at 60℃; under 760.051 Torr; for 12h; Schlenk technique; Sealed tube; Inert atmosphere;A 99%
B n/a
(t-C4H9NC)2NiOCNC4H9-t

(t-C4H9NC)2NiOCNC4H9-t

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

tert-butylisonitrile

A

tetrakis(tert-n-butylisocyanide)nickel(0)
19068-11-2

tetrakis(tert-n-butylisocyanide)nickel(0)

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In toluene react. with excess t-C4H9NCO in toluene at room temp.;;A n/a
B 98%
In toluene react. with excess t-C4H9NCO in toluene at room temp.;;A n/a
B 98%
phosgene
75-44-5

phosgene

tert-butylamine
75-64-9

tert-butylamine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In chlorobenzene at 335 - 345℃; under 0 Torr;97.9%
1,3-di-tert-butylurea
5336-24-3

1,3-di-tert-butylurea

A

tert-Butyl-(dichloro-phenyl-silanyl)-amine

tert-Butyl-(dichloro-phenyl-silanyl)-amine

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With Phenyltrichlorosilane at 130 - 170℃; for 3.5h;A n/a
B 96.4%
tert-butylaminoformyl chloride

tert-butylaminoformyl chloride

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With pyridine; N-Methylpyrrole; toluene-4-sulfonic acid; triethylamine; citric acid In chlorobenzene at 110℃; for 13h; Solvent; Temperature;94%
(chloro)2(η5-C5Me5)(tert-butylimido)tantalum

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

carbon dioxide
124-38-9

carbon dioxide

A

{Cp*3Ta3(μ2-O)3(μ3-O)(μ-Cl)Cl3}

{Cp*3Ta3(μ2-O)3(μ3-O)(μ-Cl)Cl3}

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In benzene-d6 a soln. of Ta-complex in C6D6 was heated at 140 ° C under CO2 for 12 h; (1)H NMR monitoring; not isolated, yields given by NMR;A 78%
B 92%
2-(tert-butylamino)-2-oxoacetic acid
169772-25-2

2-(tert-butylamino)-2-oxoacetic acid

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate; copper(II) sulfate In hexane; water at 40℃; for 3h;85%
With ammonium peroxydisulfate; copper diacetate; silver nitrate In hexane; water at 40℃; for 3h;85%
carbon dioxide
124-38-9

carbon dioxide

tert-butylamine
75-64-9

tert-butylamine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at -78 - 20℃; under 760 Torr;84%
With di-isopropyl azodicarboxylate; triphenylphosphine 1.) dichloromethane, -5 deg C to -10 deg C, 2.) dichloromethane, -78 deg C, ambient temp.; Yield given; Multistep reaction;
2,2-dimethylpropionamide
754-10-9

2,2-dimethylpropionamide

tetra(n-butyl)ammonium hydrogensulfate
32503-27-8

tetra(n-butyl)ammonium hydrogensulfate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With sodium hydroxide; hypochloric acid In dichloromethane; water83%
N-(tert-butyl)-5-(chloromethyl)-1,3-oxathiolan-2-imine

N-(tert-butyl)-5-(chloromethyl)-1,3-oxathiolan-2-imine

A

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In quinoline at 230℃;A 12%
B 81%
Tosyl isocyanate
4083-64-1

Tosyl isocyanate

tert-butylamine
75-64-9

tert-butylamine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
Stage #1: Tosyl isocyanate; tert-butylamine In 5,5-dimethyl-1,3-cyclohexadiene at 0℃; for 4h; Reflux;
Stage #2: In 5,5-dimethyl-1,3-cyclohexadiene at 83 - 90℃; Solvent;
80%
tert-butyl-(di-tert-butyl-diaziridin-3-ylidene)-amine
22975-87-7

tert-butyl-(di-tert-butyl-diaziridin-3-ylidene)-amine

A

1,2,4-tri(tert-butyl)semicarbazide
683223-12-3

1,2,4-tri(tert-butyl)semicarbazide

B

1,2-di-tert-butylhydrazine
13952-69-7

1,2-di-tert-butylhydrazine

C

tert-butylamine
75-64-9

tert-butylamine

D

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With water In 1,4-dioxane for 2h; Reflux;A 69%
B n/a
C n/a
D n/a
t-butyl bromide
507-19-7

t-butyl bromide

silver (I) nitro cyanamide
20236-50-4

silver (I) nitro cyanamide

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In diethyl ether at 25℃; for 4h;63%
With magnesium sulfate In diethyl ether at 25℃; for 4h;63%
(Ni(O2)(CNC4H9-t)2)x
32824-82-1

(Ni(O2)(CNC4H9-t)2)x

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

(t-C4H9NC)2Ni(NC)2CC(CN)2
24917-37-1

(t-C4H9NC)2Ni(NC)2CC(CN)2

B

(t-C4H9NC)3Ni(NC)2CC(CN)2
36008-95-4

(t-C4H9NC)3Ni(NC)2CC(CN)2

C

oxygen
80937-33-3

oxygen

D

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In toluene react. in toluene at -20 °C;;A 38.8%
B n/a
C 56.3%
D 59.2%
In toluene react. in toluene at -20 °C;;A 38.8%
B n/a
C 56.3%
D 59.2%
N,N',N
64011-17-2

N,N',N"-tris(tert-butyl)sulfur triimide

isocyanatophosphoryl difluoride
1495-54-1

isocyanatophosphoryl difluoride

A

Di-tert-butyl-difluorophosphoryl-Schwefeltriimid

Di-tert-butyl-difluorophosphoryl-Schwefeltriimid

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In methylbutane at -70 - 10℃; for 16h;A 55%
B n/a
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butylamine
75-64-9

tert-butylamine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With dmap In dichloromethane at 25℃; for 0.166667h;49%
2-(tert-butylamino)-2-oxoacetic acid
169772-25-2

2-(tert-butylamino)-2-oxoacetic acid

A

N,N'-di-tert-butyloxamide
37486-48-9

N,N'-di-tert-butyloxamide

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate In dichloromethane; water at 40℃; for 3h;A 14%
B 46%
tertiary butyl chloride
507-20-0

tertiary butyl chloride

carbon monoxide
201230-82-2

carbon monoxide

{Cp*Mo[N(iPr)C(Me)N(iPr)]}2(μ-η1:η1-N2)
1241890-53-8

{Cp*Mo[N(iPr)C(Me)N(iPr)]}2(μ-η1:η1-N2)

A

(η5-C5Me5)*Mo{N(iPr)C(Me)N(iPr)}(CO)2
1241890-64-1

(η5-C5Me5)*Mo{N(iPr)C(Me)N(iPr)}(CO)2

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
Stage #1: {Cp*Mo[N(iPr)C(Me)N(iPr)]}2(μ-η1:η1-N2) With 1,2,4,5-tetramethylbenzene In benzene-d6 for 70h; Sealed tube; UV-irradiation;
Stage #2: tertiary butyl chloride In benzene-d6 at 80℃; for 27h;
Stage #3: carbon monoxide In benzene-d6 at 25℃; under 258.581 Torr; for 23h;
A 34%
B 27%
methyl N-tert-butylcarbamate
27701-01-5

methyl N-tert-butylcarbamate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With potassium ethoxide
ethyl N-tert-butylcarbamate
1611-50-3

ethyl N-tert-butylcarbamate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With calcium hydroxide
With formaldehyd; aniline; 2,4-Toluene diisocyanate at 170 - 180℃;
trimethylacetyl azide
4981-48-0

trimethylacetyl azide

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
durch Kochen;
Heating;
bei 10 min langem Erwaermen;
2,2-dimethylpropionamide
754-10-9

2,2-dimethylpropionamide

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With lead(IV) acetate In N,N-dimethyl-formamide
With [N-(p-tolylsulfonyl)imino]phenyliodinane In dichloromethane at 20℃; for 1h; Hofmann rearrangement; Inert atmosphere;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With sodium azide; diphenylsilyl dichloride In quinoline
N-tert.Butyl-carbamidsaeure-(2-hydroxyphenyl)-ester
35580-94-0

N-tert.Butyl-carbamidsaeure-(2-hydroxyphenyl)-ester

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
at 220 - 260℃;
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

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
at 190℃; under 12 Torr;
pivaloyl chloride
3282-30-2

pivaloyl chloride

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With tetrabutylammoniun azide In toluene
isocyanic acid
75-13-8

isocyanic acid

isobutene
115-11-7

isobutene

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
With toluene-4-sulfonic acid
3-tert-Butyl-1,1,2-trimethyl-isothiourea
66661-88-9

3-tert-Butyl-1,1,2-trimethyl-isothiourea

benzoyl isocyanate
4461-33-0

benzoyl isocyanate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N,N'-di-tert-butyldiazetidinedione
30885-14-4

N,N'-di-tert-butyldiazetidinedione

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
at 200℃;
N1-Benzyl-N1-hydroxy-benzamidin
106697-10-3

N1-Benzyl-N1-hydroxy-benzamidin

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N1-Benzyl-N1-(tert-butyl)carbamoyloxy-benzamidin

N1-Benzyl-N1-(tert-butyl)carbamoyloxy-benzamidin

Conditions
ConditionsYield
In chloroform100%
(2S)-2-[(diphenylphosphino)methyl]pyrrolidine
60261-46-3

(2S)-2-[(diphenylphosphino)methyl]pyrrolidine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

(S)-1-t-butylaminocarbonyl-2-diphenylphosphinomethylpyrrolidine
163809-04-9

(S)-1-t-butylaminocarbonyl-2-diphenylphosphinomethylpyrrolidine

Conditions
ConditionsYield
In dichloromethane for 24h; Ambient temperature;100%
1,3-di-(N-benzylamino)-2-hydroxypropane
65838-17-7

1,3-di-(N-benzylamino)-2-hydroxypropane

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

1-Benzyl-1-[3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propyl]-3-tert-butyl-urea

1-Benzyl-1-[3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propyl]-3-tert-butyl-urea

Conditions
ConditionsYield
In dichloromethane100%
benzyl ((3-hydroxy)adamantan-1-yl)carbamate
565453-43-2

benzyl ((3-hydroxy)adamantan-1-yl)carbamate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

(3-tert-butylcarbamoyloxy-adamantan-1-yl)-carbamic acid benzyl ester
565453-44-3

(3-tert-butylcarbamoyloxy-adamantan-1-yl)-carbamic acid benzyl ester

Conditions
ConditionsYield
With chloro-trimethyl-silane In dichloromethane at 20℃; for 18h;100%
(2S,4S)-Nα-Cbz-4-aminoproline benzyl ester
329191-57-3

(2S,4S)-Nα-Cbz-4-aminoproline benzyl ester

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

(2S,4S)-1,2-dibenzyloxycarbonyl-4-(3-tert-butylureido)pyrrolidine

(2S,4S)-1,2-dibenzyloxycarbonyl-4-(3-tert-butylureido)pyrrolidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
N-(t-butoxycarbonyl)-4-chloroaniline
18437-66-6

N-(t-butoxycarbonyl)-4-chloroaniline

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

3-(tert-butyl)-6-chloroquinazoline-2,4(1H,3H)-dione
207735-50-0

3-(tert-butyl)-6-chloroquinazoline-2,4(1H,3H)-dione

Conditions
ConditionsYield
Stage #1: N-(t-butoxycarbonyl)-4-chloroaniline With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -20℃; for 2.16667h;
Stage #2: Tert-butyl isocyanate In tetrahydrofuran; pentane at -20 - 20℃; for 15h; Heating / reflux;
100%
Stage #1: N-(t-butoxycarbonyl)-4-chloroaniline With tert.-butyl lithium In tetrahydrofuran at -78 - -20℃; for 2h;
Stage #2: Tert-butyl isocyanate In tetrahydrofuran at -20 - 70℃; for 12h;
98%
N-{3-[4-amino-1-hydroxy-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide
909105-54-0

N-{3-[4-amino-1-hydroxy-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-{3-[4-{[(tert-butylamino)carbonyl]amino}-1-hydroxy-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide

N-{3-[4-{[(tert-butylamino)carbonyl]amino}-1-hydroxy-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;100%
Sn(N(SiMe3)2)(μ-OBu(t))2Sn(OSiMe3)

Sn(N(SiMe3)2)(μ-OBu(t))2Sn(OSiMe3)

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

[Sn(OSiMe3)(μ-OBu(t))]2

[Sn(OSiMe3)(μ-OBu(t))]2

Conditions
ConditionsYield
In benzene byproducts: t-BuNCNSiMe3; N2-atmosphere; 1 equiv. isocyanate, 25°C;100%
In (2)H8-toluene byproducts: t-BuNCNSiMe3; N2-atmosphere; -10°C; not isolated, reaction followed by (1)H-NMR spectroscopy;
[Sn(N(SiMe3)2)(μ-OBu(t))]2

[Sn(N(SiMe3)2)(μ-OBu(t))]2

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Sn(N(SiMe3)2)(μ-OBu(t))2Sn(OSiMe3)

Sn(N(SiMe3)2)(μ-OBu(t))2Sn(OSiMe3)

Conditions
ConditionsYield
In benzene byproducts: t-BuNCNSiMe3; N2-atmosphere; 1 equiv. isocyanate, 25°C;100%
In (2)H8-toluene byproducts: t-BuNCNSiMe3; N2-atmosphere; mixing at -20°C, then warming; not isolated, reaction followed by (1)H-NMR spectroscopy;
tert-butyl 4-(aminomethyl)piperidine-1-carboxylate
144222-22-0

tert-butyl 4-(aminomethyl)piperidine-1-carboxylate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-tert-butyl-N'-[(1-tert-butoxycarbonylpiperidin-4-yl)methyl]urea
614745-54-9

N-tert-butyl-N'-[(1-tert-butoxycarbonylpiperidin-4-yl)methyl]urea

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;100%
1'-tert-butyl 3-methyl 3-hydroxy-1,4'-bipiperidine-1',3-dicarboxylate
923010-85-9, 923011-00-1, 923011-01-2

1'-tert-butyl 3-methyl 3-hydroxy-1,4'-bipiperidine-1',3-dicarboxylate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

tert-butyl 4-(3-tert-butyl-2,4-dioxo-1-oxa-3,7-diazaspiro[4.5]dec-7-yl)piperidine-1-carboxylate
923011-11-4

tert-butyl 4-(3-tert-butyl-2,4-dioxo-1-oxa-3,7-diazaspiro[4.5]dec-7-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h;100%
1-benzylcarbamoyladamantane-3-ol

1-benzylcarbamoyladamantane-3-ol

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

3-[[(tertbutylamino)carbonyl]oxy]-1-benzylcarbamoyladamantane

3-[[(tertbutylamino)carbonyl]oxy]-1-benzylcarbamoyladamantane

Conditions
ConditionsYield
With chloro-trimethyl-silane In dichloromethane at 20℃; for 18h;100%
(-)-menthol
2216-51-5

(-)-menthol

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

O-(1R,2S,5R)-5-methyl-2-isopropylcyclohexyl N-tert-butylcarbamate
915764-72-6

O-(1R,2S,5R)-5-methyl-2-isopropylcyclohexyl N-tert-butylcarbamate

Conditions
ConditionsYield
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 2h;100%
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Sealed tube;100%
(R)-2-((2-cyano-3-nitrophenoxy)methyl)pyrrolidinium chloride
1093204-94-4

(R)-2-((2-cyano-3-nitrophenoxy)methyl)pyrrolidinium chloride

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

(R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-tert-butylpyrrolidine-1-carboxamide
1093205-07-2

(R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-tert-butylpyrrolidine-1-carboxamide

Conditions
ConditionsYield
100%
2-chloro-5-fluorobenzenesulfonamide

2-chloro-5-fluorobenzenesulfonamide

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-(tert-butylcarbamoyl)-2-chloro-5-fluorobenzenesulfonamide

N-(tert-butylcarbamoyl)-2-chloro-5-fluorobenzenesulfonamide

Conditions
ConditionsYield
Stage #1: 2-chloro-5-fluorobenzenesulfonamide With potassium hydroxide In water; acetone at 20℃; for 0.25h;
Stage #2: Tert-butyl isocyanate In N,N-dimethyl-formamide at 20℃;
100%
Stage #1: 2-chloro-5-fluorobenzenesulfonamide With potassium hydroxide In water; acetone at 20℃; for 0.25h;
Stage #2: Tert-butyl isocyanate In N,N-dimethyl-formamide at 20℃;
100%
C24H32N4Zr

C24H32N4Zr

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

{(C6H4CH2)2Cyclam-1-tert-butylcarboxamidato}Zr

{(C6H4CH2)2Cyclam-1-tert-butylcarboxamidato}Zr

Conditions
ConditionsYield
In benzene-d6 at 60℃; for 48h; Inert atmosphere; Schlenk technique;100%
1,3,5-trimethoxy-p-tert-butylcalix[6]arene
138709-55-4

1,3,5-trimethoxy-p-tert-butylcalix[6]arene

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

C75H100N2O9

C75H100N2O9

Conditions
ConditionsYield
Stage #1: 1,3,5-trimethoxy-p-tert-butylcalix[6]arene With barium hydroxide octahydrate In dichloromethane at 20℃; for 0.5h;
Stage #2: Tert-butyl isocyanate In dichloromethane at 20℃; for 50h;
100%
para-tert-butylphenol
98-54-4

para-tert-butylphenol

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-tert-butyl-O-( p-tert-butylphenyl)carbamate

N-tert-butyl-O-( p-tert-butylphenyl)carbamate

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 0.5h;100%
C43H60BN

C43H60BN

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

C48H69BN2O

C48H69BN2O

Conditions
ConditionsYield
In benzene at 20℃; for 0.0166667h; Inert atmosphere; Glovebox; Schlenk technique;100%
methyl 5-(4-hydroxypiperidin-1-yl)-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate

methyl 5-(4-hydroxypiperidin-1-yl)-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

methyl 5-(4-((tert-butylcarbamoyl)oxy)piperidin-1-yl)-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate

methyl 5-(4-((tert-butylcarbamoyl)oxy)piperidin-1-yl)-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 130 - 140℃; for 126h; Microwave irradiation;100%
descarboethoxyloratadine
100643-71-8

descarboethoxyloratadine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-(t-butyl)-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxamide

N-(t-butyl)-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h;100%
4-((4-(pyridin-4-yl)pyrimidin-2-yl)amino)benzohydrazide

4-((4-(pyridin-4-yl)pyrimidin-2-yl)amino)benzohydrazide

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-(tert-butyl)-2-(4-((4-(pyridin-4-yl)pyrimidin-2-yl)amino)benzoyl)hydrazine-1-carboxamide

N-(tert-butyl)-2-(4-((4-(pyridin-4-yl)pyrimidin-2-yl)amino)benzoyl)hydrazine-1-carboxamide

Conditions
ConditionsYield
In ethanol at 70℃; for 4h;99.24%
Trimethylenediamine
109-76-2

Trimethylenediamine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

1-tert-Butyl-3-[3-(3-tert-butyl-ureido)-propyl]-urea
64544-74-7

1-tert-Butyl-3-[3-(3-tert-butyl-ureido)-propyl]-urea

Conditions
ConditionsYield
at 20℃; for 2h; Inert atmosphere;99.2%
2,2-dimethoxyethylamine
22483-09-6

2,2-dimethoxyethylamine

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

N-tert-Butyl-N'-(2,2-dimethoxyethyl)harnstoff
92075-15-5

N-tert-Butyl-N'-(2,2-dimethoxyethyl)harnstoff

Conditions
ConditionsYield
In dichloromethane99%
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%
Cinchonin
118-10-5

Cinchonin

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

(9S)-9-deoxy-cinchonin-9-yl tert-butylcarbamate

(9S)-9-deoxy-cinchonin-9-yl tert-butylcarbamate

Conditions
ConditionsYield
With dibutyltin(II) dilaurate In toluene at 110℃; for 48h;99%
(Z)-4-heptenal
6728-31-0

(Z)-4-heptenal

benzoic acid
65-85-0

benzoic acid

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

(Z)-1-(tert-butylcarbamoyl)hept-4-enyl benzoate

(Z)-1-(tert-butylcarbamoyl)hept-4-enyl benzoate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;99%
(S)-valinol
2026-48-4

(S)-valinol

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

1-tert-butyl-3-((S)-1-hydroxymethyl-2-methyl-propyl)-urea

1-tert-butyl-3-((S)-1-hydroxymethyl-2-methyl-propyl)-urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 18h;99%
Os(η-1,4-(CHMe2)MeC6H4)NBu(t)

Os(η-1,4-(CHMe2)MeC6H4)NBu(t)

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

{(η6-p-cymene)Os((N-t-Bu)2CO)}
134654-67-4

{(η6-p-cymene)Os((N-t-Bu)2CO)}

Conditions
ConditionsYield
In benzene under N2; to a soln. of the Os-complex in benzene was condensed t-BuNCO at -196°C, heated at 45°C with stirring for 36 h; solvent was removed in vac.; elem. anal.;99%
In benzene heating at 45°C for 36h;>98

1609-86-5Relevant articles and documents

Isocyanates from Alkyl and Aralkyl Halides

Boyer, Joseph H.,Manimaran, Thanikavelu

, p. 907 (1987)

Alkyl and aralkyl halides were converted to isocyanates (63percent-89percent) by treatment with the silver salt of nitrocyanamide.This new reaction offers the first direct conversion of an organic halide to an isocyanate that is general, efficient, and facile.

Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C-H Imidoylation of Heterocycle-Containing Molecules

Tereniak, Stephen J.,Stahl, Shannon S.

, p. 14533 - 14541 (2017)

A recently reported Pd-catalyzed method for oxidative imidoylation of C-H bonds exhibits unique features that have important implications for Pd-catalyzed aerobic oxidation catalysis: (1) The reaction tolerates heterocycles that commonly poison Pd catalysts. (2) The site selectivity of C-H activation is controlled by an N-methoxyamide group rather than a suitably positioned heterocycle. (3) A Pd0 source, Pd2(dba)3 (dba = dibenzylideneacetone), is superior to Pd(OAc)2 as a precatalyst, and other PdII sources are ineffective. (4) The reaction performs better with air, rather than pure O2. The present study elucidates the origin of these features. Kinetic, mechanistic, and in situ spectroscopic studies establish that PdII-mediated C-H activation is the turnover-limiting step. The tBuNC substrate is shown to coordinate more strongly to PdII than pyridine, thereby contributing to the lack of heterocycle catalyst poisoning. A well-defined PdII-peroxo complex is a competent intermediate that promotes substrate coordination via proton-coupled ligand exchange. The effectiveness of this substrate coordination step correlates with the basicity of the anionic ligands coordinated to PdII, and Pd0 catalyst precursors are most effective because they selectively afford the PdII-peroxo in situ. Finally, elevated O2 pressures are shown to contribute to background oxidation of the isonitrile, thereby explaining the improved performance of reactions conducted with air rather than 1 atm O2. These collective results explain the unique features of the aerobic C-H imidoylation of N-methoxybenzamides and have important implications for other Pd-catalyzed aerobic C-H oxidation reactions.

Monomeric (Pentamethylcyclopentadienyl)iridium Imido Compounds: Synthesis, Structure, and Reactivity

Glueck, David S.,Wu, Jianxin,Hollander, Frederick J.,Bergman, Robert G.

, p. 2041 - 2054 (1991)

The monomeric terminal imido complexes Cp*IrNR (Cp* = η5-C5Me5; 1a, R = t-Bu; 1b, R = SiMe2t-Bu; 1c, R = 2,6-Me2C6H3; 1d, R = 2,6-i-Pr2C6H3) were prepared from [Cp*IrCl2]2 (2) and 4 equiv of the corresponding lithium amide LiNHR in THF. In addition, the complexes Cp*Ir(RNH2)Cl2 (3a, R = t-Bu; 3d, R = 2,6-i-Pr2C6H3) were made from an amine and [Cp*IrCl2]2 (2) and dehydrochlorinated with KN(SiMe3)2 to provide an alternate route to 1a,d. Efficient exchange occurred between 1a and arylamines, leading to 1c,d and tert-butylamine. tert-Butylimido complex 1a, a weak nucleophile, reacted with MeI to form [Cp*IrI2]2 and Me3Nt-Bu+I-. Coupling of the imido ligand in 1a with CNt-Bu and CO gave Cp*Ir(t-BuNCNt-Bu)(CNt-Bu) (4) and Cp*Ir(t-BuNCO)(CO) (5a), respectively. Cp*IrPPh3(t-BuNCO) (5b) was formed from 1a, PPh3, and CO. The bridging imido complex Cp*IrNt-Bu(dppePt) (6, dppe = 1,2-bis(diphenylphosphino)ethane) was prepared from 1a and dppePt(C2H4). Complex 1a and CO2 gave the cycloadduct Cp*Ir(Nt-BuOCO) (7a), which added PPh3 to form Cp*IrPPh3(Nt-BuOCO) (7b). Two equivalents of dimethylacetylenedicarboxylate reacted with 1a to yield the pyrrole complex Cp(Ir(η4-RCCRNt-BuRCCR) (8, R = CO2Me). Maleic anhydride was added to 1a to give Cp*Ir[Nt-BuC(O)CH=CHCO2] (9a), which reacted with CO to yield Cp*Ir(CO)[Nt-BuC(O)CH=CHCO2] (9b). Compounds 1a-d, 7a, and 8 were structurally characterized by X-ray diffraction; imido complexes 1a-d have short Ir-N distances and nearly linear Ir-N-C(Si) angles, consistent with the presence of a metal-nitrogen triple bond.

Otsuka et al.

, p. 836 (1967)

Phosphazenes: Efficient organocatalysts for the catalytic hydrosilylation of carbon dioxide

Courtemanche, Marc-André,Légaré, Marc-André,Rochette, étienne,Fontaine, Frédéric-Georges

, p. 6858 - 6861 (2015)

Phosphazene superbases are efficient organocatalysts for the metal-free catalytic hydrosilylation of carbon dioxide. They react with CO2 to form the respective phosphine oxides, but in the presence of hydrosilanes, CO2 can be selectively reduced to silyl formates, which can in turn be reduced to methoxysilanes by addition of an extra loading of silanes. Activities reach a TOF of 32 h-1 with a TON of 759. It is also shown that unexpectedly, N,N-dimethylformamide can reduce CO2 to a mixture of silyl formates, acetals and methoxides in the absence of any catalyst.

Reversible CO2 fixation by N-heterocyclic imines forming water-stable zwitterionic nitrogen-base-CO2 adducts

Wilm, Lukas F. B.,Eder, Tobias,Mück-Lichtenfeld, Christian,Mehlmann, Paul,Wünsche, Marius,Bu?, Florenz,Dielmann, Fabian

supporting information, p. 640 - 648 (2019/02/14)

Zwitterionic Lewis base adducts between nitrogen bases and CO2 play a pivotal role as transient intermediates in many projects aiming at CO2 capture, storage and utilization. Yet, fundamental questions about the required parameters for the formation of isolable adducts remain and only a single adduct (TBD-CO2) has been characterized unequivocally. Using a combination of NMR spectroscopy, single-crystal X-ray diffraction, IR spectroscopy and quantum chemistry, we systematically explore the formation and properties of the CO2 adducts with amidines (DBN), guanidines (MTBD) and N-heterocyclic imines. Spectroscopic and theoretical results show that the stability of the NHI-CO2 adducts is largely governed by the nature of the N-heterocycle and the substituent at the exocyclic nitrogen atom. The surprising stability of some NHI-CO2 adducts towards hydrolysis can be ascribed to the hydrophobic CO2 binding site of the nitrogen bases and offers new opportunities in the field of CO2 capture and utilization.

Reaction of N-alkyl-N′-(trimethylsilyl)carbodiimides with nitrating agents. The synthesis of N-(tert-butyl)-N′-nitrocarbodiimide

Churakov,Ioffe,Voronin,Tartakovsky

, p. 56 - 60 (2018/04/27)

Reaction of N-Alk-N′-(trimethylsilyl)carbodiimides (Alk = Me, But) with nitrating agents (N2O5, (NO2)2SiF6) affords alkyl(nitro)cyanamides and N-alkyl-N′-nitrocarbodiimides. The product ratio depends on the reaction conditions. N-(tert-butyl)-N′-nitrocarbodiimide can be obtained in almost pure form. This compound is stable at temperatures below 10 °C. Its structure was confirmed by 1Н, 13C, and 14N NMR. The reaction of N-(tert-butyl)-N′-nitrocarbodiimide with amines provides a new route to N-alkyl(aryl)-substituted N′-(tert-butyl)-N″-nitroguanidines.

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