538-75-0

538-75-0 - Names and Identifiers

Name	N,N'-Dicyclohexylcarbodiimide
Synonyms	DCC dcc solution Dicyclohexylcarbodiimide Dicyclohexyl CARBODIMIDE N,N'-diphenylcarbodiimide N,N'-Dicyclohexylcarbodimide N,N-dicyclohexylcarbodiimide N,N'-Dicyclohexylcarbodiimide N,N-dicyclohexyl carbodiimide N,N'-Dicyclohexyl carbodiimide DCC Dicyclohexylcarbodiimide n,n'-dicyclohexylcarbodiimide solution N,N'-Dicyclohexylcarbodiimide [for Peptide Synthesis] N,N'-Dicyclohexylcarbodiimide, 1 M solution in dichloromethane N,N'-Dicyclohexylcarbodiimide, 0.1M sol.in DCM, peptide synthesis grade N,N'-Dicyclohexylcarbodiimide, 1M sol. In N-methylpyrrolidone,peptide synth.grade
CAS	538-75-0
EINECS	208-704-1
InChI	InChI=1/C13H10N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h1-10H
InChIKey	QOSSAOTZNIDXMA-UHFFFAOYSA-N

538-75-0 - Physico-chemical Properties

Molecular Formula	C13H22N2
Molar Mass	206.33
Density	1.247g/mLat 25°C
Melting Point	34-35°C(lit.)
Boling Point	122-124°C6mm Hg(lit.)
Flash Point	190°F
Water Solubility	Reaction
Solubility	Soluble in benzene, ethanol, ether, insoluble in water
Vapor Presure	1.044-1.15Pa at 20-25℃
Appearance	Pale yellow liquid
Specific Gravity	1.247
Color	White to pale yellow
Merck	14,3096
BRN	610662
Storage Condition	Store below +30°C.
Stability	Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents. Avoid exposure to air or moisture.
Sensitive	Moisture Sensitive
Refractive Index	n20/D 1.48
MDL	MFCD00011659
Physical and Chemical Properties	Appearance white crystal or light yellow transparent liquid melting point 34-35 ℃
Use	Used as biochemical reagents and organic synthesis dehydration condensation agent

538-75-0 - Risk and Safety

Risk Codes	R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R34 - Causes burns R40 - Limited evidence of a carcinogenic effect R43 - May cause sensitization by skin contact R41 - Risk of serious damage to eyes R36/38 - Irritating to eyes and skin. R21 - Harmful in contact with skin R24 - Toxic in contact with skin R22 - Harmful if swallowed R62 - Possible risk of impaired fertility R37/38 - Irritating to respiratory system and skin. R10 - Flammable R61 - May cause harm to the unborn child R26 - Very Toxic by inhalation R38 - Irritating to the skin R20/22 - Harmful by inhalation and if swallowed.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S41 - In case of fire and / or explosion do not breathe fumes. S24 - Avoid contact with skin. S37/39 - Wear suitable gloves and eye/face protection S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S16 - Keep away from sources of ignition. S53 - Avoid exposure - obtain special instructions before use. S28 - After contact with skin, wash immediately with plenty of soap-suds.
UN IDs	UN 2922 8/PG 2
WGK Germany	3
RTECS	FF2160000
FLUKA BRAND F CODES	3-8-10-21
TSCA	Yes
HS Code	29252000
Hazard Class	6.1
Packing Group	II
Toxicity	LD50 orally in Rabbit: 1110 mg/kg LD50 dermal Rat 71 mg/kg

538-75-0 - Upstream Downstream Industry

Raw Materials

Cyclohexylamine
Urea

538-75-0 - Reference

Reference

1. Zhang Xing, Wang, Ying, Cheng, Ya Ting, et al. Preparation of specific single domain heavy chain antibody against perfluorooctanoic acid [J]. Environmental and Occupational Medicine, 2015,32(008):744-748.
2. Chen Yangyang, Geng Xue, Qu Zi Yu, et al. Preparation and in vitro release characteristics of ursolic acid/PF127/TPGS-doxorubicin mixed nano-micelles [J]. China Pharmacy, 2019(20).
3. Du Xu, Wang Qin, Liu Yang, Ma Lixia, Zhu AI-Chen, Wang Xianpeng, Wang Chuan-dong. Synthesis and properties of four-arm star biotinylated poly (ethylene glycol)-polylactide [J]. Chemistry and bioengineering, 2015,32(03):36-39.
4. [IF = 4.821] Wan Qiu Xia et al."Synthesis of photoaffinity Labelled activity-based protein profiling probe and production of natural TetR protein for immunoassay of tetracyclines in milk."Microchem J. 2021 Nov;170:106779
5. [IF=3.591] Guichen Li et al."Poly(HPMA)-chlorambucil conjugate nanoparticles: facile fabrication and in vitro anti-cancer activity."New J Chem. 2021 Oct;45(39):18544-18551

538-75-0 - Nature

Open Data Verified Data

White crystalline or yellowish transparent liquid. The melting point was 35-36 °c. Boiling point 154~156 ℃(1. 47kPa),98~100 ℃(66. 7kPa), insoluble in water, soluble in benzene, ethanol, ether.

Last Update：2024-01-02 23:10:35

538-75-0 - Preparation Method

Open Data Verified Data

The dicyclohexylthiourea method is industrially obtained by reacting cyclohexylamine with carbon disulfide to form N,N'-cyclohexylthiourea, which is subjected to hydrogen sulfide removal.
dicyclohexylamine-urea process
N,N'-cyclohexylurea method

Last Update：2022-01-01 10:39:05

538-75-0 - Use

Open Data Verified Data

This product is a raw material for organic synthesis. Mainly used for glutathione dehydrating agent, but also for the synthesis of acids, anhydrides, aldehydes, ketones, etc. It can also be used in the synthesis of peptides and nucleic acids.

Last Update：2022-01-01 10:39:05

538-75-0 - Reference Information

LogP	5.567-6.83 at 25℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
introduction	dicyclohexylcarbodiimide (DCC) is also used for the synthesis and dehydration of amikacin and amino acids. it is a good low-temperature biochemical dehydrating agent and is also used for the synthesis of acids, anhydrides, aldehydes, ketones, etc. In Japan, dehydrating agents used for glutathione account for 90% of total consumption. When the product is used as a dehydration and condensing agent, it can be reacted in a short time at room temperature, and the product after the reaction is dicyclohexylurea.
application	dicyclohexylcarbodiimide (DCC) is an excellent polypeptide condensing agent, widely used in the synthesis of peptides, nucleic acids and amikacin.
first aid measures	if dicyclohexylcarbodiimide is inhaled, please move the patient to fresh air; If the skin is in contact with the skin, remove the contaminated clothing, rinse the skin thoroughly with soapy water and clear water, and see a doctor if you feel uncomfortable. If the eyes are in contact with clear eyes, separate the eyelids, rinse with flowing water or normal saline, and seek medical treatment immediately; if ingested, gargle immediately, forbid vomiting, should seek medical attention immediately.
use	used for the synthesis and dehydration of amikacin and amino acids. it is a good low-temperature biochemical dehydrating agent and is also used for the synthesis of acids, anhydrides, aldehydes, ketones, etc. In Japan, dehydrating agents used for glutathione account for 90% of total consumption. When the product is used as a dehydration and condensing agent, it can be reacted in a short time at room temperature, and the product after the reaction is dicyclohexylurea. Since the solubility of the product in the organic solvent is very small, the reaction product is easy to separate; at the same time, because the product is difficult to dissolve in water, the reaction can still proceed even in an aqueous solution. The product is also used for the synthesis of peptides and nucleic acids. The use of this product can easily synthesize peptides from compounds with free carboxyl groups and compounds with free amino groups at room temperature, and the yield is very high. Used for the production of hypertensives and cyclic adenosine monophosphate. used as biochemical reagent and organic synthesis dehydration condensing agent mainly used for the synthesis and dehydration of amikacin and amino acids, is a good low-temperature biochemical dehydrating agent mainly used for the artificial synthesis of peptides Condensation of amino acids. For example, in Fmoc-solid phase synthesis, the carboxyl group of an amino acid forms an amide bond with the amino group of another amino acid. In order to make the carboxyl group more receptive to the attack of nucleophiles, the negatively charged oxygen atom needs to be activated into a better leaving group, and DCC plays this role. The oxygen atom of the carboxyl group on the amino acid acts as a nucleophile to attack the carbon atom in the middle of the DCC molecule so that the DCC combines with the carboxyl group to form an ester structure, making the nucleophilic attack of the amino group easy to carry out coupling reagent; dehydration reagent; modification of bovine heart mitochondria Transhydrogenase; F1F0-adenosine triphosphate and other hydrogenase inhibitors
Production method	1. The dicyclohexyl thiourea method industrially reacts with cyclohexylamine and carbon disulfide to produce N,N'-dicyclohexyl thiourea, which is obtained by dehydrogenation. 2. The dicyclohexylamine urea method can also be obtained by the reaction of N,N'-dicyclohexylurea and phosphorus pentoxide in pyridine.
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)