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13908-11-7

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13908-11-7 Usage

Description

1-CYCLOHEXYL-3-(2-CHLOROETHYL)UREA, also known as Lomustine Related Compound B, is an organic compound that serves as a crucial reagent in the synthesis of various pharmaceutical agents. It is characterized by its unique chemical structure, which includes a cyclohexyl group and a chloroethyl urea moiety. 1-CYCLOHEXYL-3-(2-CHLOROETHYL)UREA plays a significant role in the development of chemotherapy drugs and potential antitumor agents.

Uses

1. Used in Pharmaceutical Synthesis:
1-CYCLOHEXYL-3-(2-CHLOROETHYL)UREA is used as a reagent for the synthesis of lomustine, a chemotherapy drug. Its role in the synthesis process is essential for the production of effective cancer treatments.
2. Used in Antitumor Agent Development:
1-CYCLOHEXYL-3-(2-CHLOROETHYL)UREA is used as a precursor in the synthesis of N-nitrosoureas and N-nitrosothiourea, which are potential antitumor agents. These compounds have shown promise in the development of new cancer therapies.
3. Used in the Chemical Industry:
In the chemical industry, 1-CYCLOHEXYL-3-(2-CHLOROETHYL)UREA is used as an intermediate for the production of various chemicals and pharmaceuticals. Its unique structure allows for further modification and synthesis of a wide range of compounds with diverse applications.
4. Used in Research and Development:
1-CYCLOHEXYL-3-(2-CHLOROETHYL)UREA is utilized in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various fields, including medicine, agriculture, and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 13908-11-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,9,0 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13908-11:
(7*1)+(6*3)+(5*9)+(4*0)+(3*8)+(2*1)+(1*1)=97
97 % 10 = 7
So 13908-11-7 is a valid CAS Registry Number.

13908-11-7 Well-known Company Product Price

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  • (1369431)  Lomustine Related Compound B  United States Pharmacopeia (USP) Reference Standard

  • 13908-11-7

  • 1369431-25MG

  • 13,501.80CNY

  • Detail

13908-11-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(2-chloroethyl)-3-cyclohexylurea

1.2 Other means of identification

Product number -
Other names 1-(2-Chlorethyl)-3-cyclohexylharnstoff

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:13908-11-7 SDS

13908-11-7Synthetic route

2-chloroethyl isothiocyanate
1943-83-5

2-chloroethyl isothiocyanate

cyclohexylamine
108-91-8

cyclohexylamine

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 50℃; for 0.0166667h; Solvent; Temperature; Time; Flow reactor;91.7%
With triethylamine In tetrahydrofuran at 50℃; for 0.0166667h; Solvent; Temperature;91.7%
With diethyl ether
N-cyclohexyl-carbamate de succinimidyle
80672-61-3

N-cyclohexyl-carbamate de succinimidyle

chloroethylamine
689-98-5

chloroethylamine

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

Conditions
ConditionsYield
Ambient temperature;68.6%
Hexamethylendi-
34693-48-6

Hexamethylendi-

cyclohexylamine
108-91-8

cyclohexylamine

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

Ethyl-5-(2-chloroethyl)-3-nitrosohydantoat
60285-28-1

Ethyl-5-(2-chloroethyl)-3-nitrosohydantoat

cyclohexylamine
108-91-8

cyclohexylamine

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

Conditions
ConditionsYield
In water Ambient temperature;
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
13010-47-4

1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea

A

Diazoethan
1117-96-0

Diazoethan

B

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

C

ethanol
64-17-5

ethanol

D

cyclohexylamine
108-91-8

cyclohexylamine

E

ethylamine
75-04-7

ethylamine

F

2-chlorodiazomethane

2-chlorodiazomethane

Conditions
ConditionsYield
With potassium hydroxide; aluminum nickel In methanol Product distribution; Mechanism; degradation under various conditions (HBr in glac. CH3CO2H) with preparation of nonmutagenic reaction mixtures of products;
Cyclohexyl isocyanate
3173-53-3

Cyclohexyl isocyanate

chloroethylamine
689-98-5

chloroethylamine

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

Conditions
ConditionsYield
In diethyl ether Ambient temperature;
cyclohexylamine
108-91-8

cyclohexylamine

N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 56.6 percent / acetonitrile / Ambient temperature
2: 68.6 percent / Ambient temperature
View Scheme
N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
13010-47-4

1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea

Conditions
ConditionsYield
With tin(IV) chloride; sodium nitrite In dichloromethane at 20℃; for 2h;100%
With tert.-butylnitrite In ethanol; acetonitrile at 25℃; for 0.133333h; Reagent/catalyst; Solvent; Temperature; Time; Flow reactor;91.2%
With tert.-butylnitrite In ethanol; acetonitrile at 25℃; for 0.133333h; Reagent/catalyst; Temperature; Solvent;91.2%
N-(2-chloroethyl)-N'-cyclohexylurea
13908-11-7

N-(2-chloroethyl)-N'-cyclohexylurea

2-(cyclohexylamino)-2-oxazoline
10002-37-6

2-(cyclohexylamino)-2-oxazoline

Conditions
ConditionsYield
In water Heating;80%

13908-11-7Relevant articles and documents

Pettit et al.

, p. 1029,1030 (1975)

Rapid On-Demand Synthesis of Lomustine under Continuous Flow Conditions

Jaman, Zinia,Sobreira, Tiago J. P.,Mufti, Ahmed,Ferreira, Christina R.,Cooks, R. Graham,Thompson, David H.

, p. 334 - 341 (2019/02/27)

Lomustine, an important agent for treatment of brain tumors and Hodgkin's lymphoma, has been synthesized using continuous flow methodology. Desorption electrospray ionization mass spectrometry (DESI-MS) was used to quickly explore a large number of reaction conditions for one of the reaction steps and guide the efficient translation of optimized conditions to continuous lomustine production. Using only four inexpensive commercially available starting materials and a total residence time of 9 min, lomustine was prepared via a linear sequence of two chemical reactions performed separately in two telescoped flow reactors. Sequential offline extraction and filtration resulted in a 63% overall yield of pure lomustine at a production rate of 110 mg/h. The primary advantages of this approach are the rapid manufacture of lomustine with two telescoped steps to avoid isolation and purification of a labile intermediate and the mild conditions used in the nitrosylation step, thereby significantly increasing the purity and yield of this active pharmaceutical ingredient.

Heterocyclic compounds. Part IX. Syntheses of N-nitrosoureas and N-nitrosothioureas as possible antitumor agents

Sahu,Dehuri,Naik,Nayak

, p. 982 - 984 (2007/10/02)

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