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32175-00-1

Basic Information
CAS No.: 32175-00-1
Name: 1-Isocyanato-4-methylcyclohexane
Molecular Structure:
Molecular Structure of 32175-00-1 (1-Isocyanato-4-methylcyclohexane)
Formula: C8H13NO
Molecular Weight: 139.19
Synonyms: Isocyanicacid, 4-methylcyclohexyl ester, trans- (8CI);trans-1-Isocyanato-4-methylcyclohexane;
EINECS: 608-715-5
Density: 1.04 g/cm3
Melting Point:
Boiling Point: 182.2 °C at 760 mmHg
Flash Point: 60.1 °C
Solubility:
Appearance: clear colourless liquid
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 29.43000
LogP: 1.90090
Synthetic route
75-44-5

phosgene

2523-55-9

trans-4-methylcyclohexanamine

32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

C8H14FNO

32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; under 760.051 Torr; for 3h; Concentration;
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

119018-29-0

N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide

93479-97-1

glimepiride

Conditions
ConditionsYield
In tert-butyl methyl ether; cyclohexanone at 30℃; for 10h; Temperature;94.5%
Stage #1: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide With potassium carbonate In acetone; butanone for 0.5h; Inert atmosphere; Reflux;
Stage #2: (1R,4R)-1-isocyanato-4-methylcyclohexane In acetone; butanone Inert atmosphere; Reflux;
90%
Stage #1: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide With potassium carbonate at 55 - 60℃; for 1h; Heating / reflux;
Stage #2: (1R,4R)-1-isocyanato-4-methylcyclohexane In toluene for 12h; Heating / reflux;
86.3%
593-71-5

Chloroiodomethane

32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

31715-94-3

trans-2-chloro-N-(4-methylcyclohexyl)acetamide

Conditions
ConditionsYield
With methyllithium; lithium bromide In diethyl ether at -78℃; for 1h; chemoselective reaction;91%
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

26003-39-4

N-(4-methylcyclohexyl)formamide

Conditions
ConditionsYield
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; chemoselective reaction;87%
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

methyl 2-(methylamino)-5-oxo-5H-thieno[3,2-b]pyran-6-carboxylate

methyl 2-(1-methyl-3-((1r,4r)-4-methylcyclohexyl)ureido)-5-oxo-5H-thieno[3,2-b]pyran-6-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 90 - 100℃; for 16h;32.37%
51-21-8

5-fluorouracil

32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-carboxylic acid (4-methyl-cyclohexyl)-amide

Conditions
ConditionsYield
With pyridine 1.) 90 deg C, 2 h, 2.) RT, overnight;31%
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-66-0

N-[2-(4-Sulfamoyl-phenyl)-butyl]-benzamide

C25H33N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

54198-69-5

3-Methyl-N-[2-(4-sulfamoyl-phenyl)-butyl]-benzamide

C26H35N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25200-70-8

4-Chloro-N-methyl-N-(4-sulfamoyl-benzyl)-benzamide

C23H28ClN3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25200-65-1

3,N-Dimethyl-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzamide

C25H33N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-68-2

4-Chloro-N-[2-(4-sulfamoyl-phenyl)-butyl]-benzamide

25257-24-3

C25H32ClN3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-70-6

N-[2-Methyl-2-(4-sulfamoyl-phenyl)-propyl]-benzamide

25257-26-5

C25H33N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

54198-67-3

3-Chloro-N-methyl-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzamide

C24H30ClN3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25196-93-4

N-[2-(2,4,6-Trimethyl-3-sulfamoyl-phenyl)-ethyl]-benzamide

C26H35N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-42-2

2-(3,4-Dichloro-phenyl)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acetamide

C24H29Cl2N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-60-4

3-Methyl-3-phenyl-N-[2-(4-sulfamoyl-phenyl)-ethyl]-butyramide

C27H37N3O4S

Conditions
ConditionsYield
(i) K2CO3, acetone, (ii) /BRN= 2080824/; Multistep reaction;
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-46-6

(E)-3-(3,4-Dichloro-phenyl)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acrylamide

C25H29Cl2N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-53-5

2-Benzyl-N-[2-(4-sulfamoyl-phenyl)-ethyl]-butyramide

C27H37N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-63-7

3-Methyl-2-phenyl-N-[2-(4-sulfamoyl-phenyl)-ethyl]-butyramide

C27H37N3O4S

Conditions
ConditionsYield
(i) K2CO3, acetone, (ii) /BRN= 2080824/; Multistep reaction;
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-34-2

2-(3,5-Dimethyl-phenoxy)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acetamide

C26H35N3O5S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-36-4

2-(3,4-Dimethyl-phenoxy)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acetamide

C26H35N3O5S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-55-7

2-Ethyl-2-phenyl-N-(4-sulfamoyl-benzyl)-butyramide

C27H37N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

53446-60-9

3-Phenethyloxy-N-[2-(4-sulfamoyl-phenyl)-ethyl]-propionamide

C27H37N3O5S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-44-4

2-(3,4-Dimethoxy-phenyl)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acetamide

C26H35N3O6S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-38-6

2-(2,4-Dichloro-phenoxy)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acetamide

C24H29Cl2N3O5S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25311-80-2

2-(4-Chloro-phenyl)-2-ethyl-N-[2-(4-sulfamoyl-phenyl)-ethyl]-butyramide

C28H38ClN3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25199-40-0

2-(2,4-Dichloro-6-methyl-phenoxy)-N-[2-(4-sulfamoyl-phenyl)-ethyl]-acetamide

C25H31Cl2N3O5S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

N-(2-Chloro-5-sulfamoyl-benzyl)-benzamide

C22H26ClN3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

2-methyl-N-(4-sulfamoylphenethyl)benzamide

C24H31N3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
32175-00-1

(1R,4R)-1-isocyanato-4-methylcyclohexane

25196-89-8

N-[2-(2-Chloro-5-sulfamoyl-phenyl)-ethyl]-benzamide

C23H28ClN3O4S

Conditions
ConditionsYield
With sodium hydroxide In acetone
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    1-Isocyanato-4-methylcyclohexane 32175-00-1

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Specification

The trans-4-methycyclohexyl isocyanate, with the CAS registry number 32175-00-1, is also named trans-4-methyl cyclohexyl isocyanate. It is a kind of clear colourless liquid, and belongs to the product category of Pharmaceutical intermediates. And the molecular formula of this chemical is C8H13NO. What's more, it is usually used as intermediate for the preparation of Glimepiride.

The physical properties of trans-4-methycyclohexyl isocyanate are as followings: (1)ACD/LogP: 3.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.38; (4)ACD/LogD (pH 7.4): 3.38; (5)#H bond acceptors: 2; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 1; (8)Polar Surface Area: 29.43 Å2; (9)Index of Refraction: 1.518; (10)Molar Refractivity: 40.58 cm3; (11)Molar Volume: 133.7 cm3; (12)Polarizability: 16.08×10-24cm3; (13)Surface Tension: 35.4 dyne/cm; (14)Density: 1.04 g/cm3; (15)Flash Point: 60.1 °C; (16)Enthalpy of Vaporization: 41.85 kJ/mol; (17)Boiling Point: 182.2 °C at 760 mmHg; (18)Vapour Pressure: 0.818 mmHg at 25°C.

Uses of trans-4-methycyclohexyl isocyanate: It can react with 5-fluoro-1H-pyrimidine-2,4-dione to produce 5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-carboxylic acid (4-methyl-cyclohexyl)-amide. This reaction will need reagent pyridine, and the yield is about 31%.

You can still convert the following datas into molecular structure:
(1)SMILES: CC1CCC(CC1)N=C=O
(2)InChI: InChI=1/C8H13NO/c1-7-2-4-8(5-3-7)9-6-10/h7-8H,2-5H2,1H3/t7-,8-
(3)InChIKey: SWSXEZOUBBVKCO-ZKCHVHJHBX