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538-75-0

Basic Information
CAS No.: 538-75-0
Name: Dicyclohexylcarbodiimide
Article Data: 104
Molecular Structure:
Molecular Structure of 538-75-0 (Dicyclohexylcarbodiimide)
Formula: C13H22N2
Molecular Weight: 206.331
Synonyms: Carbodiimide,dicyclohexyl- (6CI,7CI,8CI);1,3-Dicyclohexylcarbodiimide;Bis(cyclohexyl)carbodiimide;DCC;DCCD;DCCI;Cyclohexanamine,N,N'-methanetetraylbis-;N,N'-Dicyclohexylcarbodiimide;NSC30022;NSC 53373;NSC 57182;N, N’-Dicyclohexylcarbodiimide (DCC);
EINECS: 208-704-1
Density: 1.06 g/cm3
Melting Point: 34-35 °C(lit.)
Boiling Point: 277 °C at 760 mmHg
Flash Point: 113.1 °C
Solubility: reaction with water
Appearance: colorless solid
Hazard Symbols: ToxicT, HarmfulXn
Risk Codes: 23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61
Safety: 26-36/37/39-45-41-24-37/39-24/25-36-16-53
PSA: 24.72000
LogP: 3.82570
Synthetic route
2387-23-7

1,3-Dicyclohexylurea

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With dichloromethylenedimethyliminium chloride; triethylamine In dichloromethane at 0℃;100%
With bis(trichloromethyl) carbonate In 1-methyl-pyrrolidin-2-one at 30 - 40℃; for 6h; Autoclave;99.5%
With pyridine; chloroacetyl chloride In dichloromethane at 0 - 60℃; for 10h; Solvent; Temperature; Reagent/catalyst;97.3%
1212-29-9

1,3-dicyclohexylthiourea

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With dicarbonyl(cyclopentadienyl)methyliron(II) In tetrahydrofuran at 60℃; for 24h; Reagent/catalyst; Inert atmosphere;99%
With dicarbonyl(cyclopentadienyl)methyliron(II); Triethoxysilane In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere;95%
With 1,1'-Thiocarbonyldi-2(1H)-pyridone In toluene for 8h; Heating;94%
114316-64-2

N,N'-Dicyclohexyl-C-chlor-formamidinium

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With sodium hydroxide In water92.4%
3173-53-3

Cyclohexyl isocyanate

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
O=P(MeNCH2CH2)3N at 200 - 230℃; for 91h;92%
at 20 - 230℃; for 4h; Product distribution / selectivity; Molecular sieve;30.8%
[C5H5Fe(CO)2]2 In xylene for 24h; Heating;27%
1212-29-9

1,3-dicyclohexylthiourea

A

142-08-5

2-hydroxypyridin

B

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With di-2-pyridyl thionocarbonate; dmap In acetonitrile at 80℃; for 15h;A n/a
B 84%
2387-23-7

1,3-Dicyclohexylurea

603-35-0

triphenylphosphine

A

538-75-0

dicyclohexyl-carbodiimide

B

791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With aluminum oxide; LutClO4 constant current electrolysis;A 72%
B n/a
With aluminum oxide; LutClO4 In dichloromethane constant current electrolysis;A 72%
B n/a
1212-29-9

1,3-dicyclohexylthiourea

603-35-0

triphenylphosphine

A

538-75-0

dicyclohexyl-carbodiimide

B

3878-45-3

triphenylphosphine sulfide

Conditions
ConditionsYield
With aluminum oxide; LutClO4 In dichloromethane constant current electrolysis;A 56%
B n/a
1212-29-9

1,3-dicyclohexylthiourea

603-35-0

triphenylphosphine

A

538-75-0

dicyclohexyl-carbodiimide

B

791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With aluminum oxide; LutClO4 In dichloromethane constant current electrolysis;A 56%
B n/a
2387-23-7

1,3-Dicyclohexylurea

A

931-53-3

Cyclohexyl isocyanide

B

2666-80-0

N-cyclohexylimidocarbonyl dichloride

C

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In chloroform for 4h; Heating;A 21%
B 38%
C 18%
931-53-3

Cyclohexyl isocyanide

108-91-8

cyclohexylamine

A

2387-23-7

1,3-Dicyclohexylurea

B

538-75-0

dicyclohexyl-carbodiimide

Conditions
ConditionsYield
With oxygen; sodium carbonate; palladium diacetate In acetonitrile at 100℃; under 2068.6 Torr; for 3h;A 10 % Chromat.
B 35%
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    Product name Dicyclohexylcarbodiimide Synonyms 1,3-DICYCLOHEXYLCARBODIIMIDE CAS No. 538-75-0 EINECS No. 208-704-1 Molecular Formula C13

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Specification

1.Introduction of Dicyclohexylcarbodiimide

Dicyclohexylcarbodiimide,with its CAS NO.538-75-0,is a kind of white or slight yellow crystalline solid. It has synonyms of 1,3-Dicyclohexylcarbodiimide ; Bis(cyclohexyl)carbodiimide ; Carbodicyclohexylimide ; DCC ; DCCD ; DCCI ; N,N'-Dicyclohexylcarbodiimide ; N,N'-Methanetetraylbiscyclohexaamine and NSC 30022. Dicyclohexylcarbodiimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. It is probably combustible.

2.Properties of Dicyclohexylcarbodiimide

(1) Molecular Weight 206.32718 [g/mol]  (2) Molecular Formula C13H22N2  (3) XLogP3-AA 4.7
(4) H-Bond Acceptor 2  (5) Rotatable Bond Count 2  (6) Exact Mass 206.178299
(7) MonoIsotopic Mass 206.178299  (8) Topological Polar Surface Area 24.7  (9) Heavy Atom Count 15 
(10) Complexity 201  (11) Covalently-Bonded Unit Count 1  (12) Feature 3D Acceptor Count 2
(13) Feature 3D Cation Count 1  (14) Feature 3D Ring Count 2 (15) Effective Rotor Count 4.4
(16) Conformer Sampling RMSD 0.6  (17) CID Conformer Count 23
 

3.Structure descriptors of  Dicyclohexylcarbodiimide

Canonical SMILES: C1CCC(CC1)N=C=NC2CCCCC2
InChI: InChI=1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2
InChIKey: QOSSAOTZNIDXMA-UHFFFAOYSA-N
 

4.Safety information of Dicyclohexylcarbodiimide

Hazard Codes: ToxicT,HarmfulXn
Risk Statements: 23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61
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
Safety Statements: 26-36/37/39-45-41-24-37/39-24/25-36-16-53
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 label where 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 - No smoking
S53: Avoid exposure - obtain special instruction before use
RIDADR: UN 2922 8/PG 2
WGK Germany: 3
RTECS: FF2160000
F: 3-8-10-21: Hygroscopic. Photosensitive. Keep under argon. Sensitive to humidity.
HazardClass: 6.1
PackingGroup: II
 

5.Production of Dicyclohexylcarbodiimide

Dicyclohexylcarbodiimide has several synthesis methods. Pri-Bara et al. use palladium acetate, iodine, and oxygen to couple cyclohexyl amine and cyclohexyl isocyanide. 
C6H11NC + C6H11NH2 + O2 → (C6H11N)2C + H2O
Tang et al. condense two isocyanates using the catalyst OP(MeNCH2CH2)3N in yields of 92%:

 Dicyclohexylcarbodiimide has also been made from dicyclohexylurea using a phase transfer catalyst by Jaszay et al. The disubstituted urea, arenesulfonyl chloride, and potassium carbonate react in toluene in the presence of benzyl trimethylammonium chloride to give Dicyclohexylcarbodiimide in 50% yield.

6.Toxity data of Dicyclohexylcarbodiimide

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin 10mL/kg (10mL/kg)   National Technical Information Service. Vol. OTS0555962,
mouse LD50 intraperitoneal > 800mg/kg (800mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0555962,
mouse LD50 oral > 800mg/kg (800mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0555962,
rat LC50 inhalation 159mg/m3/6H (159mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0555962,
rat LD50 intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
National Technical Information Service. Vol. OTS0555962,
rat LD50 oral 400mg/kg (400mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0555962,