1,2-Diaminocyclohexane

HCID 4610CAS 694-83-7

Basic information

Standard SMILES
NC1CCCCC1N
InChIKey
SSJXIUAHEKJCMH-UHFFFAOYSA-N
Molecular formula
C6H14N2
Average molar mass
114.19 g/mol
Monoisotopic mass
114.11569845

Overview

1,2-diaminocyclohexane appears as a clear to light yellow liquid. Corrosive to the eyes, skin, mouth, throat and stomach. Vapors may irritate eyes.

Names & identifiers

Preferred name
1,2-Diaminocyclohexane
IUPAC
cyclohexane-1,2-diamine
English name
1,2-Diaminocyclohexane
Molecular formula
C6H14N2
Molecular weight
114.19

Names & synonyms

1,2-Cyclohexanediaminecyclohexane-1,2-diamine694-83-71,2-DIAMINOCYCLOHEXANECyclohex-1,2-ylenediamineDTXSID0027301DACHC82TX76BHHDTXCID707301Dytek DCH 99RefChem:4114361,2-DACH
Show more names
(1R,2R)-CYCLOHEXANE-1,2-DIAMINEDiaminocyclohexane(R,R)-1,2-DIAMINOCYCLOHEXANEDCH-99R-DACHRR-DIAMINOCYCLOHEXANE(R,R)-(-)-1,2-DIAMINOCYCLOHEXANE
211-776-7(rel)-OxaliplatinMFCD000014911,2-CylohexanediamineCAS-694-83-7cis-1,2-CyclohexandiamineHSDB 5748trans-1,2-Cyclohexaneiamine

Database identifiers

CAS
694-83-7
PubChem CID
4610
DTXSID
DTXSID0027301
ChEMBL
CHEMBL1356279
ChEBI
CHEBI:93778
EC Number
211-776-7
Nikkaji
J6.937J

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
52 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
DrugsPharmaceuticals
Density0.952 @ 20°C
Flash PointFlash point > 93 °C
Vapor Pressure0.4 [mmHg]
Physical Description · 3 items

1,2-diaminocyclohexane appears as a clear to light yellow liquid. Corrosive to the eyes, skin, mouth, throat and stomach. Vapors may irritate eyes.

CBI; Liquid

Dark liquid with an amine odor; [CAMEO]

Physicochemical properties

Melting point
41 · 41-45 °C
Boiling point
92 · 92-93 °C18 mm Hg(lit.)
Density
0.931 g/mL · 0.931 g/mL at 25 °C(lit.)
vapor pressure
0.4 mm · 0.4 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.49(lit.)
Flash point
169 °F · 169 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.2% (6 of 513) of reports.

Danger

H302+H312+H332 (16.2%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 513 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 1,2-Cyclohexanediamine

1,2-Cyclohexanediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Cyclohexanediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 12-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14903

1,2-Cyclohexanediamine: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive
Fire HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Hazards Summary · 1 item

A corrosive substance; [CAMEO] Effects during recovery period from a 4-hour, lethal-concentration study of rats include skin lesions, discharge from the nose, and labored breathing; Lesions of the nasal mucosa observed in 2-week inhalation study with rats; No other gross or histopathological changes observed; Considered a severe skin and moderate eye irritant based on studies with rabbits; Not sensitizing to skin of guinea pigs; Dermal LD50 (test substance 69.5% 1,6-Hexanediamine and 30.5% 1,2-Diaminocyclohexane) = 7500 mg/kg in albino rabbits and produced severe irritation with necrosis; [EPA HPVIS] Observations in 28-day feeding with rats at highest tested dose (500 mg/kg) include pale discoloration of liver and increased liver enzymes; Decrease in litter size and increased postnatal loss at highest dose; Caused skin sensitization in guinea pigs (20/20 at 24 hours and 13/20 at 48 hours) [ToxPlanet: TSCATS] Causes burns; Potential skin sensitizer; May cause acute pneumonitis after inhalation; [Alfa Aesar MSDS]

Reactive GroupAmines, Phosphines, and Pyridines

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First AidExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Protective Action Criteria (PAC) · 3 items

2.1 [mg/m3]

23 [mg/m3]

140 [mg/m3]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Non-Human Toxicity Excerpts · 1 item

WITHOUT EXTERNAL ACTIVATION, CIS- AND TRANS-DICHLORODIAMMINEPLATINUM(II) (DDP) AND THE CIS-, TRANS (-)-, AND TRANS (+) FORMS OF DICHLORO-1,2-DIAMINOCYCLOHEXANEPLATINUM(II) (DDCP) AND CIS-, TRANS (-), TRANS (+)-SULFATO-1,2-DIAMINOCYCLOHEXANEPLATINUM(II) (SHP) SHOWED A 400-FOLD RANGE OF MUTAGENICITY FOR SALMONELLA TYPHIMURIUM TA100 AND TA98; THEY WERE 2-10 TIMES MORE MUTAGENIC FOR STRAIN TA100 THAN FOR STRAIN TA98. FOR THE DIAMINOCYCLOHEXANE COMPLEXES, MUTAGENIC ACTIVITY WAS STRONGLY DEPENDENT ON STEREOISOMER OF THE DIAMINOCYCLOHEXANE IN THE COMPLEX. WITH STRAIN TA100, THE THE TRANS(+) FORMS OF DDCP & SHP PRODUCED 220 AND 66 REVERTANTS/NMOL, RESPECTIVELY, WHILE THE CIS AND TRANS(-) ISOMERS INDUCED ONLY 10 AND 5% AS MANY REVERTANTS AS THE TRANS(+) FORMS.

Toxicity DataLCLo (rat) = 3,200 mg/m3/4h

Safety data

F
34
wgk
3
tsca
TSCA listed
rtecs
GU8749500
ridadr
UN 3259 8/PG 2
hs_code
29213099

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

/PLATINUM CO-ORDINATION COMPLEXES/ SHARE THE COMMON FORMULA PTA2X2... THE ACTIVE LIGANDS ARE MONODENTATE ANIONS OF INTERMEDIATE LEAVING ABILITY, WHEREAS THE AMINE A LIGANDS INFLUENCE THE SOLUBILITY OF THE COMPLEX. THE STEREOSPECIFICITY OF THE ANTI-TUMOR EFFECT IS AN IMPORTANT PROPERTY OF THE PLATINUM COMPLEXES. ... INDIRECT EVIDENCE SUGGESTS THAT BINDING TO ADJACENT GUANINE BASES IN THE SAME DNA STRAND IS IMPORTANT TO THE MODE OF ACTION. AFTER INITIAL BINDING TO GUANINE BASES, DNA BECOMES LOCALLY DENATURED AND EXPOSES ADDITIONAL CROSS-LINKING SITES. /PLATINUM COMPLEXES/

...THE TOXIC EFFECT ON ANIMALS OF PLATINUM ITSELF DIFFERS ESSENTIALLY FROM THAT OF THE COMPLEX SALTS. ...THE ACTION OF THESE SALTS IS NOT DUE TO THE SEPARATE COMPONENTS, PLATINUM AND THE BASE, BUT TO THAT OF THE MOLECULE AS A WHOLE ON SENSITIVE TISSUES, AND THEIR PHYSIOLOGICAL EFFECT, THOUGH VARYING IN DEGREE, IS IDENTICAL IN CHARACTER. ...AN INCREASE IN THE VALENCY OF THE AMMONIUM COMPONENT WAS ASSOCIATED WITH A STRONGER "CURARE-LIKE" ACTION WHILE A CHANGE IN THE VALENCY OF THE PLATINUM HAD NO INFLUENCE ON THE TOXIC EFFECT. /PLATINUM COMPLEXES/

Uses & manufacturing

Uses · 2 items

Used to make bicyclic pyrazine derivatives; [HSDB]

SYNTHESIS OF BICYCLIC PYRAZINE DERIVATIVES

U.S. Production2023: 2,500,000 - <4,000,000 lb
Industry UsesOther
Household ProductsInformation on 18 consumer products that contain Cyclohex-1,2-ylenediamine in the following categories is provided:
General Manufacturing Information · 2 items

Services

1,2-Cyclohexanediamine: ACTIVE

Applications · 4 items

Usessuzuki reaction

Uses1,2-Diaminocyclohexane was used in the synthesis of chiral ruthenium(IV)-oxo complexes & bicyclic pyrazine derivatives.

Uses1,2-Diaminocyclohexane was used in the synthesis of chiral ruthenium(IV)-oxo complexes.

General Description1,2-Diaminocyclohexane undergoes non-templated reaction with homochiral as well as the racemic form of trans-1,2-diaminocyclohexane with terephthaldehyde to yield (3+3)-cyclocondensed molecular triangles. It acts as ligand and forms organotin complexes, having potential applications as metal-based antitumour drugs.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: Cyclohexane-1,2-diamine is a primary aliphatic amine.

Related reactions

264 records

Linked notes

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